Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 05/25/2019 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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$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, Howard D"
* 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
"Truly a once in a lifetime opportunity, 203 Sheridan is Winnetka's crown jewel. Perfectly sized for easy living, this elegant waterfront home features solid craftsmanship of stone, brick and slate materials with gorgeous European touches throughout. Highlights include over one acre of rarely available waterfront property, one of the most beautiful private sandy beaches on the North Shore, a floor plan that offers sunlit and spacious room sizes, balconies and terraces with stunning views, and a s"
$7,699,999
1215 Whitebridge Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
15,000
SQFT
$513
$/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,"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $7,999,996 TO $7,699,999 
$5,875,000
738 Tower Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,122
SQFT
$825
$/SQFT
0.68
ACRES
2001
BUILT
"Beautifully perched above the lake, this one owner custom-built newer construction home stuns w/lake vistas from all 4 floors of fabulous space. Stately grand entry w/ soaring ceilings, wide reception hall, sweeping staircase & views right to the lake from elegant living rm sets a peaceful tone. Incredible 1st floor w/ideal circular entertaining space & oversized Chef's kitchen that opens to the family rm both overlooking the lake. Separate breakfast rm perfect for watching morning sunrises. Mas"
* PRICE LOWERED - $6,245,000 TO $5,875,000 
$4,999,000
480 Oak Street, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,341
SQFT
$788
$/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"
$4,995,000
919 HILL Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,000
SQFT
$416
$/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"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $5,500,000 TO $4,995,000 
$4,675,000
670 Blackthorn Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,500
SQFT
$374
$/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"
$4,650,000
905 Sunset Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
8,900
SQFT
$522
$/SQFT
0.93
ACRES
1992
BUILT
"One of a kind... like a piece of art... this exclusive transitional masterpiece by Marvin Herman is one that is completely unexpected on award winning grounds by renowned Spanish exterior landscape architect Xavier Vendrall. Once you step inside, you completely arrive at this private retreat built for vacationing, just missing the vineyards.Unexpected reveals w/matching exterior spaces, incredible natural light beaming in all rooms & the best outdoor space in the North Shore w/ the ultimate luxu"
$4,500,000
165 Thorntree Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
11,925
SQFT
$377
$/SQFT
1.12
ACRES
1931
BUILT
"This 1930 Georgian Masterpiece is architect Edwin Clark's finest designs & landscape architect Scott Byron has created gardens & grounds of equal stature on the 1.17 acres. Impeccable condition, this 6 BR, 6.3 bath home works well for today's modern busy family. Updated kit w adjacent fam rm includes 1st flr laundry & over-sized mud rm. MBR offers a sun filled sitting rm, new his and her baths, as well as dressing area. All BRs are of generous size w restored baths. There is also 2nd floor laun"
* LISTED OVER 120 DAYS 
$4,495,000
41 Indian Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
1.75
ACRES
1924
BUILT
"Superb renovation of a Classic English Manor Home paired with magnificent grounds featuring a Boilini pool and pergola. Welcoming entry: marble flooring, leaded glass & elegant staircase. Stunning living rm features custom cabinets & fireplace with detailed mantle. Dining room includes studded fabric walls, mirrored doors & fireplace. Pine paneled library with fireplace and bookcases offers the perfect retreat. Incredible kitchen includes high-end appliances, island with counter seating, breakfa"
$4,295,000
630 Rosewood Avenue, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,500
SQFT
$573
$/SQFT
0.71
ACRES
2020
BUILT
"Transitional, fabulous 7500 sq ft new construction (see floor plans, elevations and site plans under additional info). Or renovate existing home. Or custom build. Set on a fabulous 3/4 acre lot close to town, train and school. Incredible opportunity for your buyers to create their dream home! This home is being constructed by one of the North Shores most experienced and sought after luxury builders who builds award winning one-of-a-kind homes to the highest specifications."
