Woodstock, NY Homes for Sale under $2,000,000

A Woodstock compound with two distinct residences on eight acres, currently set up as STR. Included as part of this unique offering, 7 Downer Road brings an entirely different yet equally compelling dimension to the property. Set on approximately two private acres with beautiful mountain views, this authentic mid-century ranch captures the simplicity and warmth.The one-bedroom home

Baris Demirel Serhant LLC

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

Kathryn Johnson William Pitt Sothebys Int Rlty

Tucked at the end of a private road just minutes from Woodstock, this exceptional five-bedroom, five-bath residence offers an uncommon combination of privacy, generous scale, and scenic charm. Set on approximately three acres and bordered by a year-round stream, the 3,722 square foot home feels wonderfully secluded while remaining close to the restaurants, shops, galleries, and creative energy of

Leslie Foti Coldwell Banker Village Green

Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

Joan Capria Four Seasons Sotheby's Int'l R

Rare investment opportunity in Woodstock: a collection of five unique cottages on six wooded acres located just minutes from the Village's vibrant shops, dining, and nightlife. Each home boasts a distinct personality and peaceful forest views, and all five have been successfully rented with a combination of short- and long-term tenants. Possibilities include renting all five cottages or living in

Lillian Kology Halter Associates Realty