Coolidge corner station in Brookline, MA
Brookline, Massachusetts

Expert Roofing Contractors in Brookline, MA

Brookline's architectural variety makes roofing more than a one-size-fits-all job. Victorian homes with steep pitches. Brownstones with flat roofs. Multi-family buildings with complex drainage. And Massachusetts weather tests them all. Freeze-thaw cycles crack shingles. Ice dams back water under flashing. Wind tears at loose materials after nor'easters. If you're seeing missing shingles, water stains, or granules in your gutters, your roof needs attention. We've handled roofing across Brookline for 27 years and know what this climate demands.

Local Expertise

Why Brookline Homeowners Choose Faithful Build for Roofing

We've pulled permits through Brookline's Building Department at 333 Washington Street for years. The town uses the Accela online system, and we handle the entire process. For homes in Brookline's eight Local Historic Districts, we understand what the Preservation Commission expects before issuing a Certificate of Appropriateness. Victorian homes around Coolidge Corner have complex roof lines that need careful planning. Flat-roofed multi-family buildings require different waterproofing approaches. That experience shows in accurate estimates and work done right the first time.

Licensed & Insured

Family-Owned

27+ Years

Local Experts

Average Investment

$18,000

For roofing in Brookline

Typical Timeline

1-3 days

From design to completion

Permit Information

We handle all permitting through:

Brookline Building Department

617-730-2222

About Our Roofing Services in Brookline

Brookline homeowners face a unique combination of challenges. You've got historic architecture that demands precision work. You've got urban density that means protecting neighboring properties during installation. And you've got New England weather that never lets up on your roof.

The freeze-thaw cycle is relentless from November through April. Water gets into small cracks, freezes, expands, and makes those cracks bigger. That's how shingle damage compounds year after year. Ice dams form when heat escapes through the attic, melts snow on the roof surface, and that meltwater refreezes at the cold eaves. The ice builds up, traps water, and forces it under shingles where it damages decking and ceilings. Prevention requires proper attic ventilation, adequate insulation, and ice and water shield membrane at vulnerable areas. We see this constantly on Victorian homes with their steep roof sections meeting lower dormers.

The architectural complexity in Brookline is significant. Queen Anne homes have conical tower roofs, multiple dormers, and varied roof pitches meeting at complex valleys. Second Empire homes feature mansard roofs that require specialized flashing and materials. Brownstones and multi-family buildings often have flat or low-slope sections that need rubber membrane or TPO roofing rather than shingles. The larger estates in Chestnut Hill may have slate or copper that's original to the house. Each style requires different approaches and materials.

For homes in Brookline's Local Historic Districts, the Preservation Commission reviews any exterior alterations visible from public ways. Material choices need to respect architectural character. We've worked in the Cottage Farm, Pill Hill, and other districts and understand what commissioners look for. Proper documentation and appropriate materials prevent delays and ensure approval.

We install primarily architectural asphalt shingles from GAF, Owens Corning, and CertainTeed. For a typical Brookline home, you're looking at $15,000 to $30,000 depending on size, pitch, complexity, and access challenges. Flat roof sections using TPO or EPDM add different costs. Victorian homes with multiple dormers and steep pitches run toward the higher end. Smaller brownstone roofs might be $12,000 to $18,000.

Metal roofing makes sense for some Brookline homes, particularly those with ice dam problems. Metal sheds snow rather than holding it, dramatically reducing ice dam formation. The upfront cost runs roughly double asphalt, but you're looking at 50+ years of life versus 25-30. For historic homes where metal is appropriate, standing seam can work within district guidelines. Slate and copper restoration is available for homes where that's the right choice, though costs run $15-30+ per square foot for slate.

Our process starts with a thorough inspection. We look at the roof surface, check flashing around chimneys and dormers, examine valleys, and inspect attic ventilation when accessible. Some roofs have years left with targeted repairs. Others need replacement. We give you an honest assessment and a detailed written estimate with everything itemized.

We handle all permitting. For straightforward replacements, the Building Department permit typically takes 3-5 business days. Historic district work requires Preservation Commission review first. We manage both processes. Once permits are approved, most installations take 1-3 days depending on size and complexity. We protect landscaping, catch all debris, and haul everything away.

You get manufacturer warranties on materials and our written workmanship warranty on installation. About 90% of premature roof failures come from installation problems, not defective materials. Our warranty addresses that directly. We've been doing this for 27 years under the same family ownership. When issues come up, you reach someone who can actually help.

