The best-rated roofers serving West Roxbury / JP (Greater Boston, MA), independently researched and ranked on rating, review volume and genuine local reputation.
The best roofers in West Roxbury / JP, Greater Boston, MA are Penshorn Roofing, Brown Bros Roofing, Boston Exterior Remodeling, O'LYN Roofing and Connell Roofing. Each is an independently researched local operator, ranked on reputation, reviews and genuine local presence, and none paid to appear.
One business can feature above the Top 5 on this page, clearly labeled. A great way for a newer or smaller pro to get seen first.
Penshorn Roofing is a Jamaica Plain family business that has served Greater Boston since 1894, making it one of the oldest continuously operating roofers in the city, now run by cousins Don, Stu and Mark. The company offers factory-certified roof replacement and repair plus wider exterior work for homeowners, property managers and commercial clients across the Boston metro. Its exceptional longevity and hyper-local JP roots give it a standout reputation for accountable, generational craftsmanship right in the neighborhood.
Founded in 1932 on Hyde Park Avenue in Jamaica Plain and now based just over the line in Dedham, Brown Bros Roofing is a family-run firm with more than 90 years of history serving Boston's southwest neighborhoods. The team installs asphalt, slate and rubber roofing along with siding, gutters, windows and skylights, working with quality manufacturers like CertainTeed. Its long track record and strong, traceable local reviews make it a trusted choice for West Roxbury, Roslindale and JP homeowners.
Boston Exterior Remodeling is a Roslindale-based, locally owned company specializing in roofing, siding, windows, decks and historical exterior work, with a showroom serving the West Roxbury area. Owner Joe runs an in-house crew and the company never subcontracts its projects, a point it emphasizes for quality control. Holding an A+ BBB rating and consistently positive local feedback, it is a genuinely neighborhood-rooted option for JP, Roslindale and West Roxbury exteriors.
O'LYN Roofing is a family-owned and operated roofer established in 1974, headquartered in Norwood with an additional Boston office and over five decades serving Greater Boston and MetroWest. The company is an Owens Corning Platinum Preferred and CertainTeed-certified contractor, offering roof replacement, repair and gutter work backed by craftsmanship warranties. With tens of thousands of completed local projects and a well-earned review reputation, it comfortably covers West Roxbury and Roslindale from nearby Norwood.
Connell Roofing is a third-generation, family-owned roofing and exterior company founded in 1956, serving Metro-West Boston through to Cape Cod from its Wrentham base for over 60 years. A GAF Master Elite certified contractor, it handles roof installation, repair, doors and wider exterior projects for residential and commercial property owners. With a long family track record and a strong, well-documented review reputation, it is an established option that genuinely covers the West Roxbury area.
The best roofers serving West Roxbury / JP, Greater Boston, MA are based in and around Jamaica Plain, Dedham, Roslindale, Norwood and Wrentham. With the Northeast's four seasons and older housing stock to contend with, roofs take a real pounding, so a proven local pro makes all the difference, and we've done the legwork to surface only the operators worth calling.
Penshorn Roofing currently tops the list, but every business here earns its place the same way: we research each roofer genuinely operating near West Roxbury / JP, Greater Boston, weigh real customer reviews and ratings from sources like Google and the Better Business Bureau, and rank on merit. No business can pay into this list, the single featured spot above it is the only paid placement, and it's always clearly labeled.
| Business | Best for |
|---|---|
| 1. Penshorn Roofing | Consistent, top-reviewed service |
| 2. Brown Bros Roofing | Fast response and repairs |
| 3. Boston Exterior Remodeling | Professional workmanship |
| 4. O'LYN Roofing | Dependable service and value |
| 5. Connell Roofing | Everyday, all-round jobs |
Our current top picks are Penshorn Roofing, Brown Bros Roofing, Boston Exterior Remodeling, O'LYN Roofing and Connell Roofing. Every business is independently researched and ranked on merit, never paid placement.
We research every roofer genuinely operating in and around West Roxbury / JP, Greater Boston, then weigh real customer reviews and ratings from sources like Google and the Better Business Bureau, review volume, and a genuine local track record. No business can pay to appear in the ranked Top 5.
No. The ranked Top 5 is editorial and cannot be bought. The only paid option is the single featured spot above the list, which is always clearly labeled as featured.
Start with the five above, then get written quotes from two or three, read their most recent reviews, and confirm they cover your part of West Roxbury / JP, Greater Boston. A good roofer responds promptly, explains the work clearly, and is upfront about pricing.
We rank on independent reputation and reviews, not licensing checks. Requirements vary by state and trade, so always confirm a pro's current license and insurance directly with them before any work begins.
Own the featured spot above this Top 5, clearly labeled. A great way for a newer or smaller pro to get seen first. Early-adopter rate $19/month for your first 6 months, then $39/month.