
Boston Neighborhood · MA
Roofing Contractors in Jamaica Plain, MA
From the slate turrets on Moss Hill to the flat rubber decks behind Hyde Square, Jamaica Plain asks a roofer to know several trades at once. We work all of 02130, and Paulo writes the estimate himself.
- ZIP codes served
- 02130
- Neighborhoods
- Hyde Square · Jackson Square · Egleston Square · Stony Brook · Green Street
- Response
- Same-day emergency tarping
Jamaica Plain is the hardest neighborhood in Boston to roof with one product line. Inside a mile of Jamaica Pond you can look at a slate turret with copper valleys on Moss Hill in the morning and a ponding rubber deck behind Hyde Square in the afternoon. They are not the same job, and they are not the same crew day.
The hills carry the big houses. Moss Hill, Jamaica Hills, Sumner Hill and Pondside hold 1850 to 1910 Italianate, Queen Anne, Shingle Style and Colonial Revival single-families with eyebrow dormers, cross gables and roof planes that meet at three different pitches. Plenty still wear their original slate.
Downhill it changes fast. Hyde Square, Jackson Square, Egleston Square, Stony Brook and Green Street are triple-decker and two-family territory, packed tight along the Orange Line corridor, mostly hipped roofs with a flat central deck. Woodbourne is its own planned enclave of stucco and tile-influenced houses that matches nothing else in 02130.
We are based in Danvers and we work Boston every week. Call (209) 758-8550 and Paulo walks the roof himself.
Working around Jamaica Plain
Jamaica Pond · Arnold Arboretum of Harvard University · Forest Hills Cemetery · Loring-Greenough House (1760) · Samuel Adams Boston Brewery · Eliot Hall, home of the Footlight Club
Free Roof Estimate in Jamaica Plain
Slate, Copper and Multi-Plane Roofs on the Hills
A century under a maple and oak canopy is hard on copper. Valleys pinhole at the low end first, where wet leaf litter sits and never fully dries. On a Queen Anne off Everett Street or Greenough Avenue, the slate can still be sound while two valleys are quietly feeding water into the sheathing behind a dormer cheek.
Massachusetts reroofing rules settle one argument before it starts. Slate, clay tile, cement tile, wood shake and asbestos-cement tile must be stripped, never covered with an overlay. If a bidder offers to shingle over your slate, that is not legal work. We do honest slate roof repair across Boston and we will tell you straight whether a roof has fifteen more years of patching in it or needs to come off.
Pitch matters here too. Many of these roofs run 10:12 or steeper, and 780 CMR R905.1.2 requires the ice barrier to reach at least 24 inches inside the exterior wall line - and on slopes of 8:12 or greater, not less than 36 inches measured along the slope from the eave. The Massachusetts ice and water shield requirement is the line where cheap bids get cut.
Triple-Deckers and Two-Families from Hyde Square to Egleston
The three-decker form matured around 1890 and construction stopped region-wide by the 1930s, so every one of these buildings is now 100 to 140 years old. Under the covering you find board sheathing, not plywood. Boards shrink, cup and split, and they are the reason a tear-off estimate in Stony Brook should always include a per-sheet number for replacement decking.
- Near-zero side setbacks - staging goes up front and rear, and the neighbor gets a conversation before the truck arrives.
- Rear porch stacks block the back slope on most Green Street and Egleston buildings.
- Three to four stories of staging on a lot with no driveway, so dumpster placement gets planned first.
- A hipped perimeter with a flat central deck means two systems on one roof: shingles on the slopes, membrane on the deck.
- That central deck is where we do flat roof replacement with EPDM or TPO, tied into the shingle field with proper metal, not caulk.
Woodbourne, the Arborway and What the Trees Do
Jamaica Plain has more roof-adjacent tree canopy than almost anywhere in the city. The Arnold Arboretum, Forest Hills Cemetery, and the Olmsted frontage along the Jamaicaway and Arborway all drop debris into valleys and gutters from March through December. Undersized gutters overflow, ice forms at the eave, and the fascia rots from behind.
