Recently Sold Winnetka Homes

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  /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
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  /26

  $1,190,000 Sold Jul 17, 2025

  • 2,646 Sq Ft
  • $450/SF
  • 96 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1917

  812 Rosewood Ave, Winnetka, IL 60093

  Lovely classic 4 square home on stellar street in walk-to town/Hubbard Woods location! Generous living room with wood-burning fireplace and built-in bookcases. Open to the sunroom, featuring three sides of windows. Formal dining room with 2 custom China cabinets. First floor den/family room. Separate, sunny kitchen with wood cabinets and stainless-steel appliances. Wonderful vintage details

  Jackie Mack Jameson Sotheby's International Realty

  812 Rosewood Ave, Winnetka, IL 60093
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  /44

  $1,300,000 Sold Jul 15, 2025

  • 1,488 Sq Ft
  • $874/SF
  • 4 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1913

  310 Fairview Ave, Winnetka, IL 60093

  Effortlessly sophisticated and meticulously updated, this East Winnetka residence merges timeless character with contemporary refinement just moments from the lake, schools, Metra and village. A marble-floored foyer sets the tone and introduces a layout that flows seamlessly from formal to casual living spaces. The living room boasts hardwood flooring, a wood-burning fireplace with brick surround

  Connie Dornan @properties Christie's International Real Estate

  310 Fairview Ave, Winnetka, IL 60093
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  /45

  $1,075,000 Sold Jul 15, 2025

  • 2,600 Sq Ft
  • $413/SF
  • 2 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1933

  1487 Tower Rd, Winnetka, IL 60093

  Once upon a time, in the picturesque village of Winnetka, a charming storybook home was crafted, now awaiting its next fortunate owner. This delightful cottage boasts enchanting details: arched & painted doorways reminiscent of a fairy tale entrance, and a grand, carved wood double staircase that gracefully connects the home's levels. The original sconces add a warm glow to the ambiance, with a

  Katie Hauser Compass

  1487 Tower Rd, Winnetka, IL 60093
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  /46

  $2,630,000 Sold Jul 15, 2025

  • 5,026 Sq Ft
  • $523/SF
  • 10 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2009

  953 Spruce St, Winnetka, IL 60093

  The one you've been waiting for-this Nantucket-style stunner checks every box and then some. Welcome to 953 Spruce Street, a picture-perfect, custom-built home by Orchard Glen Homes, nestled in the heart of Winnetka. Just steps from the train, town, restaurants, parks, and top-rated schools, this newer construction (2009) gem combines timeless design with thoughtful updates and everyday

  Bonnie Tripton @properties Christie's International Real Estate

  953 Spruce St, Winnetka, IL 60093
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  /42

  $1,725,000 Sold Jul 14, 2025

  • 3,560 Sq Ft
  • $485/SF
  • 13 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1954

  312 Rosewood Ave, Winnetka, IL 60093

  Welcome to 312 Rosewood Avenue, a very special home in a very special location, with quick closing available. Move in this summer and enjoy sunny days and starry nights in the private backyard with oversized patio, pergola and gorgeous perennial gardens. This home shows pride of ownership at every turn, as the longtime owners updated extensively and the current owners have made even more

  Susan Sullivan @properties Christie's International Real Estate

  312 Rosewood Ave, Winnetka, IL 60093
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  /52

  $1,900,000 Sold Jul 10, 2025

  • 3,524 Sq Ft
  • $539/SF
  • 19 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1888

  475 Maple St, Winnetka, IL 60093

  Just steps from the Village Green, this expansive 5 bedroom/3.2 bath classic sits on a sprawling .3 acre (94' frontage) a walk to everything in the most desirable east Winnetka location. A stylized architectural gem boasts the elegantly designed living space, offering classical charm with soaring ceilings and oversized windows - perfect for today's lifestyle. Enjoy breathtaking views from the

