Winnetka IL Real Estate & Homes for Sale

30 Properties Found

Sort Results:
1–25 of 30 properties displayed
Refine Property Search
Page 1 | 2 of 2    Prev | Next
Beds:
4
Baths:
4.00
Sq.Ft.:
4,064
Status:
NEW LISTING
MLS#:
12688534
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1955
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Set on a professionally landscaped half-acre in the coveted Hubbard Woods School District, this exceptional 4-bedroom, 3.1-bath home offers expansive living spaces, refined finishes, and an effortless floor plan. A gracious foyer opens to an elegant circular layout featuring a sun-filled living room anchored by a striking fireplace, a handsome private office overlooking the landscaped grounds, and a sophisticated dining room with doors opening to the bluestone patio. The inviting family room enjoys picturesque views of the garden-like front lawn and flows seamlessly into the expansive eat-in kitchen, complete with a generous island, high-end appliances, and sweeping views of the lush backyard. A butler's pantry, spacious mudroom, and attached two-car garage complete the thoughtfully designed main level. Upstairs, two luxurious primary suites are complemented by two oversized secondary bedrooms, abundant closet space, and exceptional flexibility. The finished lower level offers a spacious recreation room, dedicated craft studio, and extensive storage. Walk to schools, town, tennis courts and the Winnetka Golf Course!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,717
Status:
NEW LISTING
MLS#:
12687251
Type:
Single Family
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Ideally located in coveted East Winnetka, just moments from Joseph Sears School, Lake Michigan beaches, the Metra train, and New Trier High School's East Campus, this beautifully updated home offers the perfect combination of charm, functionality, and an unbeatable location. Featuring 3 bedrooms, 4 full bathrooms, and a flexible first-floor office or optional 4th bedroom, the home is thoughtfully designed to accommodate a variety of lifestyles. Sun-filled living spaces begin with the elegant formal living room, highlighted by a beautiful bay window, fireplace and new Marvin windows throughout the home. The adjoining dining room flows seamlessly into the expansive eat-in kitchen, creating an ideal setting for both everyday living and entertaining. The inviting family room opens to a charming wraparound porch overlooking the private, fenced backyard, providing the perfect indoor-outdoor connection. A first-floor office or guest bedroom, paired with a full bath, offers exceptional flexibility for remote work, overnight guests, or multigenerational living. The second floor features three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms to comfortably accommodate family and guests. The finished lower level adds valuable living space with a recreation room, playroom, laundry area, and a newly renovated full bathroom. Completing the home are a large mudroom, an oversized detached two-car garage equipped with an electric vehicle charging station, and a spacious driveway. This exceptional residence offers an outstanding opportunity to enjoy East Winnetka living at its finest.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,362
Status:
NEW LISTING
MLS#:
12687072
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1915
A broker reciprocity listing Courtesy: Baird & Warner 773-326-6500
View additional info

ADDITIONAL INFORMATION

Timeless Elegance Meets Modern Luxury with this prime Winnetka home on a large corner lot. Discover the perfect blend of historic character and contemporary living in this meticulously maintained, sun-drenched residence. From the moment you step inside, rich vintage craftsmanship takes center stage, highlighted by striking coffered ceilings, multiple cozy fireplaces, and an exquisite built-in buffet. At the heart of the home is a spectacular chef's kitchen that flows seamlessly into the expansive family room, creating an ideal hub for both daily living and grand entertaining. Retreat to the sprawling primary suite, a private sanctuary complete with a boutique-style walk-in closet, a dedicated sitting room, and an updated bath. The sprawling yard has plenty of room for games and entertaining. Exceptional bonuses include an abundance of storage via the attic and crawl space. The location provides unbeatable North Shore convenience. Step out your front door and walk to top-rated schools, Duke Childs Field, and the vibrant shops and restaurants of Hubbard Woods. The agent is related to the seller.

Beds:
6
Baths:
6.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
12680099
Type:
Single Family
Lot size:
1.5 Acres
Year built:
1937
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-892-4800
View additional info

ADDITIONAL INFORMATION

Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter. co-list Glo Matlin Compass

