5,224

Winnetka, IL Homes

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  • /8

    $2,595,000

    • Land
    • 1.45 Acres
    • $1,789,655 per Acre

    61 Woodley Rd, Winnetka, IL 60093

    Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own

    Stephen Todd Jameson Sotheby's Intl Realty

    61 Woodley Rd, Winnetka, IL 60093
  • /20

    $2,695 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    814 Elm St Unit 902, Winnetka, IL 60093

    AVAILABLE OCTOBER! Handsome two bedroom, one bathroom in heart of downtown Winnetka features rehabbed kitchen with espresso cabinets, stainless steel appliances, dishwasher, large combination living and dining rooms with ceiling fan, spacious bedrooms, great closet space, rehabbed bathroom, hardwood floors throughout, laundry in unit, and pets welcome! Steps to Winnetka Metra stop, shops,

    814 Elm St Unit 902, 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 $3,213,093

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

    Unlisted Address
    • /5

      Est $3,467,211

      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

      Last Listing Agent Derek Schiller Derek E. Schiller

  • /46

    $2,000,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,662 Sq Ft

    579 Hill Terrace, Winnetka, IL 60093

    **Multiple Offers Received** Highest and Best due Tuesday 9/15 by 9am** A rare expression of extraordinary North Shore living, this quintessential red-brick Colonial sits on a 100' x 175' double lot (.39 of an acre) on coveted Hill Terrace, one of Winnetka's prettiest private lanes, in an A+ walk-to-everything location. Designed by prolific architect Bertram A. Weber, this much-loved residence

    Susan Sullivan @properties Christie's International Real Estate

    579 Hill Terrace, Winnetka, IL 60093
  • /20

    $2,250 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    946 Green Bay Rd Unit 61B, Winnetka, IL 60093

    AVAILABLE NOW! Tremendous two bedroom, one bathroom in beautiful Winnetka courtyard building features newer eat in kitchen with dishwasher, large combination living and dining rooms with decorative fireplace, spacious bedrooms, great closet space, newer bathroom, hardwood floors throughout, laundry room in building, and pets are welcome! Steps to Hubbard Woods Metra stop and a block to the Beach!

    946 Green Bay Rd Unit 61B, 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 $2,395,155

    Last Listing Agent Robert Milkowski Berger & Co. Realtors Ltd

    466 Chestnut St, Winnetka, IL 60093
    • /51

      Est $5,853,940

      Not Listed For Sale

      139 Sheridan Rd, Winnetka, IL 60093

      • 5 Beds
      • 8 Baths
      • 9,723 Sq Ft
      • Built 2021
      139 Sheridan Rd, Winnetka, IL 60093

      Last Sold Summary

      • 29 Days On Market

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

  • /45

    $1,950,000

    Pending
    • 5 Beds
    • 3 Baths
    • 3,280 Sq Ft

    1440 Tower Rd, Winnetka, IL 60093

    An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and

    Sarah Lyons @properties Christie's International Real Estate

    1440 Tower Rd, Winnetka, IL 60093
  • /2

    $1,950 Per Month

    • 2 Beds
    • 1 Bath
    • 604 Sq Ft
    • Condo for Rent

    809 Elm St Unit 5, Winnetka, IL 60093

    Outstanding two bedroom, one bathroom in the heart of downtown Winnetka features heat included, rehabbed kitchen with stainless steel appliances, dishwasher, spacious living area, large equal sized bedrooms, awesome closet space, hardwood flooring throughout, free laundry in building, storage, and cats are welcome! Steps to Winnetka Metra stop! Won't Last Long!