$3,400,000
6 Kent Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,819
SQFT
$499
$/SQFT
0.94
ACRES
1917
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,650,000 TO $3,400,000 
$3,375,000
966 Pine Tree Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,800
SQFT
$496
$/SQFT
0.70
ACRES
2019
BUILT
"Exceptional new construction on app. 3/4 acre; The house is app. 10,000 sq. ft of finished space. 6 bedrooms, 6.1 bath. Special features include gourmet kitchen, walnut wood library, central vac, security system, economical led lighting, terrific lower level with media room, wine cellar and exercise room. Outstanding quality throughout, attention to detail. Plenty of room to add outdoor kitchen and swimming pool! Agent owned/interest."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,475,000 TO $3,375,000 
$3,350,000
1363 Hackberry Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
1.07
ACRES
1951
BUILT
"RARE OPPORTUNITY! This amazing French Provincial home is tucked away on a sensational PRIVATE 1+Acre property overlooking the expansive tranquility of Winnetka Golf Course.This stately white brick home is impeccably scaled to compliment today's modern lifestyle after a COMPLETE REBUILD and design in 2000! Magnificent views of the golf course and of nature can be seen throughout the home. Spacious living, high ceilings,arched entries and floor to ceiling French doors in every room set the tone fo"
$3,300,000
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 - $3,500,000 TO $3,300,000 
$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 a"
* LISTED OVER 120 DAYS 
$3,175,000
310 Myrtle Street, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,500
SQFT
$423
$/SQFT
0.32
ACRES
2015
BUILT
"Stunning two year old new construction coastal style home with all of the bells and whistles in fantastic East Winnetka locale, steps to both Greeley elementary school and New Trier high school, train and town. Chef's kitchen with stainless hood, quartzite counters and top of the line appliances opens to cozy family room, custom-built library, 6 bedrooms with marble baths, 3 car attached garage and fully fenced yard. Expansive finished lower level with sport court, media, wine, exercise and ente"
* PRICE LOWERED - $3,295,000 TO $3,175,000 
$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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,275,000 TO $3,175,000 
$3,095,000
139 De Windt Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,203
SQFT
$499
$/SQFT
0.82
ACRES
1937
BUILT
"VACATION AT HOME! PURE ELEGANCE IS WOVEN THROUGHOUT THIS SENSATIONAL NEW ENGLAND COLONIAL SITUATED ON AN EXCLUSIVE PRIVATE RD. THIS IDEAL .8 ACRE RETREAT IS CONVENIENT TO EVERYTHING-SCHOOLS, TRAIN, TOWN & LAKEFRONT. TIMELESS DESIGN, SPACIOUS RMS, BUILT-INS & DETAILED ARCHITECTURE THROUGHOUT. 16 RMS, 6 BEDRMS W/ OPTION for 7, 5.3 BATHS-ALL SOPHISTICATEDLY DECORATED, UPDATED & MAINTAINED. BRIGHT LIVING RM, PANELED LIBRARY, STUNNING FAMILY RM W/CUSTOM MILLWORK, COOK'S KITCHEN, BRKFAST RM, INVITING "
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,245,000 TO $3,095,000 
$2,999,900
720 Rosewood Avenue, Winnetka IL 60093
7
BEDS
6.4
BATHS
6,870
SQFT
$437
$/SQFT
0.51
ACRES
1996
BUILT
"A stunning, tranquil oasis in one of Winnetka's most premier neighborhoods within blocks to train, town & schools (K-8th). Designed to have totally privacy while maximizing natural light throughout, this custom Nantucket home seamlessly blends interior casual elegance w/the outdoors on a mature landscaped 1/2 acre lot. Finely crafted millwork, soaring ceilings, 4 fps, & custom glass display cabinets all accent the beautiful sunfilled transitions between formal & informal rms. Handsome Office lea"
$2,995,000
701 Hibbard Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,500
SQFT
$461
$/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, "
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,250,000 TO $2,995,000 
$2,950,000
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"
$2,795,000
1555 Hickory Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
8,000
SQFT
$349
$/SQFT
0.63
ACRES
2011
BUILT
"Built in 2011, this 7-bedroom, 8.2 bath, 4-car heated garage, all brick Georgian home on 2/3 acre is the perfect combination of elegance and functionality. The gracious floor plan is both family friendly and perfect for entertaining. From the grand marble foyer, to the tranquil screened-in porch with fireplace and vaulted ceiling, this home feels like a serene retreat. Handsome custom wood paneled office with coffered ceiling, built-in bookshelves, and wood-burning fireplace adjoins the family "
* LISTED OVER 120 DAYS 
$2,790,000
900 Ravine Road, Winnetka IL 60093
7
BEDS
6.4
BATHS
9,650
SQFT
$289
$/SQFT
0.64
ACRES
2005
BUILT
"STUNNING 7BR, 7.1BA newer construction home on one of Winnetka's most beautiful coveted streets! Welcoming foyer leads you to a lovely formal living room with floor-to-ceiling windows & handsome stone FP. Library has terrace, fireplace & custom built-ins. Formal DR w/tray ceiling leads to convenient butler's pantry. Wonderful Chef's kitchen designed by Paul Konstant boasts fine custom cabinetry, top-of-the-line appliances, over-sized island, stone FP & desk/computer area. The bright & sunny brea"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,820,000 TO $2,790,000 
 
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