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Triple Deckers For Sale Jamaica Plain

There are currently 9 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 now9
Median list price$1,599,000
Median sold (12 mo)$1,397,500
Sold (12 mo)18

Current listings (9)

3150 Washington St, Boston MA 02130
92
$1,325,000
3150 Washington St, Boston MA 02130
3 units 8 bd6 ba3,436 sqft
Cap rate5.8%
Signal Score92
$/unit$441,667
8 Haverford St, Boston MA 02130
87
$1,525,000
8 Haverford St, Boston MA 02130
3 units 9 bd4 ba3,615 sqft
Cap rate5.1%
Signal Score87
$/unit$508,333
177 Chestnut Avenue, Boston MA 02130
86
$1,549,000
177 Chestnut Avenue, Boston MA 02130
3 units 9 bd3 ba3,144 sqft
Cap rate5.0%
Signal Score86
$/unit$516,333
11 Priesing Street, Boston MA 02130
84
$1,599,000
11 Priesing Street, Boston MA 02130
3 units 9 bd3 ba3,210 sqft
Cap rate4.8%
Signal Score84
$/unit$533,000
14 Meehan St, Boston MA 02130
84
$1,599,000
14 Meehan St, Boston MA 02130
3 units 6 bd5 ba5,120 sqft
Cap rate4.8%
Signal Score84
$/unit$533,000
164 Boylston Street, Boston MA 02130
82
$1,649,000
164 Boylston Street, Boston MA 02130
3 units 8 bd6 ba3,278 sqft
Cap rate4.7%
Signal Score82
$/unit$549,667
12 Schiller St, Boston MA 02130
77
$1,749,000
12 Schiller St, Boston MA 02130
3 units 8 bd3 ba3,381 sqft
Cap rate4.3%
Signal Score77
$/unit$583,000
14 Gordon St, Boston MA 02130
71
$1,995,000
14 Gordon St, Boston MA 02130
3 units 6 bd5 ba3,651 sqft
Cap rate3.9%
Signal Score71
$/unit$665,000
55 South St, Boston MA 02130
59
$2,595,000
55 South St, Boston MA 02130
3 units 8 bd3 ba3,996 sqft
Cap rate3.0%
Signal Score59
$/unit$865,000

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 RolloBroker 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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