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
12684635
Type:
Single Family
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Rarely available 2 bed/1 bath condominium in the heart of Hubbard Woods, just steps from the Metra, shops, restaurants, cafes, and Lake Michigan. This beautifully refreshed home features new windows, freshly painted interiors, hardwood floors throughout, an updated bath, and a kitchen with granite countertops and newer stainless steel appliances. A separate dining room offers flexible space for everyday living and entertaining. This move-in-ready home combines timeless charm, thoughtful updates, and an unbeatable walk-to-everything location.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,992
Status:
Active
MLS#:
12657695
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Privately tucked on an extra wide 1/3rd acre property, this fully re-imagined mid-century modern home offers exceptional design and incredible vistas of its lushly landscaped property. Thoughtfully curated with attention to detail and a sophisticated eye for design, the home blends timeless architecture with abundant natural beauty, right in the heart of Winnetka. A super chic, modern kitchen with abundant custom cabinetry and top-tier appliances is anchored by a large island and opens to a stunning dining room with radiant-heated floors and walls of windows beautifully framing panoramic views of the verdant property. The stylized mid-century living room features a contemporary gas fireplace and overlooks the professionally landscaped grounds, perennial gardens, and brick patio. The inviting family room, complete with radiant-heated floors and a second fireplace, offers a warm and stylish gathering place. The luxurious primary suite is a true sanctuary, featuring a private sitting room with built-ins, custom closets, and a spa-inspired bath. Three additional generously sized bedrooms - one ensuite and two sharing a hall bath - provide beautifully appointed modern accommodations for family and guests. The large rec room offers plenty of space for lounging, a work-out area and/or game area, plus a separate laundry room and access to the attached and heated 2-car garage. Every detail of this home has been thoughtfully re-imagined to create effortless indoor-outdoor living. Enjoy an intentional, design-forward home surrounded by beautiful grounds with blooming gardens, and located within easy walking distance to town, schools, parks, the A.C. Nielsen Tennis Center, the Winnetka Golf Club, and the Skokie Lagoons.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,683
Status:
Active
MLS#:
12682485
Type:
Single Family
Lot size:
0.81 Acres
Year built:
1975
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Tucked away in one of Winnetka's most coveted private roads, this exceptional 5-bedroom, 4.5-bathroom estate offers a prime spacious lot surrounded by majestic, mature trees. The property boasts an extraordinary setting that guarantees ultimate privacy while maximizing its unique geographic advantage. The home features dramatic, unobstructed vistas overlooking the historic Indian Hill Golf Course to the south and west, providing a picturesque backdrop of rolling fairways and breathtaking sunset views. Inside, the residence features large, sun-drenched rooms designed for both seamless grand-scale entertaining and comfortable family life. The expansive main living spaces are anchored by large windows that frame the lush greenery, effortlessly bringing the outdoors in. With five generous bedrooms and four and a half baths, the layout offers incredible flexibility for a primary suite retreat, dedicated home offices, or guest accommodation. This is a rare opportunity to own a private oasis with a world-class view in a premier Winnetka location.

Beds:
7
Baths:
13.00
Sq.Ft.:
20,000
Status:
Active
MLS#:
12680920
Type:
Single Family
Subdivision:
East Winnetka
Lot size:
2 Acres
Year built:
2007
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

It's time to unveil the pinnacle of lakefront living in IL, as this newer construction estate is better than brand new construction as it encompasses features that could never be built today with the new lakefront building ordinances. Try to top this...your personal wellness club that is only 20 steps out to your own private, 141-foot wide, sandy beach with indoor pool, sauna, and state-of-the-art gym, to outdoor entertainment space with built-in bluff terrace, 20x40 pool & spa with matching cabana, enclave fire pit, outdoor kitchen and grass tennis court. And the inside...first start from the very top by taking the elevator to the 3rd floor: where guests can have privacy in the in-law suite with a bar, studio, and private patio with panoramic lake views. Hit the 2nd floor with 5 more beds, laundry, and posh master suite with marble bath and jaw dropping lake views, 2 walk-in wardrobe rooms and massive bedroom with fireplace and private patio. Now for the main floor... a dramatic entry with cascading bridal staircase that was made famous with the hit show "Empire" will seem familiar as you step into the reception hallway with 15-foot soaring ceilings. Sun-drenched formal rooms with a stoic mahogany paneled office where deals get done as you step right out the French doors to the pool area. The great room is the perfect viewpoint to capture all the magnificent outdoor fun zones through the floor to ceiling windows with the blues of the lake in the distance. A kitchen that no real chef cannot fall in love with...double islands, endless counter space, all high-end appliances, even a built-in rice maker. The Solarium breakfast room allows for non-depressing meals even on a rainy day and a fabulous sun room with terraced patio for private conversations. Now down to the lower level as there is not one thing missing... theater room, wine room, bar, massive rec room for teenage parties and that secret tunnel to your own wellness wing. Of course, an attached 4-car garage, private gated entrance & motor court drive. No words can really bring this estate to life as only a private tour can bring this living experience to reality. No need to build... as this would cost over $55 million minimum to replicate. Your smartest lakefront investment is now available and even with lake front homes it's still about location, location, location. 319 Sheridan Rd. is the PRIME part of Sheridan Road where two other $30 million plus homes have just closed in the last year as these homes are not high in the bluffs but are in-town estates. Walk to Greeley & New Trier in 10 minutes, ride your bike to town in 5 minutes, jump on the train for a 29 minute ride to the city, and best yet...spend only 3 minutes pulling out your boat from the commercial level boathouse right into the gorgeous waters of Lake Michigan from your own private sandy beach! Private lakefront fun zone...enter at your own risk!

