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This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move into the living room with marble surround fireplace that is sun-filled and bright. This leads you to the enclosed porch area where you can bask in the sun with walls of windows & surrounded by private, beautiful and mature landscaping. This home truly brings the outdoors inside to you! The dining room is perfect for hosting events and leads to the white eat-in kitchen with an island and double ovens that is very spacious for cooking and entertaining. The kitchen is conveniently located next to the first-floor laundry room. Down the hall from the kitchen is a huge wood beamed ceiling family room with patio doors that open to the outside, a fireplace with granite surround and built-in bookshelves where the media resides. The octagonal office with an oversized vaulted ceiling and is flanked with floor to ceiling windows and beautiful built-in bookshelves. Working from home has never been more relaxing in this serene setting. Take the steps off the family room up to the recreation room where you can play pool, games or watch tv in this amazing playroom area. The functionality of having a large first floor primary suite, with attached bathroom, closets galore, near your own outdoor oasis is spectacular. You are in your own bed and breakfast when sleeping in the first-floor primary suite retreat surrounded by gardens and a bluestone walkway. The second floor has three additional bedrooms and two full bathrooms. With an attached 3 car garage, circular driveway on the property and parking for guests in front of the home, you are ready to host any event at this incredible home. The lower level has storage galore and a wine cellar. This is a very special home that has been well loved for many years on the most incredible and expansive property.

4 Beds ⋅ 5 Baths ⋅ 12620950 MLS ⋅ CLOSED Status

This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move into the living room with marble surround fireplace that is sun-filled and bright. This leads you to the enclosed porch area where you can bask in the sun with walls of windows & surrounded by private, beautiful and mature landscaping. This home truly brings the outdoors inside to you! The dining room is perfect for hosting events and leads to the white eat-in kitchen with an island and double ovens that is very spacious for cooking and entertaining. The kitchen is conveniently located next to the first-floor laundry room. Down the hall from the kitchen is a huge wood beamed ceiling family room with patio doors that open to the outside, a fireplace with granite surround and built-in bookshelves where the media resides. The octagonal office with an oversized vaulted ceiling and is flanked with floor to ceiling windows and beautiful built-in bookshelves. Working from home has never been more relaxing in this serene setting. Take the steps off the family room up to the recreation room where you can play pool, games or watch tv in this amazing playroom area. The functionality of having a large first floor primary suite, with attached bathroom, closets galore, near your own outdoor oasis is spectacular. You are in your own bed and breakfast when sleeping in the first-floor primary suite retreat surrounded by gardens and a bluestone walkway. The second floor has three additional bedrooms and two full bathrooms. With an attached 3 car garage, circular driveway on the property and parking for guests in front of the home, you are ready to host any event at this incredible home. The lower level has storage galore and a wine cellar. This is a very special home that has been well loved for many years on the most incredible and expansive property.

92 Indian Hill Road, Winnetka

$4,300,000

Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES a Village approved subdivided .67 acre buildable lot option so you can sell off OR use & expand your dream estate with a second structure with separate service entrance. Inviting presence with circular drive & framed manicured grounds presents a very storybook residence with classic architecture, new composite cedar shake roof, copper gutters, and charming dormers creating unforgettable curb appeal. A welcoming covered front porch sets the tone as you enter the foyer thru the Farrow & Ball French blue doors, brick flooring and Nantucket inspired millwork. This expansive ranch with southern exposure naturally lights up the entire house as the formal living with picturesque windows showcases the breathtaking views of the expansive grounds & tennis court. Just beyond, the spectacular sunroom/family room serves as the heart of the home with panoramic views of the lush backyard and entertaining terraces, creating an effortless indoor-outdoor connection. The dining room offers an intimate yet refined setting for gatherings and leads to the updated classic all white kitchen accented with Carrera marble and designed by notable North Shore architect Chip Hackely. Custom cabinetry accented with huge breakfast bar island with seating for 6 and expansive prep space make this the hub of the house with great views of Sunset Road. An adjoining breakfast area surrounded by French doors overlooks the picturesque property and opens directly to the outdoors. Additional first floor living spaces include an inviting den with vaulted ceilings, custom built-ins, and stone fireplace, offering the perfect retreat for relaxing, entertaining or expansive option to make primary suite larger. Completing the main level is the luxurious first-floor primary suite, a peaceful sanctuary with rolling green views and spa stone bath. The spacious second floor continues with five family sized beds and three updated all white marble baths, including two private ensuite retreats and an additional hall bath. Each bedroom is flooded with light and can also be a perfect place to expand the house if needed. One of the bedrooms is currently being utilized as a sophisticated office space. The lower level offers an exceptional additional living space centered around a large recreation room, kitchenette, laundry center. Enchanting outdoor space with blue stone patios, tennis court and miniature replica playhouse make this property so special as there in incredible opportunity with second lot to elevate to another level of luxury by adding a 20x40 pool with separate tricked out cabana house with wellness gym, golf simulator room, 2nd office and guest quarters. If you rather just live in the house and sell off the back land, that is a fabulous option as well or even live as the house is now and plan for the future, it all works here. This opportunity is one of kind as there are many different ways to optimize 936 Sunset all while being in an A++ location, south of Willow, steps to Crow Island, FCH, and NSCD schools and either way to New Trier or Loyola, plus, don't forget, town and the train are right there too. This is your optimal long term forever house option as there many customized opportunities to make this your own. Either right away or over time, the most important this is that you have SECURED a prime address on the street that falls right behind living on the lake. The ultimate North Shore investment property to be offered in years!

6 Beds ⋅ 6 Baths ⋅ 12660037 MLS ⋅ CLOSED Status

Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES a Village approved subdivided .67 acre buildable lot option so you can sell off OR use & expand your dream estate with a second structure with separate service entrance. Inviting presence with circular drive & framed manicured grounds presents a very storybook residence with classic architecture, new composite cedar shake roof, copper gutters, and charming dormers creating unforgettable curb appeal. A welcoming covered front porch sets the tone as you enter the foyer thru the Farrow & Ball French blue doors, brick flooring and Nantucket inspired millwork. This expansive ranch with southern exposure naturally lights up the entire house as the formal living with picturesque windows showcases the breathtaking views of the expansive grounds & tennis court. Just beyond, the spectacular sunroom/family room serves as the heart of the home with panoramic views of the lush backyard and entertaining terraces, creating an effortless indoor-outdoor connection. The dining room offers an intimate yet refined setting for gatherings and leads to the updated classic all white kitchen accented with Carrera marble and designed by notable North Shore architect Chip Hackely. Custom cabinetry accented with huge breakfast bar island with seating for 6 and expansive prep space make this the hub of the house with great views of Sunset Road. An adjoining breakfast area surrounded by French doors overlooks the picturesque property and opens directly to the outdoors. Additional first floor living spaces include an inviting den with vaulted ceilings, custom built-ins, and stone fireplace, offering the perfect retreat for relaxing, entertaining or expansive option to make primary suite larger. Completing the main level is the luxurious first-floor primary suite, a peaceful sanctuary with rolling green views and spa stone bath. The spacious second floor continues with five family sized beds and three updated all white marble baths, including two private ensuite retreats and an additional hall bath. Each bedroom is flooded with light and can also be a perfect place to expand the house if needed. One of the bedrooms is currently being utilized as a sophisticated office space. The lower level offers an exceptional additional living space centered around a large recreation room, kitchenette, laundry center. Enchanting outdoor space with blue stone patios, tennis court and miniature replica playhouse make this property so special as there in incredible opportunity with second lot to elevate to another level of luxury by adding a 20x40 pool with separate tricked out cabana house with wellness gym, golf simulator room, 2nd office and guest quarters. If you rather just live in the house and sell off the back land, that is a fabulous option as well or even live as the house is now and plan for the future, it all works here. This opportunity is one of kind as there are many different ways to optimize 936 Sunset all while being in an A++ location, south of Willow, steps to Crow Island, FCH, and NSCD schools and either way to New Trier or Loyola, plus, don't forget, town and the train are right there too. This is your optimal long term forever house option as there many customized opportunities to make this your own. Either right away or over time, the most important this is that you have SECURED a prime address on the street that falls right behind living on the lake. The ultimate North Shore investment property to be offered in years!

936 Sunset Road, Winnetka

$900,000

Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning fireplace, an expansive updated kitchen with abundant cabinetry, and a dining area flanked by windows with plantation shutters. A bonus family room with vaulted ceilings and skylights, along with a full bathroom, adds valuable flexibility and completes the main level. Upstairs, you'll find two bedrooms with hardwood floors and a shared hall bath. The finished basement offers even more living space, featuring a second fireplace, a wall of closets, and a utility room with additional storage. Step outside to a picturesque, professionally landscaped garden with two patios and plenty of space for relaxing or entertaining. From its inviting curb appeal to its surprisingly spacious interior, this home strikes the perfect balance between charm and function. Timeless details and thoughtful updates are complimented by a versatile layout designed for comfortable everyday living and effortless entertaining.

2 Beds ⋅ 2 Baths ⋅ 12671135 MLS ⋅ CLOSED Status

Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning fireplace, an expansive updated kitchen with abundant cabinetry, and a dining area flanked by windows with plantation shutters. A bonus family room with vaulted ceilings and skylights, along with a full bathroom, adds valuable flexibility and completes the main level. Upstairs, you'll find two bedrooms with hardwood floors and a shared hall bath. The finished basement offers even more living space, featuring a second fireplace, a wall of closets, and a utility room with additional storage. Step outside to a picturesque, professionally landscaped garden with two patios and plenty of space for relaxing or entertaining. From its inviting curb appeal to its surprisingly spacious interior, this home strikes the perfect balance between charm and function. Timeless details and thoughtful updates are complimented by a versatile layout designed for comfortable everyday living and effortless entertaining.

