Connect

Find us on...

Dashboard

Login using...

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

View All Winnetka Homes for Sale _ Updated Every 15 minutes

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
$5,000,000 - $10,000,000
Map Save this Search
Sort listings by:Price, Highest First
Photo of Listing #11101494

1134 Taylorsport Lane, Winnetka, IL - $7,500,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 7,433 SQFT
View details More Photos Save

Majestically Situated On Lake Michigan, This Spectacular Home Blends Luxury, Elegance, And A Sleek Design With The Wonders Of Nature, Creating An Environment That Rewards The Eye And Imagination From Every Angle. You Will See The Lake From Every R...

Midwest Real Estate Data LLC Logo

910 Private Road, Winnetka, IL - $6,300,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 9,600 SQFT
View details More Photos Save

Perfection Personified. Rarely Available Private Road Estate On Oversized Lot In Ideal Location That Is Walking Distance To The North Shore's Best Beaches And Downtown Winnetka. No Detail Has Been Spared In Creating This Sophisticated Home With Th...

Midwest Real Estate Data LLC Logo
Photo of Listing #11021083

1215 Whitebridge Hill Road, Winnetka, IL - $5,995,000

Residential, Detached Single
  • 6 Beds
  • 10 Baths
View details More Photos Save

Dramatic Nearly $255,000 Price Reduction And Designer Renovation To Kitchen And Lower Entertainment Level! This 6 Bed, 6.4 Bath Lakefront Home Has One Of The Largest Private Beaches On The North Shore And Boasts Lake Views From Nearly Every Room ...

Midwest Real Estate Data LLC Logo

140 Sheridan Road, Winnetka, IL - $5,450,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 12.4k SQFT
View details More Photos Save

Welcome To 140 Sheridan Road. A Rare Opportunity To Own An Architecturally And Historically Significant Mayo Estate Just Steps From Lake Michigan. Built In 1928 As The Felix Lowy House, This Majestic Home Is Situated On Just Over One Acre Of Lan...

Midwest Real Estate Data LLC Logo

745 Sheridan Road, Winnetka, IL - $4,890,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 7,568 SQFT
View details More Photos Save

This Magnificent French Chateau, Custom Private Real Estate Is Situated On East Of Sheridan Rd, Luxury Mentions Surrounded Winnetka's Glorious Lakefront. This 7 Bed/7.5 Bath Home Welcomes You With A Circle Drive And Meticulous Landscaping And Has ...

Midwest Real Estate Data LLC Logo

1015 Starr Road, Winnetka, IL - $4,799,900

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,473 SQFT
View details More Photos Save

Extraordinary In Every Way! This Spectacular New Construction Home Is Situated On One Of The Most Sought Out Winnetka Streets, In The Heart Of The Village, Walk To Town, Schools And Train. The Open Floor Plan Offers Great Family Lifestyle Opportu...

Midwest Real Estate Data LLC Logo
Photo of Listing #10980400

27 Indian Hill Road, Winnetka, IL - $4,799,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 8,800 SQFT
View details More Photos Save

Magnificent Georgian Home Secluded On Private Road With 1.6 Acres Overlooking Spring Fed Lake. This Classic Home Was Built In 2005 With Exquisite Millwork, Generously Scaled Rooms And Eleven Foot Ceilings On The First Floor And 9 Foot Ceilings O...

Midwest Real Estate Data LLC Logo

885 Private Road, Winnetka, IL - $4,499,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 10.5k SQFT
View details More Photos Save

Extraordinarily Rare New Construction On Over A Half Acre (.6) Of A Beautiful Wooded Lot On One Of Winnetka's Most Coveted Locations. Fantastic In-town Country Living On A Private Retreat Artfully Crafted By One Of The North Shores Premier Builder...

Midwest Real Estate Data LLC Logo
Photo of Listing #11128757

113 Woodley Road, Winnetka, IL - $4,299,900

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 8,076 SQFT
View details More Photos Save

It's All Here At This Expansive, Custom Winnetka Estate, Built By Charles Page, Beautifully Set On 1.5 Acres Of Manicured Grounds In The Best Nook Of Woodley Road. This Solid Stone Newer Construction W/ Over 8,000 Square Feet Of Living Space Is Pe...

Midwest Real Estate Data LLC Logo

738 Tower Road, Winnetka, IL - $3,999,999

Residential, Detached Single
  • 6 Beds
  • 11 Baths
  • 10k SQFT
View details More Photos Save

Outstanding Beautiful Lakefront Red Brick Georgian Nestled Between Tower & Lloyd Beaches In The Heart Of East Winnetka! Spectacular Lake Views From All 4 Floors Of Phenomenal Space. Watch The Sunrise & Set. Gated Entrance - A Stunning Grand Foyer ...

Midwest Real Estate Data LLC Logo

150 Meadow Lane, Winnetka, IL - $3,999,900

Residential, Detached Single
  • 5 Beds
  • 6 Baths
View details More Photos Save

Idyllic & Rare Winnetka Estate Set On Picturesque Grounds Of 1.5 Acres Right In The Heart Of Winnetka & In Crow Island District! A Special Renovated Gem That Offers Serenity And Privacy Unlike Any Thing Else This Close To Town. Organically Set At ...

Midwest Real Estate Data LLC Logo

731 Prospect Avenue, Winnetka, IL - $3,850,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
View details More Photos Save

One Of Winnetka's Most Extraordinary Retreats Reminiscent Of The Iconic Estates In Newport, Ri, This "better Than New" Meticulously And Lovingly Restored Historical Home Blends All Of Life's Comforts From The Oversized Porches To The Wonderful Ind...

Midwest Real Estate Data LLC Logo

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.

 Winnetka is coveted for its excellent schools including Winnetka Public School District.36. 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. Review the top private schools in Winnetka. 

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, located along Green Bay Road. 

Explore North Shore Homes by Community

  Browse Winnetka Homes to Rent

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 June 24th, 2021 at 3:30am CDT.