Winnetka, IL Homes

• 

  

  

  /75

  $3,750,000

  Sold Feb 24, 2026

  145 Woodley Rd, Winnetka, IL 60093

  • 5 Beds
  • 7 Baths
  • 7,548 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $497/SF
  • 0 Days On Market

  Current Estimated Value $3,754,157

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

  145 Woodley Rd, Winnetka, IL 60093
• 

  

  

  /23

  Est $1,515,163

  Not Listed For Sale

  542 Meadow Rd, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,384 Sq Ft
  • Built 1928

  542 Meadow Rd, Winnetka, IL 60093

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Kathryn Mangel @properties Christie's International Real Estate
• 

  

  

  /26

  $1,500,000

  Sold Jan 15, 2026

  305 Poplar St, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 3,128 Sq Ft
  • Built 1926

  Last Sold Summary

  • 20% Above List Price
  • $480/SF
  • 4 Days On Market

  Current Estimated Value $1,558,749

  Last Listing Agent Paige Dooley Compass

  305 Poplar St, Winnetka, IL 60093
• 

  

  

  /30

  Est $1,526,672

  Not Listed For Sale

  720 Pine St, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 2,192 Sq Ft
  • Built 1955

  720 Pine St, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jeffrey Lowe Compass
• 

  

  

  /35

  $2,610,000

  Sold Aug 15, 2025

  891 Spruce St, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Above List Price
  • $522/SF
  • 3 Days On Market

  Current Estimated Value $2,812,609

  Last Listing Agent Annie Cobb Challenger Baird & Warner

  891 Spruce St, Winnetka, IL 60093
• 

  

  /46

  Est $1,046,908

  Not Listed For Sale

  214 Poplar St, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 1,676 Sq Ft
  • Built 1921

  214 Poplar St, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Jeffrey Lowe Compass
• 

  /2

  $589,000

  Sold Apr 02, 2026

  711 Oak St Unit 106, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Above List Price
  • $301/SF
  • 4 Days On Market

  Current Estimated Value $585,505

  Last Listing Agent Kimberly Ann Hoegler @properties Christie's International Real Estate

  711 Oak St Unit 106, Winnetka, IL 60093
• 

  

  /40

  Est $2,189,125

  Not Listed For Sale

  824 Humboldt Ave, Winnetka, IL 60093

  • 3 Beds
  • 4.5 Baths
  • 4,800 Sq Ft
  • Built 2004

  824 Humboldt Ave, Winnetka, IL 60093

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Michael Canzolino Chicago Properties Firm
• 

  /2

  $2,437,000

  Sold May 22, 2026

  355 Linden St, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 5,184 Sq Ft
  • Built 1906

  Last Sold Summary

  • 3% Below List Price
  • $470/SF
  • 12 Days On Market

  Current Estimated Value $2,423,353

  Last Listing Agent Iris Kohl Compass

  355 Linden St, Winnetka, IL 60093
• 

  

  /29

  Est $1,794,432

  Not Listed For Sale

  1046 Dinsmore Rd, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 3,182 Sq Ft
  • Built 1923

  1046 Dinsmore Rd, Winnetka, IL 60093

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Margaret Murphy Burton @properties Christie's International Real Estate
• 

  

  /41

  $1,020,000

  Sold Nov 03, 2025

  674 Foxdale Ave, Winnetka, IL 60093

  • 4 Beds
  • 3 Baths
  • 1,704 Sq Ft
  • Built 1948

  Last Sold Summary

  • 3% Above List Price
  • $599/SF
  • 5 Days On Market

  Current Estimated Value $1,092,197

  Last Listing Agent Carol Munro Jameson Sotheby's International Realty

  674 Foxdale Ave, Winnetka, IL 60093
• 

  

  /38

  Est $1,288,613

  Not Listed For Sale

  345 Glendale Ave, Winnetka, IL 60093

  • 3 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • Built 1955

  345 Glendale Ave, Winnetka, IL 60093

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Jeffrey Lowe Compass
• 

  

  /76

  $2,750,000

  Sold May 01, 2026

  875 Gordon Terrace, Winnetka, IL 60093

  • 6 Beds
  • 5.5 Baths
  • 5,687 Sq Ft
  • Built 1878

  Last Sold Summary

  • 12% Above List Price
  • $484/SF
  • 5 Days On Market

  Current Estimated Value $2,761,078

  Last Listing Agent Howard Meyers Compass

  875 Gordon Terrace, Winnetka, IL 60093
• 

  

