5,354

Winnetka, IL Homes

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  • /2

    $2,799,388

    New Construction Pending
    • 6 Beds
    • 5.5 Baths

    510 Provident Ave, Winnetka, IL 60093

    Situated on a quiet, highly desirable street in the heart of Winnetka, 510 Provident represents a thoughtful expression of modern North Shore architecture - where structural integrity, material quality, and enduring design converge. This new construction home offers six-bedrooms, six baths, over-scaled proportions and architectural clarity throughout. Ten-foot ceilings create an elevated sense of

    John Park John Park

    510 Provident Ave, Winnetka, IL 60093
  • /14

    $2,150 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    545 Chestnut St Unit 545-301, Winnetka, IL 60093

    Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry in-unit. Pet friendly building. Great location close to Dwyer Park, Metra, restaurants and shopping! Presented by Fulton Grace, Chicago IL.*Pictures may be of a similar unit in building.

    545 Chestnut St Unit 545-301, Winnetka, IL 60093
  • /72

    $1,795,000

    Sold Apr 03, 2026

    567 Hill Terrace, Winnetka, IL 60093

    • 4 Beds
    • 3.5 Baths
    • 3,662 Sq Ft
    • Built 1924

    Last Sold Summary

    • 6% Above List Price
    • $490/SF
    • 4 Days On Market

    Current Estimated Value $1,787,185

    Last Listing Agent Lauren Schuh-Dayton Jameson Sotheby's Intl Realty

    567 Hill Terrace, Winnetka, IL 60093
    • /5

      Est $3,102,628

      Not Listed For Sale

      269 Woodlawn Ave, Winnetka, IL 60093

      • 5 Beds
      • 6.5 Baths
      • 7,400 Sq Ft
      • Built 2024
      269 Woodlawn Ave, Winnetka, IL 60093

      Last Sold Summary

      • 52 Days On Market

  • /38

    $3,495,000

    • 6 Beds
    • 7.5 Baths
    • 8,303 Sq Ft

    1015 Sheridan Rd, Winnetka, IL 60093

    Nestled on a private lane east of Sheridan Road, this distinguished Winnetka residence offers privacy, scale, quality craftsmanship, and exceptional everyday livability in one of the North Shore's most coveted east-side locations. Designed for elegant entertaining, multigenerational living, work-from-home flexibility, and relaxed daily comfort, the home features 6+ bedrooms, including a private

    Linda Martin Coldwell Banker Realty

    1015 Sheridan Rd, Winnetka, IL 60093
  • /13

    $1,795 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Condo for Rent

    918 Green Bay Rd Unit 3A, Winnetka, IL 60093

    Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your ideal rental in the charming district of Winnetka, IL. This property offers a fantastic living experience in a vibrant community, close to an array of excellent restaurants and department stores. You'll appreciate the convenience of

    918 Green Bay Rd Unit 3A, Winnetka, IL 60093
  • /2

    $3,100,000

    Sold Feb 17, 2026

    Unlisted Address

    • 6 Beds
    • 7 Baths
    • 5,338 Sq Ft
    • Built 1915

    Last Sold Summary

    • 3% Below List Price
    • $581/SF
    • 16 Days On Market

    Current Estimated Value $3,147,518

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

    Unlisted Address
    • /30

      Est $2,032,874

      Not Listed For Sale

      285 Woodlawn Ave, Winnetka, IL 60093

      • 4 Beds
      • 5.5 Baths
      • 3,656 Sq Ft
      • Built 2007
      285 Woodlawn Ave, Winnetka, IL 60093

      Last Sold Summary

      • 8 Days On Market

  • /36

    $1,399,000

    • 4 Beds
    • 3.5 Baths
    • 3,992 Sq Ft

    1225 Elm St, Winnetka, IL 60093

    Privately tucked on an extra wide 1/3rd acre property, this fully re-imagined mid-century modern home offers exceptional design and incredible vistas of its lushly landscaped property. Thoughtfully curated with attention to detail and a sophisticated eye for design, the home blends timeless architecture with abundant natural beauty, right in the heart of Winnetka. A super chic, modern kitchen

    Paige Dooley Compass

    1225 Elm St, Winnetka, IL 60093
  • /10

    $2,150 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    545 Chestnut St Unit 301, Winnetka, IL 60093

    Property Id: 2608527Welcome to your new home at 545 Chestnut St., #301 in Winnetka, IL! This charming 1 bed/1 bath apartment features hardwood floors, radiant heating, and a washer/dryer in unit. Pets are welcome, with cats and small dogs allowed. Rent includes garbage, sewage, and water. Don't miss out on this cozy unit for $2150/month. Make it yours starting June 15, 2026!

