Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 07/21/2017 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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$12,900,000
735 Sheridan Road, Winnetka IL 60093
7
BEDS
8
BATHS
2.70
ACRES
1905
BUILT
"Set on almost three acres of incredible sweeping grounds from Sheridan Road to Lake Michigan, there has never been an estate offered quite like this. Timeless and impossible to replicate, this bedrock British Colonial with matching Coach House is one of the most memorable houses on Sheridan Road today. It is hard to not pass the home and stare at its beauty and grandeur. Even better is the 170 foot wide clear views of beautiful Lake Michigan which is unmatched to any lakefront property. With a"
* LISTED OVER 120 DAYS 
$11,900,000
68 Locust Road, Winnetka IL 60093
5
BEDS
10
BATHS
27,000
SQFT
$441
$/SQFT
2.25
ACRES
2008
BUILT
"To have a Richard Landry house in the North Shore is truly legendary in its own right, one of the most renowned architects of our time has created this home so superior in design & flawless in execution, that it is featured in his very own book, Private Estates. Set on over 2 acres of award winning landscaped designed grounds, this home has one common thread woven throughout, quality abound in every inch of this 26,500 sq. ft. museum-like level masterpiece built by GA Johnson & Son. The architec"
$9,750,000
1215 Whitebridge Hill Road, Winnetka IL 60093
6
BEDS
10
BATHS
15,000
SQFT
$650
$/SQFT
2001
BUILT
"15,000 ft. of Wowed Decadence! This extraordinary brick and limestone Villa is situated perfectly among the bluffs of Lake Michigan. Whether you stargaze from one of the perfectly placed verandas or daydream from the rolling roar of the waves, it's all here for the taking! Offering 6-bedrooms, 6-full baths & 4 powder rooms, this spectacular home offers a total luxury lifestyle. Features include 7 fireplaces, a grand foyer boasting marble mosaic floors with a double floating staircase, hand-beve"
$6,495,000
480 Oak Street, Winnetka IL 60093
5
BEDS
5
BATHS
0.50
ACRES
"Not many Winnetka lake homes have an in town location with a beautiful tiered veranda that leads to a sandy, 95 ft wide beach like 480 Oak. This Benjamin Marshall French Regency Villa home was extensively renovated over a 3 year time frame w/ interiors restored using the best of the best materials. Incredible & extensive bluff work completed by notable Jacobs, Ryan & Associates as no expense was spared in design & execution. Once the carriage house for the Hayes Mansion, this home is scaled bea"
* LISTED OVER 120 DAYS 
$4,999,000
20 Indian Hill Road, Winnetka IL 60093
5
BEDS
9
BATHS
1996
BUILT
"Spectacular 2017 kitchen! Incredible expanse with endless natural light and breathtaking views of the grounds. Rare idyllic 1.3 acre private estate w/golf course vistas on prestigious Indian Hill Rd. Masterfully designed collaboration of architect & homeowner created Old World quality built to the highest standard with exacting craftsmanship. Serene, and dramatic open floor plan with lofty ceilings on breathtaking grounds. Classic architecture & sophisticated decor for discriminating buyer. Vast"
$4,995,000
5 Indian Hill Road, Winnetka IL 60093
7
BEDS
11
BATHS
1.80
ACRES
1922
BUILT
"Extraordinary home on 2 acres of spectacular manicured grounds with pool, spa, 3-4 BR guest house - all w/magnificent golf course views. Interior celebrates fabulous rooms of masterful design. DeGuilio cook's kitchen, grand entertaining rooms, warm, inviting family rooms. Screened porch w/ fplc, 6 BRs w/ bths en suite incl wonderful master stewith gorgous new bath and sitting room (2017), 3rd fl bonus space and fun bunk room. Indoor current pool, 33 foot sport court. 6 car garage parking. An unp"
* NEW LISTING 
$4,450,000
3 Golf Lane, Winnetka IL 60093
7
BEDS
8
BATHS
1.60
ACRES
1921
BUILT
"EXCEPTIONAL! The word to describe this Estate nestled on a breathtaking 1.6 acres 71003 sq ft in the heart of Winnetka's Indian Hill Road location.The brick slate roof main house and coach house are better than new-gutted to the studs in 2008 2012 combining all modern amenities with unparalleled architectural features. The main house features tiles reclaimed from a Chateau in France. All the wood in the home reclaimed Mushroom Wood from a property in West Virginia.4 fireplaces. Expansive, open f"
* PRICE LOWERED - $4,795,000 TO $4,450,000 
$4,275,000
635 Blackthorn Road, Winnetka IL 60093
5
BEDS
8
BATHS
7,800
SQFT
$548
$/SQFT
2018
BUILT
"Exceptional new construction on app. 2/3 acre; Total sq.ft. appr. 12,000 sq. ft finished space. 6 bedrooms, 6.2 bath. Special features include gourmet kitchen, walnut wood library, media room, wine cellar, central vac, security system, economical led lighting, terrific lower level w/sport court and exercise room. Outstanding quality throughout, attention to detail. Still time to customize and make it your own! Agent owned/interest."