  Paige Dooley Compass

  475 Maple St, Winnetka, IL 60093
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  /53

  $3,000,000 Sold Jul 10, 2025

  • 3,420 Sq Ft
  • $877/SF
  • 14 Days On Market

  • 6 Beds
  • 6.5 Baths
  • Built 1898

  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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  /63

  $11,400,000 Sold Jul 09, 2025

  • 15,784 Sq Ft
  • $722/SF
  • 8 Days On Market

  • 7 Beds
  • 8 Baths
  • Built 2005

  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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  /33

  $1,801,000 Sold Jul 07, 2025

  • 3,645 Sq Ft
  • $494/SF
  • 4 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1924

  143 Fuller Ln, Winnetka, IL 60093

  Enjoy lake breezes on quiet coveted lane, steps to Centennial Park, Elder Beach, train, and schools. Classic 5-bedroom, 3.1-bath center entrance colonial offers a wonderful lifestyle, blending timeless design and solid construction with thoughtful modern updates. A gracious foyer highlights a gracious staircase welcomes you into a beautifully flowing floor plan designed for comfortable living

  Paige Dooley Compass

  143 Fuller Ln, Winnetka, IL 60093
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  /2

  $750,000 Sold Jul 03, 2025

  • 1,600 Sq Ft
  • $469/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1965

  736 Oak St Unit 736, Winnetka, IL 60093

  Welcome to this beautifully renovated townhouse in the heart of Winnetka, located in the coveted New Trier School District. This spacious 3-bedroom, 2.1-bath home offers the perfect blend of style, comfort, and convenience. The open-concept main floor is filled with natural light, featuring a large open kitchen with quartz countertops, a breakfast bar, incredible storage, and stainless steel

  David Chung Compass

  736 Oak St Unit 736, Winnetka, IL 60093
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  /2

  $1,500,000 Sold Jun 30, 2025

  • 3,433 Sq Ft
  • $437/SF
  • 0 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1914

  1293 Scott Ave, Winnetka, IL 60093

  Sold before listing

  Bonnie Tripton @properties Christie's International Real Estate

  1293 Scott Ave, Winnetka, IL 60093
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  /35

  $1,685,000 Sold Jun 30, 2025

  • 2,800 Sq Ft
  • $602/SF
  • 3 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1926

  1149 Scott Ave, Winnetka, IL 60093

  Situated on one third of an acre of beautifully landscaped grounds just steps from town, train, parks, and top-rated schools, this classic Winnetka home offers the ideal combination of convenience, charm, and unbelievable indoor and outdoor spaces. The sun-filled main level offers a functional and elegant layout with beautiful hardwood floors throughout. A spacious living room with a cozy wood

  Danielle Wylie Baird & Warner

  1149 Scott Ave, Winnetka, IL 60093
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  /2

  $570,000 Sold Jun 30, 2025

  • 1,960 Sq Ft
  • $291/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  711 Oak St Unit 408, Winnetka, IL 60093

  Sought after Oak Hill condominium building in the heart of Winnetka. Spacious 1960 sq ft condo on the 4th floor looking west for beautiful sunsets. This 3 bedroom (3rd bedroom currently used as a family room with kitchen access), 2 bath condo offers plentiful closets and has a side by side washer and dryer along with more storage in the laundry room. The primary bedroom is huge with a private

  Laurie Baker Lawlor @properties Christie's International Real Estate

  711 Oak St Unit 408, Winnetka, IL 60093
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  /44

  $2,495,000 Sold Jun 27, 2025

  • 5,800 Sq Ft
  • $430/SF
  • 3 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1908

  548 Cherry St, Winnetka, IL 60093

  Looking for an East Winnetka home full of charm to check all of your boxes? Look no further! Premiere location - walk, cycle, skip to Greeley or New Trier schools, town, train, and lake - it's all here! A covered front entry porch draws you into the welcoming foyer. This spacious open floor plan was designed for ease of living with great traffic "flow" and gobs of natural light thru-out! The

  Sally O'Donnell @properties Christie's International Real Estate

  548 Cherry St, Winnetka, IL 60093
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  /76

  $1,650,000 Sold Jun 26, 2025

  • 3,756 Sq Ft
  • $439/SF
  • 6 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  938 Old Green Bay Rd, Winnetka, IL 60093

