Pound Ridge, NY Homes for Sale with Pool

This one-of-a-kind 5 bedroom, 5 full bathroom rustic Adirondack-style residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned

Elizabeth Ronel Coldwell Banker Realty

New construction in the heart of Pound Ridge, this modern European-inspired residence is gracefully set on a picturesque property overlooking Pinebrook Road. Thoughtfully designed to blend clean architectural lines with warm, natural materials, the home is complemented by a charming, fully renovated two-bedroom, 861-square-foot cottage—ideal for guests, extended stays, or flexible living.

Mark Boyland Keller Williams Realty Partner

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

Samuel Berek Serhant LLC

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

Angela Kessel Houlihan Lawrence Inc.

The pinnacle of Modern Colonial elegance in Pound Ridge: timelessclassicism elevated to a grand scale, featuring spacious rooms, prestigeamenities and luxury finishes crafted for contemporary comfort. Set on 3.7acres on exclusive Great Hill Farms Road, it’s minutes from both BedfordVillage and Stamford and an hour to Manhattan. Sunlight streams through the double-height entry,

Katherine Biddle Houlihan Lawrence Inc.

Some properties simply cannot be recreated.They are collected over centuries. Layer by layer. Story by story. Stone by stone.Set behind towering trees and abutting hundreds of protected acres of the Mianus River Gorge Preserve, this exceptional Bedford estate offers a rare opportunity to own a thoughtfully restored historic property surrounded by natural beauty and privacy.Dating back

Kile Boga-Ibric Houlihan Lawrence Inc.

Linden Farm. Reminiscent of the great old estates of Europe. Spectacular distant views from over 60 breathtaking acres with natural ponds, lush lawns, gardens and a multitude of magnificent age-old and specimen trees. Long, gated drive to the manor house built in 1929 in need of complete restoration and renovation. Being sold "as is." Structure has been taken down to the studs and is ready for a

Mindy Weil Ginnel Real Estate

Nestled on two private acres, The Owl's Nest is a striking 3-bedroom, 2-bath mid-century modern chalet that blends architectural character, privacy, and modern convenience. Surrounded by nature, the home feels like a secluded retreat while remaining easily accessible to nearby towns and commuting routes. The heart of the home is a dramatic living room with soaring 18-foot ceilings and

Nadejda Kovaleva Supreme Home Sales, Inc.

THE PERFECT COUNTRY COMPOUND. Rare offering in one of Bedford's most sought-after neighborhoods. This truly move-in ready stone and shingle expanded farmhouse blends timeless country charm with the clean lines and sleek finishes of new construction — on nearly 3 beautifully landscaped acres along a private bucolic road with direct walking access to Ward Pound Ridge Reservation. Flexible

Mindy Weil Ginnel Real Estate

A Modern Colonial Retreat, 83 Upper Shad Road, is situated on 2.25 private, level acres in the heart of Pound Ridge. Mature trees and professionally designed landscaping create a serene, park-like environment, with an in-ground pool and manicured green expanses that surround the home. (Did I forget to mention the babbling brook at the corner of the property?) The home features a primary bedroom

Richard Esman Douglas Elliman Real Estate

Experience true serenity in this stunning modern retreat in the woods of Pound Ridge. A dramatic entrance welcomes you into the home with vaulted cedar ceilings, Brazilian cherry floors, mahogany steps, and black cherry millwork. The free-flowing open floor plan connects skylit dining room, beautiful SieMatic custom kitchen, and two sunny living rooms, each with a wood burning fireplace. Main

Christine Ricci Keller Williams NY Realty

Set high on a hill overlooking the Pound Ridge Reservation, 71 Old Stone Hill Road is a dramatic Modern positioned to capture natural light and distant views. Constructed in 1987 housing approximately 4420 square feet of living space, the interior is stunning. The floorplan is open and fluid allowing for seamless entertaining. Clean, crisp lines, walls of windows, high ceilings, lots of glass,

Lisa Fitz Ginnel Real Estate

This beautifully appointed, grand and stylish Colonial seamlessly blends grand-scale entertaining with intimate everyday living. Highly sought after location at the end of a quiet cul-de-sac, the home offers exceptional privacy while remaining just minutes from Bedford Village, Scotts Corners, and acclaimed Jean-Georges’ Inn at Pound Ridge. New Roof, New kitchen and appliances including

Sarah Stone The Higgins Group Inc

An extraordinary 268-acre legacy estate spanning the New York-Connecticut border, Hillandale offers unrivaled privacy and timeless grandeur. Once owned by the Sulzberger family of the New York Times, the 15,000+ sq ft, eight-bedroom European-inspired manor has been meticulously restored and features magnificent formal entertaining rooms, 11 fireplaces, two elevators, a paneled library, sun-filled

Leslie McElwreath Sotheby's International Realty