Above $1 Million Winnetka IL Real Estate, Homes, Condos for Sale

4 Beds ⋅ 5 Baths ⋅ 12706253 MLS ⋅ NEW Status

Winnetka

3 Beds ⋅ 5 Baths ⋅ 12715536 MLS ⋅ NEW Status

This is the opportunity buyers wait for. An architecturally significant Hubbard Woods Georgian that could never be duplicated today for anywhere near this cost. Perfectly positioned on one of the neighborhood's most coveted cul-de-sac streets, this distinctive home showcases extraordinary vintage details paired with over $1.2 million in thoughtful renovations and 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!

1192 Chatfield Road, Winnetka

$3,025,000

5 Beds ⋅ 7 Baths ⋅ 12712818 MLS ⋅ CONTINGENT Status

Perfectly positioned in coveted East Winnetka, this exquisite newer-construction stone residence offers timeless elegance, thoughtful design, and over 6,500 square feet of luxurious living across four beautifully finished levels. Upon entering the home, you can almost feel the lake breeze and catch a sight line of Lake Michigan-a reminder of this home's premier location just moments from the shoreline. The stately limestone and stone exterior, crowned by a classic slate roof, creates an unforgettable first impression. Inside, a grand reception foyer welcomes you with soaring ceilings, abundant natural light, and beautifully proportioned living spaces that exude warmth and sophistication. The gracious formal living room, anchored by a handsome limestone fireplace, flows seamlessly into an elegant dining room designed for memorable gatherings. Tucked away for privacy, a richly paneled office with custom built-in bookcases provides the perfect work-from-home retreat or quiet library. At the heart of the home, the expansive family room overlooks the backyard and sports court, creating an effortless connection between indoor and outdoor living. The New Chef's Kitchen offers a generous center island with seating, premium appliances, coffee station and breakfast bar, and a sun-filled breakfast room wrapped in windows that feels like a year-round solarium. A newly added mudroom with custom cubbies and storage provides convenient access to the attached heated garage with epoxy flooring. The second floor offers a beautifully designed center hall layout with new laundry room, four spacious bedrooms, including an exquisite primary suite that serves as a private sanctuary. Complete with dual walk-in closets and a serene spa bath, the suite is designed for ultimate comfort and relaxation. Three additional bedrooms, including two with en-suite baths, provide exceptional accommodations for family and guests. The third floor is a destination all its own-a versatile retreat featuring a spacious bedroom suite, full bath, and a private rooftop sun deck. The fully finished lower level expands the home's exceptional living space with a large recreation room, custom bar, sixth bedroom, and full bath-ideal for overnight guests, a bonus room - ideal for a gym, or extended family living. Outside, the deep and fully fenced backyard is an entertainer's dream. A generous patio invites al fresco dining and summer gatherings, while the sports court provides endless opportunities for recreation and play. All of this is set on one of East Winnetka's most desirable blocks, offering an unbeatable lifestyle just moments from downtown Winnetka, the lakefront, parks, train, and award-winning Greeley Elementary and New Trier High School.

566 Willow Road, Winnetka

$1,395,000

4 Beds ⋅ 3 Baths ⋅ 12705964 MLS ⋅ NEW Status

Winnetka

$1,725,000

5 Beds ⋅ 5 Baths ⋅ 12711173 MLS ⋅ NEW Status

Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront beaches, shopping, restaurants, Metra, Greeley and New Trier East. The quintessential front porch welcomes you to sit and enjoy the view of the park-like lawn. The front entry opens to the foyer connecting the first floor rooms and a striking staircase. Grandly scaled great room sets the tone for the rest of the home, and offers a wonderful space for gathering and relaxing. The formal living and dining rooms echo the same gracious, comfortable style. An updated white kitchen with granite countertops has top appliances and opens to the family room with doors to the deck and paver patio. Second floor includes a stunning primary suite featuring a gorgeous bedroom filled with light, soaring ceilings, two walk-in closets, a luxurious spa bath and a lofted office above. Three additional bedrooms and two renovated baths complete this level. The third floor has treetop views, a bedroom, office and full bath. The lower level features a laundry room, playroom and storage. Very private back yard with two level deck and separate paver patio. Attached heated garage. Property sold "As- Is".

