Winnetka, IL Homes

/55
$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
$2,200,000 Sold Apr 07, 2025

529 Elder Ln, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 4,381 Sq Ft
- Built 1997
Last Sold Summary
- $502/SF
- 5 Days On Market
Current Estimated Value $2,296,047

Last Listing Agent Jenifer McCartney Jameson Sotheby's International Realty

529 Elder Ln, Winnetka, IL 60093

/46
Est $2,030,877 Not Listed For Sale

1357 Sunview Ln, Winnetka, IL 60093
- 5 Beds
- 6 Baths
- 5,581 Sq Ft
- Built 1953
1357 Sunview Ln, Winnetka, IL 60093

Last Sold Summary
- 28% Above List Price
- $284/SF
- 101 Days On Market
Last Sold Price $1,585,000

Last Listing Agent Jena Radnay @ Properties

/53
$2,799,000 Pending
- 5 Beds
- 4.5 Baths
- 3,748 Sq Ft
334 Woodland Ave, Winnetka, IL 60093

Absolutely breathtaking "better-than-new" East Winnetka Classic on an oversized (75' wide) property in a desirable walk-to-all location beautifully balances elegance and ease. Exquisitely renovated with timeless details and high-end designer finishes, it offers a harmonious blend of refined design and modern comfort on 1/3-acre of beautifully landscaped grounds with an attached two-car garage.

Paige Dooley Compass

334 Woodland Ave, 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 $1,950,570

Last Listing Agent Scott Fishman Worth Clark Realty

384 Provident Ave, Winnetka, IL 60093

/44
Est $1,950,904 Not Listed For Sale

1432 Asbury Ave, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 4,176 Sq Ft
- Built 2003
1432 Asbury Ave, Winnetka, IL 60093

Last Sold Summary
- 5% Below List Price
- $491/SF
- 27 Days On Market
Last Sold Price $2,050,000

Last Listing Agent Bonnie Tripton @ Properties

/46
$1,499,000 Pending
- 5 Beds
- 4.5 Baths
- 3,338 Sq Ft
277 Hibbard Rd, Winnetka, IL 60093

This beautifully renovated Hemphill Cape Cod lives effortlessly with a coveted first-floor primary suite. Offering five bedrooms and four and a half baths, the layout includes two additional bedrooms on the main level for exceptional flexibility. A full gut renovation and two-story expansion completed in 2015 by Twenty 9, Inc. of Highland Park seamlessly blends classic architectural character

Lauren Marquardt @properties Christie's International Real Estate

277 Hibbard Rd, 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 $1,493,060

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

1166 Cherry St, Winnetka, IL 60093

/22
Est $1,590,784 Not Listed For Sale

707 Hill Rd, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 3,869 Sq Ft
- Built 1889
707 Hill Rd, Winnetka, IL 60093

Last Sold Summary
- 60% Above List Price
- $257/SF
- 7 Days On Market
Last Sold Price $995,000

Last Listing Agent Gloria Matlin Compass

/71
$3,200,000
- 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
/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 $5,606,233

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

125 Birch St, Winnetka, IL 60093

/31
Est $496,080 Not Listed For Sale

772 Green Bay Rd, Winnetka, IL 60093
- 3 Beds
- 1.5 Baths
- 1,242 Sq Ft
- Built 1962
772 Green Bay Rd, Winnetka, IL 60093

Last Sold Summary
- 7% Above List Price
- $374/SF
- 0 Days On Market
Last Sold Price $465,000

Last Listing Agent David Korkoian Redfin Corporation

/46
$2,699,900 Open Sun 12PM - 2PM
- 6 Beds
- 6 Baths
- 7,000 Sq Ft
62 Woodley Rd, Winnetka, IL 60093

Gracefully tucked away on 1.55 acres of lush manicured grounds, 62 Woodley Road is a true Southern-inspired masterpiece reimagined for today's living. From the moment you approach the iconic black lacquered screen door with its Chippendale detail, you're drawn into a world of classic sophistication. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet

Jena Radnay @properties Christie's International Real Estate

62 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 $2,033,392

Last Listing Agent Michael Kelly Compass

803 Pine St, Winnetka, IL 60093

/39
Est $1,282,776 Not Listed For Sale

1156 Cherry St, Winnetka, IL 60093
- 3 Beds
- 2.5 Baths
- 3,100 Sq Ft
- Built 1942
1156 Cherry St, Winnetka, IL 60093

Last Sold Summary
- 11% Above List Price
- $371/SF
- 4 Days On Market
Last Sold Price $1,151,000

