Browse All Winnetka IL Properties for Sale

4 Beds ⋅ 6 Baths ⋅ 12798477 MLS ⋅ NEW Status

Welcome to this exquisite, sun-drenched 4+1 bed, 5.1 bath luxury home on an oversized lot (50x232) at the Winnetka/Glencoe border. Located on a beautiful tree lined cul-de-sac and adjacent to the Green Bay trail, this home sits across the street from Glencoe Park. The moment you walk in, you are greeted by a bright formal living room featuring one of the home's four fireplaces, flanked by an adjacent office adorned with beautiful, oversized bay windows. Designed for seamless modern living, the main level flows into a sophisticated formal dining room, an open-concept kitchen, breakfast room and family room overlooking expansive backyard. The main level features a light, neutral palette and newer light fixtures throughout. The second floor is a private retreat where all four bedrooms feature dedicated en suite baths, and two enjoy the luxury of private decks. All new hardwood flooring throughout this level along with a fresh paint. Spacious primary bedroom features large walk in closet and elegantly renovated bathroom with double vanity and a breathtaking walk in shower. A dedicated second-floor laundry room includes a newer washer/dryer. Fully finished basement adds incredible value with a huge recreation room, a full bath, bar and a flexible 5th bedroom/home gym. Enjoy cozy evenings anchored by the home's 4 distinct fireplaces. The outdoor oasis features an oversized paver patio, massive yard, and an oversized 2-car garage. Impeccably maintained with newer appliances, wine cooler, updated mechanicals, and a central vac system, this home offers total peace of mind. Unbeatable location just minutes from Hubbard Woods shopping, dining, and the Metra train.

285 Woodlawn Avenue, Winnetka

$3,499,000

6 Beds ⋅ 7 Baths ⋅ 12797319 MLS ⋅ NEW Status

Extraordinary luxury new construction in a prime Winnetka location, with anticipated completion Summer 2027. Set on over a quarter acre, this exceptional residence will offer approximately 5,500 square feet with 8 bedrooms, each offering en-suite bath access, and 7 baths, blending elevated craftsmanship, timeless finishes, and thoughtful design for sophisticated yet comfortable living. Soaring 9'6" ceilings, engineered hardwood flooring, and designer ceiling details create an impressive backdrop for beautifully appointed interiors. The chef's kitchen will feature Sub-Zero and Wolf appliances, custom cabinetry, quartz countertops, a 10-foot island with seating, and a fully equipped butler's pantry with wine refrigeration. Opening seamlessly to the family room with a custom fireplace and built-ins, this inviting gathering space is designed for effortless everyday living and entertaining. A dramatic 12-foot folding door system connects the interior to the backyard, creating an exceptional indoor-outdoor living experience. An attached two-car garage with an EV charger adds modern convenience. Ideally located moments from downtown Winnetka, the train, parks, schools, and Lake Michigan. A rare opportunity to personalize finishes and create your dream home in an outstanding North Shore setting. Please note: Interior photos showcase the builder's previous project.

795 Pine Street, Winnetka

$1,385,000

4 Beds ⋅ 3 Baths ⋅ 12791044 MLS ⋅ NEW Status

Nestled on one of Winnetka's most desirable streets in Hubbard Woods, this beautifully maintained brick residence offers a timeless blend of classic charm, thoughtful design, and exceptional outdoor living in the heart of Winnetka. Designed for both everyday comfort and effortless entertaining, the home features a welcoming, connected floor plan with a gracious flow between the living and dining rooms. Hardwood floors, plantation shutters, and refined details add warmth and character, while a wood-burning fireplace framed by built-in cabinetry creates an inviting focal point in the living room. The adjoining dining room connects seamlessly to the updated chef's kitchen, featuring premium appliances and abundant workspace. Just beyond, the sun-filled family room is surrounded by walls of windows and glass doors that bring the outdoors in and open to a beautifully landscaped backyard retreat. A versatile first-floor bedroom and full bath offer exceptional flexibility for guests, extended family, a private home office, or au pair accommodations. Upstairs, the primary suite features a newer private en-suite bath, while two additional well-proportioned bedrooms share a fresh, full hall bath. The private outdoor oasis is a true highlight, featuring an expansive newer deck with built-in seating, a charming pergola, and a patio perfect for al fresco dining, summer gatherings, or quiet moments surrounded by nature. The finished lower level provides valuable additional living space, ideal for recreation, fitness, play, and abundant storage. A detached two-car garage adds everyday convenience, while the home's surprisingly spacious layout offers more room than meets the eye. Ideally situated within walking distance of Hubbard Woods School, the train, parks, boutique shopping, dining, and the lakefront, this special property pairs an exceptional neighborhood setting with inviting indoor-outdoor living. A wonderful opportunity to enjoy the charm, convenience, and lifestyle that make Winnetka and the North Shore so desirable.