555 Cherry Street, 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

$2,295,000

5 Beds ⋅ 7 Baths ⋅ 12697023 MLS ⋅ PENDING Status

Perfectly situated in the heart of Hubbard Woods, this bright 6 bedroom, 5.2 bath home offers an exceptional combination of timeless architecture, volume and one of Winnetka's most coveted walk to everything locations. Just steps from the Metra, walk to Hubbard Woods Elementary, Hubbard Woods Park, and neighborhood favorites including Mino's, Guanajuato, Spirit Elephant, Grateful Bites, & Graeters to name a few - this is North Shore living at its finest. Extensively renovated to 2026 standards, this home includes a kitchen overhaul with Taj Mahal honed quartzite countertops, full-height quartzite backsplash, an oversized island with seating, storage, an undermount sink, built in microwave drawer, Zephyr beverage refrigerator, updated hardware, and professionally refinished custom cabinetry. Premium appliances include a Sub-Zero fridge, Viking 8-burner cooktop, and Thermador double ovens. The kitchen has a defined area for a breakfast table, French doors with views of the deck and backyard. It flows seamlessly into the family room which features coffered ceilings, oversized windows, and a wood-burning fireplace. Exceptional scale and natural light define the rest of the main level, where 10-foot ceilings and oversized windows flood this home with natural light. A gracious foyer welcomes guests and opens to an elegant living room with a south-facing bay window and fireplace, a formal dining room, a private office with custom built-ins, a beautifully updated powder room, and a newly reimagined mudroom complete with heated floors and custom-designed storage. The second level has four spacious bedrooms, including a luxurious primary suite featuring two professionally designed walk-in closets and a stunning spa-inspired bath completed in 2026. Thoughtfully appointed with dual vanities, heated floors, floor-to-ceiling porcelain tile, an oversized soaking tub, walk in steam shower, and premium finishes throughout - the space offers the comfort and elegance of a luxury retreat. A second ensuite bathroom was completely renovated with a new shower, vanity, fixtures, heated floors, and designer finishes. The walk in laundry room features new quartz countertops, utility sink, refreshed cabinetry, and a new washer. Newly installed hardwood flooring throughout the second level completes the look. The third floor provides exceptional flexibility with a private suite featuring a full bath and walk-in closet, making it ideal as a guest bedroom, teen retreat, playroom, fitness studio, or second home office. The finished lower level has exceptional ceiling height and abundant natural light from four massive windows. This creates a living space that feels like an extension of the main level. Additional highlights include a spacious recreation room with fireplace, 1/2 bath, refreshed wet bar featuring quartz countertops, professionally painted cabinetry, and custom shelving, a generous billiards area, an oversized sixth bedroom with private ensuite bath-perfect for guests, an au pair, or multigenerational living. This exceptional home is move in ready and is three blocks from downtown Hubbard Woods!

1235 Scott Avenue, Winnetka

$1,500,000

4 Beds ⋅ 3 Baths ⋅ 12699325 MLS ⋅ ACTIVE Status

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.

1360 Sunview Lane, Winnetka

$1,799,000

4 Beds ⋅ 3 Baths ⋅ 12704826 MLS ⋅ CONTINGENT Status

Exceptional 4-bedroom, 2.1-bath home on Winnetka's coveted Tree Streets, offering an expansive third-floor loft and situated on a 50' x 187' deep lot. Blending timeless charm with thoughtfully designed living spaces, this home is filled with natural light, soaring ceilings, and beautiful hardwood floors throughout. A welcoming covered front porch leads into gracious living and dining rooms, while the attached extra-deep 2-car garage comfortably accommodates a full-size SUV suburban with direct access to a mudroom and powder room. Designed for both entertaining and daily living, the impressive chef's kitchen features sleek cabinetry, granite countertops, exceptional storage, an oversized island, separate breakfast bar, stainless steel appliances, double ovens, beverage refrigerator, and a sunny breakfast area overlooking the spectacular backyard. The adjacent family room is warm and inviting with custom built-ins, a wood-burning fireplace, and French doors opening to the deck, creating seamless indoor-outdoor living. Upstairs, you'll find four spacious bedrooms, including a stunning primary suite with soaring vaulted ceilings, two walk-in closets, and a beautifully updated spa-inspired bath featuring heated floors, dual vanities, a skylight, soaking tub, and a separate glass-enclosed shower. A private staircase leads to the extraordinary third-floor, complete with a wet bar and offering incredible flexibility as a luxurious primary retreat, home office, or private fitness studio. Vaulted ceilings, skylights, and abundant natural light make this one of the home's most unforgettable spaces. The finished basement provides even more flexible living space with a large recreation room, laundry room, and storage. Additional highlights include dual-zone heating and cooling, a deep attached garage, and a beautifully landscaped, fully fenced backyard with a spacious deck ideal for entertaining, relaxing, and play. All of this is just moments from Crow Island School, parks, downtown Winnetka's shops and restaurants, and the Metra, offering the perfect combination of space, style, and an unbeatable location.

