Winnetka, IL Homes

/45
$2,399,000
- 6 Beds
- 7 Baths
- 5,350 Sq Ft
1423 Asbury Ave, Winnetka, IL 60093

Better than NEW! This artfully restored & renovated home has the incredible combination of a classic center entry colonial home with sophisticated formal rooms and all the current amenities for today's modern lifestyle. This four-level home features abundant natural light, oversized windows, wide room openings and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end

Laura McCain Compass

1423 Asbury Ave, Winnetka, IL 60093
/70
$1,995 - $2,395 per month
- 1 - 2 Beds
- 1 Bath
- 900 Sq Ft
- Condo for Rent
545 Chestnut St, Winnetka, IL 60093

Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry

545 Chestnut St, Winnetka, IL 60093
/2
$2,600,000 Sold Apr 09, 2025

1172 Hamptondale Ave, Winnetka, IL 60093
- 5 Beds
- 6 Baths
- 4,870 Sq Ft
- Built 1920
Last Sold Summary
- 8% Above List Price
- $534/SF
- 4 Days On Market
Current Estimated Value $2,750,925

Last Listing Agent Howard Meyers Compass

1172 Hamptondale Ave, Winnetka, IL 60093

/23
Est $924,113 Not Listed For Sale

660 Winnetka Mews Unit 214, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 1,955 Sq Ft
- Built 1973
660 Winnetka Mews Unit 214, Winnetka, IL 60093

Last Sold Summary
- 3% Below List Price
- $486/SF
- 1 Day On Market
Last Sold Price $950,000

Last Listing Agent Paige Dooley Compass

/48
$2,295,000 Open Sun 2PM - 3:30PM
- 5 Beds
- 4.5 Baths
- 4,390 Sq Ft
1159 Chatfield Rd, Winnetka, IL 60093

Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and

Jason Rowland Compass

1159 Chatfield Rd, Winnetka, IL 60093
/29
$9,500 per month
- 4 Beds
- 3.5 Baths
- 3,076 Sq Ft
- House for Rent
526 Orchard Ln, Winnetka, IL 60093

Discover an incredible rental opportunity in the highly sought-after East Winnetka! This beautiful home features 4 bedrooms, 3.5 bathrooms, and generous living spaces on a wide 65-foot lot. The interior showcases hardwood floors, a cozy fireplace, and a modern updated kitchen with stainless steel appliances and stunning Calcutta white marble countertops. The kitchen seamlessly connects to a

Marlene Rubenstein Baird & Warner

526 Orchard Ln, Winnetka, IL 60093
/56
$2,450,000 Sold Oct 06, 2025

107 Woodley Rd, Winnetka, IL 60093
- 5 Beds
- 4.5 Baths
- 5,001 Sq Ft
- Built 1956
Last Sold Summary
- 14% Above List Price
- $490/SF
- 8 Days On Market
Current Estimated Value $2,462,210

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

107 Woodley Rd, Winnetka, IL 60093

/2
Est $1,683,984 Not Listed For Sale

1133 Scott Ave, Winnetka, IL 60093
- 5 Beds
- 4.5 Baths
- 5,300 Sq Ft
- Built 1923
1133 Scott Ave, Winnetka, IL 60093

Last Sold Summary
- 2% Below List Price
- $325/SF
- 4 Days On Market
Last Sold Price $1,725,000

Last Listing Agent Sherry Molitor Compass

/43
$2,199,000 Pending
- 5 Beds
- 5.5 Baths
- 4,994 Sq Ft
165 Fuller Ln, Winnetka, IL 60093

Welcome to 165 Fuller Ln, where timeless charm meets thoughtful, high-end finishes in an unbeatable East Winnetka location within the coveted Greeley School district. Perfectly positioned for walkability to school, the lake, parks, and everything downtown Winnetka has to offer, this five-bedroom, five-and-a-half-bath home delivers both convenience and refined living. Extensively renovated

Alexa Hara @properties Christie's International Real Estate

165 Fuller Ln, Winnetka, IL 60093
/7
$1,995 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
547 Chestnut St, Winnetka, IL 60093

547 Chestnut St, Winnetka, IL 60093
/2
$3,100,000 Sold Feb 17, 2026

Unlisted Address
- 6 Beds
- 7 Baths
- 5,338 Sq Ft
- Built 1915
Last Sold Summary
- 3% Below List Price
- $581/SF
- 16 Days On Market
Current Estimated Value $3,050,452

