$1,975,478Average Value$546Average Price per Sq Ft15Homes For Sale
'Beautiful land' in a suburb on Lake Michigan
The name Winnetka roughly translates to "beautiful land" in the Potawatomi tribe's language. This North Shore village bordering Lake Michigan has the benefit of beaches, parks and the surrounding Forest Preserves of Cook County. It's only about 15 miles to downtown Chicago, with access via multiple Metra train stations. "The area has always been the draw for those that work in the Loop," says Daniel O'Donoghue, a real estate broker with Compass.
O'Donoghue grew up here in Winnetka, and his grandparents lived in the neighboring village of Northfield, which shares some similarities and services with Winnetka. He's served the communities throughout his 20-year career in real estate. The population is about 12,700, yet Winnetka, once farmland, maintains its small-town character, with community and school-based activities and a focus on local businesses. According to the CAP Index, Winnetka receives a crime score of 1 out of 10, less than the U.S. average score of 4.
Winnetka is named after the Native American phrase meaning “beautiful land.”
Centennial Park in Winnetka has a perfect view of Lake Michigan.
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Multimillion-dollar luxury, Cape Cods and condos
Since development sprang up from the lake, there are a greater number of older homes here than inland. Included are early 1900s to 1920s farmhouses, bungalows and Colonial Revival and Tudor Revival houses. Some are sizable, 3,000 to 6,000 square feet, with prices above $1.5 million. In addition to vintage properties, the multimillion-dollar price range includes newer but equally stylish and spacious homes built from the late 1990s until the present.
Generally, the closer to the waterfront, the higher the prices. Among the luxe properties are French-style chateaus and English-inspired manors. In 2023, a lakeside Spanish-style villa with five bedrooms and over 6,000 square feet on a lot of over two acres sold for more than $12 million. And that wasn't the only sale at that price.
A variety of homes built in the second half of the 20th century are more typical of suburbia, as Cape Cods, ranch-style houses and condominium buildings were set in place. A condo under 1,000 square feet might cost under $250,000, and three- to four-bedroom homes of 1,600 to 2,500 square feet go from about $750,000 to over $1 million. O'Donoghue says homeowners invest in remodels and renovations. "There's been a lot of redevelopment over the past several years."
Several streets like Oak, Cherry, Birch, Chestnut and Linden might appeal to families in particular. "A lot of folks in Winnetka like living on the tree streets because they are more walkable and close to schools," O'Donoghue says.
Winnetka's Cape Cod homes have attached garages with driveways for comfortable parking.
The Indian Hill neighborhood of Winnetka is full of large, beautiful homes with varying styles.
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Lloyd Beach, the Green Bay Trail and more
Water access is the main feature on the village's east side, with a handful of beaches just minutes from home. Lloyd Beach has a boat launch and paddleboard rentals. The Winnetka Waterfront 2030 included landscape restoration and a new breakwater system at the beach in 2020 and 2021. Season pass holders have daily access to the beaches from late May until early September.
Other outdoor enjoyment is found in the community parks and nearby nature preserves, like Erickson Woods, with a 4-mile trail linking the Skokie River. O'Donoghue says locals visit for fishing, kayaking and canoeing. "There are some really nice running and biking trails that go all around the lagoons," he says, noting that they extend as far as the Chicago Botanic Garden, about 5 miles away in Glencoe.
Another cyclist and hiker favorite is the Green Bay Trail, a paved path straight through the center of Winnetka. Other leisure and athletic sites include the public Winnetka Golf Club, the private country club Indian Hill, an ice arena and a platform tennis club. "A.C. Nielsen Tennis Center is where a lot of stuff happens," O'Donoghue says. Family friendly sports activities like community leagues are a cherished part of the Winnetka lifestyle.
Green Bay Trail in Winnetka is a great place for residents to enjoy the outdoors.
Lloyd Beach in Winnetka has a boat launch and paddleboard rentals.
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Downtown Winnetka and small businesses
In downtown Winnetka, along Elm Street and Green Bay Road, there's a focus on local businesses. "The downtown has been there a long time and is centered around the Metra," O'Donoghue says. "It's walking-friendly."
Spots for dining include Fred's Garage for sandwiches and tacos; Hometown Coffee & Juice for smoothies and bagels; and Pomeroy, offering French cuisine, brunch and wine tastings.
