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Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 02/25/2020 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Winnetka homes for sale or other Winnetka real estate, please contact us and one of our knowledgeable Winnetka REALTORS® would be pleased to assist you.


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$9,500,000
68 Locust Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
2.04
ACRES
2008
BUILT
"A starstruck beauty! The only Richard Landry house east of Beverly Hills 90210. Set on over 2 acres of award winning landscaped designed grounds by Scott Byron, this home has one common thread woven throughout, 'quality' abound in every inch of this home. With 6 beds, garages for 9 cars, spa room, gym, theater, wine cellar room w/pebble stone floors complemented with a handcrafted restaurant quaility bar, pool and spa, this is the 'ultimate' entertainment destination. Experts Mick DeGiulio, Howa"
* PRICE LOWERED - $9,999,999 TO $9,500,000 
$8,995,000
203 Sheridan Road, Winnetka IL 60093
4
BEDS
6.4
BATHS
1.10
ACRES
1926
BUILT
"203 Sheridan Road, Winnetka is one of Chicagoland's premier WATERFRONT properties, located in the city's most exclusive suburb. This is the best of the best! Perfect for either a primary or secondary residence and conveniently close to Chicago's downtown, Northwestern University, O'Hare Intl. Airport, and Chicago Executive Airport. This gorgeous property is easily maintained, and the charming home features solid construction of stone, brick, slate and copper with gorgeous European craftsmanship "
$6,999,925
1215 Whitebridge Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
15,000
SQFT
$467
$/SQFT
2001
BUILT
"This waterfront home is 15,000 ft. of Wowed Decadence! This extraordinary brick and limestone Villa is situated perfectly among the bluffs of Lake Michigan. Stargaze from one of the perfectly placed verandas or daydream from the rolling roar of the waves! Offering 6-bedrooms, 6-full baths & 4 powder rooms, this spectacular home offers a total resort lifestyle. Features include 7 fireplaces, a grand foyer boasting marble mosaic floors with a double floating staircase, hand-beveled walnut floors,"
* PRICE LOWERED - $6,999,935 TO $6,999,925 
$4,795,000
670 Blackthorn Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,500
SQFT
$384
$/SQFT
2020
BUILT
"A new rose is blooming on Blackthorn Road! New construction home on deep 3/4 + acre property on private street. Fantastic layout with all of the conveniences for today's lifestyle including fully equipped state of the art chef's kitchen, 7 bedrooms including highly desirable first floor bedroom suite with bath, 4 car attached garage, screened porch, elevator, sport court, golf simulator, media room and so much more. Very unique deep property with many possibilities including build out of pool. "
* PRICE INCREASED - $4,675,000 TO $4,795,000 
$4,375,000
90 Indian Hill Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,735
SQFT
$566
$/SQFT
0.91
ACRES
"Classical point of view meets current, fresh design. Rare offering on Winnetka's lovely Indian Hill Road, this house was completely rebuilt over the past 2 years. Scale, proportion and volume are just right. This generous house envelops you in a bright, sunny canvas. Traditional elements become sculptural - nothing is overdone. The circular flow and abundant natural light combine to create harmony and serenity. Definitely a feel-good house with open spaces to gather, cook and dine; private space"
* PRICE LOWERED - $4,489,000 TO $4,375,000 
$4,250,000
919 HILL Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,000
SQFT
$354
$/SQFT
1.25
ACRES
1929
BUILT
"Extraordinary value-exceptional offering! Majestically set on 1.25 acres beyond towering trees, enchanting gardens, expansive front lawn and private drive appears this awe inspiring Art Deco Manor Home circa 1929. Taken to the studs, impeccably renovated and redesigned by Tigerman McCurry Architects, the final masterpiece, was featured in Architectural Digest, and exudes streamlined deco sophistication, state of the art infrastructure, stunning timeless white kitchen and baths, custom millwork, "
* PRICE LOWERED - $4,700,000 TO $4,250,000 
$3,999,999
480 Oak Street, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,341
SQFT
$631
$/SQFT
0.50
ACRES
"Built in 1913 and designed by notable Chicago architect Benjamin Marshall, 480 Oak Street remains a vestige of the historic grand estates of Winnetka. Today, this incomparable French Regency residence commands an exceptional waterside location showcasing panoramic views of Lake Michigan as well as enjoying the convenience of being minutes from the Village. The current owners, in collaboration with prestigious architects and engineers undertook a three year restoration and preservation of the ho"
* PRICE LOWERED - $4,479,000 TO $3,999,999 
$3,700,000
300 Birch Street, Winnetka IL 60093
8
BEDS
6.4
BATHS
10,474
SQFT
$353
$/SQFT
1.45
ACRES
1964
BUILT
