Winnetka Real Estate

Welcome to Winnetka, Illinois – a picturesque village nestled along the shimmering shores of Lake Michigan in Cook County. Known for its charming tree-lined streets and stunning historic architecture, Winnetka exudes a sense of community that is both inviting and vibrant. With a population of just over 12,000 residents, this idyllic suburb offers a perfect blend of small-town charm and modern conveniences.

Winnetka is celebrated for its top-rated public schools, making it an ideal place for families seeking quality education. The community is home to several parks and recreational facilities, including the expansive Hubbard Woods Park and the scenic Winnetka Beach, where residents can enjoy sun-soaked summer days and breathtaking lake views. The village also boasts a rich cultural scene, with art galleries, local boutiques, and a variety of dining options that cater to every palate.

For those who appreciate a strong sense of community, Winnetka hosts numerous events throughout the year, from summer concerts in the park to festive holiday celebrations that bring neighbors together. With easy access to the Metra train line, commuting to downtown Chicago is a breeze, allowing residents to enjoy the vibrancy of the city while returning to the tranquility of their suburban oasis.

Whether you’re drawn to the stunning natural beauty, the exceptional schools, or the warm community spirit, Winnetka offers a lifestyle that is both enriching and fulfilling. Explore the charm of this delightful village and discover why so many have chosen to call Winnetka home.

Newest Listings in Winnetka

$2,100,000

4 Beds ⋅ 6 Baths ⋅ 12798477 MLS ⋅ ACTIVE Status

Welcome to this exquisite, sun-drenched 4+1 bed, 5.1 bath luxury home on an oversized lot (50x232) at the Winnetka/Glencoe border. Located on a beautiful tree lined cul-de-sac and adjacent to the Green Bay trail, this home sits across the street from Glencoe Park. The moment you walk in, you are greeted by a bright formal living room featuring one of the home's four fireplaces, flanked by an adjacent office adorned with beautiful, oversized bay windows. Designed for seamless modern living, the main level flows into a sophisticated formal dining room, an open-concept kitchen, breakfast room and family room overlooking expansive backyard. The main level features a light, neutral palette and newer light fixtures throughout. The second floor is a private retreat where all four bedrooms feature dedicated en suite baths, and two enjoy the luxury of private decks. All new hardwood flooring throughout this level along with a fresh paint. Spacious primary bedroom features large walk in closet and elegantly renovated bathroom with double vanity and a breathtaking walk in shower. A dedicated second-floor laundry room includes a newer washer/dryer. Fully finished basement adds incredible value with a huge recreation room, a full bath, bar and a flexible 5th bedroom/home gym. Enjoy cozy evenings anchored by the home's 4 distinct fireplaces. The outdoor oasis features an oversized paver patio, massive yard, and an oversized 2-car garage. Impeccably maintained with newer appliances, wine cooler, updated mechanicals, and a central vac system, this home offers total peace of mind. Unbeatable location just minutes from Hubbard Woods shopping, dining, and the Metra train.

285 Woodlawn Avenue, Winnetka

$3,499,000

6 Beds ⋅ 7 Baths ⋅ 12797319 MLS ⋅ ACTIVE Status

Extraordinary luxury new construction in a prime Winnetka location, with anticipated completion Summer 2027. Set on over a quarter acre, this exceptional residence will offer approximately 5,500 square feet with 8 bedrooms, each offering en-suite bath access, and 7 baths, blending elevated craftsmanship, timeless finishes, and thoughtful design for sophisticated yet comfortable living. Soaring 9'6" ceilings, engineered hardwood flooring, and designer ceiling details create an impressive backdrop for beautifully appointed interiors. The chef's kitchen will feature Sub-Zero and Wolf appliances, custom cabinetry, quartz countertops, a 10-foot island with seating, and a fully equipped butler's pantry with wine refrigeration. Opening seamlessly to the family room with a custom fireplace and built-ins, this inviting gathering space is designed for effortless everyday living and entertaining. A dramatic 12-foot folding door system connects the interior to the backyard, creating an exceptional indoor-outdoor living experience. An attached two-car garage with an EV charger adds modern convenience. Ideally located moments from downtown Winnetka, the train, parks, schools, and Lake Michigan. A rare opportunity to personalize finishes and create your dream home in an outstanding North Shore setting. Please note: Interior photos showcase the builder's previous project.

795 Pine Street, Winnetka

$1,385,000

4 Beds ⋅ 3 Baths ⋅ 12791044 MLS ⋅ ACTIVE Status

Nestled on one of Winnetka's most desirable streets in Hubbard Woods, this beautifully maintained brick residence offers a timeless blend of classic charm, thoughtful design, and exceptional outdoor living in the heart of Winnetka. Designed for both everyday comfort and effortless entertaining, the home features a welcoming, connected floor plan with a gracious flow between the living and dining rooms. Hardwood floors, plantation shutters, and refined details add warmth and character, while a wood-burning fireplace framed by built-in cabinetry creates an inviting focal point in the living room. The adjoining dining room connects seamlessly to the updated chef's kitchen, featuring premium appliances and abundant workspace. Just beyond, the sun-filled family room is surrounded by walls of windows and glass doors that bring the outdoors in and open to a beautifully landscaped backyard retreat. A versatile first-floor bedroom and full bath offer exceptional flexibility for guests, extended family, a private home office, or au pair accommodations. Upstairs, the primary suite features a newer private en-suite bath, while two additional well-proportioned bedrooms share a fresh, full hall bath. The private outdoor oasis is a true highlight, featuring an expansive newer deck with built-in seating, a charming pergola, and a patio perfect for al fresco dining, summer gatherings, or quiet moments surrounded by nature. The finished lower level provides valuable additional living space, ideal for recreation, fitness, play, and abundant storage. A detached two-car garage adds everyday convenience, while the home's surprisingly spacious layout offers more room than meets the eye. Ideally situated within walking distance of Hubbard Woods School, the train, parks, boutique shopping, dining, and the lakefront, this special property pairs an exceptional neighborhood setting with inviting indoor-outdoor living. A wonderful opportunity to enjoy the charm, convenience, and lifestyle that make Winnetka and the North Shore so desirable.