1450 Asbury Avenue, Winnetka

$1,475,000

4 Beds ⋅ 4 Baths ⋅ 12793638 MLS ⋅ CONTINGENT Status

RARE FIND - EXCEPTIONAL STONE & BRICK RANCH ON A PRIVATE HALF-ACRE! This home presents 3 unique opportunities as an ideal canvas: Add your own cosmetic updates over time | Reimage the existing residence through a comprehensive renovation or | Create a spectacular custom dream home! Set on a beautiful, HALF- ACRE, the property offers the perfect canvas for reimagining a home in an extraordinary setting. With no comparable lots currently available and neighboring luxury properties, the possibilities are truly exceptional. The existing home features a desirable floor plan with 4 bedrooms, 3.5 baths, and generously proportioned living spaces, including a living room, family room, dining room, and sunroom. The spacious kitchen features a premium Sub-Zero refrigerator, center island, separate breakfast room, and dedicated butler's pantry. A practical mudroom includes a convenient walk-in pantry, along with a newer washer and dryer. Additional highlights include 2 wood-burning fireplaces, newer mechanicals, solar panel integration, underground lawn sprinkler system, 2 car attached garage, and 2 separate paver-stone patios overlooking expansive backyard. The partial basement provides additional living space and exciting potential for future customization. Ready for its next chapter, this is a rare chance to create something truly special in an unmatched location - whether enhancing the existing character, undertaking a transformative renovation, or exploring a custom new residence. Home being sold AS-IS.

1230 Lindenwood Drive, Winnetka

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 12789167 MLS ⋅ ACTIVE Status

381 Linden Street, Winnetka

$285,000

2 Beds ⋅ 1 Baths ⋅ 12784655 MLS ⋅ ACTIVE Status

Rarely available and ideally located in the heart of Hubbard Woods, this charming 2-bedroom, 1-bath condo is the largest unit in Winnetka Manor. Just steps from the Metra, shops, restaurants, parks, Lake Michigan, and the bike path, this home offers an exceptional blend of character, comfort, and convenience. The inviting layout featuring a spacious living room, separate dining room, and two generous bedrooms. Hardwood floors, fresh neutral paint, and abundant natural light enhance the timeless appeal. The updated kitchen features granite countertops and stainless-steel appliances, while the refreshed bath, decorative fireplace mantel, California Closets throughout, and a walk-in primary closet add thoughtful touches. Winnetka Manor is a well-maintained community. Terrific move-in-ready home!

1097 Merrill Street Unit #G2, Winnetka

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 12787597 MLS ⋅ CONTINGENT 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

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 12779584 MLS ⋅ ACTIVE Status

