Ulster & Dutchess County, New York

The town line decides your deal more often than the house does.

I'm Ryan Rooney, a licensed real estate salesperson with Stevens Real Estate at eXp Realty. I grew up in New Paltz. I work with people buying weekend and second homes up here, investors underwriting short-term rentals, and first-time buyers trying to get into a market that keeps moving.

Read the STR permit guide Get in touch

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What I actually do differently

I read the town law before you fall in love with the house

Two houses four miles apart in Ulster County can live under completely different rules. One can be permitted as a short-term rental by a non-resident owner. The other cannot, and never will be. That difference never shows up in the MLS listing, and most buyers find out about it after they are under contract.

I maintain a town-by-town short-term rental permit guide covering 38 municipalities across Ulster, Greene, Sullivan, Delaware, Dutchess, Columbia and Orange counties. Seven of those I have read directly from the local law text, and one more from a city's own published fact sheet. Every other entry is flagged as reported and needing confirmation, because published summaries of these laws contradict each other constantly, and I would rather tell you what I actually know than sound more certain than I am.

I watch the inventory that never reaches the portals

A meaningful share of the houses that suit weekend buyers and small investors trade before they hit Zillow. I track coming-soon and pre-market inventory across Ulster and Dutchess daily. If you tell me the towns you are considering and a rough budget, I will tell you what is coming.

I will give you the unflattering version

If the septic will not certify the fourth bedroom, if the permit does not convey when the property sells, if the town median you read online was built on four transactions and means nothing, you will hear it from me before you write the offer rather than after.

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Where I work

Primarily Ulster and Dutchess County, New York. That includes New Paltz, Kingston, Saugerties, Woodstock, Rosendale, Tillson, Stone Ridge, High Falls, Accord, Marbletown, Gardiner, Highland, Esopus, Rhinebeck, Red Hook and Poughkeepsie, among others.