Winnetka, IL Homes

/36
$950,000
- 4 Beds
- 1.5 Baths
- 2,100 Sq Ft
979 Vine St, Winnetka, IL 60093

Nestled just blocks from Winnetka's famed lakefront, this 4-bed/1.5-bath single-family home at 979 Vine St offers approximately 2,100 sq ft of living space, hardwood floors, a spacious kitchen, and thoughtful layout across levels. Located a few blocks to Tower Road Park/ beach - Lake Michigan and Lloyd Park Boat Launch.. Steps to Green Bay Train - for biking, running, and casual strolls. Plus

Vernon Spence Jason Mitchell Real Estate IL

979 Vine St, Winnetka, IL 60093
/15
$1,645 - $2,145 per month
- Studio - 1 Bed
- 1 Bath
- 450 Sq Ft
- Condo for Rent
914 Green Bay Rd, Winnetka, IL 60093

Modern Living in Winnetka — 918 Green BayDiscover your next home at 918 Green Bay, where classic charm meets contemporary comfort in the heart of Winnetka. Offering spacious studios starting at $1,645 and 1-bedroom apartments from $1,645, our community delivers exceptional value in a premier North Shore location.Choose from a variety of thoughtfully designed layouts — some feature

914 Green Bay Rd, Winnetka, IL 60093
/2
$950,000 Sold Jan 20, 2026

Unlisted Address
- 4 Beds
- 3 Baths
- 2,062 Sq Ft
- Built 1928
Last Sold Summary
- $461/SF
- 2 Days On Market
Current Estimated Value $1,003,332

Last Listing Agent Susan Duffey @properties Christie's International Real Estate

Unlisted Address

/37
Est $1,553,394 Not Listed For Sale

807 Cherry St, Winnetka, IL 60093
- 6 Beds
- 4.5 Baths
- 2,284 Sq Ft
- Built 1921
807 Cherry St, Winnetka, IL 60093

Last Sold Summary
- 11% Above List Price
- $613/SF
- 4 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Susan Maman @ Properties

/10
$50,000
- 3 Beds
- 2 Baths
431 4th St, Winnetka, IL 60093

This mobile home features 3 bedrooms and 2 bathrooms and is located within the desirable Glenview School District. The home offers an large kitchen with an additional eating area, in addition to the large dining room. A laundry room is right off the kitchen. The master bathroom includes a full bath. Two additional bedrooms round out this spaces 45X25 mobile home. The furnace and boiler are newer.

Michelle Galindo Baird & Warner

431 4th St, Winnetka, IL 60093
/2
$910,000 Sold Dec 17, 2025

158 Woodland Ave, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 2,200 Sq Ft
- Built 1920
Last Sold Summary
- 2% Above List Price
- $414/SF
Current Estimated Value $932,840

Last Listing Agent Catherine O'Connell @properties Christie's International Real Estate

158 Woodland Ave, Winnetka, IL 60093

/56
Est $1,831,172 Not Listed For Sale

550 Sheridan Rd, Winnetka, IL 60093
- 5 Beds
- 4.5 Baths
- 4,443 Sq Ft
- Built 1942
550 Sheridan Rd, Winnetka, IL 60093

Last Sold Summary
- 12% Above List Price
- $369/SF
- 58 Days On Market
Last Sold Price $1,640,000

Last Listing Agent Jena Radnay @ Properties

/3
$1,290,000
- Land
- 1.36 Acres
- $948,529 per Acre
2033 Winnetka Rd, Winnetka, IL 60093

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

Natalya Gorodetsky Core Realty & Investments, Inc

2033 Winnetka Rd, Winnetka, IL 60093
/44
$3,750,000 Sold Aug 01, 2025

180 De Windt Rd, Winnetka, IL 60093
- 5 Beds
- 3.5 Baths
- 5,735 Sq Ft
- Built 1930
Last Sold Summary
- 3% Above List Price
- $654/SF
- 2 Days On Market
Current Estimated Value $3,487,430

Last Listing Agent Grace Goro Compass

180 De Windt Rd, Winnetka, IL 60093

/30
Est $577,085 Not Listed For Sale

711 Oak St Unit 210, Winnetka, IL 60093
- 3 Beds
- 2 Baths
- 1,870 Sq Ft
- Built 1983
711 Oak St Unit 210, Winnetka, IL 60093

Last Sold Summary
- 23% Above List Price
- $251/SF
- 4 Days On Market
Last Sold Price $469,000

Last Listing Agent Chris Veech @ Properties

/35
$1,400,000
- 4 Beds
- 3 Baths
- 3,737 Sq Ft
303 Auburn Ave, Winnetka, IL 60093

