Mon-Sat: 7AM-9PM sunsethomeimprovement07@gmail.com

★★★★★ 5.0 · 49 Google reviews

G ★★★★★ 5.0 from 49 Google reviews · BBB A+ Accredited

Roofing Contractor in Jamaica Plain, MA

Jamaica Plain mixes triple-deckers with some of the finest Victorian housing in Boston. The Sumner Hill district alone holds Second Empire, Italianate and Queen Anne homes — mansards and complex multi-pitch roofs, not straightforward gables.

Get my free estimate 508-510-2233

20+Years on the roof

5.049 Google reviews

1 dayMost roofs finished

FreeWritten estimates

Free Jamaica Plain roof estimate

Tell us your street and what you are seeing — and whether the roof is flat, pitched or both. We come out and price it in writing.

Prefer to talk it through? Call 508-510-2233 — we answer Mon–Sat, 7 AM to 9 PM.

Licensed & insured · MA HIC #204689

Based on Turnpike St, South Easton

Free written estimates

5.0 stars · 49 Google reviews

BBB A+ accredited

Sunset Home Improvement crew starting a roof replacement on a Cape-style home

1874Annexed to Boston

Roofs in Jamaica Plain

Triple-deckers and Victorians,
side by side

JP took a different route into Boston than Dorchester did — it seceded from Roxbury in 1851 to form West Roxbury, then came into the city with West Roxbury in 1874. The housing reflects that layered history, and so do the roofs.

✓ Triple-deckers with flat roofs needing membrane rather than shingles
✓ Second Empire mansards with a near-vertical face and a low-slope top
✓ Queen Anne roofs with turrets, dormers and multiple intersecting pitches
✓ Italianate houses with shallow pitches and deep overhangs
✓ Slate still in place on some of the older Sumner Hill housing

What we see on Jamaica Plain roofs

Sumner Hill is
a different kind of job

The Sumner Hill Historic District — listed on the National Register in 1987, bounded by Seaverns Avenue, Everett Street, Carolina Avenue and Newbern Street — is a concentration of high-quality late-19th-century houses. A roof there is detailed work, not a day’s tear-off.

✓ Mansard transitions where the steep face meets the flat top
✓ Turret and dormer flashing that has to be formed rather than bought
✓ Original slate that may be worth repairing rather than replacing
✓ Flat triple-decker roofs elsewhere in JP with ponding and seam failures
✓ Tight streets and close neighbours making staging part of the planning
✓ Heavy mature canopy around Jamaica Pond, the Arnold Arboretum and Franklin Park

Permits in Jamaica Plain

Jamaica Plain is Boston,
so permits go through the city

Jamaica Plain is a Boston neighbourhood rather than a municipality, so there is no JP building department. Permits run through the City of Boston Inspectional Services Department. We establish which permit type applies and pull it for you. We hold Construction Supervisor License CS-118483 and HIC registration #204689.

Sunset Home Improvement crew on a roof job

A+BBB accredited

Licensed, local, accountable

Check us out before you let anyone on your roof.

Sunset Home Improvement Inc. is a South Easton company working up into Jamaica Plain. The owner has more than 20 years of hands-on roofing experience, and the person who quotes your roof is on your roof. Here is what you can verify before you call:

✓ Massachusetts Home Improvement Contractor registration #204689
✓ Massachusetts Construction Supervisor License CS-118483
✓ BBB Accredited Business with an A+ rating
✓ 5.0 stars across 49 Google reviews
✓ A written, itemized estimate before any work starts

Book a free inspection More about us →

Recent work

Our crews and trucks, on real jobs

View the full gallery

Sunset Home Improvement roof replacement — architectural shingles, finished — Roof replacementArchitectural shingles, finished

Sunset Home Improvement tear-off — down to the deck, new underlayment — Tear-offDown to the deck, new underlayment

Sunset Home Improvement on site — crew and trucks at a replacement — On siteCrew and trucks at a replacement

Sunset Home Improvement protected — tarped and ready overnight — ProtectedTarped and ready overnight

Sunset Home Improvement finished ridge — new shingles and ridge cap — Finished ridgeNew shingles and ridge cap

5.0

★★★★★

49 Google reviews

What your neighbors say

Forty-nine reviews. Not one below five stars.

★★★★★

“Chris and his team were fantastic to work with. Fast, efficient work and a great price too. Definitely refer my friends and family in the future for any home improvement needs.”

Michael LuuGoogle review

★★★★★

“I have a two-story cape with a large garage. The crew showed up at 7:30 AM… completely stripped my roof, put down barrier and shingles. Completely done in 12 hours.”

Joel HovanesianGoogle review

★★★★★

“Super up front about pricing! Handled everything amazingly and was very easy to work with.”

Justin JohnsonGoogle review

Jamaica Plain roofing questions

What JP homeowners ask us

Who issues my permit in Jamaica Plain?

The City of Boston Inspectional Services Department. JP is a Boston neighbourhood, not a separate town, so there is no local department.

Do you do flat roofs on triple-deckers?

Yes. Flat and low-slope roofs need a membrane system rather than shingles, and they fail in different places — seams, parapets and drains rather than open field.

My house has a mansard. Is that specialist work?

It needs care. The steep face and the low-slope top are effectively two different roofs, and the transition between them is where mansards usually fail. We look at both before quoting.

Is my house in the Sumner Hill district?

Sumner Hill is bounded roughly by Seaverns Avenue, Everett Street, Carolina Avenue and Newbern Street. Tell us your street and we will know what we are coming to look at.

I have slate. Should I replace it?

Not necessarily. Sound slate can often be repaired and outlive any asphalt roof. Tell us what you have and we will be honest about whether it is a job for us.

How did JP become part of Boston?

It seceded from Roxbury in 1851 to form West Roxbury, then was annexed to Boston along with West Roxbury in 1874 — four years after Dorchester.