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45 Pine Hill Drive, South Salem
$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

390 Smith Ridge Road, 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

Lot 13 Sachem Way, South Salem
$2,950,000
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

355 Smith Ridge Road, 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

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

Lot 6 Sachem Way, 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

137 Boway 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

292 Smith Ridge Road, South Salem
$1,899,000
4 Beds ⋅ 5 Baths ⋅ 1055338 MLS
A truly special country estate awaits its next chapter. Set back on a circular driveway and nestled on more than 8 level acres, this Georgian Colonial offers an opportunity to make a remarkable property your very own. An elegant two-story entry features a curved staircase, transom and clerestory windows. The 4-bedroom, 4 1/2-bath home lives like a 5-bedroom, features oversized rooms, high ceilings and beautiful proportions. Three fireplaces, a paneled library, French doors, wide-plank floors, handsome millwork and pocket doors with brass hardware reflect the home's timeless character. A country eat-in kitchen with terracotta floors, exposed beams and a cozy lounging area anchored by a fireplace is perfectly suited to everyday living and entertaining. A heated four-season sunroom with a vaulted ceiling opens to the bluestone patio. The guest wing provides additional flexibility. Outdoors, a Shoreline gunite pool, mature trees, meadows, stone walls, gardens and established plantings create a beautiful country setting. Conveniently located to Ridgefield, New Canaan and Pound Ridge for local shopping, dining, schools, hiking and entertainment. A rare opportunity to restore and reimagine a distinctive country property with exceptional character, acreage and setting.

292 Smith Ridge Road, South Salem

21 Twin Lakes Road, South Salem
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 1038545 MLS
Introducing you're new lake house, 21 Twin Lakes Road — a stunning, completely transformed high-end 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 and marble countertops that give the home instant character and warmth. A separate 1st floor bonus room along with a finished basement offers flexible space for a home office, playroom, or gym, and the convenience of first-floor laundry makes everyday living effortless. A home you truly need to see in person to appreciate the design and craftsmanship. Location is everything, and this one delivers: a highly sought-after neighborhood that offers direct lake access just steps away, where you'll find a playground, a private beach, and easy launch access for your kayak or paddle board. Whether you're starting your morning with a neighborhood walk or unwinding after a day on the lake, this home offers a rare blend of turnkey renovation and lakeside lifestyle.

21 Twin Lakes Road, South Salem

31 Dingee Road, South Salem
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 1055167 MLS
Privacy, space and versatility come together at this special South Salem property set on nearly 8 beautiful acres. This distinctive Colonial/Contemporary offers approximately 3,319 sq. ft. in the main residence with 3 bedrooms and 2.5 baths, plus a beautifully updated legal accessory apartment about 680 sq ft above the three-car garage. Step inside to a dramatic, light-filled interior featuring soaring two-story ceilings, hardwood floors and an impressive open second-floor gallery overlooking the living space below. An abundance of windows brings in natural light and showcases the peaceful wooded surroundings. The spacious eat-in kitchen features wood cabinetry and granite countertops, while the inviting family room with fireplace and sliders to the deck provides a wonderful setting for gatherings. A formal dining room, den/home office, powder room and convenient first-floor laundry complete the main level. Upstairs, the spacious primary suite features a renovated spa-like bath with a claw-foot soaking tub, radiant heat floors, double sinks and walk-in shower, along with two additional bedrooms and an updated hall bath. The partially finished basement provides additional flexible space plus plenty of storage. A standout feature is the updated legal accessory apartment above the three-car garage, offering one bedroom with Murphy bed, kitchen, living room, full bath, washer and dryer, wood-burning stove, loft and its own wonderful open upper deck—ideal for extended family, guests or other permitted uses. The home has also benefited from numerous recent improvements, including a replaced roof, newly painted interior and exterior, repaved driveway, refinished hardwood floors, updated bathrooms, making it ready for its next chapter and new owners. Outside, enjoy nearly 8 private, partly wooded acres with expansive space for outdoor living and recreation. A long forgotten Har-Tru tennis court offers the opportunity to be restored, creating the potential for your own private tennis or pickleball retreat. Multiple decks provide inviting spaces to entertain, relax and enjoy the surrounding natural beauty. Convenient to Ward Pound Ridge Reservation, Katonah-Lewisboro schools, shopping, town and major commuting routes, this unique property offers an exceptional combination of acreage, privacy, dramatic architecture, flexible living space and recreational potential. A rare South Salem offering with room to live, work, entertain and enjoy the outdoors—all in one remarkable setting. Make this your home today.

