Aerial view of Central Street in Wellesley, MA
Wellesley, Massachusetts

Expert Roofing Contractors in Wellesley, MA

Wellesley homeowners expect quality in everything, roofing included. The estate homes, Georgian colonials, and classic Capes around town weren't built with cheap materials, and they shouldn't be roofed with them either. Massachusetts weather is the challenge. Ice dams form along eaves when attic heat melts snow that refreezes at the cold edge. Freeze-thaw cycles crack shingles. Wind lifts flashing around chimneys and dormers. If you're seeing granule loss, missing shingles, or water stains after storms, your roof is due. We've been handling roof work in this area for 27 years.

Local Expertise

Why Wellesley Homeowners Choose Faithful Build for Roofing

We've pulled roofing permits at Wellesley's Building Department on Worcester Street for years and know what inspectors expect. The colonials and estate homes around Wellesley Hills have steep pitches, multiple dormers, and complex valleys that require careful planning. Cape-style homes are notorious for ice dam problems if ventilation isn't done right. For homes in historic districts, the Historic District Commission reviews exterior work, so material choices need to respect architectural character. That local knowledge shows in accurate estimates and fewer surprises.

Licensed & Insured

Family-Owned

27+ Years

Local Experts

Average Investment

$18,000

For roofing in Wellesley

Typical Timeline

1-3 days

From design to completion

Permit Information

We handle all permitting through:

Wellesley Building Department

781-431-1019

About Our Roofing Services in Wellesley

A roof replacement in Wellesley is a significant investment. With median home values well above a million dollars, the stakes are real. Cut corners on materials or installation and you'll pay for it later with leaks, ice dam damage, or a roof that doesn't hold up to Massachusetts weather.

The climate here is hard on roofs. From December through March, temperatures swing above and below freezing regularly. That freeze-thaw cycle cracks shingles, stresses flashings, and creates problems at valleys where roof planes meet. Ice dams are a constant threat. When heat escapes through an under-insulated attic, it melts snow on your roof. That meltwater runs down and refreezes at the cold eaves, forming an ice barrier that traps water behind it. Prevention means proper attic ventilation, adequate insulation, and ice and water shield membrane at vulnerable points.

Architectural complexity matters too. Georgian colonials, Colonial Revival homes, and estate properties often have steep pitches, multiple dormers, and intricate roof lines. Dormers need precise flashing. Hand-cut valleys require careful underlayment work. Chimneys and skylights create penetrations that must be flashed correctly or they'll leak within a few years. For properties in the Cottage Street Historic District or other areas under Historic District Commission review, roofing materials need to be appropriate to the home's architectural period.

We install architectural asphalt shingles from GAF, Owens Corning, and CertainTeed. These are the materials that make sense for most Wellesley homes. Installed correctly with proper ventilation and ice and water shield, they'll give you 25-30 years. For a typical colonial, expect $15,000 to $30,000 depending on size, pitch, and complexity. Larger estate homes run higher. Premium designer shingles that mimic slate or cedar shake are available for homes where appearance is paramount.

Metal roofing is worth considering if you're planning to stay long-term. The upfront cost is roughly double that of asphalt, but metal lasts 50+ years and sheds snow instead of holding it, dramatically reducing ice dam risk. For historic homes, standing seam metal or metal shingles styled to look like traditional materials can work within district guidelines.

For genuine historic restoration, slate and copper remain options. Slate lasts over a century. Copper develops a beautiful patina and lasts 70+ years. Both require specialized installation and cost significantly more, but for estate homes where appearance and longevity are priorities, they deliver.

Our process starts with a thorough inspection. We get on the roof, examine the decking and flashing, and check attic ventilation when accessible. Some roofs have more years left with targeted repairs. Others need full replacement. We'll tell you honestly which situation you're facing. If replacement makes sense, you get a detailed written estimate with line items.

We handle all permitting through Wellesley's Building Department. The town uses ViewPoint Cloud for online applications. We submit the permit, pay fees, and schedule inspections. You don't need to visit Worcester Street or coordinate with inspectors. Most installations take 1-3 days depending on size and complexity. We protect landscaping during work and haul away all old materials.

You get two warranty types. Manufacturer warranties cover material defects. GAF, Owens Corning, and CertainTeed offer limited lifetime warranties on shingles. More important is our workmanship warranty. About 90% of premature roof failures stem from installation problems, not defective materials. Our written workmanship warranty covers installation quality.

We've been doing this work for 27 years under the same family ownership. When you call, you talk to someone who knows your project and can answer questions directly.

What's Included in Wellesley

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 Wellesley

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 Wellesley specific requirements.

Ready to Get Started?

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

Request Free Quote(774) 500-3772

Serving All Wellesley Neighborhoods

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

Wellesley Town Hall

Wellesley Free Library

Wellesley College

Morses Pond

Wellesley High School

Elm Bank Reservation

Wellesley Square

Wellesley Hills Station

We proudly serve these Wellesley neighborhoods:

Wellesley SquareWellesley HillsWellesley FarmsWellesley FellsCliff EstatesHunnewell

