Winnetka IL Real Estate & Homes for Sale

Winnetka "tree streets" gem! This fully updated home blends classic exterior charm with a modern, open layout! Featuring three bedrooms, two and a half baths, a gorgeous kitchen and a beautiful backyard. Huge living room anchored by pretty fireplace flows seamlessly into open newer white kitchen and dining area. Family room - located just off the kitchen - opens to a fully fenced backyard with nice paver patio - and separate patio for grilling. Thoughtful mudroom area, powder room, and entry round out the first floor. The second floor features a large primary suite with two closets and a renovated primary bath. Two more family bedrooms share updated hall bath. Full basement with finished recreation room, laundry room, and huge storage room. Pull down stair attic has tons of additional storage or potential for future expansion. Deep, fully fenced yard with patio provides the perfect retreat. Detached two car garage with built in shelves. Unbeatable location: walk to top-rated schools, the Winnetka train, and all downtown Winnetka has to offer!

This 4-Bedrm and 2-Bath Cottage style home sits on a 5,267 Sq Ft lot in coveted Winnetka Hubbard Woods. This property located in top -rated schools (Hubbard Elementary) presents potential to renovate, expand or reimagine in a premier North Shore setting. The main floor plan unveils an open concept with a sprawling Family room filled with natural light next to separate sitting room with a gorgeous brick fireplace and hinged French doors to a formal Dining Room. A generous size kitchen finished with 36" cabinetry with glass facade accents, stainless steel appliances. Two good size bedrooms with a shared full bathroom between and a room as a separate office. Hardwood floors throughout. The second floor has 2 bedrooms and a loft. Full unfinished lower level with a half bathroom. Private fenced in yard and plenty of parking. Close to Metra, downtown Winnetka, Lake Michigan, parks, trails, shopping and MORE *** Sellers motivated.

Incredible opportunity to develop, customize, or thoughtfully renovate this traditional four-bedroom home situated on a picturesque half-acre lot backing directly to the Winnetka Golf Club on a quiet, tree-lined street. Whether you're envisioning a stunning custom new construction or transforming the existing residence into your dream home, this exceptional property offers endless possibilities in one of Winnetka's most desirable locations. The existing home features nearly 2,900 square feet of living space, an attached two-car garage, two main-level bedrooms, generous living and entertaining areas, and a partially finished basement with high ceilings that provides excellent expansion potential. Large windows throughout the home frame beautiful views of the golf course and fill the interior with natural light. The expansive backyard offers a rare combination of privacy, open green space, and breathtaking golf course settings, creating an ideal setting for outdoor entertaining or a future custom residence. All of this is just moments from award-winning schools, parks, downtown Winnetka, Metra, shopping, dining, and the lakefront. A truly rare opportunity to secure a premier half-acre homesite and bring your vision to life.

Stunning million dollar+ renovation of a picture perfect brick center-entry Georgian colonial ideally positioned on one of Winnetka's most coveted streets with breathtaking views. Thoughtfully reimagined and meticulously renovated from top to bottom in 2022, this exceptional residence blending timeless architecture with beautifully curated finishes, impeccable craftsmanship, and modern luxury throughout. Featuring a fabulous floor plan with gracious, light-filled living spaces, an iconic home designed for both entertaining with ease and everyday living. The welcoming foyer opens to a sophisticated living room that flows seamlessly into a private office with walls of windows overlooking the spectacular professionally landscaped grounds by Red Spade in the last 2 years. An elegant dining room with oversized windows streaming with natural light provides the perfect setting for any size gathering. At the heart of the home is an incredible chef's kitchen appointed with top-of-the-line appliances, custom cabinetry, and a generous island with seating, opening effortlessly to the sun-filled family room with panoramic vistas. A beautifully designed mudroom adds everyday convenience. The serene primary suite features a spa-inspired bath, and a large, exceptional custom walk-in closet with laundry. Two additional bedrooms are connected by an inviting, sun-filled playroom or lounge, creating the perfect family retreat. The ultra-cool third floor suite with an additional full guest suite with bedroom, lovely bath, and laundry, provides ideal accommodations for guests, teens, or an au pair. The finished lower level offers a spacious recreation room filled with natural light along with abundant storage. Outdoors, an expansive bluestone patio overlooks beautifully curated gardens and grounds, creating a private setting for entertaining and relaxation. A two-car garage completes the property. Located in one of Winnetka's most sought-after neighborhoods, this truly turnkey home offers an unmatched lifestyle just steps from town, the train, schools, parks, shops, and the Community House.

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!

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!

BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale and warmth. Hardwood floors and a flowing layout provide comfortable everyday living along with excellent entertaining space throughout. A heated and air-conditioned bonus room off the garage adds exceptional versatility, ideal for a home office, gym, playroom, studio, or additional lounge space. Situated on a generous corner lot with expansive outdoor space, the property offers endless potential to enjoy as-is or further personalize over time. Conveniently located near top-rated schools, parks, downtown Winnetka, and Metra access, this is a rare opportunity to own a home with outstanding space, character, and flexibility in an exceptional North Shore location.

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.

Incredible architecturally divine jewel box nestled on one of Hubbard Woods' most coveted cul-de-sac streets. Extraordinary vintage details in this distinctive and beautifully scaled Georgian home, where timeless elegance has been thoughtfully enhanced with over $1.2 million in renovations & infrastructure improvements. Step inside and right away feel the elegant original details with original black & white marble floors, leaded glass windows and doors, gorgeous plaster dining room ceiling, interior arched doors, and rich architectural beams. The gracious first floor offers seamless circular flow, featuring a stately step-down living room/great room with a French mantel fireplace and curved leaded bay windows overlooking the professionally landscaped front yard. Oversized dining room, ideal for entertaining, showcases arched French doors and a Benjamin Marshall-inspired cove-molded ceiling and Philip Jefferies wallpaper. Just completed, a beautifully subtle off-white Chef's kitchen highlighted by creamy-hued Ann Sacks glazed subway tile, Wolf stove accented by Ikat inlay marble backsplash & 2 sinks. Brand new breakfast room space with custom glass built-ins leads to new oversized mudroom with artistic tiled flooring striking the perfect balance of fun. Office with FP & original mosaic tile restores character. Stoic staircase with original wrought iron handrails leads to 3 spacious bedrooms centered around a gracious reception hallway with a continued staircase to the 3rd floor. Tailored primary suite with custom window treatments in Kravet fabric ties into the renovated classic marble spa bath. Two new en-suite baths for both of the other beds and an attic space plumbed and ready for another bed/playroom. Just completed in June 2026, a dug-out lower-level rec space with exceptional ceiling height and 4th bedroom and marble bath. Beyond the beautiful finishes, this home has been comprehensively upgraded with a new architectural shingle roof, all-new copper gutters and downspouts, a fully underpinned foundation with deep-dig basement, new Marvin oversized basement windows, new sewer line, upgraded electrical service with underground power, new water service, new boiler, EV charger, and extensive renovations throughout both the first and second floors. If new construction is not your thing...then get ready to be taken back to the beautiful world of character & charm with all the new must-have upgrades of today's living. This was a labor of love rehab that got short due to a relo situation, so stomp on this one to be the first owner to enjoy the completed regal renovation. Steps to Hubbard Woods Elementary, 8 min walk to train and all the boutique stores & restaurants in Hubbard Woods...so convenient & divine living!

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 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.

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.

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!

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).

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.

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.

It is exceptionally rare to find a privately set masterpiece with sweeping views of the Winnetka Golf Course that also offers the opportunity to step directly into a freshly completed 2025/2026 designer showcase renovation. Nestled on a beautifully landscaped half-acre site overlooking the golf course, this extraordinary stone residence has been impeccably transformed through a comprehensive renovation marrying timeless architecture with sophisticated design. With coveted western exposure and surrounding lush grounds, the home captures spectacular sunset skies across the golf course from most rooms in the home. Thoughtfully curated throughout, the 6 bed, 9 bath home showcases exceptional craftsmanship with a diamond leaded glass front door, custom millwork, designer lighting, 5 fireplaces, and a refined mix of marble, porcelain, and rich wood flooring. Smart home enhancements include Lutron lighting and integrated Sonos access points throughout much of the home. Ring security and exterior cameras have been integrated to provide both convenience and peace of mind. The stunning chef's kitchen was designed with both beauty and functionality in mind, featuring Taj Mahal honed quartzite countertops with elegant ogee edging, custom cabinetry, Perrin & Rowe fixtures, Franke sink, Sub-Zero refrigeration, Thermador appliances including a 6-burner range with grill, both Bosch and Fisher & Paykel dishwashers, warming drawer, walk-in pantry, and dual butler's pantries. The adjacent breakfast area opens beautifully to the outdoor entertaining spaces and picturesque golf course setting beyond. The primary suite, with a spacious private terrace overlooking the golf course, was designed with a quiet, hotel-inspired feel, featuring Calcutta Gold marble heated floors and shower, Victoria + Albert freestanding soaking tub, custom built-ins, iceberg polished quartzite surfaces, and elevated designer finishes throughout. All guest suites are en-suite with ample custom closets and continue the home's sophisticated aesthetic with premium quartzite countertops and Perrin & Rowe or Rohl Lombardia fixtures in the bathrooms. Designed for exceptional entertaining and lifestyle living, the expansive lower level includes a theater room, recreation space, workout/wellness room, sauna, wet bar, expansive wine cellar, guest suite, secondary kitchen, and extensive storage. Outdoors, professionally designed gardens provide exceptional entertaining areas including gas grill area with fire pit. The fully fenced and sprinklered yard creates a remarkably private setting with sweeping golf course views. Additional highlights include a slate roof, newer mechanical systems, dual sump pumps with triple redundancy, whole-house water filtration, generator backup, 3-car attached heated garage with additional overflow parking, and an advanced security system. Conveniently located near schools, AC Nielsen Tennis Center, Skokie Playfields and the Winnetka Ice Arena while positioned along one of the North Shore's sought-after golf locations.

