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Homes for Sale In Winnetka

Winnetka is an exclusive suburban village in Cook County, Illinois. Located along the shores of Lake Michigan, Winnetka covers a total area of 3.89 square miles, bordered by the towns of Glencoe, Northfield, Wilmette, and Kenilworth. Sitting just 17 miles from downtown Chicago, residents can easily access all the metropolitan services and amenities in the area through I-94 (Eden’s Expressway) or the Metra commuter rail.

With its tree-lined, pedestrian-friendly streets, architecturally stunning homes, abundant parks, and recreational facilities, Winnetka is renowned for its natural beauty and upscale, family-friendly lifestyle. It is also considered the “Crown Jewel of the North Shore”— its gorgeous landscape has served as the backdrop for iconic American films like Home Alone and The Breakfast Club.

Winnetka’s visual appeal is only the tip of the iceberg. This charming village also provides its residents with the best quality of life possible. Publications like CNN Money and 24/7 Wall St. has called Winnetka the best suburb in Illinois and the second-best small town to live in in the United States due to its commuter-friendly transportation system, highly educated workforce, and thriving local business districts.

This coveted North Shore community’s cultural heritage dates to the late 19th century when the Patterson family built a tavern in the area. Succeeding settlers, including the Pecks, all put a stamp on Winnetka’s history and shaped it to become one of the most affluent locales in Illinois.

Where is Winnetka

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A Brief HistoryOf Winnetka IL

Winnetka started out as a small village of over a hundred people and three hundred platted acres under the New Trier Township. Although the Pattersons were its earliest settlers, Charles and Sarah Peck are often credited as the “founders” of Winnetka. Sarah provided its name – after a Native American phrase that meant “beautiful land” – and established its first school. Meanwhile, Charles worked with Walter S. Gurnee, the president of the newly formed Chicago & Milwaukee Railroad, in developing Winnetka as a prosperous suburban community.

The railroad provided Winnetka with a direct link to the city of Chicago. And with its natural landscapes and pristine lakefront location, the village soon became a respite for weary urban dwellers who wanted a break from the busy and crowded city. This led to a population boom. Around the same time, the village-owned Municipal Electric Utility Plant ensured Winnetka’s self-sufficiency, financing the construction of its Village Hall as well as the salaries of local teachers during the Great Depression.

Preserving its small-town character

The spirit of community service and civic duty has been a part of Winnetka’s identity from the very beginning. The Pecks spearheaded the planting of donated elms along Elm Street, and its canopies continue to provide shade for Winnetka residents until today. The founding pair also donated Village Green to the community, which continues to stand as the village’s spiritual center and host to many of Winnetka’s local events and festivities.

Like its founders, many of Winnetka’s early residents were well-educated and progressive, aligning themselves with the social reformist ideals of the time. At the height of its population boom, they established the Winnetka Caucus to ensure citizen control over the future development of the village. One of its main priorities is maintaining Winnetka’s tranquil suburban environment. This led to the creation of local bylaws such as banning the public sale and consumption of alcohol and lowering the railroad tracks for the safety of its residents.

Living alongside history

After more than a century of meticulous planning and preservation, Winnetka continues to enjoy the beautiful natural scenery that attracted its first residents, in addition to its family-oriented neighborhoods, stunning historical architecture, and vibrant local restaurants and shopping districts.

Winnetka’s rich history and cultural heritage are both deeply present the local community life in the form of local attractions. None is as important as the aforementioned Village Green, which serves as Winnetka’s spiritual center. The park covers 3.36 acres and houses a cenotaph or war memorial designed by architect Samuel S. Otis, as well a stone memorial that commemorates Dr. Martin Luther King’s 1965 speech in Winnetka.

Another green space integral to community life is the Winnetka Park District. Established in 1904, it is one of the oldest park districts in the state of Illinois. To date, the Winnetka Park District oversees over 27 parks, 5 lake beaches, and several sports facilities, including golf, tennis, ice skating and hockey, and paddle tennis.

One of the best ways to see and experience Winnetka’s natural beauty is by exploring the Green Bay Trail. This 2.24-mile asphalt path traverses through the village all the way from Kenilworth to Glencoe. What makes the Green Bay Trail a unique attraction is its past as former tracks of the Chicago and Milwaukee Railway. Because of numerous accidents at its grade crossings, it was grade separated between 1937 and 1942. The track depression left by the excavation was repurposed and transformed into this scenic and walking trail.

