Winnetka, IL Homes

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  /44

  $3,650,000

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

  180 De Windt Rd, Winnetka, IL 60093

  Experience the best of Winnetka living on nearly an acre in one of the village's most picturesque and prestigious locations. Tucked away behind winding, tree-lined streets, this spectacular historic renovation sits proudly on nearly a full acre of beautifully landscaped grounds. Located on prestigious De Windt Road and walking distance to top-rated Crow Island Elementary, this fairytale-like

  Grace Goro Compass

  180 De Windt Rd, Winnetka, IL 60093
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  /13

  $1,950 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  894 Green Bay Rd Unit 896A-10, 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-10, Winnetka, IL 60093
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  /27

  $625,000 Sold May 02, 2025

  • 1,300 Sq Ft
  • $481/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  640 Winnetka Mews Unit 307, Winnetka, IL 60093

  Step into style and comfort with this freshly renovated 2-bedroom, 2-bath condo in one of Winnetka's best locations. This spacious unit has it all-brand-new kitchen; boasting soft close cabinets, drawers, new stainless steel appliances equipped with ABT warranty, quartz counter tops, two modern spa- like bathrooms, in-unit laundry, and an open, airy layout that just feels like home. The unit sits

  Nicholas Hansen Home One Realty

  640 Winnetka Mews Unit 307, Winnetka, IL 60093
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  /41

  Est $2,196,448 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,828 Sq Ft

  110 N Sheridan Rd, Winnetka, IL 60093

  110 N Sheridan Rd, Winnetka, IL 60093
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  /45

  $2,900,000

  • 8 Beds
  • 7 Baths
  • 7,215 Sq Ft

  1250 Westmoor Rd, Winnetka, IL 60093

  Through the pillared stone circular driveway one enters the grounds of this extraordinary English Manor Home. The grand foyer with Paradiso marble is inset with creamy travertine and offers access to the first floor rooms and opens to the elevated 1500 square foot bluestone terrace. The handsome living room with bay window overlooks the expansive 1.3 acre grounds featuring terrace and pool and

  Dinny Dwyer Compass

  1250 Westmoor Rd, Winnetka, IL 60093
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  /20

  $9,200 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  510 Ash St, Winnetka, IL 60093

  You will love this charming Winnetka home in prime east location on a coveted street two blocks from Lake Michigan. Easy walk to Greeley School, New Trier High School, Metra train, bike trails, beaches and town. Special features include large sunlit rooms, beautiful hardwood floors, a large eat-in kitchen with all stainless steel appliances and granite counters, a first floor office/ bedroom with

  Beth Groebe Coldwell Banker Realty

  510 Ash St, Winnetka, IL 60093
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  /18

  $1,500,000 Sold May 01, 2025

  • 3,000 Sq Ft
  • $500/SF
  • 18 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1886

  965 Spruce St, Winnetka, IL 60093

  In the heart of Winnetka, a home with soul. Distinguished architecture and custom craftsmanship mark this updated masterpiece in the most walkable neighborhood in our lovely village. The perfectly proportioned rooms and thoughtful layout exude the signature warmth that greets you on the heated front porch. The unique features of each of the 4 upstairs bedrooms make it tough to pick a favorite.

  Glenn Pankau Compass

  965 Spruce St, Winnetka, IL 60093
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  /34

  Est $2,312,814 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,947 Sq Ft

  1189 Asbury Ave, Winnetka, IL 60093

  1189 Asbury Ave, Winnetka, IL 60093
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  /40

  $3,599,900

  • 5 Beds
  • 7 Baths
  • 5,589 Sq Ft

  23 Indian Hill Rd, Winnetka, IL 60093

  Set on nearly an acre of lush, landscaped grounds, this timeless Cape Cod designed by architect Paul Konstant, blends classic charm with everyday comfort. The best relaxed ranch layout with luxurious primary suite on the main floor and 3 beds up. Sunlight fills the home through skylights, clerestory windows, and French doors, highlighting high-gloss finishes, oak hardwood, and travertine marble

  Jena Radnay @properties Christie's International Real Estate

  23 Indian Hill Rd, Winnetka, IL 60093
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  /57

  $1,950 per month

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

  894 Green Bay Rd, Winnetka, IL 60093

  Renovated vintage courtyard building in the heart of the Hubbard Woods district of Winnetka.