376 Rosewood Avenue, Winnetka

$1,150,531

Welcome to 650 Winnetka Mews #310, a completely reimagined and exquisitely redesigned luxury condominium in the historic Winnetka Mews. Thoughtfully renovated from floor to ceiling, showcasing exceptional craftsmanship, sophisticated finishes, new mechanical systems, custom closets, all new interior doors, and impeccable attention to detail throughout. The stunning chef's kitchen features custom cabinetry, a walk-in pantry, honed Taj Mahal quartzite countertops highlighted by a dramatic 3-inch mitered-edge island, premium built-in refrigeration, high-end appliances, designer Kelly Wearstler lighting, and a Perrin & Rowe polished nickel faucet. The open-concept living and dining spaces are anchored by a breathtaking custom marble fireplace, creating a warm yet sophisticated gathering place. The bathrooms feature Brizo fixtures, Robern mirrors, custom vanities, and furniture-style linen storage. A thoughtfully designed mudroom with timeless checkerboard tile flooring provides both style and function, while wide-plank engineered wood flooring, luxurious wool carpeting, Visual Comfort Lighting and EMTEK door hardware add warmth and elegance throughout. All work has been fully permitted and inspected by the Village of Winnetka. New windows and sliding doors have been fully paid for and are scheduled for installation by the HOA in August, offering exceptional value. Experience the unparalleled combination of timeless design, modern functionality, and premium materials. This exceptional residence delivers an elevated lifestyle just moments from downtown Winnetka, Lake Michigan beaches, Metra, boutique shopping, acclaimed restaurants, and beautiful parks. Residents of Winnetka Mews enjoy an outdoor pool, fitness center, on-site management, and a dedicated building engineer, providing convenience, comfort, and peace of mind in one of the North Shore's most desirable communities.

2 Beds ⋅ 2 Baths ⋅ 12587099 MLS ⋅ CLOSED Status

Welcome to 650 Winnetka Mews #310, a completely reimagined and exquisitely redesigned luxury condominium in the historic Winnetka Mews. Thoughtfully renovated from floor to ceiling, showcasing exceptional craftsmanship, sophisticated finishes, new mechanical systems, custom closets, all new interior doors, and impeccable attention to detail throughout. The stunning chef's kitchen features custom cabinetry, a walk-in pantry, honed Taj Mahal quartzite countertops highlighted by a dramatic 3-inch mitered-edge island, premium built-in refrigeration, high-end appliances, designer Kelly Wearstler lighting, and a Perrin & Rowe polished nickel faucet. The open-concept living and dining spaces are anchored by a breathtaking custom marble fireplace, creating a warm yet sophisticated gathering place. The bathrooms feature Brizo fixtures, Robern mirrors, custom vanities, and furniture-style linen storage. A thoughtfully designed mudroom with timeless checkerboard tile flooring provides both style and function, while wide-plank engineered wood flooring, luxurious wool carpeting, Visual Comfort Lighting and EMTEK door hardware add warmth and elegance throughout. All work has been fully permitted and inspected by the Village of Winnetka. New windows and sliding doors have been fully paid for and are scheduled for installation by the HOA in August, offering exceptional value. Experience the unparalleled combination of timeless design, modern functionality, and premium materials. This exceptional residence delivers an elevated lifestyle just moments from downtown Winnetka, Lake Michigan beaches, Metra, boutique shopping, acclaimed restaurants, and beautiful parks. Residents of Winnetka Mews enjoy an outdoor pool, fitness center, on-site management, and a dedicated building engineer, providing convenience, comfort, and peace of mind in one of the North Shore's most desirable communities.

650 Winnetka Mews Unit #310, Winnetka

$1,410,000

Ideally located in coveted East Winnetka, just moments from Joseph Sears School, Lake Michigan beaches, the Metra train, and New Trier High School's East Campus, this beautifully updated home offers the perfect combination of charm, functionality, and an unbeatable location. Featuring 3 bedrooms, 4 full bathrooms, and a flexible first-floor office or optional 4th bedroom, the home is thoughtfully designed to accommodate a variety of lifestyles. Sun-filled living spaces begin with the elegant formal living room, highlighted by a beautiful bay window, fireplace and new Marvin windows throughout the home. The adjoining dining room flows seamlessly into the expansive eat-in kitchen, creating an ideal setting for both everyday living and entertaining. The inviting family room opens to a charming wraparound porch overlooking the private, fenced backyard, providing the perfect indoor-outdoor connection. A first-floor office or guest bedroom, paired with a full bath, offers exceptional flexibility for remote work, overnight guests, or multigenerational living. The second floor features three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms to comfortably accommodate family and guests. The finished lower level adds valuable living space with a recreation room, playroom, laundry area, and a newly renovated full bathroom. Completing the home are a large mudroom, an oversized detached two-car garage equipped with an electric vehicle charging station, and a spacious driveway. This exceptional residence offers an outstanding opportunity to enjoy East Winnetka living at its finest.

3 Beds ⋅ 4 Baths ⋅ 12687251 MLS ⋅ CLOSED Status

Ideally located in coveted East Winnetka, just moments from Joseph Sears School, Lake Michigan beaches, the Metra train, and New Trier High School's East Campus, this beautifully updated home offers the perfect combination of charm, functionality, and an unbeatable location. Featuring 3 bedrooms, 4 full bathrooms, and a flexible first-floor office or optional 4th bedroom, the home is thoughtfully designed to accommodate a variety of lifestyles. Sun-filled living spaces begin with the elegant formal living room, highlighted by a beautiful bay window, fireplace and new Marvin windows throughout the home. The adjoining dining room flows seamlessly into the expansive eat-in kitchen, creating an ideal setting for both everyday living and entertaining. The inviting family room opens to a charming wraparound porch overlooking the private, fenced backyard, providing the perfect indoor-outdoor connection. A first-floor office or guest bedroom, paired with a full bath, offers exceptional flexibility for remote work, overnight guests, or multigenerational living. The second floor features three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms to comfortably accommodate family and guests. The finished lower level adds valuable living space with a recreation room, playroom, laundry area, and a newly renovated full bathroom. Completing the home are a large mudroom, an oversized detached two-car garage equipped with an electric vehicle charging station, and a spacious driveway. This exceptional residence offers an outstanding opportunity to enjoy East Winnetka living at its finest.

72 Warwick Road, Winnetka

$1,670,000

If you are looking for a right-size, upsize, or downsize home that can effortlessly adapt to your changing needs, you've found your dream home. 1087 Ash is pure perfection! There is so much more than meets the eye, as the substantial addition is beautifully tucked behind the original home. Step into the sunny three-season room - perfect for morning coffee or an afternoon mahj game - and sets the reveal of the incredible space and light this home offers. The formal living room, with leaded glass windows and a wood-burning fireplace, flows into an entertainment-sized dining room and then into the thoughtfully updated kitchen, featuring chef's appliances, a large island, and banquet seating for six. An adjoining sun-filled family room with custom built-ins and a gas fireplace opens to the deck overlooking the lushly landscaped backyard. And wait for it- the big surprises on the first floor: a 4th bedroom with an adjacent full bath plus two additional bonus rooms that can flex to fit your lifestyle. Need a 5th bedroom and an office? Check. Two offices and a playroom? Check. An office, gym, or guest space? Check. These extra rooms are a true luxury! Head upstairs and you'll find two generously sized family bedrooms with great closets, a pretty hall bath, and a super spacious primary suite with vaulted ceilings, two walk-in closets, and a beautifully updated bath. The lower level adds even more versatility with a carpeted rec room, bonus room, storage space, and a large laundry/mechanical/storage area. The outside space is equally fab-the professionally landscaped yard is lovely, and there is a 2 car garage with a parking pad for 2 cars on the alley. And can we talk about the fabulous tree street location? It's a dream! No need to carpool to school- Grades K-8 Winnetka schools are just blocks away. Walk or bike Winnetka Park District golf, tennis, paddle, ice rink and ballfields, the Metra, and all of the fabulous restaurants ( Pomeroy, Tocco, Hometown and more!) and shopping in vibrant downtown Winnetka. What more could you want? 1087 Ash checks every box - and then some! Don't miss this incredible home- it is truly special!

4 Beds ⋅ 3 Baths ⋅ 12642920 MLS ⋅ CLOSED Status

If you are looking for a right-size, upsize, or downsize home that can effortlessly adapt to your changing needs, you've found your dream home. 1087 Ash is pure perfection! There is so much more than meets the eye, as the substantial addition is beautifully tucked behind the original home. Step into the sunny three-season room - perfect for morning coffee or an afternoon mahj game - and sets the reveal of the incredible space and light this home offers. The formal living room, with leaded glass windows and a wood-burning fireplace, flows into an entertainment-sized dining room and then into the thoughtfully updated kitchen, featuring chef's appliances, a large island, and banquet seating for six. An adjoining sun-filled family room with custom built-ins and a gas fireplace opens to the deck overlooking the lushly landscaped backyard. And wait for it- the big surprises on the first floor: a 4th bedroom with an adjacent full bath plus two additional bonus rooms that can flex to fit your lifestyle. Need a 5th bedroom and an office? Check. Two offices and a playroom? Check. An office, gym, or guest space? Check. These extra rooms are a true luxury! Head upstairs and you'll find two generously sized family bedrooms with great closets, a pretty hall bath, and a super spacious primary suite with vaulted ceilings, two walk-in closets, and a beautifully updated bath. The lower level adds even more versatility with a carpeted rec room, bonus room, storage space, and a large laundry/mechanical/storage area. The outside space is equally fab-the professionally landscaped yard is lovely, and there is a 2 car garage with a parking pad for 2 cars on the alley. And can we talk about the fabulous tree street location? It's a dream! No need to carpool to school- Grades K-8 Winnetka schools are just blocks away. Walk or bike Winnetka Park District golf, tennis, paddle, ice rink and ballfields, the Metra, and all of the fabulous restaurants ( Pomeroy, Tocco, Hometown and more!) and shopping in vibrant downtown Winnetka. What more could you want? 1087 Ash checks every box - and then some! Don't miss this incredible home- it is truly special!

