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$1,995,000
3 Beds ⋅ 3 Baths ⋅ 1046466 MLS
9 Lewis Road is the most charming country compound in Pound Ridge. Tucked behind a white gate this completely fenced stone -and-shingle home is privately set on nearly three beautifully landscaped acres and offers a rare combination of character, privacy, and move-in-ready appeal. This jewel-box property welcomes you through a lovely foyer into a spacious living room with oversized windows and views of the gardens and pool—an inviting setting for entertaining. At the heart of the home, the country kitchen, breakfast area, and family room flow seamlessly together, creating a warm and comfortable gathering space. The family room features a wood burning fireplace and high ceilings with beams. The homes kitchen is thoughtfully appointed with a classic blue AGA stove, adding both character and functionality. Rich wood floors, sun-filled rooms, and lots of windows off the family room offer lovely views of the green, private property and create an effortless connection between the interior and surrounding grounds. The main level also features a spacious primary bedroom with high ceilings, new custom California closets and french doors opening to a private terrace. Attached is a beautiful primary bath with a soaking tub, spa like shower and heated floors. An additional room is ideally suited for a home office or nursery. The finished lower level includes a cozy sitting room, two comfortable guest suites and a newly renovated shared bath, offering family and guests a private retreat. The outdoor spaces are equally impressive, with stone terraces, bluestone patios, a beautiful pool, mature landscaping, and ample room for gardens, all set against a backdrop of peaceful wooded privacy. A recently renovated, separate two-bedroom cottage provides exceptional accommodations for guests, extended family or rental income. With a tenant in place till August 2027 providing immediate rental income. When the the current tenancy ends, continue it as an income producing rental or imagine what you might want this special little bungalow to become for your own life. Private, picturesque, and full of character, this special property captures everything buyers love about life in Northern Westchester. Perfect for full-time living, or as a quiet escape from NYC, it offers a wonderful sense of privacy and ease. From the moment you arrive through the front gate, it feels like home. *Listing imagery (interior & exterior) includes digitally curated design enhancements.

9 Lewis Road, Pound Ridge
$7,950,000
10 Beds ⋅ 15 Baths ⋅ 1035246 MLS
MILLSBROOK. Foremost Upper Hook Road estate area. Sophisticated and refined Country House, circa 1938. Beautifully proportioned rooms impeccably appointed by renowned designer. Gleaming hardwood floors, impressive millwork, upholstered walls, French doors and three fireplaces. True Center Hall Entry with French doors to rear terrace. Stunning Living Room with crown dentil molding, bay window and fireplace. Mahogany Library with fireplace and Onyx wet bar. Formal Dining Room. Spectacular Chef’s Kitchen with Breakfast Area. Family Room with coffered ceiling and fireplace. Private First Floor Primary Suite with opulent Bath. Five additional Bedrooms. Lower Level with Professional Home Theater, Wine Cellar and Home Office Suite. Two Bedroom Guest/Caretakers House with Gym. Olympic length Swimming Pool. Fabulous stone and Mahogany Pool House with fireplace. Gated drive to over seven manicured acres. Gently rolling lawns, exquisite gardens, old stone walls and scenic, babbling brook. A truly rare opportunity!

29 Upper Hook Road, Katonah
$925,000
4 Beds ⋅ 4 Baths ⋅ 1045301 MLS
Lake days. Dinner reservations. The best of both worlds. This updated 4-bedroom, 3.1-bath Colonial offers 2,924 square feet and the relaxed rhythm of Truesdale Lake, just minutes from the restaurants, shopping, theater and acclaimed arts and entertainment venues in Ridgefield, Katonah and Danbury. Set on .47 acres of level property with lake views, TEA membership for private beach access and recreation, and a legal accessory apartment, this is a home that gives you plenty of ways to enjoy every day. A covered front porch welcomes you inside, where a tiled entry connects the kitchen, dining room and living room. Spacious rooms set the stage for easy entertaining, while hardwood floors, built-in bookshelves and a fireplace make the living room an inviting spot to settle in. The separate dining room is ready for casual dinners, holiday gatherings and evenings that call for a second bottle. Upstairs, the primary suite delivers room to truly spread out, with three walk-in closets and a generous alcove with built-in bookshelves—perfect for a reading lounge, home office or exercise space. A renovated marble-tiled primary bath features a spacious walk-in shower. Three additional bedrooms and a full hall bath complete the second floor. With its own entrance around back, the legal accessory apartment adds valuable flexibility for housing relatives, guests, a caregiver or potential rental use*. Outside, a level, partially-fenced backyard and stone patio offer space to play, entertain or simply enjoy a quiet evening at home. An attached two-car garage, storage and an on-demand generator with an automatic transfer switch round out the practical perks. Spend the afternoon at the private beach, head into town for dinner or a show, and enjoy HART shuttle service to the train from the area. More room, more options, and a lake lifestyle that keeps you close to everything you love.

