Winnetka, IL Homes

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  /60

  $4,995,000

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

  1380 Westmoor Trail, Winnetka, IL 60093

  It is exceptionally rare to find a privately set masterpiece with sweeping views of the Winnetka Golf Course that also offers the opportunity to step directly into a freshly completed 2025/2026 designer showcase renovation. Nestled on a beautifully landscaped half-acre site overlooking the golf course, this extraordinary stone residence has been impeccably transformed through a comprehensive

  Lori Nieman @properties Christie's International Real Estate

  1380 Westmoor Trail, Winnetka, IL 60093
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  /14

  $1,885

  Total Monthly Price

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

  731 Elm St Unit 302, Winnetka, IL 60093

  WINNETKA STUDIOS & 1BRSAPARTMENT FEATURES:- Hardwood Floors- Dishwasher- Mini Blinds- Ceiling Fans- Plenty of Closet SpaceBUILDING FEATURES:- On-site Laundry- Cable/Internet Ready- Water Included- Individual Electric Heater per Unit- Heat, Electricity and Cooking Gas not IncludedPET INFO:- Cats Allowed- Dogs Allowed- 2

  731 Elm St Unit 302, Winnetka, IL 60093
• 

  

  /2

  $31,250,000

  Sold Aug 29, 2025

  419 Sheridan Rd, Winnetka, IL 60093

  • 7 Beds
  • 13 Baths
  • 13,894 Sq Ft
  • Built 1928

  Last Sold Summary

  • 11% Below List Price
  • $2,249/SF
  • 145 Days On Market

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

  419 Sheridan Rd, Winnetka, IL 60093
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  /66

  Est $3,256,154

  Not Listed For Sale

  270 Birch St, Winnetka, IL 60093

  • 6 Beds
  • 8.5 Baths
  • 6,298 Sq Ft
  • Built 1927

  270 Birch St, Winnetka, IL 60093

  Last Sold Summary

  • 2 Days On Market
• 

  

  

  /42

  $1,425,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,163 Sq Ft

  1087 Ash St, Winnetka, IL 60093

  If you are looking for a right-size, upsize, or downsize home that can effortlessly adapt to your changing needs, you've found your dream home. 1087 Ash is pure perfection! There is so much more than meets the eye, as the substantial addition is beautifully tucked behind the original home. Step into the sunny three-season room - perfect for morning coffee or an afternoon mahj game - and sets the

  Leslie Maguire @properties Christie's International Real Estate

  1087 Ash St, Winnetka, IL 60093
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  /33

  $1,545 - $1,930

  Total Monthly Price

  • Studio - 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  924 Green Bay Rd, Winnetka, IL 60093

  924 Green Bay Rd, 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 $1,443,115

  Last Listing Agent Joanne Hudson Compass

  916 Oak St, Winnetka, IL 60093
• 

  

  /22

  Est $1,514,706

  Not Listed For Sale

  1028 Cherry St, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 2,711 Sq Ft
  • Built 1925

  1028 Cherry St, Winnetka, IL 60093

  Last Sold Summary

  • 0 Days On Market
• 

  

  /50

  $4,999,900

  Pending

  • 6 Beds
  • 6 Baths
  • 4,159 Sq Ft

  936 Sunset Rd, Winnetka, IL 60093

  Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES

  Jena Radnay @properties Christie's International Real Estate

  936 Sunset Rd, Winnetka, IL 60093
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  /19

  $1,895 Per Month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

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

  Superb one bedroom, one bathroom in Winnetka features newer kitchen with dishwasher, separate dining room, large living room with decorative fireplace, spacious bedroom with ceiling fan, great closet space, hardwood floors, newer 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 2L, Winnetka, IL 60093
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  /36

  $1,716,000

  Sold Aug 15, 2025

  567 Provident Ave, Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 3,747 Sq Ft
  • Built 2002

  Last Sold Summary

  • 11% Above List Price
  • $458/SF
  • 6 Days On Market

  Current Estimated Value $1,786,306

  Last Listing Agent Kathryn Moor Compass

  567 Provident Ave, Winnetka, IL 60093
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  /32

  Est $1,919,490

  Not Listed For Sale

  804 Boal Pkwy, Winnetka, IL 60093

  • 4 Beds
  • 3.5 Baths
  • 4,490 Sq Ft
  • Built 1955

  804 Boal Pkwy, Winnetka, IL 60093

  Last Sold Summary

  • 16 Days On Market
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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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  /20

