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Top Roofing Services in Chestnut Hill, MA

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Premier Roofing Solutions for Norfolk County Homeowners — Coastal Windows & Exteriors

Chestnut Hill homeowners searching for top roofing services in Chestnut Hill, MA deserve a partner who understands this community’s elevated standards. Coastal Windows & Exteriors is the #1 woman-owned roofing company in New England, earning a 4.8-star Google rating across 600+ verified reviews. Whether your home needs asphalt shingles built to last 50+ years or a metal roof engineered to stand for 70+ years, our team brings certified craftsmanship to every project. Contact us today for a free estimate!

Our GAF Master Elite certification places us among only 2% of roofing contractors nationwide. From the tree-lined streets of Chestnut Hill to the estates bordering the Chestnut Hill Reservoir, we protect what matters most. Every roof replacement in Chestnut Hill, MA begins with a thorough inspection and ends with a 50-year comprehensive warranty covering unlimited wind speeds.

Canton homeowners care deeply about their properties — and we match that standard. Our GAF Master Elite certification puts us among only 2% of roofing contractors nationwide. Let’s talk about what your roof needs. We’d love to earn your trust.

Save Energy

Cobra Attic Ventilation reduces heat buildup and energy loss in every season. Your home stays more comfortable without overworking your HVAC.

Beautify Your Curb Appeal

Stunning shingle styles and refined metal roofing finishes transform your home’s first impression. Chestnut Hill’s architectural character deserves a roof to match.

Prevent Leaks

GAF Leak Barrier Protection seals your roof deck against water intrusion. Proper waterproofing means no surprises after the next nor’easter.

Top Return on Investment

Roof replacement delivers a 56% ROI according to national Cost vs. Value reports. Few upgrades protect your equity the way a quality new roof does.

Stop Ice Dams

Our 6-layer system blocks ice dams before they form. Proper ventilation and leak barriers keep melt water moving safely off your roof.

Lifetime Warranty

Our 50-year comprehensive warranty covers manufacturing defects and includes unlimited wind speed protection. It’s confidence you can count on for decades.

What Should I Look for in a Roofing Contractor in Chestnut Hill, MA?

The right roofing contractor in Chestnut Hill, MA combines verified credentials with proven local experience. Certification level, warranty terms, and reputation all separate great contractors from average ones.

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Key Qualities That Define a Top Roofing Contractor

  • GAF Master Elite Certification: This elite designation is awarded to only 2% of roofing contractors nationwide. It requires rigorous training, insurance compliance, and customer satisfaction standards. Coastal Windows & Exteriors holds this distinction.
  • Verified Google Reviews: Look for contractors with 600+ verified reviews and a 4.8-star rating or above. Volume and consistency signal a track record you can trust for your Chestnut Hill home.
  • Comprehensive Warranty Coverage: Top contractors offer 50-year warranties with unlimited wind speed coverage. A weak warranty is often the first sign of a company cutting corners.
  • Woman-Owned and Award-Winning: Coastal Windows & Exteriors is the #1 woman-owned exterior remodeling company in New England (INC 5000) and a recipient of the SBA Business Person of the Year award.
  • Transparent, No-Pressure Estimates: Reliable contractors provide clear, detailed estimates before any work begins. Ambiguity in pricing is a red flag for Chestnut Hill homeowners.
  • Financing Access: Top roofing companies offer flexible financing up to 20 years so a needed roof replacement in Chestnut Hill, MA doesn’t have to wait.
  • 7,000+ Installations Completed: Experience matters. Our team has protected Massachusetts homes at scale, and that depth of knowledge shows in every installation we complete.

How to Choose the Right Roofing Contractor for Your Chestnut Hill Home

Top Recommendation: Choose a GAF Master Elite contractor with 600+ verified reviews and a 50-year warranty for the best Chestnut Hill roofing experience.

Best for First-Time Buyers: Contractors with free in-home consultations and no-pressure estimates.

Best for Premium Projects: Award-winning roofing companies offering comprehensive system warranties and long-term financing.

Ready to find the right roofing contractor in Chestnut Hill, MA? Coastal Windows & Exteriors offers free estimates with no obligation.

