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560 Elm Street, Winnetka
$2,775,000
5 Beds ⋅ 5 Baths ⋅ 12590637 MLS ⋅ CLOSED Status
Exceptional East Winnetka residence on a rare .4-acre lot, steps from the lake, beaches, schools, town, and train. Beautifully maintained and rich in character, this historically significant home blends timeless architectural detail with the comforts and scale suited for modern living. The home offers 5Bd/4.5Ba, with all bedrooms located on the second floor-an increasingly sought-after layout for today's buyers. The main level features expansive living spaces, including a dramatic great room, drenched in sunlight, with vaulted ceilings and a curved staircase which leads to the kitchen. The kitchen is equipped with a custom built-in breakfast booth, stone counters, luxury appliances, and extra tall cabinets. The large formal dining room is connected to the kitchen and leads to a parlor w/fireplace, a stately home office, and a comfortable den (en suite powder room) for football games and movies. A tasteful mudroom connects directly to the attached two-car garage, providing a convenient everyday entry and exit. Lastly, you'll find the outdoor retreat that is your spacious backyard. Professionally landscaped and fully fenced, it offers scale not often found east of Green Bay Rd. The elegant bluestone patio offers an ideal setting for outdoor dining, entertaining, or relaxing after a day at the beach!

560 Elm Street, Winnetka
1092 Ash Street, Winnetka
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 12600308 MLS ⋅ CLOSED Status
Welcome home to 1092 Ash Street. A true jewel nestled in the sought-after "Tree Streets" of Winnetka. Walking distance to elementary, middle school & jr. high schools as well as the village shops, commuter train, parks, park district fields and amenities. This home has been beautifully updated with care to embrace the original charm while adding modern sophistication and open concept living. Welcoming front porch invites the wonderful neighborhood in! Fabulous open kitchen, eat in area, & family room features fireplace, built-ins and access to a rear deck & fenced in yard. There is a main level office; could work as a bedroom, if needed, which is adjacent to a full bathroom. Hardwood floors & appealing millwork throughout the main floor. Living rm has bay window, wood-burning fireplace with marble surround. Spacious separate dining room off living room. Upstairs has four family bedrooms. Newly remodeled Primary bedroom suite with fireplace, walk-in closet, spa tub and separate shower. There are 3 more generous bedrooms and an updated full hall bath. Basement includes a step-down rec room with high ceilings, & climbing wall for the kiddos. Large laundry room and lots of closets for storage. Fenced back yard, 2 car detached garage off alley. Wow!

1092 Ash Street, Winnetka
598 Birch Street, Winnetka
$2,085,000
3 Beds ⋅ 5 Baths ⋅ 12590477 MLS ⋅ CLOSED Status
There is no better in-town location than this "like new" construction, transitional jewel box beauty. Delivering chic, youthful living with a very high-end, hotel vibe, all wrapped up on a fab block with a rare heated driveway & attached two-car garage-ready for winter weather! This superior smart-tech build has been outfitted to perfection with floor-to-ceiling black iron windows, natural oak sawn, hand-beveled wide plank floors, custom high-end cabinetry, and radiant heat throughout the lower level and garage. There is even a posh dog wash off the mudroom! Atrium foyer leads to a fab circular entertaining floor plan, with the center hub being the gorgeous, zen-like Chef's kitchen, all in natural hues with thick Taj Mahal quartz c-tops, two-toned painted island with oak sawn paneling, matching oversized sink with brass faucet. Ann Sacks glazed cream subway tile blends beautifully with off-white cabs. This fab kitchen is adjacent to a sleek butler's pantry with Thermador coffee station, plus a walk-in pantry with double ovens and microwave. All professional-level Thermador appliances: 6-burner cook-top with griddle, two dishwashers, full-size separate fridge & freezer. Cozy family room with a WB fireplace is the perfect place to watch TV while preparing dinner, inside or out on the decked-out outdoor space with FP and grilling station, all on a gorgeous patio. Seamless flow to the deluxe LL with an incredible rec center equipped with a loaded wet bar, powder room, and inviting guest suite. En-suite spa luxe bath and customized walk-in closet complement this plush LL space with natural light. Sun-drenched 2nd floor with vaulted ceilings and floor-to-ceiling windows illuminate this beautifully detailed level with a full laundry room. Two beds share a spa bath in soothing tones with dual vanity and tub, accented in porcelain tile. Posh, boutique-level primary suite with horizontal fireplace, customized walk-in closet, separate office area with private balcony, and the most luxurious bathroom with deep soaking tub, heated floors, and steam shower, polished in gorgeous tiles & materials. While this custom home is not huge, the finish level is turnkey perfection, as this notable North Shore builder brings a magnificent transitional vibe, so no decorator is needed. This is the perfect in-town residence that makes leaving the city super easy, as everything is a 3-minute walk... grab your Starbucks on the way to the train, meet for drinks at the best bar in Winnetka, Pomeroy, and run to The Grand for any last-minute forgotten ingredients when entertaining. It's time for fun at 589 Birch! TAXES are being reduced. There was an error in square footage when house was assessed as new construction-coming down!