  894 Green Bay Rd, Winnetka, IL 60093
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  /2

  $1,502,000 Sold Apr 30, 2025

  • 2,737 Sq Ft
  • $549/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1903

  1050 Elm St, Winnetka, IL 60093

  Some homes have a presence-you can feel it before you even walk through the door. 1050 Elm Street, set on a beautifully landscaped corner lot, is one of those homes. Thoughtfully updated yet full of original character, it's a place that feels both timeless and effortlessly livable. A front porch welcomes you inside, where high ceilings, stained glass windows, and rich millwork set the tone. The

  Howard Meyers Compass

  1050 Elm St, Winnetka, IL 60093
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  /29

  Est $2,078,306 Not Listed For Sale

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

  1060 Spruce St, Winnetka, IL 60093

  1060 Spruce St, Winnetka, IL 60093
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  /39

  $4,500,000

  • 4 Beds
  • 7 Baths
  • 8,294 Sq Ft

  Unlisted Address

  Perfectly situated in a discreet upscale enclave east of Sheridan road. Beautifully tucked away is where you'll find this gorgeous estate on a professionally landscaped .659 acre. With exceptional quality, elegance and design throughout there are many updates that have been done over the last 3 years. Upon entering the foyer you'll see 12-14 ceilings and gorgeous marble floors. New Kitchen with

  Kim Kelley Baird & Warner

  Unlisted Address
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  /31

  $10,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,470 Sq Ft
  • House for Rent

  280 Sheridan Rd, Winnetka, IL 60093

  GREAT RENTAL OPPORTUNITY! Ideal tenant will want to rent for school year(s) and allow owner to occupy during summer; multiple year lease available. All options offered will also be considered. Close to Greeley and New Trier. Perched gracefully on a half-acre of lush, manicured land, this stately three-story home, built in 1915, exudes timeless elegance and charm. With 4,400 square feet of

  Blanche Romey @properties Christie's International Real Estate

  280 Sheridan Rd, Winnetka, IL 60093
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  /71

  $2,920,000 Sold Apr 30, 2025

  • 4,753 Sq Ft
  • $614/SF
  • 16 Days On Market

  • 4 Beds
  • 8 Baths
  • Built 2004

  1234 Westmoor Rd, Winnetka, IL 60093

  Welcome to your dream home on idyllic Westmoor Road! This exceptional custom residence blends sophistication with California flair, offering an incredibly livable space designed for easy first-floor living and gracious entertaining. Step into the sun-filled great room with a handsome fireplace, creating a warm ambiance that permeates throughout the home. The exquisite kitchen seamlessly flows

  Joanne Hudson Compass

  1234 Westmoor Rd, Winnetka, IL 60093
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  /18

  Est $1,364,760 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,817 Sq Ft

  270 Mary St, Winnetka, IL 60093

  270 Mary St, Winnetka, IL 60093
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  /40

  $2,450,000

  • 5 Beds
  • 6 Baths
  • 4,776 Sq Ft

  1065 Fisher Ln, Winnetka, IL 60093

  Architecturally stunning custom contemporary on a lush 1/2 acre private lane with lake breezes. Designed to maximize natural light and indoor-outdoor living, the home features expansive windows, skylights, and three rooftop decks. The open floor plan showcases soaring ceilings, newly refinished maple floors with mahogany trim, and natural stone accents. A beautifully renovated kitchen with a

  Karen Mason @properties Christie's International Real Estate

  1065 Fisher Ln, Winnetka, IL 60093
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  /57

  $2,395 per month

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

  894 Green Bay Rd, Winnetka, IL 60093

  Renovated vintage courtyard building in the heart of the Hubbard Woods district of Winnetka.

  894 Green Bay Rd, Winnetka, IL 60093
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  /38

  $2,475,000 Sold Apr 30, 2025

  • 4,713 Sq Ft
  • $525/SF

  • 5 Beds
  • 4.5 Baths
  • Built 1965

  345 Birch St, Winnetka, IL 60093

  Here is your rare in-town opportunity to own a super cool Lannon stone Mid Century ranch-like home with a great natural vibe & endless options as this house has been impeccably maintained & cared for. With a sanctuary oasis 1st floor primary featuring its own private patio overlooking the mature, serene landscaped backyard on a half acre lot, this special home has remarkable features: desirable

