Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 07/18/2019 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
"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
"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 
$7,630,000
1215 Whitebridge Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
15,000
SQFT
$509
$/SQFT
"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 - $7,699,999 TO $7,630,000 
$5,299,900
738 Tower Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,122
SQFT
$744
$/SQFT
0.68
ACRES
"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"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $5,875,000 TO $5,299,900 
$4,995,000
919 HILL Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,000
SQFT
$416
$/SQFT
1.25
ACRES
"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 
$4,885,000
90 Indian Hill Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,735
SQFT
$632
$/SQFT
0.91
ACRES
"Indian Hill Road perfection! Grand 1930's white brick Georgian Revival hits all the high notes: 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;"
$4,850,000
745 Sheridan Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
7,568
SQFT
$641
$/SQFT
0.50
ACRES
"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"
$4,799,000
480 Oak Street, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,341
SQFT
$757
$/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 - $4,999,000 TO $4,799,000 
$4,675,000
670 Blackthorn Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
12,500
SQFT
$374
$/SQFT
"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 
$4,495,000
41 Indian Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
1.75
ACRES
"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 
$4,399,900
884 Higginson Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
11,000
SQFT
$400
$/SQFT
0.66
ACRES
"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"
$4,295,000
630 Rosewood Avenue, Winnetka IL 60093
5
BEDS
6.4
BATHS
7,500
SQFT
$573
$/SQFT
0.71
ACRES
"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 
$3,950,000
165 Thorntree Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
11,925
SQFT
$331
$/SQFT
1.12
ACRES
"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  * PRICE LOWERED - $4,500,000 TO $3,950,000 
$3,495,000
4 Golf Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,550
SQFT
$534
$/SQFT
0.50
ACRES
"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! It has it all! Stunning decor, fabulous circular floor plan & amazing amenities, creating the ultimate in living & entertaining experience. The superior Chef's Kitchen w/ huge center island features a Breakfast Rm w/ one of 5 fireplaces adjoining the fabulous Family Rm & Screen Porch. Both the Porch & stunni"
$3,350,000
12 Kent Road, Winnetka IL 60093
7
BEDS
6.4
BATHS
9,300
SQFT
$360
$/SQFT
0.80
ACRES
"This house has it all! Space galore and an ideal layout for family living and entertaining plus a gorgeous yard with a spectacular 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 office and more. 2nd floor has 5 of the 7 family bedrooms and a lovely private Master."
$3,300,000
58 Woodley Road, Winnetka IL 60093
7
BEDS
6.4
BATHS
"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 - $3,500,000 TO $3,300,000 
$3,300,000
6 Kent Road, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,819
SQFT
$484
$/SQFT
0.94
ACRES
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,400,000 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
"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
966 Pine Tree Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
6,800
SQFT
$467
$/SQFT
0.70
ACRES
"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 - $3,275,000 TO $3,175,000 
$2,995,000
1334 Trapp Lane, Winnetka IL 60093
5
BEDS
6.4
BATHS
8,200
SQFT
$365
$/SQFT
0.65
ACRES
"Extraordinary custom brick & limestone newer construction home by Highgate Builders on sought-after Winnetka private lane in fabulous walk-to location. Spacious throughout, this home offers extra high ceilings, gleaming hardwood floors, custom moldings & millwork, slate roof & is situated on an expansive, 1/3 acre lot. Spectacular gourmet kitchen features two islands - one butcher block & one marble, as well as a sunny breakfast space & wonderful sitting area with fireplace. Magnificent formal r"
$2,950,000
644 Pine Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
2.39
ACRES
"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
701 Hibbard Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,500
SQFT
$430
$/SQFT
1.78
ACRES
"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, "
$2,795,000
1555 Hickory Lane, Winnetka IL 60093
6
BEDS
6.4
BATHS
8,000
SQFT
$349
$/SQFT
0.63
ACRES
"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 
$2,750,000
139 De Windt Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
6,203
SQFT
$443
$/SQFT
0.82
ACRES
"NEW PRICE! VACATION AT HOME! PURE JOY IS WOVEN THROUGHOUT THIS SENSATIONAL NEW ENGLAND COLONIAL SITUATED ON AN EXCLUSIVE PRIVATE ROAD. THIS IDEAL .8 ACRE RETREAT IS CONVENIENT TO EVERYTHING-SCHOOLS, TRAIN, TOWN & LAKEFRONT. TIMELESS DESIGN, SPACIOUS ROOMS, 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,"
* PRICE LOWERED - $2,895,000 TO $2,750,000 
 
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