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

Unlisted Address

/38
Est $3,745,938 Not Listed For Sale

745 Sheridan Rd, Winnetka, IL 60093
- 6 Beds
- 7.5 Baths
- 9,930 Sq Ft
- Built 1990
745 Sheridan Rd, Winnetka, IL 60093

Last Sold Summary
- 50% Above List Price
- $252/SF
- 251 Days On Market
Last Sold Price $2,500,000

Last Listing Agent Vaciliki Ress Berkshire Hathaway HomeServices Chicago

/21
$7,275,000
- 6 Beds
- 7.5 Baths
- 15,000 Sq Ft
43 Indian Hill Rd, Winnetka, IL 60093

New magnificent transitional home situated on 1 acre picturesque lot with approximately 15,000 square feet finished space. Exterior is constructed of stone and limestone with slate roof which represents timeless construction. The house features 6 bedrooms, 7.1 bath, 4 fireplaces, spectacular Neff kitchen with top-of-the-line appliances including Sub-Zero refrigerators/freezers, luxury Wolf range,

Milena Birov @properties Christie's International Real Estate

43 Indian Hill Rd, Winnetka, IL 60093
/2
$1,995 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
811 Elm St Unit A07C, Winnetka, IL 60093

Winnetka817 Elm , Unit 205Beds:1Baths:1Rent:Sq.Ft:700Available:No

811 Elm St Unit A07C, Winnetka, IL 60093
/7
$2,350,000 Sold Oct 24, 2025

466 Chestnut St, Winnetka, IL 60093
- 5 Beds
- 5.5 Baths
- 4,433 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $530/SF
Current Estimated Value $2,298,248

Last Listing Agent Robert Milkowski Berger & Co. Realtors Ltd

466 Chestnut St, Winnetka, IL 60093

/46
Est $2,070,751 Not Listed For Sale

17 Longmeadow Rd, Winnetka, IL 60093
- 7 Beds
- 7 Baths
- 6,000 Sq Ft
- Built 1966
17 Longmeadow Rd, Winnetka, IL 60093

Last Sold Summary
- 26% Above List Price
- $275/SF
- 31 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Daniel Mirea Berkshire Hathaway HomeServices Chicago

/2
$1,950,000 New Construction
- 5 Beds
- 6 Baths
- 4,200 Sq Ft
67 Brier St, Winnetka, IL 60093

New construction home with 5BR, 6Bath,2 car detached garage, will be ready by March 2026. This more than 4000 sqft house boasts thoughtfully designed living space, combining modern luxury with everyday functionality, front and back porches and second floor primary BR with balcony. Step inside to soaring ceilings, and open layout, and high-end finishes throughout. The gourmet kitchen is a chef's

Nehru Arunasalam @properties Christie's International Real Estate

67 Brier St, Winnetka, IL 60093
/47
$1,595 - $2,095 per month
- Studio - 1 Bed
- 1 Bath
- 500 Sq Ft
- Condo for Rent
910 Green Bay Rd, Winnetka, IL 60093

910 Green Bay Rd, Winnetka, IL 60093
/26
$1,190,000 Sold Jul 17, 2025

812 Rosewood Ave, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,646 Sq Ft
- Built 1917
Last Sold Summary
- 4% Below List Price
- $450/SF
- 96 Days On Market
Current Estimated Value $1,290,803

Last Listing Agent Jackie Mack Jameson Sotheby's International Realty

812 Rosewood Ave, Winnetka, IL 60093

/15
Est $220,025 Not Listed For Sale

561 Hill Terrace Unit 310, Winnetka, IL 60093
- 1 Bed
- 1 Bath
- 500 Sq Ft
- Built 1928
561 Hill Terrace Unit 310, Winnetka, IL 60093

Last Sold Summary
- 2% Above List Price
- $430/SF
- 67 Days On Market
Last Sold Price $215,000

Last Listing Agent Michael Mitchell @ Properties

/59
$1,995,000 Pending
- 4 Beds
- 5 Baths
- 3,633 Sq Ft
1215 Spruce St, Winnetka, IL 60093

