Winnetka, IL Homes

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  $599,999 Open Sat 11AM - 1PM

  • 2 Beds
  • 3.5 Baths
  • 1,364 Sq Ft

  97 High St, Winnetka, IL 60093

  A rare opportunity has arisen to acquire a 2-bedroom, 3.5-bathroom, full basement end unit townhouse in the esteemed neighborhood of Winnetka, conveniently located near Indian Hill Club, Joseph Sears school district, New Trier Township High School, The Kenilworth Beach, Indian Hill Metra Station Zone C, and more. This charming end-unit townhouse boasts all wood floors, a wood burning fireplace in

  

  Lilia Balan

  Pavlova Properties

  (224) 504-1146

  97 High St, Winnetka, IL 60093
• Explore Winnetka

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  /5

  $1,845 per month

  458 Winnetka Ave

  Studio - 2 Beds

  458 Winnetka Ave, Winnetka, IL 60093

  Renovated 1 bedroom in a well run vintage two story building! . Hardwood floors. Bright apartment w large picture windows, Eat in kitchen with dishwasher and microwave. Large bedroom (with closet) fitting for even a king size bed. Large bathroom.Heat and water included. Clean and tidy laundry room in building plus bike storage. Classic, original details combine with fresh updates to

  458 Winnetka Ave, 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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  /20

  Est $1,086,686 Not Listed For Sale

  624 Elder Ln, Winnetka, IL 60093

  • 2 Beds
  • 3 Baths
  • 1,956 Sq Ft
  • Built 1926

  624 Elder Ln, Winnetka, IL 60093

  Last Sold Summary

  • 9% Above List Price
  • $511/SF
  • 4 Days On Market

  Last Sold Price $1,000,000

  Last Listing Agent Cathy Deutsch @ Properties
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  $1,850,000

  • 5 Beds
  • 6 Baths
  • 3,921 Sq Ft

  1333 Tower Rd, Winnetka, IL 60093

  Step into a beautifully transformed Hemphill home in Winnetka with private access to the Forest Glen neighborhood. Modern updates meet classic character following extensive 2023 renovations, including new electrical and plumbing, an improved floor plan, bay windows, and new exterior doors-while preserving original plaster crown moldings and the signature wrought-iron staircase. Thoughtful design

  Marta Lazic Redfin Corporation

  1333 Tower Rd, Winnetka, IL 60093
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  $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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  $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 $1,185,094

  Last Listing Agent Dinny Dwyer Compass

  1288 Sunview Ln, Winnetka, IL 60093
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  Est $2,211,965 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

  • 22% Above List Price
  • $532/SF
  • 57 Days On Market

  Last Sold Price $1,810,000

  Last Listing Agent Jeannie Kurtzhalts Baird Warner
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  $3,495,000

  • 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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  $1,895 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  894 Green Bay Rd Unit 896B-17, Winnetka, IL 60093

  Renovated 2 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 896B-17, 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 $7,083,823

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

  381 Sheridan Rd, Winnetka, IL 60093
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  /20

  Est $871,710 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

  • 10% Above List Price
  • $454/SF
  • 3 Days On Market

  Last Sold Price $792,000

  Last Listing Agent Laura McCain Compass
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  $2,885,000 Pending

  • 6 Beds
  • 5.5 Baths
  • 7,200 Sq Ft

  985 Pine Tree Ln, Winnetka, IL 60093

  Set on a half-acre, this custom-built 5+ bedroom, 5.1 bath home offers elegant design, well-proportioned rooms, generous light, and spaces that feel both beautiful and comfortable from the moment you walk in. Rooms flow easily for entertaining a crowd, yet the home never loses its sense of warmth for everyday living. Sunlight fills the foyer, highlighting the striking staircase and spacious two

  Howard Meyers Compass

  985 Pine Tree Ln, Winnetka, IL 60093
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  $1,645 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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  $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 $1,836,000

  Last Listing Agent Grace Goro Compass

  917 Willow Rd, Winnetka, IL 60093
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  /22

  Est $625,414 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% Above List Price
  • $367/SF
  • 38 Days On Market

  Last Sold Price $615,000

  Last Listing Agent Katie Marx Coldwell Banker Realty
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  $2,295,000

  • 6 Beds
  • 5.5 Baths
  • 3,504 Sq Ft

  410 Cedar St, Winnetka, IL 60093

  Welcome to 410 Cedar in East Winnetka. This spectacular residence is a timeless all brick and stone home with wonderfully curated living spaces. From its stately curb appeal to its refined interior details this home sits sits on a 80' extra wide corner lot. Built in 2002 this six-bedroom, five-and-a-half-bath home offers an exceptional lifestyle for the most discerning buyer. The main level

  Annika Valdiserri @properties Christie's International Real Estate

  410 Cedar St, Winnetka, IL 60093
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  $1,595 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  916 Green Bay Rd Unit 918-G, 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-G, Winnetka, IL 60093
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  $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 $1,558,250

  Last Listing Agent Patricia Skirving Compass

  605 Lincoln Ave, Winnetka, IL 60093
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  Est $727,123 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

  • 11% Above List Price
  • $340/SF
  • 120 Days On Market

  Last Sold Price $657,000

  Last Listing Agent Vickie Liu Baird Warner
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  $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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  $1,595 per month

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

  918 Green Bay Rd Unit G, Winnetka, IL 60093

  AWESOME Winnetka one bedroom GARDEN apartment on beautiful tree lined street! Unit features hardwood floors, dishwasher, good natural light and a big closet. 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 Rosewood Beach

  Renee Pehanich Fulton Grace Realty

  918 Green Bay Rd Unit G, Winnetka, IL 60093
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  $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 $2,889,670