Beds:
7
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
12680669
Type:
Single Family
Lot size:
0.6 Acres
Year built:
1915
A broker reciprocity listing Courtesy: Jameson Sotheby's International Realty 312-751-0300
View additional info

ADDITIONAL INFORMATION

A RARE OPPORTUNITY...in the HEART of East Winnetka, this iconic home is among the Village's most admired residences! Commanding an elevated setting atop Arbor Vitae, the magnificent home was designed by renowned architects Otis & Clark and has earned its grand reputation as Winnetka's own "Castle on the Hill." It boasts one of the most exceptional backyard retreats! Featured in Luxe Magazine and showcased on the prestigious Winnetka Community Housewalk, the home underwent an extraordinary renovation that seamlessly marries historic grandeur with today's most coveted luxury amenities. Every detail has been thoughtfully reimagined while preserving the architectural integrity, craftsmanship and timeless elegance. A breathtaking barrel-vaulted reception gallery sets an unforgettable first impression, creating a dramatic backdrop for art collections, entertaining and everyday living. The home boasts a ton of natural light, soaring ceilings and fabulous millwork. At the heart of the home, a spectacular skylit atrium-style great room offering panoramic views of the sprawling grounds and resort-caliber outdoor living spaces: newly renovated pool, patio, built-in fire pit area and an incredible professionally landscaped backyard. A wall of French doors on the back of the home blends the indoor and outdoor living seamlessly. The designer kitchen is both beautiful and functional, featuring a coveted La Cornue range, Sub-Zero, Miele appliances, custom cabinetry, radiant heated floors and Waterworks fixtures. You will love entertaining in the elegant dining room, sophisticated den with custom bar to the inviting family room anchored by a new fireplace and bespoke built-ins. The luxurious primary suite is a private sanctuary designed for relaxation and renewal. The spa-inspired bath showcases heated marble floors, a steam shower, freestanding soaking tub, Waterworks fixtures and an extraordinary custom dressing room. A private sitting room and office complete the primary suite. Additional renovations include beautifully appointed en-suite baths and a reimagined third floor with hang out, office and workout spaces...use it however you like! Outside, the grounds rival those of a private resort. The expansive, park-like backyard features a stunning renovated swimming pool, multiple entertaining terraces, fire pit, and professionally designed landscaping that provides beauty, privacy, and year-round enjoyment. Easy access to a pool/changing area as well. This home is in an A+ location! Minutes from the Beach, steps from downtown Winnetka shops and restaurants, award winning schools, parks, and the train. This extraordinary family home offers a once-in-a-generation opportunity to own one of Winnetka's true architectural treasures!!

Beds:
6
Baths:
6.00
Sq.Ft.:
4,142
Status:
Active
MLS#:
12670261
Type:
Single Family
Year built:
1895
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Welcome to 757 Locust, a stunning 6-bedroom, 4.2-bath home set on a 15,000-square-foot lot in the heart of Hubbard Woods. Built in 1920 and thoughtfully updated over the years, this exceptional residence blends timeless architecture with modern comfort, exuding character, warmth, and charm at every turn. Large, gracious rooms, soaring ceilings, and oversized windows create a sense of light and space throughout. A bluestone walkway welcomes you to the front entry, where a gracious foyer opens to an oversized living room anchored by a wood-burning fireplace, creating a warm and sophisticated space ideal for both everyday living and entertaining. The well-proportioned dining room flows seamlessly between the living room and kitchen, making gatherings effortless. The kitchen features newer appliances and opens to a sun-filled breakfast room where two walls of windows open wide, beautifully blurring the line between indoors and out. Just off the kitchen, the family room is perfectly positioned, complete with built-ins and a second fireplace, and opens to a deck and patio overlooking the large backyard. A well-placed mudroom connects directly to the deck and backyard. Upstairs, the generous primary suite is a true retreat, featuring a beautifully appointed bath with dual vanity, heated floors, marble throughout, and a walk-in closet. Four additional bedrooms, one with an en-suite bath, and a hall bath complete the second floor. The third floor (by Paul Konstant) offers a sixth bedroom, a full bath, and a charming hangout space with treetop views of Locust Street. The lower level provides space for play and abundant storage. For true peace of mind, this home has been extensively and thoughtfully updated. Recent improvements include two new AC condensers (2026), a new AC air handler (2026), an EV charging port (2025), a new composite synthetic cedar roof (2024), fresh exterior paint (2024), replaced water service (2023), new sump pumps (2023), a combined boiler/hot water heater installed by American Vintage Home, and numerous other updates throughout. The heated, attached, oversized garage adds everyday convenience year-round. A truly special opportunity to own a timeless Winnetka home just moments from Lake Michigan, the Hubbard Woods and Elm Street shopping districts, parks, beaches, schools, and the train. North Shore living at its finest.

