Winnetka Homes

• 

  

  

  /44

  $3,750,000 Sold Aug 01, 2025

  • 5,735 Sq Ft
  • $654/SF
  • 2 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1930

  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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  /50

  Est $2,237,930 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,311 Sq Ft

  1162 Scott Ave, Winnetka, IL 60093

  1162 Scott Ave, Winnetka, IL 60093
• 

  

  

  /50

  $1,400,000

  • 5 Beds
  • 3.5 Baths
  • 2,806 Sq Ft

  325 Ridge Ave, Winnetka, IL 60093

  There are houses, and then there are homes...the kind that hold stories, gather laughter, and offer a quiet exhale at the end of the day. This timeless colonial has been just that, and now it's ready to welcome yours. Enter the front door through the vestibule into a gracious foyer that sets the tone for what's ahead. The formal living room is adorned with molding, offers a fireplace as well as

  Virginia Trux @properties Christie's International Real Estate

  325 Ridge Ave, Winnetka, IL 60093
• 

  

  

  /35

  $1,100,000 Sold Aug 01, 2025

  • 2,534 Sq Ft
  • $434/SF
  • 19 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1910

  886 Willow Rd, Winnetka, IL 60093

  Recently renovated home (2021) close to everything! This four bedroom plus an office and three and half bathroom home has been thoughtfully rehabbed with beautiful finishes. The gracious open floor plan allows for easy living and entertaining with ample natural light flooding in the windows. The white oak hardwood floors are found throughout the home. Walk into your large living room, which opens

  Carly Jones Engel & Voelkers Chicago North Shore

  886 Willow Rd, Winnetka, IL 60093
• 

  

  

  /24

  Est $1,663,624 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,538 Sq Ft

  740 Humboldt Ave, Winnetka, IL 60093

  740 Humboldt Ave, Winnetka, IL 60093
• 

  

  /46

  $1,789,000 Pending

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

  1503 Edgewood Ln, Winnetka, IL 60093

  Better Than New - A Stunning Custom Renovation with Timeless Charm Welcome to this spectacular, fully reimagined home where high-end design meets everyday comfort. A complete gut renovation plus a spacious new addition have transformed this residence into a light-filled, luxurious retreat with soaring ceilings, expansive new windows, and thoughtfully curated custom finishes throughout. Step

  Sarah Lyons @properties Christie's International Real Estate

  1503 Edgewood Ln, Winnetka, IL 60093
• 

  

  /21

  $640,000 Sold Jul 31, 2025

  • 1,976 Sq Ft
  • $324/SF
  • 3 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1973

  650 Winnetka Mews Unit 311, Winnetka, IL 60093

  Rarely available, this 3-bedroom, 3-bath residence in sought-after Winnetka Mews offers gracious living in the heart of town. A welcoming foyer leads to an expansive, sunlit living room with treetop views, a classic wood-burning fireplace, and seamless flow into the elegant dining room, with sliding doors that open to a private balcony. Set off the living room, the office/den offers extra living

  Mary Grant @properties Christie's International Real Estate

  650 Winnetka Mews Unit 311, Winnetka, IL 60093
• 

  

  /36

  Est $1,774,007 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,178 Sq Ft

  385 Provident Ave, Winnetka, IL 60093

  385 Provident Ave, Winnetka, IL 60093
• 

  

  /53

  $2,595,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,904 Sq Ft

  755 Lincoln Ave, Winnetka, IL 60093

  The iconic front porch has you at hello...welcoming you to this exceptionally updated classic on an oversized (100' wide) professionally landscaped yard on one of East Winnetka's most desirable streets! Masterful renovations have enhanced the home's historic charm with an air of elevated contemporary aesthetic, preserving the timeless elegance while seamlessly incorporating updates to exceed

  Paige Dooley Compass

  755 Lincoln Ave, Winnetka, IL 60093
• 

  /2

  $1,375,000 Sold Jul 31, 2025

  • 2,170 Sq Ft
  • $634/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  1101 Oak St, Winnetka, IL 60093

  Welcome to 1101 Oak Street - a beautifully updated home in the heart of the tree streets of Winnetka, offering the perfect blend of comfort, functionality, and fun. With 4 bedrooms, 2.1 baths, and an attached 2-car garage, this home is designed for easy everyday living and effortless entertaining. Step into a light-filled living room with gorgeous hardwood floors, seamlessly flowing into a