1087 Ash Street, Winnetka

$2,960,000

Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside the impressive front hall and discover a flowing first floor anchored by a gracious living room, elegant dining room with butler's pantry and a stunning custom kitchen. Here, custom cabinetry, a large island with seating for four, double dishwashers, dual SubZero refrigerators with freezer drawers, and double ovens (and a steam oven) create a true chef's haven. A sun-filled breakfast room with bay window frames serene views of the west terrace and lush lawn, while the adjacent family room with fireplace and grand scale opens to the grilling and dining terrace, making entertaining seamless. Additional first-floor highlights include a music room with fireplace, versatile sunporch/office with French doors to the terrace, two powder rooms, and a generous mudroom connecting to the three-car attached garage with a huge walk-up attic above. The second floor offers a luxurious primary suite, complete with a private sitting room with fireplace, large bath, and generous walk-in closet. Three additional bedrooms, an updated hall bath, and a convenient laundry room complete the second level. On the third floor, a light-filled getaway offers two more bedrooms, a hall bath, and a spacious bonus room perfect for play, work, or retreat. The fully renovated (and excavated) lower level is designed for fun and relaxation, featuring a media/recreation room, large playroom, entertaining bar, sauna, and full bath. With abundant storage across all four floors-including oversized attic and basement storage rooms - this home blends charm with true functionality. Outdoors, the expansive property lives like a private park, with terraces which are ideal for alfresco dining, summer gatherings, and quiet evenings surrounded by nature. All of this in an ideal 10+ location!

6 Beds ⋅ 6 Baths ⋅ 12555408 MLS ⋅ CLOSED Status

Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside the impressive front hall and discover a flowing first floor anchored by a gracious living room, elegant dining room with butler's pantry and a stunning custom kitchen. Here, custom cabinetry, a large island with seating for four, double dishwashers, dual SubZero refrigerators with freezer drawers, and double ovens (and a steam oven) create a true chef's haven. A sun-filled breakfast room with bay window frames serene views of the west terrace and lush lawn, while the adjacent family room with fireplace and grand scale opens to the grilling and dining terrace, making entertaining seamless. Additional first-floor highlights include a music room with fireplace, versatile sunporch/office with French doors to the terrace, two powder rooms, and a generous mudroom connecting to the three-car attached garage with a huge walk-up attic above. The second floor offers a luxurious primary suite, complete with a private sitting room with fireplace, large bath, and generous walk-in closet. Three additional bedrooms, an updated hall bath, and a convenient laundry room complete the second level. On the third floor, a light-filled getaway offers two more bedrooms, a hall bath, and a spacious bonus room perfect for play, work, or retreat. The fully renovated (and excavated) lower level is designed for fun and relaxation, featuring a media/recreation room, large playroom, entertaining bar, sauna, and full bath. With abundant storage across all four floors-including oversized attic and basement storage rooms - this home blends charm with true functionality. Outdoors, the expansive property lives like a private park, with terraces which are ideal for alfresco dining, summer gatherings, and quiet evenings surrounded by nature. All of this in an ideal 10+ location!

100 Old Green Bay Road, Winnetka

$4,281,050

A rare opportunity to own one of Winnetka's most iconic and historically significant residences. Set on approximately one acre along a private lane in the heart of Hubbard Woods, this landmark Georgian Colonial Revival estate was originally home to the daughter of Mr. Hubbard and occupies one of the neighborhood's original homesites. Backing directly to the ravines and overlooking protected natural vistas, the property offers unparalleled privacy, breathtaking beauty, and a setting unlike any other on the North Shore. The lush grounds are highlighted by a spectacular 50 year old perennial garden, creating a serene backdrop for both everyday living and grand-scale entertaining, while the expansive courtyard driveway with its signature brick inlay establishes an unforgettable sense of arrival. The estate is further distinguished by one of Winnetka's few remaining 150-year-old American Elm trees, a remarkable living landmark that anchors the property's storied landscape. Just one block from Lake Michigan and less than half a mile from Tower Road Beach, the location offers effortless access to downtown Hubbard Woods, the Metra, acclaimed restaurants, boutiques, and everyday conveniences. The residence presents a masterfully executed floor plan that honors the home's rich architectural heritage while embracing the demands of modern living. Original crown molding, original hardwood flooring throughout, gracious 10-foot ceilings, and timeless architectural details create a sense of enduring elegance throughout. Thoughtfully reimagined for today's lifestyle, the expansive open-concept kitchen flows seamlessly into the family room, a rare and highly sought-after feature in a home of this pedigree. The recently renovated kitchen is appointed with quartzite countertops, limestone flooring, stainless steel appliances, and elevated designer finishes. Radiant heated floors extend throughout both the kitchen and adjoining family room, offering exceptional comfort and functionality. A formal living room, elegant library, gracious dining room, spacious family room, and two private first-floor offices provide an ideal balance of sophistication and livability. Five fireplaces enrich the home's most distinguished spaces, including the living room, dining room, library, primary suite, and a guest bedroom. Among the home's most captivating spaces is the grand screened porch, a true outdoor living room framed by soaring floor-to-ceiling white columns and opening to sweeping views of the private grounds and picturesque ravine landscape beyond. Offering seven bedrooms, four full baths, and two half baths, the upper levels are equally impressive. Beautiful marble bathrooms, two ensuite retreats, and laundry rooms on both the first and second floors provide exceptional convenience. The luxurious primary suite serves as a private sanctuary, complete with its own fireplace, dual walk-in closets, and a stunning all-marble bath with radiant heated floors. Meticulously maintained and thoughtfully improved and renovated through the years, the home features a complete cedar roof replacement in 2019, full restoration of all exterior porch and ornamental woodwork in 2021, brand new hot water heaters in 2026, and a professionally installed waterproofing and drain tile system in the basement. The unfinished lower level offers abundant storage and outstanding potential for future customization. A three car garage and expansive brick-inlaid motor court accommodate up to seven additional vehicles, further enhancing the home's exceptional functionality. Rich in history, architecturally significant, and impeccably maintained, 930 Fisher Lane represents a once-in-a-generation opportunity to own one of the North Shore's most cherished legacy estates, a remarkable offering where history, privacy, and timeless elegance converge.

7 Beds ⋅ 6 Baths ⋅ 12675225 MLS ⋅ CLOSED Status

A rare opportunity to own one of Winnetka's most iconic and historically significant residences. Set on approximately one acre along a private lane in the heart of Hubbard Woods, this landmark Georgian Colonial Revival estate was originally home to the daughter of Mr. Hubbard and occupies one of the neighborhood's original homesites. Backing directly to the ravines and overlooking protected natural vistas, the property offers unparalleled privacy, breathtaking beauty, and a setting unlike any other on the North Shore. The lush grounds are highlighted by a spectacular 50 year old perennial garden, creating a serene backdrop for both everyday living and grand-scale entertaining, while the expansive courtyard driveway with its signature brick inlay establishes an unforgettable sense of arrival. The estate is further distinguished by one of Winnetka's few remaining 150-year-old American Elm trees, a remarkable living landmark that anchors the property's storied landscape. Just one block from Lake Michigan and less than half a mile from Tower Road Beach, the location offers effortless access to downtown Hubbard Woods, the Metra, acclaimed restaurants, boutiques, and everyday conveniences. The residence presents a masterfully executed floor plan that honors the home's rich architectural heritage while embracing the demands of modern living. Original crown molding, original hardwood flooring throughout, gracious 10-foot ceilings, and timeless architectural details create a sense of enduring elegance throughout. Thoughtfully reimagined for today's lifestyle, the expansive open-concept kitchen flows seamlessly into the family room, a rare and highly sought-after feature in a home of this pedigree. The recently renovated kitchen is appointed with quartzite countertops, limestone flooring, stainless steel appliances, and elevated designer finishes. Radiant heated floors extend throughout both the kitchen and adjoining family room, offering exceptional comfort and functionality. A formal living room, elegant library, gracious dining room, spacious family room, and two private first-floor offices provide an ideal balance of sophistication and livability. Five fireplaces enrich the home's most distinguished spaces, including the living room, dining room, library, primary suite, and a guest bedroom. Among the home's most captivating spaces is the grand screened porch, a true outdoor living room framed by soaring floor-to-ceiling white columns and opening to sweeping views of the private grounds and picturesque ravine landscape beyond. Offering seven bedrooms, four full baths, and two half baths, the upper levels are equally impressive. Beautiful marble bathrooms, two ensuite retreats, and laundry rooms on both the first and second floors provide exceptional convenience. The luxurious primary suite serves as a private sanctuary, complete with its own fireplace, dual walk-in closets, and a stunning all-marble bath with radiant heated floors. Meticulously maintained and thoughtfully improved and renovated through the years, the home features a complete cedar roof replacement in 2019, full restoration of all exterior porch and ornamental woodwork in 2021, brand new hot water heaters in 2026, and a professionally installed waterproofing and drain tile system in the basement. The unfinished lower level offers abundant storage and outstanding potential for future customization. A three car garage and expansive brick-inlaid motor court accommodate up to seven additional vehicles, further enhancing the home's exceptional functionality. Rich in history, architecturally significant, and impeccably maintained, 930 Fisher Lane represents a once-in-a-generation opportunity to own one of the North Shore's most cherished legacy estates, a remarkable offering where history, privacy, and timeless elegance converge.