  Your own private retreat on a lush, expansive 4/10 acre property! This open, soft contemporary design offers large, light-filled rooms on a idyllic wooded lot plus a 3 car attached garage. An ideal combination of light, and space with an excellent floor plan creates an incredible living experience. Beautiful renovations include a new kitchen and 3 renovated bathrooms, new pitched roofs (2025)

  Joanne Hudson Compass

  938 Old Green Bay Rd, Winnetka, IL 60093
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  /35

  $1,505,000 Sold Jun 26, 2025

  • 2,511 Sq Ft
  • $599/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1986

  989 Ash St, Winnetka, IL 60093

  Showings begin Friday, May 2nd. Discover an exceptional 5-bedroom, 3.1-bath Colonial located in a prime area. Step onto the newly installed bluestone walkway, leading to an inviting foyer with a formal dining room and a living room featuring floor-to-ceiling windows. The kitchen is thoughtfully designed with a sitting counter, stainless steel Bosch appliances, and a planning desk. Adjacent is a

  John Phillips Compass

  989 Ash St, Winnetka, IL 60093
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  /33

  $1,381,000 Sold Jun 25, 2025

  • 3,029 Sq Ft
  • $456/SF
  • 5 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1930

  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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  /23

  $950,000 Sold Jun 20, 2025

  • 2,008 Sq Ft
  • $473/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1926

  283 Ridge Ave, Winnetka, IL 60093

  Two thousand square feet of Winnetka charm, graciousness and elegance. A center entry Dutch colonial in a prime location in Winnetka, walk to schools, town, Metra, etc. A big beautiful semi-circle of windows ushers daylight into the large living room, the foyer grandly separates the living room & dining room, efficient kitchen has easy access to all areas, and additionally, the adorable three

  Marilee Moyer @properties Christie's International Real Estate

  283 Ridge Ave, Winnetka, IL 60093
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  /36

  $2,675,000 Sold Jun 17, 2025

  • 4,251 Sq Ft
  • $629/SF
  • 67 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1937

  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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  /92

  $12,000,000 Sold Jun 17, 2025

  • 9,653 Sq Ft
  • $1243/SF
  • 10 Days On Market

  • 6 Beds
  • 10 Baths
  • Built 2020

  973 Sheridan Rd, Winnetka, IL 60093

  Secluded from it all with only the sound of the waves from Lake Michigan, this immaculate, turn-key lakefront property will make every day feel like a vacation. Behind the gated entrance, you are instantly transported to a private oasis on 1.75 acres with 100 feet of beachfront, and a residence that spans over 18,000 square feet. Built in 2020 by a best-in-class collaboration between Paul

  Cricket King @properties Christie's International Real Estate

  973 Sheridan Rd, Winnetka, IL 60093
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  /64

  $2,350,000 Sold Jun 16, 2025

  • 3,434 Sq Ft
  • $684/SF

  • 4 Beds
  • 7 Baths
  • Built 2007

  384 Hawthorn Ln, Winnetka, IL 60093

  Ideally situated in the heart of East Winnetka, within the coveted radius of New Trier, Greeley, Sheridan Road, and Lake Michigan, this stunning newer-construction home-refinished by renowned Heritage Luxury Builders in 2010-offers timeless elegance and modern comfort. The stately stone and stucco exterior with classic center entry warmly welcomes you inside. Throughout all three finished levels,

  Kelly Dunn Rynes Berkshire Hathaway HomeServices Chicago

  384 Hawthorn Ln, Winnetka, IL 60093
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  /44

  $4,625,000 Sold Jun 16, 2025

  • 8,025 Sq Ft
  • $576/SF
  • 84 Days On Market

  • 6 Beds
  • 8 Baths
  • Built 1926

  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
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  /62

