Winnetka, IL Homes

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  /51

  $2,850,000 Sold Feb 19, 2025

  • 4,203 Sq Ft
  • $678/SF
  • 0 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1937

  484 Cedar St, Winnetka, IL 60093

  Exceptional East Winnetka Masterpiece meticulously renovated to combine timeless charm with modern luxury situated in a A+ East Winnetka location with Village Green as your welcoming neighbor! A Benjamin Marshall classic architectural gem with 6 beds/ 4.2 baths has been completely transformed into a modern showpiece that is better than new construction as this delivers the charm & beauty with

  Jena Radnay @properties Christie's International Real Estate

  484 Cedar St, Winnetka, IL 60093
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  /37

  Est $1,448,769 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
• 

  

  

  /40

  $1,499,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,708 Sq Ft

  815 Rosewood Ave, Winnetka, IL 60093

  Situated in the most charming neighborhood between Winnetka and Hubbard Woods, this sunny, meticulously maintained 4+ bedroom, 3 and a half bath home is the perfect combination of vintage character and modern decor: full of classic architectural details, tall ceilings, lovely millwork and hardwood floors. Nestled on a generous double-wide lot with gorgeous green vistas in a serene setting, the

  Paige Dooley Compass

  815 Rosewood Ave, Winnetka, IL 60093
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  /54

  $1,150,000 Sold Feb 14, 2025

  • 3,040 Sq Ft
  • $378/SF
  • 4 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1923

  351 Ridge Ave, Winnetka, IL 60093

  Step into this exquisite 4-bedroom, 4.1-bathroom gem, nestled in a coveted in-town location just moments from the train, top-rated schools, and lush parks. This elegant home boasts a circular floor plan awash with natural light, featuring a sophisticated living room complete with a wood-burning fireplace, expansive windows, and exquisite built-ins. The dining room offers a refined space for

  Mike LeFevere Compass

  351 Ridge Ave, Winnetka, IL 60093
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  /32

  Est $1,368,523 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,795 Sq Ft

  35 Brier St, Winnetka, IL 60093

  35 Brier St, Winnetka, IL 60093
• 

  

  /18

  $1,495,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,466 Sq Ft

  1215 Hill Rd, Winnetka, IL 60093

  This wonderful and hard-to-find 3-bedroom, 2-bathroom RANCH home sits on an expansive 110 x 200 lot. As you enter, you'll be greeted by the warmth of a sun-filled living room featuring a large bay window, built-in bookshelves, a beautiful fireplace, and a large wet bar. Adjacent to the living room is the family room, with walls of windows, a hidden dry bar, and ample closet space. The bright

  Shelley Shelly @properties Christie's International Real Estate

  1215 Hill Rd, Winnetka, IL 60093
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  /2

  $565,000 Sold Feb 14, 2025

  • 3,200 Sq Ft
  • $177/SF
  • 126 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1963

  1143 Willow Rd, Winnetka, IL 60093

  A great opportunity for the visionary! The existing home is a large build from 1963 and has some MCM touches! Perfect opportunity for a gut Rehab! Very desirable location across from Historic CROW ISLAND WOODS and Crow Island School! Easy walk to wonderful Downtown Winnetka with Shopping, Dining and so much more! Property is being offered As Is and Shown.

  Kathleen Peters Coldwell Banker Realty

  1143 Willow Rd, Winnetka, IL 60093
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  /27

  Est $2,108,137 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,367 Sq Ft

  1078 Spruce St, Winnetka, IL 60093

  1078 Spruce St, Winnetka, IL 60093
• 

  

  /13

  $575,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft

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

  Enjoy maintenance free living in this charming two bedroom, two bathroom home in an elevator building in desirable Winnetka. The unit has eastern exposure, filling the space with natural light. Featuring hardwood floors throughout, with custom drapery and stunning designer hardwood sliding door, this residence combines comfort and luxury. The primary bedroom has abundant space with a large

  Marjorie Richter Baird & Warner

  720 Green Bay Rd Unit 2E, Winnetka, IL 60093
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  /16

  $605,000 Sold Feb 11, 2025

  • 1,545 Sq Ft
  • $392/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  360 Green Bay Rd Unit 4C, Winnetka, IL 60093

