Winnetka Real Estate

Welcome to Winnetka, a charming village located in Cook County, Illinois. Known for its picturesque neighborhoods, top-rated schools, and beautiful parks, Winnetka offers a serene suburban lifestyle just a short drive away from the bustling city of Chicago.

Winnetka is a highly sought-after community for families looking to settle down in a safe and welcoming environment. The village is home to a vibrant downtown area filled with boutique shops, cozy cafes, and delicious restaurants. Residents can enjoy a variety of recreational activities, from hiking and biking along the Lake Michigan shoreline to playing a round of golf at one of the local country clubs.

With its tree-lined streets, historic homes, and strong sense of community, Winnetka embodies classic Midwestern charm. The village hosts a range of community events and festivals throughout the year, bringing neighbors together and creating a tight-knit community spirit.

For those seeking a peaceful retreat from the hustle and bustle of city life, Winnetka offers the perfect blend of small-town charm and modern amenities. Come explore all that this vibrant village has to offer and discover why Winnetka is a place that so many are proud to call home.

Newest Listings in Winnetka

$2,000,000

4 Beds ⋅ 5 Baths ⋅ 12751307 MLS ⋅ NEW Status

A rare expression of extraordinary North Shore living, this quintessential red-brick Colonial sits on a 100' x 175' double lot (.39 of an acre) on coveted Hill Terrace, one of Winnetka's prettiest private lanes, in an A+ walk-to-everything location. Designed by prolific architect Bertram A. Weber, this much-loved residence has been completely reimagined by its current owners, who've seamlessly married classic architecture with sophisticated, thoughtful updates (new Visual Comfort and Restoration Hardware lighting fixtures, new hardwood floors, new recessed lighting, new Emtek door hardware, new Sonos system, and new Graber custom window treatments, to name a few). A welcoming foyer with rich architectural moldings leads to the light-filled living room with gas fireplace and adjacent formal dining room. Cook's kitchen has Calacatta marble countertops, Sub-Zero paneled fridge and upgraded stainless steel appliances. The spacious family room boasts a wall of built-ins, two walls of windows, and a wet bar with GE Cafe refrigerator. Modernized attached screened porch and mudroom overlook the lush, professionally landscaped backyard with multiple patios, new oversized composite deck, newly expanded paver patio and walkway, new cedar fence, and vegetable garden with raised beds. A home office with a view and updated powder room complete the first floor. Upstairs, the serene primary suite has a walk-in and two additional closets leading to an oversized bath with cathedral ceilings, Jacuzzi tub, shower, and dual vanities. At the other end of the floor, the most incredible junior suite offers the versatility of a second primary, complete with walk-in closet, remodeled bath with dual vanities, and a private back staircase to the family room below. Two more bedrooms share a new RH hall bath. The finished lower level has a recreation room, exercise area, new bedroom, laundry room with new LG washer and dryer, full bath (expanded from half) and private entrance with ADT Bluetooth lock. The detached two-plus-car garage includes a dedicated shed/storage area and walk-up attic. Dual-zone heating and air conditioning, irrigation system and new exterior lighting. With just eight residences, Hill Terrace has a hidden-away, private cul-de-sac like setting, yet it's steps from the Green Bay Trail, top-rated schools (New Trier, Greeley Elementary, Faith, Hope and Charity, and North Shore Country Day all less than half a mile away), parks, lake, town and train, making 579 a True Treasure in the Heart of Winnetka!

579 Hill Terrace, Winnetka

$899,000

3 Beds ⋅ 2 Baths ⋅ 12743165 MLS ⋅ RE-ACTIVATED Status

A rare opportunity on one of Winnetka's most beloved neighborhood streets. Welcome to 790 Foxdale Avenue, a charming Dutch Colonial offering timeless character, a wonderful sense of community and an exceptional location in the sought-after Greeley Elementary attendance area and New Trier High School district. Foxdale is more than just a beautiful tree-lined street-it's the kind of block where neighbors know one another, kids are often outside playing and spontaneous conversations happen at the end of the driveway. Longtime neighborhood traditions have included Flamingo Fridays, block parties and even a "Foxdale Float" in Winnetka's Fourth of July Parade. It's vibrant, welcoming and the kind of street that inspires people to say, "Foxdale-that's a fun block." This well taken care of home offers classic curb appeal with durable, low-maintenance composite siding and a newly fenced backyard. Step inside to hardwood floors, original architectural details and a surprisingly generous entry coat closet. The spacious living room features a marble fireplace with flanking built-ins, while the formal dining room flows into the kitchen with white cabinetry, stainless steel appliances and a charming breakfast nook overlooking the backyard-a perfect spot for morning coffee, casual meals or homework. Upstairs are three bedrooms, a full bath and a versatile bonus room adjoining one of the bedrooms. Currently used as a home office, this flexible space could also make a wonderful playroom, sitting room, nursery or creative retreat. The finished lower level provides additional recreation space, laundry and a workshop, while a playful hidden wine nook tucked along the stairway adds an unexpected bit of character. Outside, the private newly fenced backyard features a brick paver patio and built-in fire pit, creating an inviting setting for dining, entertaining and play. A two-car garage completes the property. Beautifully maintained and inviting as it stands, the home is also an ideal canvas for a buyer to add their own finishing touches and thoughtful cosmetic updates over time. Ideally located near downtown Winnetka, Hubbard Woods, Metra, the Green Bay Trail, parks, beaches and everything the village has to offer, 790 Foxdale presents an increasingly rare opportunity to enjoy a classic Winnetka home on a street known as much for its community as its location. Select images have been AI-rendered to help illustrate the home's amazing potential with cosmetic enhancements and are intended for visualization purposes only. Buyers and agents to verify all finishes and dimensions in person.