Finally, history and education intertwine at The Crow Island School. Registered as a National Historic Landmark in 1990, this pioneering school opened in 1938 and was designed by notable modernist architects Eliel and Eero Saarinen. The Crow Island School is home to the very first jungle gym, invented in 1920 by Winnetka resident and lawyer Sebastian Hinton.

Homes for SaleWinnetka, IL

Single-family homes, luxury estates, and lakefront properties dominate Winnetka’s real estate market. Four- to five-bedroom houses are the norm, and property sizes can fall anywhere between less than an acre two acres and beyond depending on the location. Large estates can be found along Sheridan Road, nearest to Lake Michigan, whereas smaller to mid-sized residential properties are more common near the town’s center and shopping districts.

Winnetka is one of the most historically preserved suburban areas in the country. The housing stock has many properties dating before World War II. A substantial percentage (24.44%) of homes were also built from 1940 to 1969. For homebuyers looking for more contemporary homes, Winnetka also has a considerable number of new construction homes and newly renovated properties.

Architecture and suburban planning

The beauty of Winnetka stems not just from its natural landscapes, but also from its assemblage of houses and canopied streetscapes. Residents can easily walk to the village’s recreational centers, nature trails, or lakefront beaches. This walkability and convenient accessibility extend all the way to Winnetka’s bustling downtown area, making it the perfect town for retirees, young families, and professionals.

But the “crowning glory” of North Shore’s Crown Jewel is its architecturally diverse selection of homes. As one article from Chicago Tribute noted, “Winnetka’s houses comprise a field guide to architecture, from Dutch Colonial to Foursquare to Tudor.”

Many historic estates and luxury homes in Winnetka are designed by renowned architects, including George Washington Maher, an influential figure in the Prairie School movement and the American Arts and Crafts design, and Howard Van Doren Shaw, a leader in the American Craftsman movement.

Living In Winnetka, IL

The weather

The state of Illinois has a continental climate, meaning that its cities and towns experience warm, breezy summers and cold, snowy winters. Spring and fall are the most pleasant seasons of the year, providing more moderate temperatures than the summer or winter seasons.

Since Winnetka sits right along Lake Michigan, residents enjoy cooler summers and warmer winters due to the large thermal mass of the lake. If you’re someone who enjoys hiking or biking during the summer, you’ll be glad to know that the nearby lake brings cool breezes that can combat the heat. The lake also makes Winnetka quite the paradise for avid winter sports enthusiasts as it contributes to increased snowfall.

Economy & Employment

Winnetka’s economy is largely driven by STEM, finance, and educational services and industries. Compared to other towns and cities in the US, this village also has a high number of residents working in law, management, and business and financial operations. With a workforce consisting of mostly professionals and executives, Winnetka has a median household income of $250,000+, which is more than the national average.

The Winnetka-Northfield Chamber of Commerce (WNCC) handles the local business and civic community in the village, particularly when it comes to promoting Winnetka’s economic growth and development. The Chamber organizes and sponsors many events to support homegrown businesses, such as the Sidewalk Sale, the Annual Red Invitation Sale, and Annual Recognition Lunch.


Winnetka is a commuter-friendly village. There are three Metra train stations that run through the whole community, so most residents can easily walk to one of them. The Pace Suburban Bus service also provides two bus routes through the area, which stops at the CTA Purple Line. For those who prefer to drive, downtown Chicago and other areas can be accessed through I-94 (Eden’s Expressway).


Winnetka Public Schools, also known as Cook County School District 36, is one of the leading school districts in the country when it comes to progressive education. Throughout its long history, Winnetka Public Schools have served as the educational model for comprehensive child development. This district services children from kindergarten to the eighth grade, including schools like:

After completing middle school, high school students can attend the New Trier Township High School, a nationally recognized high school with award-winning academic programs.

Other private schools in Winnetka include:

Recreational activities and attractions

From hiking in forest trails to browsing antique pieces, there are countless things to do in Winnetka. Here are some places you can check out:

  • Winnetka Golf Club. One of Chicagoland’s premier public golf facilities, Winnetka Golf Club is home to an 18-hole championship golf course designed by architect William H. Langford. Known to be the true test of target golf, avid players can practice their skills on the greens, or take advantage of the facility’s full-service clubhouse.
  • Skokie Lagoons. What used to be a huge marsh is now an 894-acre Forest Preserve site managed and operated by the Forest Preserve District of Cook County (FPDCC). The Skokie Lagoons is a one-of-a-kind destination for wildlife explorers and outdoor enthusiasts, with its vast selection of picnic areas, hiking and horseback riding trails, fishing spots, and birdwatching opportunities.
  • Winnetka beaches. Aside from operating a total of 27 parks throughout the village, the Winnetka Park District also maintains over 23 acres of park land adjacent to the beautiful Lake Michigan. This includes three swim beaches, a dog beach, and a boat launch and sailing center. However, take note that daily admission is only available from mid-June to mid-August, to protect the lake’s natural balance.
  • The Winnetka Historical Society (WHS). Winnetka is a village with a deep historical background, and you can learn more about it at the Winnetka Historical Society Museum at 411 Linden Avenue. You can also visit the Schmidt-Burnham Log House in Crow Island Woods (1140 Willow Road), where you can see what life was like in the 1850s.
  • Winnetka Community House. This iconic village structure is a place where the past and present collide. This historic site is part of the National Register of Historic Places and hosts numerous local events such as Antiques + Modernism (a national acclaimed antiques show) and performances from the Children’s Theatre of Winnetka, Ballet Entre Nous, and Village Follies.

Shopping & dining

Winnetka is home to four shopping districts, each with its own distinct character and unique shopping and dining options:

  • East Elm Shopping District. The East Elm Shopping District features a seamless blend of traditional and modern design, and home to several upscale boutiques, jewelry stores, and antique shops.
  • Hubbard Woods Shopping District. Known for its “Old World” charm, the Hubbard Woods Shopping District is a great place to shop and relax, with its lovely courtyards and Tudor-style architecture.
  • West Elm District. If you’re looking for great outdoor dining options, West Elm District is the place to be. You can also find several boutiques and antique shops in this area.
  • Indian Hill. Located in the southeast corner of Winnetka, this shopping district consists mostly of service businesses. But its centerpiece is Chef Michael Lachowicz’ George Trois Group, which offers two avant-garde dining experiences inspired by French and American cuisine.

Special events

From farmer’s markets and parades to music festivals and art and wine walks, there’s always a fun event happening in Winnetka. Here are some festivals and celebrations you can look forward to:

Explore Winnetka Real Estatewith Cory Green

Whether you’re planning to buy or sell a home in Winnetka, it’s important to work with someone who not only has your best interests in mind. They also must have the skills and expertise to make it all happen. I’m Cory Green, a long-time resident of the North Shore area and your go-to real estate broker.

Having worked in the real estate industry for 18 years, I have intimate and up-to-date knowledge of Winnetka’s local real estate marketplace, as well as a wealth of experience in real estate financing, construction, and contract negotiation. To date, I have over $4 billion successful real estate transactions under my belt.

With my wide network of professional resources and unique online, I make sure that all my clients – whether they’re looking for their dream home or planning to sell their home for top dollar – receive exceptional and personalized services throughout their real estate journey.

Work smart by working with the best in the North Shore area. Get in touch with me today by calling 312.485.0897 or by emailing [email protected].

The Best Highlights of the Winnetka

Contact Cory Green

When it comes to discovering the finest properties and enjoying the best lifestyle that Chicago’s North Shore has to offer, there is no better person to have by your side than trusted real estate expert Cory Green. You are sure to be in excellent hands when you work with someone who has personally been responsible for over $4 billion worth of real estate transactions, ranging from high rise development and construction projects to single family homes sales; including notable landmark projects in his local community.

Banking on two decades of experience in the Chicagoland real estate market, I confidently provide all of my clients with dedicated, personalized, and comprehensive white-glove service. Whatever you need to achieve in your real estate goals, you can count on me to deliver it.

Are you excited to begin your home search across these outstanding North Shore suburbs? Contact me to discuss your needs and preferences in an ideal house. I will provide you with the latest and most comprehensive information you need to start your search, and we can schedule a virtual home tour at your earliest convenience.

Listing your North Shore home? Allow me to lend my expertise, as well. From the essential steps in preparing your home to sell, to setting an attractive market-based asking price, to negotiating toward the best top dollar deal available for your beloved property, I will work relentlessly to make sure that you get only the most satisfying results.

If you are all set to begin your real estate journey in Chicago’s North Shore, all you need to do is let me know. Feel free to call me at 312.485.0897 or ask for more information via email at cory(dotted)green(at)compass(dotted)com.

With Cory

Cory offers an unparalleled level of service to his clients, and he would love to be a resource for you. Whether you are buying, selling, renting or investing; his level of professionalism and expertise will exceed your expectations and he will always help you achieve your goals.


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