Winnetka, IL Homes

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  /29

  $1,095,000 Pending

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

  1523 Tower Rd, Winnetka, IL 60093

  Meticulously maintained central-entry brick Colonial in the sought-after Hubbard Woods School District. Offering grand living spaces filled with natural light, this 4-bedroom, 3-bath home truly checks every box. A gracious foyer opens to the inviting living room, featuring a wood-burning fireplace, abundant windows, and custom built-in cabinetry. The separate dining room, with French doors leads

  

  Mary Grant

  @properties Christie's International Real Estate

  (224) 808-3652

  1523 Tower Rd, Winnetka, IL 60093
• Explore Winnetka

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  /2

  $1,745 Per Month

  • Studio
  • 1 Bath
  • Condo for Rent

  731 Elm St Unit 733-301, Winnetka, IL 60093

  Charming Studio apartment features hardwood floors, updated kitchen and bath. Pets welcome. Close to Metra, restaurants, grocery and more. Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.

  (224) 526-8227

  731 Elm St Unit 733-301, Winnetka, IL 60093
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  $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 $2,804,253

  Last Listing Agent Nicole Hajdu Baird & Warner

  205 Scott Ave, Winnetka, IL 60093
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  /29

  Est $2,145,594 Not Listed For Sale

  1060 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,400 Sq Ft
  • Built 2007

  1060 Spruce St, Winnetka, IL 60093

  Last Sold Summary

  • 19% Above List Price
  • $532/SF
  • 57 Days On Market

  • Last Sold Price $1,810,000
  • May 23, 2023

  Last Listing Agent Jeannie Kurtzhalts Baird Warner
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  /50

  $2,499,900 Pending

  • 6 Beds
  • 6 Baths
  • 5,458 Sq Ft

  406 Woodley Woods, Winnetka, IL 60093

  MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 4/24/26! Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal

  Jason Wagner Greystone Realty

  406 Woodley Woods, Winnetka, IL 60093
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  $1,770 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  916 Green Bay Rd Unit 918-2L, Winnetka, IL 60093

  Charming 1 bedroom apartment in Winnetka! Unit features hardwood floors, spacious living area. Electric heat. Close to Metra, Hubbard Woods Park, grocery, restaurants and more! Presented by Fulton Grace, Chicago IL. *Pictures may be of a similar unit in building.

  (224) 505-2588

  916 Green Bay Rd Unit 918-2L, Winnetka, IL 60093
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  /2

  $875,000 Sold Jan 12, 2026

  1288 Sunview Ln, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 2,714 Sq Ft
  • Built 1955

  Last Sold Summary

  • 27% Below List Price
  • $322/SF
  • 158 Days On Market

  Current Estimated Value $1,248,626

  Last Listing Agent Dinny Dwyer Compass

  1288 Sunview Ln, Winnetka, IL 60093
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  /20

  Est $838,013 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

  • 6% Above List Price
  • $454/SF
  • 3 Days On Market

  • Last Sold Price $792,000
  • Oct 02, 2023

  Last Listing Agent Laura McCain Compass
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  /72

  $2,750,000

  • 4 Beds
  • 6 Baths
  • 4,225 Sq Ft

  42 Woodley Rd, Winnetka, IL 60093

  Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

  Peggy Lewis @properties Christie's International Real Estate

  42 Woodley Rd, Winnetka, IL 60093
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  /6

  $1,770 Per Month

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

  918 Green Bay Rd Unit 2, Winnetka, IL 60093

  Property Id: 2512509UNIT FEATURES:* Hardwood Floors* Dishwasher* Mini Blinds* Ceiling Fans* Plenty of Closet SpaceSunshine dancing in little strips on the hardwood floors, elegant crown moldings, a fireplace, and airy living spaces - this apartment unit combines all these features and more. The ambiance is delightful and welcoming, while the living room

  (224) 505-1923

  918 Green Bay Rd Unit 2, Winnetka, IL 60093
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  $9,575,000 Sold Jun 06, 2025

  381 Sheridan Rd, Winnetka, IL 60093

  • 5 Beds
  • 8 Baths
  • 8,086 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $1,184/SF
  • 25 Days On Market

  Current Estimated Value $6,259,666

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

  381 Sheridan Rd, Winnetka, IL 60093
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  /22

  Est $604,216 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

  • 2% Below List Price
  • $367/SF
  • 38 Days On Market

  • Last Sold Price $615,000
  • Jan 06, 2025

  Last Listing Agent Katie Marx Coldwell Banker Realty
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  /41

  $3,599,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 5,499 Sq Ft

  Unlisted Address

  Beautifully designed ranch by renowned architect Tony Grunsfeld, perfectly situated on a private street and a spacious half-acre lot. This remarkable 4+bedroom, 4.1-bath home combines timeless architecture with thoughtful modern updates, offering comfortable, elegant living in one of the North Shore's most sought-after locations. The newly updated kitchen is the heart of the home, featuring all

  Jody Dickstein @properties Christie's International Real Estate

  Unlisted Address
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  /14

  $2,220 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.

