Winnetka, IL Homes

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  /18

  $5,975,000

  New Construction

  • 7 Beds
  • 8.5 Baths
  • 11,000 Sq Ft

  455 Sheridan Rd, Winnetka, IL 60093

  New magnificent transitional home with approximately 11,000 square feet finished space. Exterior is constructed of brick and limestone with slate roof which represents timeless construction. Close to Plaza del Lago with its numerous shops and restaurants, Kenilworth beach, schools and train the house features 7 bedrooms, 8.1 bath, 3 fireplaces, spectacular kitchen with top-of-the-line appliances

  Milena Birov @properties Christie's International Real Estate

  455 Sheridan Rd, Winnetka, IL 60093
• Explore Winnetka

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  /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
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  /58

  $2,750,000

  Sold Feb 13, 2026

  205 Scott Ave, Winnetka, IL 60093

  • 5 Beds
  • 5 Baths
  • 6,162 Sq Ft
  • Built 1933

  Last Sold Summary

  • 4% Below List Price
  • $446/SF
  • 21 Days On Market

  Current Estimated Value $2,817,009

  Last Listing Agent Nicole Hajdu Baird & Warner

  205 Scott Ave, Winnetka, IL 60093
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  /63

  Est $2,528,539

  Not Listed For Sale

  1300 Hackberry Ln, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,973 Sq Ft
  • Built 1953

  1300 Hackberry Ln, Winnetka, IL 60093

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty
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  /24

  $1,100,000

  Pending

  • 4 Beds
  • 1.5 Baths
  • 2,308 Sq Ft

  592 Provident Ave, Winnetka, IL 60093

  Charming House in Winnetka with Timeless Appeal Welcome to this charming four-bedroom, 1 1/2 bath Winnetka home that beautifully blends classic character with comfortable, inviting living spaces. Warm and welcoming from the moment you walk past the stately over four-hundred-year-old Burr Oak in the front yard, this home offers a wonderful combination of livability and an in-town location.

  Constance Browne Coldwell Banker Realty

  592 Provident Ave, Winnetka, IL 60093
• 

  

  /13

  $1,895 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  894 Green Bay Rd Unit 896A-09, Winnetka, IL 60093

  Renovated 1 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets welcome. Close to Hubbard Woods Park, Metra, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.

  894 Green Bay Rd Unit 896A-09, Winnetka, IL 60093
• 

  

  /19

  $400,134

  Sold Jul 29, 2026

  134 Green Bay Rd Unit 104, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Above List Price
  • $294/SF
  • 4 Days On Market

  Current Estimated Value $363,035

  Last Listing Agent Dinny Dwyer Compass

  134 Green Bay Rd Unit 104, Winnetka, IL 60093
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  /32

  Est $1,853,405

  Not Listed For Sale

  1473 Edgewood Ln, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 2,826 Sq Ft
  • Built 1925

  1473 Edgewood Ln, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Alicja Skibicki Baird & Warner
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  /36

  $899,000

  Pending

  • 3 Beds
  • 1.5 Baths

  790 Foxdale Ave, Winnetka, IL 60093

  A rare opportunity on one of Winnetka's most beloved neighborhood streets. Welcome to 790 Foxdale Avenue, a charming Dutch Colonial offering timeless character, a wonderful sense of community and an exceptional location in the sought-after Greeley Elementary attendance area and New Trier High School district. Foxdale is more than just a beautiful tree-lined street-it's the kind of block where

  Cory Green Compass

  790 Foxdale Ave, Winnetka, IL 60093
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  /2

  $2,350 Per Month

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

  814 Elm St Unit 602, Winnetka, IL 60093

  AVAILABLE NOVEMBER! Incredible one bedroom, one bathroom in heart of downtown Winnetka features rehabbed kitchen with stainless steel appliances, dishwasher, spacious living area, large bedroom, great closet space, rehabbed bathroom, hardwood floors throughout, laundry in unit, and pets are welcome! Steps to Winnetka Metra stop, shops, restaurants, Public Library, and a couple blocks to the

  814 Elm St Unit 602, Winnetka, IL 60093
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  /84

  $4,300,000

  Sold Aug 14, 2026

  605 Arbor Vitae Rd, Winnetka, IL 60093

  • 7 Beds
  • 5.5 Baths
  • 5,228 Sq Ft
  • Built 1915

  Last Sold Summary

  • 12% Above List Price
  • $822/SF
  • 2 Days On Market

  Current Estimated Value $3,794,948

  Last Listing Agent Megan Panje-Wilson Jameson Sotheby's International Realty

  605 Arbor Vitae Rd, Winnetka, IL 60093
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  /32

  Est $2,968,276

  Not Listed For Sale

  1010 Hubbard Place, Winnetka, IL 60093

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft
  • Built 1925

  1010 Hubbard Place, Winnetka, IL 60093

  Last Sold Summary

  Last Listing Agent Elise Rinaldi @properties Christie's International Real Estate
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  /51