598 Birch Street, Winnetka
334 Woodland Avenue, Winnetka
$3,005,000
4 Beds ⋅ 5 Baths ⋅ 12507097 MLS ⋅ CLOSED Status

334 Woodland Avenue, Winnetka
153 Bertling Lane, Winnetka
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 12567575 MLS ⋅ CLOSED Status
This East Winnetka finely built red brick colonial delivers above & beyond luxurious living with a phenomenal location steps to the Indian Hill train station, blocks to New Trier East and Greeley Elementary, and best yet...Elder Park beach, which will be opening summer of 2026! With only 17 houses on this tucked-away street, this timeless architectural classic doesn't miss a beat as the four floors of expansive living make perfect sense. Step inside to a traditional formal foyer accented with lightly stained grey oak hardware floors, Farrow & Ball freshly painted walls, soaring ceilings, tailored millwork, and an abundance of natural light. Formal living is the perfect size with FP w/ soapstone surround leads to a finely appointed dining room w/walk-through butler's pantry. Recently revamped Chef's kitchen with White Dove cabinetry, thick quartz island with RH hardware amplifies this fab space. Separate breakfast space overlooks private, professionally landscaped backyard. Large sun- drenched family room with FP ideally opens to kitchen and breakfast room w/ built out mudroom. A large office with custom built-ins and Phillips Jeffries grasscloth wallpaper is the perfect private getaway room. Expansive second floor with a massive luxury primary suite with an enormous walk-in closet outfitted with custom antiqued built-in dressers. Spa stone bath with steam shower, dual vanities, and soaking tub. 2nd and 3rd bed w/ Jack-n-Jill bath with Carrera marble c-tops and tub. 4th bed with en-suite bath, full 2nd floor laundry, and a reading nook. 3rd floor is used as an art studio now, with roughed-in plumbing for another bath, and then converting to a 6th bed. Awesome deep LL with soaring ceilings, exercise room, and 5th bed with attached bath. Huge rec room accented w/ a flagstone wall with a full bar & walk-in wine cellar, which is now serving as a billiards room. A separate theater room with a projection screen is the best unexpected bonus of this level. Grounds are so well done with bluestone patios & natural arbor vitae privacy fence. Plus a 2-car attached garage for added convenience. There is not one box left unchecked on this special home, as it just feels so solid and even shows better in person. Your answer if walking to everything is something you value in North Shore living.

153 Bertling Lane, Winnetka
735 Foxdale Avenue, Winnetka
$1,175,000
4 Beds ⋅ 4 Baths ⋅ 12541890 MLS ⋅ CLOSED Status
Rarely available gem in the heart of Winnetka. Main floor has dining room, living room with gas fireplace, den and powder room. Second floor has primary bedroom with attached bath along with three additional bedrooms and another full bath. Laundry room, bonus room and half bath in the basement. Detached garage. Good sized backyard. Recent improvements include copper pipes to the street, side yard cedar fence, refrigerator, chimney liner, Unico A/C upgrade & A/C compressor. Unbeatable location, steps to restaurants, shops, metra and more!

735 Foxdale Avenue, Winnetka
277 Hibbard Road, Winnetka
$1,860,000
5 Beds ⋅ 5 Baths ⋅ 12574265 MLS ⋅ CLOSED Status
This beautifully renovated Hemphill Cape Cod lives effortlessly with a coveted first-floor primary suite. Offering five bedrooms and four and a half baths, the layout includes two additional bedrooms on the main level for exceptional flexibility. A full gut renovation and two-story expansion completed in 2015 by Twenty 9, Inc. of Highland Park seamlessly blends classic architectural character with modern functionality. The main living spaces flow effortlessly, anchored by a spacious kitchen that opens to the informal dining area and Great Room, highlighted by a wood-burning see-through fireplace and timeless architectural details. Two additional bedrooms are located on the second floor, while the finished basement provides flexible additional living space for recreation for guests or work-from-home needs. The fully fenced backyard offers a private outdoor retreat with a large bluestone patio, storage shed, and professionally landscaped grounds complete with irrigation and front-yard executive lighting. A semicircular driveway enhances curb appeal and provides convenient parking, complemented by an attached 2.5-car heated garage with built-in cabinetry and rack storage systems, plus an additional grass-covered parking pad. A full-height attic provides excellent storage and future expansion potential. Ideally located within the highly regarded New Trier High School district and just a short walk to Skokie Playfields, parks, recreation, and everyday amenities.

