Everything from the Gutter Up · Since 1974
Expert Roofing & Gutters in Greater Boston — Since 1974
Everything from the gutter up. O'LYN Roofing is a family-owned roofing company serving Greater Boston and MetroWest for over 50 years — roof replacement, leak repair, slate and flat roofing, gutters, and skylights, backed by lifetime craftsmanship warranties.
- Family Owned Since 1974
- MA Registration #101297
- Lifetime Craftsmanship Warranties
- Owens Corning Platinum Preferred
What we do
Roofing & gutter services for Greater Boston
Over 50 years and 40,000+ projects across Greater Boston and MetroWest — from asphalt replacements to the slate and copper work that earned us the name "the Victorian Specialists."
Roof Replacement
Full replacements with durable, energy-efficient materials — built for New England weather.
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Roof Leak Repair
Fast, targeted repairs that stop water before it becomes structural damage.
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Asphalt Shingle Roofing
The proven, cost-effective choice — installed to manufacturer-certified standards.
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Slate & Specialty Roofing
The Victorian Specialists — slate, cedar, and copper for Boston's classic homes.
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Flat & Commercial Roofing
Modern low-slope systems for flat-roofed homes and commercial buildings.
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Gutters & Gutter Guards
Seamless aluminum, copper, fiberglass, and wood — plus guards that end the ladder trips.
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Skylights & Daylighting
Velux-certified skylight installation that brightens rooms without leaks.
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Roof Cleaning & Ice Melt Systems
Moss and algae removal, plus heated systems that stop ice dams before they form.
Learn more →The O'LYN difference
Trusted roofers dedicated to excellence since 1974
Three generations of Greater Boston homeowners have trusted O'LYN with the roof over their heads. Here's what that trust is built on:
- Live phone answeringA real person picks up — in-house customer support, not a call center.
- On-site project supervisorsEvery job has a supervisor on the roof making sure every detail is right.
- Lifetime craftsmanship warrantiesWe stand behind the work for as long as you own the home.
- Top manufacturer credentialsOwens Corning Platinum Preferred, CertainTeed, and Velux certified.
Our work
Recent projects around Greater Boston
Good to know
Frequently asked questions
Do you offer free estimates?
Yes — every project starts with a free on-site estimate and roof evaluation. You can also book a consultation by phone; a real person answers, not a machine.
Are you licensed and insured?
Yes. O'LYN Roofing carries MA Registration #101297 along with full liability and workers' compensation insurance, so your home and everyone on it are protected.
What warranties do you offer?
We stand behind our work with lifetime craftsmanship warranties. As an Owens Corning Platinum Preferred contractor, qualifying installations also carry some of the strongest manufacturer warranty tiers available.
Do you offer financing?
Yes — flexible financing options are available, so a roof that needs replacing now does not have to wait on a lump sum. Ask when you book your estimate.
How long does a roof replacement take?
Most residential replacements take one to three days once materials arrive, depending on the size and complexity of the roof. Slate, cedar, and structural work can take longer — we give you a clear timeline in your estimate.
What areas do you serve?
Greater Boston and MetroWest, from our offices in Norwood and Wellesley — including Newton, Needham, Dedham, Walpole, Brookline, Natick, Framingham, and the surrounding towns.
Can you fix ice dams in winter?
Yes. We remove ice dams safely and — better — install heated ice melt systems and improve ventilation so they stop forming in the first place. Never chip ice off a roof yourself; it damages shingles and it is dangerous.
Do you work on historic and Victorian homes?
It's a specialty — we're known as the Victorian Specialists. Slate, cedar, and copper roofing on historic Greater Boston homes is work we've been doing for decades.
Ready when you are
Free estimates across Greater Boston & MetroWest — and a real person answers the phone.