  $1,645 Per Month

  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

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

  Memorable studio in Winnetka features brand new rehabbed kitchen with modern white cabinets, island with breakfast bar, stainless steel appliances, dishwasher, spacious living area with ceiling fan, great closet space, hardwood floors, rehabbed bathroom, laundry in unit, 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 3B, Winnetka, IL 60093
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  /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 $1,721,456

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

  1092 Ash St, Winnetka, IL 60093
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  /31

  Est $2,999,016

  Not Listed For Sale

  824 Boal Pkwy, Winnetka, IL 60093

  • 5 Beds
  • 7 Baths
  • 6,300 Sq Ft
  • Built 2019

  824 Boal Pkwy, Winnetka, IL 60093

  Last Sold Summary

  • 6 Days On Market
• 

  

  /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
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  /19

  $1,930 Per Month

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

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

  Outstanding one bedroom, one bathroom in Winnetka features brand new kitchen with modern white cabinets, stainless steel appliances, dishwasher, separate dining area with ceiling fan, large living room with decorative fireplace, spacious bedroom, great closet space, hardwood floors, new bathroom, laundry in unit, and pets are welcome. Steps to Hubbard Woods Metra stop, and a block to Tower Road

  Berthene Christos Urban Abodes Chicago

  918 Green Bay Rd Unit 3G, Winnetka, IL 60093
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  /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 $1,023,327

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

  1505 Tower Rd, Winnetka, IL 60093
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  /5

  Est $1,543,386

  Not Listed For Sale

  1501 Tower Rd, Winnetka, IL 60093

  • 4 Beds
  • 4.5 Baths
  • 3,462 Sq Ft
  • Built 1949

  1501 Tower Rd, Winnetka, IL 60093

  Last Sold Summary

  • 22 Days On Market
• 

  

  /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
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  /12

  $2,000 Per Month

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

  909 Green Bay Rd Unit 2S, 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 from the unit, on the same level. This

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

  909 Green Bay Rd Unit 2S, Winnetka, IL 60093
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  /2

  $950,000

  Sold Jan 20, 2026

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,062 Sq Ft
  • Built 1928

  Last Sold Summary

  • $461/SF
  • 2 Days On Market

  Current Estimated Value $1,084,997

  Last Listing Agent Susan Duffey @properties Christie's International Real Estate

  Unlisted Address
• 

  

  /28

  Est $1,305,739

  Not Listed For Sale

  1476 Scott Ave, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,970 Sq Ft
  • Built 1967

  1476 Scott Ave, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market
• 

  

  /26

  $3,200,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 3,683 Sq Ft

  48 Indian Hill Rd, Winnetka, IL 60093

  Tucked away in one of Winnetka's most coveted private roads, this exceptional 5-bedroom, 4.5-bathroom estate offers a prime spacious lot surrounded by majestic, mature trees. The property boasts an extraordinary setting that guarantees ultimate privacy while maximizing its unique geographic advantage. The home features dramatic, unobstructed vistas overlooking the historic Indian Hill Golf Course

  Joseph Nash @properties Christie's International Real Estate

  48 Indian Hill Rd, Winnetka, IL 60093
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  /2

  $1,770 Per Month

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

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

  Fantastic one bedroom, one bathroom in Winnetka features brand new kitchen with modern white cabinets, stainless steel appliances, dishwasher, separate dining area with ceiling fan, large living room with decorative fireplace, spacious bedroom, great closet space, hardwood floors, new bathroom, laundry in unit, and pets are welcome. Steps to Hubbard Woods Metra stop, and a block to Tower Road

  Berthene Christos Urban Abodes Chicago

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

  /2

  $910,000

  Sold Dec 17, 2025

  158 Woodland Ave, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Above List Price
  • $414/SF

  Current Estimated Value $949,064

  Last Listing Agent Catherine O'Connell @properties Christie's International Real Estate

  158 Woodland Ave, Winnetka, IL 60093
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  /59

  Est $1,608,474

  Not Listed For Sale

  1321 Scott Ave, Winnetka, IL 60093

  • 6 Beds
  • 5 Baths
  • 3,358 Sq Ft
  • Built 1928

  1321 Scott Ave, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market
• 

  