  Jena Radnay @properties Christie's International Real Estate

  345 Birch St, Winnetka, IL 60093
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  /20

  Est $811,277 Not Listed For Sale

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

  812 Oak St Unit 201, Winnetka, IL 60093

  812 Oak St Unit 201, Winnetka, IL 60093
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  /54

  $2,750,000

  • 6 Beds
  • 4.5 Baths
  • 4,251 Sq Ft

  474 Sheridan Rd, Winnetka, IL 60093

  Welcome to sophisticated living on Sheridan Road, where elegance meets comfort in the heart of East Winnetka. This exquisite 6-bedroom, 4.1-bathroom home is a true oasis, offering a sanctuary from the hustle and bustle of everyday life. Step inside to discover a gracious living room bathed in natural sunlight, featuring hardwood floors, original plaster moldings, and views of the expansive

  Carrie Healy Compass

  474 Sheridan Rd, Winnetka, IL 60093
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  /6

  $9,100 per month

  • 4 Beds
  • 3.5 Baths
  • 2,344 Sq Ft
  • House for Rent

  1443 Scott Ave, Winnetka, IL 60093

  Adorable, freshly renovated and updated, with loads of open space and light house.This is a 4 bedroom, 3.5 bath with partially finished basement home. Conveniently located at Winnetka's Hubbard Woods, where you find shopping, restaurants, parks, train station and many more. Excellent school district with great neighborhood. This house features large kitchen with pennicula, beautiful quartz

  Derek Eisenberg Continental Real Estate Group

  1443 Scott Ave, Winnetka, IL 60093
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  /82

  $1,650,000 Sold Apr 22, 2025

  • 3,377 Sq Ft
  • $489/SF
  • 33 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2001

  705 Oak St, Winnetka, IL 60093

  Location, location, location! This stunning home is ideally situated near downtown Winnetka and just minutes from the beach. Enjoy the convenience of being close to top-rated restaurants, boutique shops, transportation, and expressways-all while living in a serene and picturesque setting. From the moment you step into the grand foyer, featuring an elegant staircase, this home will captivate you.

  Christopher Paul Redfin Corporation

  705 Oak St, Winnetka, IL 60093
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  /22

  Est $501,276 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,642 Sq Ft

  630 Winnetka Mews Unit 402, Winnetka, IL 60093

  630 Winnetka Mews Unit 402, Winnetka, IL 60093
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  /71

  $4,499,900

  • 8 Beds
  • 7 Baths
  • 7,168 Sq Ft

  5 Woodley Rd, Winnetka, IL 60093

  An eternal architectural beauty set on prestigious Woodley Road, this stately, white-painted brick Colonial accented with black shutters never goes out of style. Nestled on over 1.4 acres of meticulously manicured grounds by Midwest Arbor, these 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern life. Elegance

  Jena Radnay @properties Christie's International Real Estate

  5 Woodley Rd, Winnetka, IL 60093
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  /57

  $2,395 per month

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

  894 Green Bay Rd, Winnetka, IL 60093

  Renovated vintage courtyard building in the heart of the Hubbard Woods district of Winnetka.

  894 Green Bay Rd, Winnetka, IL 60093
• 

  

  /60

  $4,975,000 Sold Apr 22, 2025

  • 11,234 Sq Ft
  • $443/SF
  • 142 Days On Market

  • 6 Beds
  • 9 Baths
  • Built 1936

  40 Woodley Rd, Winnetka, IL 60093

  One word...breathtaking! Sole ownership of this exquisite rehab & seamless expansion to ultra luxe perfection brings the essence of a French estate to life with 360 degrees of beauty from inside to out! From the moment you journey down the pea gravel driveway, you're transported to a world of extraordinary elegance & charm. Perfectly lime stained Chicago common brick sets the prominent tone

  Jena Radnay @properties Christie's International Real Estate

  40 Woodley Rd, Winnetka, IL 60093
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  /55

  Est $2,092,797 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 3,823 Sq Ft

  191 Scott Ave, Winnetka, IL 60093

  191 Scott Ave, Winnetka, IL 60093
• 

  

  /53

  $3,550,000

  • 6 Beds
  • 6.5 Baths

  681 Lincoln Ave, Winnetka, IL 60093

  Exciting opportunity to acquire a remarkable property in Winnetka! This stunning Benjamin Marshall-designed home is nestled on 2/3rds of an acre in the heart of the Village. The property boasts professional landscaping, including an oversized pool, putting green, and a 1/2 basketball court. Enjoy the expansive outdoor spaces with large patios, a cozy screened-in porch, and a balcony off the