Winnetka

$1,995,000

5 Beds ⋅ 5 Baths ⋅ 12786632 MLS ⋅ ACTIVE Status

Completely reimagined and thoughtfully designed, 1288 Sunview is an exceptional Winnetka home set on a picturesque half-acre lot. The property has been redeveloped from top to bottom with a focus on design, functionality and quality, creating a home that feels entirely new while maintaining the character and setting of the original property. The spacious floor plan offers 5 bedrooms, 3 full bathrooms and 2 half bathrooms, including four bedrooms upstairs and a fifth bedroom with ensuite bath on the main level that can function as a second primary suite. Two beautiful masonry fireplaces serve as focal points within the home, adding warmth, character and a timeless architectural element to the thoughtfully designed spaces. Multiple living spaces include two family rooms, a dedicated office and a fully finished basement, providing exceptional flexibility for today's lifestyle. The home's design creates an easy flow between the living, dining, kitchen and family spaces, while the main-level bedroom offers versatility as a guest suite, bedroom or second primary. The upper level features a spacious primary suite along with three additional bedrooms and a full hall bathroom. A convenient second laundry area is located on the bedroom level, while the fully finished basement provides additional recreation and living space, along with laundry, storage and mechanical areas. Outdoor living is a major highlight, with an expansive back patio, generous backyard and rooftop deck overlooking the property. The huge half-acre lot provides an uncommon amount of outdoor space in this Winnetka setting and is ideal for entertaining, relaxing or enjoying time with family and friends. Additional features include a two-car attached garage with EV charging hookup, beautiful hardwood flooring and thoughtfully designed spaces throughout. Set in an exceptional Winnetka location, 1288 Sunview is just minutes from New Trier schools, Skokie Playfields, parks, downtown shopping and dining, Metra and the lakefront. A rare combination of thoughtful design, substantial living space, architectural character and an exceptional half-acre setting, 1288 Sunview has been completely reimagined for modern living and is truly move-in ready.

1288 Sunview Lane, Winnetka

$1,995,000

12780362 MLS ⋅ ACTIVE Status

A rare offering on one of East Winnetka's most desirable streets, just two blocks from Lake Michigan. This exceptional property presents a unique opportunity to either thoughtfully renovate an existing home or create a custom residence with the potential for approximately 8,400 square feet of finished living space. Set on a beautiful, private lot surrounded by lush greenery, the property offers the perfect canvas for reimagining a home in an extraordinary setting. With no comparable lots currently available, and neighboring properties valued at over $5 million, the possibilities are truly exceptional. Enjoy an easy walk to downtown Winnetka, Greeley School, New Trier High School, the Metra train, Lake Michigan, parks and more. A rare opportunity to bring your vision to life in an unmatched location, whether through a beautiful renovation or a custom new build. Existing home is sold as-is, with no inspections.

510 Ash Street, Winnetka

$1,995,000

5 Beds ⋅ 3 Baths ⋅ 12775682 MLS ⋅ ACTIVE Status

510 Ash Street, Winnetka

$2,750,000

5 Beds ⋅ 6 Baths ⋅ 12783379 MLS ⋅ CONTINGENT Status

Situated on over half an acre on picturesque private Fisher Lane in the heart of Hubbard Woods, this gracious, grand yet warm 5 bedroom home is flooded with natural light and pairs impressive scale with timeless architecture and beautifully connected living spaces. Walls of windows frame lush green views of the ravine throughout, while soaring ceilings, hardwood floors and elegant millwork give the home a sense of presence from the moment you enter. The expansive 2 year old kitchen is the heart of the home, anchored by a spectacular oversized 11 foot island and opening to a sun-drenched breakfast room with fireplace and French doors to the outdoors. Generous formal and casual living spaces offer incredible flexibility for both everyday life and entertaining including a formal living room w/ fireplace, formal dining room, distinguished office/library, large family room w/ custom built-ins flanking the fireplace & attached 3-car garage. The dramatic second-floor gallery, vaulted ceilings and magnificent arched window add an unexpected architectural moment on the second floor where you'll find 5 generously sized bedrooms, 4 full bathrooms, a laundry room & abundant storage/closets. The massive primary suite is outfitted with a steam shower, soaking tub, dual vanities & dual walk-in closets. The finished lower level offers even more living space with a rec room, gym, wine storage & massive storage room. This is a truly special home that feels substantial yet inviting, classic yet fresh, and designed to be lived in beautifully.

