Woodstock, NY Homes for Sale with Pool

Welcome to Bearsville Record House, a landmark property with a legacy in American music. Built in 1873 and once home to Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the grounds, all along 500 feet of

Anthony D'Argenzio Houlihan Lawrence

Tucked just beyond the heart of Woodstock, down a private road off a quiet dead-end street, this completely renovated home feels like a secret you're lucky to have discovered. Just 2.5 miles from town and moments from the Bearsville Theatre, the setting is both deeply private and wonderfully connected.While the exterior presents a discreet, understated presence, the interior unfolds into a

Alexis Li Corcoran Country Living

Experience the legacy of Woodstock through this extraordinary historic offering. Once home to the iconic Woodstock Lodge and The Pinecrest, this storied 6.5-acre property offers a unique opportunity to reimagine a legacy estate in one of the Hudson Valley's most sought-after destinations. Set on scenic, gently rolling land with a blend of open clearings, wooded trails, and a seasonal stream, the

Kathryn Johnson William Pitt Sotheby's Interna

The essence of Woodstock; the artists, the poets, the musicians and the creatives who have gravitated to the beautiful, iconic Catskill Mountain town, no-one embodies the original spirit of Woodstock more than local artist and environmentalist Calvin Grimm. Every home tells a story. This hand built 1 Bd/ 2 Ba with additional flex room and art studio tucked away on 2 private acres on a dead end

Johanna Trimboli Halter Associates Realty

Tucked into a quiet cul-de-sac, this spacious 4-bedroom, 2.5-bath Colonial features a gorgeous in-ground swimming pool surrounded by mature plantings. With a comfortable, easy flow, a welcoming foyer opens to a bright main level that connects the living room, dining area, and updated kitchen.The kitchen is equipped with granite countertops and stainless-steel appliances, while the bathrooms

Susanna Scott-Mitchell Compass Greater NY, LLC

Welcome to Nature's Edge -- a Woodstock estate, where wilderness meets luxury. Perched at the end of a secluded private road, this modern mountain marvel offers unmatched privacy, serenity, and grandeur. Surrounded by natural woodscapes and native rock outcroppings, this 40 acre property sits adjacent to over 500 acres of forever wild NYC DEP land. The home itself, a Barry Price architectural

Heidi Rothe Grist Mill Real Estate

A modernist retreat set against one of the most striking backdrops in the Catskills. 540 Mt. Tobias Road is an architect-designed home where clean lines and expansive glass dissolve the boundary between indoors and out. A wall of windows frames uninterrupted mountain views, pulling light and landscape into every corner of the home. The effect is immediate. Calm, quiet, and completely immersive.

Alexander James Compass Greater NY, LLC

Selling fully furnished. 9 Munchkin Lane: A Designer Sanctuary in Woodstock Experience turnkey luxury on 5 private, wooded acres. Featured in Instagram’s "Best of Design," this stunning estate is being sold fully furnished—including all high-end decor, electronics, and linens. Just 5 miles from Tinker Street, the home has been meticulously renovated with exposed beams, hardwood floors, and a

Jonathan Minerick HomeCoin.com

Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

A bright and sunny Colonial gem just minutes into the center of Woodstock! This home is set far back and hidden from the road creating a true sense of privacy. Coming down the driveway, you begin to see the 1.47 acre yard wrapping around the house which is partially bordered by a charming stone wall. Once inside, the spacious living room is on your left with built-in bookcases and a fireplace

Richard Stoll Halter Associates Realty