  David Chung Compass

  1101 Oak St, Winnetka, IL 60093
• 

  

  /19

  Est $5,098,227 Not Listed For Sale

  • 6 Beds
  • 8 Baths
  • 6,650 Sq Ft

  41 Indian Hill Rd, Winnetka, IL 60093

  41 Indian Hill Rd, Winnetka, IL 60093
• 

  

  /39

  $4,250,000 Pending

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

  977 Sheridan Rd, Winnetka, IL 60093

  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

  977 Sheridan Rd, Winnetka, IL 60093
• 

  /2

  $935,000 Sold Jul 30, 2025

  • 2,264 Sq Ft
  • $413/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1925

  1442 Asbury Ave, Winnetka, IL 60093

  Located in one of Winnetka's most beloved neighborhoods, this classic Tudor offers timeless charm and endless potential. The spacious living room, featuring arched bookcases and fireplace, provides a cozy and inviting gathering space. An entertainment-sized dining room with built-ins adds both charm and functionality, The kitchen iwith table space, ample counter seating, and an adjacent family

  Sherry Molitor Compass

  1442 Asbury Ave, Winnetka, IL 60093
• 

  

  /39

  Est $1,726,234 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,111 Sq Ft

  1271 Asbury Ave, Winnetka, IL 60093

  1271 Asbury Ave, Winnetka, IL 60093
• 

  

  /46

  $2,900,000 Pending

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

  1250 Westmoor Rd, Winnetka, IL 60093

  Upon entering the grounds of this remarkable English Manor Home through the grand stone circular driveway adorned with pillars, you're greeted by an impressive foyer featuring Paradiso marble flooring inlaid with creamy travertine. This area provides access to the first-floor rooms and leads to a 1,500-square-foot elevated bluestone terrace. The elegant living room, with its bay window, offers

  Dinny Dwyer Compass

  1250 Westmoor Rd, Winnetka, IL 60093
• 

  

  /40

  $2,180,000 Sold Jul 30, 2025

  • 4,800 Sq Ft
  • $454/SF
  • 26 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 2004

  824 Humboldt Ave, Winnetka, IL 60093

  Tucked away on a serene cul-de-sac just steps from downtown Winnetka and Lake Michigan, this striking contemporary residence offers refined living in one of East Winnetka's most coveted locations. Designed by Gary Lee Partners and award-winning principal architect Sharlene Young, the home is a masterful expression of modern elegance, where innovative materials and meticulous craftsmanship create

  Michael Canzolino Chicago Properties Firm

  824 Humboldt Ave, Winnetka, IL 60093
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  /37

  Est $1,626,433 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 2,284 Sq Ft

  807 Cherry St, Winnetka, IL 60093

  807 Cherry St, Winnetka, IL 60093
• 

  

  /28

  $849,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,187 Sq Ft

  640 Winnetka Mews Unit 108, Winnetka, IL 60093

  Rarely available, beautiful 3bed/3bath plus 3 balconies "Maisonette" unit on first floor of the highly desired Winnetka Mews! The gracious foyer welcomes you into the open, sunny living room with a handsome fireplace (electric) and multiple windows overlooking wonderful outdoor views. The separate dining room conveniently connects through to the spacious bright kitchen and accesses the back

  Paige Dooley Compass

  640 Winnetka Mews Unit 108, Winnetka, IL 60093
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  /45

  $2,201,894 Sold Jul 29, 2025

  • 5,000 Sq Ft
  • $440/SF
  • 7 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1894

  550 Oak St, Winnetka, IL 60093

  Opportunity to own and enhance a once-in-a-generation architecturally rich East Winnetka home built in 1894 and set on a beautifully landscaped .42-acre corner lot just steps from town, train, schools, Lake Michigan beaches and the Village Green. Bring your contractor with you to see this solidly built 5000 plus square foot, 5+ bedrooms, 3.2 baths vintage beauty that is surrounded by an iconic

  Paige Dooley Compass

  550 Oak St, Winnetka, IL 60093
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  /30

  Est $599,606 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,870 Sq Ft

  711 Oak St Unit 210, Winnetka, IL 60093

  711 Oak St Unit 210, Winnetka, IL 60093
• 

  