277 Hibbard Road, Winnetka
985 Pine Tree Lane, Winnetka
$3,000,000
5 Beds ⋅ 6 Baths ⋅ 12564971 MLS ⋅ CLOSED Status
Set on a half-acre, this custom-built 5+ bedroom, 5.1 bath home offers elegant design, well-proportioned rooms, generous light, and spaces that feel both beautiful and comfortable from the moment you walk in. Rooms flow easily for entertaining a crowd, yet the home never loses its sense of warmth for everyday living. Sunlight fills the foyer, highlighting the striking staircase and spacious two story foyer and wide hall that leads to all first-floor rooms. The living and dining rooms are designed for both gatherings and quiet moments. Oversized windows frame views of the grounds and fill the rooms with light, while a butler's pantry with custom cabinetry connects the dining room to the kitchen. Designed with clean lines and high-quality finishes, the kitchen features custom cabinetry, a generous island, top appliances, quartz countertops, and a breakfast area, all framed by bright windows. Vaulted ceilings, a fireplace, and built-ins anchor the family room, while two walls of windows open to patios and the gorgeous landscaped backyard.A first-floor bedroom suite provides flexibility as a guest room or home office. The second floor features a true primary suite. The primary bedroom opens to a sitting room with fireplace and doors to a private deck with serene views of the yard. The primary bath is both luxurious and indulgent, with heated floors, a deep soaking tub, spacious walk-in shower, and custom cabinetry, and adjoins two oversized custom closets. Two additional bedrooms share a renovated bath with heated floors, while a third bedroom has its own ensuite. A second-floor laundry room is conveniently located here. The third floor offers flexible space for a playroom, study, or home office. The lower level almost feels like a separate home, with soaring ceilings, huge windows, and radiant heated tile floors. It's a space built for movies, games, workouts, hobbies, or gatherings with friends, with a full bath and an additional bedroom or office. Ideally located near walking and biking trails, Corwin Park, Hubbard Woods shops and restaurants, and with easy access to the expressway

985 Pine Tree Lane, Winnetka
312 Rosewood Avenue, Winnetka
$1,725,000
4 Beds ⋅ 4 Baths ⋅ 12557569 MLS ⋅ CLOSED Status
This home delivers space, style, and everyday ease. The outdoor space is elegantly appointed with a large patio, pergola, and beautifully landscaped. Inside, this 4 bedroom, 3 and a half bath home offers a smart, flexible layout with generous room sizes, hardwood floors, and natural light throughout. The primary suite has been reimagined with custom closets and a new spa-inspired bath, plus a second en-suite bedroom ideal for guests or home office use. Extensively maintained and improved over time, the home is move-in ready. The location is hard to beat - close to schools, parks, Metra, and downtown.

312 Rosewood Avenue, Winnetka
607 Orchard Lane, Winnetka
$1,300,000
3 Beds ⋅ 4 Baths ⋅ 12582600 MLS ⋅ CLOSED Status
So much to love about this East Winnetka charmer, from its curb appeal and large lot to the sun-filled rooms and multiple living spaces. The bluestone walkway, front steps and porch welcome you to this perfectly sized home. Main floor features include formal living room, large eat-in kitchen, separate dining area, powder room and step-down family room. The upstairs offers 3 bedrooms, including primary (has room for a king bed) with ensuite bath, and a bedroom with a private enclosed porch overlooking the rear yard. Basement offers additional living, working or exercise space, laundry and an extra half bath. Clean, neutral decor throughout, ready for you to move right in. Large backyard includes sports court and generous 2.5-car garage. Beautifully landscaped, both front and back yards with blooming perennials. Wonderful location so close to Greeley, NT, NSCD, the beach, the Green Bay Trail, downtown Winnetka, access to Indian Hill or Winnetka Metra stops, and so much more.

607 Orchard Lane, Winnetka
955 Vernon Avenue, Winnetka
$1,875,000
5 Beds ⋅ 4 Baths ⋅ 12576687 MLS ⋅ CLOSED Status
Nestled in the heart of one of Winnetka's most coveted neighborhoods, this handsome Tudor seamlessly blends timeless architecture with today's luxury finishes and amenities. Enter through the arched doorway to find beauty at every turn with new windows throughout the main rooms of the first floor. The spacious formal dining room conveniently opens directly to the beautiful kitchen. The timeless kitchen includes high-end appliances, custom built-ins, countertop seating, and gorgeous finishes. The living room has a cozy fireplace, custom built-ins with new picture lights and access to the sunroom which is a great flex space that could be whatever you need it to be. The second floor includes 4 bedrooms and 3 bathrooms. The renovated primary suite with a spa-like bathroom and large walk-in closet. The third floor features the 5th bedroom which could also be a great office space! The finished basement has a large rec room, wet bar, extra mudroom and tons of storage. Extensive improvements throughout inside and out. Rare 2 car heated attached garage, new privacy professional landscaping along the new iron fence, as well as a gorgeous stone patio perfect for entertaining - this home offers a spectacular level of living just a few blocks from Corwin Park, award winning Winnetka schools and downtown Hubbard Woods.

955 Vernon Avenue, Winnetka
270 Euclid Avenue, Winnetka
$1,384,000
4 Beds ⋅ 3 Baths ⋅ 12570496 MLS ⋅ CLOSED Status
Tucked into a very private setting on a beautiful 1/3-acre lot in Winnetka, this mid-century modern ranch home offers timeless design and exceptional indoor-outdoor connection. Floor-to-ceiling windows fill the home with natural light and frame serene views throughout. A spacious great room and dining room combination creates an inviting, open layout ideal for everyday living and entertaining. The home features four bedrooms and three full baths, offering flexibility for families, guests, or a home office. An attached two-car garage adds everyday convenience and easy access to the home. The full basement provides valuable additional space for recreation, storage, or future expansion. This is a rare opportunity to own a classic mid-century modern retreat in one of Winnetka's most private settings.