1450 Asbury Avenue, Winnetka

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 12789167 MLS ⋅ ACTIVE Status

381 Linden Street, Winnetka

$285,000

2 Beds ⋅ 1 Baths ⋅ 12784655 MLS ⋅ ACTIVE Status

Rarely available and ideally located in the heart of Hubbard Woods, this charming 2-bedroom, 1-bath condo is the largest unit in Winnetka Manor. Just steps from the Metra, shops, restaurants, parks, Lake Michigan, and the bike path, this home offers an exceptional blend of character, comfort, and convenience. The inviting layout featuring a spacious living room, separate dining room, and two generous bedrooms. Hardwood floors, fresh neutral paint, and abundant natural light enhance the timeless appeal. The updated kitchen features granite countertops and stainless-steel appliances, while the refreshed bath, decorative fireplace mantel, California Closets throughout, and a walk-in primary closet add thoughtful touches. Winnetka Manor is a well-maintained community. Terrific move-in-ready home!

1097 Merrill Street Unit #G2, Winnetka

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 12779584 MLS ⋅ ACTIVE Status

1140 Oakley Avenue, Winnetka

$1,995,000

5 Beds ⋅ 5 Baths ⋅ 12786632 MLS ⋅ ACTIVE Status

Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been redeveloped from top to bottom with a focus on design, functionality and quality, creating a home that feels entirely new while maintaining the character and setting of the original property. The spacious floor plan offers 5 bedrooms, 3 full bathrooms and 2 half bathrooms, including four bedrooms upstairs and a fifth bedroom with ensuite bath on the main level that can function as a second primary suite. Two beautiful masonry fireplaces serve as focal points within the home, adding warmth, character and a timeless architectural element to the thoughtfully designed spaces. Multiple living spaces include two family rooms, a dedicated office and a fully finished basement, providing exceptional flexibility for today's lifestyle. The home's design creates an easy flow between the living, dining, kitchen and family spaces, while the main-level bedroom offers versatility as a guest suite, bedroom or second primary. The upper level features a spacious primary suite along with three additional bedrooms and a full hall bathroom. A convenient second laundry area is located on the bedroom level, while the fully finished basement provides additional recreation and living space, along with laundry, storage and mechanical areas. Outdoor living is a major highlight, with an expansive back patio, generous backyard and rooftop deck overlooking the property. The huge half-acre lot provides an uncommon amount of outdoor space in this Winnetka setting and is ideal for entertaining, relaxing or enjoying time with family and friends. Additional features include a two-car attached garage with EV charging hookup, beautiful hardwood flooring and thoughtfully designed spaces throughout. Set in an exceptional Winnetka location, 1288 Sunview is just minutes from New Trier schools, Skokie Playfields, parks, downtown shopping and dining, Metra and the lakefront. A rare combination of thoughtful design, substantial living space, architectural character and an exceptional half-acre setting, 1288 Sunview has been completely reimagined for modern living and is truly move-in ready.

1288 Sunview Lane, Winnetka

$1,995,000

12780362 MLS ⋅ ACTIVE Status

A rare offering on one of East Winnetka's most desirable streets, just two blocks from Lake Michigan. This exceptional property presents a unique opportunity to either thoughtfully renovate an existing home or create a custom residence with the potential for approximately 8,400 square feet of finished living space. Set on a beautiful, private lot surrounded by lush greenery, the property offers the perfect canvas for reimagining a home in an extraordinary setting. With no comparable lots currently available, and neighboring properties valued at over $5 million, the possibilities are truly exceptional. Enjoy an easy walk to downtown Winnetka, Greeley School, New Trier High School, the Metra train, Lake Michigan, parks and more. A rare opportunity to bring your vision to life in an unmatched location, whether through a beautiful renovation or a custom new build. Existing home is sold as-is, with no inspections.

510 Ash Street, Winnetka

$1,995,000

5 Beds ⋅ 3 Baths ⋅ 12775682 MLS ⋅ ACTIVE Status

510 Ash Street, Winnetka

$1,750,000

4 Beds ⋅ 6 Baths ⋅ 12783024 MLS ⋅ PRICE CHANGE Status

Rarely available first floor primary! Unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners. Owner extremely motivated!!!

42 Woodley Road, Winnetka

$3,999,000

5 Beds ⋅ 9 Baths ⋅ 12774096 MLS ⋅ ACTIVE Status

1128 Mt. Pleasant Road, Winnetka

$2,595,000

12213495 MLS ⋅ ACTIVE Status

Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own architect and builder, or take advantage of thoughtfully designed plans already in the final stages of the permitting process. With multiple PINs and over 63,000 square feet of land, the possibilities are endless. This property presents the rare opportunity to create a private estate with unparalleled scale, luxury, and privacy. Nestled among some of the North Shore's finest homes, the setting perfectly balances serene seclusion with everyday convenience. Located within the nationally acclaimed New Trier High School District, the property is just minutes from the boutiques, restaurants, and amenities of both Winnetka and Wilmette. Bring your vision and your grandest ideas to this remarkable offering.

61 Woodley Road, Winnetka

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Winnetka Real Estate

Newest Listings in Winnetka

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