Winnetka Real Estate

Welcome to Winnetka, a charming village located in Cook County, Illinois. Known for its picturesque neighborhoods, top-rated schools, and beautiful parks, Winnetka offers a serene suburban lifestyle just a short drive away from the bustling city of Chicago.

Winnetka is a highly sought-after community for families looking to settle down in a safe and welcoming environment. The village is home to a vibrant downtown area filled with boutique shops, cozy cafes, and delicious restaurants. Residents can enjoy a variety of recreational activities, from hiking and biking along the Lake Michigan shoreline to playing a round of golf at one of the local country clubs.

With its tree-lined streets, historic homes, and strong sense of community, Winnetka embodies classic Midwestern charm. The village hosts a range of community events and festivals throughout the year, bringing neighbors together and creating a tight-knit community spirit.

For those seeking a peaceful retreat from the hustle and bustle of city life, Winnetka offers the perfect blend of small-town charm and modern amenities. Come explore all that this vibrant village has to offer and discover why Winnetka is a place that so many are proud to call 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

$1,750,000

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 redesigned from top to bottom, this home offers the feel of new construction while preserving the character of the original property. The floor plan includes 5 bedrooms, 3 full baths, and 2 half baths, with four bedrooms upstairs and a main-level bedroom with ensuite that works as a guest suite or second primary. The main floor flows easily between living, dining, kitchen, and family spaces, with two masonry fireplaces, a second family room, and a dedicated office. A fully finished basement adds recreation space, laundry, and storage, and a second laundry is located on the bedroom level. Outdoor living includes a large rear patio, generous backyard, and rooftop deck. The half-acre lot provides rare outdoor space in this Winnetka setting. Additional features include a two-car garage with EV charging and hardwood flooring throughout. Minutes from New Trier, Skokie Playfields, downtown shopping and dining, Metra, and the lakefront, 1288 Sunview is a rare combination of thoughtful design, substantial space, and an exceptional lot.

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

$2,699,000

6 Beds ⋅ 6 Baths ⋅ 12680099 MLS ⋅ ACTIVE Status

Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter.

82 Woodley Road, Winnetka

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Winnetka Real Estate

Newest Listings in Winnetka

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