We size and hang gutters and downspouts for Boston homes to the actual roof area, not to whatever was up there before. On the big hillside roofs near Pondside and Moss Hill that usually means going up a size and adding a leader.
Permits and Historic Review in 02130
Jamaica Plain is Boston, so a residential reroof with no structural work goes through the Boston ISD short-form permit process. The fee is $20 for the application plus $10 per $1,000 of the work estimate. We pull it. You should never be asked to pull your own permit as the homeowner - that shifts the liability onto you.
On historic review, be careful who you believe. The Boston Landmarks Commission's designated local districts and architectural conservation districts are places like Beacon Hill, Back Bay, the South End, Bay Village, Fort Point Channel, Highland Park and Mission Hill Triangle. Jamaica Plain addresses generally sit outside them, so the ISD permit is usually the only approval in play. National Register listing, which several JP areas carry, does not by itself dictate what you put on your own roof. If you are unsure about your specific address, call the BLC at 617-635-1935 before you sign anything - where a district does apply, their approval has to come first or ISD will not issue the permit.
Snow, Ice and the 40 psf Number
Boston's design ground snow load is 40 psf under the 780 CMR Eighth Edition table - confirm the current value with the building official for your permit. Logan averages 49.2 inches of snow a year. The bigger enemy is the swing: roughly 92 days at or below freezing but only about 23 that stay below freezing all day. That 69-day gap melts and refreezes water inside slate seams, chimney mortar and flashing laps until they fail.
Ice dams follow the same math. Most JP dams start at a finished third floor or a knee-wall attic with no clear intake-to-ridge path. Fixing the roof without fixing the air is a repeat visit, so we look at attic ventilation and insulation on every estimate. If you own a three-family, read our field notes on preventing ice dams on a Boston triple-decker.
Where Else We Work Nearby
JP sits between several markets we cover weekly. We are on Victorian and mansard work in Brookline, on capes and ranches out in West Roxbury, and on three-deckers all over Dorchester. Same crew, same phone, same owner on the roof.

Jamaica Plain Specifics
What makes roofs in Jamaica Plain different
Every town in this market has its own failure modes. These are the ones we see here.
Copper valleys with a century of leaf litter on them
Original copper valleys on the Sumner Hill and Pondside Victorians fail from the bottom up. Wet oak and maple debris holds moisture against the metal and eats through in pinholes you cannot see from the ground. We open the valley, check the boards under it, and reline in matching gauge rather than smearing sealant over it.
Hillside lots with nowhere to stand a ladder
Moss Hill and Jamaica Hills sit on real grade. Driveways are short, retaining walls are close, and the low side of the house can be a full story below the high side. Staging and fall protection get planned before the estimate is written, and that plan is part of what you are paying for.
Flat central decks that hold water
Hipped triple-decker roofs off Hyde Square and Jackson Square carry a flat or near-flat deck in the middle. Old built-up roofing and short-lapped membrane pond there, and the leak shows up two rooms away. We rebuild pitch with tapered insulation where the framing allows and run the membrane properly up the parapet or curb.
Third floors finished without a ventilation path
A lot of 02130 houses gained a bedroom under the roof at some point. Insulation got stuffed to the deck, the eave intake got blocked, and now the roof runs warm all winter. That is the ice dam engine. It is an air and ventilation fix, not a shingle fix.
Tall brick chimneys and freeze-thaw
The 1850 to 1910 stock carries big chimneys with wide crowns and old step flashing buried in mortar joints. Boston's freeze-thaw cycling opens those joints every winter. Chimney flashing is the single most common leak source we find on the hills, and it is usually a half-day repair, not a new roof.
Most Requested Here
Roofing services we run most in Jamaica Plain
Ordered by what this housing stock actually needs, not by what is easiest to sell.
