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688 Greenbay Road Unit #302, Winnetka
$2,450,000
3 Beds ⋅ 3 Baths ⋅ 12762605 MLS ⋅ CLOSED Status
We are pleased to offer sophisticated buyers an exclusive maintenance-free lifestyle in one of the most coveted communities in the country. Designed by award winning RM Swanson Architects, The Walden will embrace the aesthetic charm of the North Shore and provide an urban experience in a dynamic, but casual setting. The historic business district and train station are within easy walking distance providing numerous options for shopping, dining and access to Ravinia as well as the Chicago Loop. The Walden will offer generous sized floorplans with 10ft ceilings and large transom windows to allow natural light to flood the open space. Interior finishes will be of the highest quality while still preserving the opportunity for customization to meet the personal needs and taste of the buyer. Each unit will include two terraces, two parking spaces in a heated underground garage with bike racks and separate dedicated storage rooms. This beautiful boutique building is a "once in a lifetime" opportunity and is not to be missed!

688 Greenbay Road Unit #302, Winnetka

1015 Sheridan Road, Winnetka
$3,400,000
6 Beds ⋅ 8 Baths ⋅ 12660928 MLS ⋅ CLOSED Status
Nestled on a private lane east of Sheridan Road, this distinguished Winnetka residence offers privacy, scale, quality craftsmanship, and exceptional everyday livability in one of the North Shore's most coveted east-side locations. Designed for elegant entertaining, multigenerational living, work-from-home flexibility, and relaxed daily comfort, the home features 6+ bedrooms, including a private in-law/guest suite with kitchen, 7.1 baths, expansive gathering spaces, an outdoor pool and spa, home theater, exercise room, and beautifully landscaped grounds. A sunlit two-story foyer with a sweeping bridal staircase creates a memorable first impression, opening to gracious formal living and dining rooms, a richly appointed library/home office, and a dramatic great room with coffered ceilings and wet bar. The chef's kitchen is beautifully equipped for everyday meals, holiday hosting, and large-scale entertaining, with a substantial center island, white cabinetry, professional gas range, double wall ovens, two dishwashers, full-size refrigerator and freezer, beverage refrigerator, and built-in microwave. Just beyond the kitchen, a comfortable fireside family room offers space for casual dining and opens to a lovely patio overlooking the private, professionally landscaped setting. A large mudroom with a full bath provides practical convenience and easy access for pool and spa use. Upstairs, the serene primary suite features three walk-in closets and a luxurious bath with steam shower and generous vanity space. The second level also includes two additional en-suite bedrooms, a full guest/in-law suite with kitchen, two more bedrooms, a hall bath, and a skylit laundry room - offering exceptional flexibility for guests, extended stays, private living space, or household support. The finished lower level expands the home's lifestyle appeal with a home theater, game room, exercise room/gym, bedroom with full bath, bonus room, and abundant storage. Additional amenities include: heated garage, heated driveway, sprinkler system, exterior lighting, and manicured professional landscaping. Located within the sought-after New Trier High School district and near beloved Hubbard Woods amenities, this private east Winnetka estate offers space, sophistication, resort-style amenities, and close proximity to Lake Michigan, beaches, parks, shopping, dining, and transportation - an extraordinary opportunity in one of Winnetka's most desirable locations. Property is being offered AS IS.

1015 Sheridan Road, Winnetka

688 Greenbay Road Unit #101, Winnetka
$1,599,000
3 Beds ⋅ 3 Baths ⋅ 12762576 MLS ⋅ CLOSED Status
We are pleased to offer sophisticated buyers an exclusive maintenance-free lifestyle in one of the most coveted communities in the country. Designed by award winning RM Swanson Architects, The Walden will embrace the aesthetic charm of the North Shore and provide an urban experience in a dynamic, but casual setting. The historic business district and train station are within easy walking distance providing numerous options for shopping, dining and access to Ravinia as well as the Chicago Loop. The Walden will offer generous sized floorplans with 10ft ceilings and large transom windows to allow natural light to flood the open space. Interior finishes will be of the highest quality while still preserving the opportunity for customization to meet the personal needs and taste of the buyer. Each unit will include two terraces, two parking spaces in a heated underground garage with bike racks and separate dedicated storage rooms. This beautiful boutique building is a "once in a lifetime" opportunity and is not to be missed!

688 Greenbay Road Unit #101, Winnetka

688 Greenbay Road Unit #201, Winnetka
$1,625,000
3 Beds ⋅ 3 Baths ⋅ 12762618 MLS ⋅ CLOSED Status
We are pleased to offer sophisticated buyers an exclusive maintenance-free lifestyle in one of the most coveted communities in the country. Designed by award winning RM Swanson Architects, The Walden will embrace the aesthetic charm of the North Shore and provide an urban experience in a dynamic, but casual setting. The historic business district and train station are within easy walking distance providing numerous options for shopping, dining and access to Ravinia as well as the Chicago Loop. The Walden will offer generous sized floorplans with 10ft ceilings and large transom windows to allow natural light to flood the open space. Interior finishes will be of the highest quality while still preserving the opportunity for customization to meet the personal needs and taste of the buyer. Each unit will include two terraces, two parking spaces in a heated underground garage with bike racks and separate dedicated storage rooms. This beautiful boutique building is a "once in a lifetime" opportunity and is not to be missed!