922 Ash Street, Winnetka

$2,699,000

4 Beds ⋅ 6 Baths ⋅ 12690581 MLS ⋅ CONTINGENT Status

Winnetka! This checks all of the boxes! 5 Beds/5.1 Baths. This gorgeous SFH comes with all of the perks. Gourmet kitchen with Sub-Zero/Thermador, large island, walk-in pantry and gorgeous breakfast area that opens to the family room. The first floor office has built-ins and French doors. Step into the formal dining room with beautiful ceiling details and moldings. Relax in the formal living room in front of the fireplace. Incredible primary suite with large his-and-her closets, and luxurious bath. The second floor has 2 additional ensuite bedrooms and a nicely appointed laundry room. The 3rd floor is light-filled and offers a 4th ensuite bedroom. The fantastic lower level has it all: a huge recreation room, 5th bedroom, exercise/theatre room, wine room, golf simulator, and the 5th full bath. Great location near schools, tennis, golf, playfields, and the train. Experience everything Winnetka has to offer.

1050 Spruce Street, Winnetka

$2,899,000

4 Beds ⋅ 4 Baths ⋅ 12688378 MLS ⋅ CONTINGENT Status

792 Walden Road, Winnetka

$3,799,000

4 Beds ⋅ 5 Baths ⋅ 12688040 MLS ⋅ CONTINGENT Status

785 Mount Pleasant Street, 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

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

$2,195,000

6 Beds ⋅ 6 Baths ⋅ 12700587 MLS ⋅ PENDING Status

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

757 Locust Street, Winnetka

$1,779,000

4 Beds ⋅ 3 Baths ⋅ 12683501 MLS ⋅ CONTINGENT Status

Nestled in an exceptional location, this beautifully appointed home offers the perfect combination of charm, comfort, and convenience. Just moments from vibrant downtown Winnetka, you'll enjoy easy access to outstanding restaurants, boutique shopping, the train station, and the beach-making it easy to embrace the very best of the community. Inside, the thoughtfully designed floor plan features spacious living areas ideal for both everyday living and entertaining. The inviting family room and elegant living room each showcase their own fireplace, creating warm and welcoming spaces to gather throughout the seasons. A delightful sunroom fills with natural light and provides the perfect place to relax, while the adjacent breakfast area offers a cozy setting for casual meals. The home includes four generously sized bedrooms and a spacious mudroom conveniently connected to the attached two-car garage, adding functionality to its timeless appeal. Outside, enjoy a wonderful outdoor living space with a beautifully fenced yard that offers privacy and plenty of room for play, gardening, or entertaining. With its unbeatable location, versatile layout, and exceptional amenities, this is a home that truly delivers the lifestyle today's buyers are looking for.

639 Lincoln Avenue, Winnetka

$1,795,000

3 Beds ⋅ 3 Baths ⋅ 12698922 MLS ⋅ ACTIVE Status

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.

