Refine Search
Map
Sort by
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 1048139 MLS
OVER 14 PEACEFUL ACRES. Located off a quiet country lane, the perfect private refuge. Exquisite setting with level lawns, Ornamental Grasses and remarkable plantings. Incredible Weeping Cherry, Cut-leaf Maple, Dogwoods, Mountain Laurel, Lilac and Andromeda. Heated, gunite Swimming Pool surrounded by colorful perennials. Classic Country Colonial with warm and inviting living space. Beautifully scaled Living Room with fireplace. Library with extensive built-ins – the perfect spot for reading or working remotely. Comfortable Great Room with fireplace and wet bar. Skylit Sunroom, with window seat, brick floor and doors to the deck for easy indoor-outdoor entertaining. Well-designed Kitchen with center island, pantry and breakfast area. Spacious Primary Suite with fireplace and Bath. Guest Suite with Bedroom and Bath. Two additional Bedrooms. Multi-purpose Bonus Room with rear staircase. Garages for four cars. Convenient location moments to Scotts Corners, the town park, local schools and the library. Easy drive to New Canaan, Stamford and Bedford Village as well as I-684, the Merritt Parkway and Metro North trains. First time listed in over 40 years!

29 Bender Way, Pound Ridge
$3,950,000
5 Beds ⋅ 6 Baths ⋅ 1035090 MLS
Designed by Vuko Tashkovich, one of Westchester's defining modernist architects, this home is privately sited on over 3 acres, offering 7,500+ square feet across three finished levels. Artfully refined while retaining the character of its original design, the home is defined by long horizontal lines, cylindrical forms, clerestory windows and walls of glass that connect the interiors to the surrounding landscape. A gallery-like entry introduces expansive, light-filled rooms with built-ins, tile work and exquisitely restored herringbone floors. The spacious living room is anchored by a stone fireplace, custom bookcase wall, and wet bar, with an adjoining sitting area that opens onto the broad outdoor terrace. The dining room with floor-to-ceiling windows and kitchen with attached breakfast room overlook the lush grounds, specimen trees and newly poured gunite pool with spa. Four bedrooms on the upper level include a spacious primary suite with fireplace, bath and private terrace. Additionally, the ease of single-level living is available with a desirable first-floor primary suite option. The finished lower level adds a newly completed gym, full bath and flexible recreation or office space. This private modernist retreat combines architectural character with modern livability. 50 miles to NYC.

10 Dogwood Hills 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

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.