936 Fisher Lane, Winnetka

$1,049,000

2 Beds ⋅ 2 Baths ⋅ 12779783 MLS ⋅ PENDING Status

WELCOME TO A RARELY AVAILABLE FIRST FLOOR END UNIT IN POPULAR HEDGE ROW. A CHARMING INTERIOR ATMOSPHERE IS PROVIDED BY SOUTH AND WEST EXPOSURE. CROSS LIGHT IS THE BEST! THE OPEN FLOOR PLAN DESIGN IS VERY APPEALING. IT INCLUDES A GROUPING BY THE FIREPLACE, A TRADITIONAL DINING SPACE AND A VERY SPACIOUS KITCHEN WHICH OVERLOOKS THE MAIN AREA AND OPENS TO A FAMILY ROOM. A TRUE DELIGHTFUL FEATURE IS A SEPARATE OFFICE WHICH HAS WOODSY CROSS VIEWS AND OPENS TO A CHARMING PATIO AND GARDEN. THE VIEWS, IN GENERAL, ARE SIMILAR TO A SINGLE FAMILY HOME! THE GENEROUS MASTER SUITE HAS THREE CLOSETS (1 WALK-IN) AND A PRIVATE BATH WITH TWO SINKS AND SEPARATE TUB & SHOWER. THE SECOND BEDROOM HAS ITS OWN BATH AS WELL. THE UNIT INCLUDES A WASHER AND DRYER. TWO PARKING SPACES AND A STORAGE AREA ARE IN THE INDOOR GARAGE. PETS ARE ALLOWED. THERE IS EASY ACCESS TO THE EVER-GROWING DELIGHTS OF DOWNTOWN WINNETKA!

360 Green Bay Road Unit #1D, Winnetka

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 12783024 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

$525,000

2 Beds ⋅ 2 Baths ⋅ 12774391 MLS ⋅ PENDING Status

602 Lincoln Avenue, Winnetka

$2,195,000

4 Beds ⋅ 4 Baths ⋅ 12777637 MLS ⋅ CONTINGENT Status

HOME EXCLUDED FROM FLOOD ZONE/INSURANCE - DOCUMENTATION PROVIDED. Exclusive quality builder-designed home with fabulous curb appeal! This exceptional residence features an open-concept floor plan, 4 fireplaces, 2 additional parking spaces and dual laundry areas. The kitchen offers Sub Zero/Thermador stainless steel appliances and a custom designed island. Coiffured ceilings in the dining room and den add an elegant touch. The expansive finished lower level offers a versatile sleeping area and additional living space. Beautiful hardwood flooring extends throughout the main and upper levels. 9 foot ceilings throughout really expand the space! 2 additional bedrooms upstairs have ensuite bathrooms. The garage is equipped with EV charging, while a new fence enhances the privacy and curb appeal. Step outside to your own private backyard retreat, surrounded by lush, thoughtfully designed landscaping with an in ground sprinkler system - perfect for relaxing or entertaining. Built-in vegetable garden area next to garage! Close proximity to schools and downtown makes it convenient for walking.

1036 Ash Street, Winnetka

$3,999,000

5 Beds ⋅ 9 Baths ⋅ 12774096 MLS ⋅ ACTIVE Status

1128 Mt. Pleasant Road, Winnetka

$975,000

4 Beds ⋅ 3 Baths ⋅ 12767043 MLS ⋅ CONTINGENT Status

Welcome to 1163 Asbury Avenue, a classic 4-bedroom home on a picture-perfect street in the heart of Hubbard Woods. Just blocks from town, the train, schools, parks, and neighborhood amenities, this is a wonderful opportunity for a buyer ready to bring their creativity and vision to a home in an exceptional Winnetka location. The main level offers generous living and dining rooms, a bright eat-in kitchen, and an expansive family room overlooking the deck and large private backyard. The floor plan offers plenty of space to work with, whether updating the existing layout or reimagining it to suit your needs. An attached one-car garage adds everyday convenience. Upstairs are four well-sized bedrooms and two full baths, while the lower level includes a recreation room and additional bonus space with flexibility for a home office, exercise room, playroom, or storage. Additional highlights include Hardie board siding, replacement windows, and updated mechanicals. The combination of space, location, and opportunity makes this home especially compelling. Bring your ideas and create something special in this incredible setting. The property is being sold as-is.