790 Foxdale Avenue, Winnetka

$1,350,000

4 Beds ⋅ 3 Baths ⋅ 12732812 MLS ⋅ ACTIVE Status ⋅ Winnetka Mews BLDG.

Be prepared to be impressed by this rarely available, beautifully updated top-floor 4 bedroom, 3 bath residence in the historic Winnetka Mews, perfectly positioned with a Pine Street exposure. Thoughtfully renovated with exceptional attention to detail, this sun drenched home combines gracious living spaces, timeless finishes and an abundance of thoughtfully designed storage. At the heart of the home is a stunning chef's kitchen featuring custom cabinetry, a Wolf convection oven, Sub-Zero refrigerator, beverage refrigerator and striking granite countertops imported from India. The expansive living and dining rooms flow seamlessly together, creating an ideal setting for both everyday living and effortless entertaining. A custom marble fireplace anchors the space, while an exquisite chandelier imported from Sweden adds a distinctive finishing touch. The fourth bedroom is currently designed as an inviting library with custom built-in bookcases, offering wonderful flexibility as a home office, den or bedroom. The desirable Pine Street exposure fills the residence with natural light and offers peaceful treetop views along with a wonderful sense of privacy. All three bathrooms have been beautifully updated with Italian Carrara tile, medicine cabinets and RH plumbing fixtures. A feature rarely found in condominium living, is the custom mudroom with built-in lockers, providing additional storage and organization. Rich hardwood flooring extends throughout the main living spaces, while luxurious carpeting adds warmth and comfort to the bedrooms. Custom closets throughout further enhance the home's impressive storage. With four bedrooms, three full baths, generous entertaining spaces and a premier top-floor location, this is a rare opportunity to "right size" without compromise. Enjoy the space, quality and thoughtful design of a single-family home paired with the ease of condominium living, all just moments from downtown Winnetka, Lake Michigan beaches, Metra, boutique shopping, acclaimed restaurants and beautiful parks. Residents of Winnetka Mews enjoy an outdoor pool, fitness center, on-site management and a dedicated building engineer. Sophisticated, spacious and beautifully appointed, this exceptional residence offers an effortless lifestyle in one of Winnetka's most desirable locations.

640 Winnetka Mews Unit #403, Winnetka

$2,695,000

4 Beds ⋅ 5 Baths ⋅ 12715045 MLS ⋅ ACTIVE Status

A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins. Two bedrooms were combined into a spacious home office (larger than the primary) with hardwood floors, updated lighting, custom closet built-ins, and upgraded networking. The first-floor office was reimagined as a dramatic library, with custom maple built-ins, matching ceiling moldings, a window seat, and high-gloss lacquered finishes. The home is wired throughout for CAT6 and wifi, with home theater wiring, an upgraded security system, energy-efficient attic insulation, and improved HVAC routing - smart, efficient, and move-in ready. Owner is a Licensed Real Estate Broker.

1140 Oakley Avenue, Winnetka

$2,595,000

12213495 MLS ⋅ ACTIVE Status

Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own architect and builder, or take advantage of thoughtfully designed plans already in the final stages of the permitting process. With multiple PINs and over 63,000 square feet of land, the possibilities are endless. This property presents the rare opportunity to create a private estate with unparalleled scale, luxury, and privacy. Nestled among some of the North Shore's finest homes, the setting perfectly balances serene seclusion with everyday convenience. Located within the nationally acclaimed New Trier High School District, the property is just minutes from the boutiques, restaurants, and amenities of both Winnetka and Wilmette. Bring your vision and your grandest ideas to this remarkable offering.

61 Woodley Road, Winnetka

$4,200,000

5 Beds ⋅ 9 Baths ⋅ 12701871 MLS ⋅ ACTIVE Status

Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after location. Masterful custom cabinetry fills the bright, well equipped kitchen begging to be used for entertaining or casual family gathering. The primary suite boasts a view of the treetops and almost welcomes you out to the balcony which adjoins. The spa inspired primary bath has all the ammenities. When the weather starts getting nice the backyard patio extends the home to the outdoors and beautifully compliments the aesthetic. You really must see this home to appreciate how the approximately 6950 sq/ft on first and second floors and 2800 sq/ft of beautifully finished lower level can become the home of your dreams!