    809 Elm St Unit 5, 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 $1,173,097

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

    1523 Tower Rd, Winnetka, IL 60093
    • /53

      Est $2,779,899

      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

      Last Listing Agent Paige Dooley Compass

  • /58

    $4,200,000

    • 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
  • /10

    $2,495 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    894 Green Bay Rd Unit 896B-16, 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 this inviting rental property in the heart of Winnetka, IL, a charming district known for its vibrant community and proximity to essential amenities. This property offers a unique opportunity for comfortable living with easy access to an

    894 Green Bay Rd Unit 896B-16, 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 $1,060,052

    Last Listing Agent Julie Miller Compass

    380 Green Bay Rd Unit 1B, Winnetka, IL 60093
    • /28

      Est $871,948

      Not Listed For Sale

      640 Winnetka Mews Unit 105, Winnetka, IL 60093

      • 2 Beds
      • 2 Baths
      • 1,975 Sq Ft
      • Built 1971
      640 Winnetka Mews Unit 105, Winnetka, IL 60093

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

  • /44

    $1,725,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 6,580 Sq Ft

    555 Cherry St, Winnetka, IL 60093

    Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront

    Howard Meyers Compass

    555 Cherry St, Winnetka, IL 60093
  • /20

    $2,350 Per Month

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

    814 Elm St Unit 12, Winnetka, IL 60093

    AVAILABLE NOVEMBER! Great one bedroom, one bathroom in heart of downtown Winnetka features rehabbed kitchen with espresso cabinets, stainless steel appliances, dishwasher, separate formal dining room, large living room, spacious bedroom, great closet space, ceiling fans, new bathroom, hardwood floors throughout, laundry in unit, and pets are welcome! Steps to Winnetka Metra stop, shops,

    814 Elm St Unit 12, 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 $1,104,903

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

    785 Locust St, Winnetka, IL 60093
    • /23

      Est $991,425

      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

      Last Listing Agent Paige Dooley Compass

  • /33

    $1,649,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,215 Sq Ft

    870 Prospect Ave, Winnetka, IL 60093

    Enjoy an East Winnetka lifestyle on a beautifully landscaped expansive .3 acre all brick home in an ideal location, only blocks to Tower Road beach, Hubbard Woods/Winnetka shops and restaurants, schools, parks, and train. This sophisticated Georgian offering a great circular floorplan, grandly scaled rooms filled with natural light, fabulous outdoor spaces with a fully fenced yard, and an

    Eileen Collins Compass

    870 Prospect Ave, Winnetka, IL 60093
  • /2

    $1,895 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    918 Green Bay Rd Unit 2, Winnetka, IL 60093

    Notable one bedroom, one bathroom in Winnetka features newer kitchen with dishwasher, large combined living and dining rooms, spacious bedroom, great closet space, hardwood floors, rehabbed bathroom, laundry room in building, and pets are welcome. Steps to Hubbard Woods Metra stop, and a block to Tower Road Park Beach!

    Berthene Christos Urban Abodes Chicago

    918 Green Bay Rd Unit 2, 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 $1,565,281

    Last Listing Agent Stephanie Cutter Coldwell Banker Realty

    1004 Elm St, Winnetka, IL 60093
    • /2

      Est $1,828,265

      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

      Last Listing Agent Sherry Molitor Compass

  • /43

    $2,569,900

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

    62 Woodley Rd, Winnetka, IL 60093

    The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as

    Jena Radnay @properties Christie's International Real Estate

    62 Woodley Rd, Winnetka, IL 60093
  • /18

    $1,895

    Total Monthly Price

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

    694 Green Bay Rd Unit J08P, Winnetka, IL 60093

    694 Green Bay Rd Unit J08P, Winnetka, IL 60093
  • /22

    $261,000

    Sold Oct 31, 2025

    1101 Merrill St Unit M1, Winnetka, IL 60093

    • 2 Beds
    • 1 Bath

    Last Sold Summary

    • 5% Below List Price
    • 30 Days On Market

    Current Estimated Value $279,271

    Last Listing Agent Hilde Wheeler Carter Coldwell Banker Realty

    1101 Merrill St Unit M1, Winnetka, IL 60093
    • /38

      Est $3,610,764

      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

      Last Listing Agent Vaciliki Ress Berkshire Hathaway HomeServices Chicago

  • /3

    $1,290,000

    • Land
    • 1.36 Acres
    • $948,529 per Acre

    2033 Winnetka Rd, Winnetka, IL 60093

    Reduced new price for the land is more than $100,000 less than the original !! Rare chance to own 1.36 acres of land on beautiful Winnetka rd will provide you endless possibilities to build your dream home. Incredible opportunity to collaborate with experienced luxury builder or bring your own builder. Winnetka High School District. Amazing location- close to Northfield Park District,Westfield