688 Greenbay Road Unit #201, Winnetka

1062 Ash Street, Winnetka
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 12039823 MLS ⋅ CLOSED Status
Beautiful, classic Winnetka home in meticulous condition with gorgeous renovations! The sunny first floor features large rooms that flow perfectly - including a fabulous dining room for entertaining. The renovated kitchen offers exquisite finishes including Italian quartzite counters, custom cabinets and professional appliances, all opening to spacious eating area and family room addition. The screened porch is perfect for entertaining and relaxing and opens to the lush, private, deep backyard. The second floor offers 4 bedrooms including a serene primary suite addition with gorgeous primary marble bath (renovated in 2025), 3 large secondary bedrooms and a classic hall bath, also renovated with classic marble tiles and finishes. The lower level includes a wine tasting/bar area with entertaining prep-'kitchen', private office, large rec room (this was added when the three story addition was completed), laundry, storage and full bath. The outdoor oasis is exceptional! Patio and deck, lush plantings, in-ground sprinkler system and privacy green screening with mature trees which envelope the property and lead to the newer two+ heated car garage - built with utmost quality and foresight for future needs and with easy alley access - all which complement the architecture of this true gem of a home in the heart of Winnetka near Schools (easy walk K-8), town, train and parks. Turn-key condition in a 10+ location!

1062 Ash Street, Winnetka

1347 Sunview Lane, Winnetka
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 12688534 MLS ⋅ CLOSED Status
Set on a professionally landscaped half-acre in the coveted Hubbard Woods School District, this exceptional 4-bedroom, 3.1-bath home offers expansive living spaces, refined finishes, and an effortless floor plan. A gracious foyer opens to an elegant circular layout featuring a sun-filled living room anchored by a striking fireplace, a handsome private office overlooking the landscaped grounds, and a sophisticated dining room with doors opening to the bluestone patio. The inviting family room enjoys picturesque views of the garden-like front lawn and flows seamlessly into the expansive eat-in kitchen, complete with a generous island, high-end appliances, and sweeping views of the lush backyard. A butler's pantry, spacious mudroom, and attached two-car garage complete the thoughtfully designed main level. Upstairs, two luxurious primary suites are complemented by two oversized secondary bedrooms, abundant closet space, and exceptional flexibility. The finished lower level offers a spacious recreation room, dedicated craft studio, and extensive storage. Walk to schools, town, tennis courts and the Winnetka Golf Course!

1347 Sunview Lane, Winnetka

1208 Oak Street, Winnetka
$1,226,000
3 Beds ⋅ 2 Baths ⋅ 12604512 MLS ⋅ CLOSED Status
Nestled in the heart of Winnetka's coveted " TREE STREETS" neighborhood sits the storybook home you've been waiting for. This special home is a sun-filled Mediterranean villa with an effortless blend of timeless architecture and a fresh, coastal-inspired aesthetic throughout. The home showcases airy interiors, soft neutral tones, and a well appointed floor plan that perfectly suits today's lifestyle. The great room has soaring ceilings, white washed wood beams, windows overlooking the park and a cozy gas fireplace. The bright white kitchen has high end appliances and beautiful marble countertops. The dining room is conveniently located adjacent to the kitchen. The first floor primary suite was recently expanded to create a spacious beautiful space. Equipped with a spa-like bathroom and large walk-in closet. The second floor has a bright landing desk/reading area, two large bedrooms connected by a beautiful bathroom, as well as a sun-filled bonus tandem room overlooking the gorgeous yard. The finished basement is currently being used as a music room but can easily be whatever you desire for the space. The tranquil oversized backyard is a peaceful place to retreat. Lush and green with a large bluestone patio, fire-pit and grill area, all with perfect views of the Fourth of July fireworks! Enjoy easy living with the premier walk-to location-just steps to award winning schools K-8, tennis, paddle, golf, sports fields, town + train and a short walk to the beach. Drop your bags & enjoy!!