270 Euclid Avenue, Winnetka
567 Hill Terrace, Winnetka
$1,795,000
4 Beds ⋅ 4 Baths ⋅ 11911610 MLS ⋅ CLOSED Status
**MULTIPLE OFFERS RECEIVED** HIGHEST & BEST DUE MONDAY 3/9 BY 11AM** Timeless Winnetka Colonial on Private Hill Terrace. Set on coveted Hill Terrace, a charming private street just moments from the Indian Hill Metra station, this beautifully maintained Winnetka Colonial offers an exceptional combination of classic architecture, thoughtful updates, and an unmatched walk-to-everything location. Just steps from parks, the Green Bay Trail, top-rated schools, town, and the train, the home provides effortless North Shore living. Inside, elegant living spaces showcase rich hardwood floors, crown molding, custom millwork, and designer lighting throughout. The gracious living room with restored gas fireplace opens to a serene screened porch, creating a perfect retreat for morning coffee or evening relaxation. A sophisticated butler's bar with beverage refrigerator connects the living and family rooms, providing seamless flow for entertaining. The chef's kitchen features white cabinetry, granite countertops, a generous center island with second sink, and professional-grade appliances, all opening to a spacious family room with views of the beautifully landscaped backyard. The second level offers a luxurious primary suite with private screened sleeping porch, spa-like bath with steam shower and jacuzzi tub, and custom Elfa closets. Three additional bedrooms and a beautifully updated hall bath complete the floor. A finished third-floor retreat provides ideal flex space for a fifth bedroom, office, or playroom, while the lower level offers a large recreation room, wet bar, full bath, laundry, and extensive storage. Outside, professionally landscaped grounds feature mature trees, lush plantings, a large brick paver patio, deck, and fully fenced yard-creating a private outdoor oasis. Numerous recent improvements, including a new roof, upgraded lighting and electrical, security system, and mechanical enhancements, further elevate this exceptional residence. A rare opportunity to enjoy timeless Winnetka charm, modern comfort, and an extraordinary location just steps from the train and top schools. New roof 2023, Fireplace restoration with new liner, new gas logs 2024. Newer LG Washer Dryer 2022, New Frigidaire double oven 2026, New Frigidaire cooktop 2026. The property has been well cared for and maintained. The property is being sold as-is condition. The seller is an Illinois licensed real estate broker.

567 Hill Terrace, Winnetka
711 Oak Street Unit #106, Winnetka
$589,000
3 Beds ⋅ 2 Baths ⋅ 12531323 MLS ⋅ CLOSED Status

711 Oak Street Unit #106, Winnetka
1492 Asbury Avenue, Winnetka
$1,030,000
4 Beds ⋅ 3 Baths ⋅ 12331764 MLS ⋅ CLOSED Status
Rehabbers-Opportunity Awaits! Have you been searching for a home on one of Hubbard Woods' most cherished streets? A place where your family can grow, in a community known for its charm and friendly community? This is that rare opportunity. This solid 4 bed, 2.5 bath home is full of potential and perfectly situated in a sought-after neighborhood with top-rated schools. With thoughtful updates and a little vision, this property can be transformed into something truly special-adding immediate value in a location that supports it. Offered AS-IS, this is an ideal chance to customize without overpaying for someone else's choices. It's priced to reflect the work it needs-making it a smart move for those who understand the value of investing in the right home, in the right location Don't miss the chance to create something amazing in one of the North Shore's most beloved communities. Come take a look and imagine the possibilities! AS-IS

1492 Asbury Avenue, Winnetka
1215 Spruce Street, Winnetka
$2,000,000
4 Beds ⋅ 5 Baths ⋅ 12551088 MLS ⋅ CLOSED Status
A RARE find...Amazing home with an expansive *first floor Primary suite, set on a spectacular half-acre in a prime Winnetka location! This deceptively spacious home offers exceptional indoor-outdoor living and a versatile floor plan. The professionally landscaped backyard is a true showstopper, featuring mature trees, perennial gardens and a spacious bluestone patio...perfect for large-scale entertaining, family gatherings and everyday enjoyment. The first floor boasts fabulous flow with a family room, separate dining room and a grand living room highlighted by an oversized picture window overlooking the stunning backyard. Chef's you will love cooking in the large kitchen with new Quartz countertops, new sinks/faucets/lights, walnut cabinetry, double ovens, double fridge/freezer, walk-in pantry, an large island and an eat-in area. A rare and highly desirable first floor primary anchors its own private wing of the home, offering incredible flexibility. Several rooms were thoughtfully combined to create a generous suite currently featuring a bedroom, office/sitting area, walk-in closet, large en-suite bath with double vanities, soaking tub, shower and a spa/resistance pool. This versatile space can easily be reimagined to suit your needs. An elevator services all 3 floors. The second floor offers three nice-sized bedrooms and two full bathrooms. The expansive lower level is surprisingly large, with multiple flexible spaces ideal for a rec room, playroom, workout room, home office, arts and crafts area and a separate billiards room. Large laundry room and 2-car *attached garage. 2nd driveway added 2 years ago on North side of the property...could also be turned into a great sport court. Recent improvements include fresh interior paint throughout the entire house and hardwood floors added in key areas and all hardwood refinished. With its exceptional lot size, unbeatable location...walk-to-town, train, beach, parks, and the Hibbard Road sports complex, this is a truly a unique opportunity. A beloved home, now ready for new owners to create lasting memories!

