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$3,095,000
4 Beds ⋅ 5 Baths ⋅ 12706253 MLS ⋅ NEW Status

Winnetka
$2,499,000
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
$999,000
3 Beds ⋅ 3 Baths ⋅ 12711054 MLS ⋅ CONTINGENT Status
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!

419 Provident Avenue, Winnetka
$950,000
4 Beds ⋅ 2 Baths ⋅ 12684251 MLS ⋅ ACTIVE Status
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.

979 Vine Street, 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
$950,000
3 Beds ⋅ 2 Baths ⋅ 12697250 MLS ⋅ CONTINGENT Status
Rare opportunity in East Winnetka. Nestled beside a quiet neighborhood park, this beautifully updated 1919 Tudor blends timeless architectural character with thoughtful modern updates in one of Winnetka's most sought-after locations. A scenic path just behind the home provides easy access to the Green Bay Trail, making it an easy walk or bike ride to Hubbard Woods School, the Metra, and downtown Hubbard Woods. From the moment you step inside, you'll appreciate the abundance of natural light streaming through white Marvin windows, creating bright, inviting living spaces throughout. The welcoming living room centers around a fireplace, while the renovated kitchen with newer quartz countertops opens seamlessly to the spacious family and dining rooms. A dramatic wall of windows and door opens to the professionally landscaped backyard and patio, creating an ideal setting for both everyday living and entertaining. The second floor offers three generously sized bedrooms and a beautifully renovated marble hall bath completed in 2021, while an updated full bath on the main level provides added convenience for guests. The freshly painted basement offers flexible space for a home gym, playroom, or additional storage. Extensive recent improvements make this home truly move-in ready, including refinished hardwood floors, fresh interior and exterior paint, and numerous cosmetic updates completed in 2025. Buyers will also appreciate the peace of mind that comes with a complete tear-off roof and HVAC system installed in 2016, along with exterior tuckpointing of both the home and chimney completed in 2023. Outside, the professionally landscaped yard is filled with mature trees and seasonal blooms, creating exceptional curb appeal and year-round beauty. There is also the potential to add a detached garage or porte cochere (buyer to verify with the Village). Low real estate taxes and the unique benefit of access to both the Winnetka and Glencoe Park Districts add even more value to this exceptional offering. Everything you love about East Winnetka is just moments away-from Hubbard Woods School, the Metra, downtown Hubbard Woods, Tower Road Beach, and the Green Bay Trail just steps from your back door-making this a home you'll enjoy from day one.

154 Glenwood Avenue, 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



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