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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  /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.

  545 Chestnut St Unit 545-301, 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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  /53

  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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  /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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  /17

  $1,895 Per Month

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

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

  UNIT FEATURES:* 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 SpaceSunshine dancing in little strips on the hardwood floors, elegant crown moldings, a fireplace, and airy living spaces - this

  918 Green Bay Rd Unit 2D, 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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  /10

  Est $1,095,765 Not Listed For Sale

  826 Humboldt Ave, Winnetka, IL 60093

  • 3 Beds
  • 1.5 Baths
  • 1,059 Sq Ft
  • Built 1913

  826 Humboldt Ave, Winnetka, IL 60093

  Last Sold Summary

  • 55% Above List Price
  • $666/SF
  • 873 Days On Market

  • Last Sold Price $705,000
  • May 01, 2025

  Last Listing Agent Paul Harb Wilmette Real Estate & Management Company LLC
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  /73

  $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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  /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.

  731 Elm St Unit 733-301, 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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  /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
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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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  /2

  $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.

  916 Green Bay Rd Unit 918-2L, Winnetka, IL 60093
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  /15

  $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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  /18

  Est $1,603,247 Not Listed For Sale

  965 Spruce St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • Built 1886

  965 Spruce St, Winnetka, IL 60093

  Last Sold Summary

  • 7% Above List Price
  • $500/SF
  • 18 Days On Market

  • Last Sold Price $1,500,000
  • May 01, 2025

  Last Listing Agent Glenn Pankau Compass
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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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  /11

  $2,220 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  545 Chestnut St Unit 301, Winnetka, IL 60093

  UNIT FEATURES:* Hardwood Floors* Updated Bathroom* On-Site Laundry* Dining Area* Separate Kitchen* Ceiling Fans* Mini Blinds* Pet-Friendly (Call for Details)* PHOTOS MAY BE STOCK OR OF A SIMILAR UNIT IN THE BUILDING.Disclaimer: The Apartment SourceCall or text:

  545 Chestnut St Unit 301, 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 $1,545,640

  Last Listing Agent Patricia Skirving Compass

  605 Lincoln Ave, Winnetka, IL 60093
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  /2

  Est $453,000 Not Listed For Sale

  35 Indian Hill Rd, Winnetka, IL 60093

  • 7 Beds
  • 9 Baths
  • 9,744 Sq Ft
  • Built 1927

  35 Indian Hill Rd, Winnetka, IL 60093

  Last Sold Summary

  • 90% Below List Price
  • $462/SF
  • 45 Days On Market

  • Last Sold Price $4,500,000
  • Apr 18, 2025

  Last Listing Agent Nancy Nugent Jameson Sotheby's Intl Realty
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  /64

  $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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  /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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  /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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  /2

  Est $1,527,489 Not Listed For Sale

  1050 Elm St, Winnetka, IL 60093

  • 4 Beds
  • 2.5 Baths
  • 2,737 Sq Ft
  • Built 1904

  1050 Elm St, Winnetka, IL 60093

  Last Sold Summary

  • 2% Above List Price
  • $549/SF
  • 3 Days On Market

  • Last Sold Price $1,502,000
  • Apr 30, 2025

  Last Listing Agent Howard Meyers Compass
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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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  /65

  $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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  /35

  $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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  /9

  Est $1,566,963 Not Listed For Sale

  843 Cherry St, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • Built 1916

  843 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 3% Above List Price
  • $508/SF
  • 15 Days On Market

  • Last Sold Price $1,525,000
  • Apr 18, 2025

  Last Listing Agent James Qiu Kale Realty
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  /45

  $2,299,000 Pending

  • 6 Beds
  • 7 Baths
  • 5,350 Sq Ft

  1423 Asbury Ave, Winnetka, IL 60093

  Better than NEW! This artfully restored & renovated home has the incredible combination of a classic center entry colonial home with sophisticated formal rooms and all the current amenities for today's modern lifestyle. This four-level home features abundant natural light, oversized windows, wide room openings and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end

  Laura McCain Compass

  1423 Asbury Ave, 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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  /52

  $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 $1,933,360

  Last Listing Agent Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
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  /82

  Est $1,833,079 Not Listed For Sale

  705 Oak St, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,377 Sq Ft
  • Built 2001

  705 Oak St, Winnetka, IL 60093

  Last Sold Summary

  • 11% Above List Price
  • $489/SF
  • 33 Days On Market

  • Last Sold Price $1,650,000
  • Apr 22, 2025

  Last Listing Agent Christopher Paul Redfin Corporation
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  /36

  $2,175,000 Pending

  • 5 Beds
  • 5 Baths
  • 4,214 Sq Ft

  1255 Forest Glen Dr N, Winnetka, IL 60093

  Classic Hemphill Colonial on an oversized 75-foot-wide lot, completely renovated in 2014 with all the charm of a 1950s home but the newness of newer construction. What you will love is this home is all done for you with all the must haves that are hard to find- like attached garage, mudroom, high ceilings, newer windows, designer kitchen, dream primary suite, 2nd floor laundry, huge basement with

  Bonnie Tripton @properties Christie's International Real Estate

  1255 Forest Glen Dr N, 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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  /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 $2,456,508

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

  107 Woodley Rd, Winnetka, IL 60093
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  Est $2,604,375 Not Listed For Sale

  345 Birch St, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 4,713 Sq Ft
  • Built 1965

  345 Birch St, Winnetka, IL 60093

  Last Sold Summary

  • 5% Above List Price
  • $525/SF

  • Last Sold Price $2,475,000
  • Apr 30, 2025

  Last Listing Agent Jena Radnay @ Properties
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  /48

  $2,245,000

  • 5 Beds
  • 4.5 Baths
  • 4,390 Sq Ft

  1159 Chatfield Rd, Winnetka, IL 60093

  Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and

  Jason Rowland Compass

  1159 Chatfield Rd, Winnetka, IL 60093
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  /15

  $2,045 Per Month

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

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

  REMODELED Winnetka one bedroom apartment on beautiful tree lined street! Unit features hardwood floors, 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 close and

  Renee Pehanich Fulton Grace Realty

  918 Green Bay Rd Unit 3G, 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 $1,967,306

  Last Listing Agent Megan Mawicke Jameson Sotheby's International Realty

  1215 Spruce St, Winnetka, IL 60093
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  /36

  Est $1,539,914 Not Listed For Sale

  838 Cherry St, Winnetka, IL 60093

  • 4 Beds
  • 4 Baths
  • 3,510 Sq Ft
  • Built 1997

  838 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 6% Above List Price
  • $413/SF
  • 13 Days On Market

  • Last Sold Price $1,450,000
  • Apr 21, 2025

  Last Listing Agent Beverly Fleischman Coldwell Banker Realty

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