1215 Spruce Street, Winnetka
706 Foxdale Avenue, Winnetka
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 12555565 MLS ⋅ CLOSED Status
Move in ready and walk to everything! 706 Foxdale has the layout and amenities you are looking for. Step into this welcoming home and enjoy the soaring ceilings in the 2 story family room. The first floor layout is perfect for family gatherings, offering a formal living and dining rooms, as well as the family room with a fireplace and abuilt-ins with a wet bar. The kitchen opens to the family room and has a great island and eating area with all stainless appliances. The mud room/laundry room are conveniently located off the two car garage. The second floor has four well sized bedrooms which includes the primary suite which has a luxurious bath, walk-in closet and sitting area. The basement has new carpet and offers ample recreation space. Back yard is spacious and fully fenced. Fireplace "as is" - owners have never used it.

706 Foxdale Avenue, Winnetka
1351 Scott Avenue, Winnetka
$1,720,000
4 Beds ⋅ 4 Baths ⋅ 12574078 MLS ⋅ CLOSED Status

1351 Scott Avenue, Winnetka
640 Winnetka Mews Unit #405, Winnetka
$639,000
3 Beds ⋅ 3 Baths ⋅ 12544291 MLS ⋅ CLOSED Status
Welcome to this spacious and sun-filled top-floor residence at the Winnetka Mews, a thoughtfully designed and impeccably managed condominium community in the heart of Winnetka. This classically updated 3-bedroom, 3-bath home enjoys south, east, and west exposures and offers exceptional one-level living with generous room sizes and an effortless floor plan. The expansive living room, anchored by a wood-burning fireplace, enjoys tranquil east-facing views and flows seamlessly into the dining area, kitchen, and den (or optional third bedroom). The dining area is both flexible and inviting, with space for multiple furniture arrangements and access to an east-facing balcony (11' x 6') - perfect for enjoying the sun throughout the day. The kitchen is conveniently located for easy everyday living and entertaining. The den (or third bedroom) is ideally situated off the living room and is adjacent to a full bath, offering excellent flexibility for guests or home office use. The spacious primary suite features a large walk-in closet and a well-appointed en suite bath with double sinks, a separate tub and shower. The additional bedroom, currently used as an office, includes ample storage and its own private en suite bath. Recent improvements include new carpeting, fresh paint, replacement windows (Marvin) throughout, and an extensive list of solid mechanical updates. In-unit laundry is an added convenience. The Winnetka Mews offers outstanding amenities including an indoor heated garage, abundant guest parking, on-site management and engineer (who resides in the building), an exercise room and a delightful outdoor pool with new decking/patio. The prime location provides exceptional walkability to Winnetka's restaurants, shops, two grocery stores, library, parks, and beaches-offering a truly convenient and vibrant lifestyle.

640 Winnetka Mews Unit #405, Winnetka
1370 Sunview Lane, Winnetka
$1,885,000
4 Beds ⋅ 5 Baths ⋅ 12524601 MLS ⋅ CLOSED Status
Exquisitely crafted for luxurious living and effortless entertaining, this exceptional residence, custom designed by the homeowner and noted local architectural firm W.D. Murphy Associates, backs onto the serene golf course, offering picturesque views from every room and utmost privacy. Encompassing over 4,600 square feet of refined living space, this home lives like a ranch, with the vast majority of rooms situated on the main level. A grand vaulted room with skylights on the second floor creates an inspiring space perfectly suited for a fitness studio or art retreat. The interior radiates natural light through multiple skylights and showcases stunning Teak Parquet hardwood floors. A magical sunroom captures sweeping golf course vistas, while a sophisticated library/bedroom features a marble gas fireplace surrounded by custom cherry bookshelves. The expansive primary suite is an oasis of comfort, boasting separate walk-in closets, built-in cabinetry and luxurious baths. Additional highlights include a cooled wine room, a three-car heated attached garage, and a brand-new roof, making this home an unparalleled offering in both style and functionality.