Last Updated: April 2026

Sources:

  • Homeowners should inspect their roof at least twice a year, in spring and fall. GAF Residential Roofing FAQs, GAF’s official guidance on roof inspection frequency and maintenance schedules. (2025)

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How Long Does a Roof Last in Chestnut Hill, MA?

A well-installed roof in Chestnut Hill can last 50 or more years depending on the material. Roofing lifespan varies based on material type, installation quality, and maintenance habits.

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Roofing Lifespan by Material Type

  • Asphalt Shingles: Quality asphalt shingles last 50+ years when installed by a certified contractor. GAF’s Timberline HDZ shingles carry a lifetime warranty against manufacturing defects and the industry’s strongest wind protection.
  • Metal Roofing: Metal roofs are built to last 70+ years in New England’s climate. Their resistance to snow load, ice expansion, and moisture makes them ideal for Chestnut Hill homes.
  • Inspection Cadence Matters: Inspect your roof at least twice a year — in the spring and fall — to catch minor issues before they become costly repairs. Early attention adds years to any roof’s life.
  • When to Call a Pro: If your roof is more than 20 years old or shows recurring issues, consult a roofing professional about replacement. Delaying can lead to interior water damage and escalating costs.
  • Ventilation Extends Lifespan: Proper ventilation allows warm air to shift out through vents and be replaced with cooler air. It reduces condensation, protects insulation, and prevents mold — all of which add years to your roof.
  • Installation Quality Is the Deciding Factor: Even the best materials underperform without expert installation. A GAF Master Elite roofing company in Chestnut Hill, MA ensures your system is built to last.
  • 7,000+ Installations Completed: Coastal Windows & Exteriors has installed roofs across Massachusetts for years, and that hands-on experience shows in every project we complete.

Which Roofing Material Is Right for Your Chestnut Hill Home

Top Recommendation: Asphalt shingles for budget-conscious homeowners needing 50+ years of dependable protection.

Best for Maximum Longevity: Metal roofing for Chestnut Hill homes built to last 70+ years with minimal maintenance.

Best for Peace of Mind: GAF Master Elite installation with a 50-year comprehensive warranty and unlimited wind speed coverage.

Ready to protect your Chestnut Hill home with a roof built to last? Schedule your free estimate with our team today.

Last Updated: April 2026

Sources:

  • Roofs more than 20 years old with extensive damage or recurring issues should be evaluated by a roofing professional for replacement. GAF Residential Roofing FAQs, GAF’s official guidance on roof lifespan, inspection frequency, and replacement thresholds. (2025)
  • Proper ventilation allows warm air to shift out through vents, reduces condensation, and keeps insulation in good condition. GAF Best Roofing Materials and Colors for Energy Efficiency, GAF’s guidance on ventilation and energy-efficient roofing performance. (2024)

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Get Your Free Roofing Estimate in Chestnut Hill

Coastal Windows & Exteriors proudly serves Chestnut Hill and neighboring Norfolk County communities throughout the South Shore. Whether your home sits near the Chestnut Hill Reservoir, the Country Club District, or along the tranquil streets bordering Newton, our team comes to you. We’ve completed 7,000+ installations across Massachusetts — and your neighborhood is next. Reach out to discover why so many homeowners searching for top roofing services in Chestnut Hill, MA choose Coastal above all other roofing companies.

Serving Greater Boston, South Shore, South of Boston, and the western suburbs of Boston.

Your Special Note from the Owner

Green 5 Stars

Chestnut Hill is a place that stops you in your tracks. The reservoir. The historic homes. The streets that feel like they’ve been here forever — because they have. Every time our crew pulls up to a Chestnut Hill property in Norfolk County, I feel the weight of what we’re protecting. These aren’t just houses. They’re generational homes, and the roofs over them matter deeply.

Our top roofing services in Chestnut Hill, MA are designed for this community’s specific needs — homes with character, with history, and with owners who expect nothing short of excellence from any contractor they invite onto their property. The South Shore rewards craftsmanship, and we show up ready to deliver it every single time.

I’m proud of every project we’ve completed in this community, and I look forward to protecting Chestnut Hill homes for many years ahead!

— Stephanie, Owner, Coastal Windows & Exteriors

Frequently Asked Questions About Roofing in Chestnut Hill, MA

Can Ice Dams Cause Roof Leaks and Water Damage in Chestnut Hill?