  $1,865,000 Sold Jun 13, 2025

  • 3,600 Sq Ft
  • $518/SF
  • 11 Days On Market

  • 4 Beds
  • 8 Baths
  • Built 2003

  1522 Edgewood Ln, Winnetka, IL 60093

  STUNNING HOME REBUILT IN 2024-25 ACROSS FROM NICK CORWIN PARK - UNBELIEVABLE FINISHES IN THIS STATELY BRICK AND LIMESTONE HOME IN HUBBARD WOODS. NOTE THE 2C GARAGE IS DETACHED. LIVE ACROSS FROM THE PARK, PLAYGROUND & SOCCER FIELDS. EXQUISITE DETAILS INCLUDE HANDSOME MILLWORK, TALL CEILINGS, 4 FIREPLACES, SO MUCH NEW! NEW KITCHEN, APPLIANCES, GRANITE AND STONE SURFACES, PREP ISLAND WITH

  Robin Wilson @properties Christie's International Real Estate

  1522 Edgewood Ln, Winnetka, IL 60093
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  /18

  $1,400,000 Sold Jun 12, 2025

  • 2,466 Sq Ft
  • $568/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  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

  $2,550,000 Sold Jun 12, 2025

  • 4,460 Sq Ft
  • $572/SF
  • 133 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1912

  1155 Chatfield Rd, Winnetka, IL 60093

  Gorgeous new construction home on a quiet street in Hubbard Woods! Close to town, schools, train and the lake! Best value for new construction in Winnetka! First floor includes an open floor plan including a Chef's kitchen with high end appliances, custom cabinetry & spacious island. Kitchen flows into the family room with fireplace and French doors to patio. Too much to mention! Tons of

  Annie flanagan @properties Christie's International Real Estate

  1155 Chatfield Rd, Winnetka, IL 60093
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  /40

  $2,400,000 Sold Jun 11, 2025

  • 6,000 Sq Ft
  • $400/SF
  • 2 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1921

  495 Willow Rd, Winnetka, IL 60093

  Steps from Lake Michigan, this stunning 5BR+/4.1BA brick home is ideally situated on an expansive extra-wide lot (70x186) in a prime walk-to-everything east Winnetka location. Renovated down to the studs with an addition in 2002 plus a kitchen refresh in 2019, this home combines timeless architecture, modern sophistication and thoughtfully designed interiors boasting soaring ceilings, arched

  Paige Dooley Compass

  495 Willow Rd, Winnetka, IL 60093
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  /89

  $5,157,000 Sold Jun 09, 2025

  • 3,117 Sq Ft
  • $1654/SF
  • 0 Days On Market

  • 6 Beds
  • 10 Baths
  • Built 2009

  675 Blackthorn Rd, Winnetka, IL 60093

  Tucked away on idyllic Blackthorn Road in the heart of Winnetka, this stunning newer-construction home offers the rare combination of privacy and convenience. Secluded, yet so close to schools, town, train and all of your favorite Winnetka shops and restaurants, the location cannot be beat. With 7 en suite bedrooms, 7 full baths, 3 half-baths, and a generous lot size of nearly a half-acre, this

  Kathryn Moor Compass

  675 Blackthorn Rd, Winnetka, IL 60093
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  /61

  $9,575,000 Sold Jun 06, 2025

  • 8,086 Sq Ft
  • $1184/SF
  • 25 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 2015

  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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  /37

  $1,000,000 Sold Jun 05, 2025

  • 1,594 Sq Ft
  • $627/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1916

  340 Walnut St, Winnetka, IL 60093

  Welcome to this charming home in East Winnetka! The delightful home boasts a bright, open floor plan that offers exceptional living space. The inviting living room features a stunning white quartz fireplace and elegant shelving, seamlessly connecting to the adjacent dining area. The spacious dining room is perfect for enjoying meals, surrounded by windows, beautiful built-ins, and charming window

  Katie Hauser Compass

  340 Walnut St, Winnetka, IL 60093
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  /30

  $1,207,000 Sold Jun 05, 2025

  • 2,297 Sq Ft
  • $525/SF
  • 4 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1924

