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$2,900,000
5 Beds ⋅ 4 Baths ⋅ 1037090 MLS
Set behind stone pillars at the end of a meandering private drive, this custom-built stone manor draws its inspiration from a 19th-century English manor house. This home features a rare blend of Old World craftsmanship and modern-day comfort on more than four private, lushly landscaped acres, just about an hour from New York City. Built in 1988 and thoughtfully updated since, the residence offers over 6,000 square feet of living space across three levels, with 6 bedrooms and 4 full and 1 half baths spread across 11–12 rooms. Five fireplaces anchor the home's principal rooms. The living room, a soaring 39' x 24' space with 12' coffered pine ceilings and a massive floor-to-ceiling stone fireplace, sets a formal yet inviting tone, while the library's built-in cabinetry and Art Deco lighting bring a warmer, more contemporary counterpoint. The gourmet kitchen is a true tour de force, outfitted with Neff cabinetry, Viking appliances, and its own floor-to-ceiling stone fireplace. A library with French doors opens directly onto a stone terrace, ideal for quiet mornings or evening entertaining. Upstairs, the primary suite is accessed through a generous sitting room/office with its own fireplace and continues into a bedroom with a tray ceiling and another fireplace, as well as a dressing area with a lovely walk-in closet and a spacious primary bath. Three additional bedrooms and a bath complete the sleeping quarters. Outdoors, the grounds are just as considered as the interiors: an oversized heated gunite pool and spa, surrounded by extensive stone terracing, formal and English gardens, and manicured lawns. The detached three-car garage includes a heated guest, staff, or au pair suite with a full bath, offering flexible space for visitors, live-in help, or a private studio/office. Notable amenities include marble and granite finishes throughout, gleaming hardwood floors, and 9' and 12' ceilings. Every detail reflects a home that was built without compromise and maintained the same way. Zoned for the highly regarded Katonah-Lewisboro School District, including Meadow Pond Elementary School, John Jay Middle School, and John Jay High School, this is a rare offering for buyers seeking a full-time residence or a refined weekend retreat within easy reach of Manhattan.

295 Salem Road, Pound Ridge
$1,550,000
3 Beds ⋅ 3 Baths ⋅ 1023810 MLS
A Storied Colonial. A Picturesque Pond. A Rare Piece of Pound Ridge History. Set in the heart of Pound Ridge’s historic hamlet, the Horace Reynolds House is an extraordinary 18th-century Colonial that beautifully marries the romance of the past with the elegance of today. Originally built in 1784 and later thoughtfully renovated by renowned philanthropist Hiram Halle in the 1930s, this exceptional residence is steeped in the history and character of old Pound Ridge. Today, the home has been exquisitely and thoughtfully decorated by a renowned local interior designer, creating an atmosphere that is sophisticated yet inviting, polished yet entirely at home in its historic setting. Inside, original architectural deals take center stage -- wide board floors, high ceilings, hand hewn beams, beautifully aged paneling and multiple fireplaces lend warmth and authenticity throughout. Gracious proportions, beautifully considered space for both everyday living and entertain. Large windows draw you outward to the property's most enchanting feature -- a picturesque pond of more than two acres, complete with private dock. 18 Salem Road is more than an antique home - it is a beautifully preserved slice of Pound Ridge history, reimagined with extraordinary style and surrounded by a timeless landscape.

18 Salem Road, Pound Ridge
$2,900,000
4 Beds ⋅ 4 Baths ⋅ 1042389 MLS
The Epitome of Mid-Century Modern Architecture: Streamlined wood and glass MCM home exudes warmth and ease-of-living layout in its private , preserve-like setting. Minimalist design details and its turn-key condition will attract the mid-century modern enthusiast which includes 21st century digital updates. High-beamed ceilings and open social spaces inclusive of dining & living areas present vistas of lush, well designed grounds. The fenced outdoors has thoughtfully designed landscaping and the swimming pool is outfitted with a sun-shelf, electric cover and spa. There is a 2 car, climate controlled attached garage in addition to a newly built 2 car garage which is also climate controlled. Both have dual EV electric charging units. Offered fully furnished except for artwork.

