Home › Massachusetts › Winchester
Roofers in Winchester, MA
Large older home with a roof near the end of its life, or a leak to chase? Call (978) 577-5300 or send the form for a free estimate on Winchester roof repair or replacement. We'll review your request and help you with the next step.
- Free for homeowners
- Credentials checked before referral
- Rangeley to the Mystic Lakes
Get a Free Roofing Estimate
Tell us what's going on with the roof. We'll review it and help you with the next step.
Please add your name, a 10-digit phone number and a valid email.
Roofing services in Winchester
Need roofing work in Winchester?
Whether you've found a leak, noticed worn or missing shingles, or think it's time for a new roof, start with the service that matches your situation.
Roof Replacement
Tear-off, deck repair, ice and water barrier and a new roof, done to code.
Roof Repair & Leaks
Flashing, vent boots, missing shingles and leak tracing, plus inspections.
Flat & Rubber Roofs
EPDM, TPO and modified bitumen on low-slope roofs, porches and additions.
Ice Dams
Safe removal, plus the insulation and ventilation fixes that stop them.
Storm Damage
Tarping and repairs after wind, falling limbs, hail and heavy snow.
Winchester roofs, neighborhood by neighborhood
What's on the roofs in Winchester
Winchester owes its growth to the Boston & Lowell Railroad, which opened in 1835, and became a commuter suburb by the late 1800s. Trolleys arrived in the 1890s. Population reached about 10,000 by 1915 and 15,000 by 1940, and is about 23,000 today. The town's housing plan says single-family houses make up 78% of its roughly 8,000 homes. The housing stock is rich in Queen Anne, Shingle Style, Colonial Revival and Craftsman houses, followed by Colonial, Dutch and Tudor Revival homes in stucco and brick.


Winchester Center
Picturesque Victorian buildings surround the town center, a commuter rail stop and a National Register district.
Rangeley
Created in the 1870s by David Nelson Skillings on his Church Street estate as a park without public streets or fences. Its Queen Anne, Shingle, Italianate, Colonial Revival and mid-century modern houses form a heritage district.
Winchester Highlands
Development spread east along Highland Avenue toward the Middlesex Fells, with single-family revival-style homes.
Mystic Lakes
Single-family neighborhoods in Neo-Colonial styles grew up around the Mystic Lakes, which Winchester shares with Medford and Arlington.
Swanton and Main Streets
A workers' district remains along the valley rail corridor, reflecting the town's industrial past.
Winchester houses
Roofing Winchester's Victorian and revival-style homes
Queen Anne and Shingle Style houses. Towers, wide gables, eyebrow dormers and curved roof sections take skill. Every valley and wall joint needs proper flashing, and the estimate should spell it out.
Tudor, Dutch and Colonial Revival homes. Steep Tudor gables, gambrel Dutch Colonials and stucco or brick walls mean flashing has to tie into masonry. Large chimneys need new flashing and often repointing.
Slate and older materials. Some older Winchester houses may still have slate or other original roofing. Slate can often be repaired slate by slate; get a slate-experienced opinion before a tear-off.
Trees and winter. Where mature trees shade a roof, it stays damp longer and collects debris. See storm damage and ice dams.
Repair or replace? See roof repair and roof replacement.
Permits and historic review
Roofing permits in Winchester
Building permit. Winchester's Building Department takes all permit applications online. A permit is required to construct, alter or demolish a structure and must be posted at the job site. The fee is $18 per $1,000, with a $50 minimum. Construction is limited to 7 a.m.–6 p.m. weekdays and 9 a.m.–5 p.m. Saturdays, and isn't allowed on Sundays or holidays.
Rangeley Park Heritage District. Roof color and roofing that doesn't materially change the house's appearance are excluded from review. Changes to roof shape or slope, new dormers and prominent solar equipment are reviewed by the Heritage District Commission.
Historic review elsewhere. We found no local historic district under state law in Winchester. The town's National Register districts don't add a permit review, though the town has a bylaw that can delay demolition of historically significant buildings.
Licensing. We verify the credentials a job requires before we send a contractor any calls.
Roofing Service Pros is a referral service. We don't pull permits or do roofing work. The roofing contractor who does the job handles the permit.
FAQ
Winchester roofing questions
How do I get a roofing permit in Winchester?
Winchester's Building Department takes all permit applications online. The town says a building permit is required to construct, alter or demolish a structure, and the permit must be posted at the job site. The fee is $18 per $1,000, with a $50 minimum. The department links state HIC and CSL lookups and has a workers' comp form.
What hours can roofers work in Winchester?
Under the town's construction bylaw, work is allowed from 7 a.m. to 6 p.m. on weekdays and 9 a.m. to 5 p.m. on Saturdays, with no construction on Sundays or holidays. Factor that into your schedule.
I live in Rangeley. Does a new roof need approval?
Usually not. The Rangeley Park Heritage District bylaw excludes roof color and roofing materials that don't materially change the house's style or appearance, as well as ordinary maintenance and replacement. The Heritage District Commission does review changes to roof shape or slope, new dormers, and solar equipment on prominent façades.
Can I sign the homeowner exemption?
Only if you live in the house. Winchester's homeowner affidavit requires the owner to live on the premises to sign the exemption form, and you then take responsibility for the work.
Do homeowners pay to use Roofing Service Pros?
No. The call and the referral are free. Your price and contract are between you and the roofing contractor.
Nearby