    Natalya Gorodetsky Core Realty & Investments, Inc

    2033 Winnetka Rd, Winnetka, IL 60093
  • /12

    $2,000 Per Month

    • 2 Beds
    • 1 Bath
    • 771 Sq Ft
    • Apartment for Rent

    909 Green Bay Rd Unit 3S, Winnetka, IL 60093

    This charming second-floor walk-up is ideally located in the heart of the Hubbard Woods Design District, near the train, restaurants, coffee shops, and boutique retail. The unit features classic vintage character, with double entry from the hall, two generously sized bedrooms, a large, inviting living area, and ample storage. Laundry is conveniently located one level down from the unit, on the

    Andra O'Neill @properties Christie's International Real Estate

    909 Green Bay Rd Unit 3S, Winnetka, IL 60093
  • /43

    $1,515,000

    Sold Apr 30, 2026

    916 Oak St, Winnetka, IL 60093

    • 4 Beds
    • 2.5 Baths
    • 2,116 Sq Ft
    • Built 1911

    Last Sold Summary

    • 8% Above List Price
    • $716/SF
    • 4 Days On Market

    Current Estimated Value $1,528,043

    Last Listing Agent Joanne Hudson Compass

    916 Oak St, Winnetka, IL 60093
    • /46

      Est $2,210,646

      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

      Last Listing Agent Daniel Mirea Berkshire Hathaway HomeServices Chicago

  • /14

    $16,900,000

    • 6 Beds
    • 10 Baths
    • 15,000 Sq Ft

    915 Sunset Rd, Winnetka, IL 60093

    A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value

    Mary Maris Village Realty Group Inc

    915 Sunset Rd, Winnetka, IL 60093
  • /29

    $1,895 - $2,250

    Total Monthly Price

    • 1 - 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    894 Green Bay Rd, Winnetka, IL 60093

    Renovated vintage courtyard building in the heart of the Hubbard Woods district of Winnetka.

    894 Green Bay Rd, Winnetka, IL 60093
  • /49

    $1,875,000

    Sold Apr 24, 2026

    1092 Ash St, Winnetka, IL 60093

    • 4 Beds
    • 3 Baths
    • 3,622 Sq Ft
    • Built 1926

    Last Sold Summary

    • 6% Above List Price
    • $518/SF

    Current Estimated Value $1,883,094

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

    1092 Ash St, Winnetka, IL 60093
    • /15

      Est $223,846

      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

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

  • /41

    $1,779,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,950 Sq Ft

    639 Lincoln Ave, Winnetka, IL 60093

    Nestled in an exceptional location, this beautifully appointed home offers the perfect combination of charm, comfort, and convenience. Just moments from vibrant downtown Winnetka, you'll enjoy easy access to outstanding restaurants, boutique shopping, the train station, and the beach-making it easy to embrace the very best of the community. Inside, the thoughtfully designed floor plan features

    Anne Malone Engel & Voelkers Chicago North Shore

    639 Lincoln Ave, 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
  • /33

    $1,305,000

    Sold May 15, 2026

    1505 Tower Rd, Winnetka, IL 60093

    • 4 Beds
    • 4 Baths
    • 3,225 Sq Ft
    • Built 1943

    Last Sold Summary

    • 31% Above List Price
    • $405/SF
    • 3 Days On Market

    Current Estimated Value $1,290,762

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

    1505 Tower Rd, Winnetka, IL 60093
    • /9

      Est $1,508,603

      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

      Last Listing Agent Christina Fawcett @properties Christie's International Real Estate

Showing Results 41 - 80, Page 2 of 18

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