Looking for the outliers - who found success investing in NYC?

Question

Successful NYC investors — what's your story? I’m curious to hear your path. Did you use any creative financing tools like: seller financing, rent-to-own, HELOCs, subject-to deals (taking over the seller’s mortgage), Joint ventures or partnerships, or even a BRRRR strategy?

If you used one of these (or something totally different), where in the city did you do it, and what did the deal look like?

For context: I stepped in for a landlord who no longer wanted to manage their property in a rapidly growing area of Brooklyn (Greenpoint). Over the next nine years, the building’s value grew more than 300%. People tell me it’s rare — but I don’t actually think it is. Also, these fancy terms don't kick in when your intuition points you to an opportunity. It's more in hindsight you realize something was a "subject-to-deal" or "rent to own".

So I’d love to hear your wins, big or small. What worked for you in NYC? What surprised you?

James McGovern · Answer

I am seeing a significant uptick in NYC investors purchasing single family homes in Waterbury CT and renting them out

Joe Jor · Answer

Generally speaking:

1) Westchester is more of an appreciation market,

2) cash flowing properties can be found, but may require a lot of searching or renovations

3) A property may negatively cash flow several years before it crosses over to positive cash flow

4) SMFs are more likely to cash flow

5) Cash flowing properties are more likely to be found in more sketchy areas

Vikki Grodner · Answer

We are in the midst of looking for a rental in Westchester County. So while not NYC, it is in the vicinity. The reason for this is two fold. My son moved to a Westchester community and my husband and I bought a house to be near him and his family. To make the house make sense from an investment standpoint, however, we decided to rent it out when we are not there. The house has been rented as a midterm rental since May 2025 and will continue to be rented through May 2026. We bought the house to live in when we visit, so the fact that it has become an ongoing rental in the immediate term, defeats the purpose of owning it. It does, however, validate the need. So we are on the hunt for a house that can actually be a full-time midterm rental. The challenge is to find a place that makes sense financially. We will likely take a line of credit against our other investments to purchase this property.

Looking for the outliers - who found success investing in NYC?

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