Ellen's on Elm is a spot to pick out gifts. The shelves are full at The Book Stall, which hosts author events onsite and at public libraries or other local venues. The Grand Food Center and Lakeside Foods stock stables and specialty items to fulfill many a shopping list. For big-box stores like Target and Costco, residents head west of Interstate 94.
Hometown Coffee is a popular spot in Winnetka, especially on a nice day.
Spirit Elephant is one of the fantastic restaurants available in Winnetka.
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Schools divided by levels; New Trier High
Kids may attend public schools in the Winnetka School District 36, which includes Crow Island School, serving prekindergarten through fourth grade; The Skokie School, for fifth through sixth grades; and Carleton W. Washburne School, for seventh and eighth grades. Each has an A grade from Niche. "Winnetka is a progressive education school district," O'Donoghue says. "There's a different philosophy behind the schools." For one, a letter-based grading system is not used until seventh grade.
Next up, A-plus New Trier Township High School enrolls students from Winnetka, Northfield and Glencoe. The upper-level campus is here in Winnetka, and Northfield has the one for freshmen.
Other public school districts in the area include Avoca School District 37, A-minus, and Wilmette School District 39, A. Also in Wilmette is a private option, Loyola Academy, a Jesuit Catholic high school graded A-plus.
New Trier Township High School is an excellent public school located in Winnetka.
Carleton Washburn School in Winnetka has close to 400 students in attendance.
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Three Metra stations, Pace bus routes
The village has the advantage of three Metra stations: Winnetka, Hubbard Woods and Indian Hill. All are on Green Bay Road, with rail service on the Union Pacific North Line, which goes from the city's Ogilvie Transportation Center to Kenosha Station, Wisconsin's only stop. To the west of the village, Interstate 94, or the Edens Expressway, is the quickest route to drive into Chicago.
Pace Suburban Bus Route 423 provides service from Wilmette to Chicago, with stops including Winnetka Station, Winnetka Library, and both New Trier High School campuses. The route goes through Northfield, Glenview, and Niles, and there are L station stops on either end. Route 213 – Green Bay Road hits Winnetka on the way from Highland Park to Howard CTA Station. A paratransit reservation system for portions of north suburban Cook County is also available.
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On average, homes in Winnetka, IL sell after 20 days on the market compared to the national average of 55 days. The median sale price for homes in Winnetka, IL over the last 12 months is $1,985,000, up 15% from the median home sale price over the previous 12 months.
Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature
Beverly Smith@properties Christie's International Real Estate
Charming House in Winnetka with Timeless Appeal Welcome to this charming four-bedroom, 1 1/2 bath Winnetka home that beautifully blends classic character with comfortable, inviting living spaces. Warm and welcoming from the moment you walk past the stately over four-hundred-year-old Burr Oak in the front yard, this home offers a wonderful combination of livability and an in-town location.
New magnificent transitional home with approximately 11,000 square feet finished space. Exterior is constructed of brick and limestone with slate roof which represents timeless construction. Close to Plaza del Lago with its numerous shops and restaurants, Kenilworth beach, schools and train the house features 7 bedrooms, 8.1 bath, 3 fireplaces, spectacular kitchen with top-of-the-line appliances
Milena Birov@properties Christie's International Real Estate
Phenomenal value as this finely built newer construction home privately set with serene panoramic Winnetka Golf Club vistas just hit "elevated luxury" status with an impeccable 2026 no expense spared rehab. Starting off with the new stunning Chef's kitchen that radiates with extra-thick Taj Mahal honed quartzite c-tops, Perrin & Rowe fixtures, Frankie sink, Visual Comfort brushed brass pendants &
Jena Radnay@properties Christie's International Real Estate
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,
Michael Mitchell@properties Christie's International Real Estate
A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins.
