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.
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 147 municipalities across Ulster, Greene, Sullivan, Delaware, Dutchess, Columbia and Orange counties. 136 of them I have read directly from the local law text or the town's own adopted local law, and a few more, the City of Kingston among them, from the municipality's own fact sheet, application or permit page. 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 will tell you what your number actually buys
Most people start with a portal search and a budget they only half believe in. Tell me what you can spend and the towns you are weighing up, and I will tell you what that actually reaches right now, what you would be trading off, and which of those towns' rules would bite you. Then I set up a proper MLS search, so you hear about a house when it lists rather than when a portal gets round to indexing it.
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.
That applies to my own work too. When I re-read those local laws in September I found that four entries in my own guide were wrong, including one where I had repeated a residency requirement that the town's code does not contain. The corrections are written into the page, named as corrections, rather than quietly swapped out.
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.
Buying a weekend place, or underwriting a short-term rental? Start with the permit guide. It will tell you which towns are worth touring before you spend a Saturday driving.
Send me your numbers
Tell me what you can spend and the towns you're weighing up, and I'll tell you what that actually reaches right now, what you'd be trading off, and which of those towns' rules would bite you. No pitch. If you're a year out, that's the best time to ask.
Search every listing in the Hudson Valley
Full MLS search across Ulster, Dutchess and Orange County, with saved searches and alerts when something new matches what you're looking for. It runs on my Stevens Real Estate site and opens in a new tab.
Worth knowing: the portals lag the MLS, sometimes by days. If you are serious about a town, a saved MLS search beats refreshing Zillow. Tell me what you are looking for and I will set one up.