Quick Facts

Median Household Income: $67,029 
Median Value of Owner-Occupied Housing Unit: $311,700 
Population: 5,869


In Woodstock, there is a feeling of calm that has been cultivated over decades, and it has matured more in recent years. Woodstock’s walkable downtown area has mostly shed its reputation of being its namesake festival’s overgrown gift shop — formerly laced with smoke shops and Grateful Dead themes — while retaining its importance as a center for free-thinking, tolerance and creativity. Highly sought-after artist residencies at the Center for Photography at Woodstock and the Byrdcliffe Guild bring new generations of artists each year, while specialty shops, galleries, and venues continue to feed their sensibilities — a win for everyone. The informal refinement they bring can be tasted in the food at places like Shindig or Tinker Taco Lab, and seen in the world-class art at places like the aforementioned Center for Photography. For such a small town it offers a robust musical spectrum as well. The Bearsville Theatre attracts top-notch local talent like Sister Sparrow and the Dirty Birds as well as living legends like Judy Collins. For classical music, The Maverick hosts the oldest continuously running summer chamber music series in America in a 1916 concert hall in the woods; imagine the sound of crickets providing the intermission between each piece during a summer evening concert.

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The schools are excellent, too: students who live in Woodstock attend Onteora High School, which is ranked 163 on US News & World Report’s 2016 list, earning a silver medal in the national ranking.

The vibe in town is so ideal you would almost feel guilty living this well full time, or maybe not. Joan Lonergan of Coldwell Banker Village Green Realty finds that, “it is home to many dual-home owners with disposable income, whose primary residence is New York City. Many originally move as weekenders and make it full-time when they retire.” If you can afford it, it offers a safe and serene lifestyle that is hard to match. Bonus: if you are retired, you can be sure your children will visit often. 

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