1208 Oak Street, Winnetka

920 Pine Tree Lane, Winnetka
$2,400,000
5 Beds ⋅ 6 Baths ⋅ 12674124 MLS ⋅ CLOSED Status
Easy living at its best! Discerning updates and renovations combine with impeccable maintenance to create this exceptional home with the ease of one-floor living with outstanding design, gracious proportions, and an effortless flow throughout. Set on a gorgeous 4/10 acre property, the grounds are a true private retreat, featuring lush, professional landscaping, mature trees, colorful plantings, expansive lawns, elegant patio and front entrance, and thoughtfully designed landscape lighting that creates a magical setting day and night. A welcoming foyer introduces the inviting interior, where sun-filled living spaces are perfectly suited for both everyday living and entertaining. The spacious living room, elegant dining room, gourmet kitchen, and large family room blend seamlessly together, creating an ideal layout for today's lifestyle. The home offers five+ generously sized bedrooms including a luxurious primary suite that serves as a peaceful sanctuary and 4 additional bedrooms (3 are ensuite). The spa-inspired primary bath features heated floors and refined finishes, creating the perfect place to prepare for the day or to unwind at night. The finished lower level adds exceptional versatility with two spacious recreation and living areas, an exercise area, office/bedroom, full bath and abundant storage. A spacious, bright mudroom is accessed from the heated attached garage (with epoxy floor), and the adjacent laundry room provides everyday convenience and functionality. Originally renovated in 2001 and thoughtfully enhanced with significant updates in 2010 and then a fabulous renovation/updates in 2022, this home combines a fresh, current aesthetic with modern comfort. An extraordinary opportunity to enjoy easy, elegant living in one of the area's most beautiful and sought-after neighborhoods.

920 Pine Tree Lane, Winnetka

419 Provident Avenue, Winnetka
$1,355,000
3 Beds ⋅ 3 Baths ⋅ 12711054 MLS ⋅ CLOSED Status
Winnetka "tree streets" gem! This fully updated home blends classic exterior charm with a modern, open layout! Featuring three bedrooms, two and a half baths, a gorgeous kitchen and a beautiful backyard. Huge living room anchored by pretty fireplace flows seamlessly into open newer white kitchen and dining area. Family room - located just off the kitchen - opens to a fully fenced backyard with nice paver patio - and separate patio for grilling. Thoughtful mudroom area, powder room, and entry round out the first floor. The second floor features a large primary suite with two closets and a renovated primary bath. Two more family bedrooms share updated hall bath. Full basement with finished recreation room, laundry room, and huge storage room. Pull down stair attic has tons of additional storage or potential for future expansion. Deep, fully fenced yard with patio provides the perfect retreat. Detached two car garage with built in shelves. Unbeatable location: walk to top-rated schools, the Winnetka train, and all downtown Winnetka has to offer!

419 Provident Avenue, Winnetka

48 Indian Hill Road, Winnetka
$3,489,000
5 Beds ⋅ 5 Baths ⋅ 12682485 MLS ⋅ CLOSED Status
Tucked away in one of Winnetka's most coveted private roads, this exceptional 5-bedroom, 4.5-bathroom estate offers a prime spacious lot surrounded by majestic, mature trees. The property boasts an extraordinary setting that guarantees ultimate privacy while maximizing its unique geographic advantage. The home features dramatic, unobstructed vistas overlooking the historic Indian Hill Golf Course to the south and west, providing a picturesque backdrop of rolling fairways and breathtaking sunset views. Inside, the residence features large, sun-drenched rooms designed for both seamless grand-scale entertaining and comfortable family life. The expansive main living spaces are anchored by large windows that frame the lush greenery, effortlessly bringing the outdoors in. With five generous bedrooms and four and a half baths, the layout offers incredible flexibility for a primary suite retreat, dedicated home offices, or guest accommodation. This is a rare opportunity to own a private oasis with a world-class view in a premier Winnetka location.

48 Indian Hill Road, Winnetka

1050 Spruce Street, Winnetka
$2,750,000
4 Beds ⋅ 6 Baths ⋅ 12690581 MLS ⋅ CLOSED Status
Winnetka! This checks all of the boxes! 5 Beds/5.1 Baths. This gorgeous SFH comes with all of the perks. Gourmet kitchen with Sub-Zero/Thermador, large island, walk-in pantry and gorgeous breakfast area that opens to the family room. The first floor office has built-ins and French doors. Step into the formal dining room with beautiful ceiling details and moldings. Relax in the formal living room in front of the fireplace. Incredible primary suite with large his-and-her closets, and luxurious bath. The second floor has 2 additional ensuite bedrooms and a nicely appointed laundry room. The 3rd floor is light-filled and offers a 4th ensuite bedroom. The fantastic lower level has it all: a huge recreation room, 5th bedroom, exercise/theatre room, wine room, golf simulator, and the 5th full bath. Great location near schools, tennis, golf, playfields, and the train. Experience everything Winnetka has to offer.

