108 Summer St, Pittsfield, MA 01201
Roofing in Pittsfield, Massachusetts
Compare contractors serving Pittsfield, Berkshire County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Pittsfield — including 5 based in town.
Contractors serving Pittsfield
Claimed listings within 5 miles come first, then the rest by rating, then distance. Google ratings as of October 2026. How we list and rank contractors
- AWC Construction LLCBased in Pittsfield★★★★★5.0 Google rating
- JAF ContractingBased in Pittsfield★★★★★5.0 Google rating
346 Wahconah St, Pittsfield, MA 01201
- Berkshire General Contracting, LLCServes Pittsfield · 5.6 mi★★★★★5.0 Google rating
200 North St, Dalton, MA 01226
- Ryan Williams RoofingServes Pittsfield · 5.8 mi★★★★★5.0 Google rating
25 Judith Dr, Dalton, MA 01226
- Assis Home ImprovementServes Pittsfield · 11.1 mi★★★★★5.0 Google rating
28 Lana Ave, Lee, MA 01238
- J Kuhn CopperServes Pittsfield · 17.3 mi★★★★★5.0 Google rating
61 N Egremont Rd, Great Barrington, MA 01230
- SFB Construction LLCServes Pittsfield · 18.0 mi★★★★★5.0 Google rating
165 Cold Spring Rd, Williamstown, MA 01267
- PHE Attic Insulation & Roofing Services Co, MAServes Pittsfield · 29.9 mi★★★★★5.0 Google rating
44 Montgomery Rd, Southampton, MA 01073
- Stone Mountain Roofing LLCServes Pittsfield · 32.5 mi★★★★★5.0 Google rating
156 Northampton St, Easthampton, MA 01027
- GL FOUR STAR HOME IMPROVEMENT INCServes Pittsfield · 33.0 mi★★★★★5.0 Google rating
80 Damon Rd # 1, Northampton, MA 01060
- Hometown Metal RoofingServes Pittsfield · 34.0 mi★★★★★5.0 Google rating
627 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Pittsfield · 34.1 mi★★★★★5.0 Google rating
549 Southampton Rd, Westfield, MA 01085
- A-Z Exteriors, INCServes Pittsfield · 34.9 mi★★★★★5.0 Google rating
258 Hillside Rd, Southwick, MA 01077
- Hawkins RoofingServes Pittsfield · 35.4 mi★★★★★5.0 Google rating
89 Crescent St, Greenfield, MA 01301
- Major Home Improvements LLC - RoofingServes Pittsfield · 35.9 mi★★★★★5.0 Google rating
22 Verona St, Westfield, MA 01085
- 3D Home ImprovementsServes Pittsfield · 36.2 mi★★★★★5.0 Google rating
74 Old Holyoke Rd, Westfield, MA 01085
- Patrick Kelly Roofing & SidingServes Pittsfield · 37.3 mi★★★★★5.0 Google rating
12 Old Feeding Hills Rd, Westfield, MA 01085
- Peak Performance Roofing LLCServes Pittsfield · 33.2 mi★★★★★4.9 Google rating
1 Lovefield St, Easthampton, MA 01027
- JP Carroll RoofingServes Pittsfield · 33.4 mi★★★★★4.9 Google rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Lively Builders IncServes Pittsfield · 37.7 mi★★★★★4.9 Google rating
11 Hillside Rd, Montague, MA 01351
- F&J Construction servicesBased in Pittsfield★★★★★4.8 Google rating
63 Edward Ave, Pittsfield, MA 01201
- R & T Roofing and RemodelingBased in Pittsfield★★★★★4.8 Google rating
30 Putnam Ave, Pittsfield, MA 01201
- Berkshire Roofing Co LLCServes Pittsfield · 12.4 mi★★★★★4.8 Google rating
2 Castle Hill Rd, Stockbridge, MA 01262
- Sexton Roofing & SidingServes Pittsfield · 32.5 mi★★★★★4.8 Google rating
6 Church Ave, West Hatfield, MA 01088
- Fortini Construction and Remodeling INCServes Pittsfield · 37.3 mi★★★★★4.7 Google rating
138 Feeding Hills Rd, Westfield, MA 01085
- Morrison's Home ImprovementServes Pittsfield · 5.4 mi★★★★★4.5 Google rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- Fairview RoofingServes Pittsfield · 10.9 mi★★★★☆4.3 Google rating
280 Fairview St, Lee, MA 01238
- Keith G. Roy Construction, Inc.Serves Pittsfield · 35.9 mi★★★★☆4.3 Google rating
54 Mainline Dr, Westfield, MA 01085
- Based in Pittsfield
169 Gale Ave, Pittsfield, MA 01201
- Serves Pittsfield · 17.9 mi
70 State Rd, Great Barrington, MA 01230
Roofing in Pittsfield — what to know
Insurance & rebates
Two financial threads run through a Pittsfield re-roof. First, insurance. Berkshires carriers watch roof age and condition closely given the snow-load and ice-dam environment — an asphalt roof past 18-20 years commonly triggers non-renewal or a surcharge, and heavy snow events generate collapse- and ice-dam-related claims. Document storm and ice damage thoroughly before filing; a new, properly built roof typically earns a premium reduction.
