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$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
$599,000
2 Beds ⋅ 1 Baths ⋅ 1041674 MLS
The Perfect Hideaway! Private and Serene, stone terrace. Beautiful landscaping fire pit, pool, dining area and sitting area. Great for al fresco dining intimate or room for all! Must see something special !

43 Laurel Road, South Salem
$759,000
3 Beds ⋅ 3 Baths ⋅ 1040228 MLS
A rare opportunity to own an 1800’s country property in Northern Westchester. Nestled beside Ward Pound Ridge Reservation with views of the Cross River Reservoir, the estate has the look and feel of an Upstate New York retreat. The center hall Colonial retains its original two-sided brick fireplace and 14-inch-wide wood plank floors. Plenty of period charm and natural light throughout the home. What sets this property above the rest is the stunning original stone and timber framed barn. The possibilities are endless. A restorer’s dream! The house is currently configured with two bedrooms and a bath upstairs, another office/bedroom with full bath on main level and a half bath off the kitchen area. Located just minutes from Metro-North and major local highways, the property offers a rare combination of privacy, acreage, and commuter convenience, all in the Katonah-Lewisboro School District.

15 Cross River Road, Cross River
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 1035007 MLS
Step inside Tommy’s Lane, where understated architecture gives way to unforgettable design. From the curb, this timeless transitional Colonial sits quietly on just shy of two flat, sun-drenched private acres with a pool. Open the dramatic custom black glass front doors, however, and the entire experience changes. A dramatic two-story foyer introduces interiors that feel as though Restoration Hardware met a world-class luxury hotel. Sophisticated, glamorous, impeccably tailored, and unlike anything else on the market in South Salem. Every inch of this home has been thoughtfully reimagined with an uncompromising eye for design, craftsmanship, and quality. Everything in the home has been redone, with the owner completing an extensive top-to-bottom renovation in 2025. Rich hardwood floors flow throughout an airy, open floor plan created for both everyday living and effortless entertaining. Custom millwork, designer lighting, and bespoke finishes elevate every space, while the stunning family room is anchored by a beautiful wood-burning fireplace and a custom rich wood bar accented with elegant brass mesh detailing, functioning as both a striking focal point and a true piece of furniture. The chef’s kitchen rivals those found in substantially larger custom estates, featuring premium Sub-Zero refrigeration, a professional gas range, custom cabinetry, and dramatic two-inch-thick quartz countertops. Every selection was made with intention, resulting in a space that is as functional as it is beautiful. The principal suite is a true retreat, evoking the feeling of a boutique luxury hotel. The newly completed marble bath is extraordinary, showcasing brass fixtures, intricate mosaic marble flooring with brass inlay, a seamless glass shower, soaking tub, and refined spa-inspired finishes. A beautifully designed walk-in closet completes the suite. Three additional bedrooms complete the second floor and share a beautifully renovated hall bath finished with the same elevated, hotel-quality aesthetic found throughout the home. The lower level is designed entirely around entertaining. A spacious game room with pool table flows into a dedicated media lounge with theater seating, creating the perfect setting for movie nights or game days. A full wet bar, full bathroom, abundant natural light from windows, and direct access to the garage make this level every bit as practical as it is impressive. Outside, complete privacy surrounds the expansive backyard and large swimming pool, creating the perfect setting for summer gatherings, quiet afternoons, or evenings spent with family and friends. The property feels like a private resort while remaining exceptionally convenient. Perfectly positioned, Tommy’s Lane offers easy access to the Merritt Parkway, is approximately 10 minutes to New Canaan, 15 minutes to Ridgefield, and about 15 minutes to downtown Katonah, placing shopping, dining, and commuting all within easy reach. This is far more than a beautifully renovated home. It delivers the level of design, finish, and amenities typically reserved for much larger custom-built estates, while offering the warmth, comfort, and livability of a true family home. Every space has been elevated, every detail considered, and every finish curated. Move-in ready doesn’t begin to describe it. This home is simply walk-in stylish.

2 Tommys Lane, South Salem
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 1027507 MLS
Tucked away on a tranquil cul-de-sac in the prestigious Town of Bedford, this masterfully reimagined gated home defines the next generation of Bedford luxury real estate. Just a short, convenient jaunt from the energy of Manhattan, 2 Barry Court provides a seamless transition from city living to serene countryside retreat, making it an ideal residence for those seeking fresh air, privacy, and refined relaxation. More than just a home, this is a lifestyle property located near the historic Bedford Village Green, the scenic Bedford Riding Lanes, and the vibrant Katonah boutique district. Set on four manicured acres with mature trees and open sky, the estate invites you to unwind in total tranquility—whether for weekends or for full time living. Designed by revered architect Teo Siguenza and developed by the esteemed Grasso Development Corporation, the residence blends timeless character with modern luxury. Inside, a two-story foyer opens to light-filled, 10’ high living spaces, while a custom chef’s kitchen (with Subzero and Wolf appliances) flow effortlessly into a vaulted family room with a statement stone fireplace. The primary suite offers a private oasis with dual dressing rooms, spa-like baths, and its own sitting room with a fireplace. The home's exterior truly shines: a brand new heated gunite pool with automatic cover, pool cabana with full bath and an expansive bluestone terrace transform the property into a resort-style getaway. With its unique combination of proximity to New York City and complete privacy, this move-in-ready estate is perfectly suited for buyers seeking a luxurious home without sacrificing access to the city.