  /27

  $925,000

  Pending

  • 3 Beds
  • 1.5 Baths

  259 Church Rd, Winnetka, IL 60093

  Picture-perfect and move-in ready, this charming 3-bedroom, 1.1-bath home is nestled in one of Winnetka's most walkable locations. A welcoming, modern open floor plan flows from the foyer through the sun-drenched living room, surrounded by an abundance of windows and anchored by a wood-burning fireplace flanked by built-in bookcases. The chef's kitchen features solid white cabinetry, wood

  Lisa Weis @properties Christie's International Real Estate

  259 Church Rd, Winnetka, IL 60093
• 

  

  /20

  $1,795 Per Month

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

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

  Quality 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 3A, Winnetka, IL 60093
• 

  

  /44

  $3,750,000

  Sold Aug 01, 2025

  180 De Windt Rd, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 5,735 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $654/SF
  • 2 Days On Market

  Current Estimated Value $3,622,945

  Last Listing Agent Grace Goro Compass

  180 De Windt Rd, Winnetka, IL 60093
• 

  

  /10

  Est $1,080,422

  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

  • 873 Days On Market
• 

  

  /48

  $4,699,000

  Pending

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

  231 Woodlawn Ave, Winnetka, IL 60093

  Magnificent East Glencoe home- approximately 9,000 sf of total finished space. 6 BR all ensuite plus 3 additional half baths. Stone & brick exterior on over .5 acre lot. Close to train. Featuring a spectacular kitchen, media room, cherry library, workout room, sauna, wine cellar, and fully fenced expansive private outdoor living space with fireplace / TV and separate fire pit with seating area

  Craig Stone Stone Realty Group

  231 Woodlawn Ave, Winnetka, IL 60093
• 

  /2

  $4,700,000

  Sold Aug 05, 2025

  775 Sumac Ln, Winnetka, IL 60093

  • 5 Beds
  • 8.5 Baths
  • 6,240 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $753/SF
  • 9 Days On Market

  Current Estimated Value $4,745,505

  Last Listing Agent Annie flanagan @properties Christie's International Real Estate

  775 Sumac Ln, Winnetka, IL 60093
• 

  

  /26

  Est $1,630,453

  Not Listed For Sale

  850 Eldorado St, Winnetka, IL 60093

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1945

  850 Eldorado St, Winnetka, IL 60093

  Last Sold Summary

  • 3 Days On Market
• 

  

  /41

  $1,850,000

  • 3 Beds
  • 2.5 Baths
  • 4,356 Sq Ft

  180 Westview Rd, Winnetka, IL 60093

  BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale

  Cody McGuire @properties Commercial

  180 Westview Rd, Winnetka, IL 60093
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  /46

  $2,200,000

  Sold Oct 15, 2025

  1503 Edgewood Ln, Winnetka, IL 60093

  • 4 Beds
  • 5 Baths
  • 3,319 Sq Ft
  • Built 1927

  Last Sold Summary

  • 23% Above List Price
  • $663/SF
  • 3 Days On Market

  Current Estimated Value $2,093,617

  Last Listing Agent Sarah Lyons @properties Christie's International Real Estate

  1503 Edgewood Ln, Winnetka, IL 60093
• 

  

  /25

  Est $558,368

  Not Listed For Sale

  778 Green Bay Rd, Winnetka, IL 60093

  • 3 Beds
  • 3 Baths
  • 1,559 Sq Ft
  • Built 1968

  778 Green Bay Rd, Winnetka, IL 60093

  Last Sold Summary

  • 4 Days On Market
• 

  

  /31

  $1,195,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,680 Sq Ft

  1208 Oak St, Winnetka, IL 60093

  Nestled in the heart of Winnetka's coveted " TREE STREETS" neighborhood sits the storybook home you've been waiting for. This special home is a sun-filled Mediterranean villa with an effortless blend of timeless architecture and a fresh, coastal-inspired aesthetic throughout. The home showcases airy interiors, soft neutral tones, and a well appointed floor plan that perfectly suits today's

  Alyson Tesar @properties Christie's International Real Estate

  1208 Oak St, Winnetka, IL 60093
• 

  

  /49

  $2,350,000

  Sold Jan 09, 2026

  180 Apple Tree Rd, Winnetka, IL 60093

  • 5 Beds
  • 3.5 Baths
  • 4,800 Sq Ft
  • Built 1955

  Last Sold Summary

  • 6% Below List Price
  • $490/SF
  • 45 Days On Market

  Current Estimated Value $2,336,941

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

  180 Apple Tree Rd, Winnetka, IL 60093

Showing Results 81 - 120, Page 3 of 18