Ice dams are one of the leading causes of roof leaks and interior water damage in Massachusetts. Chestnut Hill homeowners should understand how they form and what prevents them.

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How Ice Dams Form and What They Destroy

  • The Formation Cycle: Snow on a warm roof melts and flows toward the cold eave, where it refreezes. As the cycle continues, a wall of ice builds up and forces melt water back under the shingles.
  • Ice Dam Removal Costs Add Up Fast: Removing an ice dam can cost up to $4,000. That’s before addressing any damage left behind.
  • Interior Water Damage Is Real: After ice dam removal, roof leak repair alone can reach up to $24,000 depending on the extent of damage to your Chestnut Hill home.
  • Shingle and Gutter Damage Follow: Shingle repairs after an ice dam event run $130–$9,000. Gutter cleaning costs an additional $75–$400, and snow removal adds $200–$700.
  • Heat Cable Installation Prevents Future Events: Proactive heat cable installation runs $500–$4,600 — far less than the combined cost of repairing damage a single ice dam season can cause.
  • Insulation Damage Is Often Hidden: Wet insulation loses its ability to perform over time. Ice dam damage may not appear immediately but compounds quietly over multiple winters.
  • Our 6-Layer System Addresses the Root Causes: Every top roofing service in Chestnut Hill, MA we complete includes Cobra Attic Ventilation and Leak Barrier Protection — the two most effective defenses against ice dam damage.

Your Best Options for Ice Dam Protection in Chestnut Hill

Top Recommendation: Combine leak barrier protection with a properly ventilated roofing system for full ice dam defense.

Best for Immediate Protection: GAF Leak Barrier at the eaves as a first measure against water infiltration.

Best Long-Term Solution: Full roof replacement in Chestnut Hill, MA using our 6-layer system with Cobra ventilation.

Don’t let ice dams compromise your Chestnut Hill home this winter. Contact us for a free roofing assessment today.

Last Updated: April 2026

Sources:

  • Professional ice dam removal can cost homeowners up to $4,000. Angi Ice Dam Removal Cost, Angi’s cost guide covering ice dam removal pricing and related repair expenses. (2025)
  • Shingle repairs following ice dam damage can range from $130 to $9,000. Angi Ice Dam Removal Cost, Angi’s cost guide covering ice dam removal pricing and related repair expenses. (2025)
  • Roof leak repair costs can climb as high as $24,000. Angi Ice Dam Removal Cost, Angi’s cost guide covering ice dam removal pricing and related repair expenses. (2025)
  • Gutter cleaning typically costs between $75 and $400. Angi Ice Dam Removal Cost, Angi’s cost guide covering ice dam removal pricing and related repair expenses. (2025)
  • Snow removal following an ice dam event typically costs $200–$700. Angi Ice Dam Removal Cost, Angi’s cost guide covering ice dam removal pricing and related repair expenses. (2025)
  • Heat cable installation runs $500–$4,600 as a preventative measure against ice dam formation. Angi Ice Dam Removal Cost, Angi’s cost guide covering ice dam removal pricing and related repair expenses. (2025)

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Finding a reliable roofing contractor in Chestnut Hill, MA means checking credentials, verified reviews, and warranty terms before signing anything. Not all contractors offer the same level of accountability.

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How to Evaluate Roofing Contractors in Chestnut Hill

  • Start With GAF Master Elite Status: This certification is awarded to only 2% of roofing contractors nationwide. It requires consistent customer satisfaction, insurance compliance, and professional development. It’s the gold standard for Chestnut Hill homeowners.
  • Check Google Review Volume and Quality: Look for contractors with 600 or more verified reviews. A 4.8-star rating at that volume signals reliable, repeat performance — not just a few good jobs.
  • Ask About Warranty Terms: A trustworthy contractor backs their work with a 50-year comprehensive warranty. Unlimited wind speed coverage separates true craftsmen from bargain-bin bidders.
  • Confirm Insurance and Licensing: Reliable contractors carry full liability insurance and appropriate state licensing. Request documentation before any work begins on your Chestnut Hill home.
  • Look for Community Recognition: Awards like the SBA Business Person of the Year and Best of North Shore reflect a contractor’s standing in the community — not just a self-proclaimed reputation.
  • Evaluate Transparency From Day One: A trustworthy roofing company in Chestnut Hill, MA provides clear estimates, defined timelines, and honest assessments. Evasive answers at the estimate stage predict problems at installation.
  • Financing Availability Signals Stability: A contractor offering financing up to 20 years is a financially stable business with lender relationships — a strong indicator of reliability.

