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Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 12/05/2019 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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71
$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 
23
$8,995,000
203 Sheridan Road, Winnetka IL 60093
4
BEDS
6.4
BATHS
1.10
ACRES
1926
BUILT
"Feel the lake breezes and take in the sounds of the waves from virtually every room in this home. Imagine yourself strolling the vast lawn as you head down for an afternoon on your very own beach! 203 Sheridan features solid craftsmanship of stone, brick and slate materials with gorgeous European touches throughout. Perfectly sized for easy living as a primary or secondary residence, this elegant waterfront home is Winnetka's crown jewel. Highlights include over one acre of rarely available wat"
44
$6,999,980
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 - $6,999,990 TO $6,999,980 
39
$4,795,000
670 Blackthorn Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,500
SQFT
$384
$/SQFT
2020
BUILT
"A new rose will bloom on Blackthorn Road! Proposed 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 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 an"
* PRICE INCREASED - $4,675,000 TO $4,795,000 
48
$4,700,000
919 HILL Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,000
SQFT
$392
$/SQFT
1.25
ACRES
1929
BUILT
"Majestically set on 1.25 acres beyond towering trees, enchanting gardens, expansive front lawn and private drive is this awe inspiring Art Deco Manor Home circa 1929. Impeccably renovated and redesigned by Tigerman McCurry Architects, the final masterpiece, featured in Architectural Digest, exudes streamlined deco sophistication, state of the art infrastructure, stunning timeless white kitchen and baths, custom millwork, custom leaded windows, doors and hardware, seamlessly flowing floor plan an"
* PRICE LOWERED - $4,995,000 TO $4,700,000 
42
$4,489,000
90 Indian Hill Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,735
SQFT
$580
$/SQFT
0.91
ACRES
1935
BUILT
"Classic white, painted-brick Georgian Revival meticulously rebuilt over the last 2 years. EVERTYTHING is new, from the slate roof and Marvin windows, to all of the mechanicals and then some. Open floor plan, serene and drenched in sunlight. Perfectly proportioned rooms with space to entertain or work privately. Designed in a way that feels new and fresh but also classic-this house will hold its value. Thoughtfully curated, calm and neutral but punctuated with hits of drama including a cadet-blue"
* PRICE LOWERED - $4,699,000 TO $4,489,000 
39
$4,479,000
480 Oak Street, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,341
SQFT
$706
$/SQFT
0.58
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 - $4,799,000 TO $4,479,000 
60
$4,299,900
884 Higginson Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
11,000
SQFT
$391
$/SQFT
0.66
ACRES
2014
BUILT
"Very exclusive rare offering of impeccably finished custom home by notable nationally published designer Julia Buckingham. Over 11,000 sq ft of flawless finished space complemented w/an exterior landscape that is equally divine by Chalet w/pergola dining patio, full kitchen equipped w/ brick oven ideal for pizza making, sided fireplace & organic vegetable gardens. Ideal open flr pln w/atrium cascading foyer entrance that leads to all entertaining rms. Sensational throughout w/custom white marbl"
* PRICE LOWERED - $4,399,900 TO $4,299,900 
39
$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 
20
$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"
1
$3,195,000
987 Asbury Court, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,270
SQFT
$510
$/SQFT
0.51
ACRES
2018
BUILT
"Fabulous! Exceptional new construction on gorgeous half acre property amidst spectacular surrounding homes. Open first floor plan features incredible kitchen which opens to family room - all with views of handsome back terrace and yard. Formal living and dining rooms, private study and covered front porch also on first floor. 'All you could want' mudroom accesses heated 2 car att. Also has 1 car detached garage. 2nd fl. has 5 bedrooms including gorgeous master suite with large private deck. 3 "
30
$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."
72
$3,100,000
6 Kent Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,819
SQFT
$455
$/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 - $3,300,000 TO $3,100,000 
37
$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 
32
$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"
33
$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, "
65
$2,750,000
139 De Windt Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,203
SQFT
$443
$/SQFT
0.82
ACRES
1937
BUILT
"VACATION AT HOME! UNSURPASSED QUALITY IS WOVEN THROUGHOUT THIS GORGEOUS NEW ENGLAND COLONIAL SITUATED ON AN EXCLUSIVE PRIVATE ROAD IN ONE OF WINNETKA'S PREMIER NEIGHBORHOODS, THIS IDEAL .8 ACRE RETREAT IS CONVENIENT TO EVERYTHING-SCHOOLS, TRAIN, TOWN. TIMELESS DESIGN, SPACIOUS ROOMS & DETAILED ARCHITECTURE THROUGHOUT. 16 RMS, 6 BDRMs, 5.3 BATHS-ALL BEAUTIFULLY DECORATED, UPDATED & MAINTAINED.BRIGHT LIVING RM, RICH PANELED LIBRARY, STUNNING FAMILY RM W/CUSTOM MILLWORK, COOK'S KITCHEN, BRKFST RM, "
32
$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 
44
$2,495,000
1360 Trapp Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,226
SQFT
$345
$/SQFT
0.65
ACRES
2019
BUILT
"Now Finished and Ready to Move In. Exquisite Modern Farmhouse with over 7000 sq/ft of living space on 2/3 of an acre on a secluded cul-de-sac. This home was taken down to the studs and completely overhauled. It has been redesigned for modern living. Every high-end finish, sourced both locally and internationally, has been hand-selected by an interior designer. Amenities include: Brazilian quartzite countertops, backsplash and quartz waterfall island; custom soapstone sink and Brizo fixtures, mod"
* PRICE LOWERED - $2,595,000 TO $2,495,000 
52
$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"
53
$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/"
* PRICE LOWERED - $2,295,000 TO $2,195,000 
12
$2,100,000
79 Woodley Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,268
SQFT
$289
$/SQFT
1.25
ACRES
1964
BUILT
"One-of-a-kind spectacular contemporary beauty, built by renowned North Shore builder Hemphill as his personal residence. Classic pillars, large front veranda, grand-scaled rooms and high ceilings create luxurious one floor living. Exceptional home sited on 1.25 acres with secluded, inviting pool and located on prestigious Woodley Road. Spectacular sunroom spans rear of home and overlooks remarkable, private back yard. Very large rooms include elegant Living Room (23x30) and Dining Room (17x23),"
* PRICE LOWERED - $2,395,000 TO $2,100,000 
40
$2,099,000
985 Pine Tree Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,359
SQFT
$330
$/SQFT
0.50
ACRES
2003
BUILT
"STATELY WINNETKA HOME ON INCREDIBLE LOT with lush landscaping, the elegant interior has been newly remodeled and professionally designed and shows beautifully from the updated white chefs kitchen w/ quartz counter-tops & spacious island open to sunlit breakfast area to the vaulted ceiling family room with incredible views of the over sized patio and killer backyard - this home offers incredible value and luxury from top to bottom and includes remodeled upstairs baths, a first floor bedroom suite"
37
$2,095,000
850 Lamson Drive, Winnetka IL 60093
4
BEDS
6.4
BATHS
5,088
SQFT
$412
$/SQFT
0.46
ACRES
1955
BUILT
"Lives Like a Ranch!! First floor Master with an additional bedroom suite on the main floor. Two additional large bedrooms on the second floor. Master includes his& her bathrooms and walk in closets, large picture windows facing the back yard. Lovely living room and family room. Open floor plan with kitchen open to the family room. Stunning kitchen w huge breakfast room, fireplace, loads of storage and a huge mudroom/laundry. Fabulous kids or guest suites on the second level w huge play area a"
 
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