180 Westview 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

$3,049,000

4 Beds ⋅ 5 Baths ⋅ 12693763 MLS ⋅ PENDING Status

Inspired by timeless French Eclectic architecture and impeccably built in 2007, this extraordinary residence offers an exceptional blend of architectural character, refined craftsmanship, and modern luxury. Ideally located just blocks from Lake Michigan, top-rated schools, parks, town, and train, the home sits on a beautifully landscaped lot designed for both elegant entertaining and everyday living. From the striking Stone and Limestone exterior and handsome front porch to the custom millwork, exquisite stonework, hardwood floors, and designer lighting throughout, every detail reflects thoughtful design and superior quality. Grand, light-filled living spaces include a chef's kitchen with premium finishes, a spacious family room, formal dining areas, and beautifully appointed private spaces ideal for work or relaxation. The luxurious primary suite is complemented by good sized secondary bedrooms and well-designed living areas across three finished levels. The fully finished lower level offers exceptional versatility with recreation spaces, an exercise room, additional bedroom suite, and spa-inspired amenities including a steam shower and dry sauna. Outdoors, professionally landscaped grounds create a private retreat featuring an inviting patio and lush lawn for seamless indoor-outdoor entertaining. Combining timeless architecture, exceptional craftsmanship, and an unparalleled location in one of the North Shore's most desirable neighborhoods, this remarkable home offers an extraordinary lifestyle defined by elegance, comfort, and enduring quality.

654 Pine Street, Winnetka

$1,795,000

4 Beds ⋅ 4 Baths ⋅ 12678232 MLS ⋅ CONTINGENT Status

Located in the heart of Winnetka and within the highly sought-after Crow Island School District, this impeccably maintained 5-bedroom, 3.1-bath home checks every box. Thoughtfully reimagined and beautifully updated, the first floor offers exceptional flow, abundant natural light and timeless finishes throughout. At the center of the home is the stunning kitchen, completely gutted and renovated in 2022 with top-of-the-line finishes and a thoughtful design. A large island serves as the heart of the kitchen and gathering space, while the chef's appliances and custom high-end cabinetry make it as functional as it is beautiful. The kitchen opens seamlessly to the family room, creating the perfect space for everyday living and entertaining. The screened porch offers great indoor/outdoor living. The first floor also features a gracious dining room, inviting living room, refreshed mudroom, stylish powder room, and exceptional custom millwork throughout. Upstairs, you'll find four spacious bedrooms and two full baths. The oversized primary suite has generous closet space and a beautifully appointed bath featuring dual vanities, a separate shower, and soaking tub. Three additional bedrooms are bright and airy, each with custom closet organizers. The lower level was largely renovated in 2023 and offers incredible additional living space with updated flooring, lighting, drywall, and expanded recreation areas. A fifth bedroom and full bath provide the perfect accommodations for guests, an au pair, or a private home office. The backyard offers great space for entertaining, kids playing and sunshine. The garage is oversized (2.5 spaces) and has extra depth for those suburban mom SUVs. Meticulously maintained and move-in ready, this exceptional home is ideally located just steps from town, train, parks, schools, and everything that makes Winnetka one of the North Shore's most desirable communities.

1037 Oak Street, Winnetka

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 12688534 MLS ⋅ CONTINGENT Status

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

1347 Sunview Lane, Winnetka

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 12687072 MLS ⋅ ACTIVE Status

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.

1110 Elm Street, 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

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 12657695 MLS ⋅ PENDING Status

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

1225 Elm Street, Winnetka

$3,200,000

5 Beds ⋅ 5 Baths ⋅ 12682485 MLS ⋅ PENDING Status

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

48 Indian Hill 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

$3,850,000

7 Beds ⋅ 6 Baths ⋅ 12680669 MLS ⋅ CONTINGENT Status

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

605 Arbor Vitae Road, Winnetka

$2,099,000

5 Beds ⋅ 6 Baths ⋅ 12674124 MLS ⋅ PENDING Status

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

920 Pine Tree Lane, Winnetka

$2,795,000

5 Beds ⋅ 5 Baths ⋅ 12677019 MLS ⋅ ACTIVE Status

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).

127 Glenwood Avenue, Winnetka

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 12673083 MLS ⋅ ACTIVE Status

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.

42 Woodley Road, Winnetka

$7,999,900

6 Beds ⋅ 9 Baths ⋅ 12661112 MLS ⋅ ACTIVE Status

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.

919 Hill Road, Winnetka

$1,700,000

4 Beds ⋅ 4 Baths ⋅ 12629591 MLS ⋅ PENDING Status

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

478 Sunset Road, Winnetka

$4,995,000

5 Beds ⋅ 9 Baths ⋅ 12657418 MLS ⋅ ACTIVE Status

1380 Westmoor Trail, Winnetka

$3,495,000

6 Beds ⋅ 8 Baths ⋅ 12660928 MLS ⋅ ACTIVE Status

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.

