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Lewisboro, New York Homes for Sale

Lewisboro is a scenic community in the lower Hudson River Valley, just 55 miles from the Heart of New York City. The Town of Lewisboro includes the hamlets of Cross River, Golden's Bridge, South Salem and Waccabuc.

The town was established in 1731 and is named after John Lewis. After purchasing land from the local natives, the first settlers established themselves around South Salem. The town was formed as “Salem” in 1747. By 1790, the town assumed its current dimensions as lands were removed for other towns. The name changed to South Salem in 1806. John Lewis, a financier, requested the town be given his name and established a fund for the town, though he did not follow through on his promise of a railroad link. Lewisboro is noted for its elaborate gardens, most notable in its public traffic triangles. Dry-stone walls and elaborate colonial mansions are other dominant features to the town of Lewisboro.

Unlike the neighboring communities of Katonah and Ridgefield, Lewisboro does not have a downtown business district. The effect this has had on the community has resulted in no "center of town". Most people in town gather and do their shopping at one of the two shopping plazas, in the communities of Goldens Bridge or Cross River. 

There are 7 lakes in the town of Lewisboro. Lake Waccabuc, Lake Oscaleta, and Lake Rippowam are interconnected and are collectively known as the Three Lakes, and are natural (not man-made) lakes. Lake Waccabuc is the largest and most well-known of these, and the area of town named after it has a separate post office. Lake Oscaleta and Lake Rippowam are also called the Twin Lakes, probably because of Twin Lakes Village, a development which runs between them. The other lakes in town are Lake Truesdale, Lake Katonah, Lake Kitchawan, and Timber Lake. Recognizing the importance of the lake communities in the town, in 2007 a Lakes Committee was formed by the Town of Lewisboro.

Ward Pound Ridge Reservation is Westchester County's largest (4,700-acre (19 km2) park. In addition to many trails, there are camping facilities and a Trailside Museum. The main entrance is on Route 121 in Cross River. The Lewisboro Town Park on Route 35 contains tennis courts, the town pool, ball fields, and outdoor basketball courts. When ice skating is available in winter, a sign is posted. There are also some walking trails in this park that connect to the adjacent Ward Pound Ridge Reservation.

The Katonah-Lewisboro School District serves the town of Lewisboro, the northern third of Bedford, including the hamlet of Katonah and portions of the towns of Pound Ridge and North Salem. It has four elementary schools, one middle school and one high school. These are: Katonah Elementary School, Increase Miller Elementary School, Lewisboro Elementary School, Meadow Pond Elementary School, John Jay Middle School and John Jay High School. 

Town of Lewisboro: www.lewisborogov.com
Katonah-Lewisboro School District: www.klschools.org

 

Lewisboro Homes for Sale

$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
$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
$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
$2,395,000
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
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 1016941 MLS
A rare opportunity to own a Silvermine Preserve home where sophisticated design, exceptional craftsmanship and thoughtful technology come together. Engineered as a high-performance home, it incorporates geothermal heating and cooling along with advanced energy-efficient building systems that enhance year-round comfort, efficiency, and long-term value. Set within an exclusive enclave of architecturally distinctive new homes in South Salem, this modern, mid-century inspired residence offers a fresh interpretation of contemporary living. Nestled on a private one-acre site along a gated road, the single-level floor plan embraces clean architectural lines, expansive glass, and a seamless connection to the surrounding landscape. Offering approximately 3,000 square feet, the proposed home features four bedrooms and three-and-one-half baths, with the opportunity to collaborate directly with the builder to personalize interior finishes and selections. Located within the Katonah-Lewisboro School District, this exceptional offering combines architectural sophistication with innovative construction, all within easy reach of shopping, dining, schools, and outdoor recreation.

Lot 6 Sachem Way, South Salem
$1,795,000
3 Beds ⋅ 2 Baths ⋅ 1012484 MLS
RIVERBEND FARM. Remarkable frontage on the rushing Waccabuc River. The original Adams Dairy Farm--an absolutely breathtaking property with level lawns lined by old stone walls, specimen trees and vibrant flowering perennials. Incredible gardens of Daffodils, Tulips, Iris, wild Roses, Lilac, Wysteria, Allium, and Peonies along with fragrant and flowering Magnolia, Apple, and Viburnum. Raised bed, fenced gardens for seasonal produce. A former working farm with Craftsman restored dairy barn, hen house/chicken coop and old icehouse. Rare antique Farmstead dating to 1792. Beautifully scaled room with high ceilings, hardwood floors and vintage millwork. Formal Entrance Hall with front staircase and incredible newel post. Sun-filled front Parlor. Dining Room with fireplace, bay window and door to delightful, covered porch. Spacious Country Kitchen with new appliances and breakfast area incorporating an antique Boyton & Lakewood cooking stove. Warm and inviting Family Room. Second floor with Three Bedrooms, one with en suite Sitting Room with fireplace, Office and Nursery. Spectacular Party Barn with loft and game room, formerly a horse barn, brimming with endless possibilities. Over five spectacular acres. A remarkable offering -- own part of the past!

121 Post Office 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
$1,695,000
3 Beds ⋅ 4 Baths ⋅ 997072 MLS
Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc and lives like four bedrooms (4 bedroom septic). Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic elegance with sophisticated comfort. The dramatic living room is anchored by vaulted ceilings, authentic rustic beams, and a wood-burning fireplace, creating a warm yet refined gathering space. For today’s remote lifestyle, a handsome den/home office with custom paneling and built-ins offers the perfect work-from-home setting. At the heart of the home is the expansive kitchen, uniquely warmed by a double-sided wood-burning fireplace. Entertain effortlessly in the character-filled formal dining room or unwind in the sun-drenched sunroom, which opens directly to the sprawling rear patio and picturesque grounds beyond. A rare and highly sought-after feature, the luxurious first-floor primary suite offers exceptional convenience and privacy, complete with two oversized walk-in closets and a spa-like bath. The second level provides incredible flexibility with two additional bedrooms, two full bathrooms, a dedicated second office, and an expansive playroom or media/recreation space. Experience the quiet luxury of Northern Westchester living in a home that truly has it all.

158 Mead Street, Waccabuc
$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
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