A RARE find...Amazing home with an expansive *first floor Primary suite, set on a spectacular half-acre in a prime Winnetka location! This deceptively spacious home offers exceptional indoor-outdoor living and a versatile floor plan. The professionally landscaped backyard is a true showstopper, featuring mature trees, perennial gardens and a spacious bluestone patio...perfect for large-scale

Megan Mawicke Jameson Sotheby's International Realty

1215 Spruce St, Winnetka, IL 60093
/17
$1,895 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
811 Elm St Unit J03W, Winnetka, IL 60093

817 Elm Elm + ChestnutWinnetka$1895 per MonthAvailable: Now$500 OFF FIRST MONTH'S RENT!AVAILABLE NOW! Gorgeous one bedroom, one bathroom in heart of downtown Winnetka features brand new kitchen with espresso cabinets, granite countertops, stainless steel appliances, dishwasher, spacious living area, large bedroom, great closet space, new bathroom, hardwood floors

811 Elm St Unit J03W, Winnetka, IL 60093
/19
$1,117,000 Sold Mar 11, 2026

380 Green Bay Rd Unit 1B, Winnetka, IL 60093
- 2 Beds
- 2 Baths
- 1,950 Sq Ft
- Built 1997
Last Sold Summary
- 16% Above List Price
- $573/SF
- 1 Day On Market
Current Estimated Value $882,094

Last Listing Agent Julie Miller Compass

380 Green Bay Rd Unit 1B, Winnetka, IL 60093

/9
Est $1,360,728 Not Listed For Sale

338 Linden St, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 2,407 Sq Ft
- Built 1962
338 Linden St, Winnetka, IL 60093

Last Sold Summary
- 20% Above List Price
- $469/SF
- 0 Days On Market
Last Sold Price $1,130,000

Last Listing Agent Christina Fawcett @ Properties

/72
$1,695,000 Pending
- 4 Beds
- 3.5 Baths
- 3,662 Sq Ft
567 Hill Terrace, Winnetka, IL 60093

**MULTIPLE OFFERS RECEIVED** HIGHEST & BEST DUE MONDAY 3/9 BY 11AM** Timeless Winnetka Colonial on Private Hill Terrace. Set on coveted Hill Terrace, a charming private street just moments from the Indian Hill Metra station, this beautifully maintained Winnetka Colonial offers an exceptional combination of classic architecture, thoughtful updates, and an unmatched walk-to-everything location.

Lauren Schuh-Dayton Jameson Sotheby's Intl Realty

567 Hill Terrace, Winnetka, IL 60093
/47
$1,595 - $2,095 per month
- Studio - 1 Bed
- 1 Bath
- 500 Sq Ft
- Condo for Rent
910 Green Bay Rd, Winnetka, IL 60093

910 Green Bay Rd, Winnetka, IL 60093
/48
$2,050,000 Sold Apr 15, 2025

484 Hawthorn Ln, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 4,147 Sq Ft
- Built 2009
Last Sold Summary
- 8% Above List Price
- $494/SF
Current Estimated Value $2,190,380

Last Listing Agent Nathan Freeborn Redfin Corporation

484 Hawthorn Ln, Winnetka, IL 60093

/66
Est $3,177,045 Not Listed For Sale

270 Birch St, Winnetka, IL 60093
- 6 Beds
- 8.5 Baths
- 6,298 Sq Ft
- Built 1927
270 Birch St, Winnetka, IL 60093

Last Sold Summary
- 6% Above List Price
- $476/SF
- 2 Days On Market
Last Sold Price $2,999,000

Last Listing Agent Stacy Burgoon Compass

/41
$1,450,000 Pending
- 5 Beds
- 3.5 Baths
- 3,047 Sq Ft
1004 Elm St, Winnetka, IL 60093

A large 5br home with a 4 car garage, a corner lot, and an amazing location! This home welcomes you with great curb appeal, starting with the front porch overlooking Elm. The main level has a separate dining and living room, and a large family room with a gas fireplace and a door to a large 2 tier deck that overlooks the backyard. The home gets great sunlight due to being on a corner lot, as most

Stephanie Cutter Coldwell Banker Realty

1004 Elm 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
/19
$985,000 Sold Nov 20, 2025

785 Locust St, Winnetka, IL 60093
- 3 Beds
- 1.5 Baths
- 1,224 Sq Ft
- Built 1911
Last Sold Summary
- 12% Above List Price
- $805/SF
- 12 Days On Market
Current Estimated Value $1,008,334