1163 Asbury Avenue, Winnetka

$2,699,900

4 Beds ⋅ 6 Baths ⋅ 12767250 MLS ⋅ PENDING Status

A picture-perfect classic North Shore custom home filled with elegance & coastal New England charm by notable architect Paul Konstant. Graceful arched windows and a welcoming columned entrance create a storybook exterior reminiscent of a Nantucket retreat. Step inside to the blue stone accented foyer where soaring ceiling, crisp tailored millwork and double-hung Marvin windows set the tone for beautifully scaled, light-filled interiors. The sun-drenched living room is anchored by a double-sided stone fireplace with a classic honed black granite surround, seamlessly connecting to the formal dining room. Picturesque views of the front gardens are just beyond the double set french door stepping out bluestone patio with pergola. Continue through the butler's pantry, which doubles as the perfect coffee/smoothie station and command center before entering the quintessential New England-inspired white Chef's kitchen. A huge island with seating, expansive honed soapstone countertops, original Shaw farm sink, Visual Comfort bronzed brass pendants, Wolf and Sub-Zero appliances a walk-in pantry deliver the perfect balance of beauty with function. A cozy built-in breakfast booth overlooks the gardens while the adjoining family room, complete with its own stone fireplace, offers a warm and inviting retreat-just steps from the heart of the home. A second powder room off the mudroom has side door access to the bluestone patio and lush gardens, all beautifully tucked inside by classic white lattice fencing. Ascend to the second floor, where the sitting room welcomes you with beautifully detailed architectural doors and custom casings carry the home's craftsmanship throughout. Private positioned, the luxurious primary suite offers a serene escape with a marble bath featuring dual walnut vanities, a soaking tub, and two separate walk in closets. A second bedroom enjoys its own en-suite bath, while bedrooms three and four share a timeless bath appointed with classic white subway tile and marble flooring & c-tops. Convenient second-floor laundry, with an additional hookup in the lower level, completes this thoughtfully designed floor. The expansive lower level is fab: soaring ceilings & abundant natural light from generous window wells. An oversized entertainment room with custom bookshelves/built-in television center sets the stage for movie nights, while a separate fitness room adds everyday convenience. A fifth bedroom with an adjoining full stone bath creates ideal guest quarters, and an additional storage room provides exceptional functionality. Framed by manicured boxwoods, lush gardens, and accented by lattice fencing, this custom coastal residence captures the magic of New England living in the heart of East Winnetka. Walk to Greeley, New Trier, lake and train... as this east location is an A+. Seller is installing a new DaVinci composite cedar shake roof Oct. 6th making it even have a more picture perfect ending!

252 Myrtle Street, Winnetka

$1,400,000

5 Beds ⋅ 5 Baths ⋅ 12736036 MLS ⋅ PENDING Status

Set on approximately half an acre in sought-after Hubbard Woods, this five-bedroom + office, 4.1-bath home offers exceptional space, a versatile floor plan, and an outstanding North Shore location. The thoughtfully designed main level features a private office or living room, formal dining room, updated eat-in kitchen, and spacious family room overlooking the backyard, in-ground pool, oversized deck, and patio, perfect for gatherings with friends and family. A convenient mudroom provides direct access to the attached two-car garage. Upstairs are five bedrooms, an office and a dedicated laundry room, while the walk-up attic offers abundant storage and exciting potential for additional finished living space. Ready for its next chapter, the home presents a wonderful opportunity to update and personalize while enjoying a Hubbard Woods address rarely available at this price point-all within walking distance of the train, shops, and Winnetka schools.

874 Boal Parkway, Winnetka

$1,100,000

4 Beds ⋅ 2 Baths ⋅ 12746221 MLS ⋅ CONTINGENT Status

Charming House in Winnetka with Timeless Appeal Welcome to this charming four-bedroom, 1 1/2 bath Winnetka home that beautifully blends classic character with comfortable, inviting living spaces. Warm and welcoming from the moment you walk past the stately over four-hundred-year-old Burr Oak in the front yard, this home offers a wonderful combination of livability and an in-town location. Thoughtfully maintained and filled with old-world craftsmanship, the entire home has a comfortable flow for everyday living with custom details throughout with features such as wood moldings, built-in bookshelves, and hardwood floors. The first floor includes spacious living and dining rooms and a lovely sunroom/den with windows on three sides. The second floor features a generous sitting room/office with beautiful 180-degree views of the property. The peaceful, private rear yard has a gracious stone patio. A commercial Life Safety System protects the entire home and alerts local authorities in case of fire, smoke, or carbon monoxide danger. The current owner has lived there for fifty-one years and has never had water in the basement. The location of this home is unique, situated in a desirable Winnetka neighborhood within easy walking distance of schools and parks, and three blocks to the train, shopping, dining -and all this wonderful community has to offer. This is a truly lovely home that offers a special opportunity to enjoy the charm and convenience of Winnetka in a setting that is easy to love.

592 Provident 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

$2,699,000

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

$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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