1370 Sunview Lane, Winnetka
1070 Fisher Lane, Winnetka
$3,300,000
5 Beds ⋅ 6 Baths ⋅ 12551428 MLS ⋅ CLOSED Status
Winnetka living at its finest! This timeless Paul Konstant custom-designed home is set on a rare, sought-after approximate 3/4 acre property on a private lane in East Winnetka and offers over 7900 square feet of transitional living space. Walking into the elegant foyer, the main level features a gracious living room with fireplace and attached sitting room with built-ins, formal dining room, and a transitional chef's kitchen with sun-filled breakfast area overlooking the expansive backyard. The family room with fireplace and office/sunroom (possible first floor bedroom) provide ideal spaces for everyday living and working from home. The second level presents an outstanding family layout with five generous bedrooms and a conveniently located laundry room. The luxurious primary suite is a true retreat boasting a volume ceiling, wood-burning fireplace, dual walk-in closets, spa-like bath, and a private balcony. The finished lower level provides another level of entertainment for the whole family, featuring a large recreation area with wet bar, exercise room, full bath, and a versatile bonus room (media room). A covered rear porch overlooks the private backyard-perfect for family gatherings, or a future pool. Additional highlights include abundant architectural detail and quality throughout, substantial mudroom with side door, ample storage, and an attached three-car garage. Recent upgrades include new hardwood floors, newly renovated basement, new led lighting and chandeliers, new roof, new furnace, and water heaters. Ideally located within walking distance to Hubbard Woods, Metra train, and Lake Michigan, you do not want to miss this one!

1070 Fisher Lane, Winnetka
1311 Scott Avenue, Winnetka
$2,025,000
4 Beds ⋅ 5 Baths ⋅ 12552787 MLS ⋅ CLOSED Status
MULTIPLE OFFERS RECEIVED, SHOWINGS WILL CONTINUE THROUGH THURSDAY MORNING (2/5) WITH ANY ADDITIONAL OFFERS REQUESTED BY NOON ON THURSDAY. Set on a stately, extra-large lot in the heart of Hubbard Woods, this enchanting brick Tudor blends timeless elegance with a fresh, modern sensibility. Oversized windows flood the home with natural light, while graceful archways lead to beautifully proportioned rooms designed for both everyday living and entertaining. The spacious living room features a striking arched fireplace with gas logs and flows seamlessly into the dining room, complete with ample storage and custom built-ins. At the center of the home is the recently renovated kitchen, showcasing top-of-the-line appliances, premium finishes, and a clean, contemporary aesthetic. A stunning music room and a charming three-season porch add warmth and versatility to the main level, while a mudroom with an oversized walk-in closet and a convenient powder room complete the space. An elegant curved staircase leads to the second floor, which includes a large primary suite, two additional bedrooms, a second floor laundry and a hall bath. The finished third floor offers a second, recently updated primary suite, along with flexible space ideal for a home office, gym, or studio. The lower level provides a relaxed family room with a built-in entertainment center, a half bath, a full laundry room with an additional mudroom, and abundant storage. The insulated two-and-a-half-car garage was rebuilt in 2019 and features two EV charging ports and exceptional storage. Outdoors, the expansive, fully fenced yard is a private oasis, professionally landscaped with lush, low-maintenance perennial gardens. Enjoy a large bluestone patio, pond, courtyard, kitchen garden, irrigation system, and multiple spaces for gathering and play. Recent improvements include a new roof (2024), Pella windows (2022), and numerous mechanical updates. Located just three blocks from the train, town, parks, and restaurants. Children attend highly sought-after Hubbard Woods Elementary School, ranked #1 in suburban Cook County by Chicago Magazine (September 2025). Agent owned. Too many upgrades to list - please see Additional Information for full details.

1311 Scott Avenue, Winnetka
380 Green Bay Road Unit #1B, Winnetka
$1,117,000
2 Beds ⋅ 2 Baths ⋅ 12569068 MLS ⋅ CLOSED Status ⋅ Hedge Row BLDG.
Rarely available first-floor condo in sought-after Hedge Row, ideally situated on the quiet and private rear side of this boutique Winnetka building. Light-filled and spacious, this home lives beautifully like a single-family residence with an exceptional, open layout. The first-floor location offers additional square footage, currently enjoyed as a dedicated dining area, and opens to a desirable private patio, perfect for relaxing or entertaining. Two side-by-side parking spaces in the heated garage complete this exceptional offering. A truly special opportunity you won't want to miss.