1050 Spruce Street, Winnetka

127 Glenwood Avenue, Winnetka
$2,470,000
5 Beds ⋅ 5 Baths ⋅ 12677019 MLS ⋅ CLOSED Status
Nestled in one of the most sought-after and convenient locations in Winnetka/Hubbard Woods, this exceptional stone residence blends timeless architecture, refined design, and modern comfort just moments from town, the train, and Lake Michigan. Expertly crafted in 2006 by Adamczyk Fine Homes and Interiors, the home showcases nearly 7,000 square feet of beautifully designed living space across three finished levels. A grand foyer with a stunning custom staircase welcomes you into elegant, light-filled interiors, including a gracious living room with fireplace and a richly paneled private office. Designed for both everyday living and sophisticated entertaining, the formal dining room features its own fireplace and an adjoining butler's pantry complete with wine and beverage refrigerators. At the heart of the home is a family friendly gourmet kitchen with an island, abundant workspace, and a sunny breakfast area that opens seamlessly to the inviting family room. Custom built-ins, a fireplace, and French doors create a warm and comfortable setting while offering effortless access to the bluestone patio and expansive fenced backyard. The thoughtfully designed mudroom and laundry area provide everyday functionality with direct access to the attached two-car garage. Upstairs, the luxurious primary suite serves as a private retreat with a spacious bath and dual walk-in closets. Four additional generously sized bedrooms provide flexibility for family and guests, including a versatile fifth bedroom that can easily function as a sitting room, office, or exceptional dressing room extension to the primary suite. Two additional full baths complete the second level. The impressive lower level offers high ceilings, natural daylight windows and exceptional versatility, featuring a stone wine room, multiple recreation spaces, a sixth bedroom with full bath, exercise room, and storage. Outside, beautifully landscaped grounds create a serene and private setting that complements the home's elegant character. With exceptional craftsmanship, quality materials, a flowing floor plan, and timeless appeal, this remarkable property offers luxurious living designed for generations to enjoy. *Some photos virtually staged* Recent updates include a new Brava synthetic composite roof (2022), two new air conditioning systems (2022 & 2020), and a new furnace (2023).

127 Glenwood Avenue, Winnetka

566 Willow Road, Winnetka
$3,510,000
5 Beds ⋅ 7 Baths ⋅ 12712818 MLS ⋅ CLOSED Status
Perfectly positioned in coveted East Winnetka, this exquisite newer-construction stone residence offers timeless elegance, thoughtful design, and over 6,500 square feet of luxurious living across four beautifully finished levels. Upon entering the home, you can almost feel the lake breeze and catch a sight line of Lake Michigan-a reminder of this home's premier location just moments from the shoreline. The stately limestone and stone exterior, crowned by a classic slate roof, creates an unforgettable first impression. Inside, a grand reception foyer welcomes you with soaring ceilings, abundant natural light, and beautifully proportioned living spaces that exude warmth and sophistication. The gracious formal living room, anchored by a handsome limestone fireplace, flows seamlessly into an elegant dining room designed for memorable gatherings. Tucked away for privacy, a richly paneled office with custom built-in bookcases provides the perfect work-from-home retreat or quiet library. At the heart of the home, the expansive family room overlooks the backyard and sports court, creating an effortless connection between indoor and outdoor living. The New Chef's Kitchen offers a generous center island with seating, premium appliances, coffee station and breakfast bar, and a sun-filled breakfast room wrapped in windows that feels like a year-round solarium. A newly added mudroom with custom cubbies and storage provides convenient access to the attached heated garage with epoxy flooring. The second floor offers a beautifully designed center hall layout with new laundry room, four spacious bedrooms, including an exquisite primary suite that serves as a private sanctuary. Complete with dual walk-in closets and a serene spa bath, the suite is designed for ultimate comfort and relaxation. Three additional bedrooms, including two with en-suite baths, provide exceptional accommodations for family and guests. The third floor is a destination all its own-a versatile retreat featuring a spacious bedroom suite, full bath, and a private rooftop sun deck. The fully finished lower level expands the home's exceptional living space with a large recreation room, custom bar, sixth bedroom, and full bath-ideal for overnight guests, a bonus room - ideal for a gym, or extended family living. Outside, the deep and fully fenced backyard is an entertainer's dream. A generous patio invites al fresco dining and summer gatherings, while the sports court provides endless opportunities for recreation and play. All of this is set on one of East Winnetka's most desirable blocks, offering an unbeatable lifestyle just moments from downtown Winnetka, the lakefront, parks, train, and award-winning Greeley Elementary and New Trier High School.

566 Willow Road, Winnetka

757 Locust Street, Winnetka
$2,195,000
6 Beds ⋅ 6 Baths ⋅ 12700587 MLS ⋅ CLOSED Status
757 Locust is a stunning 6-bedroom, 4.2-bath home set on a 15,000-square-foot lot in the heart of Hubbard Woods. Built in 1920 and thoughtfully updated over the years, this exceptional residence blends timeless architecture with modern comfort, with large, light-filled rooms, soaring ceilings, and oversized windows that create a sense of space throughout. A bluestone walkway leads to a gracious foyer that opens to an oversized living room anchored by a wood-burning fireplace, creating a warm and sophisticated space perfect for both everyday living and entertaining. The well-proportioned dining room flows seamlessly between the living room and kitchen, making gatherings effortless. The updated kitchen features newer appliances and opens to a sun-filled breakfast room where two walls of windows open wide, beautifully blurring the line between indoors and out. Just off the kitchen, the family room is perfectly positioned with built-ins and a second fireplace, and opens to a deck and patio overlooking the expansive backyard, with a mudroom connecting directly to both. Upstairs, the generous primary suite is a true retreat featuring a beautifully appointed bath with dual vanity, heated marble floors, and a walk-in closet. Four additional bedrooms, one with an en-suite bath, and a hall bath complete the second floor. The third-floor addition by Paul Konstant offers a sixth bedroom, a full bath, and a charming hangout space with treetop views of Locust Street, while the lower level provides room for play and abundant storage. This home has been extensively and thoughtfully updated, with recent improvements including two new AC condensers (2026), a new AC air handler (2026), an EV charging port (2025), a new composite synthetic cedar roof (2024), fresh exterior paint (2024), replaced water service (2023), new sump pumps (2023), and a new boiler/hot water heater by American Vintage Home. The heated, attached, oversized garage adds everyday convenience year-round. A truly special opportunity to own a timeless home just moments from Lake Michigan, the Hubbard Woods and Elm Street shopping districts, top-rated schools, parks, beaches, and the train.