1015 Sheridan Road, Winnetka

$4,999,900

6 Beds ⋅ 6 Baths ⋅ 12660037 MLS ⋅ PENDING Status

Generational opportunity...the chance of a lifetime now awaits in one of Winnetka's most premier "off lake" enclave neighborhood...936 Sunset Road with two golden options for this exclusive real estate offering. This extraordinary Ralph Lauren vibe, country ranch is all about casual elegance with a desirable first floor primary suite. Set on a magnificent 1.29 acre lot, this property now INCLUDES a Village approved subdivided .67 acre buildable lot option so you can sell off OR use & expand your dream estate with a second structure with separate service entrance. Inviting presence with circular drive & framed manicured grounds presents a very storybook residence with classic architecture, new composite cedar shake roof, copper gutters, and charming dormers creating unforgettable curb appeal. A welcoming covered front porch sets the tone as you enter the foyer thru the Farrow & Ball French blue doors, brick flooring and Nantucket inspired millwork. This expansive ranch with southern exposure naturally lights up the entire house as the formal living with picturesque windows showcases the breathtaking views of the expansive grounds & tennis court. Just beyond, the spectacular sunroom/family room serves as the heart of the home with panoramic views of the lush backyard and entertaining terraces, creating an effortless indoor-outdoor connection. The dining room offers an intimate yet refined setting for gatherings and leads to the updated classic all white kitchen accented with Carrera marble and designed by notable North Shore architect Chip Hackely. Custom cabinetry accented with huge breakfast bar island with seating for 6 and expansive prep space make this the hub of the house with great views of Sunset Road. An adjoining breakfast area surrounded by French doors overlooks the picturesque property and opens directly to the outdoors. Additional first floor living spaces include an inviting den with vaulted ceilings, custom built-ins, and stone fireplace, offering the perfect retreat for relaxing, entertaining or expansive option to make primary suite larger. Completing the main level is the luxurious first-floor primary suite, a peaceful sanctuary with rolling green views and spa stone bath. The spacious second floor continues with five family sized beds and three updated all white marble baths, including two private ensuite retreats and an additional hall bath. Each bedroom is flooded with light and can also be a perfect place to expand the house if needed. One of the bedrooms is currently being utilized as a sophisticated office space. The lower level offers an exceptional additional living space centered around a large recreation room, kitchenette, laundry center. Enchanting outdoor space with blue stone patios, tennis court and miniature replica playhouse make this property so special as there in incredible opportunity with second lot to elevate to another level of luxury by adding a 20x40 pool with separate tricked out cabana house with wellness gym, golf simulator room, 2nd office and guest quarters. If you rather just live in the house and sell off the back land, that is a fabulous option as well or even live as the house is now and plan for the future, it all works here. This opportunity is one of kind as there are many different ways to optimize 936 Sunset all while being in an A++ location, south of Willow, steps to Crow Island, FCH, and NSCD schools and either way to New Trier or Loyola, plus, don't forget, town and the train are right there too. This is your optimal long term forever house option as there many customized opportunities to make this your own. Either right away or over time, the most important this is that you have SECURED a prime address on the street that falls right behind living on the lake. The ultimate North Shore investment property to be offered in years!

936 Sunset Road, Winnetka

$2,395,000

5 Beds ⋅ 6 Baths ⋅ 12640779 MLS ⋅ CONTINGENT Status

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

1482 Edgewood Lane, Winnetka

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 12604512 MLS ⋅ CONTINGENT Status

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

1208 Oak Street, 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

$4,699,000

6 Beds ⋅ 9 Baths ⋅ 12638690 MLS ⋅ PENDING Status

Magnificent East Glencoe home- approximately 9,000 sf of total finished space. 6 BR all ensuite plus 3 additional half baths. Stone & brick exterior on over .5 acre lot. Close to train. Featuring a spectacular kitchen, media room, cherry library, workout room, sauna, wine cellar, and fully fenced expansive private outdoor living space with fireplace / TV and separate fire pit with seating area and full outdoor kitchen. Perfect yard for a pool and/or sports court. Heated 3-car garage. Smart home with Crestron System. Backup generator. Incredible attention to detail & finishes. A must see!! Glencoe Schools!