Last Listing Agent Crawford Group @properties Christie's International Real Estate

785 Locust St, Winnetka, IL 60093

/22
Est $1,542,273 Not Listed For Sale

1028 Cherry St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,711 Sq Ft
- Built 1925
1028 Cherry St, Winnetka, IL 60093

Last Sold Summary
- 10% Above List Price
- $516/SF
- 0 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Katie Traines @ Properties

/43
$1,399,000 Pending
- 4 Beds
- 2.5 Baths
- 2,116 Sq Ft
916 Oak St, Winnetka, IL 60093

An inviting front porch welcomes you into this beautifully renovated home in the heart of Winnetka, just steps from parks, town, train, and K-8 schools. Thoughtfully updated by the current owners, the home offers ideal living spaces in all the right places. A gracious foyer opens to the sun-filled living and dining rooms, where newer windows and a wood-burning fireplace create a warm, welcoming

Joanne Hudson Compass

916 Oak St, Winnetka, IL 60093
/65
$1,750 - $2,195 per month
- 1 - 2 Beds
- 1 Bath
- 700 Sq Ft
- Condo for Rent
894 Green Bay Rd, Winnetka, IL 60093

Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets

894 Green Bay Rd, Winnetka, IL 60093
/45
$2,400,000 Sold May 29, 2025

Unlisted Address
- 4 Beds
- 5 Baths
- 5,073 Sq Ft
- Built 1938
Last Sold Summary
- 9% Above List Price
- $473/SF
- 3 Days On Market
Current Estimated Value $2,497,796

Last Listing Agent Laura Fitzpatrick @properties Christie's International Real Estate

Unlisted Address

/32
Est $1,963,773 Not Listed For Sale

804 Boal Pkwy, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 4,490 Sq Ft
- Built 1955
804 Boal Pkwy, Winnetka, IL 60093

Last Sold Summary
- 27% Above List Price
- $345/SF
- 16 Days On Market
Last Sold Price $1,550,000

Last Listing Agent Selma Nemeth @ Properties

/23
$639,000 Pending
- 3 Beds
- 3 Baths
- 1,862 Sq Ft
640 Winnetka Mews Unit 405, Winnetka, IL 60093

Welcome to this spacious and sun-filled top-floor residence at the Winnetka Mews, a thoughtfully designed and impeccably managed condominium community in the heart of Winnetka. This classically updated 3-bedroom, 3-bath home enjoys south, east, and west exposures and offers exceptional one-level living with generous room sizes and an effortless floor plan. The expansive living room, anchored by a

Joanne Hudson Compass

640 Winnetka Mews Unit 405, Winnetka, IL 60093
/19
$1,895 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
808 Green Bay Rd Unit J00P, Winnetka, IL 60093

918 Green BayGreen Bay + TowerWinnetka$1895 per MonthAvailable: 6/1/2026Superb one bedroom, one bathroom in Winnetka features newer kitchen with dishwasher, separate dining room, large living room with decorative fireplace, spacious bedroom with ceiling fan, great closet space, hardwood floors, newer bathroom, laundry room in building, and pets are welcome. Steps to

808 Green Bay Rd Unit J00P, Winnetka, IL 60093
/23
$950,000 Sold Jun 20, 2025

283 Ridge Ave, Winnetka, IL 60093
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
- Built 1926
Last Sold Summary
- $473/SF
- 3 Days On Market
Current Estimated Value $1,007,595

Last Listing Agent Marilee Moyer @properties Christie's International Real Estate

283 Ridge Ave, Winnetka, IL 60093

/31
Est $2,964,898 Not Listed For Sale

824 Boal Pkwy, Winnetka, IL 60093
- 5 Beds
- 7 Baths
- 6,300 Sq Ft
- Built 2019
824 Boal Pkwy, Winnetka, IL 60093

Last Sold Summary
- 16% Above List Price
- $405/SF
- 6 Days On Market
Last Sold Price $2,550,000

Last Listing Agent Paul Gorney eXp Realty

Showing Results 41 - 80, Page 2 of 18

Illinois Cook County Winnetka

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Winnetka, IL Homes

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