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

  674 Hill Rd, Winnetka, IL 60093
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  Est $4,081,837 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

  • 21% Above List Price
  • $259/SF
  • 91 Days On Market

  Last Sold Price $3,360,000

  Last Listing Agent Linda Martin Coldwell Banker Realty
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  /31

  $2,995,000

  • 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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  $1,625 per month

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

  916 Green Bay Rd, Winnetka, IL 60093

  Book a tour with the link belowWelcome to your ideal rental in the charming district of Winnetka, IL! This inviting property features comfortable living spaces that are perfect for anyone seeking a vibrant neighborhood close to local amenities.Key property features include bedrooms and bathrooms that offer privacy and functionality, along with a spacious floor area

  916 Green Bay Rd, Winnetka, IL 60093
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  $1,500,000 Sold May 01, 2025

  965 Spruce St, Winnetka, IL 60093

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

  Last Sold Summary

  • 3% Above List Price
  • $500/SF
  • 18 Days On Market

  Current Estimated Value $1,634,556

  Last Listing Agent Glenn Pankau Compass

  965 Spruce St, Winnetka, IL 60093
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  Est $3,217,217 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

  • 8% Below List Price
  • $473/SF
  • 52 Days On Market

  Last Sold Price $3,500,000

  Last Listing Agent Derek Schiller Derek E. Schiller
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  $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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  $8,200 per month

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • Townhouse for Rent

  932 Westmoor Rd Unit 936, Winnetka, IL 60093

  Beautiful townhome in the heart of Winnetka; close to beach, parks, schools, Metra station, restaurants and shops. Open floor layout perfect for everyday modern living, including 10-foot ceilings, custom cabinets, top-of-the-line appliances (Sub-Zero, Bosch, Thermador), hardwood floors & more. The second floor has a Master suite, a guest suite, and a laundry room. Third floor loft great for study

  Rita Rezko Coldwell Banker Realty

  932 Westmoor Rd Unit 936, Winnetka, IL 60093
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  $575,000 Sold Mar 31, 2025

  606 Lincoln Ave Unit 606, Winnetka, IL 60093

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Built 1956

  Last Sold Summary

  • 10% Above List Price
  • $383/SF
  • 0 Days On Market

  Current Estimated Value $573,440

  Last Listing Agent Sara Sullivan Compass

  606 Lincoln Ave Unit 606, Winnetka, IL 60093
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  Est $1,980,464 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

  • 15% Above List Price
  • $470/SF
  • 8 Days On Market

  Last Sold Price $1,720,000

  Last Listing Agent Lori Nieman @ Properties
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  $2,995,000 Pending

  • 5 Beds
  • 6 Baths
  • 7,070 Sq Ft

  Unlisted Address

  Magnificent East Winnetka! Truly exquisite, move-in ready, gorgeous brick Colonial, set on a panoramic 2/3 acre property, steps to Lake Michigan and downtown Hubbard Woods...an unparalleled fusion of luxury and functional comfort. This 5BD (all on one level) /4.2BA home boasts over 7000+ sq ft and seamlessly combines an open concept floor plan and fantastic indoor/outdoor lifestyle. Exceptional

  Paige Dooley Compass

  Unlisted Address
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  $7,500 per month

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  761 Cherry St Unit Townhome, Winnetka, IL 60093

  Lease available starting June 1st! Renovated and Furnished 3BR / 3BA Luxury Residence – Prime Winnetka LocationFully renovated in 2019, this sophisticated three-bedroom, three-bath first floor residence offers refined North Shore living in the heart of Winnetka.Thoughtfully redesigned with all new finishes, kitchen, baths, fixtures, and systems, the home combines modern elegance with

  761 Cherry St Unit Townhome, 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 $1,151,943

  Last Listing Agent Carly Jones Engel & Voelkers Chicago North Shore

  886 Willow Rd, Winnetka, IL 60093
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  Est $942,672 Not Listed For Sale

  1103 Willow Rd, Winnetka, IL 60093

  • 3 Beds
  • 1.5 Baths
  • 1,637 Sq Ft
  • Built 1951

  1103 Willow Rd, Winnetka, IL 60093

  Last Sold Summary

  • 19% Above List Price
  • $483/SF
  • 2 Days On Market

  Last Sold Price $790,000

  Last Listing Agent David Chung Compass
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  /31

  $2,149,900 Pending

  • 4 Beds
  • 5 Baths
  • 3,800 Sq Ft

  598 Birch St, Winnetka, IL 60093

  There is no better in-town location than this "like new" construction, transitional jewel box beauty. Delivering chic, youthful living with a very high-end, hotel vibe, all wrapped up on a fab block with a rare heated driveway & attached two-car garage-ready for winter weather! This superior smart-tech build has been outfitted to perfection with floor-to-ceiling black iron windows, natural oak

  Jena Radnay @properties Christie's International Real Estate

  598 Birch St, Winnetka, IL 60093
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  $50,000 per month

  • 6 Beds
  • 9 Baths
  • 8,000 Sq Ft
  • House for Rent

  919 Hill Rd, Winnetka, IL 60093

  An extraordinary "boutique hotel" living experience, impeccably situated in the heart of Winnetka. Beyond a stately solid-iron gate adorned with gold medallion accents lies a private sanctuary just 18 miles from Chicago and less than half a mile from the sandy shores of Lake Michigan. Evoking the glamour and grandeur of a Roaring Twenties estate, this remarkable residence channels the elegance of

  Carrie Tarzon @properties Christie's International Real Estate

  919 Hill 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 $1,957,339

  Last Listing Agent Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
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  Est $587,850 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

  Last Listing Agent Tim Ratty Baird Warner

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