31 Dingee Road, South Salem

37 West Lane, South Salem
$1,650,000
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.

37 West Lane, South Salem

196 Smith Ridge Road, South Salem
$1,498,000
4 Beds ⋅ 4 Baths ⋅ 1057559 MLS
This Farmhouse Homestead has it all; inviting, spacious and well-proportioned rooms that flow seamlessly from one to the next, offering places to gather, spaces to unwind, and spots to reflect. As the outside beckons from every window, step through the veranda inspired screened-in porch or traipse onto the back deck and the whimsical magic of this property quickly unfolds. Mature plantings, meandering pathways, perennial gardens, and a field of dreams makeup these park like grounds. Offering 4 Bedrooms and 3.5 Baths, Office and Bonus Room, on over 2 acres, situated within the Katonah-Lewisboro School District with easy access to New Canaan CT, Ridgefield CT, minutes to Onatru Farm and an easy commute to NYC, this peaceful sanctuary is a fairy-tale awaiting its next chapter.

196 Smith Ridge Road, South Salem

2 Tommys Lane, South Salem
$1,398,000
4 Beds ⋅ 4 Baths ⋅ 1035007 MLS
2 Tommy’s Lane in South Salem, New York, is a fully renovated four-bedroom transitional Colonial set on just shy of two flat, sun-drenched private acres with a large swimming pool. Completed in 2025, an extensive top-to-bottom renovation combines custom millwork, designer lighting, luxurious bathrooms, and a chef’s kitchen with an open floor plan designed for comfortable everyday living and entertaining. Custom black glass front doors open to a dramatic two-story foyer, introducing interiors that blend the warmth of Restoration Hardware with the sophistication of a boutique luxury hotel. Rich hardwood floors flow throughout the main living spaces. The family room features a wood-burning fireplace and a custom rich wood bar with brass mesh detailing, creating an inviting setting for quiet evenings and gatherings. The chef’s kitchen features Sub-Zero refrigeration, a professional gas range, custom cabinetry, and two-inch-thick quartz countertops. Thoughtfully selected materials and finishes bring together practical function and distinctive design. The second-floor principal suite includes a beautifully designed walk-in closet and a newly completed marble bathroom with brass fixtures, mosaic marble flooring with brass inlay, a seamless glass shower, and a soaking tub. Three additional bedrooms share a beautifully renovated hall bathroom with the same refined finishes found throughout the home. The finished lower level offers a spacious game room with a pool table, a dedicated media lounge with theater seating, a full wet bar, and a full bathroom. Windows provide natural light, while direct access to the garage adds everyday convenience. Outside, the expansive private backyard and large swimming pool create a resort-like setting for summer entertaining, outdoor relaxation, and time with family and friends. Nearly two acres of flat grounds offer space to enjoy the property’s sunshine and privacy. Located in South Salem in Northern Westchester County, 2 Tommy’s Lane offers convenient access to the Merritt Parkway. Approximate driving times are 10 minutes to New Canaan, Connecticut, 15 minutes to Ridgefield, Connecticut, and 15 minutes to downtown Katonah, New York, providing access to shopping, dining, and commuting options. With its 2025 renovation, four bedrooms, designer interiors, finished entertainment level, private acreage, and swimming pool, 2 Tommy’s Lane delivers thoughtfully finished living inside and out. More than move-in ready, this home is walk-in stylish.