231 Woodlawn Avenue, Winnetka

$2,695,000

4 Beds ⋅ 5 Baths ⋅ 12620950 MLS ⋅ PENDING Status

This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move into the living room with marble surround fireplace that is sun-filled and bright. This leads you to the enclosed porch area where you can bask in the sun with walls of windows & surrounded by private, beautiful and mature landscaping. This home truly brings the outdoors inside to you! The dining room is perfect for hosting events and leads to the white eat-in kitchen with an island and double ovens that is very spacious for cooking and entertaining. The kitchen is conveniently located next to the first-floor laundry room. Down the hall from the kitchen is a huge wood beamed ceiling family room with patio doors that open to the outside, a fireplace with granite surround and built-in bookshelves where the media resides. The octagonal office with an oversized vaulted ceiling and is flanked with floor to ceiling windows and beautiful built-in bookshelves. Working from home has never been more relaxing in this serene setting. Take the steps off the family room up to the recreation room where you can play pool, games or watch tv in this amazing playroom area. The functionality of having a large first floor primary suite, with attached bathroom, closets galore, near your own outdoor oasis is spectacular. You are in your own bed and breakfast when sleeping in the first-floor primary suite retreat surrounded by gardens and a bluestone walkway. The second floor has three additional bedrooms and two full bathrooms. With an attached 3 car garage, circular driveway on the property and parking for guests in front of the home, you are ready to host any event at this incredible home. The lower level has storage galore and a wine cellar. This is a very special home that has been well loved for many years on the most incredible and expansive property.

92 Indian Hill Road, Winnetka

$16,900,000

6 Beds ⋅ 10 Baths ⋅ 12600188 MLS ⋅ ACTIVE Status

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

915 Sunset Road, Winnetka

$2,499,900

6 Beds ⋅ 6 Baths ⋅ 12611829 MLS ⋅ PENDING Status

MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 4/24/26! Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal chandelier, greets you to six bedrooms, four full baths, two half baths and over 5,400 square feet of refined living and sophistication. The eat in chef's kitchen features beautiful quartzite countertops with breakfast bar seating, stacked upper cabinets, walk in pantry, and premium appliances, including a Sub-Zero refrigerator, Thermador double oven, Bertazzoni cooktop with hood, and a Bosch dishwasher. The grand family room offers oak hardwood floors, soaring 15-foot vaulted ceilings with skylights, a striking stone wood-burning fireplace, and a wet bar, all overlooking the newer expansive Trex deck that wraps around the concrete inground pool. A west-facing four-season room is filled with natural light and provides views of the stone paver patio-ideal for summer bonfires. The main level offers an executive office with rich wood paneling, decorative sconces, and a built-in bookcase. Additional highlights include a comfortable living room with second gas-start fireplace and floor to ceiling Pella casement windows, a formal dining room, half bath, a first-floor guest suite with a newly renovated ensuite bath, and a well-organized laundry room with cubbies, wash sink, and folding area. Upstairs, you'll find five spacious bedrooms with brand-new carpet and solid-core doors, along with two full baths. The expansive primary suite features dual walk-in closets, individual vanities, a soaking tub, water closet, and an oversized steam shower. The finished basement adds approximately 2,300 square feet of recreation space, complete with built-in surround sound, a full kitchenette, bookshelves, ample storage, and a half bath. The home offers dual-zoned HVAC, a sump pump with battery backup, central vacuum system, a three-car garage equipped with a 220V outlet for electric vehicle charging, a newer asphalt driveway with stamped concrete front steps, freshly painted exterior, landscape lighting, outdoor speakers, and a partially fenced generous yard for backyard activities. Ideally located on the North Shore with easy highway access, this home is served by the highly sought-after New Trier High School and is within walking distance to award winning Marie Murphy Middle School. A true hidden gem of Winnetka!

406 Woodley Woods, Winnetka

$2,799,388

4 Beds ⋅ 6 Baths ⋅ 12573223 MLS ⋅ PENDING Status

510 Provident Avenue, Winnetka

$1,299,000

12472653 MLS ⋅ CONTINGENT Status

Beautiful 21,755 sq. ft lot on quiet cul-de-sac. Lot size 95 x 229. The permitted gross floor area for new construction or rehab is 6,805 sq. ft.

1295 Sunview Lane, Winnetka

$4,950,000

5 Beds ⋅ 7 Baths ⋅ 12283033 MLS ⋅ ACTIVE Status

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

32 Woodley Road, Winnetka

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