  Ideal Winnetka location that is close to all in this coveted Hedge Row condo! Top floor unit with skylights and sunny western exposure! Welcoming entrance hall leads to spacious and attractive living room/dining room with newer wood floors and gas fireplace. This unit boasts the ever important outdoor space where you can sip your morning coffee or enjoy the evening sunset from your private

  Mary Sehlhorst Jameson Sotheby's International Realty

  360 Green Bay Rd Unit 4C, Winnetka, IL 60093
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  /30

  Est $586,141 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
• 

  

  /28

  $1,795,000 Pending

  • 4 Beds
  • 4.5 Baths

  1132 Oak St, Winnetka, IL 60093

  Nestled in sought after in town location. The front porch welcomes you as you enter the home! Beautiful LR and DR with hardwood floors, detailed custom molding and window treatments. Light and airy kitchen, with quartz counters, stainless steel appliances, breakfast bar, table space, planning desk, walk in pantry. Family room with hardwood floors, fireplace. Fabulous mud room with built-in

  Kathleen Doron Coldwell Banker Realty

  1132 Oak St, Winnetka, IL 60093
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  /32

  $1,311,375 Sold Feb 03, 2025

  • 3,746 Sq Ft
  • $350/SF
  • 1 Day On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1926

  228 Sheridan Rd, Winnetka, IL 60093

  ***BROKER OPEN CANCELLED FOR TUESDAY 11/19!!!*** 228 Sheridan Road sits at the center of a unique cluster of iconic Winnetka homes reminiscent of Italian Renaissance Revival architectural style. This residence makes a visual statement with ornamental stonework around the Palladian-like windows that open to the lawn and a stone balustrade on the balcony that evoke a bygone era. Its front yard is

  Nancy Nugent Jameson Sotheby's Intl Realty

  228 Sheridan Rd, Winnetka, IL 60093
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  /38

  Est $2,687,966 Not Listed For Sale

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

  1024 Westmoor Rd, Winnetka, IL 60093

  1024 Westmoor Rd, Winnetka, IL 60093
• 

  

  /59

  $3,199,900 Pending

  • 6 Beds
  • 6 Baths
  • 9,160 Sq Ft

  346 Sheridan Rd, Winnetka, IL 60093

  This is the house that inspires so many to copy with its magical presence...a white-framed architectural beauty accented by the perfect blue hue Farrow & Ball painted front door, inviting you into a space that is both refined & rehabbed to perfection making it the best of both worlds. Step inside to discover a "preppy chic dream" vibe with a winning circular floor plan that has been tweaked to

  Jena Radnay @properties Christie's International Real Estate

  346 Sheridan Rd, Winnetka, IL 60093
• 

  

  /22

  $950,000 Sold Jan 31, 2025

  • 2,756 Sq Ft
  • $345/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1930

  1260 Ash St, Winnetka, IL 60093

  Storybook Winnetka Tudor on oversized lot in the tree streets! Wonderfully refreshed home with well proportioned rooms and a great functional floorplan. First floor includes an airy living room with high beamed ceiling, stone wbfp, built-in shelving and light from windows on 3 sides. Separate formal dining room overlooks large fenced yard. Newer kitchen with granite countertops, stainless

  Roberta Brennan @properties Christie's International Real Estate

  1260 Ash St, Winnetka, IL 60093
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  /42

  Est $1,511,999 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
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  /61

  $10,299,900 Pending

  • 5 Beds
  • 8 Baths
  • 8,086 Sq Ft

  381 Sheridan Rd, Winnetka, IL 60093

  Extremely RARE opportunity to own this premier in-town "Sheridan Road-to Shore" dreamy lakefront showstopper on the best lakefront block nestled between the most posh North Shore estates! Trend Construction hit it out of the park with this new phenomenal walk-out entertainment galore lower level with a low voltage Control 4 system to run the house from anywhere in the world. Luxe designer touches

  Jena Radnay @properties Christie's International Real Estate

  381 Sheridan Rd, Winnetka, IL 60093
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  /19

  $684,500 Sold Jan 31, 2025

  • 1,995 Sq Ft
  • $343/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  711 Oak St Unit 303, Winnetka, IL 60093

  Recently remodeled and spacious - this 3rd floor (nearly 2,000 sq ft) corner unit is in the heart of downtown Winnetka and offers abundant versatile space combined with quality improvements. As you enter, there is a generous foyer leading to the large L shaped living room and dining room, which is adjacent to the newly renovated eat-in kitchen. The largest balcony in the complex (30') spans the