What's Included in Brookline

Complete roof tear-off and replacement
Architectural shingle installation
Roof deck inspection and repair
Ice and water shield protection
Proper ventilation systems
Flashing installation and replacement
Gutter and downspout services
Skylight installation and replacement
Chimney flashing and cricket installation
Comprehensive cleanup and disposal

Our Roofing Process in Brookline

1

Inspection and Estimate

We thoroughly inspect your roof including shingles, flashing, ventilation, and deck condition. We'll take measurements, assess any damage, and provide a detailed written estimate outlining all work and materials.

2

Material Selection

We'll discuss shingle options including color choices, warranty coverage, and durability ratings. Together we'll select the best option for your home and budget. We'll also review ventilation needs and any additional work recommended.

3

Scheduling and Preparation

Once you approve the estimate, we schedule your roof replacement. We order materials, arrange for dumpster delivery, and confirm the installation date. We'll provide guidance on preparing your property.

4

Tear-Off and Deck Inspection

Our crew removes all old shingles down to the deck and carefully inspects for any damage. Any needed deck repairs are completed. Debris is contained and removed throughout the day.

5

Installation

We install ice and water shield in vulnerable areas, followed by underlayment across the entire roof. New shingles are installed according to manufacturer specifications. All flashing is replaced or properly installed. Ventilation is ensured.

6

Cleanup and Final Inspection

We perform a thorough cleanup including magnetic sweeps for nails. Gutters are cleaned. We conduct a final inspection with you and provide warranty documentation and maintenance recommendations.

Key Benefits

Protects your home from water damage
Improves energy efficiency
Enhances curb appeal
Increases home value
Prevents ice dam formation
Reduces heating and cooling costs
Provides peace of mind
Extends your home's lifespan
Prevents costly interior damage
Backed by warranty protection

Investment Range

Starting From$15,000
Up To$120,000

Pricing varies based on project scope, materials, and Brookline specific requirements.

Ready to Get Started?

Contact us for a free consultation about your roofing project in Brookline.

Request Free Quote(774) 500-3772

Serving All Brookline Neighborhoods

Whether you're near Brookline Town Hall or in the surrounding neighborhoods, Faithful Build brings expert roofing services right to your door.

Brookline Town Hall

Coolidge Corner Theatre

Brookline Village Historic District

Larz Anderson Park

JFK National Historic Site

Frederick Law Olmsted National Historic Site

Brookline Public Library

Brookline High School

We proudly serve these Brookline neighborhoods:

Coolidge CornerBrookline VillageChestnut HillWashington SquareBeaconsfieldLongwoodReservoirSouth Brookline