    545 Chestnut St Unit 301, Winnetka, IL 60093
  • /7

    $2,350,000

    Sold Oct 24, 2025

    466 Chestnut St, Winnetka, IL 60093

    • 5 Beds
    • 5.5 Baths
    • 4,433 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $530/SF

    Current Estimated Value $2,299,697

    Last Listing Agent Robert Milkowski Berger & Co. Realtors Ltd

    466 Chestnut St, Winnetka, IL 60093
    • /16

      Est $601,790

      Not Listed For Sale

      680 Green Bay Rd Unit 201, Winnetka, IL 60093

      • 3 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1970
      680 Green Bay Rd Unit 201, Winnetka, IL 60093

      Last Sold Summary

      • 6 Days On Market

  • /27

    $825,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,938 Sq Ft

    376 Rosewood Ave, Winnetka, IL 60093

    Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning

    Courtney Elko Jameson Sotheby's International Realty

    376 Rosewood Ave, Winnetka, IL 60093
  • /18

    $2,220 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    545 Chestnut St Unit E545-301, Winnetka, IL 60093

    Actual Unit # *301*Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Comfortable and well-maintained apartment located in a convenient Chicago-area neighborhood. This unit offers a functional layout, spacious living areas, and easy access to shopping, dining, public transportation, parks,

    545 Chestnut St Unit E545-301, Winnetka, IL 60093
  • /29

    $1,103,000

    Sold May 13, 2026

    1523 Tower Rd, Winnetka, IL 60093

    • 4 Beds
    • 3 Baths
    • 2,503 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $441/SF
    • 5 Days On Market

    Current Estimated Value $1,106,368

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

    1523 Tower Rd, Winnetka, IL 60093
    • /53

      Est $2,809,866

      Not Listed For Sale

      201 Linden St, Winnetka, IL 60093

      • 6 Beds
      • 7 Baths
      • 5,761 Sq Ft
      • Built 1973
      201 Linden St, Winnetka, IL 60093

      Last Sold Summary

      • 5 Days On Market

  • /22

    $1,195,000

    • 3 Beds
    • 4 Baths
    • 2,717 Sq Ft

    72 Warwick Rd, Winnetka, IL 60093

    Ideally located in coveted East Winnetka, just moments from Joseph Sears School, Lake Michigan beaches, the Metra train, and New Trier High School's East Campus, this beautifully updated home offers the perfect combination of charm, functionality, and an unbeatable location. Featuring 3 bedrooms, 4 full bathrooms, and a flexible first-floor office or optional 4th bedroom, the home is thoughtfully

    Kathryn Mangel @properties Christie's International Real Estate

    72 Warwick Rd, Winnetka, IL 60093
  • /13

    $1,930

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    921 Green Bay Rd Unit 3G, Winnetka, IL 60093

    UPDATED APARTMENTS:- Hardwood Floors- Restored Wood Trim- Updated Kitchen- SS Appliances- Washer/Dryer Combo- Dishwasher- Quartz Countertop- Backsplash- Updated Bathroom- Mini Blinds- Ceiling Fans- Plenty of Closet SpaceBUILDING FEATURES:- On-site Laundry- Cable/Internet Ready- Water Included- Individual Electric Heater per

    921 Green Bay Rd Unit 3G, Winnetka, IL 60093
  • /26

    $1,190,000

    Sold Jul 17, 2025

    812 Rosewood Ave, Winnetka, IL 60093

    • 4 Beds
    • 3.5 Baths
    • 2,646 Sq Ft
    • Built 1917

    Last Sold Summary

    • 4% Below List Price
    • $450/SF
    • 96 Days On Market

    Current Estimated Value $1,291,185

    Last Listing Agent Jackie Mack Jameson Sotheby's International Realty

    812 Rosewood Ave, Winnetka, IL 60093
    • /23

      Est $950,873

      Not Listed For Sale

      660 Winnetka Mews Unit 214, Winnetka, IL 60093

      • 3 Beds
      • 3 Baths
      • 1,955 Sq Ft
      • Built 1973
      660 Winnetka Mews Unit 214, Winnetka, IL 60093

