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Winnetka Homes for Sale and Rent

Is it a buyer's or seller's market for Winnetka Homes? Learn more

Winnetka is a North Shore community of homes 16 miles to downtown Chicago. Winnetka homes for sale range from historical lakefront estates on Sheridan Road to traditional homes in the village, and new contemporary homes with dramatic views of the ravines. Winnetka is noted for its beaches and 23 community parks, a boating beach, an 18-hole public golf course, highly respected public and private schools, and a charming village that is home to many boutiques and cafes. Metra's UnionPacific North Line commuter trains to Chicago's downtown business district are found at Elm Street, Indian Hill, and Hubbard Woods stations.  Read more

Winnetka IL Home

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Winnetka Homes for Sale

$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
$5,000,000 - $10,000,000
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Photo of Listing #12285558

800 Tower Road, Winnetka, IL - $1,417,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 2,637 SQFT
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Welcome To This Cozy Cape Cod Situated Right Off Tower And Sheridan Rd. Just Steps Away From The Beach, This Home Exudes Warmth And Timeless Appeal. The Prime East Winnetka Location Captures The Essence Of North Shore Living. The Living/dinning Ro...

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Photo of Listing #12287391

838 Cherry Street, Winnetka, IL - $1,399,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,510 SQFT
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Captivating English Country Garden Home In Ideal "walk-to" Location To Metra, Library, Village Shopping & Dining, Schools, Parks, Playground & Beach. Ivy Covered Side Entrance With 2 Car Attached Garage With Tool/garden Prep Alcove. Custom Built ...

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Photo of Listing #12283529

332 Elder Lane, Winnetka, IL - $2,739,900

Residential, Detached Single
  • 7 Beds
  • 6 Baths
  • 6,102 SQFT
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Gracious, Grand And Set Less Than A Half Of Block Off Lake Michigan, Prepare To Fall In Love With This Very Special, Solidly Built East Winnetka Generational Home. Only The 4th Owner, This Approx. 6,000 Square Ft. Of Finished Space Over 3 Floors L...

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Photo of Listing #12280012

705 Oak Street, Winnetka, IL - $1,999,999

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,377 SQFT
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Location, Location, Location! This Stunning Home Is Ideally Situated Near Downtown Winnetka And Just Minutes From The Beach. Enjoy The Convenience Of Being Close To Top-rated Restaurants, Boutique Shops, Transportation, And Expressways-all While L...

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Photo of Listing #12285092

312 Rosewood Avenue, Winnetka, IL - $1,495,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,560 SQFT
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Offers Due By 10:00 Am On Monday, 2/10. Welcome To 312 Rosewood Avenue, A Stunningly Beautiful 4-bedroom, 3.1 Bath Home On One Of Winnetka's Most Beloved Blocks. This Home Is Truly A Dream--with Spacious Rooms, Abundant Natural Light, And An Open ...

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32 Woodley Road, Winnetka, IL - $4,950,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 9,908 SQFT
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Nestled Down A Winding, Private Road On 1.9 Meticulous Park-like Acres, This Grand, Almost 10,000 Square Foot Residence Exudes Luxury And Timeless Elegance. The Front Entrance Is Set Apart From The Road By A Sweeping Circular Drive Bordered By Pri...

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865 Gordon Terrace, Winnetka, IL - $4,199,900

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 9,350 SQFT
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Discover The Pinnacle Of Custom Design With This Stunning Nantucket-inspired Adamczyk Home, Exuding Timeless Elegance With A Modern And Transitional Twist. Drawing Inspiration From The Grand Estates Of Maine, This 9,000+ Sq. Ft. Masterpiece Harmon...

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650 Briar Lane, Northfield, IL - $3,495,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
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This Home And It's Location Are Truly What Dreams Are Made Of. It Is Situated On 3 Stunning Acres At The Very End Of A Private Lane, Centered Between Both Top Ranked Schools In Northfield! In Addition To It's Gorgeous, Classic Exterior, And It's O...

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928 Pine Street, Winnetka, IL - $1,549,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,153 SQFT
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This Classic Nantucket Colonial Blends Timeless Charm With Modern Updates And An Effortless Flow For Everyday Living And Entertaining. The Welcoming Foyer Leads Into A Formal Living Room, Complete With A Fireplace And Charming Built-ins. This L...

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35 Indian Hill Road, Winnetka, IL - $4,950,000

Residential, Detached Single
  • 7 Beds
  • 9 Baths
  • 9,744 SQFT
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Reimagined Luxury - Immerse Yourself In The Exquisite Transformation Of An English Manor Estate Nestled On A Private Lane Within One Mile Of Winnetka's Town Center. 35 Indian Hill Has Over One & One Half Million Dollars In Improvements Both Interi...

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139 Sheridan Road, Winnetka, IL - $9,750,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,723 SQFT
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There Is No Better Newer Construction Option On The Lake Like This Stunning Turn Key Perfect Beach House By Morgante Wilson. The Last Of New Construction Which Allowed Building Into The Bluff As This Home Is Truly On The Water As It's Only A 1 Min...

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880 Willow Road, Winnetka, IL - $1,100,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 3,100 SQFT
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Rare Opportunity In Today's Market To Find An Almost-new, Move-in-ready Home Offering Comfort, Convenience And A Contemporary Vibe. This Spacious 5-bedroom, 3.5-bath Home Features A Bright, Open Layout With Natural Oak Floors And A Designer Kitche...

