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About Lewisboro Homes

Welcome to Lewisboro, a charming town located in Westchester County, New York. With its picturesque landscapes and tight-knit community, Lewisboro offers the perfect blend of small-town charm and modern conveniences.

Nature lovers will appreciate the abundance of outdoor activities available in Lewisboro. From hiking and biking trails to scenic parks and nature reserves, there is no shortage of opportunities to explore the great outdoors. The town's proximity to the Cross River Reservoir also makes it a haven for fishing, kayaking, and birdwatching enthusiasts.

Lewisboro is not just a nature lover's paradise – it also boasts a vibrant cultural scene. Residents can enjoy local art galleries, historic sites, and community events throughout the year. The town's strong sense of community is evident in its bustling farmers' markets, annual festivals, and volunteer opportunities.

Families are drawn to Lewisboro for its top-rated schools, safe neighborhoods, and family-friendly amenities. With a strong focus on education and community involvement, Lewisboro provides an ideal environment for children to grow and thrive.

Whether you're looking to settle down in a peaceful suburban setting or seeking a weekend retreat from the hustle and bustle of city life, Lewisboro has something for everyone. Come discover all that this charming town has to offer – from its scenic beauty to its warm and welcoming community, Lewisboro is truly a place to call home.

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Newest Lewisboro Listings

$1,500,000
3 Beds 3 Baths 1015735 MLS
Fresh, stylish, and thoughtfully designed, this exceptional new construction offers inviting spaces, abundant natural light, and carefully selected finishes. Set within a natural woodland setting, this home is well sited on a corner lot with a circular driveway approach and is nicely set back from the road. A dramatic foyer with clerestory windows welcomes you in, with extended sightlines through the home and an abundance of windows creating a bright, open feel. Light red oak floors, crisp architectural details, and a fresh, timeless palette enhance the interiors. The stunning kitchen features crisp white cabinetry, Taj Mahal quartz countertops and backsplash, stainless steel appliances, a waterfall island, walk-in pantry, Butler's pantry with wine refrigerator, and sliders to the deck. The living room offers a versatile windowed alcove, ideal for a home office, reading nook, or quiet retreat. The vaulted primary suite features dramatic windows, a spa-inspired bath, open walk-in closet with built-ins, and window seat. Two corner bedrooms with windows on two walls share a beautifully finished hall bath. The walk-out lower level provides additional living space with a recreation room, full bath, laundry, walk-in closet, and sliders to a patio overlooking natural rock outcroppings and a separate level area perfect for play or outdoor enjoyment. Located in the highly regarded Katonah-Lewisboro School District and minutes to Meadow Pond Elementary School, New Canaan shops, restaurants, Metro-North, and nearby everyday conveniences.

18 Laurel Road, South Salem

$975,000
4 Beds 3 Baths 1026664 MLS
Nestled on a picturesque road in the heart of South Salem, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect balance of privacy, comfort, and convenience. Lovingly cared for by only its second owner, this exceptional home has been thoughtfully updated over the years while maintaining its warmth and charm. Set amid mature woodlands, the hilltop retreat offers a peaceful backdrop with exceptional privacy while remaining just minutes from everything you need. Designed for both everyday living and entertaining, the light-filled interior features a spacious, flowing layout with oversized windows that fill the home with natural light. The inviting living room is anchored by a cozy fireplace, creating the perfect gathering space, while the generous living areas seamlessly connect to an expansive oversized deck for effortless indoor-outdoor living. Whether hosting friends and family or enjoying a quiet morning surrounded by nature, the outdoor spaces are equally inviting. As the day winds down, unwind on the charming front porch and take in spectacular sunset views. Numerous improvements have been made throughout the years, including a beautifully renovated spa-inspired primary bathroom, an updated first-floor full bathroom, significant mechanical upgrades and many other thoughtful enhancements that provide peace of mind for years to come. The versatile lower level, currently configured as a recording studio, offers endless possibilities and can easily be transformed into a home office, recreation room, fitness studio, playroom, or creative space to fit your lifestyle. Ideally located just minutes from the charming hamlets of South Salem, Ridgefield and Katonah, you'll enjoy convenient access to boutique shopping, award-winning restaurants, wellness studios, parks, golf courses, hiking trails, and year-round recreation. Commuters will appreciate the nearby Katonah Metro-North Station with direct service to Grand Central Terminal, as well as easy access to I-684, I-84, and the Saw Mill River Parkway. Westchester County Airport is approximately 30 minutes away, making business and leisure travel effortless. The home is also conveniently located near highly regarded public schools. Whether you're seeking peaceful country living, an easy commute, or convenient access to vibrant town centers, this exceptional South Salem home offers the best of Westchester County living in one of its most desirable locations.