Last Listing Agent Melissa Dondalski @ Properties

/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 $865,612

Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

640 Winnetka Mews Unit 105, Winnetka, IL 60093

/46
Est $1,636,569 Not Listed For Sale

88 Abbottsford Rd, Winnetka, IL 60093
- 5 Beds
- 4 Baths
- 3,853 Sq Ft
- Built 1969
88 Abbottsford Rd, Winnetka, IL 60093

Last Sold Summary
- 12% Above List Price
- $379/SF
- 2 Days On Market
Last Sold Price $1,460,000

Last Listing Agent Paige Dooley Compass

/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 $4,098,157

Last Listing Agent Matan Aharoni Engel & Voelkers Chicago North Shore

518 Elder Ln, Winnetka, IL 60093

/29
Est $1,804,159 Not Listed For Sale

1216 Scott Ave, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,751 Sq Ft
- Built 1983
1216 Scott Ave, Winnetka, IL 60093

Last Sold Summary
- 10% Above List Price
- $594/SF
- 4 Days On Market
Last Sold Price $1,635,000

Last Listing Agent Lauer Bâby @ Properties

/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 $2,162,907

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

386 Fairview Ave, Winnetka, IL 60093

/37
Est $1,391,211 Not Listed For Sale

845 Locust St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 3,200 Sq Ft
- Built 1914
845 Locust St, Winnetka, IL 60093

Last Sold Summary
- 9% Above List Price
- $398/SF
- 45 Days On Market
Last Sold Price $1,275,000

Last Listing Agent Julie Mangan @ Properties

/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 $1,874,704

Last Listing Agent Paige Dooley Compass

251 Scott Ave, Winnetka, IL 60093

/50
Est $1,820,796 Not Listed For Sale

780 Rosewood Ave, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 3,262 Sq Ft
- Built 1899
780 Rosewood Ave, Winnetka, IL 60093

Last Sold Summary
- 8% Above List Price
- $517/SF
- 12 Days On Market
Last Sold Price $1,685,000

Last Listing Agent Cha McDaniel @ Properties

/40
$2,460,000 Sold Nov 12, 2025

228 Old Green Bay Rd, Winnetka, IL 60093
- 5 Beds
- 6 Baths
- 7,788 Sq Ft
- Built 1998
Last Sold Summary
- 7% Above List Price
- $316/SF
- 8 Days On Market
Last Listing Agent Susan Maman @properties Christie's International Real Estate

228 Old Green Bay Rd, Winnetka, IL 60093

/68
Est $3,573,416 Not Listed For Sale

161 Apple Tree Rd, Winnetka, IL 60093
- 5 Beds
- 9 Baths
- 7,289 Sq Ft
- Built 1936
161 Apple Tree Rd, Winnetka, IL 60093

Last Sold Summary
- 5% Above List Price
- $466/SF
- 49 Days On Market
Last Sold Price $3,400,000

Last Listing Agent Jena Radnay @ Properties

/25
$55,500 Sold Mar 10, 2026

1300 W Branch Rd, Winnetka, IL 60093
- 3 Beds
- 2 Baths
- Built 1988
Last Sold Summary
- 15% Below List Price
- 54 Days On Market
Last Listing Agent Virgilio Arreguin-Solorio My Casa Realty Corp.

1300 W Branch Rd, Winnetka, IL 60093

/36
Est $1,735,144 Not Listed For Sale

404 Elder Ln, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,623 Sq Ft
- Built 1920
404 Elder Ln, Winnetka, IL 60093

Last Sold Summary
- 9% Above List Price
- $606/SF
- 2 Days On Market
Last Sold Price $1,590,000

Last Listing Agent Jena Radnay @ Properties

/16
$700,000 Sold Jun 24, 2025

518 Winnetka Ave Unit 203, Winnetka, IL 60093
- 2 Beds
- 2.5 Baths
- 2,000 Sq Ft
- Built 2004
Last Sold Summary
- 17% Above List Price
- $350/SF
- 4 Days On Market
Current Estimated Value $635,019

Last Listing Agent Diana Radosta Compass

518 Winnetka Ave Unit 203, Winnetka, IL 60093

/13
Est $230,606 Not Listed For Sale

1095 Merril St Unit D2, Winnetka, IL 60093
- 1 Bed
- 1 Bath
- 532 Sq Ft
- Built 1993
1095 Merril St Unit D2, Winnetka, IL 60093

Last Sold Summary
- 10% Above List Price
- $395/SF
- 13 Days On Market
Last Sold Price $210,000