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.

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.

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

Better than NEW! Impeccably renovated 6BR/5.2BA center-entry colonial set on an oversized (66 x 159) professionally landscaped lot. This four-level home features abundant natural light, oversized windows, wide room openings, custom millwork and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end finishes and thoughtful design exist at every turn. First floor includes a gourmet kitchen, butler's pantry, formal dining room, sun-drenched living & family spaces, a private home office, and handsome mudroom & full 1st fl laundry room. Upstairs, the luxurious primary suite offers a spa-like shower, double vanity and walk-in his and hers closets. Additional bedrooms are generously sized, one bedroom is en-suite and the 3rd & 4th bedrooms share a large hall bath. There is additional 2nd floor laundry for ultimate convenience. Fully finished lower level and 3rd fl provide flexible living space for extra BR's, recreation, guests, or work-from-home needs. Both floors have gorgeous full bathrooms. Exceptional outdoor living space includes brick patio, lush landscaping and private, fenced yard. A rare blend of classic charm and modern luxury in a prime location, just blocks to Hubbard Woods town, train, shops, restaurants, school, parks, the forest preserve bike and running trails. Easy access to downtown Chicago.

Nestled down a winding, private road on 1.9 meticulous park-like acres, this grand, almost 10,000 square foot residence exudes luxury and timeless elegance. The front entrance is set apart from the road by a sweeping circular drive bordered by private hedges and mature trees. Upon entering the stately, two-story foyer with a 25' ceiling, bridal staircase, black and white marble floor, formal powder room and two coat closets, you are greeted by the sophistication that defines this home. The main level features a spacious, step down living room with inlaid floors, a marble, gas and wood fireplace, and two picture windows that fill the room with natural light. Pass through the living room to an adjoining, architecturally beautiful solarium with a slate floor, that offers panoramic views of the lush grounds surrounding the residence. The formal dining room also features inlaid floors, and picture window. The handsome family room with custom cabinetry, lighting, millwork, and a marble, gas and wood fireplace, provides the perfect space for entertaining and relaxation while overlooking a yard large enough for a pool. The family room seamlessly flows into a large kitchen area that includes not only a custom kitchen but also a breakfast room, butler's pantry, back staircase, and mud room. The butler's pantry has an ice maker, second dishwasher, and beverage refrigerator. Upstairs the luxurious primary bedroom suite boasts a marble, gas and wood fireplace, walk-in closet, and an adjoining sun room with stunning views of the grounds. It is perfect for family gatherings, office space or nursery. Adjacent to the dual sink primary bath with a vanity table, there is a winding staircase that leads upstairs to the third floor where you will find a beautifully crafted wardrobe/dressing room with many custom built-ins, lighting and mirrors. This lovely area conveniently leads to an exercise room, powder room and an oversized cedar closet, and this completes the third floor. There are four additional family bedrooms on the second floor, two share a Jack and Jill bathroom, one has its own en-suite, and the fifth bedroom suite offers versatile living space. The fifth bedroom and sitting room, located near the back stairs, welcomes an in-law arrangement, live in nanny, or out of town guests. The full basement offers at least another 2444 square feet of living space and includes a large recreation room with fireplace, billiard room, wet bar, spacious laundry room, large cedar closet, another storage room with built-in shelving, and a powder room. The yard is professionally landscaped, private, and nearly two acres is quite hard to come by in Winnetka. Additional features of this remarkable residence include: a three car, heated, attached garage, magnificent craftsmanship, glorious room sizes, four fireplaces, a slate roof, copper gutters, circular driveway and uncommon privacy. This residence is a true gem in the heart of Winnetka. Live a life of luxury and sophistication in this exceptional home. Woodley Road, with its canopy of mature trees, is a coveted private oasis, and yet is conveniently located near town, train, restaurants, schools and a public golf course. This property is not located in the flood plane. NO SIGN