Huge price drop to sell quickly. Come one, come all to this beautifully updated and refreshed colonial-style house tucked away on a quiet, tree-lined street. This home offers the rare combination of peaceful surroundings and an unbeatable location: walking distance to elementary and middle schools, and is in the New Trier High School district. Step into the welcoming entryway that flows easily to

Tim Chung Berkshire Hathaway HomeServices Chicago

303 Auburn Ave, Winnetka, IL 60093
/2
$4,700,000 Sold Aug 05, 2025

775 Sumac Ln, Winnetka, IL 60093
- 5 Beds
- 8.5 Baths
- 6,240 Sq Ft
- Built 2004
Last Sold Summary
- 2% Below List Price
- $753/SF
- 9 Days On Market
Current Estimated Value $4,763,530

Last Listing Agent Annie flanagan @properties Christie's International Real Estate

775 Sumac Ln, Winnetka, IL 60093

/38
Est $2,779,044 Not Listed For Sale

1024 Westmoor Rd, Winnetka, IL 60093
- 5 Beds
- 8 Baths
- 5,619 Sq Ft
- Built 2008
1024 Westmoor Rd, Winnetka, IL 60093

Last Sold Summary
- 15% Above List Price
- $432/SF
- 48 Days On Market
Last Sold Price $2,425,000

Last Listing Agent Rene Firmin @ Properties

/70
$2,995,000 Pending
- 5 Beds
- 7 Baths
- 5,900 Sq Ft
358 Winnetka Ave, Winnetka, IL 60093

Incredible Coveted Home with 5 bedrooms, 5.2 bathrooms, 3 garages on 1/3 acre property boasts Winnetka address and Kenilworth School District. Built in 2004, this beautiful brick home feels like new construction with a complete first floor renovation in 2019 and upgrades throughout the home. As you enter the sun filled foyer, you are greeted with an open floor plan and 9'.5" ceilings. Flanking

Kathryn Mangel @properties Christie's International Real Estate

358 Winnetka Ave, Winnetka, IL 60093
/46
$2,200,000 Sold Oct 15, 2025

1503 Edgewood Ln, Winnetka, IL 60093
- 4 Beds
- 5 Baths
- 3,319 Sq Ft
- Built 1927
Last Sold Summary
- 23% Above List Price
- $663/SF
- 3 Days On Market
Current Estimated Value $2,086,806

Last Listing Agent Sarah Lyons @properties Christie's International Real Estate

1503 Edgewood Ln, Winnetka, IL 60093

/48
Est $3,009,781 Not Listed For Sale

1016 Westmoor Rd, Winnetka, IL 60093
- 5 Beds
- 6.5 Baths
- 4,600 Sq Ft
- Built 2005
1016 Westmoor Rd, Winnetka, IL 60093

Last Sold Summary
- 4% Above List Price
- $630/SF
- 20 Days On Market
Last Sold Price $2,900,000

Last Listing Agent Jeannie Kurtzhalts Baird Warner

/28
$1,099,000 Pending
- 4 Beds
- 2.5 Baths
- 2,380 Sq Ft
1492 Asbury Ave, Winnetka, IL 60093

Rehabbers-Opportunity Awaits! Have you been searching for a home on one of Hubbard Woods' most cherished streets? A place where your family can grow, in a community known for its charm and friendly community? This is that rare opportunity. This solid 4 bed, 2.5 bath home is full of potential and perfectly situated in a sought-after neighborhood with top-rated schools. With thoughtful updates and

Maria Welch Perennial Properties

1492 Asbury Ave, Winnetka, IL 60093
/41
$1,950,000 Sold May 29, 2025

54 Indian Hill Rd, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 4,206 Sq Ft
- Built 1961
Last Sold Summary
- 15% Above List Price
- $464/SF
- 2 Days On Market
Current Estimated Value $1,781,224

Last Listing Agent Paige Dooley Compass

54 Indian Hill Rd, Winnetka, IL 60093

/50
Est $1,811,833 Not Listed For Sale

1509 Asbury Ave, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 3,123 Sq Ft
- Built 2003
1509 Asbury Ave, Winnetka, IL 60093

Last Sold Summary
- 1% Above List Price
- $575/SF
- 2 Days On Market
Last Sold Price $1,795,000

Last Listing Agent Nathan Freeborn Redfin Corporation

/58
$2,439,000
- 4 Beds
- 7 Baths
- 4,269 Sq Ft
1185 Hill Rd, Winnetka, IL 60093

Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast

Joanne Hudson Compass

1185 Hill Rd, Winnetka, IL 60093
/49
$2,350,000 Sold Jan 09, 2026

180 Apple Tree Rd, Winnetka, IL 60093
- 5 Beds
- 3.5 Baths
- 4,800 Sq Ft
- Built 1955
Last Sold Summary
- 6% Below List Price
- $490/SF
- 45 Days On Market
Current Estimated Value $2,419,373