930 Fisher Lane, Winnetka

$2,345,000

Beautifully renovated and thoughtfully reimagined, this exceptional brick and stucco Colonial located in the heart of Hubbard Woods sits on an expanded 64 X 160 parcel, blending timeless architecture with today's most desired amenities and refined finishes. A total interior renovation completed in 2004 with added exterior renovation in 2006 and 2017 redesigns, transformed the home into a sophisticated yet comfortable residence designed for modern living. From the welcoming arched covered entry and gracious foyer to the custom millwork and gleaming hardwood floors, every detail reflects quality craftsmanship. At the heart of the home, the chef's kitchen is both stylish and functional, featuring custom cabinetry, quartzite countertops, professional stainless steel appliances, center island with seating, sunny breakfast area overlooking the professionally landscaped backyard. Beautifully scaled formal living and dining room, a private oak paneled office with custom built-ins and access to private patio. Inviting family room with its soaring ceiling and siteline to private back yard is anchored by a redesigned tile gas fireplace and thoughtfully designed wetbar complete with beverage refrigerator and ice maker. Upstairs is highlighted by a luxurious primary suite designed as a true retreat, complete with a spacious bedroom, private office, dual vanities w/shared shower room, and beautifully appointed custom walk in closet systems. Three additional bedrooms include a private en-suite and a beautifully appointed hall bath finished with timeless design and quality materials. Convenient laundry rooms are located on both the first and second floor for added flexibility. Downstairs, the finished lower level includes a large recreation room, exercise room, 5th bedroom and bath and ample storage Step outside to the grandly scaled, multi-level patio with options for multiple dining and lounging areas, surrounded by mature landscaping and private setting for outdoor entertaining. Smart mudroom with cubbies located off attached 2 car garage. A+ location walking to town, train, restaurants, beaches and Hubbard Woods School. (Square footage 1st 1,765sf; 2nd: 1,661sf; LL: 1,497sf = 4,923SF)Taxes 2025 - $29,105

5 Beds ⋅ 6 Baths ⋅ 12667432 MLS ⋅ CLOSED Status

Beautifully renovated and thoughtfully reimagined, this exceptional brick and stucco Colonial located in the heart of Hubbard Woods sits on an expanded 64 X 160 parcel, blending timeless architecture with today's most desired amenities and refined finishes. A total interior renovation completed in 2004 with added exterior renovation in 2006 and 2017 redesigns, transformed the home into a sophisticated yet comfortable residence designed for modern living. From the welcoming arched covered entry and gracious foyer to the custom millwork and gleaming hardwood floors, every detail reflects quality craftsmanship. At the heart of the home, the chef's kitchen is both stylish and functional, featuring custom cabinetry, quartzite countertops, professional stainless steel appliances, center island with seating, sunny breakfast area overlooking the professionally landscaped backyard. Beautifully scaled formal living and dining room, a private oak paneled office with custom built-ins and access to private patio. Inviting family room with its soaring ceiling and siteline to private back yard is anchored by a redesigned tile gas fireplace and thoughtfully designed wetbar complete with beverage refrigerator and ice maker. Upstairs is highlighted by a luxurious primary suite designed as a true retreat, complete with a spacious bedroom, private office, dual vanities w/shared shower room, and beautifully appointed custom walk in closet systems. Three additional bedrooms include a private en-suite and a beautifully appointed hall bath finished with timeless design and quality materials. Convenient laundry rooms are located on both the first and second floor for added flexibility. Downstairs, the finished lower level includes a large recreation room, exercise room, 5th bedroom and bath and ample storage Step outside to the grandly scaled, multi-level patio with options for multiple dining and lounging areas, surrounded by mature landscaping and private setting for outdoor entertaining. Smart mudroom with cubbies located off attached 2 car garage. A+ location walking to town, train, restaurants, beaches and Hubbard Woods School. (Square footage 1st 1,765sf; 2nd: 1,661sf; LL: 1,497sf = 4,923SF)Taxes 2025 - $29,105

1258 Scott Avenue, Winnetka

$1,730,000

Easy, in-town living in this wonderful home! This spacious home is conveniently located in the ideal 'walk to everything' location in the heart of Winnetka - close to absolutely everything. Built in 1995 with all the amenities one needs: classic center entry layout, large welcoming foyer, bright interior with an abundance of natural light, large scaled rooms, eat-in kitchen adjacent to family room which has sliding doors out to the southern patio and fully fenced yard. Primary suite with ensuite bath (with soaking tub, double vanities & separate shower), walk-in closet & skylight. Three additional bedrooms and 2 full baths round out the 2nd floor. Finished lower level with heated floors and a rec room and play area plus full bath. Plenty of storage throughout the home including the large storage room in the basement. All in move-in condition! Special amenities include first floor laundry/mudroom, 2 car attached / heated garage. This well designed and light-filled house is located on a large corner lot (50 x 187) and is bathed in sunlight all day long. A short walk to the center of downtown Winnetka for shopping, restaurants, parks and train and a short walk to K-8 schools, golf, tennis, paddle facilities and ice arena. All the space you need in all the right places!

4 Beds ⋅ 5 Baths ⋅ 12613148 MLS ⋅ CLOSED Status

Easy, in-town living in this wonderful home! This spacious home is conveniently located in the ideal 'walk to everything' location in the heart of Winnetka - close to absolutely everything. Built in 1995 with all the amenities one needs: classic center entry layout, large welcoming foyer, bright interior with an abundance of natural light, large scaled rooms, eat-in kitchen adjacent to family room which has sliding doors out to the southern patio and fully fenced yard. Primary suite with ensuite bath (with soaking tub, double vanities & separate shower), walk-in closet & skylight. Three additional bedrooms and 2 full baths round out the 2nd floor. Finished lower level with heated floors and a rec room and play area plus full bath. Plenty of storage throughout the home including the large storage room in the basement. All in move-in condition! Special amenities include first floor laundry/mudroom, 2 car attached / heated garage. This well designed and light-filled house is located on a large corner lot (50 x 187) and is bathed in sunlight all day long. A short walk to the center of downtown Winnetka for shopping, restaurants, parks and train and a short walk to K-8 schools, golf, tennis, paddle facilities and ice arena. All the space you need in all the right places!

995 Oak Street, Winnetka

$2,200,000

Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and entertaining. With 5 spacious bedrooms, 2 offices, and a beautifully finished lower level, there is space for everyone to live, work, and play in comfort and style. For added convenience, laundry rooms are thoughtfully located on both the lower level and the upper level. Outside, enjoy a fenced yard, bluestone patio, and the charm of a quiet cul-de-sac near parks and the lakefront. A half block from the highly coveted Hubbard Woods School, and only minutes from Metra, shops, restaurants, and Tower Beach, this meticulously maintained home offers luxury, comfort, and an unbeatable location in the heart of Hubbard Woods.

4 Beds ⋅ 5 Baths ⋅ 12585208 MLS ⋅ CLOSED Status

Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and entertaining. With 5 spacious bedrooms, 2 offices, and a beautifully finished lower level, there is space for everyone to live, work, and play in comfort and style. For added convenience, laundry rooms are thoughtfully located on both the lower level and the upper level. Outside, enjoy a fenced yard, bluestone patio, and the charm of a quiet cul-de-sac near parks and the lakefront. A half block from the highly coveted Hubbard Woods School, and only minutes from Metra, shops, restaurants, and Tower Beach, this meticulously maintained home offers luxury, comfort, and an unbeatable location in the heart of Hubbard Woods.

1159 Chatfield Road, Winnetka

$4,400,000

Set behind mature landscaping on a breathtaking and rarely available full acre, this extraordinary Winnetka residence offers the kind of space, privacy, and walk-to-everything convenience that almost never coexist. Thoughtfully reimagined through a complete gut renovation and expansion in 2010-including a new lower level, this 6-bedroom, 5.2-bath home lives beautifully for today while honoring timeless architectural character. Mornings begin in the sun-filled kitchen at the heart of the home, where everyday moments flow effortlessly into the expansive family room. French doors open to a screened porch w/ heated floors, perfect for summer dinners, morning coffee, and evenings overlooking the blue stone patio and yard. Gracious formal rooms set the stage for holidays and celebrations including the well appointed wet bar, while two private offices allow for quiet productivity and flexibility. An oversized mudroom makes busy days feel organized and easy. Upstairs, the primary suite is a true retreat: peaceful, private, and complete with a spa-like bath and generous dual walk-in closets. Three additional bedrooms and two full baths provide comfort and space for family and guests. The 2nd floor laundry is a work horse with dual washer and dryer plus sink, cabinets and counter space. The third floor offers incredible versatility with a large lofted flex space, two more bedrooms, and a full bath-ideal for teens, visitors, or au pair living. The finished lower level invites connection and recreation, featuring a spacious rec room, dedicated workout space, full bath, and abundant storage. Outside, the full acre becomes your private sanctuary; room to play, entertain, garden, or simply unwind beneath mature trees. All of this, just moments from downtown Winnetka, top-rated schools, parks, and the Metra. Expansive yet intimate. Private yet connected. A rare opportunity to enjoy estate-like grounds without sacrificing the ease of in-town living. Sellers require a fall closing.

6 Beds ⋅ 7 Baths ⋅ 12564836 MLS ⋅ CLOSED Status

Set behind mature landscaping on a breathtaking and rarely available full acre, this extraordinary Winnetka residence offers the kind of space, privacy, and walk-to-everything convenience that almost never coexist. Thoughtfully reimagined through a complete gut renovation and expansion in 2010-including a new lower level, this 6-bedroom, 5.2-bath home lives beautifully for today while honoring timeless architectural character. Mornings begin in the sun-filled kitchen at the heart of the home, where everyday moments flow effortlessly into the expansive family room. French doors open to a screened porch w/ heated floors, perfect for summer dinners, morning coffee, and evenings overlooking the blue stone patio and yard. Gracious formal rooms set the stage for holidays and celebrations including the well appointed wet bar, while two private offices allow for quiet productivity and flexibility. An oversized mudroom makes busy days feel organized and easy. Upstairs, the primary suite is a true retreat: peaceful, private, and complete with a spa-like bath and generous dual walk-in closets. Three additional bedrooms and two full baths provide comfort and space for family and guests. The 2nd floor laundry is a work horse with dual washer and dryer plus sink, cabinets and counter space. The third floor offers incredible versatility with a large lofted flex space, two more bedrooms, and a full bath-ideal for teens, visitors, or au pair living. The finished lower level invites connection and recreation, featuring a spacious rec room, dedicated workout space, full bath, and abundant storage. Outside, the full acre becomes your private sanctuary; room to play, entertain, garden, or simply unwind beneath mature trees. All of this, just moments from downtown Winnetka, top-rated schools, parks, and the Metra. Expansive yet intimate. Private yet connected. A rare opportunity to enjoy estate-like grounds without sacrificing the ease of in-town living. Sellers require a fall closing.