  Meredith Schreiber @properties Christie's International Real Estate

  711 Oak St Unit 303, Winnetka, IL 60093
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  /31

  Est $1,246,976 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,286 Sq Ft

  879 Oak St, Winnetka, IL 60093

  879 Oak St, Winnetka, IL 60093
• 

  

  /86

  $3,195,000 Pending

  • 5 Beds
  • 9 Baths

  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
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  /15

  $215,000 Sold Jan 30, 2025

  • 500 Sq Ft
  • $430/SF
  • 67 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1928

  561 Hill Terrace Unit 310, Winnetka, IL 60093

  Charming one bedroom, top-floor condo with courtyard entrance in the vintage Dickens-esque Chimneys complex. Cheerful & bright unit has a proper 6' x 6' entry foyer, newer, sky-lit Kitchen with White Shaker Cabinets, Quartz Counters & Stainless Appliances including gas range, microwave, dishwasher, fridge/freezer. Windows facing East, West & South. Good-sized primary bedroom (10' x 14'). Spacious

  Michael Mitchell @properties Christie's International Real Estate

  561 Hill Terrace Unit 310, Winnetka, IL 60093
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  /20

  Est $567,803 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
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  /71

  $4,199,900 Pending

  • 5 Beds
  • 6.5 Baths
  • 9,350 Sq Ft

  865 Gordon Terrace, Winnetka, IL 60093

  Discover the pinnacle of custom design with this stunning Nantucket-inspired Adamczyk home, exuding timeless elegance with a modern and transitional twist. Drawing inspiration from the grand estates of Maine, this 9,000+ sq. ft. masterpiece harmoniously blends classic Winnetka charm with unexpected contemporary touches. Behind the striking light blue front door, step into an open reception foyer

  Jena Radnay @properties Christie's International Real Estate

  865 Gordon Terrace, Winnetka, IL 60093
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  /5

  $1,175,000 Sold Jan 21, 2025

  • Land

  • 2 Days On Market

  945 Pine Tree Ln, Winnetka, IL 60093

  Incredible super deep lot on a beautiful street full of new construction houses. Land is on a cul de sac and backs to a large park. Lot is 82.3 x 321.7. It's the perfect place to build your dream home!!!!!

  Elise Dayan @properties Christie's International Real Estate

  945 Pine Tree Ln, Winnetka, IL 60093
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  /38

  Est $1,521,781 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,603 Sq Ft

  149 Glenwood Ave, Winnetka, IL 60093

  149 Glenwood Ave, Winnetka, IL 60093
• 

  

  /33

  $1,199,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,029 Sq Ft

  1413 Tower Rd, Winnetka, IL 60093

  California Cool meets classic Tudor-style architecture in this effortlessly stylish home. Nestled in Hubbard Woods, this home radiates retro vibes, creating the perfect fusion of old-world charm and laid-back West Coast living. Step inside to discover a spacious, sunlit interior where graceful archways are paired with mid-century modern accents. The living room features a dramatic retro

  Cricket King @properties Christie's International Real Estate

  1413 Tower Rd, Winnetka, IL 60093
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  /44

  $2,050,000 Sold Jan 17, 2025

  • 4,176 Sq Ft
  • $491/SF
  • 27 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2003

  1432 Asbury Ave, Winnetka, IL 60093

  Better than brand-new construction and located on one of the most iconic streets in Hubbard Woods, 1432 Asbury Ave is a rare opportunity you won't want to miss. Recently renovated to blend the latest design trends with timeless elegance, this 5-bedroom, 4.5-bathroom home masterfully combines sophistication and comfort. Originally built by renowned builder George Adamcyk in 2003, the home features

  Bonnie Tripton @properties Christie's International Real Estate

  1432 Asbury Ave, Winnetka, IL 60093
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  /40

  Est $2,914,158 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
• 

  

  /35

  $1,100,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,534 Sq Ft

  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
• 

  

  /46

  $2,300,000 Sold Jan 16, 2025

  • 4,438 Sq Ft
  • $518/SF
  • 0 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1903

  475 Cedar St, Winnetka, IL 60093

  Experience the perfect blend of modern luxury and timeless elegance in this fully renovated beauty, in the most perfect location in the heart of East Winnetka. The stunning redesign has transformed this home from ordinary to extraordinary offering four levels of expertly designed living space and luxurious finishes at every turn-no expense has been spared. As you step through the front door,

