A well-known, quintessential Catskills town with a vibrant and engaged community. It continues to evolve and stay relevant.

Welcome to Woodstock

Unless you’ve been living under a rock, you’ve probably heard of Woodstock. The town, one of the quintessential Catskills spots, is filled with eclectic shops, some crunch, some upscale, along with too many eateries to mention.  One could easily spend a day wandering around without a hint of boredom.  On weekends, the town is abuzz with locals and weekenders alike.   And just outside town is the Slide Mountain Wilderness with some of the most popular hikes in the Catskills.

Woodstock Real Estate Insights

Woodstock, NY homes for sale can encompass the full range of the Catskills real estate options from farmhouses, stone houses, new modern builds, small cabins, tiny houses, and more.  If you want the option of walking to town, you may pay a bit of a premium and you’ll likely be on a smaller plot of land.  As you get up into the hills and down in the valleys surrounding the town, you’ll start to have larger plots on offer.  With 2,300+ local residents, it maintains a small-town vibe but with weekenders/tourists it always feels alive. 

Note, in 2019 the town of Woodstock passed a law regulating short-term rentals. If you plan buy a second home in Woodstock and rent it out on AirBNB/VRBO, you may want to look into purchasing in alternative areas or, at the very least, inquire about whether any houses in which you may be interested are registered with the town. 

The People and the Lifestyle

The town is rich with culture and represents a convergence of creatives, tradespeople, entrepreneurs, city transplants, long-time locals and weekenders. It’s long been a mecca for artists of all stripes. The Woodstock Byrdcliffe Guild, established in 1903, is one of the nation’s oldest arts and crafts colonies and occasionally homes become available in this unique area.  Music lovers may want to check out Levon Helms Studio, (a Woodstock and Catskills institution) which is a former barn converted into a performance venue where you can catch local and nationally-known acts. The Center for Photography is a non-profit exhibition space where you check out free galleries.  Many Sundays at around 4pm, musicians gather in the main circle, bongos and drums in hand, for a spontaneous drum circle. And, of course, the widely acclaimed Woodstock Film Festival, a haven for independent and groundbreaking film, takes place in early fall.

Insider Tips

Restaurants (by no means an exhaustive list)

  • The Mud Club.  With a college town cafe feel, it's a great spot to grab a coffee and a bite before exploring the town or surrounding area. 
  • Shindig.  It’s a hip little spot to grab slightly elevated, deliciously prepared, local and seasonal fare prepared without the fuss that typically accompanies such cuisine. 
  • Tinker Taco Lab.  It’s a popular spot, so much so that sometimes they sell out certain tacos by dinnertime. And they serve margaritas. The space is tucked behind a sunglass shop but it’s definitely worth seeking out if you’re in the mood for a delicious Mexican meal. 
  • Bread Alone. You’ve probably come across Bread Alone’s products in your hip grocery stores but I’d guess that you didn’t know the brand was born in the Catskills. It’s also a Woodstock institution. While you might think bread is the draw (which is sort of true) there are all sorts of food options on their menu.  It’s also a great spot to plop down with your laptop to get some work done. 
  • Silvia.  Launched by fellow Brooklynites, Silvia's takes the farm-to-table mantra seriously. With a heavy reliance on locally-sourced ingredients, the American cuisine frequently takes cues from various global cuisines, including Korea and other Asian countries. It's a mainstay for both locals and weekenders looking for a sophisticated dining experience.
  • Cucina.  Located in a big and beautifully restored and converted farmhouse, Cucina is a modern Italian restaurant that is a staple in the Woodstock culinary scene. With its contemporary expertly prepared Italian cuisine made with seasonal locally-sourced ingredients and its country-chic and cozy setting, it's a spot definitely worth checking out.


  • A&P Bar.  Located in a strip mall next to a bank and a health food store, the location clearly isn’t the draw but the good news is that there are real mixologists here that take their craft seriously.  Great place for some drinks and snacks. 


  • Overlook Mountain:   The trailhead is about ten minutes from town the full round-trip loop takes about 2.5-3 hours.  At the top, there are various overlooks, including a fire tower with expansive views. It’s not an easy hike but it’s worth the effort (in our humble opinion).

Should you have any questions about Woodstock, NY real estate, please don’t hesitate to reach out.  We regularly meet clients for coffee in either NYC or the Woodstock area to share our knowledge of the area, the local real estate market, and to assist with searching for Catskills real estate.

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