5,328

Winnetka, IL Homes

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    • /50

      Est $1,815,943 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

      • 1% Above List Price
      • $575/SF
      • 2 Days On Market
      • Last Sold Price $1,795,000
      • Oct 15, 2024

      Last Listing Agent Nathan Freeborn Redfin Corporation

  • /48

    $4,699,000

    • 6 Beds
    • 9 Baths
    • 6,000 Sq Ft

    231 Woodlawn Ave, Winnetka, IL 60093

    Magnificent East Glencoe home- approximately 9,000 sf of total finished space. 6 BR all ensuite plus 3 additional half baths. Stone & brick exterior on over .5 acre lot. Close to train. Featuring a spectacular kitchen, media room, cherry library, workout room, sauna, wine cellar, and fully fenced expansive private outdoor living space with fireplace / TV and separate fire pit with seating area

    Craig Stone Stone Realty Group

    231 Woodlawn Ave, Winnetka, IL 60093
  • /49

    $2,350,000 Sold Jan 09, 2026

    180 Apple Tree Rd, Winnetka, IL 60093

    • 5 Beds
    • 3.5 Baths
    • 4,800 Sq Ft
    • Built 1955

    Last Sold Summary

    • 6% Below List Price
    • $490/SF
    • 45 Days On Market

    Current Estimated Value $2,431,939

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

    180 Apple Tree Rd, Winnetka, IL 60093
    • /42

      Est $1,584,668 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

      • 5% Above List Price
      • $641/SF
      • 2 Days On Market
      • Last Sold Price $1,510,000
      • Aug 24, 2023

      Last Listing Agent Leslie Maguire @ Properties

  • /36

    $2,695,000

    • 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 $1,993,354

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

    355 Myrtle St, Winnetka, IL 60093
    • /20

      Est $596,576 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

      • 5% Above List Price
      • $369/SF
      • 0 Days On Market
      • Last Sold Price $570,000
      • Nov 15, 2023

      Last Listing Agent Jason Zonis Crown Heights Realty

  • /43

    $1,869,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 4,023 Sq Ft

    556 Willow Rd, Winnetka, IL 60093

    Enjoy easy North Shore living in this beautifully maintained East Winnetka home, where you'll catch glimpses of Lake Michigan right from your driveway. Built in 2005, this newer construction home offers a rare combination of quality craftsmanship, thoughtful updates, and a layout that truly works for everyday living. The updated kitchen is the heart of the home, featuring new quartz countertops,

    Kathryn Moor Compass

    556 Willow 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 $1,458,300

    Last Listing Agent Mary Egebrecht Jameson Sotheby's Intl Realty

    1218 Cherry St, Winnetka, IL 60093
    • /54

      Est $1,655,976 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

      • 20% Above List Price
      • $470/SF
      • 3 Days On Market
      • Last Sold Price $1,385,000
      • Aug 09, 2024

      Last Listing Agent Stephanie Melgard @ Properties

  • /24

    $899,000 Pending

    • 3 Beds
    • 2.5 Baths

    574 Orchard Ln, Winnetka, IL 60093

    Perfectly situated in a prime East Winnetka location, this charming home offers an exceptional opportunity to enjoy one of the North Shore's most sought-after neighborhoods at an approachable price point. Just blocks from the lake, town, Metra, Greeley Elementary, and New Trier High School, the lifestyle and convenience are unmatched. Thoughtfully updated over time, the home features bright,

    Danielle Wylie Baird & Warner

    574 Orchard Ln, Winnetka, IL 60093
  • /22

    $1,200,000 Sold May 28, 2025

    812 Oak St Unit 200, Winnetka, IL 60093

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Built 1997

    Last Sold Summary

    • 21% Above List Price
    • $522/SF
    • 5 Days On Market

    Current Estimated Value $1,195,865

    Last Listing Agent Cricket King @properties Christie's International Real Estate

    812 Oak St Unit 200, Winnetka, IL 60093
    • /24

      Est $1,438,167 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

      • 5% Above List Price
      • $479/SF
      • 6 Days On Market
      • Last Sold Price $1,370,000
      • Nov 22, 2024

      Last Listing Agent Vanessa Carlson Illinois Discount Realty

  • /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
  • /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 $633,826

    Last Listing Agent Joanne Hudson Compass

    640 Winnetka Mews Unit 405, Winnetka, IL 60093
    • /22

      Est $921,580 Not Listed For Sale

      130 Woodland Ave, Winnetka, IL 60093

      • 3 Beds
      • 2.5 Baths
      • 1,668 Sq Ft
      • Built 1921
      130 Woodland Ave, Winnetka, IL 60093

      Last Sold Summary

      • 23% Above List Price
      • $449/SF
      • 5 Days On Market
      • Last Sold Price $749,000
      • Jun 06, 2023

      Last Listing Agent Shelley Shelly @ Properties

  • /50

    $2,995,000

    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    127 Glenwood Ave, Winnetka, IL 60093

    Solid stone construction, classic architecture, timeless design and refined living come together in perfect harmony in one of the most coveted and convenient locations in Winnetka/ Hubbard Woods with close proximity to town, train and Lake Michigan. Built in 2006 by Adamczyk Fine Homes and Interiors offering three levels of unparalleled craftmanship and quality totaling almost 7000 square feet.