1 Sabbathday Hill Road, South Salem

$1,550,000
3 Beds 3 Baths 1025934 MLS
Escape to your own private waterfront retreat on Lake Oscaleta! This natural glacial lake offers peaceful scenery and year-round recreation. The updated, 2,226-square-foot lakehouse combines quiet privacy with the warmth of a welcoming lake community. A private dock and sandy shallows provide gradual water entry, creating an ideal place for summer swimming, launching a kayak, fishing or simply relaxing at the water's edge. As the seasons change, the lake becomes a backdrop for boating, brilliant fall foliage, winter ice skating, spring birdwatching, and countless opportunities to reconnect with nature. Entertain outdoors on the slate patio and spacious lawn, or enjoy the ever-changing lake views from inside the home. Life on Lake Oscaleta is more than waterfront living -- it is a rare opportunity to experience the beauty, recreation, and sense of escape that only a lake community can offer. The open-concept kitchen, dining, and living areas are designed to maximize the views, anchored by hardwood floors and a wood-burning fireplace. A primary bedroom, full bathroom, versatile den or study, and second bathroom complete the main floor. Upstairs, a second primary bedroom and adjacent sitting room offer expansive vistas in any season, while a third bedroom and another full bathroom complete the upper level. A practical breezeway connects the home and garage, offering an additional sheltered outdoor space. Downstairs, a large unfinished basement is ready for storage and calls out for a home gym or a future recreation room. Whole-house emergency generator (propane). Katonah-Lewisboro School District, Twin Lakes Village/Two Lake Club HOA. Additional photos to follow... This property will not last—come see it for yourself before it is too late!

56 Twin Lakes Road, South Salem

$2,750,000
4 Beds 4 Baths 1023010 MLS
A rare opportunity to own a custom-designed home in Silvermine Preserve, an exclusive enclave of architecturally distinctive residences in South Salem. Set on 1.33 private acres at the entrance to Sachem Way, this exceptional residence was envisioned by the builder in collaboration with acclaimed architect Teo Siguenza, inspired by the enduring character of the farmhouse and reimagined through a modern-rustic architectural lens. Clean, elegant architecture is paired with earthy, natural materials—including rich stained wood siding, handcrafted stone, iron, and concrete—creating a home that is both timeless and distinctive. Expansive walls of glass fill the thoughtfully designed interiors with natural light and capture peaceful backyard views. Built for exceptional comfort, performance, and sustainability, the home features geothermal heating and cooling, rooftop solar, insulated concrete form (ICF) construction, and premium European triple-pane windows and doors. Thoughtfully designed living spaces include a dramatic great room with fireplace, a beautifully appointed kitchen with breakfast area and terrace access, a formal dining room, an expansive primary suite with dressing room and spa-inspired bath, and a walkout lower level. Located in the highly regarded Katonah-Lewisboro School District, this is a rare opportunity to own a home where inspired architecture, exceptional craftsmanship, and energy-conscious living come together.