  (224) 328-1582

  545 Chestnut St Unit 545-301, Winnetka, IL 60093
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  $1,675,000 Sold Aug 28, 2025

  917 Willow Rd, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 4,352 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $385/SF
  • 38 Days On Market

  Current Estimated Value $1,705,000

  Last Listing Agent Grace Goro Compass

  917 Willow Rd, Winnetka, IL 60093
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  /41

  Est $710,804 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

  • 8% Above List Price
  • $340/SF
  • 120 Days On Market

  • Last Sold Price $657,000
  • Nov 22, 2023

  Last Listing Agent Vickie Liu Baird Warner
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  /2

  $2,799,388 New Construction

  • 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 and vaulted second-floor

  John Park John Park

  510 Provident Ave, Winnetka, IL 60093
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  /22

  $10,500 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,090 Sq Ft
  • House for Rent

  1094 Pine St, Winnetka, IL 60093

  If you are hoping for a gorgeous high level rental in the coveted Village of Winnetka, look no further! Pristine and private, this stunning French Provincial home has been meticulously updated, with attention to every detail. Highlighting the entry is a lovely sweeping staircase with a glimpse into the spacious sophisticated living room beyond. A stately fireplace and bay window draws you in to

  Anne Malone Engel & Voelkers Chicago North Shore

  1094 Pine St, Winnetka, IL 60093
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  /49

  $1,520,000 Sold Aug 12, 2025

  605 Lincoln Ave, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,000 Sq Ft
  • Built 1914

  Last Sold Summary

  • 17% Above List Price
  • $507/SF
  • 5 Days On Market

  Current Estimated Value $1,549,458

  Last Listing Agent Patricia Skirving Compass

  605 Lincoln Ave, Winnetka, IL 60093
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  /2

  Est $3,716,145 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

  • 11% Above List Price
  • $259/SF
  • 91 Days On Market

  • Last Sold Price $3,360,000
  • Dec 30, 2024

  Last Listing Agent Linda Martin Coldwell Banker Realty
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  $2,489,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,680 Sq Ft

  1241 Ash St, Winnetka, IL 60093

  This extraordinary residence, originally dating to the 1920s and completely rebuilt in 2010-including a fully excavated lower level-offers an exceptional blend of timeless architectural character and refined modern luxury across four impeccably finished levels. Set on an expansive 75 x 187 lot, the stately brick exterior, enhanced by a handsome porte cochere, creates a memorable and elegant

  Joanne Hudson Compass

  1241 Ash St, Winnetka, IL 60093
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  /2

  $1,995

  Total Monthly Price

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

  811 Elm St Unit A07C, Winnetka, IL 60093

  Winnetka817 Elm , Unit 205Beds:1Baths:1Rent:Sq.Ft:700Available:No

  811 Elm St Unit A07C, 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 $2,862,116

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

  674 Hill Rd, Winnetka, IL 60093
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  /5

  Est $3,136,767 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

  • 10% Below List Price
  • $473/SF
  • 52 Days On Market

  • Last Sold Price $3,500,000
  • Sep 27, 2024

  Last Listing Agent Derek Schiller Derek E. Schiller
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  /31

  $2,995,000 Pending

  • 5 Beds
  • 6.5 Baths

  4 Indian Hill Rd, Winnetka, IL 60093

  Welcome to this Margaret McCurry designed 5 bedroom, 6 bathroom home with a primary suite on the first floor and golf simulator and extensive lower level recreation area. Tucked off Indian Hill golf course on a special little lane, it's all here in this custom built home w/first floor primary bedroom with a spectacular floor plan and sliding doors that can define the rooms. One of a kind design

  Kathryn Mangel @properties Christie's International Real Estate

  4 Indian Hill Rd, Winnetka, IL 60093
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  /8

  $1,770 Per Month

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

  918 Green Bay Rd Unit 2L, Winnetka, IL 60093

  ***Part sublet, part regular lease. Sublet 6/1-6/30, Rent is 1770-. Regular lease 7/1/26 - 6/30/27, Rent is 1895-.*** AWESOME Winnetka one bedroom apartment in walk up building on beautiful tree lined street! Unit features hardwood floors, dishwasher, good natural light and a lots of closet space. No AC, need to get window unit. Courtyard Building has shared laundry on site and Bike Room. Steps

