$1,945,576Average Value$544Average Price per Sq Ft21Homes 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 21 days on the market compared to the national average of 56 days. The median sale price for homes in Winnetka, IL over the last 12 months is $1,915,000, up 10% from the median home sale price over the previous 12 months.
An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and
Sarah Lyons@properties Christie's International Real Estate
This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step
Jena Radnay@properties Christie's International Real Estate
Classic brick home filled with timeless character, generous living spaces and thoughtful updates on one of Glencoe's desirable tree-lined streets. A welcoming arched foyer opens to a gracious living room highlighted by refinished hardwood floors, a wood-burning fireplace and a charming office nook. The formal dining room flows seamlessly into a bright enclosed porch overlooking the backyard,
Fully Renovated 6BR 5.5BA Classic Home in Unbeatable East Kenilworth Location. This Elegant home sits on a large lot on one of Kenilworth's most serene streets. FIRST FLOOR: Elegant LR w/ Thibault Grasscloth Wallpaper & Custom Solid Wood Built Ins, Custom Handmade Mosaic Entry, Traditional DR w/ Brick Fireplace. Kitchen boasts both a Butler's Pantry and Prep Station, Quartz Countertops and
Stunning French Manor house on one of East Kenilworth's most beautiful streets. Stylish and sophisticated, this unique home is perfectly situated near the lake, train, Sears School, and New Trier High School. Luxurious landscaping envelopes the property, highlighted by a serene backyard pool. Expansive marble foyer opens to gracious living room and charming dining room. Dramatic floating
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
This 4-Bedrm and 2-Bath Cottage style home sits on a 5,267 Sq Ft lot in coveted Winnetka Hubbard Woods. This property located in top -rated schools (Hubbard Elementary) presents potential to renovate, expand or reimagine in a premier North Shore setting. The main floor plan unveils an open concept with a sprawling Family room filled with natural light next to separate sitting room with a gorgeous
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
An extraordinary "boutique hotel" living experience, impeccably situated in the heart of Winnetka. Beyond a stately solid-iron gate adorned with gold medallion accents lies a private sanctuary just 18 miles from Chicago and less than half a mile from the sandy shores of Lake Michigan. Evoking the glamour and grandeur of a Roaring Twenties estate, this remarkable residence channels the elegance of
Jena Radnay@properties Christie's International Real Estate
BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale
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
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
It is exceptionally rare to find a privately set masterpiece with sweeping views of the Winnetka Golf Course that also offers the opportunity to step directly into a freshly completed 2025/2026 designer showcase renovation. Nestled on a beautifully landscaped half-acre site overlooking the golf course, this extraordinary stone residence has been impeccably transformed through a comprehensive
Lori Nieman@properties Christie's International Real Estate
An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and
Sarah Lyons@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
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
Renovated 1 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets welcome. Close to Hubbard Woods Park, Metra, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.
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.
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 new home in the charming district of Winnetka, IL, where comfort meets convenience. This inviting property offers a wonderful living experience close to an array of local amenities, including an excellent selection of restaurants and
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 new home in the charming village of Winnetka, IL. This property offers a comfortable and inviting living space complemented by an ideal location close to dining and shopping options.This residence features spacious bedrooms
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 new home in the charming district of Winnetka, IL! This vibrant community is surrounded by great restaurants and department stores, offering convenience at your doorstep. The property is also in close proximity to notable educational
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 ideal rental opportunity in the charming district of Winnetka, IL, where convenient living meets suburban tranquility. This lovely property is surrounded by several excellent restaurants and department stores, providing a vibrant
Charming 1 bedroom apartment in Winnetka! Unit features hardwood floors, spacious living area. Electric heat. Close to Metra, Hubbard Woods Park, grocery, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.
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 new home in the desirable district of Winnetka, IL. This charming property offers a perfect blend of comfort and convenience, ideal for those looking to enjoy a vibrant community life. The residence features spacious bedrooms
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 new home in vibrant Winnetka, IL! This charming property offers a comfortable living experience in a picturesque neighborhood, surrounded by fantastic dining options and retail stores. With easy access to prominent educational
Charming 1 bedroom apartment features hardwood floors, updated kitchen and bath. Pets welcome. Close to Metra, restaurants, grocery and more. Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.
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