380 Green Bay Road Unit #1B, Winnetka
Winnetka
$450,000
12595958 MLS ⋅ CLOSED Status

Winnetka
674 Hill Road, Winnetka
$5,600,000
6 Beds ⋅ 6 Baths ⋅ 12541786 MLS ⋅ CLOSED Status
SOLD BEFORE PROCESSING. Welcome home to this extraordinary property designed by award winning Morgante-Wilson Architects and renowned designers James Thomas Interiors. The curb appeal, with its clean lines, is simple elegance. Sitting on one acre of gorgeous private grounds, this home is walking distance to Indian Hill Metra station, downtown Winnetka, New Trier High School and a short bike ride to Greeley Elementary school. Sophisticated yet casual, this 5/6 bedroom and 4.2 bath home offers flowing spaces and unparalleled natural light. As you walk through the beautiful entryway then foyer, take note that all primary 1st floor rooms (living, dining, sun, family room and kitchen) have walls of windows overlooking the breathtaking back yard. The elegant yet comfortable spacious living and dining rooms open to one another and each have impressive fireplaces. Both open to the comfy sunroom creating outstanding open yet well-defined entertaining and living space. Breathtaking describes the enormous kitchen with glass enclosed breakfast area, dramatic vaulted ceiling, clerestory windows, expansive island with seating, high-end refrigerator/freezer, leathered granite, huge walk-in pantry, and beautiful custom finishes. Cozy up in front of the fireplace in the lovely family room which smartly includes a faux-leather banquette perfect for homework or family game night. The first floor is completed with a wonderful private office, two, yes two mudrooms, a lovely powder room and a two-car attached heated garage. (Two more garage spaces are on the ground floor of the unfinished coach house). On up the grand staircase towards the second floor, but with a half-way stopping point at the "Palm Room", a sun-drenched bonus room. The primary suite offers a feeling of serenity with its south facing sunlight and pastoral palette in the beautiful primary bathroom. Two wonderful walk-in closets. The secondary bedrooms on the second floor are spacious and their bathrooms on-trend. Dream laundry room! The third floor is outstanding with a huge bedroom that fits two double beds, plus a full bath, a large exercise room and a great additional family room. Exceptional family space in this home! Add to that a basement rec room, half bath and huge unfinished storage space. Beautiful patio with grass-tiered steps opens up to the oasis-like back yard designed by Chicago's premier landscape design team Carrie Woleban/Frank Mariani. Simply extraordinary.

674 Hill Road, Winnetka
640 Hill Road, Winnetka
$4,255,000
6 Beds ⋅ 7 Baths ⋅ 12447231 MLS ⋅ CLOSED Status
Greeley and Winnetka schools!! Welcome to Meadowpool - a distinguished Tudor residence nestled on a meticulously landscaped and wooded one acre lot. Built in 1923, the home's design exudes classic Tudor charm with stucco and stone exterior and a slate roof. The entryway is adorned with leaded glass windows and rich woodwork and leads to a charming living room featuring a limestone fireplace. The spacious kitchen with custom wood cabinetry, premium appliances, breakfast area and counter seating flows into a family room boasting vaulted ceilings. The spacious primary bedroom has a lovely marble fireplace plus his and hers walk-in closets and an updated en-suite bath. 3 more bedrooms (one currently used as an office) and 2 updated baths on the 2nd floor plus a playroom. 2 airy, treetop bedrooms and a large recreation room are located on the 3rd floor. Finished basement with rec room, workout room and wine cellar/tasting room. Step out into the dreamy back yard which features the heated inground pool, outdoor kitchen, fireplace for gathering and a hot tub. 3 car attached garage. Walk to New Trier, Faith Hope, train and downtown Winnetka. Don't miss this absolute gem!! Make an offer!!

640 Hill Road, Winnetka
925 Elm Street, Winnetka
$925,000
3 Beds ⋅ 4 Baths ⋅ 12559211 MLS ⋅ CLOSED Status
LOCATED JUST ONE BLOCK FROM DOWNTOWN WINNETKA, FOUR BLOCKS TO THE METRA, AND EIGHT BLOCKS TO LAKE MICHIGAN, THIS CHARMING CORNER-LOT HOME BLENDS TIMELESS CHARACTER WITH THE COMFORT AND CONFIDENCE OF MODERN LIVING. THOUGHTFULLY AND COMPREHENSIVELY UPDATED IN 2021, THE HOME FEATURES ALL NEW ELECTRICAL WIRING, NEW PLUMBING LINES, CENTRAL HVAC WITH A/C AND HEAT, WINDOWS, FLOORS, AND OTHER MAJOR MECHANICAL AND FUNCTIONAL SYSTEMS - THE LARGE-TICKET IMPROVEMENTS THAT PROVIDE TRUE LONG-TERM VALUE. BEAUTIFUL RED OAK FLOORS FLOW THROUGHOUT THE HOME, COMPLEMENTING HIGH CEILINGS AND BRIGHT, INVITING SPACES. THE REMODELED KITCHEN IS DESIGNED FOR BOTH EVERYDAY LIVING AND ENTERTAINING, FEATURING A HUGE ISLAND, FARMHOUSE SINK, CARRERA QUARTZ COUNTERTOPS, WHITE CABINETRY, COFFERED CEILINGS WITH BRASS LIGHT FIXTURES, AND CROWN MOLDING. THE MAIN LEVEL OFFERS RANCH-LIKE LIVING WITH TWO FULL BEDROOMS AND TWO FULL BATHROOMS, WHILE THE SECOND LEVEL FEATURES A THIRD BEDROOM, A FULL BATHROOM, A BONUS ROOM, AND ADDITIONAL STORAGE. LANDSCAPING INCLUDES PAVERS AND BEAUTIFUL HYDRANGEAS, CREATING A WELCOMING OUTDOOR SETTING, ALONG WITH AN OVERSIZED CRAWL SPACE THAT PROVIDES EXCELLENT STORAGE. A RARE OPPORTUNITY TO ENJOY THE HEART OF WINNETKA WITH THE PEACE OF MIND AND EFFICIENCY OF A HOME WHERE EVERYTHING THAT MATTERS HAS ALREADY BEEN DONE.

