Winnetka, IL Homes

/23
Est $800,540

Not Listed For Sale

800 Green Bay Rd, Winnetka, IL 60093
- 3 Beds
- 2 Baths
- 1,612 Sq Ft
- Built 1921
800 Green Bay Rd, Winnetka, IL 60093

Last Sold Summary
- 12 Days On Market

/36
$2,695,000

Pending
- 4 Beds
- 5 Baths
- 4,574 Sq Ft
92 Indian Hill Rd, Winnetka, IL 60093

This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move

Kathryn Mangel @properties Christie's International Real Estate

92 Indian Hill Rd, 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 $2,072,897

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

355 Myrtle St, Winnetka, IL 60093

/50
Est $2,158,071

Not Listed For Sale

1162 Scott Ave, Winnetka, IL 60093
- 5 Beds
- 6 Baths
- 4,311 Sq Ft
- Built 1920
1162 Scott Ave, Winnetka, IL 60093

Last Sold Summary
- 16 Days On Market

/25
$1,700,000

Pending
- 4 Beds
- 3.5 Baths
- 3,364 Sq Ft
478 Sunset Rd, Winnetka, IL 60093

They don't build them like this anymore, but they should! This solidly built custom Hemphill home is ideally located in sought-after East Winnetka and offers timeless character, quality craftsmanship, and thoughtful updates. Built in 1936 with exceptional materials and lovingly maintained by only two owners, this home combines classic elegance with modern comfort. The spacious living room

Cha McDaniel @properties Christie's International Real Estate

478 Sunset Rd, 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 $1,495,345

Last Listing Agent Mary Egebrecht Jameson Sotheby's Intl Realty

1218 Cherry St, Winnetka, IL 60093

/36
Est $1,821,385

Not Listed For Sale

385 Provident Ave, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 3,178 Sq Ft
- Built 1996
385 Provident Ave, Winnetka, IL 60093

Last Sold Summary
- 3 Days On Market

/34
$2,195,000

Pending
- 6 Beds
- 6 Baths
- 4,142 Sq Ft
757 Locust St, Winnetka, IL 60093

Welcome to 757 Locust, a stunning 6-bedroom, 4.2-bath home set on a 15,000-square-foot lot in the heart of Hubbard Woods. Built in 1920 and thoughtfully updated over the years, this exceptional residence blends timeless architecture with modern comfort, exuding character, warmth, and charm at every turn. Large, gracious rooms, soaring ceilings, and oversized windows create a sense of light and

Lisa Weis @properties Christie's International Real Estate

757 Locust St, Winnetka, IL 60093
/23
$639,000

Sold Mar 27, 2026

640 Winnetka Mews Unit 405, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 1,862 Sq Ft
- Built 1971
Last Sold Summary
- $343/SF
- 5 Days On Market
Current Estimated Value $648,337

Last Listing Agent Joanne Hudson Compass

640 Winnetka Mews Unit 405, Winnetka, IL 60093

/37
Est $1,481,309

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
- 4 Days On Market

/38
$1,699,000

Pending
- 4 Beds
- 4.5 Baths
- 3,639 Sq Ft
995 Oak St, Winnetka, IL 60093

Easy, in-town living in this wonderful home! This spacious home is conveniently located in the ideal 'walk to everything' location in the heart of Winnetka - close to absolutely everything. Built in 1995 with all the amenities one needs: classic center entry layout, large welcoming foyer, bright interior with an abundance of natural light, large scaled rooms, eat-in kitchen adjacent to family

Joanne Hudson Compass

995 Oak St, Winnetka, IL 60093
/10
$500,000

Sold May 01, 2026

97 High St, Winnetka, IL 60093
- 2 Beds
- 3.5 Baths
- 1,364 Sq Ft
- Built 1949
Last Sold Summary
- 17% Below List Price
- $367/SF
- 16 Days On Market
Current Estimated Value $583,970

Last Listing Agent Lilia Balan Pavlova Properties

97 High St, Winnetka, IL 60093

/56
Est $1,829,896

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
- 58 Days On Market

/81
$29,900,000
- 8 Beds
- 13 Baths
- 20,000 Sq Ft
319 Sheridan Rd, Winnetka, IL 60093