Lot 13 Sachem Way, South Salem

$338,159
3 Beds 2 Baths 1022536 MLS
Rare opportunity to own a beautifully updated 3-bedroom, 1.5 bathroom condo in a highly desirable location with the added benefit of reduced property taxes and low common charges, making homeownership more attainable. This move-in ready residence is offering exceptional value for both owner-occupants and investors, as the property may be rented as an income-producing investment, subject to program requirements. Step inside to discover a bright and welcoming interior featuring a renovated kitchen with granite countertops, abundant cabinetry, and modern finishes. Hardwood floors add warmth and character throughout the main living areas, while the spacious layout provides comfortable everyday living with generous-sized bedrooms, ample closet space, additional storage, and plenty of natural light. Whether you're entertaining guests or enjoying a quiet evening at home, this residence offers the perfect balance of comfort and functionality. Ideally located in the award-winning Katonah-Lewisboro School District, the home is just minutes from downtown Katonah and New Canaan, as well as shopping, restaurants, parks, Metro-North train stations, the Merritt Parkway, I-684, and major commuter routes. Enjoy the convenience of nearby recreational opportunities while still being within easy reach of both Westchester County and Fairfield County amenities. This property is part of the Middle Income Housing Program. Purchasers must meet program eligibility requirements

268 Maplewood Drive, South Salem

$2,295,000
3 Beds 5 Baths 1018990 MLS
Gracious Country Colonial! Originally built in 1932 and thoughtfully renovated, this timeless antique Colonial seamlessly blends historic character with modern updates. Offering approximately 2,800 square feet of beautifully appointed living space, the home features hardwood floors, period millwork, abundant natural light, French doors, and nicely proportioned rooms throughout. Former owner Liz Lange engaged noted designer Jonathan Adler to appoint the interior. The chef's kitchen features all Viking appliances, custom cabinetry, marble countertops, a center island with breakfast bar, and provides easy access to the outdoor terrace—ideal for everyday living and entertaining. Expansive, level lawns lead to hidden walking trails at the rear of the property, while a private in-ground pool and cabana create a peaceful outdoor retreat. This home is brimming with charm and distinctive character throughout. Additional highlights include a formal dining room, an elegant living room with a fireplace and custom built-ins, a sweet sunroom, and a versatile den/home office. The second-floor features three beautifully appointed bedrooms, an additional office, and a spacious primary suite with an ensuite bath. Professionally landscaped grounds enhance the property's setting, offering a peaceful and picturesque backdrop. Conveniently located just minutes from the Villages of Katonah and Ridgefield, with easy access to major commuting arteries. This home is located within the award-winning Katonah-Lewisboro School District. This is one you won't want to miss!

137 Boway Road, South Salem

$1,695,000
5 Beds 6 Baths 1020960 MLS
Architecturally distinctive and beautifully connected to its natural surroundings, this custom cedar contemporary offers a refreshing alternative to the traditional colonial. Set on over 4 private acres in the heart of South Salem, the home blends dramatic volume, natural light, privacy, and flexible living spaces designed for modern living. The home’s layout flows easily from one inviting space to the next, creating a comfortable setting for both everyday living and entertaining. A welcoming entry opens to the formal dining room and wet bar, then leads into the heart of the home: a spacious kitchen and great room overlooking the backyard. The kitchen features a Viking range, Sub-Zero refrigerator, generous island, dining area, and an adjoining sitting area with fireplace. Walls of glass and oversized windows bring in beautiful natural light while framing views of the rolling lawn, mature trees, and charming barn beyond. The main level also includes a home office with full bath, as well as a separate guest wing with a bedroom, full bath, and laundry. Just off the entry, the formal living room is slightly elevated and offers hardwood floors, dramatic ceiling height, a wood-burning stove, and French doors to a deck overlooking the grounds. From the living room, stairs lead to the bedroom level, where the spacious primary suite feels like a private retreat with vaulted ceilings, fireplace, oversized walk-in closet, and spa-inspired bath. Three additional bedrooms complete this level, along with spiral stairs to a loft area ideal for a game room, creative space, storage, or secondary office. Above the garage, the private guest quarters offer exceptional flexibility for extended guests, multigenerational living, a refined work-from-home setup, or supplemental income potential. This space includes its own entry, living room, kitchen, two bedrooms, and a full bath. The lower level adds even more usable space with an additional bedroom and bath, home gym, storage, and walk-out access to the yard. Outside, expansive decks and patios overlook the rolling lawn and mature woodland, creating a peaceful setting for entertaining, quiet mornings, or simply enjoying the beauty of the property. A barn adds charm and function for the hobbyist, gardener, or outdoor enthusiast, and the grounds offer plenty of room for a pool. Additional highlights include a three-car attached garage, abundant storage, and numerous recent improvements, including a new roof, refinished cedar exterior, new garage doors, and meticulous maintenance throughout. Located within the Katonah-Lewisboro School District, this special South Salem retreat offers the ideal balance of privacy and convenience, just minutes from Metro-North, Ward Pound Ridge Reservation, local hamlets, shopping, dining, and major commuting routes.