  /35

  Est $1,515,364

  Not Listed For Sale

  660 Walden Rd, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 1951

  660 Walden Rd, Winnetka, IL 60093

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Monica Sofranko @properties Christie's International Real Estate
• 

  

  /34

  $930,000

  Sold Dec 08, 2025

  228 Poplar St, Winnetka, IL 60093

  • 4 Beds
  • 3 Baths
  • 1,801 Sq Ft
  • Built 1919

  Last Sold Summary

  • 3% Above List Price
  • $516/SF
  • 3 Days On Market

  Current Estimated Value $1,034,323

  Last Listing Agent Debbie Mora Evans Coldwell Banker Realty

  228 Poplar St, Winnetka, IL 60093
• 

  

  /7

  Est $1,690,550

  Not Listed For Sale

  1040 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 4,065 Sq Ft
  • Built 1893

  1040 Spruce St, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Joanne Hudson Compass
• 

  

  /41

  $2,100,000

  Sold Dec 08, 2025

  520 Provident Ave, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • Built 2005

  Last Sold Summary

  • 8% Above List Price
  • $553/SF
  • 3 Days On Market

  Current Estimated Value $2,238,106

  Last Listing Agent Paige Dooley Compass

  520 Provident Ave, Winnetka, IL 60093
• 

  

  /54

  Est $1,717,285

  Not Listed For Sale

  1114 Merril St, Winnetka, IL 60093

  • 6 Beds
  • 4.5 Baths
  • 3,674 Sq Ft
  • Built 1909

  1114 Merril St, Winnetka, IL 60093

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Kiki Clark Jameson Sotheby's International Realty
• 

  /2

  $1,500,000

  Sold Jun 03, 2026

  1256 Asbury Ave, Winnetka, IL 60093

  • 5 Beds
  • 2.5 Baths
  • 2,602 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Above List Price
  • $576/SF
  • 0 Days On Market

  Current Estimated Value $1,510,791

  Last Listing Agent Kathryn Moor Compass

  1256 Asbury Ave, Winnetka, IL 60093
• 

  

  /34

  Est $1,363,999

  Not Listed For Sale

  1070 Cherry St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 1,870 Sq Ft
  • Built 1924

  1070 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 54 Days On Market

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

  

  /42

  $1,750,000

  Sold Jun 30, 2026

  211 Church Rd, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 5,409 Sq Ft
  • Built 1835

  Last Sold Summary

  • $324/SF
  • 2 Days On Market

  Current Estimated Value $1,667,000

  Last Listing Agent Paige Dooley Compass

  211 Church Rd, Winnetka, IL 60093
• 

  

  /51

  Est $1,495,609

  Not Listed For Sale

  686 Foxdale Ave, Winnetka, IL 60093

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • Built 1954

  686 Foxdale Ave, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Paige Dooley Compass
• 

  

  /53

  $3,005,000

  Sold Apr 23, 2026

  334 Woodland Ave, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 3,748 Sq Ft
  • Built 1992

  Last Sold Summary

  • 7% Above List Price
  • $802/SF
  • 4 Days On Market

  Current Estimated Value $2,988,668

  Last Listing Agent Paige Dooley Compass

  334 Woodland Ave, Winnetka, IL 60093
• 

  /2

  Est $2,750,040

  Not Listed For Sale

  1172 Hamptondale Ave, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 4,870 Sq Ft
  • Built 1920

  1172 Hamptondale Ave, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Howard Meyers Compass
• 

  

  /59

  $1,995,000

  Sold Jan 13, 2026

  335 Fairview Ave, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,288 Sq Ft
  • Built 1923

  Last Sold Summary

  • $607/SF
  • 2 Days On Market

  Current Estimated Value $1,924,892

  Last Listing Agent Joanne Hudson Compass

  335 Fairview Ave, Winnetka, IL 60093
• 

  

  /20

  Est $599,729

  Not Listed For Sale

  680 Green Bay Rd Unit 202, Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft
  • Built 1975

  680 Green Bay Rd Unit 202, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent John Nash Jameson Sotheby's International Realty
• 

  

  /4

  $4,200,000

  Sold Nov 21, 2025

  977 Sheridan Rd, Winnetka, IL 60093

  • 5 Beds
  • 7 Baths
  • 8,294 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Below List Price
  • $506/SF
  • 27 Days On Market