2 Barry Court, Katonah
$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
$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
$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
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 995187 MLS
Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence. The grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature. Outdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation. The residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in. At the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chef’s kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living. The home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for today’s lifestyle. A screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property. Complete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease. Just minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

127 Boutonville Road, Pound Ridge
$3,250,000
4 Beds ⋅ 5 Baths ⋅ 979591 MLS
The Cross Pond Residence, designed by acclaimed architect Frank Lupo, FAIA, is a rare architect-designed estate set on 3.48 private acres overlooking a large pond in Pound Ridge. Conceived as a series of interconnected structures thoughtfully positioned within the landscape, the property offers a level of design, craftsmanship, and flexibility seldom found in residential architecture. The main residence is organized around dramatic living spaces that embrace the surrounding landscape through expansive walls of glass, soaring ceilings, and carefully framed views of the water and grounds. The primary living area flows seamlessly to dining and kitchen spaces, creating an environment equally suited for everyday living and entertaining. The upper level serves as a private retreat with a spacious primary suite, while the lower level provides additional recreation and gathering space. Complementing the main residence is a fully self-contained secondary living quarters featuring its own living room, dining area, kitchen, bedroom, elevator, and private primary suite. Ideal for extended family, guests, live-in staff, or multigenerational living, it offers complete independence while remaining architecturally integrated with the overall composition. Additional structures include a substantial heated studio building with exceptional flexibility for creative work, hobbies, fitness, collector use, or additional vehicle storage, as well as a detached six-car garage with front and rear access, providing ample space for automobiles, equipment, and storage. Constructed with a level of detail and material quality rarely seen today, the residence incorporates steel framing, glulam beams, commercial-grade window systems, lead-coated copper roofing, standing-seam metal roofing, cedar siding, radiant heating, humidity control, and a hydraulic elevator. The result is a home designed not only for visual impact, but for longevity and performance. The grounds are equally compelling, with expansive lawns, mature trees, exposed rock outcroppings, gardens, and a large pond that serves as the focal point of the property. The landscape was conceived as an extension of the architecture, creating a seamless relationship between built form and nature. For buyers seeking additional outdoor amenities, the property offers attractive opportunities for a future pool installation. Conceptual plans have been prepared illustrating both a garage-side pool pavilion overlooking the pond and a more secluded pool retreat adjacent to the studio building, allowing future owners to tailor the outdoor experience to their lifestyle and entertaining preferences. Published in The New American House 2: Innovations in Residential Design and Construction, The Cross Pond Residence represents a rare opportunity to own an architecturally significant estate where design, landscape, and function exist in complete harmony.

54 Cross Pond Road, Pound Ridge
$2,500,000
6 Beds ⋅ 8 Baths ⋅ 928343 MLS
Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of elegance and ease. Enter through the impressive oversized foyer and immediately sense the grandeur. Sunlight pours through large windows, highlighting the home’s impeccable finishes and thoughtful design. The gourmet kitchen, appointed with granite countertops, opens seamlessly to the expansive living room which is ideal for both intimate gatherings and large celebrations. Additional main level spaces include a formal dining room, front and rear staircases, and a private home office with its own entrance. Upstairs, six spacious bedrooms offer exceptional comfort, each with oversized walk-in closets. Four bedrooms feature en-suite baths, while two share a classic Jack-and-Jill perfect for guests, or multi-generational living. Beautiful stone walls, natural rock outcroppings, lush lawns and wooded landscape frame the outdoor spaces. Relax on the expansive stone patio, unwind in the hot tub, or enjoy quiet evenings in the screened porch. There's even ample space for a pool. A semi-circular drive, 3-car garage, large recreation or game room, home gym, five fireplaces and whole-house generator complete this exceptional offering. Located minutes from Pound Ridge’s charming Scotts Corners and convenient to New Canaan, this home combines country serenity with everyday accessibility to shops and restaurants. A true retreat only 50 miles from Manhattan. Also available for rent at $20,000/month.

11 Lost Nations Road, Pound Ridge

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.