Buy a two- or three-family, live in one unit, rent the others. Everybody has heard of it. Almost nobody has seen the four advantages laid out together, and it is the stacking that makes it work in Boston specifically.

Advantage one: you are buying a primary residence, not an investment

When you occupy one unit of a two-to-four-unit building, the loan is a primary residence loan. That means low-down-payment products, better rates, and eligibility for state and municipal assistance. An investor buying the identical building next door needs a substantially larger down payment at a worse rate.

This single distinction is the largest one, and it is available to you exactly once per property.

Advantage two: the assistance programs still reach this inventory

The state and municipal down payment programs carry a purchase price cap, reported at $675,000. Against a Greater Boston single-family median of $810,000, that ceiling reaches almost nothing in most of the region.

It still reaches real multifamily inventory in parts of Dorchester, Hyde Park, Mattapan, and just outside the city in Everett, Revere, Chelsea, and Malden — several of which also carry elevated municipal assistance. The Boston First-Time Homebuyer Program provides 3 percent of purchase price, up to $50,000 plus closing costs, for eligible households buying in Boston.

Advantage three: the residential exemption, which never appears in a pro forma

Boston's residential exemption applies to your principal residence. Live in one unit of a multifamily and you qualify on the building.

FY2026: up to $351,108 of assessed value removed, saving up to $4,353.74 at the $12.40 residential rate. An absentee owner of the identical building across the street gets none of it.

So you collect rent on two units and pay a tax bill roughly four thousand dollars lower than the investor competing with you. Over a seven-year hold that is thirty thousand dollars that exists purely because you live there.

Note that Somerville ($4,578), Cambridge ($3,403), and Everett ($2,582.70) run their own versions, so the same logic applies in those markets with different math.

Advantage four: the rent

Dorchester offers more space per dollar than almost anywhere in the city, and price per square foot in the range of $516 against a citywide figure near $675. Your units rent to people who want square footage rather than an address, and that demand is durable.

What the stacked math actually looks like

Take a three-family at $850,000 in Dorchester. Owner-occupant financing at a low down payment. Assistance reducing cash to close. Two units renting. Residential exemption reducing the tax bill by roughly $363 a month.

The number you personally carry each month can land below what the same buyer would pay for a one-bedroom condo in a more fashionable neighborhood — and in seven years you own a building rather than a unit.

I am not going to publish a fake spreadsheet with invented rents. Run it on the actual property with actual leases. But run all four advantages, not just the first one.

The five things that break it

You do not want the job. Screening tenants, repairs at inconvenient hours, and Massachusetts security deposit rules, which are unforgiving and where mishandled deposits create liability that follows the building. If you do not want that work, the numbers do not work either.

The leases you inherit. A valid lease survives the sale. You step into the landlord position on existing terms. If rents are twenty percent below market because the seller was good to long-term tenants, those are your rents until expiration — and the Boston lease cycle turns on September 1, so the timing is not yours to choose.

Deferred capital you did not price. Triple-deckers have roofs, porches, and often knob and tube. Rear porch replacement is a real number. Knob and tube is an insurance problem before it is a repair problem, because some carriers will not write a policy on it, which makes it a financing problem.

Lead paint. Any home built before 1978 is assumed to contain lead paint unless proven otherwise, and you cannot refuse to rent to families with children under six. If a child under six lives in the unit, the property must be deleaded or brought into Interim Control. Budget for it or buy a building that already has a Letter of Compliance.

Vacancy and turnover. Two units producing income for eleven months a year is not two units producing income for twelve.

What to look at before you offer

• Actual collected rent roll, not asking rents, with lease expiration dates
• Security deposit accounting: which bank, whose name, interest paid
• Estoppel certificates from each tenant
• Separate utilities, or not — this is a large operating variable
• Roof, porches, heating systems, electrical service, and any oil tank
• Lead compliance status and any Letter of Compliance or Interim Control
• Whether the legal use matches the physical use, because a third unit in the basement that was never permitted is a financing problem

Send me your budget and where you are looking and I will run this against real multifamily inventory — with the exemption and the assistance in the math, not left out of it.

Chris Remmes, Managing Broker, Remmes & Co. [email protected] | 617-398-0015