On the energy side, Pittsfield is in Eversource territory, so Mass Save applies. Attic insulation and air-sealing are subsidized at 75% or higher for IOU customers — and older Berkshires housing tends to be heavily under-insulated, which is the root cause of the ice dams that damage roofs here. A re-roof is the cheapest moment to fix the attic with the deck open, and a free Mass Save Home Energy Assessment unlocks the incentives. Better insulation and ventilation directly extend roof life in this climate.
Permits in Pittsfield
Pittsfield requires a building permit for any roof replacement, filed through the Department of Inspection Services at City Hall. Massachusetts code requires an ice-and-water shield membrane at the eaves at least 24 inches inside the warm-wall line — and in Pittsfield's snow climate, many roofers extend that coverage well beyond the minimum given the severe ice-dam risk. Snow-load provisions in the state code also govern structural roof work. The state permits only one shingle overlay, so most roofers tear off to the deck. The Park Square and Wendell Avenue historic areas may need extra review for visible material changes on Victorian homes. Licensed contractors handle the filings.
Where a permit is required, roofing work in Pittsfield is filed with the Pittsfield Building Department; see the Pittsfield Building Department’s contact, portal and who pulls the permit on permits.llc.
Typical project cost
Pittsfield roofing prices run noticeably below Boston metro — Berkshires labor rates and density are both lower. A standard asphalt shingle re-roof on an Allendale or Coltsville post-war home typically runs $8,000-$16,000 depending on size and pitch; larger or steeper homes push toward $20,000. Slate restoration on a downtown Victorian is substantially higher — often $28,000-$55,000 — given material and skilled labor. Flat or low-slope EPDM rubber sections run $7,000-$14,000. Standing-seam metal runs $20,000-$42,000 and is a popular snow-shedding choice here. The catch is scheduling: the Berkshires roofer pool is smaller, so booking in spring or fall gets the cleanest lead times.
About Pittsfield homes
Pittsfield is the largest city in the Berkshires, with about 43,000 residents and a housing stock that traces the GE era — Victorian and Queen Anne homes downtown and along South Street, many with original slate or steep asphalt roofs, plus post-war single-families and ranches in Allendale and Coltsville that are almost all asphalt shingle. Median construction is around 1955.
What sets Pittsfield apart is climate. The city sits at the colder edge of Zone 5b with heavy seasonal snowfall, so snow load and ice-dam exposure shape roofing decisions more than anywhere in the eastern part of the state. Steep pitches shed snow better and are common on the older stock; flatter post-war and ranch roofs need careful attention to drainage, ice-and-water coverage, and ventilation to survive Berkshires winters.
Common questions — Roofing in Pittsfield
- Does heavy snow change how a Pittsfield roof should be built?
- Yes. Snow load and ice dams are the defining Berkshires roofing concern. Steep pitches shed snow well; flatter roofs need robust drainage and extended ice-and-water coverage. Many homeowners choose standing-seam metal specifically because it sheds snow and resists ice damming.
- Does Mass Save help reduce ice dams when I re-roof?
- Indirectly, yes — and it matters a lot here. Pittsfield is Eversource territory, so Mass Save subsidizes attic insulation and air-sealing at 75% or higher. Berkshires homes are often badly under-insulated, which causes the ice dams that damage roofs. Pair insulation work with the re-roof.
- Why does it take longer to schedule a roofer in Pittsfield?
- The Berkshires contractor pool is smaller than eastern Massachusetts and travel times within the county are longer. Booking non-emergency roofing in spring or fall usually gets the fastest response and the cleanest install window before winter.
- Should I extend ice-and-water shield beyond code in Pittsfield?
- Many local roofers recommend it. Code requires 24 inches past the warm wall, but Pittsfield's severe ice-dam exposure often justifies extending coverage further up the roof and into valleys. Discuss the snow climate with your contractor during the estimate.
- Do I need a permit to replace my roof in Pittsfield?
- Yes. The Department of Inspection Services requires a building permit for any roof replacement, and structural work is subject to snow-load provisions. Reputable roofers tear off to the deck and handle the permit as part of the job.