  $4,500,000

  • 6 Beds
  • 9 Baths
  • 7,480 Sq Ft

  1380 Westmoor Trail, Winnetka, IL 60093

  Phenomenal value as this finely built newer construction home privately set with serene panoramic Winnetka Golf Club vistas just hit "elevated luxury" status with an impeccable 2026 no expense spared rehab. Starting off with the new stunning Chef's kitchen that radiates with extra-thick Taj Mahal honed quartzite c-tops, Perrin & Rowe fixtures, Frankie sink, Visual Comfort brushed brass pendants &

  Jena Radnay @properties Christie's International Real Estate

  1380 Westmoor Trail, Winnetka, IL 60093
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  /18

  $1,895 Per Month

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

  946 Green Bay Rd Unit 90A, Winnetka, IL 60093

  AVAILABLE NOW! Peaceful one bedroom, one bathroom in beautiful Winnetka courtyard building features newer kitchen with stainless steel appliances, dishwasher, large combination living and dining rooms with ceiling fan, spacious bedroom, great closet space, newer bathroom, hardwood floors throughout, laundry room in building, and pets welcome! Steps to Hubbard Woods Metra stop and a block to the

  946 Green Bay Rd Unit 90A, Winnetka, IL 60093
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  /5

  $5,600,000

  Sold Feb 26, 2026

  674 Hill Rd, Winnetka, IL 60093

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft
  • Built 1916

  Last Sold Summary

  • 32% Above List Price
  • $622/SF
  • 16 Days On Market

  Current Estimated Value $5,357,519

  Last Listing Agent Lori Neuschel @properties Christie's International Real Estate

  674 Hill Rd, Winnetka, IL 60093
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  /61

  Est $2,757,327

  Not Listed For Sale

  321 Woodland Ave, Winnetka, IL 60093

  • 6 Beds
  • 5 Baths
  • 4,698 Sq Ft
  • Built 2000

  321 Woodland Ave, Winnetka, IL 60093

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Carrie McCormick @properties Christie's International Real Estate
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  /21

  $2,785,000

  • 6 Beds
  • 5.5 Baths

  82 Woodley Rd, Winnetka, IL 60093

  Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush,

  Michael Mitchell @properties Christie's International Real Estate

  82 Woodley Rd, Winnetka, IL 60093
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  /9

  $1,950 Per Month

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

  809 Elm St Unit 4, Winnetka, IL 60093

  Winnetka 2 Bedroom 1 Bathroom **Charming Apartment Living in Fabulous Downtown Winnetka!** Modern comfort meets the vibrant lifestyle of downtown Winnetka. Nestled in an unbeatable location, this beautifully updated apartment offers an ideal balance of style and convenience, perfect for urban dwellers seeking a welcoming retreat. **Key Features:** - **Gourmet Kitchen**: Step into your renovated

  809 Elm St Unit 4, Winnetka, IL 60093
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  /55

  $3,799,000

  Sold Aug 26, 2026

  785 Mount Pleasant St, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 3,487 Sq Ft
  • Built 2008

  Last Sold Summary

  • $1,089/SF
  • 3 Days On Market

  Current Estimated Value $2,934,278

  Last Listing Agent Paige Dooley Compass

  785 Mount Pleasant St, Winnetka, IL 60093
• 

  

  /20

  Est $922,151

  Not Listed For Sale

  812 Oak St Unit 201, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,745 Sq Ft
  • Built 1997

  812 Oak St Unit 201, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Laura McCain Compass
• 

  

  /23

  $1,250,000

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

  640 Winnetka Mews Unit 403, Winnetka, IL 60093

  Be prepared to be impressed by this rarely available, beautifully updated top-floor 4 bedroom, 3 bath residence in the historic Winnetka Mews, perfectly positioned with a Pine Street exposure. Thoughtfully renovated with exceptional attention to detail, this sun drenched home combines gracious living spaces, timeless finishes and an abundance of thoughtfully designed storage. At the heart of the

  Jenny Fisher @properties Christie's International Real Estate

  640 Winnetka Mews Unit 403, Winnetka, IL 60093
• 

  

  /13

  $1,795 Per Month

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

  918 Green Bay Rd Unit 3E, 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 next home in the charming district of Winnetka, IL! This delightful property offers a comfortable living space near a variety of local amenities, including popular restaurants and department stores. Enjoy the convenience of nearby

  918 Green Bay Rd Unit 3E, Winnetka, IL 60093
• 

  /2

  $1,890,008

  Sold May 18, 2026

  67 Brier St, Winnetka, IL 60093

  • 5 Beds
  • 6 Baths
  • 4,200 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $450/SF
  • 34 Days On Market

  Current Estimated Value $1,863,251

  Last Listing Agent Nehru Arunasalam @properties Christie's International Real Estate

  67 Brier St, Winnetka, IL 60093
• 

  

  /22

  Est $1,247,500

  Not Listed For Sale

  812 Oak St Unit 200, Winnetka, IL 60093

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

  812 Oak St Unit 200, Winnetka, IL 60093

  Last Sold Summary

  • 5 Days On Market

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

  

  /10

  $1,200,000

  Pending

  • 5 Beds
  • 3.5 Baths

  590 Willow Rd, Winnetka, IL 60093

  ***Build your dream home!!!*** Amazing opportunity in the East Winnetka neighborhood, tear down and build your forever home! Original 1913 home standing on 11,555 sf 70x165 Corner LOT. Prime Winnetka location, walking distance to lake, parks, school, Metra stop and downtown Winnetka. 'As-IS/Where-Is' Estate Sale.

