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Triple Deckers For Sale Jamaica Plain

There are currently 10 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 now10
Median list price$1,674,000
Median sold (12 mo)$1,385,000
Sold (12 mo)15

Current listings (10)

55 South St, Boston MA 02130
◆ 59
$2,595,000
55 South St, Boston
8 bd3 ba3,996 sqft
3-family · 4,125 sqft lot
Cap rate3.0%
Signal Score59
$/unit$865,000
eXp Realty LLC - Corporate Office
16-18-20 Plainfield St, Boston MA 02130
$2,795,000↓ $100k
16-18-20 Plainfield St, Boston
9 bd6 ba4,212 sqft
3-family · 5,640 sqft lot
Block Realty
177 Chestnut Avenue, Boston MA 02130
$1,475,000
177 Chestnut Avenue, Boston
9 bd3 ba3,144 sqft
3-family · 1,740 sqft lot
Arborview Realty Inc.
194 Boylston St, Boston MA 02130
$1,395,000↓ $55k
194 Boylston St, Boston
9 bd3 ba3,264 sqft
3-family · 3,588 sqft lot
Compass
39 Glen Rd, Boston MA 02130
$1,849,000↓ $41k
39 Glen Rd, Boston
11 bd6 ba3,519 sqft
3-family · 4,109 sqft lot
eXp Realty LLC
44 Mozart Street, Boston MA 02130
$2,675,000
44 Mozart Street, Boston
14 bd8 ba4,608 sqft
3-family · 2,500 sqft lot
Compass
6 Oakdale St, Boston MA 02130
$1,495,000
6 Oakdale St, Boston
5 bd3 ba2,959 sqft
3-family · 9,600 sqft lot
Gibson Sotheby's International Realty
8 Porter St, Boston MA 02130
$1,998,999
8 Porter St, Boston
8 bd3 ba2,997 sqft
3-family · 2,574 sqft lot
Home For All Realty LLC
12 Schiller St, Boston MA 02130
$1,499,000
12 Schiller St, Boston
8 bd3 ba3,381 sqft
3-family · 3,926 sqft lot
Keller Williams South Watuppa
9 Forbes St, Boston MA 02130
$1,200,000
9 Forbes St, Boston
10 bd3 ba3,789 sqft
3-family · 2,233 sqft lot
Prime Time Realty Group, Inc.

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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