      Last Sold Summary

      • 1 Day On Market

  • /78

    $4,500,000

    Pending
    • 6 Beds
    • 7 Baths
    • 6,212 Sq Ft

    140 Birch St, Winnetka, IL 60093

    Set behind mature landscaping on a breathtaking and rarely available full acre, this extraordinary Winnetka residence offers the kind of space, privacy, and walk-to-everything convenience that almost never coexist. Thoughtfully reimagined through a complete gut renovation and expansion in 2010-including a new lower level, this 6-bedroom, 5.2-bath home lives beautifully for today while honoring

    Julie Miller Compass

    140 Birch St, Winnetka, IL 60093
  • /14

    $1,885

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    731 Elm St Unit 302, Winnetka, IL 60093

    WINNETKA STUDIOS & 1BRSAPARTMENT FEATURES:- Hardwood Floors- Dishwasher- Mini Blinds- Ceiling Fans- Plenty of Closet SpaceBUILDING FEATURES:- On-site Laundry- Cable/Internet Ready- Water Included- Individual Electric Heater per Unit- Heat, Electricity and Cooking Gas not IncludedPET INFO:- Cats Allowed- Dogs Allowed- 2

    731 Elm St Unit 302, Winnetka, IL 60093
  • /19

    $1,117,000

    Sold Mar 11, 2026

    380 Green Bay Rd Unit 1B, Winnetka, IL 60093

    • 2 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • Built 1997

    Last Sold Summary

    • 16% Above List Price
    • $573/SF
    • 1 Day On Market

    Current Estimated Value $1,083,539

    Last Listing Agent Julie Miller Compass

    380 Green Bay Rd Unit 1B, Winnetka, IL 60093
    • /2

      Est $1,714,077

      Not Listed For Sale

      1133 Scott Ave, Winnetka, IL 60093

      • 5 Beds
      • 4.5 Baths
      • 5,300 Sq Ft
      • Built 1923
      1133 Scott Ave, Winnetka, IL 60093

      Last Sold Summary

      • 4 Days On Market

  • /26

    $1,439,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 3,465 Sq Ft

    373 Sunset Rd, Winnetka, IL 60093

    Welcome to 373 Sunset Road, an spacious 5-bedroom, 3.1-bath brick and frame home in sought-after East Winnetka. Ideally located near Greeley Elementary, New Trier High School, the Indian Hill Metra, and just moments from Lake Michigan beaches, this home offers a wonderful blend of classic architecture and exceptional space. The gracious floor plan features a welcoming foyer, office/music room,

    Joanne Hudson Compass

    373 Sunset Rd, Winnetka, IL 60093
  • /33

    $1,545 - $1,930

    Total Monthly Price

    • Studio - 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    924 Green Bay Rd, Winnetka, IL 60093

    924 Green Bay Rd, Winnetka, IL 60093
  • /19

    $985,000

    Sold Nov 20, 2025

    785 Locust St, Winnetka, IL 60093

    • 3 Beds
    • 1.5 Baths
    • 1,224 Sq Ft
    • Built 1911

    Last Sold Summary

    • 12% Above List Price
    • $805/SF
    • 12 Days On Market

    Current Estimated Value $1,009,071

    Last Listing Agent Crawford Group @properties Christie's International Real Estate

    785 Locust St, Winnetka, IL 60093
    • /38

      Est $3,656,962

      Not Listed For Sale

      745 Sheridan Rd, Winnetka, IL 60093

      • 6 Beds
      • 7.5 Baths
      • 9,930 Sq Ft
      • Built 1990
      745 Sheridan Rd, Winnetka, IL 60093

      Last Sold Summary

      • 251 Days On Market

  • /37

    $1,299,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,316 Sq Ft

    1295 Sunview Ln, Winnetka, IL 60093

    Exciting chance to refashion this light-filled ranch home to your personal vision. Large windows throughout the home offer beautiful views and light. The spacious kitchen opens to the vaulted family room. The master bedroom and second bedroom are on the first floor, plus two full baths, family room, living room, dining room, and screened porch. Outdoors, there is an expansive stone patio and pond

    Margaret Goss @properties Christie's International Real Estate

    1295 Sunview Ln, Winnetka, IL 60093
  • /16

    $2,250

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Condo for Rent

    953 Westmoor Rd Unit 1, Winnetka, IL 60093

    Beautiful and bright 3 Bedroom unit with large private patio. Hardwood floors throughout and bedrooms upstairs. One and one half baths and in unit laundry. One garage spot included and easy street parking. Living room dining room opens to the stone patio. Updated kitchen with stainless steel appliances. Master bedroom and 2 large bedrooms - good closet space and storage in the attic with pull