46 Truesdale Lake Drive, South Salem
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 1044557 MLS
Experience the perfect union of sophistication and comfort in this meticulously designed home, crafted to enhance effortless living at every turn. From the moment you step inside, you’re greeted by an expansive open floor plan, soaring double-height ceilings, and a tranquil ambiance that exudes natural serenity. Every element has been thoughtfully curated to create a refined yet inviting atmosphere. Nestled on over 5 pristine acres, this property has been impeccably maintained by its original owners. Wide-plank wood floors lend warmth and timeless character, while ample storage solutions ensure a clutter-free, organized living space. The first-floor primary suite is a haven of relaxation, featuring multiple walk-in closets and a spa-like ensuite bath—a private retreat designed to rejuvenate. An additional bedroom and a dedicated office on the main level offer versatile space for guests or work-from-home needs. On the second floor, two generously sized bedrooms and a full bath. The full-footprint basement offers unlimited potential (currently finished and unfinished storage) Another standout feature of this home is the three-car garage, with one bay conveniently located off the kitchen. This space presents exciting opportunities for conversion into anything you want. This property is more than just a residence—it’s an invitation to create the lifestyle you’ve always imagined.

60 Old Aspetong Road, Katonah
$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
$629,000
2 Beds ⋅ 2 Baths ⋅ 1032550 MLS
Gorgeous, completely updated, two bedroom with office and open loft/den townhome in the Katonah Lewisboro School District. The open living space is flooded with light, calming colors, soaring ceilings and a wood burning fireplace. The recently renovated eat in kitchen featuring stainless steel appliances, an enormous center island and deck access is the perfect place to entertain. A primary bedroom with en suite bath, second bedroom, full hall bath and laundry complete the main level. The new staircase leads to the second level which offers an open loft / den and a skylit office with door and closets. Hot water heater, HVAC, windows, flooring, bathroom vanities, and kitchen appliances have all been replaced in the last few years. The Oakridge community has two recently refurbished outdoor pools, new tennis and basketball courts, and play area. This unit also includes a garage and two assigned parking spaces! Walking distance to shopping & dining in Oakridge Commons and just a few miles to New Canaan, Ridgefield and Katonah.

230 Lakeside Drive, 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
$2,595,000
4 Beds ⋅ 4 Baths ⋅ 1020428 MLS
INDOOR POOL! Primary on the main level. Set behind gates on more than 13 acres, with an indoor pool, this subdividable, thoughtfully renovated country property offers a rare combination of privacy, space, and convenience just minutes from the heart of Katonah. With over 4,000 square feet of updated living space, the home features a welcoming layout designed for comfortable everyday living and entertaining. Seasonal glimpses of the reservoir complement the property's natural setting. The home includes four bedrooms - primary on the main level; four renovated baths; an updated kitchen; expansive gathering spaces; and a heated indoor pool that provides year-round enjoyment -- an amenity rarely found in the area. Large windows bring in abundant natural light and frame views of the surrounding landscape. Recent improvements, including a new roof, energy-efficient windows, all-new plumbing, durable Hardie(R)Plank siding, and extensive interior renovations, provide the benefits of modern updates along with peace of mind. Whether as a full-time residence or a weekend retreat, this distinctive property offers generous acreage with easy access to Katonah Village, Metro-North, schools, and major commuting routes. A unique opportunity to enjoy updated country living in one of northern Westchester's most desirable locations.