  867 Lincoln Ave, Winnetka, IL 60093

  Ideally located between downtown Hubbard Woods and Tower Road Beach, this beautifully maintained Colonial blends timeless charm with thoughtful modern updates. Step inside to find warm hardwood floors and sun-filled rooms that create an inviting, elegant atmosphere. The traditional floor plan offers a formal living room with a wood-burning fireplace, a spacious dining room perfect for gatherings,

  Cricket King @properties Christie's International Real Estate

  867 Lincoln Ave, Winnetka, IL 60093
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  /28

  $2,017,000 Sold Jun 05, 2025

  • 3,170 Sq Ft
  • $636/SF
  • 4 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2008

  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
• 

  

  /51

  $2,400,000 Sold Jun 03, 2025

  • 5,300 Sq Ft
  • $453/SF
  • 1 Day On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2006

  390 Hawthorn Ln, Winnetka, IL 60093

  Nestled in the heart of East Winnetka, an exceptional, "better-than-new" sophisticated home on a wider lot (63') in the best in-town, walk-to-beach/park/train/schools location designed with distinction for the most discriminating buyer. Offering a harmonious blend of modern design and luxurious living with an acute attention to detail and the finest, high-end finishes. Crisp moldings, soaring

  Paige Dooley Compass

  390 Hawthorn Ln, Winnetka, IL 60093
• 

  

  /40

  $1,760,000 Sold Jun 03, 2025

  • 3,708 Sq Ft
  • $475/SF
  • 3 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1890

  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
• 

  

  /54

  $2,520,000 Sold May 30, 2025

  • 4,819 Sq Ft
  • $523/SF
  • 3 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1888

  800 Lincoln Ave, Winnetka, IL 60093

  Come see this classic Winnetka beauty: packed with both vintage charm and all the updates of today! 800 Lincoln Avenue is a beautiful home perfectly situated in sought after East Winnetka location where you can walk to town and the lake. Enter through the charming front porch to a lovely foyer with hand-stenciled floor. Enjoy the bright living and dining room overlooking the tree-lined street,

  Katharine Hackett @properties Christie's International Real Estate

  800 Lincoln Ave, Winnetka, IL 60093
• 

  

  /37

  $2,650,000 Sold May 30, 2025

  • 4,536 Sq Ft
  • $584/SF
  • 6 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1901

  822 Bryant Ave, Winnetka, IL 60093

  One of Winnetka's most extraordinary retreats in the most desired walk to location reminiscent of the iconic homes of the era with a stylized full house renovation and addition in 2004. This "better than new" meticulous lovingly restored Historical Home that blends all of life's comforts from the dreamlike screened porches over 1/2 acre of breathtaking grounds and spectacular kitchen//family room

  Paige Dooley Compass

  822 Bryant Ave, Winnetka, IL 60093
• 

  

  /45

  $2,400,000 Sold May 29, 2025

  • 5,073 Sq Ft
  • $473/SF
  • 3 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1938

  1170 Oakley Ave, Winnetka, IL 60093

  Exquisitely maintained and masterfully designed, this stunning residence on one of Winnetka's most beloved lanes offers the perfect blend of luxury, functionality, and charm. Nestled on an oversized .32-acre, park-like lot, the home is ideally located within walking distance to Hubbard Woods School, Sacred Heart, the Metra, parks, boutique shops, restaurants, coffee houses, the Green Bay Trail,

  Laura Fitzpatrick @properties Christie's International Real Estate

  1170 Oakley Ave, Winnetka, IL 60093
• 

  

  /22

  $1,200,000 Sold May 28, 2025

  • 2,300 Sq Ft
  • $522/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  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
• 

  

  /70

  $2,200,000 Sold May 28, 2025

  • 5,400 Sq Ft
  • $407/SF
  • 133 Days On Market

  • 6 Beds
  • 6.5 Baths
  • Built 1916

  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
• 

  

  /41

  $3,055,000 Sold May 19, 2025

  • 5,461 Sq Ft
  • $559/SF
  • 4 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1894

  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

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