Why 2–4 units are the Boston move
Boston’s neighborhoods weren’t built as single-family suburbs; they were built as two-families and triple-deckers — housing that pays for itself was the point a century ago, and it still is. That gives this market something most cities don’t have: a deep inventory of small buildings a regular buyer can own.
Three things make the category work here. The rental demand is structural — universities, hospitals, and the September 1 cycle keep units leased. The financing is favorable if you live in one unit, because you’re buying an income property on owner-occupant terms. And the stock is finite: nobody has built a triple-decker in decades, so well-located ones don’t have to be brilliant to be durable.
House hacking, plainly
Buy a 2–4 unit. Live in one unit — genuinely live there, for at least the period your loan requires. Rent the others. The rent covers a large share of the mortgage, the building helps you qualify for its own loan, and you’re building equity in an income property instead of paying someone else’s.
What it demands in exchange: you live next to your tenants, you take the 11 p.m. call about the water heater, and your home doubles as your business. Some people find that a fair trade for what it does to their cost of living; some don’t. Both are correct answers — the mistake is not running the numbers at all.
Owner-occupants can buy 2–4 units with surprisingly little down — 95–97% LTV loans, meaning 3–5% out of pocket: FHA from 3.5% (3–4 unit purchases must pass FHA’s rental self-sufficiency test), conventional programs from about 5%, and MassHousing / ONE Mortgage for eligible first-time buyers. Pure investor purchases require substantially more down at higher rates. Programs change; confirm current terms with a lender before you shop.
Where off-market deals actually come from
The portals show listings; most of the interesting buildings never become one. Off-market deals come from direct outreach to owners, from relationships with the attorneys, contractors, and managers who hear “I might sell” first, and from agents who treat sourcing as the job rather than a bonus.
That sourcing is the core of Jared’s practice — it’s how the development side of his business works: find the opportunity before it’s a listing, then stay with it through acquisition, development, and sellout. The same pipeline surfaces 2–4 unit buildings that fit investor and house-hack buyers, which is why his buyers see things Zillow can’t show them.
How Jared underwrites a building
The same checklist whether it’s his capital or a client’s:
- Actual rents, not pro-forma. Leases in hand, collection history, and what the units realistically rent for on the September cycle — not the listing’s “potential.”
- Every tenancy, in writing. Lease end dates, tenancies at will, deposits and how they were held — Massachusetts security deposit law is strict, and the obligations transfer to the buyer.
- Condition and capex, priced. Roof, systems, deleading status, deferred maintenance — as numbers in the deal, not surprises after it.
- Real expenses. Taxes, insurance, water, vacancy, maintenance — the versions that survive contact with ownership.
- The calendar. How the closing date and lease turnovers line up with September 1 — timing alone can swing the first year’s numbers.
- The exit. What the building is if plans change: rental hold, condo potential, or resale — and to whom.
Buying with tenants in place
Most Boston multifamilies trade occupied. That’s workable — often preferable, since day-one income is real — but the diligence is different: leases survive the sale, deposits and their obligations come with the building, and if your financing assumes you move in, the path to a vacant unit has to exist on paper before you commit. More in the FAQ.
Who this is for
Buyers treating the purchase as an investment they’ll live in or operate — first building or fifth — and owners thinking about what their building could become. If what you want is a single-family in the suburbs, Jared is the wrong agent and will tell you so; if it has a rent roll, this is the lane.
Common questions
Can a multifamily be my first-ever property?
Yes — in Greater Boston it’s common, because owner-occupant financing works on 2–4 unit buildings and the rent from the other units offsets the payment. The real prerequisites aren’t years of experience; they’re a workable down payment, honest underwriting, and the willingness to be a landlord on day one.
How much down do I need for a 2–4 unit?
If you’ll live in it: potentially very little — FHA starts at 3.5% (3–4 unit purchases must also pass FHA’s rental self-sufficiency test) and conventional owner-occupant programs start around 5%. As a pure investor, expect substantially more down and pricier financing. Terms shift constantly, so get quotes specific to the building type before you shop.
Do lenders count the rent toward my qualification?
Generally yes — on a 2–4 unit purchase, lenders can credit a large share of the market rent from the units you won’t occupy toward your qualifying income. That’s the quiet mechanism that makes house hacking work: the building helps you qualify for itself. Exact treatment varies by loan program.
Where do triple-deckers still exist around Boston?
They’re the signature housing stock of Dorchester, East Boston, and much of Somerville, Medford, and Everett, with two-families dense across the same map. The construction boom that built them ended a century ago — nobody is making more — which is a real part of why well-located ones hold value.
What’s the most common first-timer mistake with multifamilies?
Believing the listing’s pro-forma. Marketed rents, projected expenses, and “market rent potential” are sales copy, not underwriting. The building is worth what its actual leases, actual condition, and realistic expenses say it’s worth — which is exactly the analysis to do before the offer, not after the closing.
Working on a multifamily — or a first one?
Bring the address, the rent roll, or just the idea. The underwriting conversation is free and specific.