  Current Estimated Value $4,480,933

  Last Listing Agent Kim Kelley Baird & Warner

  977 Sheridan Rd, Winnetka, IL 60093
• 

  

  /38

  Est $1,013,635

  Not Listed For Sale

  936 Spruce St, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft
  • Built 1909

  936 Spruce St, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Charles Arnold Keller Williams ONEChicago
• 

  

  /63

  $3,367,000

  Sold Feb 09, 2026

  Unlisted Address

  • 5 Beds
  • 7 Baths
  • 6,982 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Above List Price
  • $482/SF

  Current Estimated Value $3,473,590

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

  Unlisted Address
• 

  

  /48

  Est $1,833,313

  Not Listed For Sale

  850 Bell Ln, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,279 Sq Ft
  • Built 1976

  850 Bell Ln, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market

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

  

  /45

  $2,175,000

  Sold Dec 02, 2025

  43 Indian Hill Rd, Winnetka, IL 60093

  • 4 Beds
  • 6 Baths
  • 5,873 Sq Ft
  • Built 1977

  Last Sold Summary

  • 5% Below List Price
  • $370/SF
  • 16 Days On Market

  Current Estimated Value $3,681,000

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

  43 Indian Hill Rd, Winnetka, IL 60093
• 

  

  /57

  Est $4,885,470

  Not Listed For Sale

  1045 Starr Rd, Winnetka, IL 60093

  • 6 Beds
  • 9 Baths
  • 8,800 Sq Ft
  • Built 2014

  1045 Starr Rd, Winnetka, IL 60093

  Last Sold Summary

  • 5 Days On Market

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

  

  /36

  $1,450,000

  Sold May 19, 2026

  642 Ash St, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 2,316 Sq Ft
  • Built 1916

  Last Sold Summary

  • $626/SF
  • 5 Days On Market

  Current Estimated Value $1,474,174

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

  642 Ash St, Winnetka, IL 60093
• 

  

  /10

  Est $1,875,581

  Not Listed For Sale

  827 Prospect Ave, Winnetka, IL 60093

  • 4 Beds
  • 2.5 Baths
  • 2,854 Sq Ft
  • Built 1904

  827 Prospect Ave, Winnetka, IL 60093

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Karin Zawaski @properties Christie's International Real Estate
• 

  

  /28

  $1,550,000

  Sold May 08, 2026

  764 Boal Pkwy, Winnetka, IL 60093

  • 3 Beds
  • 3.5 Baths
  • 3,146 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Below List Price
  • $493/SF
  • 217 Days On Market

  Current Estimated Value $1,551,769

  Last Listing Agent Gloria Matlin Compass

  764 Boal Pkwy, Winnetka, IL 60093
• 

  

  /44

  Est $3,193,458

  Not Listed For Sale

  1066 Mount Pleasant Rd, Winnetka, IL 60093

  • 6 Beds
  • 5.5 Baths
  • 3,792 Sq Ft
  • Built 1961

  1066 Mount Pleasant Rd, Winnetka, IL 60093

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Marlene Rubenstein Baird & Warner
• 

  

  /46

  $1,860,000

  Sold Apr 17, 2026

  277 Hibbard Rd, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 3,338 Sq Ft
  • Built 1965

  Last Sold Summary

  • 24% Above List Price
  • $557/SF
  • 2 Days On Market

  Current Estimated Value $1,826,302

  Last Listing Agent Lauren Marquardt @properties Christie's International Real Estate

  277 Hibbard Rd, Winnetka, IL 60093
• 

  

  /29

  Est $1,680,431

  Not Listed For Sale

  618 Ridge Rd, Winnetka, IL 60093

  • 4 Beds
  • 3 Baths
  • 2,397 Sq Ft
  • Built 1954

  618 Ridge Rd, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty
• 

  

  /22

  $3,250,000

  Sold May 11, 2026

  Unlisted Address

  • 6 Beds
  • 5.5 Baths
  • 5,300 Sq Ft
  • Built 1898

  Last Sold Summary

  • 9% Above List Price
  • $613/SF

  Current Estimated Value $3,405,083

  Last Listing Agent Paige Dooley Compass

  Unlisted Address
• 

  

  /64

  Est $4,015,689

  Not Listed For Sale

  23 Indian Hill Rd, Winnetka, IL 60093

  • 5 Beds
  • 7 Baths
  • 5,589 Sq Ft
  • Built 1996

  23 Indian Hill Rd, Winnetka, IL 60093

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Paige Dooley Compass

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