2 Tommys Lane, South Salem

18 Laurel Road, South Salem
$1,295,000
3 Beds ⋅ 4 Baths ⋅ 1065858 MLS
Nestled among the trees in a peaceful, serene setting, 18 Laurel Road welcomes you home with a rare sense of quiet and seclusion. Designed and crafted with genuine care and meticulous attention to detail, this brand-new residence thoughtfully merges modern luxury with the natural beauty of its surroundings. Arriving via one of two dedicated driveways—one complete with a convenient and elegant circular driveway— the home’s clean architectural lines and attached garage offer an immediate impression of ease and everyday convenience. Step inside, and you are immediately greeted by a flood of natural light pouring through magnificent, oversized windows that frame the vibrant, shifting colors of the trees outside like living works of art. Every room offers picturesque views of the tranquil landscape, seamlessly connecting the warmth of indoor living with the serenity of the outdoors. At the heart of the home, an open and inviting layout flows effortlessly, centered around a kitchen featuring an expansive walk-in pantry that keeps modern living organized and effortless. The home’s intuitive floor plan adapts to your lifestyle, offering three to four spacious bedrooms, four bathrooms, and a dedicated office or playroom where working from home is inspired by peaceful woodland views. On the lowest level, a bright, finished walk-out space complete with its own full bath extends your options even further—creating an ideal private setting for an au pair, in-law suite, or a recreation room that steps directly out into the fresh air. Outside, the private grounds provide a tranquil sanctuary to unwind, entertain, or simply take in the quiet surrounding nature. Combined with generous storage throughout and a prime location just seven minutes from the train, 18 Laurel Road delivers a lifestyle where quality craftsmanship, inspiring window views, modern comfort, and peaceful privacy meet.

18 Laurel Road, South Salem

145 Smith Ridge Road, South Salem
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 1064566 MLS
Nestled into nearly two acres of park-like property in South Salem, every inch of this expansive lot is 100% usable! Newly renovated top to bottom with an inviting open layout and custom high-end finishes throughout. IMPORTANT TO NOTE: HOUSE LIVES LIKE A 4 BEDROOM HOME WITH 3,100 sqft of FINISHED living space (reference floor plans as needed). Sleek hardwood floors and sophisticated millwork complement a redesigned kitchen with quartz countertops, marble backsplash and brand-new appliances. Brand new bathrooms feature wainscoting and updated fixtures throughout. Full finished basement with access to patio provides additional 750 square feet of living space to represented 2,282 with a built-in office nook and an elegant country laundry room with butcher-block countertops, cabinetry and a utility sink. The second level offers multiple use cases with potential rent roll to offset mortgage or cover tax bill in entirety! Currently lives as an accessory apartment with its own private entrance but offers a fantastic flex space for an in-home office, gym/yoga studio, or a place to house your guests. an expansive living area overlooking the grounds. The space boasts a fully renovated kitchen with quartz countertops and marble backsplash, new appliances, sleek modern farmhouse full bath, laundry hookups and a newly installed electric heat-pump system for independent central heating and cooling. Exterior truly pristine. Stone walkways and elegant masonry throughout, a new Trex stair deck, generous patio space with an expansive sitting wall adds additional outdoor living space, natural stone fire-pit patio with seating area, Belgian-block edging and custom outdoor lighting provide ample room for entertaining friends and guests. Mechanical improvements include a new roof, new siding, new gutters and French-drain system, new well/pressure tank, new plumbing, new electrical and a fully operational whole house standby generator. This house is BETTER THAN NEW. Come on down and see for yourself.

