Winnetka, IL Homes

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  /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 $2,751,943

  Last Listing Agent Paige Dooley Compass

  755 Lincoln Ave, Winnetka, IL 60093
• 

  

  /2

  Est $610,797

  Not Listed For Sale

  711 Oak St Unit 408, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1980

  711 Oak St Unit 408, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Laurie Baker Lawlor @properties Christie's International Real Estate
• 

  

  

  /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
• 

  

  

  /27

  $1,225,000

  Sold Mar 31, 2026

  706 Foxdale Ave, Winnetka, IL 60093

  • 4 Beds
  • 2.5 Baths
  • 2,777 Sq Ft
  • Built 1994

  Last Sold Summary

  • $441/SF
  • 5 Days On Market

  Current Estimated Value $1,345,808

  Last Listing Agent Kate Huff @properties Christie's International Real Estate

  706 Foxdale Ave, Winnetka, IL 60093
• 

  

  

  /71

  Est $3,131,217

  Not Listed For Sale

  1234 Westmoor Rd, Winnetka, IL 60093

  • 4 Beds
  • 8 Baths
  • 4,753 Sq Ft
  • Built 2004

  1234 Westmoor Rd, Winnetka, IL 60093

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Joanne Hudson Compass
• 

  

  /49

  $2,795,000

  Pending

  • 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
• 

  

  /57

  $2,527,000

  Sold Apr 27, 2026

  410 Cedar St, Winnetka, IL 60093

  • 6 Beds
  • 5.5 Baths
  • 3,504 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Above List Price
  • $721/SF
  • 5 Days On Market

  Current Estimated Value $2,518,267

  Last Listing Agent Annika Valdiserri @properties Christie's International Real Estate

  410 Cedar St, Winnetka, IL 60093
• 

  

  /59

  Est $1,989,428

  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

  • 1 Day On Market

  Last Listing Agent Joanne Hudson Compass
• 

  

  /46

  $2,499,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 3,610 Sq Ft

  1192 Chatfield Rd, Winnetka, IL 60093

  This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and infrastructure improvements. Step

  Jena Radnay @properties Christie's International Real Estate

  1192 Chatfield Rd, Winnetka, IL 60093
• 

  

  /61

  $2,300,000

  Sold Jun 25, 2026

  870 Bryant Ave, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,762 Sq Ft
  • Built 1919

  Last Sold Summary

  • 10% Above List Price
  • $611/SF
  • 3 Days On Market

  Current Estimated Value $2,215,214

  Last Listing Agent Kathryn Moor Compass

  870 Bryant Ave, Winnetka, IL 60093
• 

  

  /44

  Est $2,153,543

  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

  • 27 Days On Market

  Last Listing Agent Bonnie Tripton @properties Christie's International Real Estate
• 

  

  /53

  $4,949,000

  • 6 Beds
  • 7 Baths
  • 13,000 Sq Ft

  320 Woodley Rd, Winnetka, IL 60093

  Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof,

  Susan Maman @properties Christie's International Real Estate

  320 Woodley Rd, Winnetka, IL 60093
• 

  

  /35

  $1,675,000

  Sold Oct 29, 2025

  1340 Westmoor Trail, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,807 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Above List Price
  • $440/SF
  • 4 Days On Market

  Current Estimated Value $1,764,000

  Last Listing Agent Bonnie Tripton @properties Christie's International Real Estate

  1340 Westmoor Trail, Winnetka, IL 60093
• 

  

  /22

  Est $1,532,510

  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

  • 7 Days On Market

  Last Listing Agent Gloria Matlin Compass
• 

  

  /47

  $1,720,000

  Sold Mar 30, 2026

  1351 Scott Ave, Winnetka, IL 60093

  • 4 Beds
  • 4 Baths
  • 3,686 Sq Ft
  • Built 1924

  Last Sold Summary

  • 1% Above List Price
  • $467/SF
  • 5 Days On Market

  Current Estimated Value $1,710,825

  Last Listing Agent Bonnie Tripton @properties Christie's International Real Estate

  1351 Scott Ave, Winnetka, IL 60093
• 

  

  /40

  Est $2,736,787

  Not Listed For Sale

  495 Willow Rd, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 6,000 Sq Ft
  • Built 1921

  495 Willow Rd, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Paige Dooley Compass
• 

  

  /48

  $3,600,000

  Sold Nov 14, 2025

  5 Woodley Rd, Winnetka, IL 60093

  • 8 Beds
  • 7 Baths
  • 7,168 Sq Ft
  • Built 1938

  Last Sold Summary

  • 10% Below List Price
  • $502/SF
  • 29 Days On Market

  Current Estimated Value $3,809,117

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

  5 Woodley Rd, Winnetka, IL 60093
• 

  

  /39

  Est $1,318,688

  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

  • 4 Days On Market

  Last Listing Agent Melissa Dondalski @properties Christie's International Real Estate
• 

  

  /36

  $3,050,000

  Sold Oct 01, 2025

  519 Cedar St, Winnetka, IL 60093

  • 6 Beds
  • 5.5 Baths
  • 4,295 Sq Ft
  • Built 1917

  Last Sold Summary

  • 13% Above List Price
  • $710/SF
  • 2 Days On Market

  Current Estimated Value $3,164,895

  Last Listing Agent Paige Dooley Compass

  519 Cedar St, Winnetka, IL 60093
• 

  

  /46

  Est $1,720,001

  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

  • 2 Days On Market

  Last Listing Agent Paige Dooley Compass
• 

  

  /11

  $81,500

  Sold Jan 20, 2026

  804 8th St, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • Built 2015

  Last Sold Summary

  • 26% Below List Price
  • 200 Days On Market

  Last Listing Agent Virgilio Arreguin-Solorio My Casa Realty Corp.

