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South Salem, New York Homes for Sale

South Salem is a hamlet within the town of Lewisboro. 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 that 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.

Within the town of Lewisboro, there are 7 lakes. 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. The Hamlet of South Salem has in its center a Post Office, Town Hall, Library and recycling center.

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: http://www.klschools.org/

South Salem Homes for Sale

$4,395,000
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
$3,500,000
1028341 MLS
Gas Station & Auto Repair Business AND PROPERTY 1.7839 ACRES for Sale! Rare opportunity to acquire a highly profitable, well-established gas station with a strong reputation in the affluent Northern Westchester market. Located on highly traveled Smith Ridge Road, this successful business has built a loyal customer base over many years and is known for its exceptional service and dependable operations. The property features a thriving fuel business along with a well-known foreign and European auto repair shop that generates consistent repeat business and referrals. The experienced repair operation provides a stable and diversified income stream in addition to fuel sales. There is significant upside potential for a new owner through increasing repair capacity, or adding convenience store offerings. This is an ideal opportunity for an owner-operator, mechanic, or investor seeking a turnkey business with immediate cash flow and long-term growth potential. Property Highlights: Established, highly profitable gas station Prime Westchester County location Well-known foreign & European auto repair business Strong reputation with loyal, repeat clientele Multiple revenue streams from fuel sales and automotive services Excellent opportunity to increase revenue through expansion Turnkey operation with proven financial performance Financials available to qualified buyers

390 Smith Ridge 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
$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
$2,250,000
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
$1,999,000
3 Beds ⋅ 5 Baths ⋅ 1044320 MLS
Situated on 2.23 pristine acres near New Canaan, Pound Ridge, and Ridgefield, 6 Briscoe Road is a 4,482-square-foot turnkey Colonial - that lives like a 4 bedroom home - masterfully pairing timeless architectural integrity with modern mechanical excellence. Quality construction and refined finishes define the interior, with 10-foot ceilings, extensive millwork, raised paneling, crown molding, custom cabinetry and oversized true-divided-light windows. The gourmet kitchen is equipped with a 6-burner Viking range, Sub-Zero refrigerator, dual Bosch convection oven, custom cabinetry, and a walk-in pantry. The primary suite offers a serene retreat featuring corner windows, detailed moldings, and a spa-caliber marble bath with a soaking tub and walk-in shower. Two upper levels host flexible living, including a dedicated media room/gym, and a private third-floor guest suite with a full marble bath and lounge. Outdoor living centers on a heated Gunite saltwater pool with a brand-new electric cover, refreshed bluestone patio, and lush level lawn with split rail fence with deer-fence extension. Complete peace of mind is ensured with all-new electrical panels, new windows, a whole-house Generac generator, four-zone AC, a Level 2 EV charger in the oversized 3-car garage and enhanced security. Approximately 10 minutes from the New Canaan train station. Convenient to premier shopping, dining, schools, hiking and entertainment. A true oasis of privacy, craftsmanship, and resort-style living, this remarkable turnkey property is ready to be enjoyed from day one!

6 Briscoe Road, South Salem
$1,999,000
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
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 1033318 MLS
Stunning, one-of-kind, octagonal lakefront residence on Truesdale Lake, with 4 bedrooms, 3.5 bathrooms, 2-car garage, breathtaking lake views, custom rustic décor, open floorplan, vaulted ceilings, custom woodwork, wide plank flooring, built-in bar, interior stone fireplace, wrap-around decking, on .57 acres. Don’t miss out on this opportunity!

33 Truesdale Lake Drive, South Salem
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 1038545 MLS
Welcome to 21 Twin Lakes Road — a stunning, complete renovation that is as close to new construction as you'll find. Every detail has been thoughtfully reimagined, from the sun-filled open floor plan to the gorgeous authentic reclaimed beams that give the home instant character and warmth. A separate 1st floor bonus room and finished basement offers flexible space for a home office, playroom, or gym, and the convenience of first-floor laundry makes everyday living effortless. Location is everything, and this one delivers: a highly sought-after neighborhood that offers direct lake access just across the street, where you'll find a playground, a small beach, and easy launch access for your kayak or paddle board. Whether you're starting your morning with coffee on the water or unwinding after a day on the lake, this home offers a rare blend of turnkey renovation and lakeside lifestyle. Move right in and start making memories at 21 Twin Lakes Road — don't miss this one.

21 Twin Lakes Road, South Salem
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