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 qualified pros come to you.
50 contractors serving Pittsfield — including 10 based in town.
Contractors serving Pittsfield
- AWC Construction LLCBased in Pittsfield★★★★★5.0 rating
- Gutters & Siding, LLCBased in Pittsfield★★★★★5.0 rating
30 Spring St, Pittsfield, MA 01201
- East Coast RefinishingBased in Pittsfield★★★★★5.0 rating
4 Industrial Dr, Pittsfield, MA 01201
- JAF ContractingBased in Pittsfield★★★★★5.0 rating
346 Wahconah St, Pittsfield, MA 01201
- F&J Construction servicesBased in Pittsfield★★★★★4.8 rating
63 Edward Ave, Pittsfield, MA 01201
- Based in Pittsfield
169 Gale Ave, Pittsfield, MA 01201
- R & T Roofing and RemodelingBased in Pittsfield★★★★★4.8 rating
30 Putnam Ave, Pittsfield, MA 01201
- Thermo ExpertBased in Pittsfield★★★★★4.5 rating
1396 North St, Pittsfield, MA 01201
- Barile Environmental Inc.Based in Pittsfield★★★★★5.0 rating
78 Plastics Ave, Pittsfield, MA 01201
- East Coast Air BarrierBased in Pittsfield★★★★★5.0 rating
1591 East St a, Pittsfield, MA 01201
- J’s Dog Haus ShedsServes Pittsfield · 4.7 mi★★★★★5.0 rating
36 Pittsfield Rd, Lenox, MA 01240
- Morrison's Home ImprovementServes Pittsfield · 5.4 mi★★★★★4.5 rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- Berkshire General Contracting, LLCServes Pittsfield · 5.6 mi★★★★★5.0 rating
200 North St, Dalton, MA 01226
- Ryan Williams RoofingServes Pittsfield · 5.8 mi★★★★★5.0 rating
25 Judith Dr, Dalton, MA 01226
- Fairview RoofingServes Pittsfield · 10.9 mi★★★★☆4.3 rating
280 Fairview St, Lee, MA 01238
- Assis Home ImprovementServes Pittsfield · 11.1 mi★★★★★5.0 rating
28 Lana Ave, Lee, MA 01238
- Berkshire Roofing Co LLCServes Pittsfield · 12.4 mi★★★★★4.8 rating
2 Castle Hill Rd, Stockbridge, MA 01262
- J Kuhn CopperServes Pittsfield · 17.3 mi★★★★★5.0 rating
61 N Egremont Rd, Great Barrington, MA 01230
- Serves Pittsfield · 17.9 mi
70 State Rd, Great Barrington, MA 01230
- Greylock WORKSServes Pittsfield · 17.9 mi★★★★★4.7 rating
508 State Rd, North Adams, MA 01247
- SFB Construction LLCServes Pittsfield · 18.0 mi★★★★★5.0 rating
165 Cold Spring Rd, Williamstown, MA 01267
- PHE Attic Insulation & Roofing Services Co, MAServes Pittsfield · 29.9 mi★★★★★5.0 rating
44 Montgomery Rd, Southampton, MA 01073
- Andy's Custom Built ShedsServes Pittsfield · 32.4 mi★★★★★5.0 rating
233 Root Rd Unit 111, Westfield, MA 01085
- Stone Mountain Roofing LLCServes Pittsfield · 32.5 mi★★★★★5.0 rating
156 Northampton St, Easthampton, MA 01027
- Sexton Roofing & SidingServes Pittsfield · 32.5 mi★★★★★4.8 rating
6 Church Ave, West Hatfield, MA 01088
- GL FOUR STAR HOME IMPROVEMENT INCServes Pittsfield · 33.0 mi★★★★★5.0 rating
80 Damon Rd # 1, Northampton, MA 01060
- metrica Interior, Inc.Serves Pittsfield · 33.0 mi★★★★★5.0 rating
209 Earle St, Northampton, MA 01060
- Peak Performance Roofing LLCServes Pittsfield · 33.2 mi★★★★★4.9 rating
1 Lovefield St, Easthampton, MA 01027
- JP Carroll RoofingServes Pittsfield · 33.4 mi★★★★★4.9 rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Earthlight TechnologiesServes Pittsfield · 33.6 mi★★★★★5.0 rating
25 Main St #338, Northampton, MA 01060
- Quality Cleaning & Restoration, Inc.Serves Pittsfield · 33.7 mi★★★★★5.0 rating
355 Bridge St, Northampton, MA 01060
- Hometown Metal RoofingServes Pittsfield · 34.0 mi★★★★★5.0 rating
627 Southampton Rd, Westfield, MA 01085
- Morton Buildings, Inc.Serves Pittsfield · 34.0 mi★★★★★5.0 rating
563 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Pittsfield · 34.1 mi★★★★★5.0 rating
549 Southampton Rd, Westfield, MA 01085
- Tighe & BondServes Pittsfield · 34.5 mi★★★★☆4.4 rating
53 Southampton Rd, Westfield, MA 01085
- A-Z Exteriors, INCServes Pittsfield · 34.9 mi★★★★★5.0 rating
258 Hillside Rd, Southwick, MA 01077
- Supreme Seamless Gutters LLCServes Pittsfield · 34.9 mi★★★★★5.0 rating
109 White St, Westfield, MA 01085
- Hawkins RoofingServes Pittsfield · 35.4 mi★★★★★5.0 rating
89 Crescent St, Greenfield, MA 01301
- Keith G. Roy Construction, Inc.Serves Pittsfield · 35.9 mi★★★★☆4.3 rating
54 Mainline Dr, Westfield, MA 01085
- Major Home Improvements LLC - RoofingServes Pittsfield · 35.9 mi★★★★★5.0 rating
22 Verona St, Westfield, MA 01085
- 3D Home ImprovementsServes Pittsfield · 36.2 mi★★★★★5.0 rating
74 Old Holyoke Rd, Westfield, MA 01085
- Patrick Kelly Roofing & SidingServes Pittsfield · 37.3 mi★★★★★5.0 rating
12 Old Feeding Hills Rd, Westfield, MA 01085
- Fortini Construction and Remodeling INCServes Pittsfield · 37.3 mi★★★★★4.7 rating
138 Feeding Hills Rd, Westfield, MA 01085
- Mr GutterServes Pittsfield · 37.4 mi★★★★★4.8 rating
740 High St, Holyoke, MA 01040
- Lively Builders IncServes Pittsfield · 37.7 mi★★★★★4.9 rating
11 Hillside Rd, Montague, MA 01351
- Dicky Matos Roofing IncServes Pittsfield · 37.7 mi★★★★★4.8 rating
23 Hadley Mill Rd, Holyoke, MA 01040
- Integrity Development & ConstructionServes Pittsfield · 37.8 mi★★★★★5.0 rating
110 Pulpit Hill Rd, Amherst, MA 01002
- Alliance Home Improvement IncServes Pittsfield · 37.9 mi★★★★★4.8 rating
375 Chicopee St, Chicopee, MA 01013
- Serves Pittsfield · 38.1 mi
109 Bungalow St, Southwick, MA 01077
- Custom GuttersServes Pittsfield · 38.2 mi★★★★★5.0 rating
2385 Westfield St, West Springfield, MA 01089
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.
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.