"A spectacular and unequaled opportunity in the heart of Winnetka! Sited on a private 1.45 acres this incomparable French Regency style estate represents the ultimate in beauty and lifestyle. Gracious proportions, elegant finishes, excellent construction and maintenance are evidenced throughout the property that boasts 18 rooms including grand sized formal rooms, a light-filled 2-story foyer, enormous family room, stunning California room, library, 3 room master suite w his and her baths, 1st flo"
* PRICE LOWERED - $4,900,000 TO $3,700,000 
$3,400,000
741 Prospect Avenue, Winnetka IL 60093
4
BEDS
6.4
BATHS
5,010
SQFT
$679
$/SQFT
0.95
ACRES
1942
BUILT
"Sited on .95 acre in prime East Winnetka location this glamorous white brick residence was designed by renowned architect Jerome Cerny. The home is prominently located on East Winnetka's most desirable street. The elegant floor plan is introduced by a stunning circular foyer that flows graciously into both the formal and casual areas. The main floor rooms are spacious w rich architectural detail and highlighted by sweeping views of the extensive property. The sun-filled, updated white kitchen a"
$3,349,000
735 Ardsley Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,256
SQFT
$462
$/SQFT
1.08
ACRES
1930
BUILT
"Wow is the first impression! Enter through a bridge of pine trees to this Stately English Country Tudor on one of Winnetka's few exclusive private roads. Grand yet warm, this magnificent home is a truly spectacular property! Rare for the North Shore, over an acre of rolling landscaped yard! This breathtaking home is rich in detail! Elegant foyer leads to several rooms including a private office with powder room, a gracious living room with elegant fireplace & floor to ceiling windows, and"
$3,179,000
4 Golf Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,618
SQFT
$480
$/SQFT
0.50
ACRES
2010
BUILT
"Stunning 6 bedroom, 7.2 bath custom home in the heart of Winnetka! Sitting on a tranquil 1/2 acre, this impressive visual home exudes timeless elegance & incredible warmth. Truly unique! Stunning two story entry with spiral staircase welcomes you to the beautiful living room & dining room, both with gas fireplaces. Exquisite architectural detailing throughout boasts 7 fireplaces, (2 see-through), generous spaces, soaring ceilings & gleaming hardwood floors. Stunning Chef's kitchen w/ tailor-mad"
$3,175,000
560 OAK Street, Winnetka IL 60093
5
BEDS
6.4
BATHS
4,900
SQFT
$648
$/SQFT
0.32
ACRES
2018
BUILT
"New construction in prime East Winnetka. Walk to beach, Greeley school, New Trier, train and town. Six bedrooms, 5.1 baths, sport court with 17' ceiling, gourmet kitchen with top of the line appliances, walnut library, timeless elegance with exquisite finishes and craftsmanship. Attention to detail. Led lighting, foam insulation, fully equipped 4K movie theater, refrigerated wine cellar, heated bath floors. Built by Premier North shore builder. Agent owned/interest."
$2,995,000
987 Asbury Court, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,270
SQFT
$478
$/SQFT
0.51
ACRES
2018
BUILT
"Fresh and fabulous! Exceptional new construction on gorgeous half acre property amidst beautiful surrounding homes. Open first floor plan features incredible kitchen which opens to family room - all with views of private back terrace and yard. Formal living and dining rooms, private study and covered front porch all add to the appeal. 'All you could want' mudroom accesses heated 2 car att. Charming detached 1 car detached garage an added bonus. 2nd fl. has 5 bedrooms including gorgeous master "
$2,985,000
6 Kent Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,819
SQFT
$438
$/SQFT
0.94
ACRES
1917
BUILT
"Privacy is priceless!.94 acre lot in the heart of Winnetka.Location,Location,Location says it all!You won't find this level of lush,green privacy in a beautiful, light filled French Country home set down a private 150 ft driveway.Steps from Winnetka schools,shopping district & train.For your client that values complete anonymity, this 6800 sq ft 5BR/5BA home is in pristine & updated condition.No detail overlooked, fresh paint inside & out,new cedar shake roof & copper gutters.Huge 847 sq ft DeGu"
* PRICE LOWERED - $3,100,000 TO $2,985,000 
$2,975,000
58 Woodley Road, Winnetka IL 60093
7
BEDS
6.4
BATHS
1939
BUILT
"Completely renovated, expanded & enhanced this spectacular Woodley Road residence is situated on nearly an acre of sweeping lawns, manicured hedges & mature trees. The 3-story Georgian home boasts well over 10,000 sq ft of living space highlighted by exceptional architectural detail, hardwood & marble floors, abundant windows, grand scaled rooms. Each detail is impeccable, elegant and maintained to perfection. The main floor includes a stunning receptional halll, formal living & dining rooms, "
* PRICE LOWERED - $3,300,000 TO $2,975,000 
$2,875,000
77 Fox Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
5,916
SQFT
$486
$/SQFT
1.55
ACRES
1948
BUILT
"A rare offering! Gracious traditional home set on 1.5 idyllic acres on coveted Fox Lane. Superior construction. Exquisite details. High ceilings. Hardwood floors. 4 fireplaces. Natural light radiates from every direction through tall divided light windows and French doors for endless views of picturesque gardens. Welcoming foyer, grand living room, and dining room designed for entertaining. Intimate library and family room lend a classic 'sit a while' warmth. Cook's kitchen with top-line applian"