Last Listing Agent Jena Radnay @properties Christie's International Real Estate

180 Apple Tree Rd, Winnetka, IL 60093

/42
Est $1,623,421 Not Listed For Sale

1041 Elm St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,354 Sq Ft
- Built 1923
1041 Elm St, Winnetka, IL 60093

Last Sold Summary
- 8% Above List Price
- $641/SF
- 2 Days On Market
Last Sold Price $1,510,000

Last Listing Agent Leslie Maguire @ Properties

/54
$1,699,000 Pending
- 5 Beds
- 3.5 Baths
- 3,142 Sq Ft
955 Vernon Ave, Winnetka, IL 60093

Nestled in the heart of one of Winnetka's most coveted neighborhoods, this handsome Tudor seamlessly blends timeless architecture with today's luxury finishes and amenities. Enter through the arched doorway to find beauty at every turn with new windows throughout the main rooms of the first floor. The spacious formal dining room conveniently opens directly to the beautiful kitchen. The timeless

Alyson Tesar @properties Christie's International Real Estate

955 Vernon Ave, Winnetka, IL 60093
/45
$2,300,000 Sold Mar 28, 2025

399 Ridge Ave, Winnetka, IL 60093
- 5 Beds
- 7 Baths
- 5,200 Sq Ft
Last Sold Summary
- $442/SF
- 125 Days On Market
Current Estimated Value $2,146,303

Last Listing Agent Rich Aronson Compass

399 Ridge Ave, Winnetka, IL 60093

/20
Est $587,388 Not Listed For Sale

711 Oak St Unit 401, Winnetka, IL 60093
- 2 Beds
- 2 Baths
- 1,544 Sq Ft
- Built 1983
711 Oak St Unit 401, Winnetka, IL 60093

Last Sold Summary
- 3% Above List Price
- $369/SF
- 0 Days On Market
Last Sold Price $570,000

Last Listing Agent Jason Zonis Crown Heights Realty

/44
$2,495,000 Open Sat 12PM - 2PM
- 5 Beds
- 4.5 Baths
- 5,065 Sq Ft
560 Elm St, Winnetka, IL 60093

Exceptional East Winnetka residence on a rare .4-acre lot, steps from the lake, beaches, schools, town, and train. Beautifully maintained and rich in character, this historically significant home blends timeless architectural detail with the comforts and scale suited for modern living. The home offers 5Bd/4.5Ba, with all bedrooms located on the second floor-an increasingly sought-after layout for

Julie Cassin @properties Christie's International Real Estate

560 Elm St, Winnetka, IL 60093
/33
$1,925,000 Sold Oct 23, 2025

355 Myrtle St, Winnetka, IL 60093
- 5 Beds
- 4.5 Baths
- 4,544 Sq Ft
- Built 1930
Last Sold Summary
- 12% Below List Price
- $424/SF
- 45 Days On Market
Current Estimated Value $2,033,483

Last Listing Agent Mary Grant @properties Christie's International Real Estate

355 Myrtle St, Winnetka, IL 60093

/54
Est $1,669,022 Not Listed For Sale

1168 Hamptondale Ave, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 2,949 Sq Ft
- Built 1916
1168 Hamptondale Ave, Winnetka, IL 60093

Last Sold Summary
- 21% Above List Price
- $470/SF
- 3 Days On Market
Last Sold Price $1,385,000

Last Listing Agent Stephanie Melgard @ Properties

/23
$1,400,000 Pending
- 4 Beds
- 3 Baths
- 2,898 Sq Ft
270 Euclid Ave, Winnetka, IL 60093

Tucked into a very private setting on a beautiful 1/3-acre lot in Winnetka, this mid-century modern ranch home offers timeless design and exceptional indoor-outdoor connection. Floor-to-ceiling windows fill the home with natural light and frame serene views throughout. A spacious great room and dining room combination creates an inviting, open layout ideal for everyday living and entertaining.