Beds:
5
Baths:
5.00
Sq.Ft.:
6,900
Status:
Active
MLS#:
12677019
Type:
Single Family
Lot size:
0.33 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Compass 847-416-0446
View additional info

ADDITIONAL INFORMATION

Nestled in one of the most sought-after and convenient locations in Winnetka/Hubbard Woods, this exceptional stone residence blends timeless architecture, refined design, and modern comfort just moments from town, the train, and Lake Michigan. Expertly crafted in 2006 by Adamczyk Fine Homes and Interiors, the home showcases nearly 7,000 square feet of beautifully designed living space across three finished levels. A grand foyer with a stunning custom staircase welcomes you into elegant, light-filled interiors, including a gracious living room with fireplace and a richly paneled private office. Designed for both everyday living and sophisticated entertaining, the formal dining room features its own fireplace and an adjoining butler's pantry complete with wine and beverage refrigerators. At the heart of the home is a family friendly gourmet kitchen with an island, abundant workspace, and a sunny breakfast area that opens seamlessly to the inviting family room. Custom built-ins, a fireplace, and French doors create a warm and comfortable setting while offering effortless access to the bluestone patio and expansive fenced backyard. The thoughtfully designed mudroom and laundry area provide everyday functionality with direct access to the attached two-car garage. Upstairs, the luxurious primary suite serves as a private retreat with a spacious bath and dual walk-in closets. Four additional generously sized bedrooms provide flexibility for family and guests, including a versatile fifth bedroom that can easily function as a sitting room, office, or exceptional dressing room extension to the primary suite. Two additional full baths complete the second level. The impressive lower level offers high ceilings, natural daylight windows and exceptional versatility, featuring a stone wine room, multiple recreation spaces, a sixth bedroom with full bath, exercise room, and storage. Outside, beautifully landscaped grounds create a serene and private setting that complements the home's elegant character. With exceptional craftsmanship, quality materials, a flowing floor plan, and timeless appeal, this remarkable property offers luxurious living designed for generations to enjoy. *Some photos virtually staged* Recent updates include a new Brava synthetic composite roof (2022), two new air conditioning systems (2022 & 2020), and a new furnace (2023).

Beds:
2
Baths:
2.00
Sq.Ft.:
1,360
Status:
Active
MLS#:
12676299
Type:
Single Family
Year built:
1971
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Sun-drenched mornings define this coveted two-bedroom, two-bathroom residence. Located in a premier building within a highly sought-after location, this home welcomes you with a bright, cheerful, thoughtful layout. The east-facing exposure ensures the living spaces are bathed in natural light, while the charming private balcony offers the perfect spot for a morning coffee or an evening breeze. The spacious living and dining rooms, anchored by classic hardwood floors, create an inviting backdrop for both daily relaxation and lively entertaining. Nearby, the well-appointed galley kitchen strikes a balance between style and utility, offering plentiful storage and a convenient pass-through for effortless serving. The primary suite serves as a private retreat, complete with a dedicated primary bath and ample closet space. A second full bath is located off the hallway, easily accessible for guests. Currently, the second bedroom has been reimagined as a cozy den adjacent to the main living area, offering a flexible layout to suit your needs. Beyond the main living quarters, the building offers exceptional amenities, including fabulous party room featuring a kitchenette and a half bath, all overlooking the pool and patio. This is a smoke free building. One dog (20lb. wt. limit) or one cat is allowed.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,938
Status:
Active
MLS#:
12671135
Type:
Single Family
Year built:
1954
A broker reciprocity listing Courtesy: Jameson Sotheby's International Realty 847-869-7300
View additional info

ADDITIONAL INFORMATION

Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning fireplace, an expansive updated kitchen with abundant cabinetry, and a dining area flanked by windows with plantation shutters. A bonus family room with vaulted ceilings and skylights, along with a full bathroom, adds valuable flexibility and completes the main level. Upstairs, you'll find two bedrooms with hardwood floors and a shared hall bath. The finished basement offers even more living space, featuring a second fireplace, a wall of closets, and a utility room with additional storage. Step outside to a picturesque, professionally landscaped garden with two patios and plenty of space for relaxing or entertaining. From its inviting curb appeal to its surprisingly spacious interior, this home strikes the perfect balance between charm and function. Timeless details and thoughtful updates are complimented by a versatile layout designed for comfortable everyday living and effortless entertaining.