$2,795,000
701 Hibbard Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,500
SQFT
$430
$/SQFT
1.78
ACRES
1955
BUILT
"Rarely available 1.8 acre parcel showcasing an exceptional one-level home in prime central Winnetka location. Inspired design, elegant taste, finest materials, superb construction in this one-of-a-kind 6500sf renovated home. Floor-to-ceiling windows across entire east side offer views of sweeping lawns, gardens, mature trees & fabulous pool area. Heart of the home is the stunning Great Room w open spaces to dine, relax, gather. It features 11' cove ceilings, hand laid oak floors, rich paneling, "
$2,745,000
139 De Windt Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,203
SQFT
$443
$/SQFT
0.82
ACRES
1937
BUILT
"Show stopping in every possible way...this exceptional home on over 8/10 of an acre is a hidden gem. Located on one of Winnetka's 'exclusive' private roads, this home boasts quality throughout. The timeless design, spacious rooms and detailed architecture highlight the beauty even more. The first floor offers grand entertaining rooms and cozy family gathering spaces including bright formal living and dining rooms, a rich paneled library, inviting sunroom with views of the bluestone courtyard,"
* NEW LISTING 
$2,700,000
644 Pine Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
2.39
ACRES
1928
BUILT
"DRAMATIC PRICE CHANGE! A RARE OPPORTUNITY TO OWN A TRUE COUNTRY ESTATE IN THE HEART OF WINNETKA. THE EDWIN CLARK DESIGNED ENGLISH COUNTRY HOUSE, COACH HOUSE, POOL & AND VAST OPEN LAND RESIDES ON 2.39 ACRES. THE LARGER PORTION IS 1.7 ACRES. THE BALANCE IS A .65 ACRE BUILDABLE LOT WITH A POOL & POOL HOUSE, ACCESSED, IF DEVELOPED, BY AN EASEMENT FROM HIBBARD RD. THE HOUSE ITSELF IS THE PERSONIFICATION OF CHARMING. INVITING, WARM, APPEALING ARE OTHER APPROPRIATE ADJECTIVES! KNOTTY PINE PANELED LIV"
* PRICE LOWERED - $2,950,000 TO $2,700,000 
$2,699,000
29 Woodley Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
1967
BUILT
"Exceptional, custom renovation/rebuilt home in tranquil setting on inner Woodley Road. This gracious home has been completely renovated and offers an ideal floor plan for today's lifestyle. 1st fl w/ large LR with fireplace and elegant dining room (both overlooking pool, patio and deep property), gorgeous, well-designed bar which opens to dining and living rooms (perfect for entertaining), exquisite kitchen with sunny southern breakfast area overlooking patio and pool and opening to adjacent F"
$2,699,000
1555 Hickory Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
8,400
SQFT
$321
$/SQFT
0.67
ACRES
2010
BUILT
"Exceptional custom all-brick Georgian home tucked away on private 2/3 acre. Gracious circular floor plan is entertainer's dream & pairs elegance w/functionality. Grand marble foyer welcomes you to this timeless home w/exquisite trim work, high-end finishes, & thoughtful design. Handsome custom wood paneled office w/coffered ceiling, built-in bookshelves, & wood-burning fireplace adjoins the family room through French doors. High-end designer white marble kitchen w/ custom cabinetry, Thermador "
$2,299,000
174 Mary Street, Winnetka IL 60093
4
BEDS
6.4
BATHS
6,500
SQFT
$354
$/SQFT
0.36
ACRES
2019
BUILT
"Fresh, open design in a gorgeous setting on a large, lush lot just steps from Lake Michigan, parks, town and train plus the excellence of Glencoe schools! This exceptional home has been designed to cater to the experiences of everyday living and fabulous entertaining. The open flow between the kitchen and family room, dining and living rooms is ideal - all rooms overlook the expansive and private back yard. Finely finished with wide plank oak flooring, tranquil tones choices, thoughtful lighti"
$2,195,000
373 Elder Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
0.30
ACRES
2013
BUILT
"Location,location, location! Exceptional newer home located on large, gorgeous and private lot in east Winnetka steps from Elder Beach! Priced well below the competition! Ideal floor plan for today w/ open flow between rms and lovely views of professionally landscaped, tranquil back yard w/ lush plantings and serene koi pond plus 4 car garage parking! 1st fl has fabulous kitchen w/ island opening to FR w/ fireplace. DR connects to kitchen w/ elegant butler's pantry. Also on 1st is formal LR w/"
$2,149,900
44 INDIAN HILL Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
5,200
SQFT
$413
$/SQFT
0.88
ACRES
"Welcome to Forty-FORE Indian Hill...the best value to be offered on the Indian Hill Golf Course! With exquisitely landscaped grounds with mature trees situated on nearly 1 acre, this beautiful home boasts fabulous southern exposure overlooking the 5th hole of Indian Hill Golf Course. Casual elegance radiates throughout this sunny & spacious home with a warm & inviting expansive floor plan woven w/casual elegance. This house just feels right w/ fabulous everyday living w/gracious rms sizes & circ"
* PRICE LOWERED - $2,199,900 TO $2,149,900 
 
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