What to Look for When Comparing Chestnut Hill Roofing Companies

Top Recommendation: Prioritize GAF Master Elite contractors with 600+ verified reviews and a 50-year warranty for the most reliable Chestnut Hill roofing experience.

Best for Budget-Conscious Homeowners: Contractors offering flexible financing and transparent, itemized estimates.

Best for Complex Projects: Award-winning companies with proven track records on high-end residential properties.

Ready to work with a contractor Chestnut Hill homeowners trust? Start with a free estimate from Coastal Windows & Exteriors.

Last Updated: April 2026

Sources:

  • Homeowners should inspect their roof at least twice a year, in spring and fall. GAF Residential Roofing FAQs, GAF’s official guidance on roof maintenance and when to consult a roofing professional. (2025)

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Timing a roof replacement in Chestnut Hill, MA correctly saves money and prevents interior damage. Several clear signs tell you a replacement is overdue.

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Signs It’s Time for a Roof Replacement

  • Age Is the Most Reliable Indicator: If your roof is more than 20 years old and showing recurring issues, consult a roofing professional about replacement. Repairs on an aging system often cost more than starting fresh.
  • Shingles Show Visible Wear: Curling, buckling, or missing shingles signal the end of a roof’s useful life. A failing shingle system exposes your roof deck to water infiltration with every storm.
  • Granule Loss in Gutters: Finding granules in your gutters means your asphalt shingles are degrading. Once granule loss accelerates, the waterproofing layer fails quickly.
  • Daylight in the Attic: Visible light through the attic ceiling means gaps exist in your roof structure. This is a serious warning sign requiring immediate attention.
  • Sagging Roof Sections: A sagging deck indicates structural compromise — often from long-term moisture infiltration. This is beyond repair territory and requires full replacement.
  • Rising Energy Bills: A failing roof loses its insulating capacity. If your heating and cooling costs rise without explanation, your roof’s ventilation system may be failing.
  • ROI Makes Replacement Worthwhile: Asphalt roof replacement delivers a 68% ROI and metal roof replacement delivers a 50% ROI, according to the 2025 Cost vs. Value report. Acting before a total failure protects your equity and your home.

The Right Replacement Strategy for Your Chestnut Hill Roof

Top Recommendation: Replace any roof over 20 years old with recurring issues before the next New England winter arrives.

Best for Partial Damage: Schedule a professional inspection to confirm whether repair or full replacement is right for your Chestnut Hill home.

Best for Planning Ahead: Finance your roof replacement in Chestnut Hill, MA early and lock in current pricing before seasonal demand rises.

Is your Chestnut Hill roof showing any of these signs? Contact Coastal Windows & Exteriors for a free inspection today.

Last Updated: April 2026

Sources:

  • Roofs more than 20 years old with extensive damage or recurring issues should be evaluated by a roofing professional for replacement. GAF Residential Roofing FAQs, GAF’s official guidance on roof replacement thresholds and maintenance. (2025)
  • Asphalt roof replacement delivers a 68% ROI and metal roof replacement delivers a 50% ROI. JLC Online 2025 Cost vs. Value, national cost vs. value data for roofing replacement projects. (2026)

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Roof flashing is a thin metal barrier that seals joints and transitions where water is most likely to penetrate. It’s one of the most critical — and most overlooked — components of any roofing system.

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What Flashing Does and Where It Lives