- 01Slate Roof Repair & Restoration in Jamaica PlainSlate, copper and historic roof work. Matched stone, copper hooks and bibs, no tar patches, and historic review handled before the permit is pulled.See details
- 02Roof Replacement in Jamaica PlainFull tear-off, deck repair and a code-correct ice barrier. Written scope, permit filed for you, magnet sweep at the end of every day.See details
- 03Flat & Low-Slope Roofing in Jamaica PlainFull tear-off and 60-mil EPDM rubber replacement for triple-deckers, row houses and mansard decks, with tapered insulation that ends ponding water for good.See details
- 04Flashing & Chimney Repair in Jamaica PlainStep, counter and cricket flashing rebuilt at chimneys, sidewalls and parapets. Crown and mortar repair above the roof line, water tested before we leave.See details
- 05Gutters & Downspouts in Jamaica PlainSeamless aluminum, steel and copper gutters rolled on site and hung on hidden hangers, with downspouts sized for New England downpours. Rotted fascia fixed first.See details
Recent Work
On roofs around Jamaica Plain
Stripped roughly 1,900 square feet of failing slate off a Queen Anne near Sumner Hill, replaced two pinholed copper valleys and the rotted boards under them, and had the staging down and the yard raked in four days.
Want addresses in Jamaica Plain you can drive by and look at? Ask when you call. We would rather you saw the work than read about it. Read our customer reviews.
FAQ
Roofing questions from Jamaica Plain homeowners
Usually no. The BLC's local historic and architectural conservation districts cover areas like Beacon Hill, Back Bay, the South End and Mission Hill Triangle, not Jamaica Plain generally. Most JP reroofs need only the ISD short-form permit. Call the BLC at 617-635-1935 to confirm your address, because where a district does apply, their sign-off has to come before ISD will issue anything.
No. Massachusetts reroofing rules require slate, clay and cement tile, wood shake and asbestos-cement tile to be removed, not recovered. Anyone who bids an overlay on a Moss Hill or Pondside slate roof is either uninformed or hoping you are. A proper tear-off also lets us see the board sheathing, which is where the real surprises live.
Front and rear, with the rear porch stack worked around and the abutter told in advance. Party walls and near-zero setbacks mean there is no room for error on debris control. We tarp the ground, keep the dumpster spot planned before day one, and magnet-sweep the walk and the street at the end of every day.
Mature canopy along the Arborway and the Emerald Necklace drops leaf and seed debris for most of the year, and it lands in the valleys first, then washes to the gutters. Two cleanings a year is realistic in 02130, and undersized gutters make it worse. Going up a size and adding a downspout often fixes it permanently.
All Pro Phoenix Roofing139 High St, Danvers, MA 01923
Get DirectionsOur shop is at 139 High St, Danvers — a short run to Jamaica Plain on I-93 and Route 1.
Popular in Jamaica Plain
The three we quote most often at addresses like yours.
- Slate Roof Repair & RestorationSlate, copper and historic roof work. Matched stone, copper hooks and bibs, no tar patches, and historic review handled before the permit is pulled.Learn more
- Roof ReplacementFull tear-off, deck repair and a code-correct ice barrier. Written scope, permit filed for you, magnet sweep at the end of every day.Learn more
- Flat & Low-Slope RoofingFull tear-off and 60-mil EPDM rubber replacement for triple-deckers, row houses and mansard decks, with tapered insulation that ends ponding water for good.Learn more
We also cover these areas near Jamaica Plain
See the full list of 34 Massachusetts communities we serve.
Free On-Site Inspection
Free roof inspection in Jamaica Plain — no obligation
We will climb it, photograph what we find, check the attic where we can get to it, and leave you with a written itemized estimate. If the roof has years left, we will tell you that instead.
- 5.0 from 4 Google reviews
- Licensed & fully insured in Massachusetts
- Written workmanship warranty on every roof