It's time to unveil the pinnacle of lakefront living in IL, as this newer construction estate is better than brand new construction as it encompasses features that could never be built today with the new lakefront building ordinances. Try to top this...your personal wellness club that is only 20 steps out to your own private, 141-foot wide, sandy beach with indoor pool, sauna, and

Jena Radnay @properties Christie's International Real Estate

319 Sheridan Rd, Winnetka, IL 60093
/39
$1,860,000

Sold Jul 25, 2025

384 Provident Ave, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 3,500 Sq Ft
- Built 2004
Last Sold Summary
- 5% Below List Price
- $531/SF
- 32 Days On Market
Current Estimated Value $2,009,134

Last Listing Agent Scott Fishman Worth Clark Realty

384 Provident Ave, Winnetka, IL 60093

/30
Est $559,374

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
- 4 Days On Market

/60
$1,495,000

Open Sat 11AM - 2PM
- 4 Beds
- 2.5 Baths
- 3,362 Sq Ft
1110 Elm St, Winnetka, IL 60093

Timeless Elegance Meets Modern Luxury with this prime Winnetka home on a large corner lot. Discover the perfect blend of historic character and contemporary living in this meticulously maintained, sun-drenched residence. From the moment you step inside, rich vintage craftsmanship takes center stage, highlighted by striking coffered ceilings, multiple cozy fireplaces, and an exquisite built-in

Brian Grienenberger Baird & Warner

1110 Elm St, Winnetka, IL 60093
/44
$1,400,000

Sold Jul 21, 2025

1166 Cherry St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 3,611 Sq Ft
- Built 1939
Last Sold Summary
- 4% Above List Price
- $388/SF
- 2 Days On Market
Current Estimated Value $1,564,158

Last Listing Agent Chris Veech @properties Christie's International Real Estate

1166 Cherry St, Winnetka, IL 60093

/38
Est $2,819,180

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
- 48 Days On Market

/56
$4,950,000
- 5 Beds
- 7 Baths
- 9,908 Sq Ft
32 Woodley Rd, Winnetka, IL 60093

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 private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal

Katharine Hackett @properties Christie's International Real Estate

32 Woodley Rd, Winnetka, IL 60093
/2
$5,500,000

Sold Jul 02, 2025

125 Birch St, Winnetka, IL 60093
- 5 Beds
- 9 Baths
- 7,451 Sq Ft
- Built 2012
Last Sold Summary
- $738/SF
Current Estimated Value $5,851,994

Last Listing Agent Carrie Tarzon @properties Christie's International Real Estate

125 Birch St, Winnetka, IL 60093

/48
Est $2,983,582

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
- 20 Days On Market

/42
$1,750,000

Pending
- 4 Beds
- 3.5 Baths
- 5,409 Sq Ft
211 Church Rd, Winnetka, IL 60093

A rare opportunity: A bright and beautiful, historic home spanning 3 lots near Indian Hill Train and several parks and schools! The 1/2 acre yard (149' wide) surrounding the home creates a setting that feels truly expansive. This 1835 farmhouse was reinvigorated with a significant 2004 renovation and addition including a kitchen and newer basement, new windows, roof, exterior siding around the

Paige Dooley Compass

211 Church Rd, Winnetka, IL 60093
/35
$1,615,000

Sold May 29, 2026

841 Prospect Ave, Winnetka, IL 60093
- 5 Beds
- 3.5 Baths
- 2,478 Sq Ft
- Built 1899
Last Sold Summary
- 11% Above List Price
- $652/SF
- 5 Days On Market
Current Estimated Value $1,467,222

Last Listing Agent Christie Ascione @properties Christie's International Real Estate

841 Prospect Ave, Winnetka, IL 60093

/50
Est $1,853,896

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
- 2 Days On Market

/72
$2,250,000
- 4 Beds
- 6 Baths
- 4,225 Sq Ft
42 Woodley Rd, Winnetka, IL 60093

Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

Peggy Lewis @properties Christie's International Real Estate

42 Woodley Rd, Winnetka, IL 60093
/50
$2,050,000

Sold Aug 28, 2025

803 Pine St, Winnetka, IL 60093
- 4 Beds
- 4 Baths
- 4,460 Sq Ft
- Built 2022
Last Sold Summary
- 16% Below List Price
- $460/SF
- 320 Days On Market
Current Estimated Value $2,113,017

