5 houses for sale in Woodstock, NY, a famously artsy town in the Catskills

By Austin Havens-Bowen  |
June 17, 2022 - 12:30PM

This one bedroom, one bath is listed for $499,000.

Keller Williams Realty/Zillow

Woodstock, New York, has long been one of my favorite Hudson Valley getaways because it’s a small town with lots to do outdoors and a main street lined with independent stores and eateries. You also occasionally come across a drum circle in the middle of town and there’s a flea market in summer. It’s not where the Woodstock Music and Art Fair happened (that was in Bethel), but there are plenty of places where you can buy memorabilia honoring the famous festival. 

Tinker Street is the town’s main artery, where you’ll find cafes like Bread Alone (try a pastry or their chicken club), restaurants like Oriole 9 (good for breakfast), Tinker Taco Lab, and Silvia. For shopping, there’s a bookstore called The Golden Notebook, Tinker Toys for kitschy gifts and toys, and boutiques like Woodstock Trading Post.  

The area has also long been a popular place for New Yorkers to buy a summer house, and celebrities like the late Jimi Hendrix and Uma Thurman have lived here. Woodstock also saw a surge in demand during the pandemic when some city dwellers escaped the city. These days, the median sales price is $975,000, according to and there are about 18 houses on the market now.

To get here from New York City is a two-and-a-half hour drive, or you can catch a Adirondack Trailways bus, which leaves you in the center of town.

So if you’re looking to buy a house in the Hudson Valley, check out these five places for sale in Woodstock including a two bedroom on land with a fish pond for $625,000.

276 Chestnut Hill Rd.

This one bedroom, one bath is listed for $499,000. It has a stone fireplace, exposed wood beams, hardwood floors, track lighting, built-ins, a sunroom, detached garage, private driveway, and landscaped yard.  

196 Tinker St.

This two bedroom, two bath is listed for $625,000. The house has wood-paneled walls, hardwood floors, ceiling fans, stainless steel appliances, moldings, recessed lighting, a fireplace, screened-in porch, deck, and a fish pond. 

4 Briarwood Ln.

This three bedroom, three bath is listed for $649,000. The Cape Cod has a wood-burning fireplace, moldings, hardwood floors, oversized windows, millwork, track lighting, a walk-in closet, deck, circular driveway, and large backyard. 

425 Cold Brook Rd.

This three bedroom, three bath is listed for $1,399,000. It has vaulted ceilings, woodwork, a stone fireplace, recessed lighting, stainless steel appliances, moldings, ceiling fans, central air, a basement, decks, and large yard.

324 Byrdcliffe Rd.

This five bedroom, three and a half bath is listed for $1,995,000. It has exposed beams, a fireplace, wide-plank hardwood floors, high ceilings, stainless steel appliances, built-ins, recessed lighting, a two-car garage, and patio. 



Austin Havens-Bowen

Staff Writer

Staff writer Austin Havens-Bowen covers the rental market and answers renters' questions in a column called Realty Bites. He previously reported on local news for the Queens Ledger and The Hunts Point Express in the Bronx. He graduated from Hunter College with a BA in media studies. He rents a one-bedroom apartment in Astoria with his boyfriend and their two cats.

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