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Start discovering the diverse Winnetka homes for sale including significant center hall brick Colonials, English Tudors, lakefront stone manor homes, Victorians, and modern classics by Tony Grunsfeld.. Prominent architects who set the tone for this coveted community include David Adler, Howard van Doren Shaw, and George Maher,

North Shore home buyers will find Winnetka offers a relaxed and gracious lifestyle. There are three public beaches: Lloyd Beach and Centennial Beach (dog beach), Elder Beach, and Tower Beach, an extensive Park District Program, the A.C. Nielsen Tennis Center, Winnetka Public Golf Course, and the Winnetka Ice Arena., as well as a selection of historically significant private golf and country clubs  A walkable community, Winnetka homes are convenient to commuter trains and three picturesque Tudor-style shopping areas featuring cafes, coffee houses, and fine dining.

Hubbard Woods in the northeast section of Winnetka is known for its natural beauty and ravines. Located along Green Bay Road you will find some of the finest antique shops on the North Shore. 

Winnetka is served by two public school districts:

  1. Winnetka School District 36: This district operates three elementary schools and one middle school. The elementary schools in District 36 include Crow Island School, Greeley School, and Hubbard Woods School. The middle school is called The Skokie School.

  2. New Trier Township High School District 203: This district operates New Trier High School, which is a highly regarded public high school serving the communities of Winnetka, Glencoe, Kenilworth, Northfield, and parts of Wilmette and Glenview.

    Private schools in Winnetka:

    1. North Shore Country Day School: A coeducational independent school offering education from junior kindergarten through grade 12.
    2. Sacred Heart School: A Catholic school providing education from preschool through grade 8.
    3. Faith, Hope & Charity School: A Catholic school offering education from preschool through grade 8.
    4. The Hadley School for the Blind: A distance education school that provides educational programs for individuals who are blind or visually impaired.
    5. Winnetka Community Nursery School: A cooperative preschool serving children ages 2 to 5 years.
    6. Montessori School of Winnetka: A Montessori school offering education from toddler through kindergarten.

Winnetka Parks

Winnetka is home to a number of beautiful parks. These parks offer a variety of recreational opportunities, such as playing fields, walking trails, playgrounds, and more. Here are some of the parks you might find in or near Winnetka:

  1. Crow Island Woods Park: This park offers natural beauty with walking trails and a natural woodland area.

  2. Dwyer Park: A popular spot with a playground, seating areas, and open space.

  3. Elder Lane Park: This park is located near the beach and offers a beach house and picnic area.

  4. Hubbard Woods Park: This park features a playground, picnic area, and tennis courts.

  5. Maple Street Park: A family-friendly park with playing fields, a playground, and tennis courts.

  6. Tower Road Beach: Not a traditional park, but a great place for swimming and enjoying the lake.

  7. Village Green Park: Located in the heart of Winnetka, this park offers a gazebo and is a popular spot for community events.

  8. Skokie Playfield: This large park complex includes fields for various sports, tennis courts, a track, and even a golf course.

  9. Lloyd Park: A beautiful place to enjoy Lake Michigan with a beach, playground, and boating opportunities.

  10. West Elm Park: A smaller park with a playground and open space for relaxation.

These parks and others in the area provide plenty of opportunities for outdoor enjoyment, whether you're interested in sports, nature walks, or just spending time with friends and family. 

Winnetka Golf Courses

  1. Winnetka Golf Club: Located at 1300 Oak St, Winnetka, is a public golf course that offers 9 holes of golf. It's a popular spot for local golfers and provides a great opportunity for recreation and practice.

  2. Indian Hill  is a private golf and country club situated at 1 Indian Hill Rd, Winnetka. The club offers various amenities, including a golf course, tennis courts, swimming pools, and dining facilities.

  3. Skokie Country Club: While not directly located in Winnetka, Skokie Country Club is nearby in Glencoe, IL. It is another private club with a well-regarded golf course and other amenities.

 

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The North Shore Chicago listings on this page include Winnetka IL homes for sale. The property listings are updated as soon as they hit the market with new Winnetka homes for sale and rent. Start your home search and schedule showings online or, to learn more about Winnetka and Chicago's North Shore, call 312.961.6212

  

 

Winnetka href="https://en.wikipedia.org/wiki/Winnetka,_Illinois">Winnetka on Wikipedia
Winnetka
Chicago, IL 60093
description" >Located just 16 miles from downtown Chicago, Winnetka is an excellent community for families who want to enjoy the best of both worlds. Home to some of the finest North Shore luxury real estate designed by prominent architects including David Adler, Howard van Doren Shaw, and George Maher, the Winnetka homes for sale are architecturally diverse and significant. Center hall brick Colonials, English Tudors, lakefront stone manor homes, Victorians, and modern classics by Tony Grunsfeld, offer buyers an excellent selection of beautiful residences to suit their lifestyles. There are three public beaches: Lloyd Beach and Centennial Beach (dog beach), Elder Beach, and Tower Beach, an extensive Park District Program, the A.C. Nielsen Tennis Center, Winnetka Public Golf Course, and the Winnetka Ice Arena. There are three picturesque Tudor-style shopping areas featuring cafes, coffee houses, and fine dining Elementary school children attend Crow Island, Hubbard Woods or Greeley for K-4th, Skokie for 5th-6th, and Carleton Washburne for 7th-8th grades. There are also pockets of the community that feed into the Avoca School District. High school students attend New Trier High School in District 203. Freshmen go to the Northfield Campus, and Sophomores, Juniors and Seniors attend the Winnetka Campus. Hubbard Woods in he northeast section of Winnetka, known for its natural beauty and ravines, has some of the finest antique shops on the North Shore, located along Green Bay Road

 

 

 

Midwest Real Estate Data LLC Logo The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Sotheby's International Realty are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Listing information last updated on February 11th, 2025 at 5:53pm CST.