757 Locust Street, Winnetka

605 Arbor Vitae Road, Winnetka
$4,300,000
7 Beds ⋅ 6 Baths ⋅ 12680669 MLS ⋅ CLOSED Status
A RARE OPPORTUNITY...in the HEART of East Winnetka, this iconic home is among the Village's most admired residences! Commanding an elevated setting atop Arbor Vitae, the magnificent home was designed by renowned architects Otis & Clark and has earned its grand reputation as Winnetka's own "Castle on the Hill." It boasts one of the most exceptional backyard retreats! Featured in Luxe Magazine and showcased on the prestigious Winnetka Community Housewalk, the home underwent an extraordinary renovation that seamlessly marries historic grandeur with today's most coveted luxury amenities. Every detail has been thoughtfully reimagined while preserving the architectural integrity, craftsmanship and timeless elegance. A breathtaking barrel-vaulted reception gallery sets an unforgettable first impression, creating a dramatic backdrop for art collections, entertaining and everyday living. The home boasts a ton of natural light, soaring ceilings and fabulous millwork. At the heart of the home, a spectacular skylit atrium-style great room offering panoramic views of the sprawling grounds and resort-caliber outdoor living spaces: newly renovated pool, patio, built-in fire pit area and an incredible professionally landscaped backyard. A wall of French doors on the back of the home blends the indoor and outdoor living seamlessly. The designer kitchen is both beautiful and functional, featuring a coveted La Cornue range, Sub-Zero, Miele appliances, custom cabinetry, radiant heated floors and Waterworks fixtures. You will love entertaining in the elegant dining room, sophisticated den with custom bar to the inviting family room anchored by a new fireplace and bespoke built-ins. The luxurious primary suite is a private sanctuary designed for relaxation and renewal. The spa-inspired bath showcases heated marble floors, a steam shower, freestanding soaking tub, Waterworks fixtures and an extraordinary custom dressing room. A private sitting room and office complete the primary suite. Additional renovations include beautifully appointed en-suite baths and a reimagined third floor with hang out, office and workout spaces...use it however you like! Outside, the grounds rival those of a private resort. The expansive, park-like backyard features a stunning renovated swimming pool, multiple entertaining terraces, fire pit, and professionally designed landscaping that provides beauty, privacy, and year-round enjoyment. Easy access to a pool/changing area as well. This home is in an A+ location! Minutes from the Beach, steps from downtown Winnetka shops and restaurants, award winning schools, parks, and the train. This extraordinary family home offers a once-in-a-generation opportunity to own one of Winnetka's true architectural treasures!!

605 Arbor Vitae Road, Winnetka

882 Willow Road, Winnetka
$999,000
4 Beds ⋅ 4 Baths ⋅ 12617031 MLS ⋅ CLOSED Status
Prepare to be captivated by this picture-perfect 4-bedroom, 3.1-bathroom colonial-cottage home, meticulously updated with high-end designer finishes throughout. Boasting incredible curb appeal with its deep blue siding, crisp white trim, and brick-paver paths, this turn-key residence seamlessly blends historic architectural character with contemporary luxury. Inside, an airy, light-filled layout features pristine hardwood flooring, clean architectural lines, and an adaptable floor plan. The heart of the home is the stunning new kitchen, showcasing custom sage-green shaker cabinetry, durable stone countertops, a timeless white farmhouse sink, and high-efficiency stainless steel appliances. The kitchen overlooks the rear living space, where sliding glass doors offer a clear view and effortless access to the private rear entertainment deck. The upper levels house a spectacular primary retreat, designed as a private sanctuary. The primary bathroom offers a true spa experience with its freestanding soaking tub, walk-in shower, expansive double vanity, and a massive skylight overhead. The remaining three bedrooms feature charming sloped cottage ceilings, bright windows, and classic millwork. A second beautifully renovated hall bath showcases a sophisticated, moody color palette, a premium marble vanity, and an integrated skylight. Additional living and recreation space awaits in the finished lower level, anchored by a cozy electric fireplace is ideal for a family room, home theater, or private office. The laundry room, a wine closet, an enormous storage room, third fill bathroom and a craft room round out the flexible basement level. Outside, enjoy a detached 1-car garage and low-maintenance landscaping. Nestled in a premier neighborhood, this home offers unparalleled convenience with its close proximity to town, the train, and local schools. A masterful combination of sophisticated design and everyday functionality!