140 Birch Street, Winnetka

$625,000

Classic Gold Coast boutique building energy-but reimagined for Winnetka living, with western sunset views, a beautifully renovated interior, and that rare walk-to-everything lifestyle buyers chase for years. Tucked inside an intimate boutique building in one of Winnetka's most coveted locations, this stunning residence lives like the perfect blend of sophistication, comfort, and effortless luxury. From the moment you walk through the door, the natural light, sweeping treetop vistas, and polished finishes immediately set the tone. The expansive living room is anchored by a gas fireplace with custom built-ins and opens through sliding glass doors to a charming Juliette balcony where golden sunsets become part of your nightly routine. The dining space was designed for both entertaining and everyday living with a custom built-in hutch topped in quartz and seamless flow into the beautifully remodeled kitchen. Completely renovated in 2023, the kitchen delivers serious style with quartz countertops, soft-close Romar cabinetry, under-cabinet lighting, glossy aqua blue tile backsplash, and a full suite of Bosch stainless steel appliances. The primary suite feels like a private retreat with sliding glass doors to its own Juliette balcony, generous double closets plus a walk-in closet, and a spa-inspired bath featuring porcelain tile, quartz vanity, subway tile shower surround, dual shower sprays, niche detailing, and Toto fixtures. The second bedroom or den is equally inviting with balcony access, abundant natural light, and flexible living potential perfect for guests, office space, or cozy media room vibes. A beautifully updated second bath mirrors the same elevated design aesthetic found throughout the home. Additional highlights include a Miele stackable washer and dryer, Bryant furnace with Aprilaire humidifier, 150-amp electrical service, heated indoor parking, and exceptional convenience to the lake, Metra, parks, restaurants, and the heart of downtown Winnetka. This is the kind of home that feels impossible to replicate-timeless boutique luxury, turnkey renovation, mesmerizing sunset views, and an unbeatable location all wrapped into one extraordinary offering.

2 Beds ⋅ 2 Baths ⋅ 12659489 MLS ⋅ CLOSED Status

Classic Gold Coast boutique building energy-but reimagined for Winnetka living, with western sunset views, a beautifully renovated interior, and that rare walk-to-everything lifestyle buyers chase for years. Tucked inside an intimate boutique building in one of Winnetka's most coveted locations, this stunning residence lives like the perfect blend of sophistication, comfort, and effortless luxury. From the moment you walk through the door, the natural light, sweeping treetop vistas, and polished finishes immediately set the tone. The expansive living room is anchored by a gas fireplace with custom built-ins and opens through sliding glass doors to a charming Juliette balcony where golden sunsets become part of your nightly routine. The dining space was designed for both entertaining and everyday living with a custom built-in hutch topped in quartz and seamless flow into the beautifully remodeled kitchen. Completely renovated in 2023, the kitchen delivers serious style with quartz countertops, soft-close Romar cabinetry, under-cabinet lighting, glossy aqua blue tile backsplash, and a full suite of Bosch stainless steel appliances. The primary suite feels like a private retreat with sliding glass doors to its own Juliette balcony, generous double closets plus a walk-in closet, and a spa-inspired bath featuring porcelain tile, quartz vanity, subway tile shower surround, dual shower sprays, niche detailing, and Toto fixtures. The second bedroom or den is equally inviting with balcony access, abundant natural light, and flexible living potential perfect for guests, office space, or cozy media room vibes. A beautifully updated second bath mirrors the same elevated design aesthetic found throughout the home. Additional highlights include a Miele stackable washer and dryer, Bryant furnace with Aprilaire humidifier, 150-amp electrical service, heated indoor parking, and exceptional convenience to the lake, Metra, parks, restaurants, and the heart of downtown Winnetka. This is the kind of home that feels impossible to replicate-timeless boutique luxury, turnkey renovation, mesmerizing sunset views, and an unbeatable location all wrapped into one extraordinary offering.

680 Green Bay Road Unit #306, Winnetka

$1,750,000

4 Beds ⋅ 4 Baths ⋅ 12587281 MLS ⋅ CLOSED Status

211 Church Road, Winnetka

$1,105,813

Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond overlooking the lush grounds. The house presents a unique opportunity to upgrade by adding additional rooms on the unfinished second floor walk-up attic. The current square footage of the home is 2,316 which can be expanded to 6,805 sq. ft (per the Village of Winnetka.) That is also the floor area for new construction on this lot. Whether you want to renovate, flip, build new, or rent it, 1295 Sunview offers you a range of options!

2 Beds ⋅ 3 Baths ⋅ 12470735 MLS ⋅ CLOSED Status

Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond overlooking the lush grounds. The house presents a unique opportunity to upgrade by adding additional rooms on the unfinished second floor walk-up attic. The current square footage of the home is 2,316 which can be expanded to 6,805 sq. ft (per the Village of Winnetka.) That is also the floor area for new construction on this lot. Whether you want to renovate, flip, build new, or rent it, 1295 Sunview offers you a range of options!

1295 Sunview Lane, Winnetka

$1,100,000

Picture-perfect and move-in ready, this charming 3-bedroom, 1.1-bath home is nestled in one of Winnetka's most walkable locations. A welcoming, modern open floor plan flows from the foyer through the sun-drenched living room, surrounded by an abundance of windows and anchored by a wood-burning fireplace flanked by built-in bookcases. The chef's kitchen features solid white cabinetry, wood butcher-block countertops, and all-new stainless-steel LG appliances (2021). The main level also includes a formal dining room overlooking the fenced backyard, a completely remodeled four-season sunroom (2026), and an updated powder room (2025) with new floor tiles and fixtures. Upstairs, you'll find two guest bedrooms, a fully remodeled bathroom (2021), a large walk-in hallway closet, and a spacious primary suite with two separate closets. The finished lower level offers wonderful flex space for recreation and storage. Outside, enjoy a beautifully landscaped rear yard with a patio, plus a large front yard with a gracious half-circle driveway. Extensive updates throughout, including new Renewal by Andersen windows (2022), new composite siding (2025), new boiler, new exterior doors, structural improvements, and much more. Truly turnkey - just unpack and enjoy everything Winnetka has to offer!

3 Beds ⋅ 2 Baths ⋅ 12654472 MLS ⋅ CLOSED Status

Picture-perfect and move-in ready, this charming 3-bedroom, 1.1-bath home is nestled in one of Winnetka's most walkable locations. A welcoming, modern open floor plan flows from the foyer through the sun-drenched living room, surrounded by an abundance of windows and anchored by a wood-burning fireplace flanked by built-in bookcases. The chef's kitchen features solid white cabinetry, wood butcher-block countertops, and all-new stainless-steel LG appliances (2021). The main level also includes a formal dining room overlooking the fenced backyard, a completely remodeled four-season sunroom (2026), and an updated powder room (2025) with new floor tiles and fixtures. Upstairs, you'll find two guest bedrooms, a fully remodeled bathroom (2021), a large walk-in hallway closet, and a spacious primary suite with two separate closets. The finished lower level offers wonderful flex space for recreation and storage. Outside, enjoy a beautifully landscaped rear yard with a patio, plus a large front yard with a gracious half-circle driveway. Extensive updates throughout, including new Renewal by Andersen windows (2022), new composite siding (2025), new boiler, new exterior doors, structural improvements, and much more. Truly turnkey - just unpack and enjoy everything Winnetka has to offer!

259 Church Road, Winnetka

$1,380,000

Welcome to 373 Sunset Road, an spacious 5-bedroom, 3.1-bath brick and frame home in sought-after East Winnetka. Ideally located near Greeley Elementary, New Trier High School, the Indian Hill Metra, and just moments from Lake Michigan beaches, this home offers a wonderful blend of classic architecture and exceptional space. The gracious floor plan features a welcoming foyer, office/music room, formal dining room, and a large family room with fireplace and sliding doors to the patio and backyard. The galley-style kitchen opens to a light-filled breakfast room (currently used as a sitting room) overlooking the expansive yard (50 x 192) and in-ground pool. The second level includes a spacious primary suite with walk-in closet and large bath, along with three additional bedrooms a hall bath and a home office. The third floor offers flexible living with a sitting /office area and fifth bedroom space, and full bath-ideal for guests, work, or recreation. The unfinished lower level provides excellent storage in two storage rooms and future potential. Set on a lush, deep lot, the property features a large patio, pool, and sweeping green space-perfect for outdoor living and entertaining. A rare opportunity in one of Winnetka's most desirable locations.

5 Beds ⋅ 4 Baths ⋅ 12610110 MLS ⋅ CLOSED Status

Welcome to 373 Sunset Road, an spacious 5-bedroom, 3.1-bath brick and frame home in sought-after East Winnetka. Ideally located near Greeley Elementary, New Trier High School, the Indian Hill Metra, and just moments from Lake Michigan beaches, this home offers a wonderful blend of classic architecture and exceptional space. The gracious floor plan features a welcoming foyer, office/music room, formal dining room, and a large family room with fireplace and sliding doors to the patio and backyard. The galley-style kitchen opens to a light-filled breakfast room (currently used as a sitting room) overlooking the expansive yard (50 x 192) and in-ground pool. The second level includes a spacious primary suite with walk-in closet and large bath, along with three additional bedrooms a hall bath and a home office. The third floor offers flexible living with a sitting /office area and fifth bedroom space, and full bath-ideal for guests, work, or recreation. The unfinished lower level provides excellent storage in two storage rooms and future potential. Set on a lush, deep lot, the property features a large patio, pool, and sweeping green space-perfect for outdoor living and entertaining. A rare opportunity in one of Winnetka's most desirable locations.

373 Sunset Road, Winnetka

$2,300,000

Welcome to 870 Bryant Avenue, a stunning red brick Georgian just one block from Lake Michigan in the heart of East Winnetka. Originally built in 1919 and thoughtfully updated over time, this remarkable home beautifully blends timeless architecture with today's modern comforts, all while exuding character, warmth, and charm at every turn. Upon entry, you are greeted by a gracious foyer featuring a breathtaking curved staircase with wrought iron spindles, herringbone hardwood floors, and intricate dentil molding that immediately set the tone for the home's classic elegance. The oversized sunken living room is truly special - offering beautiful sightlines to the sunroom and bluestone patio beyond. French doors, custom built-ins, and a gorgeous original wood mantel create a warm and sophisticated gathering space equally suited for everyday living and entertaining. The sunroom, complete with newly installed hardwood floors, is a serene retreat overlooking lush landscaping, redesigned by Scott Byron, that feels like your own secret garden. French doors open to a new bluestone patio, creating effortless indoor-outdoor flow. The kitchen has been beautifully refreshed with a new island, marble countertops and backsplash, open shelving, and a new Wolf range and hood. The gorgeous dining room is ideal for entertaining, while the stylish first-floor powder room, complete with exquisite Iksel wallcovering, a custom white oak marble topped vanity, and Waterworks fixtures adds a sophisticated designer touch. The charming mudroom with marble tile floor offers both beauty and functionality. Upstairs, you'll find four beautifully designed bedrooms and three full bathrooms, including an oversized primary suite complete with a bright and sunny office or sitting room. All guest bathrooms have been thoughtfully renovated with marble flooring, Ann Sacks tile, custom vanities, and Perrin & Rowe fixtures. Convenient second-floor laundry completes the upper level. The lower level offers excellent storage space, and the attached garage adds everyday convenience. Extensive improvements have been made throughout the home, including a brand-new slate roof. This is a truly special opportunity to own a timeless East Winnetka home just moments from Lake Michigan, downtown Winnetka/ Hubbard Woods, parks, beaches, and train. Enjoy North Shore living at is best at 870 Bryant.