Frequently Asked Questions

Roofing in Brookline: Your Questions Answered

Most roof replacements in Brookline run between $12,000 and $35,000 for asphalt shingles. The wide range reflects the architectural variety here. A straightforward brownstone flat roof might be $10,000-15,000. A typical colonial with moderate pitch runs $15,000-22,000. Victorian homes with steep pitches, multiple dormers, and complex valleys often hit $22,000-35,000 or higher. The main factors are roof size (measured in squares, one square equals 100 square feet), pitch steepness (steep Victorian roofs require more labor and safety equipment), and complexity. Chimneys, dormers, skylights, and intricate valley work all add time. Flat roof sections using TPO or EPDM membrane have different pricing than shingle work. Material choice matters too. Standard architectural shingles run $4-7 per square foot installed. Premium shingles cost more. Metal roofing starts around $10-14 per square foot. Slate or copper for historic restoration runs $15-30+ per square foot. We provide detailed estimates with line items so you see what drives each cost.
For a standard roof replacement with asphalt shingles, no. Most Brookline homeowners replacing their roof won't qualify for federal tax credits. The exception is certain energy-efficient materials. ENERGY STAR-certified metal roofing with reflective pigmented coatings or asphalt shingles with cooling granules can qualify for a federal tax credit up to $3,200 through December 2025. Solar roofing that generates electricity qualifies for the 30% Residential Clean Energy Credit. But if you're doing what most homeowners do, replacing worn shingles with quality architectural shingles, there's no tax credit. Don't let tax credits drive your decision unless energy efficiency was already a priority. For homes in Brookline's historic districts, material choices often need Preservation Commission approval anyway, which may limit options. We can point you toward qualifying products if energy efficiency matters to you and they're appropriate for your home.
Material determines lifespan. Asphalt shingles last 20-30 years. The architectural shingles we typically install last 25-30 years with proper installation and ventilation. Premium shingles can exceed 30 years. Metal roofing lasts 40-70 years. Standing seam and quality metal shingles routinely hit 50+ years with minimal maintenance. For Brookline's Victorian and historic homes, this longevity often makes the higher upfront cost worthwhile. Flat roofing materials vary. EPDM rubber roofing lasts 20-30 years. TPO membrane lasts 15-25 years. These are common on Brookline's multi-family buildings and brownstones. Slate roofing lasts 75-200 years depending on grade and is sometimes the appropriate choice for historic restoration. Copper lasts 70+ years. Massachusetts weather affects these numbers. Our freeze-thaw cycles and ice dam potential shorten roof life if installation wasn't done correctly. Proper ventilation, quality underlayment, and precise flashing details extend any roof's lifespan.
For your primary residence, generally no. The IRS treats roof replacement as a home improvement, not a deductible expense. You can't deduct the cost from taxable income the year you pay for it. There are limited exceptions. If you have a dedicated home office used regularly and exclusively for business, you might deduct a proportional share based on that space's percentage of your home. Rental properties allow depreciation of the roof cost over 27.5 years. Storm damage in a federally declared disaster zone may qualify for casualty loss deduction. When you eventually sell, a new roof adds to your cost basis, potentially reducing capital gains tax. But for most Brookline homeowners replacing their primary residence roof, there's no direct tax deduction. The value is protecting your home and maintaining its architectural integrity. Consult a tax professional for your specific situation.
Late spring through early fall offers the best conditions. May through October typically brings dry weather and temperatures that let roofing adhesives and sealants cure properly. Asphalt shingles need temperatures above 40-45 degrees to seal correctly. The sweet spot is often late spring (May-June) or early fall (September-October) when weather is stable and schedules aren't as packed as midsummer. That said, we do roofing year-round in Massachusetts. Winter installations work but have limitations. We can hand-seal shingles in cold weather, though snow and ice on the roof delay work. Winter projects may cost slightly more due to slower conditions and safety requirements. If your roof is actively leaking or failing now, don't wait months for ideal weather. We can protect your home regardless of season. If you have flexibility and want to plan ahead, booking in late winter for a spring start often gets better scheduling options.
Yes, we handle everything with Brookline's Building Department. Roof replacements require a building permit. We submit applications through the town's Accela online portal, pay permit fees, and schedule required inspections. You don't need to visit 333 Washington Street or coordinate with inspectors. That's on us. Standard permits typically take 3-5 business days for approval, depending on department workload. For homes in one of Brookline's eight Local Historic Districts, there's an additional step. The Preservation Commission must review and approve exterior work visible from public ways before the Building Department issues permits. This may add time but ensures work meets historic preservation standards. We understand this process and help prepare the right documentation. Permitting matters because unpermitted work creates problems. Insurance may not cover damage from unpermitted work. When you sell, unpermitted work shows up in inspections and can complicate the sale. We include permitting as standard because it protects you.
You get two types of coverage. First, manufacturer warranties on materials. We primarily use GAF, Owens Corning, and CertainTeed products, all offering limited lifetime warranties on architectural shingles. Metal roofing manufacturers typically offer 30-50 year warranties. Flat roofing materials like TPO and EPDM have their own warranty structures, usually 15-25 years. These manufacturer warranties cover defects in the materials. Second, and often more important, is our workmanship warranty. About 90% of premature roof failures result from installation problems, not material defects. Poor flashing around chimneys and dormers, inadequate ventilation, incorrect nailing patterns, improper valley work. Our written workmanship warranty covers issues from how the roof was installed. As certified installers, we can also offer enhanced warranties combining materials and labor coverage. GAF's Golden Pledge, for example, covers both for up to 25 years. We explain all options when providing your estimate.
Several signs indicate it's time. From outside, look for missing shingles after storms, curling or buckling at shingle edges, visible cracks, or dark streaks from algae. Check gutters after rain. Granules collecting there (the sandpaper-like coating) mean shingles are breaking down. Flat roofs show problems differently: ponding water, bubbling or blistering, visible seams separating. From inside, check your attic for daylight through the deck, water stains on underside of decking, or musty odors indicating moisture. Age matters significantly. Most asphalt shingle roofs last 20-30 years. Flat rubber roofs last 20-30 years. If yours is approaching those ages and showing wear, plan for replacement. Recurring ice dams often signal ventilation or insulation problems a proper replacement can fix. Rising heating bills sometimes trace back to poor roof insulation. We offer free inspections and give honest assessments. Sometimes repairs buy more time. Sometimes replacement is the right call. We'll tell you which you're facing.

We Also Serve Nearby Communities

In addition to Brookline, we provide expert roofing services throughout Greater Boston and Massachusetts.