882 Willow Road, Winnetka

154 Glenwood Avenue, Winnetka
$1,230,154
3 Beds ⋅ 2 Baths ⋅ 12697250 MLS ⋅ CLOSED Status
Rare opportunity in East Winnetka. Nestled beside a quiet neighborhood park, this beautifully updated 1919 Tudor blends timeless architectural character with thoughtful modern updates in one of Winnetka's most sought-after locations. A scenic path just behind the home provides easy access to the Green Bay Trail, making it an easy walk or bike ride to Hubbard Woods School, the Metra, and downtown Hubbard Woods. From the moment you step inside, you'll appreciate the abundance of natural light streaming through white Marvin windows, creating bright, inviting living spaces throughout. The welcoming living room centers around a fireplace, while the renovated kitchen with newer quartz countertops opens seamlessly to the spacious family and dining rooms. A dramatic wall of windows and door opens to the professionally landscaped backyard and patio, creating an ideal setting for both everyday living and entertaining. The second floor offers three generously sized bedrooms and a beautifully renovated marble hall bath completed in 2021, while an updated full bath on the main level provides added convenience for guests. The freshly painted basement offers flexible space for a home gym, playroom, or additional storage. Extensive recent improvements make this home truly move-in ready, including refinished hardwood floors, fresh interior and exterior paint, and numerous cosmetic updates completed in 2025. Buyers will also appreciate the peace of mind that comes with a complete tear-off roof and HVAC system installed in 2016, along with exterior tuckpointing of both the home and chimney completed in 2023. Outside, the professionally landscaped yard is filled with mature trees and seasonal blooms, creating exceptional curb appeal and year-round beauty. There is also the potential to add a detached garage or porte cochere (buyer to verify with the Village). Low real estate taxes and the unique benefit of access to both the Winnetka and Glencoe Park Districts add even more value to this exceptional offering. Everything you love about East Winnetka is just moments away-from Hubbard Woods School, the Metra, downtown Hubbard Woods, Tower Road Beach, and the Green Bay Trail just steps from your back door-making this a home you'll enjoy from day one.

154 Glenwood Avenue, Winnetka

1037 Oak Street, Winnetka
$2,155,000
4 Beds ⋅ 4 Baths ⋅ 12678232 MLS ⋅ CLOSED Status
Located in the heart of Winnetka and within the highly sought-after Crow Island School District, this impeccably maintained 5-bedroom, 3.1-bath home checks every box. Thoughtfully reimagined and beautifully updated, the first floor offers exceptional flow, abundant natural light and timeless finishes throughout. At the center of the home is the stunning kitchen, completely gutted and renovated in 2022 with top-of-the-line finishes and a thoughtful design. A large island serves as the heart of the kitchen and gathering space, while the chef's appliances and custom high-end cabinetry make it as functional as it is beautiful. The kitchen opens seamlessly to the family room, creating the perfect space for everyday living and entertaining. The screened porch offers great indoor/outdoor living. The first floor also features a gracious dining room, inviting living room, refreshed mudroom, stylish powder room, and exceptional custom millwork throughout. Upstairs, you'll find four spacious bedrooms and two full baths. The oversized primary suite has generous closet space and a beautifully appointed bath featuring dual vanities, a separate shower, and soaking tub. Three additional bedrooms are bright and airy, each with custom closet organizers. The lower level was largely renovated in 2023 and offers incredible additional living space with updated flooring, lighting, drywall, and expanded recreation areas. A fifth bedroom and full bath provide the perfect accommodations for guests, an au pair, or a private home office. The backyard offers great space for entertaining, kids playing and sunshine. The garage is oversized (2.5 spaces) and has extra depth for those suburban mom SUVs. Meticulously maintained and move-in ready, this exceptional home is ideally located just steps from town, train, parks, schools, and everything that makes Winnetka one of the North Shore's most desirable communities.

1037 Oak Street, Winnetka

1225 Elm Street, Winnetka
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 12657695 MLS ⋅ CLOSED Status
Privately tucked on an extra wide 1/3rd acre property, this fully re-imagined mid-century modern home offers exceptional design and incredible vistas of its lushly landscaped property. Thoughtfully curated with attention to detail and a sophisticated eye for design, the home blends timeless architecture with abundant natural beauty, right in the heart of Winnetka. A super chic, modern kitchen with abundant custom cabinetry and top-tier appliances is anchored by a large island and opens to a stunning dining room with radiant-heated floors and walls of windows beautifully framing panoramic views of the verdant property. The stylized mid-century living room features a contemporary gas fireplace and overlooks the professionally landscaped grounds, perennial gardens, and brick patio. The inviting family room, complete with radiant-heated floors and a second fireplace, offers a warm and stylish gathering place. The luxurious primary suite is a true sanctuary, featuring a private sitting room with built-ins, custom closets, and a spa-inspired bath. Three additional generously sized bedrooms - one ensuite and two sharing a hall bath - provide beautifully appointed modern accommodations for family and guests. The large rec room offers plenty of space for lounging, a work-out area and/or game area, plus a separate laundry room and access to the attached and heated 2-car garage. Every detail of this home has been thoughtfully re-imagined to create effortless indoor-outdoor living. Enjoy an intentional, design-forward home surrounded by beautiful grounds with blooming gardens, and located within easy walking distance to town, schools, parks, the A.C. Nielsen Tennis Center, the Winnetka Golf Club, and the Skokie Lagoons.

