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Home Services All Services Roof Replacement Roof Repair Storm Damage Repair New Roof Installation Metal Roofing Shingle Roofing Flat Roofing Commercial Roofing Gutter Installation Roof Inspection Emergency Roof Repair Skylight Installation About Locations All Locations Rutland, MA Springfield, MA West Boylston, MA Yarmouth Port, MA Boxford, MA Deerfield, MA Framingham, MA Huntington, MA Medway, MA Reviews Contact (877) 349-1553
★★★★★ 4.7/5 from 377+ reviews

Local Chestnut Hill Roofing Contractors

13+ years protecting Chestnut Hill homes and businesses. Serving Chestnut Hill and Northfield, Rutland, Springfield, West Boylston, Yarmouth Port.

📞 (877) 349-1553
13+
Years
500+
Projects
4.7
Rating
13+
Years Experience
500+
Projects Completed
4.7
Star Rating (377+ Reviews)
Licensed & Insured

Our Services

Our Roofing Services

Professional Roofing solutions for residential and commercial properties in Chestnut Hill.

roof replacement
FREE ESTIMATE

Roof Replacement

Full tear-off down to the decking, inspect every board, replace what's rotten, and install a complete roofing system from ice and water shield up. Most residential jobs finished in 1-2 days.

roof repair
SAME-DAY

Roof Repair

Missing shingles cause water intrusion through the exposed underlayment and decking. We don't just replace the missing shingle. We check the deck for moisture damage with a Protimeter pin meter, replace any compromised underlayment, and weave new CertainTeed Landmark shingles into the existing pattern.

storm damage repair
LICENSED

Storm Damage Repair

HAAG Certified Inspector on every storm claim we handle in Chestnut Hill. HAAG certification is the insurance industry standard for forensic roof inspection. Adjusters trust our reports. We document hail hits per square, wind creasing, and granule displacement. FM 4473 hail resistance ratings determine whether your roof qualifies for full replacement or spot repair.

new roof installation
TOP RATED

New Roof Installation

New construction roof installation following IRC Section R905 and local Chestnut Hill building code amendments. We calculate ventilation per IRC R806 (1:150 ratio reduced to 1:300 when 50% is within 3ft of ridge. Synthetic underlayment per ASTM D226, ice barrier per ASTM D1970 at eaves in freeze-thaw climate zones. Manufacturer-certified installation locks in the full system warranty.

metal roofing
GUARANTEED

Metal Roofing

Metal roofing in Massachusetts makes sense. It reflects heat, handles high winds, and sheds hail better than shingles. We install standing seam, corrugated, and metal shingle panels.

shingle roofing
INSURED

Shingle Roofing

Your shingle choice determines your warranty, your curb appeal, and how your roof handles Massachusetts weather. We'll show you samples, explain the differences, and let you pick what fits your budget. No pressure.

flat roofing
FREE ESTIMATE

Flat Roofing

Commercial flat roof replacement in Chestnut Hill starts with a core sample to check the existing insulation. If it's waterlogged, everything comes off. If it's dry, we can sometimes overlay. Saves you $2-$4 per square foot.

commercial roofing
SAME-DAY

Commercial Roofing

TPO is our most-requested commercial membrane in Massachusetts. Reflective, energy-efficient, and it welds together at the seams for a watertight bond. We install 60-mil and 80-mil systems with 15-20 year manufacturer warranties.

gutter installation
LICENSED

Gutter Installation

Gutters aren't glamorous, but they're protecting your foundation, your fascia, and your landscaping. We install seamless aluminum gutters custom-formed on-site from a roll of coil stock. No seams means no leaks.

roof inspection
TOP RATED

Roof Inspection

Our 27-point roof inspection covers: shingle condition, granule loss, nail pops, lifting tabs, ridge cap integrity, valley flashing, step flashing at walls, drip edge, pipe boot seals, vent function, soffit ventilation, gutter pitch, downspout capacity, fascia condition, decking (from attic if accessible), and visible signs of moisture in the attic. Written report with photos emailed same day.

emergency roof repair
GUARANTEED

Emergency Roof Repair

After we tarp and secure your roof, we document everything for insurance purposes. Photos, measurements, damage descriptions. Your adjuster gets a professional report, not a handwritten note.

skylight installation
INSURED

Skylight Installation

Vented skylights open to let hot air escape. Great for kitchens and bathrooms in Chestnut Hill. Fixed skylights are cheaper and simpler. Solar-powered options from VELUX qualify for the federal 30% tax credit through 2032.