    Marina Carney Compass

    127 Glenwood Ave, Winnetka, IL 60093
  • /30

    $1,207,000 Sold Jun 05, 2025

    867 Lincoln Ave, Winnetka, IL 60093

    • 3 Beds
    • 3 Baths
    • 2,297 Sq Ft
    • Built 1924

    Last Sold Summary

    • 27% Above List Price
    • $525/SF
    • 4 Days On Market

    Current Estimated Value $1,222,840

    Last Listing Agent Cricket King @properties Christie's International Real Estate

    867 Lincoln Ave, Winnetka, IL 60093
    • /71

      Est $3,082,683 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

      • 6% Above List Price
      • $614/SF
      • 16 Days On Market
      • Last Sold Price $2,920,000
      • Apr 30, 2025

      Last Listing Agent Joanne Hudson Compass

  • /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
  • /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 $596,322

    Last Listing Agent Lilia Balan Pavlova Properties

    97 High St, Winnetka, IL 60093
    • /59

      Est $1,917,616 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

      • 10% Above List Price
      • $452/SF
      • 1 Day On Market
      • Last Sold Price $1,750,000
      • Jun 20, 2024

      Last Listing Agent Joanne Hudson Compass

  • /42

    $1,750,000

    • 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
  • /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 $1,944,488

    Last Listing Agent Scott Fishman Worth Clark Realty

    384 Provident Ave, Winnetka, IL 60093
    • /44

      Est $1,978,790 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

      • 3% Below List Price
      • $491/SF
      • 27 Days On Market
      • Last Sold Price $2,050,000
      • Jan 17, 2025

      Last Listing Agent Bonnie Tripton @ Properties

  • /36

    $1,450,000 Pending

    • 5 Beds
    • 3.5 Baths

    642 Ash St, Winnetka, IL 60093

    Location, curb appeal and charm - all in one! This East Winnetka home welcomes you with a large front porch and bright foyer leading to a spacious living room with fireplace and room for two seating areas. French doors open to a deck, flooding the space with light. The large kitchen and family room anchor the rear of the house with windows on three sides, a generous eat-in area, and direct access

    Annika Valdiserri @properties Christie's International Real Estate

    642 Ash 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 $1,508,407

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

    1166 Cherry St, Winnetka, IL 60093
    • /22

      Est $1,434,077 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

      • 44% Above List Price
      • $257/SF
      • 7 Days On Market
      • Last Sold Price $995,000
      • Sep 06, 2023

      Last Listing Agent Gloria Matlin Compass

  • /28

    $1,550,000 Pending

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

    764 Boal Pkwy, Winnetka, IL 60093

    Set amidst a stunning wooded backdrop between the tranquil Skokie Lagoons and the lush Winnetka Golf Club, this remarkable home offers three bedrooms and 3.1 baths across more than 3,000 square feet of thoughtfully designed living space. Situated at the end of a peaceful lane, the setting is as serene as it is beautiful. The interiors feature exceptional open spaces with elegant hardwood floors

    Gloria Matlin Compass

    764 Boal Pkwy, 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 $5,626,486

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

    125 Birch St, Winnetka, IL 60093
    • /31

      Est $480,114 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

      • 3% Above List Price
      • $374/SF
      • 0 Days On Market
      • Last Sold Price $465,000
      • Jun 14, 2023

      Last Listing Agent David Korkoian Redfin Corporation

  • /42

    $1,089,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,435 Sq Ft

    1105 Elm St, Winnetka, IL 60093

    Welcome to this truly charming, picture-perfect home in an unbeatable walk-to-everything location. The beautifully designed first floor showcases an elegant living room with fireplace that flows effortlessly into the dining room, highlighted by stunning built-ins. The inviting family room-also featuring custom built-ins-is the perfect place to gather and opens seamlessly to a sleek, thoughtfully

    Joanne Hudson Compass

    1105 Elm St, 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 $2,046,073

    Last Listing Agent Michael Kelly Compass

    803 Pine St, Winnetka, IL 60093
    • /39

      Est $1,251,720 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

      • 9% Above List Price
      • $371/SF
      • 4 Days On Market
      • Last Sold Price $1,151,000
      • Nov 01, 2024

      Last Listing Agent Melissa Dondalski @ Properties

  • /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
  • /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 $839,476

    Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

    640 Winnetka Mews Unit 105, Winnetka, IL 60093
    • /46

      Est $1,608,480 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

      • 10% Above List Price
      • $379/SF
      • 2 Days On Market
      • Last Sold Price $1,460,000
      • Nov 15, 2024

      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 $1,781,539 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

      • 9% Above List Price
      • $594/SF
      • 4 Days On Market
      • Last Sold Price $1,635,000
      • Sep 13, 2023

      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 $2,081,229

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

    386 Fairview Ave, Winnetka, IL 60093

Showing Results 121 - 160, Page 4 of 18

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