Last Listing Agent Michael Kelly Compass

803 Pine St, Winnetka, IL 60093

/42
Est $1,597,754

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
- 2 Days On Market

/24
$975,000

Pending Pre-Foreclosure
- 4 Beds
- 3.5 Baths
- 2,427 Sq Ft
882 Willow Rd, Winnetka, IL 60093

Prepare to be captivated by this picture-perfect 4-bedroom, 3.1-bathroom colonial-cottage home, meticulously updated with high-end designer finishes throughout. Boasting incredible curb appeal with its deep blue siding, crisp white trim, and brick-paver paths, this turn-key residence seamlessly blends historic architectural character with contemporary luxury. Inside, an airy, light-filled layout

Karen Arenson Engel & Voelkers Chicago North Shore

882 Willow Rd, Winnetka, IL 60093
/28
$875,000

Sold Aug 25, 2025

640 Winnetka Mews Unit 105, Winnetka, IL 60093
- 2 Beds
- 2 Baths
- Built 1971
Last Sold Summary
- 3% Above List Price
- 5 Days On Market
Current Estimated Value $881,327

Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

640 Winnetka Mews Unit 105, Winnetka, IL 60093

/51
Est $2,525,612

Not Listed For Sale

390 Hawthorn Ln, Winnetka, IL 60093
- 4 Beds
- 5.5 Baths
- 5,300 Sq Ft
- Built 2006
390 Hawthorn Ln, Winnetka, IL 60093

Last Sold Summary
- 1 Day On Market

/49
$2,795,000
- 6 Beds
- 4.5 Baths
- 6,900 Sq Ft
127 Glenwood Ave, Winnetka, IL 60093

Nestled in one of the most sought-after and convenient locations in Winnetka/Hubbard Woods, this exceptional stone residence blends timeless architecture, refined design, and modern comfort just moments from town, the train, and Lake Michigan. Expertly crafted in 2006 by Adamczyk Fine Homes and Interiors, the home showcases nearly 7,000 square feet of beautifully designed living space across

Marina Carney Compass

127 Glenwood Ave, Winnetka, IL 60093
/29
$4,200,000

Sold Dec 17, 2025

518 Elder Ln, Winnetka, IL 60093
- 6 Beds
- 7 Baths
- 7,500 Sq Ft
- Built 2025
Last Sold Summary
- 5% Below List Price
- $560/SF
- 15 Days On Market
Current Estimated Value $3,963,137

Last Listing Agent Matan Aharoni Engel & Voelkers Chicago North Shore

518 Elder Ln, Winnetka, IL 60093

/20
Est $604,273

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
- 0 Days On Market

/71
$3,200,000

Pending
- 6 Beds
- 6 Baths
- 7,914 Sq Ft
100 Old Green Bay Rd, Winnetka, IL 60093

Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside the

Joanne Hudson Compass

100 Old Green Bay Rd, Winnetka, IL 60093
/39
$2,030,000

Sold Nov 24, 2025

386 Fairview Ave, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 5,284 Sq Ft
- Built 1921
Last Sold Summary
- 12% Below List Price
- $384/SF
- 10 Days On Market
Current Estimated Value $2,017,382

Last Listing Agent Alexa Hara @properties Christie's International Real Estate

386 Fairview Ave, Winnetka, IL 60093

/54
Est $1,632,433

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
- 3 Days On Market

/48
$2,245,000

$50K PRICE DROP Pending
- 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
/41
$1,856,000

Sold Jun 30, 2025

251 Scott Ave, Winnetka, IL 60093
- 5 Beds
- 3.5 Baths
- 3,468 Sq Ft
- Built 1923
Last Sold Summary
- 16% Above List Price
- $535/SF
- 2 Days On Market
Current Estimated Value $1,926,405

Last Listing Agent Paige Dooley Compass

251 Scott Ave, Winnetka, IL 60093

/24
Est $1,437,540

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
- 6 Days On Market

Showing Results 121 - 160, Page 4 of 18

Illinois Cook County Winnetka

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Winnetka, IL Homes

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