4 Beds ⋅ 4 Baths ⋅ 12661245 MLS ⋅ CLOSED Status

Welcome to 870 Bryant Avenue, a stunning red brick Georgian just one block from Lake Michigan in the heart of East Winnetka. Originally built in 1919 and thoughtfully updated over time, this remarkable home beautifully blends timeless architecture with today's modern comforts, all while exuding character, warmth, and charm at every turn. Upon entry, you are greeted by a gracious foyer featuring a breathtaking curved staircase with wrought iron spindles, herringbone hardwood floors, and intricate dentil molding that immediately set the tone for the home's classic elegance. The oversized sunken living room is truly special - offering beautiful sightlines to the sunroom and bluestone patio beyond. French doors, custom built-ins, and a gorgeous original wood mantel create a warm and sophisticated gathering space equally suited for everyday living and entertaining. The sunroom, complete with newly installed hardwood floors, is a serene retreat overlooking lush landscaping, redesigned by Scott Byron, that feels like your own secret garden. French doors open to a new bluestone patio, creating effortless indoor-outdoor flow. The kitchen has been beautifully refreshed with a new island, marble countertops and backsplash, open shelving, and a new Wolf range and hood. The gorgeous dining room is ideal for entertaining, while the stylish first-floor powder room, complete with exquisite Iksel wallcovering, a custom white oak marble topped vanity, and Waterworks fixtures adds a sophisticated designer touch. The charming mudroom with marble tile floor offers both beauty and functionality. Upstairs, you'll find four beautifully designed bedrooms and three full bathrooms, including an oversized primary suite complete with a bright and sunny office or sitting room. All guest bathrooms have been thoughtfully renovated with marble flooring, Ann Sacks tile, custom vanities, and Perrin & Rowe fixtures. Convenient second-floor laundry completes the upper level. The lower level offers excellent storage space, and the attached garage adds everyday convenience. Extensive improvements have been made throughout the home, including a brand-new slate roof. This is a truly special opportunity to own a timeless East Winnetka home just moments from Lake Michigan, downtown Winnetka/ Hubbard Woods, parks, beaches, and train. Enjoy North Shore living at is best at 870 Bryant.

870 Bryant Avenue, Winnetka

$1,700,000

5 Beds ⋅ 5 Baths ⋅ 12641226 MLS ⋅ CLOSED Status

1372 Sunview Lane, Winnetka

$1,350,000

Bright, spacious, and beautifully maintained, this charming home offers timeless character, gracious proportions, and an exceptional in-town location on a lush, deep lot with a gorgeous patio with thoughtfully designed seating wall - perfect for entertaining and outdoor enjoyment. High ceilings, classic architectural details, and abundant natural light create a warm and inviting atmosphere throughout. The gracious living room features handsome built-ins and a lovely bay window overlooking the picturesque front yard and sought-after neighborhood, just moments from town, train, parks, and K-8 schools. The formal dining room is beautifully proportioned for both everyday living and special gatherings, while the inviting den/family room opens seamlessly to the sunny south-facing backyard. The bright eat-in kitchen offers abundant cabinetry and prep space, generous table space, and delightful views of the beautifully landscaped yard. Upstairs, the spacious primary suite includes a large bedroom, private office or sitting room with beautiful views of the lush south yard, dressing area and an en suite bath. The third-floor retreat provides wonderful flexibility as a large 4th bedroom, playroom, office, or yoga studio. The finished lower level includes a recreation/playroom, additional 5th bedroom/office, full bath, and extensive storage. Freshly decorated and meticulously cared for throughout, this is an absolutely charming home in a vibrant neighborhood close to town, train, golf course, playfields, tennis center, and schools. A truly special offering.

4 Beds ⋅ 4 Baths ⋅ 12639601 MLS ⋅ CLOSED Status

Bright, spacious, and beautifully maintained, this charming home offers timeless character, gracious proportions, and an exceptional in-town location on a lush, deep lot with a gorgeous patio with thoughtfully designed seating wall - perfect for entertaining and outdoor enjoyment. High ceilings, classic architectural details, and abundant natural light create a warm and inviting atmosphere throughout. The gracious living room features handsome built-ins and a lovely bay window overlooking the picturesque front yard and sought-after neighborhood, just moments from town, train, parks, and K-8 schools. The formal dining room is beautifully proportioned for both everyday living and special gatherings, while the inviting den/family room opens seamlessly to the sunny south-facing backyard. The bright eat-in kitchen offers abundant cabinetry and prep space, generous table space, and delightful views of the beautifully landscaped yard. Upstairs, the spacious primary suite includes a large bedroom, private office or sitting room with beautiful views of the lush south yard, dressing area and an en suite bath. The third-floor retreat provides wonderful flexibility as a large 4th bedroom, playroom, office, or yoga studio. The finished lower level includes a recreation/playroom, additional 5th bedroom/office, full bath, and extensive storage. Freshly decorated and meticulously cared for throughout, this is an absolutely charming home in a vibrant neighborhood close to town, train, golf course, playfields, tennis center, and schools. A truly special offering.

972 Elm Street, Winnetka

$1,340,000

Welcome to this truly charming, picture-perfect home in an unbeatable walk-to-everything location. The beautifully designed first floor showcases an elegant living room with fireplace that flows effortlessly into the dining room, highlighted by stunning built-ins. The inviting family room-also featuring custom built-ins-is the perfect place to gather and opens seamlessly to a sleek, thoughtfully designed kitchen with a generous eating area, all leading to a private patio and lush backyard-ideal for both everyday living and memorable entertaining. Upstairs, the exceptional primary suite feels like a true retreat, with soaring ceilings, expansive space, and a lovely Juliette balcony overlooking the serene backyard. The spa-like en suite bath features a luxurious shower, handsome double vanity, private water closet and excellent storage. Two additional bedrooms each enjoy access to their own baths, while a beautifully designed coffee/wine bar with fridge and sink adds a sophisticated and indulgent touch. The bright and cheerful lower level offers a versatile workspace and playroom, a well-equipped laundry area, and outstanding storage, including a cedar closet. An attached one-car garage, along with an additional parking pad off the alley, provides convenience and flexibility. Impeccably maintained and thoughtfully updated throughout, this is a truly special home that effortlessly blends comfort, style, and functionality.

3 Beds ⋅ 4 Baths ⋅ 12631351 MLS ⋅ CLOSED Status

Welcome to this truly charming, picture-perfect home in an unbeatable walk-to-everything location. The beautifully designed first floor showcases an elegant living room with fireplace that flows effortlessly into the dining room, highlighted by stunning built-ins. The inviting family room-also featuring custom built-ins-is the perfect place to gather and opens seamlessly to a sleek, thoughtfully designed kitchen with a generous eating area, all leading to a private patio and lush backyard-ideal for both everyday living and memorable entertaining. Upstairs, the exceptional primary suite feels like a true retreat, with soaring ceilings, expansive space, and a lovely Juliette balcony overlooking the serene backyard. The spa-like en suite bath features a luxurious shower, handsome double vanity, private water closet and excellent storage. Two additional bedrooms each enjoy access to their own baths, while a beautifully designed coffee/wine bar with fridge and sink adds a sophisticated and indulgent touch. The bright and cheerful lower level offers a versatile workspace and playroom, a well-equipped laundry area, and outstanding storage, including a cedar closet. An attached one-car garage, along with an additional parking pad off the alley, provides convenience and flexibility. Impeccably maintained and thoughtfully updated throughout, this is a truly special home that effortlessly blends comfort, style, and functionality.

1105 Elm Street, Winnetka

$2,175,000

Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast area which flows seamlessly to the living areas of the home sets the stage for this finely designed and renovated home. We--designed custom built-ins are located throughout the home. Gracious formal living room with fireplace and dining room provide classic elegance, while the inviting family room, also with fireplace, flows easily from the kitchen and opens to a charming four-season sunroom/gazebo, creating the perfect connection to the pool, hot tub and backyard. A full bath with shower is located in this area, adding convenience for the pool. An inviting first-floor library with fireplace offers an ideal work-from-home space or a second family room/den. Everyday functionality is unmatched with a large mudroom and double laundry room with two washers and two dryers and a large counter for folding/organizing. The second floor includes 2 spacious ensuite bedrooms, one with additional flexible space which is perfect for a play or study area. A large walk-in attic provides tremendous storage and practical expansion potential if desired. The lower level is designed for recreation and relaxation with a media/game room with fireplace, an exercise room with high ceiling, and a private, versatile office space which is ideal for homework, crafts, or a gift-wrapping station. A separate unfinished basement offers tremendous storage and is conveniently access via a staircase from the kitchen. A second laundry area is located here. Set on an exceptional 110 x 200 landscaped lot, the outdoor spaces are truly special-featuring a pool, hot tub, expansive entertaining patio, and abundant green space for play. A conveniently located pool shed offers storage for pool furniture during the winter and the attached, heated two-car garage is an appreciated feature. Sunny raised garden beds with southern exposures offer the perfect spot for flowers, vegetables, and herbs. Privately set amid lush mature landscaping yet just minutes from town, train, schools, and everything Winnetka offers, this home combines timeless architecture with the feel of a private retreat on beautiful Hill Road.