1128 Mt. Pleasant Road, Winnetka

$2,795,000

5 Beds ⋅ 6 Baths ⋅ 12688601 MLS ⋅ ACTIVE Status

Basement renovation just done to add 6th bedroom that adjoins full bath! So much light enters basement through windows! A rare opportunity to own a home on one of the most sought after, serene country-like settings on the North Shore. The house is just steps from the Indian Hill Golf Club and part of the coveted Indian Hill neighborhood. Be close to other magnificent homes and wooded and mature landscaping. Only one owner since home was completed on this property in 2012. Stately and traditional two story brick home with 5 bedrooms and 5.1 baths. The large finished basement with overly generous storage allows for a 6th bedroom. The basement has a full bathroom and space that is plumbed and ready for installation of a kitchen. Your eyes are drawn to the gracious two story foyer finished in marble. The rest of the first floor is finished in hardwood oak and cherry except for the family room that has plank flooring. The wel designed first floor has spacious living room, dining room, family room, eat-in kitchen, den and mudroom. The enormous primary bedroom is a tranquil retreat with spa like bath with jacuzzi and walk-in shower finished in travertine tile. The new owner will greatly appreciate the two walk-in closets located in this escape space. There are four other bedrooms on the second floor. Mature landscaping and brick pavers offer welcoming outdoor space. The driveway also boasts of brick pavers. Approximately 4319 square feet of above ground living space and 2066 below in basement for a total of 6385 square feet of enjoyable space. So close to schools, shopping, and even the beach. Enjoy the incomparable Winnetka lifestyle. Hurry, because this house, designed for everyday living and gracious entertaining, will not last long!

73 Locust Road, Winnetka

$4,949,000

5 Beds ⋅ 7 Baths ⋅ 12698685 MLS ⋅ ACTIVE Status

Perfectly nestled on one of Winnetka's finest enclaves, this stately 6-bedroom, 5.2-bath Georgian estate offers a rare fusion of architectural elegance, exceptional craftsmanship, and resort-style amenities. Set on nearly an acre of meticulously manicured grounds, the estate is introduced by a sweeping circular drive that highlights the home's classic brick facade, brand-new DaVinci slate roof, columned portico, and timeless symmetry. Together, these elements create a striking first impression and set the stage for interiors that exude sophistication at every turn. Step inside the grand "bookmatched" marble-floored foyer, where a dramatic staircase sets a refined tone for the home. To one side, the formal living room offers an inviting gathering space anchored by a marble fireplace, while the formal dining room is perfectly scaled for both intimate dinners and large-scale entertaining. A massive, richly paneled home office with dramatic coffered ceilings offers an impressive and inspiring workspace. At the heart of the home, the gourmet kitchen boasts professional-grade appliances, an oversized island, full wall of pantry storage, and a sunlit breakfast area all overlooking the magnificent pool and grounds. A butler's pantry ideally placed between the kitchen and dining room provides effortless entertaining. Just beyond, the kitchen opens to a cozy family room with a fireplace and wet bar, while French doors lead to an expansive covered terrace framed by graceful curved archways and cooled by ceiling fans. This spectacular outdoor living space features a brand-new outdoor kitchen fully equipped for grilling and al fresco dining, leading to the sparkling pool, surrounding patio and yard, creating a seamless setting for summer entertaining and secluded relaxation. A convenient first-floor laundry/mud room right off the 3-car heated garage with epoxy flooring and 2 powder rooms adds everyday ease. Upstairs, the elegantly appointed primary suite offers dual walk-in closets, a dedicated vanity area, and a spa-inspired bath with separate vanities and radiant heated floors. Four well-proportioned additional bedrooms, each with generous closets and either en-suite or adjoining baths, provide comfortable accommodations for family and guests. This level is further enhanced by expansive linen closets, abundant storage, and a dedicated luggage room. The impeccably finished lower-level rivals any private club, featuring a state-of-the-art home theatre, richly paneled billiards and game room, fully outfitted bar, expansive fitness studio, wine cellar, guest suite, and a dedicated woodshop for refined hobbyists or craftsmen. Located in one of Winnetka's most prestigious locations and served by its award-winning schools, this remarkable estate perfectly balances classic sophistication with modern luxury. Combining architectural pedigree, unparalleled amenities, and impeccably landscaped grounds, this is a home to be cherished for generations. Furniture available for sale.

320 Woodley Road, Winnetka

$2,785,000

6 Beds ⋅ 6 Baths ⋅ 12680099 MLS ⋅ ACTIVE Status

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.

82 Woodley Road, Winnetka

$29,900,000

7 Beds ⋅ 13 Baths ⋅ 12680920 MLS ⋅ ACTIVE Status

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!

319 Sheridan Road, Winnetka

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 12673083 MLS ⋅ ACTIVE Status

Rarely available first floor primary! 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. Owner extremely motivated!!!

42 Woodley Road, Winnetka

$2,569,900

6 Beds ⋅ 6 Baths ⋅ 12637769 MLS ⋅ ACTIVE Status

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.

62 Woodley Road, Winnetka

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