14 Cradle Rock Road E, Pound Ridge
$3,200,000
4 Beds ⋅ 4 Baths ⋅ 1032314 MLS
A landmark Pound Ridge residence, this circa-1769 Amon Marshall Homestead was expanded over generations and has now been masterfully restored with remarkable sensitivity to its architectural heritage. Set on nearly four acres of lawns, gardens, woodland, stone walls and a picturesque pond, the home preserves its centuries-old character while offering exceptional modern comfort. Original hand-hewn beams, wood walls, historic doors and hearths were carefully restored and complemented by Venetian plaster, Marmorino, limewash, bespoke millwork, custom stonework and vintage European lighting. The chef’s kitchen pairs Cristallo marble with custom cabinetry, an AGA range and Sub-Zero appliances, while gracious living and dining spaces showcase wide-plank and herringbone floors, beautifully restored fireplaces and remarkable architectural detail. The four-bedroom layout includes a serene first-floor bedroom. The upper level offers a primary suite with custom closets and a luxurious marble bath with freestanding tub and restored steam shower. Outside, historic gardens and mature rhododendrons were revived, woodland reclaimed, stone walls repaired and the pond restored. A beautiful cedar-shake barn and possible pool site complete this singular setting. The result feels neither newly renovated nor frozen in the past, but as though it has evolved beautifully over generations, a rare property of authenticity, craftsmanship and enduring character.

156 Old Stone Hill Road, Pound Ridge
$2,299,995
4 Beds ⋅ 6 Baths ⋅ 1019164 MLS
Antique lovers... A near impossible to find rare gem set on a quiet back road of only a handful of homes - step into the charm of the landmarked Sarles-Bode house, a quintessential c.1750 home in Pound Ridge, NY. This is a rare offering where timeless character and everyday livability come together in the main house, guest house, and extensive outdoor entertainment areas. Layered with history, the original 18th-century main residence, later expanded in both the 19th and 20th centuries, retain its original charm throughout a complete and careful top to bottom renovation (2023-2026) This remarkable property showcases beautifully preserved wide plank flooring and hand hewn beams throughout the interior. The exterior is complemented by extensive dry stone walls, exceptional stonework patios, and amazing rock outcroppings. All rooms offer their own charm, highlighted by built ins, bookcases and distinctive wooden doors- each with its own character and paired with original materials that create a true sense of history. The living room features a wood-burning fireplace and built-ins, while the dining room offers a second fireplace. The primary bedroom sits privately at the back of the main residence featuring his and her baths, a huge lounge area and amazing sunset views. The large 2 story guest cottage is private from the main house yet easily accessible to the pool and property featuring 2 full baths, a great room downstairs and oversized guest bedroom upstairs. Set on over 2 beautiful, private professionally landscaped acres, this one of a kind cherished residence seamlessly blends historic character with the modern-day comforts of today. If buyer wishes, property is available furnished (with the exception of a few family heirlooms/antiques) including most furniture, wall art, lighting and televisions. Seller financing available.

35 Old Snake Hill Road, Pound Ridge
$940,000
4 Beds ⋅ 3 Baths ⋅ 1007052 MLS
Private updated retreat within minutes to Scott's Corners, and across the street from Pound Ridge Town Park. Enjoy the wood burning fireplace in the living room, updated kitchen with new appliances, updated baths, and hardwood floors throughout. Easy flow with rooms bathed in natural light and deck off kitchen makes entertaining, or basking in the sun, a breeze. This home sits on 2.81 private acres, with a long driveway and mature trees. Finished basement provides additional space with walk out, and is also accessible through attached two car garage. This home boasts a total of 5 garage spaces (2 attached, 3 detached) with the option of 24' ceilings. Perfect for families with lots of storage needs, car enthusiasts, or those wanting to lease out the extra garage space. Recent updates include: New roof 2016, new septic fields 2021, new windows, new driveway, new bib in garage, newly done retaining wall, and freshly painted! Don't miss this hilltop charmer!

186 High Ridge Road, Pound Ridge
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 993992 MLS
Cozy-chic country Colonial thoughtfully reimagined from top to bottom by an award-winning international designer. Many details reflect quality materials and a highly curated aesthetic. The heart of the home is a bespoke chef's kitchen anchored by striking Viola Fantastico marble, a deVOL English sink, professional-grade ILVE range, Waterworks fixtures, Apparatus lighting, custom Vermont oak cabinetry, and radiant-heated Belgium bluestone floors. French doors lead to a large deck overlooking level lawns and stone walls. Designed for both entertaining and comfortable daily living, the main level offers exceptional flow through the living room with marble fireplace, formal dining room, expansive great room with stone fireplace, and a sun-filled conservatory. Retreat to the primary suite with a lounge, dedicated office, window seat nooks, and a spa-inspired bath with Waterworks fixtures and a Penhaglion soaking tub. Three more bedrooms, one that can be used as a second primary, round out the second level. The finished walkout lower level adds an additional 1,737 square feet of flexible recreation, fitness, or work space. Brand new roof; AC; and gutters. The property abuts more than 70 acres of protected watershed land, offering an exceptional sense of privacy and tranquility. Set on a quiet country lane, yet just moments from the shops, restaurants, hiking trails and amenities in Scotts Corners and New Canaan -- including the New Canaan train. One hour to Manhattan.