925 Elm Street, Winnetka
436 Maple Street, Winnetka
$987,000
4 Beds ⋅ 2 Baths ⋅ 12552577 MLS ⋅ CLOSED Status
First time on the market in 55 years. Discover a rare opportunity in coveted East Winnetka on this generous 50 x 150 lot. This stately stucco residence offers exceptional bones and tremendous potential, ideally positioned within walking distance to top-rated schools, Metra station, and vibrant downtown shops and restaurants. Main Level: The welcoming center hall flows seamlessly through the home's well-proportioned layout. An expansive living room showcases a custom original mantel and charming sitting area with front-facing views. The formal dining room provides elegant entertaining space, while the kitchen features premium Sub-Zero and Gaggenau appliances. A separate family room with soaring vaulted ceilings creates an ideal retreat at the rear of the home. Beautiful hardwood flooring throughout adds warmth and character. Second Level: Four generously sized bedrooms and a full bathroom offer comfortable accommodations with excellent flexibility for modern living. The second floor presents an ideal canvas to create a luxurious primary suite with ensuite bath, plus two additional bedrooms sharing a full bath. Additional Features: Full unfinished basement provides valuable storage and future expansion possibilities. This is your chance to own a piece of East Winnetka history and create your dream home in one of the North Shore's most desirable locations. Bring your vision and make this wonderful property your own.

436 Maple Street, Winnetka
145 Woodley Road, Winnetka
$3,750,000
5 Beds ⋅ 7 Baths ⋅ 12542155 MLS ⋅ CLOSED Status
If My Best Friend's Wedding had a sequel...it would be filmed right here. This coastal Colonial estate set on 1.4 acres of lush, manicured grounds on premier Woodley Road offers the ultimate backdrop for timeless North Shore living. Elegant, welcoming, and effortlessly cinematic, it's the kind of home where every day feels like a scene straight out of a movie. A rare generational opportunity, this pristinely cared-for home features over 7,500 square feet of finished space & a floor plan that flows effortlessly from one sunlit room to the next. Wonderful features include a Chef's kitchen that opens to a great room, endless bluestone patios, vibrant gardens, and a sparkling pool oasis, creating an entertainer's dream. Step inside the gracious, light-filled foyer, where your eye is immediately drawn through the elegant living room picture window to the breathtaking private grounds creating instant tranquility. Formal dining room flows gracefully into the heart of the home: an inviting Chef's kitchen where classic design meets casual comfort w/quality custom cabinetry, massive island with seating for 5 and separate breakfast area. Great room accented with skylights and oversized windows naturally brings the outside in. Get cozy around the FP framed by fine built-ins creating the perfect place to unwind as this space is so inviting. To the other end of large first floor is the formal office, the ultimate private retreat with rich wood paneling & built-ins and opens to a cozy sitting room. Best yet, a spectacular sunroom with a full bath and hot tub solarium overlooking the beautiful outdoors. Expansive 2nd floor with five bedrooms including a luxury primary suite with a spacious bedroom, massive walk-in closet & crisp, sunlit white spa bath with dual vanities, soaking tub, and separate shower. 2 family size beds with ensuite neutral baths and the other 2 beds share a hall bath. Full 2nd floor laundry and awesome large play/rec space allows for many other options. Lofted finished space on 3rd level is now storage but can be studio/ 2nd office. The back staircase leads to spacious lower level with second rec room. Completing this exceptional home is a rare 4-car attached garage and an oversized mudroom/utility space waiting for your design touch. Surrounded by enchanted private gardens, sun-drenched interiors, and expansive bluestone patios, 145 Woodley Road captures the essence of quintessential North Shore living-so cinematic, it feels like a movie set... yet it's real, and waiting for you.

145 Woodley Road, Winnetka
650 Winnetka Mews Unit #310, Winnetka
$450,000
2 Beds ⋅ 2 Baths ⋅ 12496474 MLS ⋅ CLOSED Status
Fabulous opportunity to own this 2 Bed/2 Bath condo in sought after Winnetka Mews building. Conveniently located near downtown Winnetka's shops, restaurants, train, bike path, park district facilities, Winnetka Community House and beaches. The two bedroom floor plan includes a large living room, dining room, kitchen, and East facing private balcony. The primary suite is highlighted by a spacious walk-in closet and primary bathroom with double vanity, separate shower and tub. The building amenities include an exercise room, outdoor pool, elevator, heated garage parking, and outdoor guest parking. All major capital improvements have been completed while maintaining a healthy reserve balance. Additional perks include two units per floor, an onsite engineer, and newly remodeled foyer and common areas. Garage parking and Storage included in the price.

650 Winnetka Mews Unit #310, Winnetka



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