145 Smith Ridge Road, South Salem

29 Hoyt Street, South Salem
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 1059751 MLS
Enjoy the best of Lake Truesdale lifestyle from this beautifully updated contemporary, privately perched on an elevated setting with seasonal lake views and deeded lake rights. Vaulted ceilings, exposed beams and hardwood floors create an airy, inviting interior designed for both everyday living and entertaining. The flexible floor plan lives like a four-bedroom and includes two dedicated offices, multiple gathering spaces, a cozy fireside den and additional finished space on the lower level. Thoughtfully updated throughout, the home features renovated baths, newer appliances, stylish wallpaper and finishes, fresh interior and exterior paint, Serena and Lily lighting and a custom mudroom for easy trips to/from the lake. Outside, a large fenced backyard is framed by mature landscaping, hydrangeas and natural stonework, with plenty of room to play, entertain or simply unwind. Best of all, Lake Truesdale is just moments away, offering swimming, kayaking, paddling and a private association beach with picnic areas and kayak storage. Enjoy the relaxed feel of a lake retreat while remaining convenient to Katonah, Cross River and Ridgefield for shopping, dining, theater and everyday necessities. Located in the Katonah-Lewisboro School District, this is a home that makes every season feel like a getaway. Showings start Thursday 10/15

29 Hoyt Street, South Salem

42 Gilbert Street, South Salem
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 978344 MLS
A special opportunity to own a piece of Westchester's sought after private lake communities! Beautifully sited on 83 acre Lake Truesdale. It has a large deck and dock overlooking the water, along with a private driveway. This 1930 antique colonial is full of character - beamed ceilings, a fireplace and glass doors opening to a deck built for lakeside living. The spacious living room with fireplace/dining room combo offers a wonderful layout to reimagine. Bring your vision and updates to transform this classic retreat into your dream home. Residents enjoy swimming, fishing, boating (electric motors only), sailing, paddle boarding and kayaking in warmer months, and ice skating and ice fishing in winter. All this and a private beach! Convenient to schools, shopping and town park. Ideal for full time living or a weekend getaway, this is a canvas ready for it's next chapter.

42 Gilbert Street, South Salem

72 East Street, South Salem
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 1060291 MLS
Welcome to 72 East Street, South Salem! Discover the perfect blend of comfort, charm, and convenience in this spacious 2-bedroom, 1.5-bath home, offering 2,059 square feet of inviting living space. Nestled along a peaceful street in the highly desirable Katonah-Lewisboro School District, this lovely residence offers a tranquil setting while keeping you just minutes from I-684, the Merritt Parkway, and the shopping, dining, and everyday conveniences of Oakridge Common. Thoughtfully updated, this home combines modern touches with warmth and character, creating an inviting atmosphere perfect for comfortable everyday living and effortless entertaining. Enjoy the serenity of South Salem while benefiting from easy access to major commuting routes and nearby amenities. A wonderful opportunity to enjoy the best of South Salem living!

72 East Street, South Salem

1 Sabbathday Hill Road, South Salem
$965,000
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

30 Main Street, South Salem
$899,000
4 Beds ⋅ 3 Baths ⋅ 1037013 MLS
Rich in history and brimming with charm, this delightful 1827 Colonial is nestled in the heart of South Salem’s historic hamlet, within the award winning Katonah Lewisboro School District. Offering 2,020 square feet of living space, this 4 bedroom, 2.5 bath home beautifully blends timeless architectural character with modern comforts. At the heart of the home is a beautifully renovated kitchen, thoughtfully designed for everyday living and entertaining. Exposed beams, wide plank pine floors, fireplace, charming architectural details and inviting living spaces create a wonderful sense of warmth and character throughout the home. Additional highlights include central air conditioning, a convenient mudroom and a detached two car garage. Outdoors, a private deck overlooks a picturesque landscape of mature specimen trees and established plantings, creating a lovely setting for relaxing or welcoming guests. Set on approximately one third of an acre, this enchanting property captures the beauty, history and enduring appeal of South Salem, with convenient access to Katonah Village and its Metro North train station, Ridgefield, CT, and major highways providing easy travel north and south.

30 Main Street, South Salem

9 Laurel Road, South Salem
$894,999
4 Beds ⋅ 2 Baths ⋅ 1036838 MLS
Welcome to 9 Laurel Road, a spacious home set on 1.5 acres along a quiet residential street in the desirable South Salem area. Surrounded by mature trees and wooded views, the property offers a peaceful setting with plenty of privacy, a generous lawn, and expansive backyard space. The home features 4 bedrooms, hardwood floors, a spacious living room, dining area, eat-in kitchen, and a comfortable family room. The flexible layout on the second floor offers many additional options, including a home office, study, or guest room. The lower level offers ample space for storage, recreation, a workshop, or future use. The attached two-car garage comfortably accommodates two vehicles with plenty of additional space. Conveniently located with local restaurants, grocery shopping, and everyday amenities just down the road, you can enjoy the privacy of a quiet, wooded setting while remaining close to everything you need.