  Edith Schell @properties Christies International Real Estate

  590 Willow Rd, Winnetka, IL 60093
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  /8

  $1,950 Per Month

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

  809 Elm St Unit 2, Winnetka, IL 60093

  Winnetka - 2 Bedroom 1 Bathroom **Charming Apartment Living in Fabulous Downtown Winnetka!** Modern comfort meets the vibrant lifestyle of downtown Winnetka. Nestled in an unbeatable location, this beautifully updated apartment offers an ideal balance of style and convenience, perfect for urban dwellers seeking a welcoming retreat. **Key Features:** - **Gourmet Kitchen**: Step into your renovated

  809 Elm St Unit 2, Winnetka, IL 60093
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  /56

  $2,450,000

  Sold Oct 06, 2025

  107 Woodley Rd, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 5,001 Sq Ft
  • Built 1956

  Last Sold Summary

  • 14% Above List Price
  • $490/SF
  • 8 Days On Market

  Current Estimated Value $2,618,113

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

  107 Woodley Rd, Winnetka, IL 60093
• 

  

  /22

  Est $639,555

  Not Listed For Sale

  720 Green Bay Rd Unit 3B, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 2007

  720 Green Bay Rd Unit 3B, Winnetka, IL 60093

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Katie Marx Coldwell Banker Realty
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  /65

  $1,999,000

  Open Sun 10AM - 12PM

  • 5 Beds
  • 5 Baths
  • 3,914 Sq Ft

  1288 Sunview Ln, Winnetka, IL 60093

  Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been transformed from top to bottom with a focus on design, functionality and quality, creating a home that feels entirely new while maintaining the character and setting of the original property. The spacious floor plan offers 5 bedrooms, 3 full

  Mike LeFevere Compass

  1288 Sunview Ln, Winnetka, IL 60093
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  /16

  $2,695 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Condo for Rent

  545 Chestnut St Unit E811-209, Winnetka, IL 60093

  Actual Unit # *E811-209* 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 E811-209, Winnetka, IL 60093
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  /34

  $2,195,000

  Sold Aug 14, 2026

  757 Locust St, Winnetka, IL 60093

  • 6 Beds
  • 6 Baths
  • 4,142 Sq Ft
  • Built 1920

  Last Sold Summary

  • $530/SF
  • 3 Days On Market

  Current Estimated Value $2,181,390

  Last Listing Agent Christie Ascione @properties Christie's International Real Estate

  757 Locust St, Winnetka, IL 60093
• 

  

  /13

  Est $530,767

  Not Listed For Sale

  720 Green Bay Rd Unit 2E, Winnetka, IL 60093

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 2007

  720 Green Bay Rd Unit 2E, Winnetka, IL 60093

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Marjorie Richter Baird & Warner
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  /41

  $2,695,000

  • 4 Beds
  • 4.5 Baths
  • 4,509 Sq Ft

  1140 Oakley Ave, Winnetka, IL 60093

  A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins.

  Anne Maitland Jameson Sotheby's International Realty

  1140 Oakley Ave, Winnetka, IL 60093
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  /2

  $1,950 Per Month

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

  809 Elm St Unit 3, Winnetka, IL 60093

  Notable 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 3, Winnetka, IL 60093
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  /59

  $2,000,000

  Sold Apr 01, 2026

  1215 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,633 Sq Ft
  • Built 1955

  Last Sold Summary

  • $551/SF
  • 6 Days On Market

  Current Estimated Value $2,042,278

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

  1215 Spruce St, Winnetka, IL 60093
• 

  

  /41

  Est $788,148

  Not Listed For Sale

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft
  • Built 2007

  720 Green Bay Rd Unit 2D, Winnetka, IL 60093

  Last Sold Summary

  • 120 Days On Market

  Last Listing Agent Vickie Liu Baird & Warner
• 

  

  /50

  $2,800,000

  Pending

  • 4 Beds
  • 5 Baths
  • 7,500 Sq Ft

  64 Locust Rd, Winnetka, IL 60093

  A rare Winnetka offering, this distinguished 1965 Hemphill-built Georgian residence showcases exceptional main-level living on a spectacular one-acre property. With a primary suite and two additional bedrooms on the first floor, the home embraces the ease of living predominantly on one level while retaining the scale, privacy and timeless North Shore architecture for which Hemphill homes are

  Monica Childs @properties Christie's International Real Estate

  64 Locust Rd, Winnetka, IL 60093
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  /14

  $1,995 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
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  /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 $1,814,186

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

  567 Hill Terrace, Winnetka, IL 60093
• 

  /2

  Est $4,254,396

  Not Listed For Sale

  104 Longmeadow Rd, Winnetka, IL 60093

  • 7 Beds
  • 8.5 Baths
  • 12,998 Sq Ft
  • Built 2008

  104 Longmeadow Rd, Winnetka, IL 60093

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Linda Martin Coldwell Banker Realty

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