Last Listing Agent Hilde Wheeler Carter Coldwell Banker Realty

/16
$987,000 Sold Feb 24, 2026

436 Maple St, Winnetka, IL 60093
- 4 Beds
- 1.5 Baths
- 3,100 Sq Ft
- Built 1923
Last Sold Summary
- 13% Above List Price
- $318/SF
- 5 Days On Market
Current Estimated Value $1,270,581

Last Listing Agent Mark Jak @properties Christie's International Real Estate

436 Maple St, Winnetka, IL 60093

/22
Est $1,026,676 Not Listed For Sale

1065 Vine St, Winnetka, IL 60093
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
- Built 1961
1065 Vine St, Winnetka, IL 60093

Last Sold Summary
- 26% Above List Price
- $340/SF
- 1 Day On Market
Last Sold Price $815,000

Last Listing Agent Paige Dooley Compass

/11
$265,000 Sold Apr 15, 2025

134 Green Bay Rd Unit 309, Winnetka, IL 60093
- 1 Bed
- 1 Bath
- 1,030 Sq Ft
- Built 1971
Last Sold Summary
- $257/SF
- 2 Days On Market
Current Estimated Value $275,567

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

134 Green Bay Rd Unit 309, Winnetka, IL 60093

/49
Est $1,394,759 Not Listed For Sale

434 Elder Ln, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 2,620 Sq Ft
- Built 1928
434 Elder Ln, Winnetka, IL 60093

Last Sold Summary
- 27% Above List Price
- $420/SF
- 51 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Joanne Hudson Compass

/23
$525,000 Sold Jun 17, 2025

444 Winnetka Ave, Winnetka, IL 60093
- 2 Beds
- 1.5 Baths
- 1,234 Sq Ft
- Built 1955
Last Sold Summary
- 17% Above List Price
- $425/SF
- 2 Days On Market
Current Estimated Value $451,887

Last Listing Agent Debbie Croft @properties Christie's International Real Estate

444 Winnetka Ave, Winnetka, IL 60093

/2
Est $2,237,728 Not Listed For Sale

315 Woodland Ave, Winnetka, IL 60093
- 5 Beds
- 4 Baths
- 5,510 Sq Ft
- Built 1925
315 Woodland Ave, Winnetka, IL 60093

Last Sold Summary
- 18% Above List Price
- $345/SF
- 3 Days On Market
Last Sold Price $1,900,000

Last Listing Agent Corinne Evans Compass

/36
$2,675,000 Sold Jun 17, 2025

474 Sheridan Rd, Winnetka, IL 60093
- 6 Beds
- 4.5 Baths
- 4,251 Sq Ft
- Built 1937
Last Sold Summary
- 3% Below List Price
- $629/SF
- 67 Days On Market
Current Estimated Value $2,827,801

Last Listing Agent Carrie Healy Compass

474 Sheridan Rd, Winnetka, IL 60093

/50
Est $1,547,813 Not Listed For Sale

480 Rosewood Ave, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
- Built 1923
480 Rosewood Ave, Winnetka, IL 60093

Last Sold Summary
- 11% Above List Price
- $467/SF
- 3 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Alyson Tesar @ Properties

/53
$2,650,000 Sold Oct 27, 2025

755 Lincoln Ave, Winnetka, IL 60093
- 5 Beds
- 4.5 Baths
- 5,904 Sq Ft
- Built 1906
Last Sold Summary
- 2% Above List Price
- $449/SF
- 6 Days On Market
Current Estimated Value $2,672,469

Last Listing Agent Paige Dooley Compass

755 Lincoln Ave, Winnetka, IL 60093

/38
Est $2,204,162 Not Listed For Sale

920 Pine St, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 4,399 Sq Ft
- Built 2001
920 Pine St, Winnetka, IL 60093

Last Sold Summary
- 1% Above List Price
- $494/SF
- 4 Days On Market
Last Sold Price $2,175,000

Last Listing Agent Bonnie Tripton @ Properties

/44
$2,495,000 Sold Jun 27, 2025

548 Cherry St, Winnetka, IL 60093
- 6 Beds
- 4.5 Baths
- 5,800 Sq Ft
- Built 1908
Last Sold Summary
- $430/SF
- 3 Days On Market
Current Estimated Value $2,567,891

Last Listing Agent Sally O'Donnell @properties Christie's International Real Estate

548 Cherry St, Winnetka, IL 60093

Showing Results 161 - 200, Page 5 of 18

Illinois Cook County Winnetka

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