Winnetka Real Estate, Homes and Condos for sale

All Winnetka homes currently listed for sale in Winnetka as of 03/23/2019 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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$8,995,000
203 Sheridan Road, Winnetka IL 60093
4
BEDS
4.1
BATHS
1.10
ACRES
1926
BUILT
"This is your chance to own one of Winnetka's rarely available private beachfront properties. Situated on over an acre, this impressive property boasts a glorious set-back from Sheridan Road and is one of the few through lots to Lake Michigan. Perfectly sized for easy living, this home has old-world hand craftsmanship of solid stone, brick and slate materials. Highlights include a floor plan that offers sunlit and spacious room sizes with direct lake views. Conveniently located from both downt"
$7,999,999
1215 Whitebridge Hill Road, Winnetka IL 60093
6
BEDS
6.4
BATHS
15,000
SQFT
$533
$/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 - $8,200,000 TO $7,999,999 
$6,245,000
738 Tower Road, Winnetka IL 60093
6
BEDS
8.3
BATHS
7,122
SQFT
$877
$/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"
$4,999,000
480 Oak Street, Winnetka IL 60093
5
BEDS
5.1
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"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $5,195,000 TO $4,999,000 
$4,995,000
919 HILL Road, Winnetka IL 60093
6
BEDS
7.2
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
8.2
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"
$4,500,000
165 Thorntree Lane, Winnetka IL 60093
6
BEDS
6.3
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
6.2
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"
$4,295,000
630 Rosewood Avenue, Winnetka IL 60093
5
BEDS
6.2
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."
$3,995,000
861 Bryant Avenue, Winnetka IL 60093
6
BEDS
7.2
BATHS
7,965
SQFT
$502
$/SQFT
0.57
ACRES
2018
BUILT
"Stately Stucco/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. Scheduled completion March 2019. 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 to formal Living Room, "
* LISTED OVER 120 DAYS 
$3,850,000
30 Indian Hill Road, Winnetka IL 60093
6
BEDS
5.3
BATHS
10,000
SQFT
$385
$/SQFT
1.28
ACRES
1920
BUILT
"A true gem! This extremely rare offering is full of impeccable charm & discreet grandeur! The gracious residence & private family retreat sits on 1.3 pristine acres overlooking the 6th fairway of Indian Hill Club golf course. No detail was overlooked during the recent updating of this 1920's private treasure. The drama of the expansive sunlit rooms is made even more appealing by all the serene southern exposure views of the grounds. As you approach this crisp, stately Colonial home, you're welco"
$3,795,000
790 Prospect Avenue, Winnetka IL 60093
6
BEDS
6.2
BATHS
6,000
SQFT
$632
$/SQFT
0.40
ACRES
2019
BUILT
"Another outstanding house in Winnetka! App. 9,000 sq.ft of finished space with 6 Bedrooms & 6.2 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 owned/interest."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,875,000 TO $3,795,000 
$3,585,000
1137 Laurel Avenue, Winnetka IL 60093
5
BEDS
6.1
BATHS
8,323
SQFT
$431
$/SQFT
0.33
ACRES
2018
BUILT
"Winning combination: one of Winnetka's prettiest curvy tree-lined streets with Dyamite new construction make this home one of a kind! Approx. 8400 sf of finished space on all 4 levels. All luxury high-end finishes, with the latest in design and technology. Slate Roof; Copper Gutters. Stone Exterior on all four sides. Chef s kitchen with top of the line appliances, custom built library, 1st FLOOR BEDROOM with MARBLE BATH. 3 car attached garage. Lower level with media, wine cellar,wet bar, bedro"
* LISTED OVER 120 DAYS 
$3,500,000
58 Woodley Road, Winnetka IL 60093
7
BEDS
8.4
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, "
$3,495,000
115 Mary Street, Winnetka IL 60093
5
BEDS
4.1
BATHS
4,482
SQFT
$780
$/SQFT
1908
BUILT
"Vacation year round on your private beach with cottage and pool on one acre plus property. At the end of the cul-de-sac sits a gracious home, extensive lawn, picturesque pool and wooded private property to the beach. Stunning 5 bedrooms 4.1 bath home and 1 bedroom 1 bath cottage with stellar views of Lake Michigan and bluff. Terraced flagstone entrance into a 4 season porch w/abundant light and traditional living spaces. Serene living room and dining room have pristine oak floors, fireplace, and"
* NEW LISTING 
$3,475,000
966 Pine Tree Lane, Winnetka IL 60093
5
BEDS
6.2
BATHS
6,800
SQFT
$511
$/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."
* PRICE LOWERED - $3,575,000 TO $3,475,000 
$3,450,000
644 Pine Lane, Winnetka IL 60093
6
BEDS
5.1
BATHS
2.39
ACRES
1928
BUILT
"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. NO PART IS IN THE FLOOD PLAIN. THE HOUSE ITSELF IS THE PERSONIFICATION OF CHARMING. INVITING, WARM, APPEALING ARE OTHER APPROPRIATE ADJECTIVES! KNOTTY PINE PAN"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,850,000 TO $3,450,000 
$3,400,000
6 Kent Road, Winnetka IL 60093
5
BEDS
5.2
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
560 OAK Street, Winnetka IL 60093
5
BEDS
5.1
BATHS
4,900
SQFT
$689
$/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 - $3,425,000 TO $3,375,000 
$3,350,000
1363 Hackberry Lane, Winnetka IL 60093
5
BEDS
5.1
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"
$3,295,000
310 Myrtle Street, Winnetka IL 60093
5
BEDS
5.2
BATHS
7,500
SQFT
$439
$/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"
$3,245,000
139 De Windt Road, Winnetka IL 60093
6
BEDS
5.3
BATHS
6,203
SQFT
$523
$/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 "
$3,195,000
987 Asbury Court, Winnetka IL 60093
5
BEDS
5.1
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 
$2,999,999
1314 TRAPP Lane, Winnetka IL 60093
5
BEDS
6.3
BATHS
11,500
SQFT
$261
$/SQFT
0.62
ACRES
2003
BUILT
"Priced to sell! Masterful design & timeless elegance await you in this luxury Tudor manor home situated in a prime area of Winnetka. Coffered ceilings, hardwood floors, intricate millwork & custom crown molding are just a few of the finest details throughout. Double door entry greets you into the foyer offering a grand cascading staircase, stone flooring & open concept views into the formal living & dining rooms. Top-of-the-line kitchen boasts granite counters, custom cabinetry, herringbone back"
 
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