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Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 09/15/2019 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"
* LISTED OVER 120 DAYS  * 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
"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"
* LISTED OVER 120 DAYS 
$7,300,000
1215 Whitebridge Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
15,000
SQFT
$487
$/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 - $7,630,000 TO $7,300,000 
$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 
$4,900,000
300 Birch Street, Winnetka IL 60093
8
BEDS
6.4
BATHS
10,474
SQFT
$468
$/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"
$4,850,000
745 Sheridan Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,568
SQFT
$641
$/SQFT
0.50
ACRES
1990
BUILT
"THIS MAGNIFICENT FRENCH CHATEAU ON E OF SHERIDAN RD HAS EVERYTHING YOU DREAMED OF!! GRAND FOYER OPENS TO 2-STORY TWIN WINDING STAIRWAY OVERLOOKING SKY, LEADS TO HIGH CEILING WITH OPEN FEELING HUGE ELEGANT LIVING ROOM & GENEROUSLY SIZED ROOMS, ROMANTIC MASTER SUITE W/ FIRE PLACE AND DELUXE BATH (26X15), WALK IN CLOSET (17X11), 6 MORE BEDROOMS INCLUDING 1ST FLOOR GUEST BEDROOM AND MAID BEDROOM. BEAUTIFUL KITCHEN, FANTASTIC LIBRARY, FINISHED BASEMENT W / WET BAR, 2ND KITCHEN, BR, BATH, & THEATER"
$4,699,000
90 Indian Hill Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,735
SQFT
$607
$/SQFT
0.91
ACRES
1935
BUILT
"Indian Hill Road perfection! Grand 1930's white brick Georgian Revival is space that inspires: fresh decor & sensitive improvements coupled with best-in-class luxury construction. The meticulous rebuild took 2 years and EVERYTHING has been done - from behind the walls and floors to all visible surfaces including the exterior (new Marvin windows, slate roof & custom copper work). New to the original floor plan: open concept kitchen/family room/dining area; two laundry rooms; finished 3rd floor; c"
* PRICE LOWERED - $4,885,000 TO $4,699,000 
$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"
* LISTED OVER 120 DAYS 
$4,499,900
738 Tower Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,122
SQFT
$632
$/SQFT
0.68
ACRES
2001
BUILT
"Now down to an incredible lake value as this newer custom-built all brick home just needs 2019 cosmetic face lift as it's all here! Sensational 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 breakfa"
* NEW LISTING 
$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 Bellini 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"
* LISTED OVER 120 DAYS 
$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"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $4,799,000 TO $4,479,000 
$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, dual 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"
* PRICE LOWERED - $4,399,900 TO $4,299,900 
$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."
* LISTED OVER 120 DAYS 
$3,495,000
4 Golf Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,550
SQFT
$534
$/SQFT
0.50
ACRES
2010
BUILT
"Designer, Showcase Home on private lane in Prime Winnetka/Indian Hill Golf Course location. Better than new, Simply Stunning! Sitting on a private Half Acre, this is the home of your dreams! Stunning decor, fabulous circular floor plan & amazing amenities, creating the ultimate in living & entertaining experience. The superior Chef's Kitchen w/ huge center island adjoins the Breakfast Rm w/ one of 5 fireplaces, the fabulous, spacious Family Rm & one of the most used spaces in the home, the belov"
$3,400,000
741 Prospect Avenue, Winnetka IL 60093
4
BEDS
6.4
BATHS
5,010
SQFT
$679
$/SQFT
0.95
ACRES
1942
BUILT
$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 
$3,100,000
6 Kent Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,819
SQFT
$455
$/SQFT
0.94
ACRES
1917
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,300,000 TO $3,100,000 
$3,000,000
12 Kent Road, Winnetka IL 60093
7
BEDS
6.4
BATHS
8,563
SQFT
$350
$/SQFT
0.80
ACRES
1964
BUILT
"Space galore, an ideal layout for family living and entertaining plus a spectacular tranquil setting with a gorgeous pool & pool house....just add your belongings and start enjoying life! The 1st floor offers an exceptionally spacious white kitchen(with double islands and a big eating area) opening to the family room with fireplace; a library/music room off the family room; handsome large private study and more. 2nd floor has 5 of the 7 family bedrooms and a lovely private Master. Terrific 3rd f"
* PRICE LOWERED - $3,350,000 TO $3,000,000 
$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, "
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,300,000 TO $2,975,000 
$2,975,000
966 Pine Tree Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,800
SQFT
$438
$/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 - $3,175,000 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
1555 Hickory Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
0.63
ACRES
2011
BUILT
"Better than new construction all brick Georgian home 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 ref"
$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, "
$2,750,000
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, "
 
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