1225 Elm Street, Winnetka

1235 Scott Avenue, Winnetka
$2,505,000
5 Beds ⋅ 7 Baths ⋅ 12697023 MLS ⋅ CLOSED Status
Perfectly situated in the heart of Hubbard Woods, this bright 6 bedroom, 5.2 bath home offers an exceptional combination of timeless architecture, volume and one of Winnetka's most coveted walk to everything locations. Just steps from the Metra, walk to Hubbard Woods Elementary, Hubbard Woods Park, and neighborhood favorites including Mino's, Guanajuato, Spirit Elephant, Grateful Bites, & Graeters to name a few - this is North Shore living at its finest. Extensively renovated to 2026 standards, this home includes a kitchen overhaul with Taj Mahal honed quartzite countertops, full-height quartzite backsplash, an oversized island with seating, storage, an undermount sink, built in microwave drawer, Zephyr beverage refrigerator, updated hardware, and professionally refinished custom cabinetry. Premium appliances include a Sub-Zero fridge, Viking 8-burner cooktop, and Thermador double ovens. The kitchen has a defined area for a breakfast table, French doors with views of the deck and backyard. It flows seamlessly into the family room which features coffered ceilings, oversized windows, and a wood-burning fireplace. Exceptional scale and natural light define the rest of the main level, where 10-foot ceilings and oversized windows flood this home with natural light. A gracious foyer welcomes guests and opens to an elegant living room with a south-facing bay window and fireplace, a formal dining room, a private office with custom built-ins, a beautifully updated powder room, and a newly reimagined mudroom complete with heated floors and custom-designed storage. The second level has four spacious bedrooms, including a luxurious primary suite featuring two professionally designed walk-in closets and a stunning spa-inspired bath completed in 2026. Thoughtfully appointed with dual vanities, heated floors, floor-to-ceiling porcelain tile, an oversized soaking tub, walk in steam shower, and premium finishes throughout - the space offers the comfort and elegance of a luxury retreat. A second ensuite bathroom was completely renovated with a new shower, vanity, fixtures, heated floors, and designer finishes. The walk in laundry room features new quartz countertops, utility sink, refreshed cabinetry, and a new washer. Newly installed hardwood flooring throughout the second level completes the look. The third floor provides exceptional flexibility with a private suite featuring a full bath and walk-in closet, making it ideal as a guest bedroom, teen retreat, playroom, fitness studio, or second home office. The finished lower level has exceptional ceiling height and abundant natural light from four massive windows. This creates a living space that feels like an extension of the main level. Additional highlights include a spacious recreation room with fireplace, 1/2 bath, refreshed wet bar featuring quartz countertops, professionally painted cabinetry, and custom shelving, a generous billiards area, an oversized sixth bedroom with private ensuite bath-perfect for guests, an au pair, or multigenerational living. This exceptional home is move in ready and is three blocks from downtown Hubbard Woods!

1235 Scott Avenue, Winnetka

406 Woodley Woods, Winnetka
$2,450,000
6 Beds ⋅ 6 Baths ⋅ 12611829 MLS ⋅ CLOSED Status
MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 4/24/26! Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal chandelier, greets you to six bedrooms, four full baths, two half baths and over 5,400 square feet of refined living and sophistication. The eat in chef's kitchen features beautiful quartzite countertops with breakfast bar seating, stacked upper cabinets, walk in pantry, and premium appliances, including a Sub-Zero refrigerator, Thermador double oven, Bertazzoni cooktop with hood, and a Bosch dishwasher. The grand family room offers oak hardwood floors, soaring 15-foot vaulted ceilings with skylights, a striking stone wood-burning fireplace, and a wet bar, all overlooking the newer expansive Trex deck that wraps around the concrete inground pool. A west-facing four-season room is filled with natural light and provides views of the stone paver patio-ideal for summer bonfires. The main level offers an executive office with rich wood paneling, decorative sconces, and a built-in bookcase. Additional highlights include a comfortable living room with second gas-start fireplace and floor to ceiling Pella casement windows, a formal dining room, half bath, a first-floor guest suite with a newly renovated ensuite bath, and a well-organized laundry room with cubbies, wash sink, and folding area. Upstairs, you'll find five spacious bedrooms with brand-new carpet and solid-core doors, along with two full baths. The expansive primary suite features dual walk-in closets, individual vanities, a soaking tub, water closet, and an oversized steam shower. The finished basement adds approximately 2,300 square feet of recreation space, complete with built-in surround sound, a full kitchenette, bookshelves, ample storage, and a half bath. The home offers dual-zoned HVAC, a sump pump with battery backup, central vacuum system, a three-car garage equipped with a 220V outlet for electric vehicle charging, a newer asphalt driveway with stamped concrete front steps, freshly painted exterior, landscape lighting, outdoor speakers, and a partially fenced generous yard for backyard activities. Ideally located on the North Shore with easy highway access, this home is served by the highly sought-after New Trier High School and is within walking distance to award winning Marie Murphy Middle School. A true hidden gem of Winnetka!