  • Flashing Seals the Vulnerable Points: Every place your roof changes direction or meets a wall, chimney, skylight, or vent is a potential leak entry point. Flashing covers these transitions and channels water away from the structure.
  • Where You’ll Find It: Common flashing locations include chimney bases, roof valleys, skylights, vent pipes, and side walls. Each requires precise installation to perform correctly.
  • Poorly Installed Flashing Is a Top Cause of Leaks: Many roof leaks originate at flashing joints — not at the shingles themselves. This is true on Chestnut Hill’s older Colonial and Tudor-style homes with complex rooflines.
  • Flashing Materials Matter: Quality flashing uses durable metals that resist corrosion and expand and contract with temperature changes. Massachusetts temperature swings make this critical.
  • Flashing Works With the Full System: Our GAF 6-layer approach treats flashing as part of a complete waterproofing strategy — not an afterthought. Leak Barrier Protection and Roof Deck Protection work alongside flashing for complete coverage.
  • Inspect After Every Major Storm: Flashing can lift, crack, or separate over time. A post-storm inspection catches flashing issues early, before water reaches your interior ceiling.
  • A Top Roofing Service Includes Flashing Assessment: Every top roofing service in Chestnut Hill, MA we complete includes a full review of existing flashing conditions before installation begins.

Flashing Recommendations for Chestnut Hill Homeowners

Top Recommendation: Have flashing inspected any time your roof is over 15 years old or after a major storm — especially on homes with dormers or chimneys.

Best for Older Chestnut Hill Homes: Full flashing replacement paired with a complete roof replacement in Chestnut Hill, MA for a fully integrated waterproofing system.

Best for Peace of Mind: Schedule a free inspection with our certified team to assess your roof’s current flashing condition.

Concerned about your roof’s flashing? Reach out to Coastal Windows & Exteriors for a free evaluation today.

Last Updated: April 2026

Sources:

  • Asphalt shingles cost $4.46 per square foot on average nationally. This Old House Roofing Facts and Statistics, roofing material cost data and industry statistics for homeowners. (2025)

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Financing Available—Apply Today and Get Started

Great roofing shouldn’t have to wait for the perfect financial moment. Coastal Windows & Exteriors makes it straightforward to move forward with financing up to 20 years-free financing options and flexible payment plans built for a wide range of budgets. Our quick application takes under 10 minutes, and you’ll know your options fast. Explore financing up to 20 years and discover how manageable a lasting new roof can be. Book online today and save.

Protect your home from winter weather with energy-efficient windows, siding, roofing, and doors

The Long-Lasting Case for Metal Roofing in Chestnut Hill

Something remarkable happens when you put a metal roof on a classic New England home. The lines get cleaner, the profile gets sharper, and suddenly the house looks like it was always meant to look that way. Metal roofing brings stunning finishes and a wide range of profile options that complement Chestnut Hill’s architectural character — from stately Colonials to elegant Tudors. Our collection features sophisticated options for every taste.

Metal roofs are engineered to last 70+ years, standing up to New England’s relentless freeze-thaw cycles, heavy snow loads, and coastal wind events without complaint. They shed snow beautifully, resist ice buildup, and require minimal upkeep over their extraordinary lifespan. If you want a roof that outlasts the mortgage on your Chestnut Hill home, metal roofing is worth a serious conversation.

solar shingles roof installation
The GAF 6-Layer Roofing System

A Six-Layer Shield Over Every Chestnut Hill Roof We Install

Our GAF 6-layer roofing system is a complete performance ecosystem — not just shingles on a deck:

  • Cobra Attic Ventilation: Maintains balanced airflow to regulate attic temperature and reduce ice dam formation
  • Leak Barrier Protection: Self-adhering membrane seals the roof deck against water at the eaves and valleys
  • Roof Deck Protection: Adds a weatherproof layer between shingles and the structural deck
  • Starter Strip: Seals the roof’s first course of shingles against wind-driven rain at the eaves
  • Ridge Cap: Crowns the roof at its peak, sealing the ridge line against wind and water infiltration


Every element works together. No single component carries the load alone!

Call today to schedule your free estimate for top roofing services in Chestnut Hill, MA.

About Chestnut Hill, MA

Chestnut Hill straddles the Newton and Brookline border in Norfolk County, zip code 02467, placing it just 6 miles from downtown Boston. Founded as a village district in the 19th century, this community grew around streetcar lines connecting it to the city. Today, The Street at Chestnut Hill, Boston College’s iconic campus, the Chestnut Hill Reservoir, and Hammond Pond Reservation define a neighborhood that blends urban access with genuine natural beauty.

The housing stock here reflects generations of careful investment — substantial Colonials, Tudor Revivals, and Arts and Crafts bungalows line the quiet streets. Homeowners in Chestnut Hill take pride in their properties and expect contractors who match that standard. The Greater Boston market continues to push home values upward, making a well-maintained, properly protected roof one of the smartest investments a South Shore homeowner can make.