Beds:
5
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
12674124
Type:
Single Family
Lot size:
0.4 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Easy living at its best! Discerning updates and renovations combine with impeccable maintenance to create this exceptional home with the ease of one-floor living with outstanding design, gracious proportions, and an effortless flow throughout. Set on a gorgeous 4/10 acre property, the grounds are a true private retreat, featuring lush, professional landscaping, mature trees, colorful plantings, expansive lawns, elegant patio and front entrance, and thoughtfully designed landscape lighting that creates a magical setting day and night. A welcoming foyer introduces the inviting interior, where sun-filled living spaces are perfectly suited for both everyday living and entertaining. The spacious living room, elegant dining room, gourmet kitchen, and large family room blend seamlessly together, creating an ideal layout for today's lifestyle. The home offers five+ generously sized bedrooms including a luxurious primary suite that serves as a peaceful sanctuary and 4 additional bedrooms (3 are ensuite). The spa-inspired primary bath features heated floors and refined finishes, creating the perfect place to prepare for the day or to unwind at night. The finished lower level adds exceptional versatility with two spacious recreation and living areas, an exercise area, office/bedroom, full bath and abundant storage. A spacious, bright mudroom is accessed from the heated attached garage (with epoxy floor), and the adjacent laundry room provides everyday convenience and functionality. Originally renovated in 2001 and thoughtfully enhanced with significant updates in 2010 and then a fabulous renovation/updates in 2022, this home combines a fresh, current aesthetic with modern comfort. An extraordinary opportunity to enjoy easy, elegant living in one of the area's most beautiful and sought-after neighborhoods.

Beds:
4
Baths:
6.00
Sq.Ft.:
4,225
Status:
Active
MLS#:
12673083
Type:
Single Family
Year built:
1965
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-374-0200
View additional info

ADDITIONAL INFORMATION

Rarely available unique mid-century contemporary in the heart of Winnetka. Your own private paradise with a flowing interior perfect for entertaining! Soaring teak ceilings add to the Aspen style influence. Tons of windows look out to the gorgeous landscaped grounds enhanced by a pool and gazebo. This home has been beautifully maintained by the current owners.

Beds:
6
Baths:
9.00
Sq.Ft.:
10,588
Status:
Active
MLS#:
12661112
Type:
Single Family
Lot size:
1.25 Acres
Year built:
1929
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

An extraordinary "boutique hotel" living experience, impeccably situated in the heart of Winnetka. Beyond a stately solid-iron gate adorned with gold medallion accents lies a private sanctuary just 18 miles from Chicago and less than half a mile from the sandy shores of Lake Michigan. Evoking the glamour and grandeur of a Roaring Twenties estate, this remarkable residence channels the elegance of The Great Gatsby era with five-star refinement at every turn. A dramatic foyer welcomes you with gleaming marble floors and a sweeping bridal staircase crowned by intricate wrought-iron railings, all illuminated by a stunning domed Art Deco skylight overhead. The main level unfolds with gracious formal rooms designed for both grand entertaining and effortless flow. An elegantly appointed dining room transitions seamlessly into a spectacular chef's kitchen, where a striking black-and-white palette of stone and texture creates a timeless aesthetic. Top-tier appliances-including a side-by-side Sub-Zero glass-door refrigerator and freezer-complement a bespoke upholstered dining banquette, offering a restaurant-caliber culinary experience at home. Thoughtfully designed corridors and private retreats provide space for both gathering and solitude. A finely finished office of magazine-worthy distinction, a warm and inviting family room with an 80-inch television and custom lacquered walls, a first-floor laundry room, guest suite with full bath, and a fully equipped mudroom enhance everyday living. The heated four-car garage wing is a masterpiece in itself, featuring epoxy floors, custom cabinetry, and stone countertops-an exceptional showcase for the discerning automotive collector. Upstairs, an expansive second level hosts a primary suite truly fit for royalty. A serene sitting room with a fireplace precedes a breathtaking onyx bath with dual custom vanities and a commercial-grade steam shower complete with body sprays and a rain head. Bathed in natural light, the craftsmanship and stonework must be experienced to be fully appreciated. Four additional bedrooms, each with pristine white-stone en-suite baths, provide luxurious accommodations for family and guests. An exercise studio with a dedicated yoga retreat, adorned in palm-inspired wall coverings, offers a tranquil escape for wellness and balance. The fully finished lower level features a kitchenette, bath, wine room, and expansive entertainment spaces designed for comfort and leisure. Outdoors, enchanting terraces, sun-drenched patios, and winding pathways create a private oasis ideal for alfresco dining and elegant gatherings. Meticulously renovated with no expense spared and exquisitely furnished to celebrate its Art Deco heritage, this residence offers a rare opportunity that feels more akin to a world-class luxury hotel than a private home.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,364
Status:
Active
MLS#:
12629591
Type:
Single Family
Lot size:
0.27 Acres
Year built:
1937
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