406 Woodley Woods, Winnetka

134 Green Bay Road Unit #104, Winnetka
$400,134
2 Beds ⋅ 2 Baths ⋅ 12676299 MLS ⋅ CLOSED Status
Sun-drenched mornings define this coveted two-bedroom, two-bathroom residence. Located in a premier building within a highly sought-after location, this home welcomes you with a bright, cheerful, thoughtful layout. The east-facing exposure ensures the living spaces are bathed in natural light, while the charming private balcony offers the perfect spot for a morning coffee or an evening breeze. The spacious living and dining rooms, anchored by classic hardwood floors, create an inviting backdrop for both daily relaxation and lively entertaining. Nearby, the well-appointed galley kitchen strikes a balance between style and utility, offering plentiful storage and a convenient pass-through for effortless serving. The primary suite serves as a private retreat, complete with a dedicated primary bath and ample closet space. A second full bath is located off the hallway, easily accessible for guests. Currently, the second bedroom has been reimagined as a cozy den adjacent to the main living area, offering a flexible layout to suit your needs. Beyond the main living quarters, the building offers exceptional amenities, including fabulous party room featuring a kitchenette and a half bath, all overlooking the pool and patio. This is a smoke free building. One dog (20lb. wt. limit) or one cat is allowed.

134 Green Bay Road Unit #104, Winnetka

478 Sunset Road, Winnetka
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 12629591 MLS ⋅ CLOSED Status
They don't build them like this anymore, but they should! This solidly built custom Hemphill home is ideally located in sought-after East Winnetka and offers timeless character, quality craftsmanship, and thoughtful updates. Built in 1936 with exceptional materials and lovingly maintained by only two owners, this home combines classic elegance with modern comfort. The spacious living room features decorative plaster crown molding, a gas-log fireplace, and built-in cabinetry, while the formal dining room showcases equally impressive molding and elegant wainscoting. The kitchen is appointed with high-end appliances, beautiful wood cabinetry, granite countertops, and an eating area. A welcoming family room overlooks the expansive fenced backyard and slate patio. Upstairs, four generously sized bedrooms each offer walk-in closets. The second level also includes an updated primary bath, a hall bath, and an en-suite bath, along with a large cedar closet and a deck overlooking the backyard. The basement offers exceptional additional space with four separate rooms: a recreation room with wood-burning fireplace, a work/hobby room, a "canning"/storage room, and a utility area with laundry. Direct access to the oversized attached two-car garage adds convenience. Set on a wide lot, 478 Sunset offers a wonderful floor plan just a few blocks from parks, schools, beaches, the train, and more.

478 Sunset Road, Winnetka

1482 Edgewood Lane, Winnetka
$2,437,125
5 Beds ⋅ 6 Baths ⋅ 12640779 MLS ⋅ CLOSED Status
Nestled on a charming, quiet, tree-lined street in Winnetka's highly sought-after Hubbard Woods neighborhood, 1482 Edgewood Lane offers the perfect blend of timeless style, modern functionality, and an unbeatable North Shore location-just steps from Nick Corwin Park, and less than a mile to town, train, and schools. Built in 2015, this stunning Nantucket-inspired newer construction home is beautifully maintained and thoughtfully designed with today's buyer in mind. Offering 6 bedrooms, 5.1 baths, and exceptional living space across four finished levels, this home truly has it all. A gracious foyer welcomes you inside, where hardwood floors, classic millwork, and abundant natural light set the tone throughout. The heart of the home is the gorgeous white chef's kitchen, which opens seamlessly to the inviting family room featuring coffered ceilings, built-ins, and access to the extra-deep (50' x 200') backyard - perfect for everyday living and entertaining alike. The main level also includes a handsome office with custom built-ins, elegant dining room, charming sitting room, and an ideal mudroom that connects to the attached two-car garage. The second floor features four spacious bedrooms and three full bathrooms, including a luxurious primary suite with soaring ceilings and a spa-like bath complete with heated floors, dual vanities, soaking tub, oversized walk-in shower, and two walk-in closets. The finished third floor offers incredible flexibility with a private bedroom suite and full bath-ideal as a guest retreat, office, or playroom. The lower level is equally impressive, featuring exceptional ceiling height, an enormous recreation room, wet bar, gym, sixth bedroom, and an additional full bath. Beautifully updated and impeccably maintained throughout, 1482 Edgewood Lane checks every box in one of Winnetka's most beloved neighborhoods. A truly special home in an idyllic setting.

1482 Edgewood Lane, Winnetka



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