    953 Westmoor Rd Unit 1, Winnetka, IL 60093
  • /41

    $1,550,000

    Sold Apr 30, 2026

    1004 Elm St, Winnetka, IL 60093

    • 5 Beds
    • 3.5 Baths
    • 3,047 Sq Ft

    Last Sold Summary

    • 7% Above List Price
    • $509/SF
    • 9 Days On Market

    Current Estimated Value $1,466,741

    Last Listing Agent Stephanie Cutter Coldwell Banker Realty

    1004 Elm St, Winnetka, IL 60093
    • /46

      Est $2,194,481

      Not Listed For Sale

      17 Longmeadow Rd, Winnetka, IL 60093

      • 7 Beds
      • 7 Baths
      • 6,000 Sq Ft
      • Built 1966
      17 Longmeadow Rd, Winnetka, IL 60093

      Last Sold Summary

      • 31 Days On Market

  • /16

    $285,000

    Open Sun 12PM - 2PM
    • 2 Beds
    • 1 Bath

    1101 Merrill St Unit M1, Winnetka, IL 60093

    Rarely available 2 bed/1 bath condominium in the heart of Hubbard Woods, just steps from the Metra, shops, restaurants, cafes, and Lake Michigan. This beautifully refreshed home features new windows, freshly painted interiors, hardwood floors throughout, an updated bath, and a kitchen with granite countertops and newer stainless steel appliances. A separate dining room offers flexible space for

    Julie Cassin @properties Christie's International Real Estate

    1101 Merrill St Unit M1, Winnetka, IL 60093
  • /8

    $1,595

    Total Monthly Price

    • Studio
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    915 Green Bay Rd Unit 3C, Winnetka, IL 60093

    UPDATED STUDIOS & 1BRS IN THE HEART OF WINNETKAUPDATED APARTMENTS:- Hardwood Floors- Restored Wood Trim- Updated Kitchen- SS Appliances- Washer/Dryer Combo- Dishwasher- Quartz Countertop- Backsplash- Updated Bathroom- Mini Blinds- Ceiling Fans- Plenty of Closet SpaceBUILDING FEATURES:- On-site Laundry- Cable/Internet

    915 Green Bay Rd Unit 3C, Winnetka, IL 60093
  • /2

    $935,000

    Sold Jul 30, 2025

    1442 Asbury Ave, Winnetka, IL 60093

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1925

    Last Sold Summary

    • $413/SF
    • 4 Days On Market

    Current Estimated Value $1,029,798

    Last Listing Agent Sherry Molitor Compass

    1442 Asbury Ave, Winnetka, IL 60093
    • /15

      Est $223,185

      Not Listed For Sale

      561 Hill Terrace Unit 310, Winnetka, IL 60093

      • 1 Bed
      • 1 Bath
      • 500 Sq Ft
      • Built 1928
      561 Hill Terrace Unit 310, Winnetka, IL 60093

      Last Sold Summary

      • 67 Days On Market

  • /43

    $4,200,000

    $300K PRICE DROP
    • 6 Beds
    • 9 Baths
    • 6,950 Sq Ft

    1128 Mount Pleasant Rd, Winnetka, IL 60093

    Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after

    Eugene Fu @properties Christie's International Real Estate

    1128 Mount Pleasant Rd, Winnetka, IL 60093
  • /33

    $1,545 - $1,930

    Total Monthly Price

    • Studio - 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    924 Green Bay Rd, Winnetka, IL 60093

    924 Green Bay Rd, Winnetka, IL 60093
  • /2

    $750,000

    Sold Jul 03, 2025

    736 Oak St Unit 736, Winnetka, IL 60093

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1965

    Last Sold Summary

    • 19% Above List Price
    • $469/SF
    • 1 Day On Market

    Current Estimated Value $739,971

    Last Listing Agent David Chung Compass

    736 Oak St Unit 736, Winnetka, IL 60093
    • /9

      Est $1,440,865

      Not Listed For Sale

      338 Linden St, Winnetka, IL 60093

      • 3 Beds
      • 3 Baths
      • 2,407 Sq Ft
      • Built 1962
      338 Linden St, Winnetka, IL 60093

      Last Sold Summary

      • 0 Days On Market

Showing Results 41 - 80, Page 2 of 18

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