Frequently Asked Questions

Roofing in Wellesley: Your Questions Answered

Roof replacements in Wellesley typically run $15,000 to $35,000 for asphalt shingles, reflecting the larger homes and premium expectations in this market. A smaller Cape or ranch with a straightforward roof might be $12,000-18,000. A typical colonial with dormers and valleys runs $18,000-28,000. Larger estate homes with steep pitches, complex roof lines, and multiple dormers can push $30,000-45,000 or more. The main cost drivers are roof size (measured in squares, where one square equals 100 square feet), pitch steepness (steeper roofs require more labor and safety equipment), and complexity. Dormers, chimneys, skylights, and hand-cut valleys add precision work. Material choice matters. Standard architectural shingles run $4-7 per square foot installed. Premium designer shingles that mimic slate or cedar cost more. Metal roofing starts around $10-14 per square foot. Slate for historic restoration runs $15-30+ per square foot. We provide detailed written estimates with line items so you understand exactly what drives the cost.
For a standard roof replacement with asphalt shingles, no. Most Wellesley homeowners replacing their roof won't qualify for federal tax credits. The exception is certain energy-efficient roofing 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. Wellesley adopted the Stretch Energy Code in 2011, which does require more energy-efficient building practices, but that's a code requirement rather than a tax benefit. For historic homes, material choices are often driven by architectural appropriateness rather than energy credits. We can point you toward qualifying products if energy efficiency is a priority and appropriate for your home.
Material determines lifespan. Asphalt shingles last 20-30 years. The architectural shingles we typically install last 25-30 years when properly installed with adequate ventilation. Premium designer shingles can push past 30 years. Metal roofing lasts 40-70 years. Standing seam metal and quality metal shingles routinely hit 50+ years with minimal maintenance. For Wellesley's estate homes, metal can make sense given the long-term investment perspective. Slate roofing lasts 75-200 years depending on the grade. Hard slate (S-1 grade) can exceed a century. It's the longest-lasting material but also the most expensive, typically only installed on historic homes or high-end properties where appearance and longevity justify the cost. Copper lasts 70+ years and develops a natural patina. Rubber roofing (EPDM) on flat sections lasts 20-40 years. Massachusetts climate affects these numbers. Our freeze-thaw cycles and ice dam potential can shorten lifespans if installation isn't done correctly. Proper ventilation, quality underlayment, and precise flashing work extend the life of any roof.
For your primary residence, generally no. The IRS treats a roof replacement as a home improvement, not a deductible expense. You can't deduct the cost from taxable income in 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 portion proportional to that office space percentage. If it's a rental property, you can depreciate the roof cost over 27.5 years. If your roof was damaged in a federally declared disaster, you may claim a casualty loss. When you eventually sell your home, a new roof adds to your cost basis, which can reduce capital gains tax. But for most Wellesley homeowners replacing their primary residence roof, there's no direct tax deduction. The value is in protecting your investment and maintaining your home's architectural integrity. Given Wellesley's high property values, a quality roof protects a significant asset. Consult a tax professional for your specific situation.
Late spring through early fall offers the best conditions. May through October typically provides dry weather and temperatures that allow roofing adhesives and sealants to cure properly. Asphalt shingles need temperatures above 40-45 degrees to seal correctly. The ideal window is often late spring (May-June) or early fall (September-October) when weather is stable but schedules aren't as packed as peak summer. For Wellesley homeowners planning a roof replacement on larger estate homes, booking well in advance is wise since these projects take longer to schedule. That said, roofing can happen year-round in Massachusetts. Winter installations are possible but have limitations. We can hand-seal shingles in colder weather, though snow and ice on the roof delay work. Winter projects sometimes cost more due to slower conditions and additional safety requirements. If your roof is actively leaking or showing serious damage, don't wait months for perfect weather. We can work around the conditions and protect your home.
Yes, we handle everything with Wellesley's Building Department. Roof replacements require a building permit. We submit applications through the town's ViewPoint Cloud online portal, pay permit fees, and schedule all required inspections. You don't need to visit 888 Worcester Street or coordinate with inspectors. That's all on us. The permit process typically adds several business days before we can start, depending on building department workload. For homes in Wellesley's historic districts, such as the Cottage Street Historic District, we also understand what the Historic District Commission expects for exterior work. Roofing materials in these areas may need to respect architectural character. Why permitting matters: unpermitted work creates problems. Your homeowner's insurance may not cover damage if work wasn't permitted. When you sell, unpermitted work shows up in inspections and can complicate the sale. Given Wellesley's property values, protecting your investment with properly permitted, code-compliant work is essential.
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 material warranties. Slate and copper products have their own warranty structures. These manufacturer warranties cover defects in the materials. Second, and often more important for quality-conscious Wellesley homeowners, is our workmanship warranty. About 90% of premature roof failures come from installation problems rather than defective materials. Poor flashing details around dormers and chimneys, inadequate ventilation, incorrect nailing patterns, improper valley installation. These are installation issues. Our written workmanship warranty covers issues resulting from how the roof was installed. As certified installers for major manufacturers, we can also offer enhanced warranties combining materials and labor coverage for extended periods. GAF's Golden Pledge, for example, covers both for up to 25 years. We'll explain all warranty options when providing your estimate.
The clearest signs are visible from the ground or your attic. From outside, look for missing shingles after storms, shingles that are curling or buckling, visible cracks, or dark streaks indicating algae growth. Check your gutters after rain. If you're finding granules collecting there (the sandpaper-like coating that washes off worn shingles), your roof is breaking down. From inside your attic, look for daylight through the roof deck, water stains on the underside of decking, or musty odors indicating moisture problems. Age is a major factor. Most asphalt roofs last 20-30 years. If yours is approaching that range and showing wear, start planning. Recurring ice dams in winter often indicate inadequate ventilation or insulation that proper roof replacement can address. For Wellesley's older colonials and estate homes, if the roof has never been replaced or you're unsure of its age, an inspection makes sense. Higher heating or cooling bills can mean your roof and attic system aren't insulating properly. We offer free inspections and will tell you honestly whether you need replacement now or can get more years with targeted repairs.

We Also Serve Nearby Communities

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