9 Laurel Road, South Salem

92 East Street, South Salem
$849,000
2 Beds ⋅ 2 Baths ⋅ 1064764 MLS
SOPHISTICATED COUNTRY HOUSE. Open, loft-like spaces with high ceilings and exceptional light. Spacious two bedroom home that lives like three. Beautifully renovated Country House with approximately 2070 square feet of sun-filled living space. Spectacular Great Room with high ceiling for dramatic entertaining. Open living and dining areas with doors leading out to the lawn. Skylit Kitchen. Warm and inviting Family Room with fireplace and doors out to rear terrace. Private Primary Suite with Walk-in Closet and Bath. Additional Bedroom plus Office/Nursery sharing Hall Bath. Lower Level Recreation Room. Over two acres in the heart of South Salem. Gorgeous grounds with large expanse of level lawns, old stone walls, age-old trees and specimen shrubs. Conveniently located with easy access to Vista, Ridgefield, Wilton and New Canaan. Quick drive to the Merritt Parkway and Metro North train. Katonah-Lewisboro Schools. An incredible offering!

92 East Street, South Salem

230 Lakeside Drive, South Salem
$599,000
2 Beds ⋅ 2 Baths ⋅ 1032550 MLS
Gorgeous, updated, two bedroom townhome that lives like a three bedroom! The light-filled, living area features a wood-burning fireplace and flows seamlessly into the recently renovated large eat-in kitchen. Perfect for entertaining, the kitchen boasts stainless steel appliances, an oversized center island, and sliders to the deck. The main level also includes a spacious primary suite with an en-suite bath, a second bedroom, a full hall bath, and laundry. A newly installed main staircase leads to the upper level, where you'll find a versatile loft/den space and a skylit office with a door and a closet, providing flexible space for work or guests. Updates completed within the past few years include the hot water heater, HVAC system, windows, flooring, bathroom vanities, and kitchen appliances. Residents of the Oakridge Community enjoy two recently refurbished outdoor pools, new tennis and basketball courts, and a playground. This property also includes two assigned parking spaces. A Detached One Car Garage, right next to the unit, is available separately. Walking distance to shopping and dining at Oakridge Commons and just minutes from New Canaan, Ridgefield, and Katonah. Part of the award winning Katonah Lewisboro School District.

230 Lakeside Drive, South Salem

225 Lakeside Drive, South Salem
$349,000
1 Baths ⋅ 1059419 MLS
Imagine coming home to a beautifully updated studio loft in Oakridge Condos. From the moment you enter, soaring cathedral ceilings, rich hardwood floors, and abundant natural light create an inviting sense of space. The stunning living room is anchored by a Carrara marble fireplace with a custom mantel, complemented by elegant chair rail and picture frame moldings. Just beyond, a private balcony offers a peaceful retreat. The spacious kitchen is designed to impress, featuring stainless steel appliances, diamond quartz countertops, and pendant lighting above a welcoming peninsula dining area. Above the main living space, an expansive loft with picturesque lake/pond views offers endless possibilities for relaxation, creativity, or a home office. The beautifully finished bathroom features travertine tile, while an oversized in-unit washer and dryer provide everyday convenience. Three double closets and two additional main level closets offer exceptional storage. Ideally situated near New Canaan and Ridgefield, CT, with convenient access to the New Canaan train station, this home places recreation and entertainment within easy reach. Explore the scenic hiking trails of Leon Levy Preserve, approximately 3.5 miles away, enjoy the ball fields and community garden at Onatru Park. More than a place to call home, this is a lifestyle that brings comfort and convenience together.

225 Lakeside Drive, South Salem

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