Anne MaitlandJameson Sotheby's International Realty
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
**Multiple Offers Received** Highest and Best due Tuesday 9/15 by 9am** A rare expression of extraordinary North Shore living, this quintessential red-brick Colonial sits on a 100' x 175' double lot (.39 of an acre) on coveted Hill Terrace, one of Winnetka's prettiest private lanes, in an A+ walk-to-everything location. Designed by prolific architect Bertram A. Weber, this much-loved residence
Susan Sullivan@properties Christie's International Real Estate
Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after
Eugene Fu@properties Christie's International Real Estate
Enjoy an East Winnetka lifestyle on a beautifully landscaped expansive .3 acre all brick home in an ideal location, only blocks to Tower Road beach, Hubbard Woods/Winnetka shops and restaurants, schools, parks, and train. This sophisticated Georgian offering a great circular floorplan, grandly scaled rooms filled with natural light, fabulous outdoor spaces with a fully fenced yard, and an
The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as
Jena Radnay@properties Christie's International Real Estate
Reduced new price for the land is more than $100,000 less than the original !! Rare chance to own 1.36 acres of land on beautiful Winnetka rd will provide you endless possibilities to build your dream home. Incredible opportunity to collaborate with experienced luxury builder or bring your own builder. Winnetka High School District. Amazing location- close to Northfield Park District,Westfield
A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value
Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature
Beverly Smith@properties Christie's International Real Estate
Renovated 1 bedroom in a well run vintage two story building! . Hardwood floors. Bright apartment w large picture windows, Eat in kitchen with dishwasher and microwave. Large bedroom (with closet) fitting for even a king size bed. Large bathroom.Heat and water included. Clean and tidy laundry room in building plus bike storage. Classic, original details combine with fresh updates to
Winnetka - 2 Bedroom 1 Bathroom **Charming Apartment Living in Fabulous Downtown Winnetka!** Modern comfort meets the vibrant lifestyle of downtown Winnetka. Nestled in an unbeatable location, this beautifully updated apartment offers an ideal balance of style and convenience, perfect for urban dwellers seeking a welcoming retreat. **Key Features:** - **Gourmet Kitchen**: Step into your renovated
Actual Unit # *E811-209* Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Comfortable and well-maintained apartment located in a convenient Chicago-area neighborhood. This unit offers a functional layout, spacious living areas, and easy access to shopping, dining, public transportation, parks,
Outstanding one bedroom, one bathroom in Winnetka features newer kitchen with dishwasher, large combination living and dining rooms, spacious bedroom, great closet space, hardwood floors, rehabbed bathroom, laundry room in building, and pets are welcome. Steps to Hubbard Woods Metra stop, and a block to Tower Road Park Beach! UA1701 Won't Last Long!
Notable two bedroom, one bathroom in the heart of downtown Winnetka features heat included, rehabbed kitchen with stainless steel appliances, dishwasher, spacious living area, large equal sized bedrooms, awesome closet space, hardwood flooring throughout, free laundry in building, storage, and cats are welcome! Steps to Winnetka Metra stop! Won't Last Long!
Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry in-unit. Pet friendly building. Great location close to Dwyer Park, Metra, restaurants and shopping! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.
AVAILABLE NOW! Remarkable two bedroom, one bathroom in beautiful Winnetka courtyard building features rehabbed kitchen, spacious living area, large bedrooms, great closet space, rehabbed bathroom, hardwood floors throughout, laundry room in building, and pets are welcome! Steps to Hubbard Woods Metra stop and a block to the Beach! UA1701 Won't Last Long!
AVAILABLE OCTOBER! Handsome two bedroom, one bathroom in heart of downtown Winnetka features rehabbed kitchen with espresso cabinets, stainless steel appliances, dishwasher, large combination living and dining rooms with ceiling fan, spacious bedrooms, great closet space, rehabbed bathroom, hardwood floors throughout, laundry in unit, and pets welcome! Steps to Winnetka Metra stop, shops,
AVAILABLE NOW! Tremendous two bedroom, one bathroom in beautiful Winnetka courtyard building features newer eat in kitchen with dishwasher, large combination living and dining rooms with decorative fireplace, spacious bedrooms, great closet space, newer bathroom, hardwood floors throughout, laundry room in building, and pets are welcome! Steps to Hubbard Woods Metra stop and a block to the Beach!
Outstanding two bedroom, one bathroom in the heart of downtown Winnetka features heat included, rehabbed kitchen with stainless steel appliances, dishwasher, spacious living area, large equal sized bedrooms, awesome closet space, hardwood flooring throughout, free laundry in building, storage, and cats are welcome! Steps to Winnetka Metra stop! Won't Last Long!
AVAILABLE NOW! Peaceful one bedroom, one bathroom in beautiful Winnetka courtyard building features newer kitchen with stainless steel appliances, dishwasher, large combination living and dining rooms with ceiling fan, spacious bedroom, great closet space, newer bathroom, hardwood floors throughout, laundry room in building, and pets welcome! Steps to Hubbard Woods Metra stop and a block to the
Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your next home in the charming district of Winnetka, IL! This delightful property offers a comfortable living space near a variety of local amenities, including popular restaurants and department stores. Enjoy the convenience of nearby
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