$3,995,000
861 Bryant Avenue, Winnetka IL 60093
6
BEDS
9
BATHS
7,965
SQFT
$502
$/SQFT
0.57
ACRES
2017
BUILT
"Stately Limestone 7 bed/7.2 bath home located in one of the most sought after areas of east Winnetka. Walking distance to lake and town, this NEW CONSTRUCTION has all the amenities one could desire. All luxury high-end finishes combined with grandly scaled rooms create a truly breathtaking home. Approx. 7965 Sqft. above ground combined with 3177 Sqft finished lower level. A stunning designer kitchen and family room w/fireplace opens out to a stone terrace. Hardwood floors throughout guides one t"
$3,975,000
790 Prospect Avenue, Winnetka IL 60093
6
BEDS
8
BATHS
6,000
SQFT
$662
$/SQFT
0.40
ACRES
2018
BUILT
"Another outstanding house in Winnetka! App. 9,000 sq.ft of finished space with 7 Bedrooms & 7.1 Baths. Special features include gourmet Kitchen w/top of the line appliances including espresso/cappuccino machine, cherry wood custom library, fully equipped movie theater, refrigerated wine room, back-up generator, enclosed porch, sports court, great lower level and much, more. Agent has interest in the home."
* NEW LISTING 
$3,900,000
58 Woodley Road, Winnetka IL 60093
7
BEDS
10
BATHS
1939
BUILT
"Extensively 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, beautiful light fixtures, abundant windows, grand scaled rooms. Each detail is impeccable, elegant and maintained to perfection. The main floor includes formal living & dining rooms, a h"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $4,100,000 TO $3,900,000 
$3,495,000
865 Gordon Terrace, Winnetka IL 60093
5
BEDS
7
BATHS
9,350
SQFT
$374
$/SQFT
2017
BUILT
"865 Gordon Terrace was inspired by the magnificent Shingle Style homes found on Maine's rugged seacoast. This home has very large room sizes and an exceptionally thoughtful floor plan, which yields a home that holds true to its traditional styling with the livability of today's most engaging contemporary homes. The architecture and finishes serve the functional needs and aesthetic demands of today's homeowner: large kitchen/great room with top of the line Wolf/Subzero appliances, many windows to"
* LISTED OVER 120 DAYS 
$3,475,000
685 Locust Street, Winnetka IL 60093
5
BEDS
8
BATHS
4,850
SQFT
$716
$/SQFT
0.33
ACRES
2016
BUILT
"Fantastic new construction on a private, wooded property on one of the most desirable streets in Winnetka. Proposed All luxury high end finishes are included. Slate roof. Copper gutters. Chef's kitchen with top of the line cabinetry and appliances. Custom Built Library. 4 car garage. 6 En Suite Bedrooms with Marble Baths. Lower level with Sport Court with 17 ft. ceilings, Media Room, Wine Cellar, Exercise & Recreation room. Construction has begun, collaborate with our team to customize the ho"
$3,475,000
966 Pine Tree Lane, Winnetka IL 60093
5
BEDS
8
BATHS
6,700
SQFT
$519
$/SQFT
0.70
ACRES
2018
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. Still time to customize and make it your own! Agent owned/interest."
$3,400,000
90 Locust Road, Winnetka IL 60093
6
BEDS
6
BATHS
1.47
ACRES
1925
BUILT
"Stately Georgian home w gated entry on 1.47 acres. Classic design w fine detailing & all the amenities of a new home. Gracious entry foyer w hdwd flrs, elegant liv rm w fplc, bookshelves & hdwd flrs. Music rm w arched entry could be din rm. Spectacular heated sun rm w arched windows & bluestone opens to expansive grounds & pool. Inviting fam rm is adjacent to 1st flr office & butlers pantry. Cook's kit features island, brkfst area, high end appliances, wood cabinetry, stone flrs & marble counter"
$3,399,000
955 Old Green Bay Road, Winnetka IL 60093
6
BEDS
5
BATHS
5,980
SQFT
$568
$/SQFT
1.25
ACRES
1909
BUILT
"This beautiful 1909 Prairie home has been brought into the 21st century. Architect Stuart Cohen transformed this exceptional stucco home into a fully functional family-style home with space and style. The home has been renovated to perfection and completely rebuilt and taken down to the studs. Once owned by the Greeley family, this beautifully restored home sits on 1.25 acres, surrounded by ravines on two sides and a gorgeous outdoor water feature that is the perfect backdrop to enjoying your fa"
$3,395,000
62 WOODLEY Road, Winnetka IL 60093
6
BEDS
6
BATHS
7,000
SQFT
$485
$/SQFT
1.55
ACRES
1933
BUILT
"Incredible value for this caliber of home set on 1.55 acres of magnificant grounds on premier Woodley Rd. Expansive floorpln w/gracious rooms & impeccable details as this traditional home exudes current style & grace. Double atrium formal entry w/ elegant bridal staircase steps down to beautiful formal living room w/stone Parisian fireplace. Fabulous sunroom & dining rm w/de Gournay wallpaper beautifully overlook the lush backyard. Phenomenal white marble kitchen by notable kitchen designer Obr"