They don't build them like this anymore, but they should! This solidly built custom Hemphill home is ideally located in sought-after East Winnetka and offers timeless character, quality craftsmanship, and thoughtful updates. Built in 1936 with exceptional materials and lovingly maintained by only two owners, this home combines classic elegance with modern comfort. The spacious living room features decorative plaster crown molding, a gas-log fireplace, and built-in cabinetry, while the formal dining room showcases equally impressive molding and elegant wainscoting. The kitchen is appointed with high-end appliances, beautiful wood cabinetry, granite countertops, and an eating area. A welcoming family room overlooks the expansive fenced backyard and slate patio. Upstairs, four generously sized bedrooms each offer walk-in closets. The second level also includes an updated primary bath, a hall bath, and an en-suite bath, along with a large cedar closet and a deck overlooking the backyard. The basement offers exceptional additional space with four separate rooms: a recreation room with wood-burning fireplace, a work/hobby room, a "canning"/storage room, and a utility area with laundry. Direct access to the oversized attached two-car garage adds convenience. Set on a wide lot, 478 Sunset offers a wonderful floor plan just a few blocks from parks, schools, beaches, the train, and more.

Beds:
3
Baths:
3.00
Sq.Ft.:
4,356
Status:
Active
MLS#:
12668394
Type:
Single Family
Lot size:
0.53 Acres
Year built:
1953
A broker reciprocity listing Courtesy: @properties Commercial 312-337-0200
View additional info

ADDITIONAL INFORMATION

Beds:
5
Baths:
9.00
Sq.Ft.:
7,480
Status:
Active
MLS#:
12657418
Type:
Single Family
Year built:
2003
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Beds:
6
Baths:
8.00
Sq.Ft.:
8,303
Status:
Active
MLS#:
12660928
Type:
Single Family
Lot size:
0.52 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Coldwell Banker Realty 847-446-4000
View additional info

ADDITIONAL INFORMATION

Nestled on a private lane east of Sheridan Road, this distinguished Winnetka residence offers privacy, scale, quality craftsmanship, and exceptional everyday livability in one of the North Shore's most coveted east-side locations. Designed for elegant entertaining, multigenerational living, work-from-home flexibility, and relaxed daily comfort, the home features 6+ bedrooms, including a private in-law/guest suite with kitchen, 7.1 baths, expansive gathering spaces, an outdoor pool and spa, home theater, exercise room, and beautifully landscaped grounds. A sunlit two-story foyer with a sweeping bridal staircase creates a memorable first impression, opening to gracious formal living and dining rooms, a richly appointed library/home office, and a dramatic great room with coffered ceilings and wet bar. The chef's kitchen is beautifully equipped for everyday meals, holiday hosting, and large-scale entertaining, with a substantial center island, white cabinetry, professional gas range, double wall ovens, two dishwashers, full-size refrigerator and freezer, beverage refrigerator, and built-in microwave. Just beyond the kitchen, a comfortable fireside family room offers space for casual dining and opens to a lovely patio overlooking the private, professionally landscaped setting. A large mudroom with a full bath provides practical convenience and easy access for pool and spa use. Upstairs, the serene primary suite features three walk-in closets and a luxurious bath with steam shower and generous vanity space. The second level also includes two additional en-suite bedrooms, a full guest/in-law suite with kitchen, two more bedrooms, a hall bath, and a skylit laundry room - offering exceptional flexibility for guests, extended stays, private living space, or household support. The finished lower level expands the home's lifestyle appeal with a home theater, game room, exercise room/gym, bedroom with full bath, bonus room, and abundant storage. Additional amenities include: heated garage, heated driveway, sprinkler system, exterior lighting, and manicured professional landscaping. Located within the sought-after New Trier High School district and near beloved Hubbard Woods amenities, this private east Winnetka estate offers space, sophistication, resort-style amenities, and close proximity to Lake Michigan, beaches, parks, shopping, dining, and transportation - an extraordinary opportunity in one of Winnetka's most desirable locations. Property is being offered AS IS.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,837
Status:
Active
MLS#:
12640779
Type:
Single Family
Year built:
2015
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Nestled on a charming, quiet, tree-lined street in Winnetka's highly sought-after Hubbard Woods neighborhood, 1482 Edgewood Lane offers the perfect blend of timeless style, modern functionality, and an unbeatable North Shore location-just steps from Nick Corwin Park, and less than a mile to town, train, and schools. Built in 2015, this stunning Nantucket-inspired newer construction home is beautifully maintained and thoughtfully designed with today's buyer in mind. Offering 6 bedrooms, 5.1 baths, and exceptional living space across four finished levels, this home truly has it all. A gracious foyer welcomes you inside, where hardwood floors, classic millwork, and abundant natural light set the tone throughout. The heart of the home is the gorgeous white chef's kitchen, which opens seamlessly to the inviting family room featuring coffered ceilings, built-ins, and access to the extra-deep (50' x 200') backyard - perfect for everyday living and entertaining alike. The main level also includes a handsome office with custom built-ins, elegant dining room, charming sitting room, and an ideal mudroom that connects to the attached two-car garage. The second floor features four spacious bedrooms and three full bathrooms, including a luxurious primary suite with soaring ceilings and a spa-like bath complete with heated floors, dual vanities, soaking tub, oversized walk-in shower, and two walk-in closets. The finished third floor offers incredible flexibility with a private bedroom suite and full bath-ideal as a guest retreat, office, or playroom. The lower level is equally impressive, featuring exceptional ceiling height, an enormous recreation room, wet bar, gym, sixth bedroom, and an additional full bath. Beautifully updated and impeccably maintained throughout, 1482 Edgewood Lane checks every box in one of Winnetka's most beloved neighborhoods. A truly special home in an idyllic setting.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,680
Status:
Active
MLS#:
12604512
Type:
Single Family
Year built:
1929
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Nestled in the heart of Winnetka's coveted " TREE STREETS" neighborhood sits the storybook home you've been waiting for. This special home is a sun-filled Mediterranean villa with an effortless blend of timeless architecture and a fresh, coastal-inspired aesthetic throughout. The home showcases airy interiors, soft neutral tones, and a well appointed floor plan that perfectly suits today's lifestyle. The great room has soaring ceilings, white washed wood beams, windows overlooking the park and a cozy gas fireplace. The bright white kitchen has high end appliances and beautiful marble countertops. The dining room is conveniently located adjacent to the kitchen. The first floor primary suite was recently expanded to create a spacious beautiful space. Equipped with a spa-like bathroom and large walk-in closet. The second floor has a bright landing desk/reading area, two large bedrooms connected by a beautiful bathroom, as well as a sun-filled bonus tandem room overlooking the gorgeous yard. The finished basement is currently being used as a music room but can easily be whatever you desire for the space. The tranquil oversized backyard is a peaceful place to retreat. Lush and green with a large bluestone patio, fire-pit and grill area, all with perfect views of the Fourth of July fireworks! Enjoy easy living with the premier walk-to location-just steps to award winning schools K-8, tennis, paddle, golf, sports fields, town + train and a short walk to the beach. Drop your bags & enjoy!!

