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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

$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

$2,150,000
4 Beds 4 Baths 1036619 MLS
Set behind private gates on bucolic, quiet property, this fully renovated 4-bedroom mid-century modern is a rare turn-key retreat. The custom kitchen anchors the home with a Wolf 6-burner gas range with griddle, 42” Sub-Zero refrigerator, and a quartzite double-waterfall island, all set atop new 7” wide-plank white oak floors with radiant heat throughout. New skylights draw natural light through freshly renovated interiors, backed by all-new HVAC, plumbing, electrical, roof, and a full-house generator. Outside, new landscaping and hand-laid stone walls frame a resort-worthy 62’ x 28’ pool with cabana. A detached barn/guest studio offers a recreation room, full bath, sleeping loft, its own new HVAC system, and a 2-car garage — ideal for guests, staff, or creative studio space.

39 Lower Shad 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

$15,000,000
5 Beds 6 Baths 1007263 MLS
EASTLAKE. Nearly 39 serene acres offering the ultimate in privacy. Long, gated drive over rushing stream and through manicured grounds. Remarkable estate compound owned for years by renowned fashion designer as a family residence. Impressive architect-designed Stone and Country House positioned to overlook a private eight-acre lake. Striking and sophisticated Contemporary with elements of a Mid-Century Modern. Impressive rooms with natural finishes of fine woods and hand-cut stone. 5500 square feet of airy, loft-like living space positioned to capture views of the water. Beautifully scaled main rooms with vaulted ceilings, finished in warm woods, stone and hardwood floors and walls of glass. Striking Living Room with stone fireplace and vaulted ceiling lit by a modern cupola. Doors to wrap-around porch for fantastic indoor-outdoor living. Open-concept Dining Area also with water view, perfectly scaled for entertaining. Sleek Kitchen designed for the consummate chef. Private Office with conference area and wet bar. Lower Level Family Room for more casual everyday living. Spacious first floor Primary Suite with ample closets and private Bath. Four additional Bedrooms, most with en-suite Baths. Breathtaking grounds amid dramatic rock outcroppings with stone walls and terraces, an incredible array of flowering plantings, rare and specimen trees and rolling lawns down to the water. Fenced garden for flowers and seasonal produce. Lakefront dock, heated Swimming Pool with Pool House and privately sited Tennis Court make for an incredible sporting lifestyle. Separate building complex with a Three-Bedroom, fully equipped Guest House, Garages for six-plus cars and equipment storage. The perfect, peaceful refuge.

164 Eastwoods Road, Pound Ridge

$3,500,000
5 Beds 6 Baths 823299 MLS
Behind private gates, nearly six acres of bucolic countryside unfold around a spring-fed lake — a setting that feels worlds away, yet sits just one hour from Manhattan. Gut-renovated to the studs and reimagined from the ground up, this Pound Ridge estate blends Mid-Century Modern design with original stone construction and hand-hewn beams — a rare marriage of architectural integrity and contemporary refinement. The result is a home that feels both timeless and entirely of the moment. The main residence offers four bedrooms and has sweeping water views that define the property. A detached guest studio with two-car garage provides flexible accommodation for visitors or staff, while the heated gunite pool and pool house — complete with full bath, wet bar, and huge fireplace — create an effortless setting for both quiet evenings and elevated entertaining. An additional detached two car garage rounds out the offering. Outside, the grounds have been as thoughtfully curated as the interiors: new landscaping, artisan stonework, full irrigation system, patios, and mature tree work frame the lake and connect seamlessly to the Pound Ridge Land Conservancy — a permanent buffer that ensures the privacy and natural beauty of this property endure. Canoe and Kayak directly from the property! Truly turnkey. Completely one-of-a-kind.

39 Old Snake Hill 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.