  Renee Pehanich Fulton Grace Realty

  918 Green Bay Rd Unit 2L, Winnetka, IL 60093
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  $1,100,000 Sold Aug 01, 2025

  886 Willow Rd, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 2,534 Sq Ft
  • Built 1910

  Last Sold Summary

  • $434/SF
  • 19 Days On Market

  Current Estimated Value $1,146,906

  Last Listing Agent Carly Jones Engel & Voelkers Chicago North Shore

  886 Willow Rd, Winnetka, IL 60093
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  /30

  Est $1,944,755 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

  • 13% Above List Price
  • $470/SF
  • 8 Days On Market

  • Last Sold Price $1,720,000
  • Jun 28, 2023

  Last Listing Agent Lori Nieman @ Properties
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  /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
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  $1,750 - $2,195

  Total Monthly Price

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

  894 Green Bay Rd, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets

  894 Green Bay Rd, Winnetka, IL 60093
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  $1,900,000 Sold Jul 10, 2025

  475 Maple St, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,524 Sq Ft
  • Built 1888

  Last Sold Summary

  • 5% Below List Price
  • $539/SF
  • 19 Days On Market

  Current Estimated Value $1,928,606

  Last Listing Agent Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
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  /16

  Est $585,403 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

  • 12% Above List Price
  • $292/SF
  • 6 Days On Market

  • Last Sold Price $525,000
  • Aug 29, 2023

  Last Listing Agent Tim Ratty Baird Warner
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  $2,439,000 Pending

  • 4 Beds
  • 7 Baths
  • 4,269 Sq Ft

  1185 Hill Rd, Winnetka, IL 60093

  Idyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully designed for both everyday living and exceptional entertaining. The home features a sought-after first-floor primary suite plus an additional bedroom with full ensuite bath in that wing of the home. An outstanding chef's kitchen with top-of-the-line appliances, generous workspace, and a spacious breakfast

  Joanne Hudson Compass

  1185 Hill Rd, Winnetka, IL 60093
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  /10

  $1,595 Per Month

  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

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

  REMODELED Winnetka studio apartment on beautiful tree lined street! Unit features Hardwood Floors, Breakfast Bar, SS Appliances, Dishwasher, Lots of Natural Light and Laundry in Unit. No AC, need to get window unit. Courtyard Building has shared laundry on site and Bike Room. Steps to Hubbard Woods Metra Stop. Nearby Hubbard Woods Plaza, less than a 5 min walk. Tower Road Park Beach is a super

  Renee Pehanich Fulton Grace Realty

  918 Green Bay Rd Unit 3C, Winnetka, IL 60093
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  $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 $2,456,508

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

  107 Woodley Rd, Winnetka, IL 60093
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  Est $2,821,026 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

  • 3% Above List Price
  • $477/SF
  • 5 Days On Market

  • Last Sold Price $2,750,000
  • Apr 18, 2025

  Last Listing Agent Paige Dooley Compass
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  $2,495,000 Pending

  • 5 Beds
  • 5 Baths
  • 4,597 Sq Ft

  845 Glen Oak Dr, Winnetka, IL 60093

  Located in a superb East Winnetka location this 4 bedroom 3.2 bath lovely classic Hemphill built home boasts 3 car attached garage and an elevator. Glen Oak Drive is a private cul-de-sac street on the lake east of Sheridan Road with only 5 stately homes. A separate circular drive & double door entry leads into a large and gracious foyer with pretty moldings and staircase. When you step into the

  Kathryn Mangel @properties Christie's International Real Estate

  845 Glen Oak Dr, Winnetka, IL 60093
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  $1,750 - $2,195

  Total Monthly Price

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

  894 Green Bay Rd, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 2 bedroom apartment in Winnetka! Features hardwood floors, spacious living area, updated kitchen & bath. Laundry available on-site. Pets

  894 Green Bay Rd, Winnetka, IL 60093
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  $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 $1,967,306

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

  1215 Spruce St, Winnetka, IL 60093
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  /23

  Est $928,296 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

  • 2% Below List Price
  • $486/SF
  • 1 Day On Market

  • Last Sold Price $950,000
  • Nov 04, 2024

  Last Listing Agent Paige Dooley Compass

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