Rock On! 10 Woodstock-Area Homes for the Festival’s 50th Anniversary

For four brief days 50 years ago, a 600-acre dairy farm in Bethel, NY, was transformed into a Zeitgeist-defining gathering known as the Woodstock festival. Those muddy, raucous, brown acid-fueled days have been dissected endlessly over the five decades since.

The town of Woodstock (about 60 miles from Bethel) has been a haven for artists since the early 1900s. By the 1960s, it had become the home of many musicians, including Bob Dylan, making the Hudson Valley a convenient spot for a festival.

Festival organizers originally planned for it to be held in Walkill, NY, but found an alternative venue after having trouble persuading residents of the small, rural town to welcome 400,000 hippies. They soon made a deal to hold the event on the dairy farm in Bethel owned by Max Yasgur, who was willing to give his land over for a few days in the name of peace, love, and music.

Today, we have documentaries, recordings, and photos to remember the festival that defined an era. This year, there was a feeble attempt to organize a 50th anniversary event, but the idea was ultimately scrapped.

So instead of hippie nostalgia, we’re focusing on today. If you’d like to buy a home in an area touched by rock history, we’ve rounded up 10 homes for sale in both Woodstock and Bethel. Just make sure to bring your own granola.

122 Boggs Hill Ext, Woodstock, NY 

Price: $549,000

Cedar and seclusion: This remote, private getaway was recently renovated by Cary Cook, a well-known architect and artist in Woodstock. The result is a cozy, modern home that blends seamlessly with the surrounding woods. Built in 1984, this rustic residence has three bedrooms and sits on nearly 3 pristine acres close to the Catskills and Hudson Valley.

Cedar house in Woodstock, NY

Boggs Hill Extension, Woodstock, NY



14 Juniper Ln, Woodstock, NY

Price: $625,000

Byrdcliffe Cottage: This three-bedroom home is a prime example of a 1920s Woodstock artist’s cottage and was once owned by a well-known local ceramicist. Aspects of the home, including the vaulted ceiling, were built with trees harvested from the wooded, 2.5-acre lot. There’s a separate one-bedroom, one-bath apartment with a small kitchen, deck, and garage built by the Woodstock architect Les Walker. The grounds also feature extensive bluestone patios and a circular driveway.

cottage in Woodstock, NY

Byrdcliffe Cottage, Woodstock, NY


7 Schoonmaker Ln, Woodstock NY 

Price: $649,000

Work/live in Woodstock: This half-acre property is located just outside Woodstock’s town center. Extensive renovations to the two-bedroom home have been completed by the current owners. The main, Cape-style house was built in 1921, and a second building is zoned for a professional office with seven dedicated parking spaces and a separate address, for a sweet work-life setup.

Cape style house in Woodstock

Schoonmaker Lane, Woodstock, NY


2626 Glasco Turnpike, Woodstock, NY

Price: $1,250,000

Brookside Home: This home was built in 1900 as part of the original Byrdcliffe Arts Colony. Today, it’s one of the few homes in the community that is privately owned. A recent modern-industrial renovation gave the four-bedroom home a luxurious new life. There are hand-plastered walls, vaulted ceilings, custom windows and doors, designer lighting, stone floors in the kitchen, and floor-to-ceiling glass doors to bring the outside in. The park-like half-acre lot includes a heated, large bluestone patio, saltwater pool, and screened-in porch.

modern home in Woodstock, NY

Glasco Turnpike., Woodstock, NY


201 Ohayo Mountain Rd, Woodstock, NY 

Price: $595,000

Maverick Original: This home was built by one of the original members of the Maverick Art Colony in 1934 and has been owned by a well-known Woodstock artist ever since. The three-bedroom home is being sold as is and includes wood floors, a fireplace in the living room, and a screened breezeway that leads to a painter’s studio filled with natural light. The more than 4-acre lot also includes a second, larger artist’s studio and garage with a studio and bathroom built above it.

Woodstock home with studio

Ohayo Mountain Road, Woodstock, NY


118 Fairweather Road Trail, Bethel, NY

Price: $549,000

Golden Pond: Built in 1990, this five-bedroom home sits on more than 12 wooded acres that include a private pond. The home is just minutes from the original Woodstock Festival site, which is now commemorated by the Bethel Woods Performing Arts Center. The roomy 2,500-square-foot home also has a finished basement, so there’s plenty of room for family and friends to visit.

home with pond in Bethel, NY

Fairweather Rd. Trail, Bethel, NY


132 Deer Meadow Rd, Bethel, NY

Price: $1,200,000

Black Lake Estate: This sprawling country estate includes more than 18 acres, after three secluded parcels in Black Lake Estates were combined for privacy. The five-bedroom home was built in 2003 and includes a striking atrium entry with a glass wall overlooking the property’s lake. There are slate floors, lake-view balconies, and plenty of spaces for outdoor entertaining.

Country estate in Bethel, NY

Deer Meadow Rd., Bethel, NY


1923 State Highway 17B, Bethel, NY

Price: $119,900

Future festival?: This over 20-acre lot is just around the corner from the site of the original Woodstock Festival and is zoned for both residential and commercial purposes. Today, the land is open fields, covered with wildflowers in spring and summer, and could be the beginning of something special for an enterprising concert promoter looking to recreate music magic. It’s also ideal for building a dream house close to town.

20 acre lot in bethel ny

State Highway 17B, Bethel, NY


20 Sunset, Bethel, NY

Price: $599,000

Chapin Estate: This lovely three-bedroom was built in 2003 and includes a 5-acre lot in the gated Chapin Estate. Inside, the home is open, with high ceilings, and includes a stone fireplace and loft with an extra sleeping area for guests.

adirondak home in Bethel, NY

20 Sunset, Bethel, NY

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Source: Housing Trends Feed