4 Beds ⋅ 7 Baths ⋅ 12580255 MLS ⋅ CLOSED Status

Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast area which flows seamlessly to the living areas of the home sets the stage for this finely designed and renovated home. We--designed custom built-ins are located throughout the home. Gracious formal living room with fireplace and dining room provide classic elegance, while the inviting family room, also with fireplace, flows easily from the kitchen and opens to a charming four-season sunroom/gazebo, creating the perfect connection to the pool, hot tub and backyard. A full bath with shower is located in this area, adding convenience for the pool. An inviting first-floor library with fireplace offers an ideal work-from-home space or a second family room/den. Everyday functionality is unmatched with a large mudroom and double laundry room with two washers and two dryers and a large counter for folding/organizing. The second floor includes 2 spacious ensuite bedrooms, one with additional flexible space which is perfect for a play or study area. A large walk-in attic provides tremendous storage and practical expansion potential if desired. The lower level is designed for recreation and relaxation with a media/game room with fireplace, an exercise room with high ceiling, and a private, versatile office space which is ideal for homework, crafts, or a gift-wrapping station. A separate unfinished basement offers tremendous storage and is conveniently access via a staircase from the kitchen. A second laundry area is located here. Set on an exceptional 110 x 200 landscaped lot, the outdoor spaces are truly special-featuring a pool, hot tub, expansive entertaining patio, and abundant green space for play. A conveniently located pool shed offers storage for pool furniture during the winter and the attached, heated two-car garage is an appreciated feature. Sunny raised garden beds with southern exposures offer the perfect spot for flowers, vegetables, and herbs. Privately set amid lush mature landscaping yet just minutes from town, train, schools, and everything Winnetka offers, this home combines timeless architecture with the feel of a private retreat on beautiful Hill Road.

1185 Hill Road, Winnetka

$1,975,000

Welcome home to this beautiful east Winnetka home, where classic charm meets modern comfort and the design, ceiling heights, flow and quality is is exceptional. A gracious foyer (15 x 13) welcomes you and flows effortlessly into the inviting living room with gas fireplace and to the formal dining room - complete with a cozy window seat and timeless built-ins - the perfect setting for holiday celebrations and special meals. At the heart of the home, you'll find a stunning custom kitchen featuring beautiful cabinetry, high-end appliances, a spacious center island with extra storage, prep sink and island seating for 4. A large walk-in pantry adds to the convenience of this finely designed kitchen. The adjacent butler's pantry with wine fridge and abundant storage for glassware makes entertaining easy and elegant. The spacious, bright and airy family room overlooks the backyard and deck and creates a warm, connected space for gathering and relaxing. A thoughtfully designed mudroom keeps daily life beautifully organized. Upstairs, the serene and spacious primary suite feels like a private retreat, complete with its own entrance hall, large walk-in closet and generous hall closet, and a luxurious bath with custom cabinetry, double sinks and a beautiful shower. Three additional bedrooms and a renovated hall bath complete the second floor. The third floor offers wonderful flexibility with two more bedrooms (or office spaces) plus a renovated bath - perfect for guests, family or work-from-home needs. The excavated lower level provides a fantastic recreation/exercise area in the newer section under the addition and a cheery, inviting playroom, powder room, laundry, and abundant storage in the original basement. Outdoor living is just as special with a welcoming 19' x 11' front porch with ceiling fan and an expansive back deck which overlooks the fully fenced backyard (including gate at driveway), designed for relaxing evenings and effortless entertaining. South and west exposures are enjoyed in this sunny outdoor area. A 2 and 1/2-car garage adds even more convenience. All of this is located in an unbeatable location close to the train, parks, Lake Michigan, and town - truly the best of Winnetka living!

5 Beds ⋅ 5 Baths ⋅ 12572439 MLS ⋅ CLOSED Status

Welcome home to this beautiful east Winnetka home, where classic charm meets modern comfort and the design, ceiling heights, flow and quality is is exceptional. A gracious foyer (15 x 13) welcomes you and flows effortlessly into the inviting living room with gas fireplace and to the formal dining room - complete with a cozy window seat and timeless built-ins - the perfect setting for holiday celebrations and special meals. At the heart of the home, you'll find a stunning custom kitchen featuring beautiful cabinetry, high-end appliances, a spacious center island with extra storage, prep sink and island seating for 4. A large walk-in pantry adds to the convenience of this finely designed kitchen. The adjacent butler's pantry with wine fridge and abundant storage for glassware makes entertaining easy and elegant. The spacious, bright and airy family room overlooks the backyard and deck and creates a warm, connected space for gathering and relaxing. A thoughtfully designed mudroom keeps daily life beautifully organized. Upstairs, the serene and spacious primary suite feels like a private retreat, complete with its own entrance hall, large walk-in closet and generous hall closet, and a luxurious bath with custom cabinetry, double sinks and a beautiful shower. Three additional bedrooms and a renovated hall bath complete the second floor. The third floor offers wonderful flexibility with two more bedrooms (or office spaces) plus a renovated bath - perfect for guests, family or work-from-home needs. The excavated lower level provides a fantastic recreation/exercise area in the newer section under the addition and a cheery, inviting playroom, powder room, laundry, and abundant storage in the original basement. Outdoor living is just as special with a welcoming 19' x 11' front porch with ceiling fan and an expansive back deck which overlooks the fully fenced backyard (including gate at driveway), designed for relaxing evenings and effortless entertaining. South and west exposures are enjoyed in this sunny outdoor area. A 2 and 1/2-car garage adds even more convenience. All of this is located in an unbeatable location close to the train, parks, Lake Michigan, and town - truly the best of Winnetka living!

838 Lincoln Avenue, Winnetka

$2,550,000

Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96x160) with sweeping views of the Village Green. Architecturally significant and award-winning William Aiken classic restored and preserved to the modern standard, including a 2007 addition. Just a short walk to everything - town, train, beaches, school, and more - with your own private backyard garden oasis, this home offers a unique blend of timeless charm and contemporary luxury overlooking the iconic Village Green vistas. This classic architectural gem has been meticulously renovated and lovingly maintained to showcase architectural details, with every graciously scaled room beautifully appointed with breathtaking panoramic views. From the moment you enter the classic foyer with detailed millwork and soaring ceilings, the seamless flow of the home provides an ideal layout for everyday living and formal entertaining. The expansive living room features gorgeous built-in bookshelves, a beautiful wood-burning fireplace (overmantle designed by the homeowner), and glass French doors along every wall, offering incredible natural light and floor-to-ceiling Village Green views. Enjoy stunning vistas at any time of the year from either of the two 4-exposure sunrooms (one off LR and one off DR). A separate formal dining room, conveniently located with access to the kitchen, offers enough space for all of your entertaining needs, and opens to the second sunroom. The family room (2007) is a showstopper with vaulted ceilings and skylights, a handsome stone fireplace (gas), detailed built-in bookshelves, and oversized windows highlighting breathtaking views of the award-winning backyard. The bright kitchen with center island and wall-to-wall built-ins is perfectly positioned between the dining room, family room, and back hall mudroom. The gracious front hall staircase invites you upstairs to find the primary suite with bay window overlooking the gorgeous grounds, private bath, and walk-in closet. Two additional well-sized bedrooms share a Jack-and-Jill bath, as well as a hall bath with washer/dryer offering potential for a full second floor laundry room. Retreat up to the third floor with two bedrooms and a full bath - the ultimate treetop suite! The lower level offers a large finished recreation room that was dug out in 2007 while the expansive unfinished area has unlimited potential and endless possibilities. The backyard is a true private oasis - a sanctuary from the hustle and bustle of everyday life - offering serene tranquility and peaceful moments. Featuring bluestone terraces and limestone pathways, the backyard reveals a true secret garden with lush plantings, 3 waterfalls, a koi pond, and a bridge to the Japanese teahouse / gazebo. This home was thoughtfully renovated in 1989 and updated meticulously over the years, including an award-winning 2007 addition, 2003 detached garage, and updated Marvin windows. Experience elegance and comfort in an A+ location, just steps from town, train, schools, and Maple Beach!

5 Beds ⋅ 5 Baths ⋅ 12631320 MLS ⋅ CLOSED Status

Exceptional East Winnetka Georgian on serene and lush . 4-acre grounds (96x160) with sweeping views of the Village Green. Architecturally significant and award-winning William Aiken classic restored and preserved to the modern standard, including a 2007 addition. Just a short walk to everything - town, train, beaches, school, and more - with your own private backyard garden oasis, this home offers a unique blend of timeless charm and contemporary luxury overlooking the iconic Village Green vistas. This classic architectural gem has been meticulously renovated and lovingly maintained to showcase architectural details, with every graciously scaled room beautifully appointed with breathtaking panoramic views. From the moment you enter the classic foyer with detailed millwork and soaring ceilings, the seamless flow of the home provides an ideal layout for everyday living and formal entertaining. The expansive living room features gorgeous built-in bookshelves, a beautiful wood-burning fireplace (overmantle designed by the homeowner), and glass French doors along every wall, offering incredible natural light and floor-to-ceiling Village Green views. Enjoy stunning vistas at any time of the year from either of the two 4-exposure sunrooms (one off LR and one off DR). A separate formal dining room, conveniently located with access to the kitchen, offers enough space for all of your entertaining needs, and opens to the second sunroom. The family room (2007) is a showstopper with vaulted ceilings and skylights, a handsome stone fireplace (gas), detailed built-in bookshelves, and oversized windows highlighting breathtaking views of the award-winning backyard. The bright kitchen with center island and wall-to-wall built-ins is perfectly positioned between the dining room, family room, and back hall mudroom. The gracious front hall staircase invites you upstairs to find the primary suite with bay window overlooking the gorgeous grounds, private bath, and walk-in closet. Two additional well-sized bedrooms share a Jack-and-Jill bath, as well as a hall bath with washer/dryer offering potential for a full second floor laundry room. Retreat up to the third floor with two bedrooms and a full bath - the ultimate treetop suite! The lower level offers a large finished recreation room that was dug out in 2007 while the expansive unfinished area has unlimited potential and endless possibilities. The backyard is a true private oasis - a sanctuary from the hustle and bustle of everyday life - offering serene tranquility and peaceful moments. Featuring bluestone terraces and limestone pathways, the backyard reveals a true secret garden with lush plantings, 3 waterfalls, a koi pond, and a bridge to the Japanese teahouse / gazebo. This home was thoughtfully renovated in 1989 and updated meticulously over the years, including an award-winning 2007 addition, 2003 detached garage, and updated Marvin windows. Experience elegance and comfort in an A+ location, just steps from town, train, schools, and Maple Beach!

