Hi BP friends! Looking for advice on investing in Windham/Hunter

2 Replies

Hi there!

I recently purchased and am living in my second multifamily home in Yonkers NY, currently house hacking. I am looking for my next move! I would love a rental that offers multI-season attractions. I like to take weekend trips up to the Windham NY area because there is lots to do up there (Ski, hiking, kayaking, restaurants, vineyards, breweries etc). My vision is buying either a single or multi family house and renting it as an Airbnb. Does anyone have any advice on buying in the Windham area? Also should I be worried when researching on Airbnb that the market seems to be flooded with multiple Airbnbs in that area or is that a good sign that short term rentals are a hot commodity? Thanks in advance for any words of wisdom :)


Hi Kristen that whole area has seen an uptick in AirBnB activity. If yo are focusing one Windham and Hunter then you will see seasonal opportunities. I have 2 friends who bought 2 - 2 bedroom condos in that area. They usually rent them out the entire ski season to the same renters from Manhattan and they tell me that the income covers their year round mortgage and maintenance costs. One rents to a mother / daughter and the other to a young professional couple. Then during the summer they personally get to enjoy the homes for practically free.

I do not know any realtors in that area to recommend but would start by spending a weekend there and drawing circles around the areas you are interested in. Then start looking at what is for sale and then crunch your numbers.

Best of luck


Thanks for your reply, Rick!

I connected with a realtor last weekend and viewed some properties. Some areas certainly stand out more than others. I realize location is key when focusing on short term seasonal rentals. I am now set up to receive auto MLS emails when new properties come on the market that fit my criteria.

I see your in Chappaqua, I'm located in Yonkers. Do you know of any local meetups or real estate investing groups for newbies like myself? I am eager to learn more and make connections in the area. Thanks!

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