Our Roofing Installation Process

Every project we complete in Chestnut Hill runs through a process built on transparency, craftsmanship, and respect for your home:

  • Free In-Home Inspection: Our certified team evaluates your current roof condition, identifies any structural concerns, and walks you through material and system options tailored to your home.
  • Detailed Estimate and Scope: You receive a clear, written estimate before we begin. No vague ranges, no surprise additions when the crew arrives.
  • Pre-Installation Preparation: We protect your landscaping, siding, and exterior surfaces before removing your old roofing system.
  • GAF 6-Layer System Installation: Our GAF Green Certified Roofers and GAF Master Elite roofing contractors install each layer in precise sequence — only 2% of contractors nationwide earn this certification.
  • Debris Removal and Site Cleanup: We leave your Chestnut Hill property cleaner than we found it, including magnet sweeps for any stray fasteners.
  • Final Walkthrough: We inspect every completed section with you before closing out the project and activating your 50-year warranty.

Trust the team Chestnut Hill homeowners call when they want their roof done right. Schedule your free estimate today.

How Much Does Roofing Cost in Chestnut Hill, MA?

Roof replacement pricing in Chestnut Hill, MA depends on several variables unique to your home and your goals. Here’s what shapes the final investment:

What Drives Your Roofing Cost

  • Roof Size and Pitch: Larger roofs and steeper pitches require more material and more labor. Both factors affect your final estimate directly.
  • Material Selection: The average cost to replace an asphalt roof in New England is $35,701. Metal roofing averages $56,282 in New England. Both figures are strong starting reference points for planning your Chestnut Hill project.
  • Per-Square-Foot Baseline: Asphalt shingles cost $4.46 per square foot on average nationally — a useful benchmark when estimating material costs for your specific roof size.
  • System Complexity: Homes with multiple dormers, chimneys, skylights, or complex rooflines require more detailed flashing work and additional labor time.
  • Existing Damage or Deck Replacement: If the roof deck shows rot or structural damage, additional work adds to the project scope and cost.
  • Ventilation and Accessory Needs: Cobra Attic Ventilation, Leak Barrier Protection, and Ridge Cap components are part of a complete system installation.
  • Financing Makes It Manageable: Coastal Windows & Exteriors offers financing up to 20 years so your roof repair in Chestnut Hill, MA doesn’t have to wait.

Finding the Right Roofing Investment for Your Chestnut Hill Home

Contact us for a free, no-pressure estimate and see exactly what protecting your Chestnut Hill home looks like. Our top roofing services in Chestnut Hill, MA deliver lasting value at a price you can plan around.


Last Updated: April 2026

Sources:

  • The average cost to replace an asphalt roof in New England is $35,701. JLC Online 2025 Cost vs. Value — New England, regional cost vs. value data for roofing replacement projects in New England. (2026)
  • A metal roof averages $56,282 in New England. JLC Online 2025 Cost vs. Value — New England, regional cost vs. value data for roofing replacement projects in New England. (2026)


Asphalt shingles cost $4.46 per square foot on average nationally. This Old House
Roofing Facts and Statistics, roofing material cost data and industry statistics for homeowners. (2025)

Honors That Reflect Our Commitment to Chestnut Hill Homeowners

SBA Small Business Person of the Year

This national recognition celebrates Coastal Windows & Exteriors’ business leadership, community investment, and outstanding service across Massachusetts and New England.

BONS 2023 & 2024 Winner

North Shore homeowners have voted us their top choice year after year, a community honor that means more to us than any corporate award.

Minuteman Service Award

Honorable mention for our Roofs for Heroes initiative serving those who serve.

#1 Woman-Owned Vinyl Siding Company in New England (Inc. 5000)

Stephanie built Coastal Windows & Exteriors on a foundation of integrity, education, and genuine care for homeowners across the South Shore and beyond.

GAF Master Elite Contractor

Awarded to only 2% of roofing contractors nationwide, this distinction requires a consistent record of professional excellence, proper insurance, and homeowner satisfaction — a standard we’re proud to meet every day.

SEASONAL DISCOUNTS AND FINANCING UP TO 20 YEARS OPTIONS ARE AVAILABLE NOW!

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