I'm in Staten Island so I see a lot of small multi family deals around the NYC area, though Port Chester is its own market. The first thing I'd check on any 2 to 4 unit is the actual rent roll versus what the listing claims, and what the taxes and insurance really run, since those two can swing the numbers a lot.
It would help to know if you plan to live in one of the units or buy it as a pure rental, and roughly what price range you're looking at. That changes the financing and what a good deal looks like, so happy to share what I've seen once I know more.
Hey Laurence, welcome. On a first multifamily the financing choice shapes a lot of the deal. If it's 2 to 4 units and you'll live in one, an owner-occupied loan like FHA or conventional can get you in with much less down. If it's purely an investment, a DSCR loan qualifies off the property's rent rather than your personal income.
Are you planning to live in it, and what price range are you seeing around Port Chester? Happy to run a couple of scenarios with you on a quick call. My direct line and email are on my profile.
Not market specific but my biggest concern with multi family is ease of resale. I want a quick exit plan in place before purchasing which has guided me toward Class A neighborhoods generally SFH or townhomes.
Welcome to the multifamily world, Laurence! A few things I'd add as someone who works with investors regularly: verify everything independently — get the actual leases plus 12 months of utility, tax, and insurance bills rather than taking the rent roll at face value, and confirm whether tenants are month-to-month or locked into leases. Also check that the certificate of occupancy matches the unit count; extra or unpermitted units are a common surprise in older NY stock. And Jimmy's question matters a lot — house-hacking a 2–4 unit versus buying purely as an investment are very different deals on financing and management. A local investor-friendly agent can help you sanity-check rents against actual comps before you write anything.
Laurence, I can’t offer firsthand Port Chester experience, but I’d pay close attention to the property’s documented unit count and permitted use before trusting the listing’s income figures.
From there, I’d review leases, payment history, owner-paid utilities, maintenance records, and upcoming capital work. The distinction between actual rent and projected market rent matters a lot when evaluating an occupied building.
I’d also have someone familiar with local requirements review the property before assuming a renovation or rent increase is feasible.
Are you looking at two-to-four units or a larger building, and would you occupy one of the units? That would help make the advice more specific.
I’m exploring multi-family properties in Port Chester, NY.
Anyone experienced / familiar with multi-families in that market?
@Laurence Wallace, @Jimmy Samaha and @Ametria Chaney brought up some good points. I'd also pay attention to what comes with the property when you buy it, especially if there are already tenants. I'd want to know whether anyone is behind on rent, if there are existing disputes, and how security deposits will be handled at closing. Those details can make a difference even when the numbers look good.
I'm a real estate attorney, broker, and investor based in Maryland, and I work with clients on rental properties, purchase agreements, and landlord-tenant matters. I've seen how important it is to understand the obligations you're taking on when buying a property with existing tenants. It's always better to address those questions before closing.
Thanks for starting this discussion, @Laurence Wallace! There's a lot to consider with multifamily properties beyond the purchase price. Are you looking at a property with existing tenants or one that's vacant? Happy to stay connected!
Good advice above on verifying the rent roll and the certificate of occupancy. A few things I'd add on the financing side, because in Westchester it shapes which buildings even make sense:
1. Unit count changes the loan. 2–4 units is residential financing: if you live in one, you can put down much less, and lenders count part of the other units' rent toward your income. At 5+ units it's a commercial loan, sized on the building's net operating income. Most lenders want a debt service coverage ratio of about 1.20–1.25x and 25–30% down, and the appraisal is based on income, not comps.
2. Check rent regulation before you underwrite. In New York, buildings with 6+ units built before 1974 can fall under rent stabilization if the municipality has opted in, and several Westchester municipalities have. If a building is covered, your rent growth and renovation plans are capped, so confirm its status with NY State Homes and Community Renewal before you offer.
3. Underwrite taxes at what they will be after the sale. Westchester property taxes are among the highest in the country, and a reassessment after the sale can wreck a deal that worked on the seller's numbers.
4. Expect older systems. A lot of Port Chester stock is pre-war, so budget for boilers, oil tank removal, and electrical work. Lenders will see the same things in the inspection and appraisal.
What price range and unit count are you looking at?