  804 8th St, Winnetka, IL 60093
• 

  

  /29

  Est $1,845,533

  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

  • 4 Days On Market

  Last Listing Agent Lauer Bâby @properties Christie's International Real Estate
• 

  

  /27

  $900,000

  Sold Jul 24, 2026

  376 Rosewood Ave, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • Built 1954

  Last Sold Summary

  • 9% Above List Price
  • $464/SF
  • 3 Days On Market

  Current Estimated Value $923,553

  Last Listing Agent Courtney Elko Jameson Sotheby's International Realty

  376 Rosewood Ave, Winnetka, IL 60093
• 

  

  /37

  Est $1,527,141

  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

  • 45 Days On Market

  Last Listing Agent Julie Mangan @properties Christie's International Real Estate
• 

  

  /39

  $1,797,000

  Sold Aug 12, 2025

  318 Sunset Rd, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,165 Sq Ft
  • Built 1933

  Last Sold Summary

  • 18% Above List Price
  • $568/SF

  Current Estimated Value $1,982,798

  Last Listing Agent Michael Maggio @properties Christie's International Real Estate

  318 Sunset Rd, Winnetka, IL 60093
• 

  

  /50

  Est $1,868,268

  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

  • 12 Days On Market

  Last Listing Agent Cha McDaniel @properties Christie's International Real Estate
• 

  

  /33

  $1,725,000

  Sold Apr 17, 2026

  312 Rosewood Ave, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,560 Sq Ft
  • Built 1954

  Last Sold Summary

  • 4% Below List Price
  • $485/SF
  • 18 Days On Market

  Current Estimated Value $1,725,211

  Last Listing Agent Nick Nastos Fulton Grace Realty

  312 Rosewood Ave, Winnetka, IL 60093
• 

  

  /68

  Est $3,916,875

  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

  • 49 Days On Market

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

  

  /43

  $1,807,000

  Sold Dec 15, 2025

  611 Ash St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  Last Sold Summary

  • 10% Above List Price
  • $524/SF
  • 3 Days On Market

  Current Estimated Value $1,950,245

  Last Listing Agent Annika Valdiserri @properties Christie's International Real Estate

  611 Ash St, Winnetka, IL 60093
• 

  

  /36

  Est $1,758,942

  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

  • 2 Days On Market

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

  

  /51

  $2,945,000

  Sold Nov 14, 2025

  1004 Oak St, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 5,500 Sq Ft
  • Built 2015

  Last Sold Summary

  • 18% Above List Price
  • $535/SF
  • 6 Days On Market

  Current Estimated Value $3,110,865

  Last Listing Agent Colleen Archer Daugherty @properties Christie's International Real Estate

  1004 Oak St, Winnetka, IL 60093
• 

  

  /13

  Est $216,644

  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

  • 13 Days On Market

  Last Listing Agent Hilde Wheeler Carter Coldwell Banker Realty
• 

  

  /64

  $2,765,000

  Sold Jun 12, 2026

  1241 Ash St, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 4,680 Sq Ft
  • Built 2010

  Last Sold Summary

  • 11% Above List Price
  • $591/SF
  • 3 Days On Market

  Current Estimated Value $2,552,736

  Last Listing Agent Joanne Hudson Compass

  1241 Ash St, Winnetka, IL 60093
• 

  

  /48

  Est $2,413,953

  Not Listed For Sale

  484 Hawthorn Ln, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 4,147 Sq Ft
  • Built 2009

  484 Hawthorn Ln, Winnetka, IL 60093

  Last Sold Summary

  Last Listing Agent Nathan Freeborn Redfin Corporation
• 

  

  /8

  $1,554,000

  Sold Dec 29, 2025

  Unlisted Address

  • 5 Beds
  • 4.5 Baths
  • 1,084 Sq Ft
  • Built 1919

  Last Sold Summary

  • 7% Above List Price
  • $1,434/SF

  Current Estimated Value $1,619,948

  Last Listing Agent Peter Cummins Baird & Warner

  Unlisted Address
• 

  

  /49

  Est $1,478,483

  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

  • 51 Days On Market

  Last Listing Agent Joanne Hudson Compass
• 

  

  /26

  $1,515,000

  Sold May 01, 2026

  174 Woodland Ave, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 3,248 Sq Ft
  • Built 1925

  Last Sold Summary

  • 8% Above List Price
  • $466/SF
  • 4 Days On Market

  Current Estimated Value $1,485,721

  Last Listing Agent Marlene Rubenstein Baird & Warner

  174 Woodland Ave, Winnetka, IL 60093
• 

  

  /91

  Est $4,720,924

  Not Listed For Sale

  89 Indian Hill Rd, Winnetka, IL 60093

  • 5 Beds
  • 8 Baths
  • 5,709 Sq Ft
  • Built 1975

  89 Indian Hill Rd, Winnetka, IL 60093

  Last Sold Summary

  Last Listing Agent Frank Capitanini Compass
• 

  

  /44

  $1,925,000

  Sold Feb 02, 2026

  1235 Scott Ave, Winnetka, IL 60093

  • 6 Beds
  • 7 Baths
  • 4,546 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $423/SF
  • 12 Days On Market

  Current Estimated Value $1,909,269

  Last Listing Agent Cynthia Poulakidas Tobin @properties Christie's International Real Estate

  1235 Scott Ave, Winnetka, IL 60093
• 

  /2

  Est $2,271,975

  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

  • 3 Days On Market

  Last Listing Agent Corinne Evans Compass

Showing Results 161 - 200, Page 5 of 18