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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
$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
$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
$2,899,000
4 Beds ⋅ 4 Baths ⋅ 12688378 MLS ⋅ CONTINGENT Status

792 Walden 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
$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
$3,850,000
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
$825,000
2 Beds ⋅ 2 Baths ⋅ 12671135 MLS ⋅ CONTINGENT Status
Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning fireplace, an expansive updated kitchen with abundant cabinetry, and a dining area flanked by windows with plantation shutters. A bonus family room with vaulted ceilings and skylights, along with a full bathroom, adds valuable flexibility and completes the main level. Upstairs, you'll find two bedrooms with hardwood floors and a shared hall bath. The finished basement offers even more living space, featuring a second fireplace, a wall of closets, and a utility room with additional storage. Step outside to a picturesque, professionally landscaped garden with two patios and plenty of space for relaxing or entertaining. From its inviting curb appeal to its surprisingly spacious interior, this home strikes the perfect balance between charm and function. Timeless details and thoughtful updates are complimented by a versatile layout designed for comfortable everyday living and effortless entertaining.

376 Rosewood Avenue, Winnetka
$975,000
4 Beds ⋅ 4 Baths ⋅ 12617031 MLS ⋅ CONTINGENT Status
Prepare to be captivated by this picture-perfect 4-bedroom, 3.1-bathroom colonial-cottage home, meticulously updated with high-end designer finishes throughout. Boasting incredible curb appeal with its deep blue siding, crisp white trim, and brick-paver paths, this turn-key residence seamlessly blends historic architectural character with contemporary luxury. Inside, an airy, light-filled layout features pristine hardwood flooring, clean architectural lines, and an adaptable floor plan. The heart of the home is the stunning new kitchen, showcasing custom sage-green shaker cabinetry, durable stone countertops, a timeless white farmhouse sink, and high-efficiency stainless steel appliances. The kitchen overlooks the rear living space, where sliding glass doors offer a clear view and effortless access to the private rear entertainment deck. The upper levels house a spectacular primary retreat, designed as a private sanctuary. The primary bathroom offers a true spa experience with its freestanding soaking tub, walk-in shower, expansive double vanity, and a massive skylight overhead. The remaining three bedrooms feature charming sloped cottage ceilings, bright windows, and classic millwork. A second beautifully renovated hall bath showcases a sophisticated, moody color palette, a premium marble vanity, and an integrated skylight. Additional living and recreation space awaits in the finished lower level, anchored by a cozy electric fireplace is ideal for a family room, home theater, or private office. The laundry room, a wine closet, an enormous storage room, third fill bathroom and a craft room round out the flexible basement level. Outside, enjoy a detached 1-car garage and low-maintenance landscaping. Nestled in a premier neighborhood, this home offers unparalleled convenience with its close proximity to town, the train, and local schools. A masterful combination of sophisticated design and everyday functionality!

882 Willow Road, 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
$4,999,900
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
$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
$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
$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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