240 Eastwoods Road, 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
$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
$2,599,000
5 Beds ⋅ 7 Baths ⋅ 976870 MLS
Step into a slice of Mediterranean paradise at 105 Cross Pond Road, where timeless elegance meets modern luxury. This breathtaking villa, inspired by classic European architecture, boasts over 6,000 square feet of refined living space on 5.+ meticulously landscaped acres. From the iconic red clay roof to the graceful stucco and stately arches, this property exudes sophistication at every turn. Key Features That Will Steal Your Heart: Mediterranean Charm: The distinctive architectural elements create an enchanting, old-world aesthetic. Expansive Interiors: Multiple fireplaces, private terraces, and oversized balconies invite seamless indoor-outdoor living. Private Waterfront Oasis: Your very own lagoon offers tranquil views, waterside relaxation, and kayaking adventures just steps away. Luxurious Finishes Throughout: Marble and natural stone details bring warmth and elegance to every room. Nature’s Playground: Over 5+ acres of pristine grounds, complete with a private island, provide endless opportunities for outdoor entertaining and peaceful solitude. Inside the Villa: From the moment you enter, the grand scale and thoughtful design captivate. Open-concept spaces flow effortlessly, perfect for everything from quiet evenings to hosting grand gatherings. Marble and stone finishes elevate the interiors, while fireplaces add cozy charm. Step outside onto expansive terraces and balconies to savor al fresco dining or watch the sunset over your serene property. The home also offers flexible spaces ideal for a chef’s kitchen, wine room, home gym, or a luxurious primary suite. Unbeatable Location for a Coveted Lifestyle: Nestled on prestigious Cross Pond Road in Pound Ridge, this estate combines privacy with accessibility. It’s part of the highly regarded Bedford Central School District and offers convenient access to I-684, Saw Mill Parkway, and Metro-North stations for an effortless commute to Manhattan. Nature lovers will adore the proximity to Ward Pound Ridge Reservation for hiking, camping, and fishing, while the charming nearby towns of Katonah, Bedford, and Stamford, CT, provide boutique shopping, fine dining, and cultural experiences. For wine enthusiasts, local vineyards and specialty shops await to help you curate the perfect collection. A Once-in-a-Lifetime Opportunity: 105 Cross Pond Road isn’t just a home—it’s an experience. Whether you’re savoring lakeside mornings, hosting elegant, or simply enjoying the serene beauty of your surroundings, this estate offers a lifestyle of unparalleled luxury and tranquility. Don’t miss your chance to make this extraordinary retreat your own.

105 Cross Pond Road, Pound Ridge
$915,000
4 Beds ⋅ 3 Baths ⋅ 961485 MLS
This private, Colonial-style residence sits on 2.5 partially wooded acres in coveted Pound Ridge, offering the ultimate serene Westchester retreat. Blending countryside peace with everyday connectivity, this inviting home features 4 generously sized bedrooms and 3 full bathrooms. Inside, a versatile floor plan unfolds with cathedral ceilings and expansive living spaces designed for both cozy relaxation and entertaining. The sun-drenched, eat-in kitchen shines with skylights, a center prep island with quartz countertop, and an integrated gas cooktop. The gourmet kitchen also has premium stainless steel appliances, including an updated Whirlpool dishwasher (2021), island cooktop (2023), in-wall oven and microwave (2020/2021), and GE refrigerator (2023). Unwind in the intimate, warm den equipped with a classic wood-burning stove, or gather in the formal living room anchored by an elegant fireplace. Panoramic windows throughout the interior showcase woodland views while filling every corner with natural light. Host memorable dinner parties in the formal dining room, or relax on the private outdoor deck. An unfinished bonus room off the living room presents unlimited potential to craft a custom sunroom, screened porch, or home office. Other notable improvements include: New roof (2025) and a detached, two-car garage (2022) providing ample storage. This property delivers an unmatched country lifestyle.

17 Highview 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.