  /101

  $5,995,000 Pending

  • 5 Beds
  • 8 Baths
  • 13,482 Sq Ft

  624 Pine Ln, Winnetka, IL 60093

  Welcome to this stunning custom home designed by Morgante Wilson, with thoughtful input from discerning owners. This once in a lifetime home is nestled on a picturesque 0.86-acre lot on private Pine Lane near schools, town and train. This thoughtfully designed home is perfect for all ages, blending creativity and style throughout. The inviting entrance hall sets the tone as you walk in, leading

  Joanne Hudson Compass

  624 Pine Ln, Winnetka, IL 60093
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  /86

  $3,175,000 Sold Jul 29, 2025

  • 5,651 Sq Ft
  • $562/SF
  • 3 Days On Market

  • 5 Beds
  • 9 Baths
  • Built 2004

  1575 Hickory Ln, Winnetka, IL 60093

  Welcome to this absolutely fabulous home nestled on a serene half-acre lot on picturesque Hickory Lane. Recently renovated, this residence offers three thoughtfully designed floors of luxurious living space, perfect for both relaxation and entertaining. As you enter, you're greeted by an impressive foyer that leads to the inviting living room, complete with a classic fireplace. The elegant dining

  Joanne Hudson Compass

  1575 Hickory Ln, Winnetka, IL 60093
• 

  

  /38

  Est $2,817,672 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 5,619 Sq Ft

  1024 Westmoor Rd, Winnetka, IL 60093

  1024 Westmoor Rd, Winnetka, IL 60093
• 

  

  /41

  $989,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,704 Sq Ft

  674 Foxdale Ave, Winnetka, IL 60093

  Final and best offer by 11am Saturday, June 21st. No escalation clause. Amazing in-town location for this handsome 4 bedroom, three bath home! Beautiful living room with fireplace...hardwood floors, plantation shutters and wall of windows. Separate formal dining room for family dinner or holiday celebrations. Open kitchen with quartz countertops, stainless steel appliances and plenty of room

  Carol Munro Jameson Sotheby's International Realty

  674 Foxdale Ave, Winnetka, IL 60093
• 

  

  /25

  $979,000 Sold Jul 25, 2025

  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  380 Green Bay Rd Unit 4D, Winnetka, IL 60093

  Coveted Hedge Row Penthouse, HARD TO FIND ONE FLOOR living in the Heart of Winnetka! This Northwest *End unit - is on the market for the first time! This is one of only a few on the top floor that are on the *BACK* side of the building - so you don't face Green Bat Road and the train tracks - and no one is above you - so it is quiet!! This 2 bedroom, 2 bath + den condo is spacious and neutral.

  Megan Mawicke @properties Christie's International Real Estate

  380 Green Bay Rd Unit 4D, Winnetka, IL 60093
• 

  

  /48

  Est $2,963,742 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 4,600 Sq Ft

  1016 Westmoor Rd, Winnetka, IL 60093

  1016 Westmoor Rd, Winnetka, IL 60093
• 

  

  /39

  $1,860,000 Sold Jul 25, 2025

  • 3,500 Sq Ft
  • $531/SF
  • 32 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2004

  384 Provident Ave, Winnetka, IL 60093

  Sophisticated Living in the Heart of Winnetka Step into timeless elegance with this meticulously crafted custom home, ideally located on a picturesque tree-lined street in one of Winnetka's most desirable neighborhoods. Built in 2005, 384 Provident Avenue offers nearly 3,500 square feet of thoughtfully designed living space with quality craftsmanship, architectural character, and exceptional

  Scott Fishman Worth Clark Realty

  384 Provident Ave, Winnetka, IL 60093
• 

  

  /42

  Est $1,614,125 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,354 Sq Ft

  1041 Elm St, Winnetka, IL 60093

  1041 Elm St, Winnetka, IL 60093
• 

  

  /28

  $1,525,000 Sold Jul 24, 2025

  • 3,440 Sq Ft
  • $443/SF
  • 3 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1924

  720 Willow Rd, Winnetka, IL 60093

  Introducing a stunning blend of timeless sophistication and modern functionality in the heart of Winnetka. This sun-drenched 5-bedroom, 4.1-bathroom home spans 3,440 square feet of thoughtfully designed living space, perfect for today's lifestyle. Step inside to discover hardwood floors, a striking stone fireplace, and Marvin windows that flood the home with natural light. The chef's kitchen is a

  Marlene Rubenstein Baird & Warner

  720 Willow Rd, Winnetka, IL 60093
• 

  

  /20

  Est $633,046 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft

  711 Oak St Unit 401, Winnetka, IL 60093

  711 Oak St Unit 401, Winnetka, IL 60093
• 

  