South Salem

$2,499,000
1014508 MLS
Welcome to LaVista Restaurant in South Salem, NY — where a devastating tree fall has given rise to a stunning, extraordinary rebirth of this landmark restaurant. This is a rare and compelling opportunity to acquire both the prime real estate and the thriving business in one seamless transaction. This establishment will be delivered TURNKEY completely ready to open for business upon completion of construction, slated to be November 2026. Set on two acres of exceptional property, the brand-new ENTIRELY REBUILT building showcases impeccable all-new construction and thoughtful design. At its heart lies a new state-of-the-art kitchen equipped with brand-new modern appliances and a powerful hood system. The appointed dining areas comfortably welcome 100+ guests, complemented by a newly designed wine bar and a private VIP/Party Room for exclusive events, celebrations, and corporate meetings and gatherings. Situated on a high-visibility major thoroughfare with thousands of daily passersby, LaVista enjoys unmatched exposure in a desirable Westchester County location on the border of CT, attracting both NY and CT Patrons. A devoted, loyal customer base is already eagerly anticipating the reopening, providing an immediate foundation for strong revenue from day one. The building includes a two-bedroom residential apartment upstairs — ideal for an owner-operator or additional income. Whether you are a visionary restaurateur, seasoned investor, or entrepreneurial buyer seeking a turnkey lifestyle property, this is a rare chance to own a fully rebuilt, move-in-ready destination poised and proven for success. Additional highlights include: Ample on-site parking for over 100 vehicles, an expanded basement offering generous storage and operational flexibility, and an outdoor dining patio. LaVista awaits its next chapter — and the right steward to elevate it to even greater heights.

355 Smith Ridge Road, South Salem

$2,499,000
1014507 MLS
Welcome to LaVista Restaurant in South Salem, NY — where a devastating tree fall has given rise to a stunning, extraordinary rebirth of this landmark restaurant. This is a rare and compelling opportunity to acquire both the prime real estate and the thriving business in one seamless transaction. This establishment will be delivered TURNKEY completely ready to open for business upon completion of construction, slated to be November 2026. Set on two acres of exceptional property, the brand-new ENTIRELY REBUILT building showcases impeccable all-new construction and thoughtful design. At its heart lies a new state-of-the-art kitchen equipped with brand-new modern appliances and a powerful hood system. The appointed dining areas comfortably welcome 100+ guests, complemented by a newly designed wine bar and a private VIP/Party Room for exclusive events, celebrations, and corporate meetings and gatherings. Situated on a high-visibility major thoroughfare with thousands of daily passersby, LaVista enjoys unmatched exposure in a desirable Westchester County location on the border of CT, attracting both NY and CT Patrons. A devoted, loyal customer base is already eagerly anticipating the reopening, providing an immediate foundation for strong revenue from day one. The building includes a two-bedroom residential apartment upstairs — ideal for an owner-operator or additional income. Whether you are a visionary restaurateur, seasoned investor, or entrepreneurial buyer seeking a turnkey lifestyle property, this is a rare chance to own a fully rebuilt, move-in-ready destination poised and proven for success. Additional highlights include: Ample on-site parking for over 100 vehicles, an expanded basement offering generous storage and operational flexibility, and an outdoor dining patio. LaVista awaits its next chapter — and the right steward to elevate it to even greater heights.