Brandy Simon Engel & Voelkers Chicago North Shore

270 Euclid Ave, Winnetka, IL 60093
/2
$1,502,000 Sold Apr 30, 2025

1050 Elm St, Winnetka, IL 60093
- 4 Beds
- 2.5 Baths
- 2,737 Sq Ft
Last Sold Summary
- 11% Above List Price
- $549/SF
- 3 Days On Market
Current Estimated Value $1,544,448

Last Listing Agent Howard Meyers Compass

1050 Elm St, Winnetka, IL 60093

/40
Est $2,998,805 Not Listed For Sale

566 Willow Rd, Winnetka, IL 60093
- 5 Beds
- 6.5 Baths
- 6,689 Sq Ft
- Built 2005
566 Willow Rd, Winnetka, IL 60093

Last Sold Summary
- 16% Above List Price
- $386/SF
- 1 Day On Market
Last Sold Price $2,585,000

Last Listing Agent Jena Radnay @ Properties

/25
$579,000 Pending
- 3 Beds
- 2 Baths
- 1,960 Sq Ft
711 Oak St Unit 106, Winnetka, IL 60093

Easy Living awaits in this wonderfully spacious, all one level condo in Five Star Location just steps to dining, shops, library, Metra and Winnetka beaches on Lake Michigan! Nearly 2000sq ft of living space includes 3 large bedrooms (or 2 beds plus den as currently being used) loads of closet space plus an in-unit laundry room. Nicely finished with most rooms having engineered Hardwood floors,

Kimberly Ann Hoegler @properties Christie's International Real Estate

711 Oak St Unit 106, Winnetka, IL 60093
/35
$1,477,000 Sold Aug 15, 2025

1218 Cherry St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 1,962 Sq Ft
- Built 1940
Last Sold Summary
- 21% Above List Price
- $753/SF
- 4 Days On Market
Current Estimated Value $1,457,821

Last Listing Agent Mary Egebrecht Jameson Sotheby's Intl Realty

1218 Cherry St, Winnetka, IL 60093

/24
Est $1,429,468 Not Listed For Sale

1173 Cherry St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,860 Sq Ft
- Built 1934
1173 Cherry St, Winnetka, IL 60093

Last Sold Summary
- 4% Above List Price
- $479/SF
- 6 Days On Market
Last Sold Price $1,370,000

Last Listing Agent Vanessa Carlson Illinois Discount Realty

/44
$2,500,000
- 5 Beds
- 4.5 Baths
- 5,184 Sq Ft
355 Linden St, Winnetka, IL 60093

Meticulously renovated, this exceptional Winnetka home blends timeless charm with modern luxury. The five-bedroom, four-and-a-half-bath home features thoughtfully curated details throughout. Ideally situated near the lake, train, schools, parks, and downtown. The interiors have been fully reimagined with high-end finishes throughout, including custom white oak herringbone flooring on the main

Iris Kohl Compass

355 Linden St, Winnetka, IL 60093
/22
$1,200,000 Sold May 28, 2025

812 Oak St Unit 200, Winnetka, IL 60093
- 3 Beds
- 2.5 Baths
- 2,300 Sq Ft
- Built 1997
Last Sold Summary
- 21% Above List Price
- $522/SF
- 5 Days On Market
Current Estimated Value $1,225,199

Last Listing Agent Cricket King @properties Christie's International Real Estate

812 Oak St Unit 200, Winnetka, IL 60093

/22
Est $918,724 Not Listed For Sale

130 Woodland Ave, Winnetka, IL 60093
- 3 Beds
- 2.5 Baths
- 1,668 Sq Ft
- Built 1921
130 Woodland Ave, Winnetka, IL 60093

Last Sold Summary
- 23% Above List Price
- $449/SF
- 5 Days On Market
Last Sold Price $749,000

Last Listing Agent Shelley Shelly @ Properties

/76
$2,450,000 Pending
- 6 Beds
- 5.5 Baths
- 5,687 Sq Ft
875 Gordon Terrace, Winnetka, IL 60093

Set on a beautifully landscaped .33 acre property in one of Winnetka's most convenient locations, 875 Gordon Terrace is a significant historic home thoughtfully reimagined through a recent comprehensive renovation and expansion. An elegant wrought iron fence with intricate scrollwork encloses the property, and the sweeping wraparound covered porch immediately sets the tone. Double doors with

Howard Meyers Compass

875 Gordon Terrace, Winnetka, IL 60093
/30
$1,207,000 Sold Jun 05, 2025

867 Lincoln Ave, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 2,297 Sq Ft
- Built 1924
Last Sold Summary
- 27% Above List Price
- $525/SF
- 4 Days On Market
Current Estimated Value $1,231,115

Last Listing Agent Cricket King @properties Christie's International Real Estate

867 Lincoln Ave, Winnetka, IL 60093

/59
Est $1,968,751 Not Listed For Sale

1224 Asbury Ave, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 3,868 Sq Ft
- Built 2000
1224 Asbury Ave, Winnetka, IL 60093

Last Sold Summary
- 13% Above List Price
- $452/SF
- 1 Day On Market
Last Sold Price $1,750,000

Last Listing Agent Joanne Hudson Compass

Showing Results 121 - 160, Page 4 of 18

Illinois Cook County Winnetka

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Winnetka, IL Homes

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