* LISTED OVER 120 DAYS 
$3,395,000
8 Longmeadow Road, Winnetka IL 60093
5
BEDS
10
BATHS
0.94
ACRES
2007
BUILT
"Spectacular custom home designed by Scott Javore with fabulous flow, grandly scaled rooms for entertaining and expansive, lush property with glorious southern exposures. 1st fl has elegant entrance hall, large LR and DR w/ fplcs, gourmet kitchen and breakfast rm (w/fplc) opening to delightful loggia w/ fplc. Huge family room w. fplc flows from kitchen; 1st fl office with full BA and laundry rm complete 1st fl. 2nd fl. has luxurious master suite w/ private deck, 3 add'l BRs and 3 BAs, plus large "
* LISTED OVER 120 DAYS 
$3,350,000
45 Woodley Road, Winnetka IL 60093
5
BEDS
7
BATHS
8,195
SQFT
$409
$/SQFT
2.18
ACRES
1952
BUILT
"An exceptional oasis situated on a magnificent, private 2.5 acre setting featuring amazing gardens & landscaping. The ultimate in outdoor living & entertaining w blue stone patios, tennis court, gorgeous pool, pool house w/bar, kitchen & shower bath. Floor to ceiling windows, in virtually all major rooms provides light and endless views of the gardens & grounds & comfort of this unique & gracious home. This home has it all, a privately located first floor master suite w/fireplace & his & hers ba"
$3,150,000
335 White Oak Lane, Winnetka IL 60093
5
BEDS
6
BATHS
0.85
ACRES
1934
BUILT
"Sensational. That is the one word to describe this English estate nestled off coveted White Oak Lane. Pure elegance woven throughout this timeless brick manor home set on .8 acre breathtaking, impeccable landscaped grounds complemented with English gardens, stone paths, screened in porch & beautifully situated blue stone pool w/separate hot tub. Not one detail has been missed in this graceful & timeless renovation with finely crafted details & designer decor. Expansive first floor plan with a s"
$3,099,000
1070 Fisher Lane, Winnetka IL 60093
5
BEDS
6
BATHS
4,854
SQFT
$638
$/SQFT
0.74
ACRES
1993
BUILT
"Renowned architect Paul Konstant designed and built this exceptional home for himself and has continued to evolve into a showcase home. This wow home sits on 3/4 of a lush and secluded acre on this prestigious East Winnetka lane. While stunning, beautiful & lovely in every way, the home can still live casually; the style and floor plan make this home completely suited for today's living for entertaining, family-life, work-life and more. Gorgeous formal rooms, fantastic social rooms with a wet"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,250,000 TO $3,099,000 
$2,990,000
976 SUNSET Road, Winnetka IL 60093
6
BEDS
9
BATHS
8,800
SQFT
$340
$/SQFT
1.06
ACRES
1961
BUILT
"Sellers are ready to sell this spectacular home on a magnificent, secluded acre! TAXES ARE BEING PROFESSIONALLY CONTESTED AND WILL RESULT IN SUBSTANTIALLY REDUCED TAXES COMMENSURATE WITH THE FINAL SALES PRICE. There is NO greater value on the North Shore than this masterfully renovated and expanded home which is stylish, sophisticated, today, and fabulous in every way. Every amenity is included: 1st & 2nd floor master suites, exercise room, wine room, open floor plan, walls of windows, Chef"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,100,000 TO $2,990,000 
$2,699,000
263 Chestnut Street, Winnetka IL 60093
5
BEDS
8
BATHS
7,500
SQFT
$360
$/SQFT
0.30
ACRES
2015
BUILT
"INCREDIBLE VALUE!!! on this amazing 6BR/7.1 BA masterfully designed, new construction home! Built for the most discriminating buyer! Offering an abundance of space w/ crisp & classic architecture, premiere technology and the finest materials. Features inc: premiere in town location, hand formed brick exterior w/ limestone accents, slate roof, custom mouldings & millwork throughout, specialty lighting, gleaming hardwood floors, oversized windows & french doors, professional landscaping w/ bluesto"
$2,699,000
16 Woodley Road, Winnetka IL 60093
5
BEDS
5
BATHS
1976
BUILT
"This picturesque brick manor set on over an acre of unrivaled & exquisitely landscaped grounds on coveted Woodley has it ALL, having been meticulously updated throughout. Gracious center entry foyer with circular staircase opens to formal living rm w/ enclosed porch, dining rm, and office, all w/ stunning herringbone hardwood floors. Modern kitchen w/ breakfast room & 1,500 bottle wine cellar, sunny family rm w/ double sided fireplace to sun porch, and guest suite complete the 1st floor. Spaciou"
 
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