  /51

  $9,499,900 Sold Jul 22, 2025

  • 9,723 Sq Ft
  • $977/SF
  • 29 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 2021

  139 Sheridan Rd, Winnetka, IL 60093

  Summer is right around the corner, and 139 Sheridan is the ultimate lakefront escape. Built into the bluff and just steps to the water, this turnkey Morgante Wilson custom home is designed for effortless lake living. One of the last new construction homes allowed to build into the bluff, it offers a front-row seat to beach days, boat rides, and unforgettable summer memories. Incredible panoramic

  Jena Radnay @properties Christie's International Real Estate

  139 Sheridan Rd, Winnetka, IL 60093
• 

  

  /54

  Est $1,570,516 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,949 Sq Ft

  1168 Hamptondale Ave, Winnetka, IL 60093

  1168 Hamptondale Ave, Winnetka, IL 60093
• 

  

  /3

  $1,190,000 Sold Jul 22, 2025

  • 3,100 Sq Ft
  • $384/SF
  • 2 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2021

  880 Willow Rd, Winnetka, IL 60093

  Rare opportunity in today's market to find an almost-new, move-in-ready home offering comfort, convenience and a contemporary vibe. This spacious 5-bedroom, 3.5-bath home features a bright, open layout with natural oak floors and a designer kitchen outfitted with a 9-foot island, quartz Calacatta Laza countertops, and premium KitchenAid stainless steel appliances. The great room off of the

  Karen Arenson Engel & Voelkers Chicago North Shore

  880 Willow Rd, Winnetka, IL 60093
• 

  

  /40

  Est $3,008,744 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 6,689 Sq Ft

  566 Willow Rd, Winnetka, IL 60093

  566 Willow Rd, Winnetka, IL 60093
• 

  

  /50

  $1,725,000 Sold Jul 21, 2025

  • 4,381 Sq Ft
  • $394/SF
  • 59 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1966

  770 Prospect Ave, Winnetka, IL 60093

  Exceptional opportunity on one of the most coveted locations in prime East Winnetka! Solidly-built and sunny 5+ bed , 4.1 bath home with unique floor plan and tons of charm - walk to beach, town, train and more. Beautiful boxwood garden with bluestone pathway and front patio welcome you home! The fresh kitchen with breakfast area features new quartz countertops, and has potential to be opened to

  Paige Dooley Compass

  770 Prospect Ave, Winnetka, IL 60093
• 

  

  /18

  Est $332,963 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 787 Sq Ft

  555 Hill Terrace Unit 207, Winnetka, IL 60093

  555 Hill Terrace Unit 207, Winnetka, IL 60093
• 

  

  /44

  $1,400,000 Sold Jul 21, 2025

  • 3,611 Sq Ft
  • $388/SF
  • 2 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1939

  1166 Cherry St, Winnetka, IL 60093

  Longtime homeowners have meticulously maintained (and added onto) this exceptionally large 3600 square foot home. It's so much bigger than it looks! Get ready to have your homebuyer wish list boxes checked. Fabulous Winnetka location on a favorite tree-lined street, just 1-2 blocks from all schools, Skokie Playfield Park District facilities, and under a mile to town, Metra, shopping, and dining.

  Chris Veech @properties Christie's International Real Estate

  1166 Cherry St, Winnetka, IL 60093
• 

  

  /22

  Est $1,051,935 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft

  130 Woodland Ave, Winnetka, IL 60093

  130 Woodland Ave, Winnetka, IL 60093
• 

  

  /70

  $2,360,000 Sold Jul 18, 2025

  • 4,600 Sq Ft
  • $513/SF
  • 10 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2023

  385 Rosewood Ave, Winnetka, IL 60093

  Discover an exquisite blend of architectural brilliance and top-tier craftsmanship in this stunning home, newly constructed in 2023 in the heart of town. This home is adorned with fabulous upgrades including premium appliances, hardwood flooring throughout, extensive custom millwork (coffered ceilings, paneling, moldings, and wainscoting), 10 foot ceilings, advanced technology for seamless

  Joanne Hudson Compass

  385 Rosewood Ave, Winnetka, IL 60093
• 

  

  /38

  Est $1,203,864 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,513 Sq Ft

  135 Lake St, Glencoe, IL 60022

  135 Lake St, Glencoe, IL 60022

Showing Results 81 - 120, Page 3 of 18