  Melissa Mastros Compass

  475 Cedar St, Winnetka, IL 60093
• 

  

  /18

  Est $311,749 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
• 

  

  /63

  $11,999,900 Pending

  • 7 Beds
  • 8 Baths
  • 15,784 Sq Ft

  765 Sheridan Rd, Winnetka, IL 60093

  Special opportunity awaits with this impeccably maintained sole owner in-town premier Winnetka 1.3 acre lakefront estate. Truly the "ultimate lake oasis" as this house can never be built the same way with 4 full floors of luxury living space, a boutique level pool & spa on the waters edge overlooking the huge 100 ft wide sandy beach, fab entertainment walk out lower level to tiered patios,

  Jena Radnay @properties Christie's International Real Estate

  765 Sheridan Rd, Winnetka, IL 60093
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  /2

  $5,500,000 Sold Jan 15, 2025

  • 9,126 Sq Ft
  • $603/SF
  • 5 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1921

  671 Lincoln Ave, Winnetka, IL 60093

  A legendary holiday dream home, reimagined for modern-day luxury: The stately brick Georgian residence of "Home Alone" fame brings forward a rare opportunity to own one of the most iconic movie residences in American pop culture. Nestled on a picturesque, tree-lined street in the heart of east Winnetka and elegantly poised behind a wrought-iron gate, the property epitomizes classic Chicago

  Dawn McKenna Coldwell Banker Realty

  671 Lincoln Ave, Winnetka, IL 60093
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  /41

  Est $2,711,602 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,352 Sq Ft

  594 Willow Rd, Winnetka, IL 60093

  594 Willow Rd, Winnetka, IL 60093
• 

  

  /22

  $995,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  812 Oak St Unit 200, Winnetka, IL 60093

  If you've been looking for single floor living in the heart of Winnetka, you found it! The unbeatable location is within walking distance of the best restaurants, shops, the train, and more. This 3-bed 2.5-bath condo in a highly sought-after boutique elevator building has over 2300 square feet so you can really spread out. After entering through a gracious foyer you are ushered into this lovely

  Cricket King @properties Christie's International Real Estate

  812 Oak St Unit 200, Winnetka, IL 60093
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  /36

  $1,495,000 Sold Jan 09, 2025

  • 3,267 Sq Ft
  • $458/SF
  • 3 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1903

  326 Ridge Ave, Winnetka, IL 60093

  Welcome to 326 Ridge Avenue, an exquisite home where character and charm blend seamlessly with opportunities to customize and expand. Nestled on a lush .36-acre lot (85' x 187') in a premier, in-town location, this timeless property features a 4-bedroom, 2.2-bath main house and a rare, two-story coach house. Think high ceilings, marble fireplace, elegant built-ins, crown molding, and sun-drenched

  Susan Sullivan @properties Christie's International Real Estate

  326 Ridge Ave, Winnetka, IL 60093
• 

  

  /22

  Est $832,677 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
• 

  

  /44

  $5,250,000 Pending

  • 6 Beds
  • 8 Baths
  • 8,025 Sq Ft

  66 Fox Ln, Winnetka, IL 60093

  Deck the halls with boughs of holly at this magical English manor estate nestled down one of Winnetka's most cherished private lanes close to it all! Decorated in full holiday cheer, this is the home you want to come home to. When an estate can illustrate its own story without words, then you know you have discovered something truly unique. This English manor masterpiece by renowned Jazz Age

  Jena Radnay @properties Christie's International Real Estate

  66 Fox Ln, Winnetka, IL 60093
• 

  

  /44

  $3,625,000 Sold Jan 09, 2025

  • 3,792 Sq Ft
  • $956/SF
  • 12 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1961

  1066 Mount Pleasant Rd, Winnetka, IL 60093

  Completely renovated 5+bed/5.1 bath Colonial done by premier North Shore builder, Scott Lyon, renowned architect, Paul Konstant and designed by luxury interior designer, Alexandra Kaehler. Move right into this bright, warm and classically done home with an ideal floorplan. 5 bedrooms and 3 full bathrooms on second level plus studio above the garage has a separate entrance and features split HVAC

  Marlene Rubenstein Baird & Warner

  1066 Mount Pleasant Rd, Winnetka, IL 60093

Showing Results 121 - 160, Page 4 of 18