355 Smith Ridge Road, South Salem

$849,000
3 Beds 3 Baths 1007931 MLS
Nestled on a private, picturesque 1-acre property, this move-in-ready home offers the perfect blend of comfort, convenience, and natural beauty. Freshly painted throughout, the home features newly refinished hardwood floors that shine with warmth and character. The spacious interior boasts two fireplaces, creating inviting gathering spaces for every season, while a beautiful bay window fills the home with natural light and frames peaceful views. The updated kitchen is equipped with stainless steel appliances, including a recently replaced dishwasher and microwave, making everyday living both stylish and practical. The primary suite offers a generous walk-in closet, and central air conditioning ensures year-round comfort. For added peace of mind, the home is generator-ready and includes a spacious two-car garage. Step outside and enjoy the stunning wraparound two-tier deck, perfect for entertaining, dining al fresco, or simply relaxing while taking in the seasonal water views and serene surroundings. A charming white fence enhances the property's curb appeal and sense of privacy. Ideally located just off Route 35, this exceptional home offers easy access to the Goldens Bridge Metro-North station on the Harlem Line, providing a convenient commute to New York City. The station also offers ample parking, making travel effortless. With its private setting, thoughtful updates, and desirable location, this beautifully maintained home is ready for its next owner to move right in and enjoy. Enjoy Seasonal lake views.

58 Gilbert Street, South Salem

$4,500,000
4 Beds 5 Baths 986698 MLS
Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 4.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for both everyday living and entertaining. High ceilings, unique designer chandeliers, and a marble fireplace framed by expansive windows create a dramatic yet inviting ambiance. The primary suite is a private retreat, complete with a serene seating area, walk-in closet, and spa-inspired bath with soaking tub and his-and-hers sinks. The top-floor laundry room ensures effortless convenience, while the fully finished basement boasts a gym, media/recreation room, full bath, and direct walk-out to a covered patio with speakers and ceiling fans. Outdoors, an entertainer’s dream awaits: a stunning in-ground pool and hot tub with a glass railing, outdoor kitchen, fire pit lounge, and professionally landscaped grounds with Kentucky bluegrass sod and Thuja trees, creating your own private oasis. This home has been extensively updated with new roofing, siding, windows, flooring, systems, and high-end finishes, combining elegance with modern functionality. Every element has been thoughtfully curated to offer a posh lifestyle, flawless entertaining, and refined daily living. Nestled within the prestigious Pine Hill Estates, this home offers access to the highly rated Katonah-Lewisboro School District. Commuting is effortless, with close proximity to major highways and multiple Metro-North stations, providing convenient access to New York City and surrounding areas. Beyond the home's luxurious features, the location offers a wealth of recreational opportunities. Just a short drive away, Ward Pound Ridge Reservation, Westchester County's largest park, provides over 4,300 acres of natural beauty. Enjoy hiking, fishing, and camping amidst scenic landscapes and diverse wildlife. For shopping and dining, Ridge Hill is nearby, offering a variety of retail stores, restaurants, and entertainment options. Additionally, Untermyer Gardens Conservancy and Lenoir Preserve offer tranquil settings for nature walks and exploration. This residence is not just a home; it is an elevated lifestyle of comfort, convenience, as well as curated leisure and recreation. Seize the opportunity to make it yours today!

45 Pine Hill Drive, South Salem

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.