  Annika Valdiserri @properties Christie's International Real Estate

  681 Lincoln Ave, Winnetka, IL 60093
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  /4

  $1,950 per month

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

  896 Green Bay Rd Unit A08C, Winnetka, IL 60093

  896 Green Bay Rd Unit A08C, Winnetka, IL 60093
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  /36

  $1,450,000 Sold Apr 21, 2025

  • 3,510 Sq Ft
  • $413/SF
  • 13 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1997

  838 Cherry St, Winnetka, IL 60093

  "Seller is requesting Best and Final Offers for purchase of 838 Cherry by 12:00 Noon on Sunday. February 23rd." Captivating English Country Garden home in ideal "walk-to" location to Metra, library, village shopping & dining, schools, parks, playground & beach. Ivy covered side entrance with 2 car attached garage with tool/garden prep alcove. Custom built in 1997, this one-owner home was

  Beverly Fleischman Coldwell Banker Realty

  838 Cherry St, Winnetka, IL 60093
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  /28

  Est $846,355 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,972 Sq Ft

  812 Oak St Unit 203, Winnetka, IL 60093

  812 Oak St Unit 203, Winnetka, IL 60093
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  /70

  $2,490,000

  • 6 Beds
  • 6.5 Baths
  • 5,400 Sq Ft

  747 Walden Rd, Winnetka, IL 60093

  Step into this bright and airy modern farmhouse new construction in coveted Hubbard Woods, and call it home. Situated between Hubbard Woods and Winnetka Metra stations, this charming light-filled 7 bed 6.5 bath home is situated on Walden Road, a serene tree-lined street just a 5 minute walk to the heart of the village's commercial and social center. The house boasts every detail for comfortable

  Joshua Ha EAR Real Estate, Ltd.

  747 Walden Rd, Winnetka, IL 60093
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  /28

  $2,195 per month

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

  545 Chestnut St Unit 817-206, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Renovated 1 bedroom apartment in Winnetka! Unit features hardwood floors, updated kitchen & bath, separate dining area, laundry

  545 Chestnut St Unit 817-206, Winnetka, IL 60093
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  /9

  $1,525,000 Sold Apr 18, 2025

  • 3,000 Sq Ft
  • $508/SF
  • 15 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1916

  843 Cherry St, Winnetka, IL 60093

  This exceptional residence is nestled in an enviable, close-to-everything location, offering unparalleled convenience and charm. Impeccably redesigned with European craftsmanship and architectural sophistication, this home exudes elegance from top to bottom. Upon entry, you are welcomed by a captivating vaulted three-season room, featuring floor-to-ceiling windows and a welcoming fireplace,

  James Qiu Kale Realty

  843 Cherry St, Winnetka, IL 60093
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  /41

  Est $684,255 Not Listed For Sale

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

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

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

  

  /41

  $2,995,000 Pending

  • 6 Beds
  • 5 Baths
  • 5,461 Sq Ft

  644 Oak St, Winnetka, IL 60093

  Stunning architectural gem in East Winnetka, where history meets modern sophistication. This magnificent 5+ bedroom, 3.2-bath classic, set on an expansive .4-acre lot, offers a unique blend of timeless charm and contemporary luxury overlooking the serene vistas of the iconic Village Green. Originally designed and built by the renowned architect William A. Otis for his own family, this home

  Paige Dooley Compass

  644 Oak St, Winnetka, IL 60093
• 

  /2

  $1,895 per month

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

  731 Elm St Unit 733-302, Winnetka, IL 60093

  Listing presented by Marshall Lee, licensed leasing agent with Fulton Grace. Charming 1 bedroom apartment features hardwood floors, updated kitchen and bath. Laundry in-unit. Pets welcome. Close to

  731 Elm St Unit 733-302, Winnetka, IL 60093
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  /53

  $2,750,000 Sold Apr 18, 2025

  • 5,761 Sq Ft
  • $477/SF
  • 5 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 1973

  201 Linden St, Winnetka, IL 60093

  Welcome to an unparalleled fusion of luxury and functionality in this stunning 6BD/5.2BA home on nearly a half acre (100x187) with nearly 6000 sq ft of living space above grade seamlessly combining exceptional design along with a comprehensive, full gut renovation in 2021. The unique and flexible floor plan offers a fabulous option for one floor living with an incredible first floor primary suite

  Paige Dooley Compass

  201 Linden St, Winnetka, IL 60093
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  /52

  Est $3,919,086 Not Listed For Sale

  • 6 Beds
  • 9 Baths
  • 10,753 Sq Ft

  102 Longmeadow Rd, Winnetka, IL 60093

  102 Longmeadow Rd, Winnetka, IL 60093

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