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2 Family Homes For Sale Jamaica Plain

There are currently 11 multi-families for sale in Jamaica Plain. Jamaica Plain is a leafy, walkable neighborhood full of period two- and three-families, served by the Orange Line and the 39 bus. For investors it’s a lower-cap appreciation and value-add market. JP trades at premium prices and tighter caps, roughly 4.75–5.5%. Each listing below shows our Signal Score and an estimated cap rate.

For sale now14
Median list price$1,399,950
Median sold (12 mo)$1,495,000
Sold (12 mo)19

Current listings (11)

93 Moraine, Boston MA 02130
◆ 49
$2,295,000
93 Moraine, Boston MA 02130
2 units 10 bd4 ba4,995 sqft
Cap rate2.2%
Signal Score49
$/unit$1,147,500
22-24 Greenview Avenue, Boston MA 02130
$1,250,000
22-24 Greenview Avenue, Boston MA 02130
2 units 6 bd2 ba2,881 sqft
26 Adelaide Street, Boston MA 02130
$1,990,000
26 Adelaide Street, Boston MA 02130
2 units 5 bd4 ba2,689 sqft
27 Cranston Street, Boston MA 02130
$1,300,000
27 Cranston Street, Boston MA 02130
2 units 5 bd2 ba2,400 sqft
40-40A Newbern, Boston MA 02130
$975,000
40-40A Newbern, Boston MA 02130
2 units 2 bd3 ba1,750 sqft
15 Peter Parley Rd, Boston MA 02130
$1,199,000
15 Peter Parley Rd, Boston MA 02130
2 units 6 bd2 ba2,828 sqft
6-8 Marmion St, Boston MA 02130
$1,249,000
6-8 Marmion St, Boston MA 02130
2 units 7 bd3 ba2,902 sqft
6-8 Weld Hill St, Boston MA 02130
$1,799,000
6-8 Weld Hill St, Boston MA 02130
2 units 6 bd4 ba2,584 sqft
9 Parkwood Ter, Boston MA 02130
$1,849,999
9 Parkwood Ter, Boston MA 02130
2 units 9 bd3 ba3,579 sqft
9 South St., Boston MA 02130
$1,099,000
9 South St., Boston MA 02130
2 units 7 bd2 ba2,227 sqft
49 Jamaica St, Boston MA 02130
$1,499,900
49 Jamaica St, Boston MA 02130
2 units 6 bd3 ba2,168 sqft

Get new Jamaica Plain deals before they hit Zillow

Justin Rollo sends qualified investors fresh multi-family listings (and off-market deals) the day they come up.

Listings here are curated by Justin Rollo of Signal Real Estate, an investor-friendly agent who works this market every day. Jamaica Plain is one of the Greater Boston markets Signal Real Estate watches most closely for multi-family opportunities — reach out if you want to move on something before it’s widely listed.

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Questions & answers

Why invest in Jamaica Plain multi-family?

Jamaica Plain is a leafy, walkable neighborhood full of period two- and three-families. For investors it’s a lower-cap appreciation and value-add market. JP trades at premium prices and tighter caps, roughly 4.75–5.5%.

What cap rate do Jamaica Plain multi-families offer?

Greater Boston multi-families generally run a 4–5.5% cap, with value-add pockets reaching 6%+. JP trades at premium prices and tighter caps, roughly 4.75–5.5%. Each listing above shows an estimated cap rate based on area rents — directional, not an appraisal.

Can I house-hack a Jamaica Plain 2–4 unit?

Often yes — FHA allows 3.5% down on owner-occupied 1–4 units (note the self-sufficiency test on 3–4 units), and conventional now allows 5% down on 2–4 units. Justin Rollo of Signal Real Estate can run your numbers.

How do I see new Jamaica Plain multi-families first?

Sign up below and Justin Rollo will send matching listings — including off-market deals — as soon as they come up.

Justin Rollo, Broker Associate at Signal Real Estate
Justin Rollo — Broker Associate, Signal Real Estate · MA Lic. #9534264

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.

📞 978-790-4381📍 25 Braintree Hill Park, Suite 200, Braintree, MA 02184
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