380 Cross River Road, Katonah
$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
$1,750,000
4 Beds ⋅ 7 Baths ⋅ 1014445 MLS
Katonah, swim at your private oasis, this multi-functional home with in-law capacity, entertainment amenities, and office workspace is nestled on almost 3 acres of lush parklike property. Enjoy the ease of being close to town, elementary school, and Metro-North; this exceptional 3,738 sqft residence offers the perfect blend of tranquility and commuter convenience. Designed with flexible home features including an open floor plan with soaring vaulted ceilings, skylights, full office suite, and beautifully refinished hardwood floors. Offering 4 bedrooms that live like five, along with 4 full and 3 half baths, the layout includes the option of a first-floor primary suite or an equally inviting second-floor suite. The finished lower level with walkout access to patio and gated pool, adds 2,186 sqft, and includes an entertainment area with fireplace, an abundance of storage, and changing rooms. Previously used as a doctor's office with a separate entrance and a renovated waiting area. The newly created chef's kitchen features a Sub-Zero refrigerator, all-new Bosch appliances, including an induction cooktop, quartz counters, and premium finishes. Many upgrades include new HVAC system, all new pool equipment, and freshly painted interior and exterior. Surrounded by mature landscaping, this gated and fully fenced property feels like a private retreat. A rare offering that is move-in ready yet brimming with potential. Some images have been virtually enhanced and/or virtually staged to help showcase the property's possibilities and potential use of space.

60 Cherry Street, Katonah
$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
$629,000
4 Beds ⋅ 2 Baths ⋅ 1016167 MLS
This lake community home has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. Located on a quiet cul-de-sac, this expanded cape cod-style home has good bones and great potential. Upon entering, the front parlor includes a hearth. Beyond, the kitchen opens to a dining room and an expanded family room with a working stone fireplace, home office/den, and a large outdoor deck, forming the hub of this four-bedroom home. There are two bedrooms upstairs and two down, with a full bathroom on each floor. Extra storage is available in an attic easily accessible from the second floor as well as in a large unfinished basement. The level backyard includes a fenced area, old stone walls, mature trees, a concrete pad/patio with a basketball hoop, and plenty of room for a garden.

9 Stewart Road, South Salem
$1,499,000
3 Beds ⋅ 4 Baths ⋅ 1008473 MLS
Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled interiors, rich wood floors, a fabulous fireplace, and an excellent floor plan for everyday living and entertaining. At the heart of the home is a classic Poggenpohl kitchen, as functional and elegant today as when it was first installed, opening seamlessly to inviting gathering spaces filled with natural light. Offering three bedrooms and three-and-a-half baths, the home lives comfortably with generous entertaining areas, excellent indoor flow, and peaceful views of the spacious deck and surrounding property. The expansive grounds provide exceptional privacy and ample room for a pool, creating the opportunity to further enhance this special setting. A rare offering in a coveted South Salem location, 78 Old Church Lane is ready to be enjoyed from day one.

78 Old Church Lane, Pound Ridge
$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
$835,000
2 Beds ⋅ 2 Baths ⋅ 992940 MLS
A rare opportunity in the charming Truesdale Lake community of South Salem. This quaint cottage is in need of renovation and is being sold as-is, offering outstanding potential for restoration, investment, or new construction. Truesdale Lake is an 83-acre private lake community known for its peaceful setting, natural beauty, and long-established neighborhood character. Located in the Town of Lewisboro near the Connecticut border, the property offers access to the quiet appeal of Northern Westchester while remaining convenient to Ridgefield, Pound Ridge, Katonah, New Canaan, and surrounding towns. Ideal for builders, contractors, investors, or end users with vision. Buyer to verify all property details, lake rights, association membership, condition, permits, and building potential. Spend year round at one of Westchester's most coveted Lake communities. Buyer to do due diligence.

8 Hoyt Street, South Salem
$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

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.