Beds:
6
Baths:
6.00
Sq.Ft.:
7,000
Status:
Active
MLS#:
12637769
Type:
Single Family
Lot size:
1.55 Acres
Year built:
1933
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as the land value alone is worth at least $2 million dollars. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet a dramatic double atrium staircase wrapped in elegant wrought iron setting the tone for the architectural beauty that unfolds throughout. Gracious comfort exudes throughout this 13 room estate with that desirable southern exposure that allows natural sunlight to flood through the endless windows outlining the incredible backyard. Step down to a beautiful formal living room with a stone Parisian FP & custom French doors that open up to the cozy sunroom with picturesque windows overlooking the backyard. Finely appointed dining room with Visual Comfort light fixture layered with de Gournay wallpaper, antique marble fireplace and another set of French doors open out to the bluestone patio and deep backyard. Finely crafted white Chef's kitchen by O'Brien Harris with Villa Blanca marble, Clark & Barlow hardware, antique mirrored backslash and Holly Hunt pendents. Seamless transition to family rm ideal for cooking and entertaining at the same time. Command center mudroom, 2 powder rooms, and brand new laundry room also on this level. Two staircases lead the way up to large 2nd floor with intimate "Ralph Lauren" inspired den richly finished in restored paneled chestnut walls & handsome built-ins w/ dark marble FP. Large primary suite with room for even more expansion over porch is completed with Ann Sacks white bath and gracious marble FP with custom built-ins accented by a built-in window bench. 3 additional bedrooms with one being a large family bedroom w/ en-suite bath. The other 2 beds share pretty all white redone bathroom. Up to the oversized fully finished 3rd floor with 2nd family room and 2 beds ideal for in-law quarters or nanny. Lower level with mechanicals and ample storage space. The vibe of this home is effortlessly inviting-warm, layered, and livable across all 3 finished levels, seamlessly blending indoor & outdoor living. And with ample space to add a pool, the vision of true Southern comfort could be fully realized, elevating this already timeless retreat into a personal resort unlike any other.