500 Maple Street, Winnetka

$1,550,000

SOLD BEFORE PROCESSING

3 Beds ⋅ 3 Baths ⋅ 12682032 MLS ⋅ CLOSED Status

SOLD BEFORE PROCESSING

812 Oak Street Unit #300, Winnetka

$3,525,000

4 Beds ⋅ 5 Baths ⋅ 12496129 MLS ⋅ CLOSED Status

Winnetka

$2,765,000

This extraordinary residence, originally dating to the 1920s and completely rebuilt in 2010-including a fully excavated lower level-offers an exceptional blend of timeless architectural character and refined modern luxury across four impeccably finished levels. Set on an expansive 75 x 187 lot, the stately brick exterior, enhanced by a handsome porte cochere, creates a memorable and elegant introduction to the home, hinting at the remarkable quality and thoughtful design found within. Every detail has been meticulously curated to deliver a home of extraordinary craftsmanship, scale, and sophistication. Rich custom millwork, beautifully crafted windows, bespoke cabinetry, exquisite stonework, and designer lighting are seamlessly integrated throughout, creating a cohesive and elevated aesthetic. The interior offers both grand, light-filled spaces ideal for entertaining and more intimate, comfortable areas designed for everyday living. The property itself is equally impressive, with lush, professionally landscaped grounds (designed by Red Spade Environments) fully irrigated by an in-ground sprinkler system. The outdoor living experience is truly exceptional, featuring a stunning patio with pergola that invites relaxed gatherings, as well as a second, more casual patio just off the kitchen and family room-perfect for effortless indoor-outdoor living. Adding to the charm and uniqueness of the setting is a charming brick garage with its own outdoor fireplace and patio, creating a warm and inviting retreat for entertaining or quiet, tranquil evenings at home. Perfectly positioned in a highly sought-after location, this home offers unparalleled convenience to top-rated schools, scenic parks, a nearby golf courses (18 hole and 9 hole par 3), tennis and paddle facilities, and the vibrant town center with its shops, dining, and train access. Combining architectural integrity, modern amenities, and an unbeatable location, this is a truly special offering that embodies both elegance and lifestyle at the highest level.

4 Beds ⋅ 6 Baths ⋅ 12608265 MLS ⋅ CLOSED Status

This extraordinary residence, originally dating to the 1920s and completely rebuilt in 2010-including a fully excavated lower level-offers an exceptional blend of timeless architectural character and refined modern luxury across four impeccably finished levels. Set on an expansive 75 x 187 lot, the stately brick exterior, enhanced by a handsome porte cochere, creates a memorable and elegant introduction to the home, hinting at the remarkable quality and thoughtful design found within. Every detail has been meticulously curated to deliver a home of extraordinary craftsmanship, scale, and sophistication. Rich custom millwork, beautifully crafted windows, bespoke cabinetry, exquisite stonework, and designer lighting are seamlessly integrated throughout, creating a cohesive and elevated aesthetic. The interior offers both grand, light-filled spaces ideal for entertaining and more intimate, comfortable areas designed for everyday living. The property itself is equally impressive, with lush, professionally landscaped grounds (designed by Red Spade Environments) fully irrigated by an in-ground sprinkler system. The outdoor living experience is truly exceptional, featuring a stunning patio with pergola that invites relaxed gatherings, as well as a second, more casual patio just off the kitchen and family room-perfect for effortless indoor-outdoor living. Adding to the charm and uniqueness of the setting is a charming brick garage with its own outdoor fireplace and patio, creating a warm and inviting retreat for entertaining or quiet, tranquil evenings at home. Perfectly positioned in a highly sought-after location, this home offers unparalleled convenience to top-rated schools, scenic parks, a nearby golf courses (18 hole and 9 hole par 3), tennis and paddle facilities, and the vibrant town center with its shops, dining, and train access. Combining architectural integrity, modern amenities, and an unbeatable location, this is a truly special offering that embodies both elegance and lifestyle at the highest level.

1241 Ash Street, Winnetka

$2,900,000

Welcome to this Margaret McCurry designed 5 bedroom, 6 bathroom home with a primary suite on the first floor and golf simulator and extensive lower level recreation area. Tucked off Indian Hill golf course on a special little lane, it's all here in this custom built home w/first floor primary bedroom with a spectacular floor plan and sliding doors that can define the rooms. One of a kind design by noted architect, Margaret McCurry of Tigerman McCurry. The welcoming front door entrance w/ pergola woven with wisteria opens into a double atrium foyer reception hallway w/soaring ceilings & double sided FP as the focal point. Once you enter the main space, there is a completely open floor plan, yet designated sun filled spaces. 11 ft ceilings, tons of built-ins, clean millwork, and oversized windows, highlight the quality of design. Primary suite on 1st floor with separate closets, a sitting room that open to private patios that showcase the exquisite landscaped .5 acre grounds. Oversized great room opens to family room, chefs kitchen, and separate breakfast room. Separate quarters on 2nd floor w/ 4 beds all w/ ensuite baths & second vaulted family room. Unexpected full lower level recreation space with golf simulator, wet bar golf viewing area, family room, exercise room and tool area with full bathroom. Huge mudroom/storage area and laundry on first floor w/ attached 4 car garage. Step outside to beautifully manicured landscaping w/the most stunning gardens & grounds finished with that classic white fence. Meticulously taken care of as this house is in pristine condition. Set on an exclusive part of Indian Hill closer to town, train and schools. As the architect quotes "4 Indian Hill is all about easy casual living with understated artistic beauty." This home lives so well in a sought after private location.

5 Beds ⋅ 7 Baths ⋅ 12549096 MLS ⋅ CLOSED Status

Welcome to this Margaret McCurry designed 5 bedroom, 6 bathroom home with a primary suite on the first floor and golf simulator and extensive lower level recreation area. Tucked off Indian Hill golf course on a special little lane, it's all here in this custom built home w/first floor primary bedroom with a spectacular floor plan and sliding doors that can define the rooms. One of a kind design by noted architect, Margaret McCurry of Tigerman McCurry. The welcoming front door entrance w/ pergola woven with wisteria opens into a double atrium foyer reception hallway w/soaring ceilings & double sided FP as the focal point. Once you enter the main space, there is a completely open floor plan, yet designated sun filled spaces. 11 ft ceilings, tons of built-ins, clean millwork, and oversized windows, highlight the quality of design. Primary suite on 1st floor with separate closets, a sitting room that open to private patios that showcase the exquisite landscaped .5 acre grounds. Oversized great room opens to family room, chefs kitchen, and separate breakfast room. Separate quarters on 2nd floor w/ 4 beds all w/ ensuite baths & second vaulted family room. Unexpected full lower level recreation space with golf simulator, wet bar golf viewing area, family room, exercise room and tool area with full bathroom. Huge mudroom/storage area and laundry on first floor w/ attached 4 car garage. Step outside to beautifully manicured landscaping w/the most stunning gardens & grounds finished with that classic white fence. Meticulously taken care of as this house is in pristine condition. Set on an exclusive part of Indian Hill closer to town, train and schools. As the architect quotes "4 Indian Hill is all about easy casual living with understated artistic beauty." This home lives so well in a sought after private location.

4 Indian Hill Road, Winnetka

$2,755,000

Classic cedar shake Colonial on an exceptional 100-foot-wide lot in East Winnetka, just moments from the train, schools, beaches and town. Thoughtfully renovated with a fresh coastal aesthetic, this light-filled home beautifully blends timeless architectural detail and old-world craftsmanship with today's airy, modern style. A welcoming foyer opens to a gracious living room with hardwood floors, gas fireplace, and a charming covered porch-perfect for morning coffee or evening gatherings. The elegant dining room features recessed lighting, refined millwork, sweeping views of the professionally landscaped grounds and tiered brick terrace, and a built-in bar designed for seamless entertaining. The beautifully renovated kitchen blends style and function with high-end appliances, custom cabinetry, quartz countertops, a coffee bar, oversized island with seating, and a sunlit breakfast area ideal for gathering and entertaining. The inviting family room radiates warmth and character, featuring custom built-ins, a striking beamed ceiling, and expansive glass doors that seamlessly connect the indoors to the outdoors. The tranquil primary suite features a private sitting room and master bath. The second floor also includes three additional family bedrooms and two full baths. The third floor has been transformed into an exceptional space - the perfect versatile area for play, sleep, or work. The finished lower level offers outstanding living space with a recreation room, exercise room, bar area, laundry, half bath, and ample storage. Completing the package is an oversized 2.5-car custom garage with additional storage. A rare opportunity to own a beautifully updated home in one of East Winnetka's most desirable central locations.

4 Beds ⋅ 5 Baths ⋅ 12645391 MLS ⋅ CLOSED Status

Classic cedar shake Colonial on an exceptional 100-foot-wide lot in East Winnetka, just moments from the train, schools, beaches and town. Thoughtfully renovated with a fresh coastal aesthetic, this light-filled home beautifully blends timeless architectural detail and old-world craftsmanship with today's airy, modern style. A welcoming foyer opens to a gracious living room with hardwood floors, gas fireplace, and a charming covered porch-perfect for morning coffee or evening gatherings. The elegant dining room features recessed lighting, refined millwork, sweeping views of the professionally landscaped grounds and tiered brick terrace, and a built-in bar designed for seamless entertaining. The beautifully renovated kitchen blends style and function with high-end appliances, custom cabinetry, quartz countertops, a coffee bar, oversized island with seating, and a sunlit breakfast area ideal for gathering and entertaining. The inviting family room radiates warmth and character, featuring custom built-ins, a striking beamed ceiling, and expansive glass doors that seamlessly connect the indoors to the outdoors. The tranquil primary suite features a private sitting room and master bath. The second floor also includes three additional family bedrooms and two full baths. The third floor has been transformed into an exceptional space - the perfect versatile area for play, sleep, or work. The finished lower level offers outstanding living space with a recreation room, exercise room, bar area, laundry, half bath, and ample storage. Completing the package is an oversized 2.5-car custom garage with additional storage. A rare opportunity to own a beautifully updated home in one of East Winnetka's most desirable central locations.

747 Lincoln Avenue, Winnetka

$2,100,000

4 Beds ⋅ 4 Baths ⋅ 12628467 MLS ⋅ CLOSED Status

1082 Ash Street, Winnetka

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