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$725,000
3 Beds 2 Baths 1050409 MLS
INCREDIBLE OPPORTUNITY. One of Pound Ridge’s foremost estate areas. Over two peaceful, level acres with towering trees, verdant lawns and mature plantings. Solidly built Country Ranch brimming with potential. Originally built in 1955, expanded in 1993. An easy renovation or foundation to build anew. Nicely scaled rooms and hardwood floors. Large picture windows to capture natural light and woodland views. Well-proportioned Living Room with stone fireplace, raised hearth and a mahogany-paneled wall. Sun-filled space Dining Room with two built-in side hutches and doors to the deck. Oak Kitchen with Corian counters. Family Room with extensive built-ins and pine paneling. Three Bedrooms include a private Primary Suite. Large deck -- the perfect spot for alfresco entertaining. First time offered!

28 S Bedford Road, Pound Ridge

$3,195,000
4 Beds 5 Baths 1050330 MLS
STUNNNING & SOPHISTICATED. Striking re-imagination of a classic Deck House completely transformed and expanded in 2024. Stunning use of natural materials and sophisticated style. Desirable open floorplan highlighting the elements of the original design. Vaulted ceilings finished in wood, exposed beams and walls of windows create a sun-filled living space. Two-story Entrance Hall. Impressive Living Room with soaring ceiling, pendant lighting and fireplace finished in Moroccan tile. Open Dining Room amply proportioned for entertaining. Sleek Chef’s Kitchen with custom Bilotta cabinetry, Quartz counters, a marble backsplash and high-end appliances. Comfortable Family Room seating area. Choice of Offices for working remotely. Four Bedrooms include private Primary and Guest Suites. Lower level flex space with Media and Recreation areas. Finished Garage currently housing Home Gym. Ipe decking around private Swimming Pool. Gated drive to over five peaceful acres with babbling brook, verdant lawns, towering trees and specimen plantings. A magical setting near the protected lands of the Ward Pound Ridge Reservation. The perfect peaceful refuge!

21 Black Spring Road, Pound Ridge

$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

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