Beds:
5
Baths:
9.00
Sq.Ft.:
6,950
Status:
Active
MLS#:
12606067
Type:
Single Family
Lot size:
0.5 Acres
Year built:
2006
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 312-682-8500
View additional info

ADDITIONAL INFORMATION

Beds:
6
Baths:
10.00
Sq.Ft.:
15,000
Status:
Active
MLS#:
12600188
Type:
Single Family
Lot size:
0.93 Acres
A broker reciprocity listing Courtesy: Village Realty Group Inc 847-251-5714
View additional info

ADDITIONAL INFORMATION

A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value privacy, wellness, and architectural presence-without compromise. Designed with a timeless, classic architectural aesthetic and infused with modern innovation for 2026 living, this residence delivers true first-floor living and entertaining with every amenity required for builders "Five Star Living Every Day". The main floor estate amenities feature builders signature 50-foot art gallery with museum-quality lighting, a spectacular kitchen connected to outdoor entertaining, a 60-foot in-ground pool, dining capacity for 30, dine-in wine cellar, billiards and bar lounge, home theater, golf and sports simulator room, private office and den, wellness center with steam, sauna, whirlpool spa, cold plunge, massage room, and fitness center, and a luxurious primary suite, all on the main level. Situated on a rare one-acre lot in the coveted Crow Island School District, the 3 stop elevator to the second floor offers four ensuite guest bedrooms, with additional guest accommodations and extensive storage on the 10' ceilings lower level. Extensive landscaping and heated outdoor living spaces for entertainment and pool and outdoor spa fun complete this unique opportunity. Offered at $16,900,000. Serious inquiries only

Refine Property Search
Page 1 | 2 of 2    Prev | Next
1–25 of 30 properties displayed
Andrea D. Conner, License 471020674, Xome Inc., License 478026347, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


© 2026 Midwest Real Estate Data LLC. All rights reserved. Listings courtesy of MRED MLS as distributed by MLS GRID, based on information submitted to the MLS GRID as of {{last updated}}.. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to [email protected]. The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.



Winnetka Real Estate

Winnetka is located in Illinois. Winnetka, Illinois has a population of 12,658. Winnetka is more family-centric than the surrounding county with 48.66% of the households containing married families with children. The county average for households married with children is 29.73%.

The median household income in Winnetka, Illinois is $250,001. The median household income for the surrounding county is $72,121 compared to the national median of $69,021. The median age of people living in Winnetka is 42.6 years.

Winnetka Weather

The average high temperature in July is 83.1 degrees, with an average low temperature in January of 16.7 degrees. The average rainfall is approximately 36.4 inches per year, with 35.9 inches of snow per year.

Winnetka Map

Winnetka Real Estate Market Conditions

  • Median sales price

    $1,932,504
    14.5%
    change since last quarter
  • # Active listings

    31
    30-day change

Winnetka Schools and Demographics

Education near Winnetka, IL

City County
High School Graduates 99.05 87.97
College Degree - 2 year 1.95 6.73
College Degree - 4 year 90.39 40.75
Graduate Degree 32.62 12.01
Expenditures per Student 21,907 21,907
Students per Teacher 14 14

Elementary Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
Avoca West Elementary School KG - 05 446 9.7 60025
Central Elementary School KG - 04 507 13.8 60091
Crow Island Elementary School KG - 04 391 12.2 60093
Glen Grove Elementary School 03 - 05 530 14.1 60025
Greeley Elementary School PK - 04 276 10.9 60093
Harper Elementary School KG - 04 428 15.1 60091
Henking Elementary School PK - 02 483 12.9 60025
Hoffman Elementary School 03 - 05 599 15.1 60025
Hubbard Woods Elementary School KG - 04 249 9.7 60093
Lyon Elementary School PK - 02 476 15.2 60025
McKenzie Elementary School KG - 04 512 14.9 60091
Middlefork Primary School PK - 03 203 11.8 60093
Pleasant Ridge Elementary School 03 - 05 549 15 60025
Romona Elementary School PK - 04 518 13.8 60091
South Elementary School KG - 02 352 13.5 60022
The Joseph Sears School PK - 08 495 8.7 60043
Washington Elementary School PK - 06 303 11.2 60025
West School 03 - 04 258 12.6 60022

Middle Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
Carleton W Washburne School 07 - 08 440 10.4 60093
Central School 05 - 08 589 10.1 60022
Highcrest Middle School 05 - 06 841 12.8 60091
Marie Murphy School 06 - 08 261 9.3 60091
Springman Middle School 06 - 08 854 13.9 60025
Sunset Ridge Elementary School 04 - 08 279 8.6 60093
The Skokie School 05 - 06 439 11.1 60093
Wilmette Junior High School 07 - 08 884 12.3 60091

High Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
New Trier Township H S Winnetka 10 - 12 3,086 11.6 60093

Ungraded Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
New Trier Township H S Northfield 09 - 09 971 11 60093

Demographics near Winnetka, IL

City County
Neighborhood Type Suburban
Population 12,658 5,265,398
Population Density 3,325 5,572
Median Age 42.6 37.3
People per Household 2.9 2.5
Median Household Income 250,001 72,121
Average Income per Capita 143,109 41,706

Real estate near Winnetka