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Results (216)
Michael Uvaydov In search of a STR regulation friendly market
14 February 2026 | 14 replies
Catskills for sure!  
Michael Chang Tax Benefits & Land-To-Building Ratio In Short-Term Rentals
11 February 2026 | 5 replies
We bought our Catskills property for $995K with land valued at only $54K.
Fizza Ali Struggling to Pick My First STR Market
21 January 2026 | 24 replies
I picked my first one in the Catskills because its close to where I live in NYC.
Peter Castrianni Short term rental Catskills , Shenandoah
2 January 2026 | 3 replies
Catskills area NY or Shenandoah Valley VA such as Luray Stanley. 
Peter Castrianni Building in the Catsills
28 December 2025 | 1 reply
Has anyone build from the ground up in Catskills please mssage me. 
Enisé B Derinbogaz Building small STR cabins on raw land — what would you assess first?
29 December 2025 | 4 replies
I’m exploring the idea of building a small cluster of short-term rental cabins on a specific parcel of undeveloped land (Northeast / Catskills-type context).I’m comfortable with the STR side, but I’m intentionally slowing down on the land and build assumptions before moving forward.
Eric Stoner Upstate NY and Kingston team advice
3 December 2025 | 13 replies
For your team:Attorney: I’d prioritize someone who does RE closings in Kingston/Catskill every week and is comfortable with inspection/contingency issues on older properties.CPA: Local is a plus but not mandatory, what matters most is that they’re real-estate focused and understand NY rules, depreciation, entity options, and how this first property fits into a longer-term portfolio.Bank: Call a couple of local/community banks and ask specifically about how many investment property loans they do and whether they keep loans in-house.When you’re interviewing anyone, I’d ask, “How many small investors like me do you work with, and what do you wish they asked you before buying their first deal?”
Gokce Sahin Investing in an STR in Upstate NY or Poconos
18 October 2025 | 5 replies
I’ve owned/managed STRs in nearby markets and both the Catskills and Hudson Valley can work — they just perform differently.
Dmitri L. Strategies for land banking
10 October 2025 | 1 reply
So, I was looking on Zillow at this ~700 acre lot in the Catskills listed for $10m.
Peter Castrianni Advise on where to build our next short term rental.
23 September 2025 | 23 replies
Finger Lakes NY, Catskills NY, or Poconos PA.