Ready to Get Started?

(877) 349-1553

Free Estimates • Available 24/7 • Licensed & Insured

Why Choose Chestnut Hill Roofing & Maintenance?

Trusted by homeowners and businesses across Chestnut Hill.

Financing Available

A new roof is a big expense. We offer 12-month same-as-cash and low-interest financing through GreenSky and Hearth. Get your roof done now, pay over time.

Clean Job Sites

We run magnetic nail sweeps three times. Once during tear-off, once after install, once before we leave. Tarps on the ground, dump trailer in the driveway. Your yard looks the same when we're done.

Free Roof Inspection

We get on the roof, take photos, and give you an honest assessment. If you don't need work, we'll tell you. No charge, no obligation, no high-pressure sales pitch.

13 Years in Chestnut Hill

We've been roofing Chestnut Hill homes since before half these companies had a website. 13 years means we know the local codes, the weather patterns, and the materials that hold up here.

Our Work

Recent Projects

View All Projects →

Simple Process

How It Works

1

Free Roof Inspection

Our inspector walks the roof looking at shingle condition, flashing integrity, vent function, and signs of moisture underneath. 30-45 minutes for most Chestnut Hill homes.

2

Written Estimate

We email or text the proposal so you can review it at home. Questions? Call us. No pressure, no expiration date tricks, no "today-only" pricing.

3

Installation Day

No subcontractors. Our crews, our equipment, our supervision. A project manager checks in throughout the day and does a final quality inspection before cleanup.

4

Quality Check

Before we leave: magnetic nail sweep across the entire yard, driveway, and walkways. Dump trailer hauled off. Gutters cleaned out. Your property looks better than when we arrived.

Verified Reviews

What Our Customers Say

★★★★★ 4.7/5 from 377+ reviews
★★★★★

"They replaced our gutters along with the roof. Seamless aluminum, everything matches. No more overflow when it rains hard. Wish I'd done this years ago."

M
Mark B.
Chestnut Hill
★★★★★

"Had a flat roof leak on our commercial building downtown. Chestnut Hill Roofing & Maintenance patched it temporarily, then came back and did a full TPO replacement the next week. Solved a problem we'd been chasing for two years."

R
Rachel H.
Chestnut Hill
★★★★★

"Couldn't believe how clean the job site was when they left. Three passes with the magnet, swept the driveway, cleaned the gutters out. My wife said the yard looked better than before they showed up."

L
Linda A.
Chestnut Hill

Service Areas

Areas We Serve

Roofing Chestnut Hill and Northfield, Rutland, Springfield, West Boylston, Yarmouth Port for 13+ years. Every roof we install gets the same attention whether it's across town or across the county.

Northfield Rutland Springfield West Boylston Yarmouth Port Boxford Deerfield Framingham Huntington Medway

FAQ

Frequently Asked Questions

Poor ventilation causes premature aging. If your attic runs hot in summer and your shingles are curling at 15 years, bad ventilation is probably why. Missing shingles cause water intrusion and accelerate everything. We do a free inspection and give you a straight answer: repair, plan for replacement in 2-3 years, or replace now.

There's no single "best" shingle. It depends on what you need. For warranty coverage, GAF Timberline HDZ with Golden Pledge is the best in the industry. For wind resistance, Owens Corning Duration with SureNail locks down tight. For value, CertainTeed Landmark or IKO Cambridge give you solid performance at a lower price point. We carry all of them.

Yes. We offer 12-month same-as-cash, low-interest plans up to 144 months, and no-money-down options through GreenSky and Hearth. Credit approval takes about 5 minutes. A new roof is a major expense. Financing lets you get it done now without draining your savings.

You get two warranties: one from the manufacturer on the materials and one from us on the workmanship. As a GAF Master Elite contractor, we can offer the Golden Pledge. That's 25 years on workmanship plus 50 years on the shingle. Owens Corning and CertainTeed have similar programs. Our own workmanship warranty is in writing and covers installation defects.

Most residential roofs in Chestnut Hill are done in one day. We show up at 7 AM, tear off the old roof, install the new system, and clean up by end of day. Two-story homes, steep pitches, or large roofs might take two days. We never leave a house uncovered overnight.

Have more questions? Call (877) 349-1553

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

24/7 emergency service. Most appointments available within 48 hours.

Call Now — Free Estimate
📞 (877) 349-1553

★★★★★ 4.7/5 from 377+ Reviews  ·  Licensed  ·  Insured

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