346 Wahconah St, Pittsfield, MA 01201
Siding in Cheshire, Massachusetts
Compare contractors serving Cheshire, Berkshire County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Cheshire.
Contractors serving Cheshire
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
- JAF ContractingServes Cheshire · 8.4 mi★★★★★5.0 Google rating
- Gutters & Siding, LLCServes Cheshire · 8.9 mi★★★★★5.0 Google rating
30 Spring St, Pittsfield, MA 01201
- AWC Construction LLCServes Cheshire · 9.4 mi★★★★★5.0 Google rating
108 Summer St, Pittsfield, MA 01201
- Broadwell Carpentry Inc.Serves Cheshire · 9.8 mi★★★★★5.0 Google rating
62 Stratton Rd, Williamstown, MA 01267
- SFB Construction LLCServes Cheshire · 10.7 mi★★★★★5.0 Google rating
165 Cold Spring Rd, Williamstown, MA 01267
- Burnham Custom Building and RemodelingServes Cheshire · 10.8 mi★★★★★5.0 Google rating
610 N Hoosac Rd, Williamstown, MA 01267
- Assis Home ImprovementServes Cheshire · 19.5 mi★★★★★5.0 Google rating
28 Lana Ave, Lee, MA 01238
- Guiel ConstructionServes Cheshire · 23.5 mi★★★★★5.0 Google rating
63 Chesterfield Rd, Williamsburg, MA 01096
- Yeoman Design BuildServes Cheshire · 27.1 mi★★★★★5.0 Google rating
123 Sandgully Rd N, South Deerfield, MA 01373
- d. hayward restorationServes Cheshire · 27.5 mi★★★★★5.0 Google rating
111 River St, Greenfield, MA 01301
- BRJ BuildersServes Cheshire · 28.0 mi★★★★★5.0 Google rating
30 Olive St, Greenfield, MA 01301
- GL FOUR STAR HOME IMPROVEMENT INCServes Cheshire · 30.6 mi★★★★★5.0 Google rating
80 Damon Rd # 1, Northampton, MA 01060
- Stone Mountain Roofing LLCServes Cheshire · 31.4 mi★★★★★5.0 Google rating
156 Northampton St, Easthampton, MA 01027
- Integrity Development & ConstructionServes Cheshire · 33.6 mi★★★★★5.0 Google rating
110 Pulpit Hill Rd, Amherst, MA 01002
- Lively Builders IncServes Cheshire · 30.9 mi★★★★★4.9 Google rating
11 Hillside Rd, Montague, MA 01351
- R & T Roofing and RemodelingServes Cheshire · 9.5 mi★★★★★4.8 Google rating
30 Putnam Ave, Pittsfield, MA 01201
- F&J Construction servicesServes Cheshire · 9.6 mi★★★★★4.8 Google rating
63 Edward Ave, Pittsfield, MA 01201
- Berkshire Roofing Co LLCServes Cheshire · 21.8 mi★★★★★4.8 Google rating
2 Castle Hill Rd, Stockbridge, MA 01262
- C&S Wood DesignServes Cheshire · 25.4 mi★★★★★4.8 Google rating
59 Division St, Great Barrington, MA 01230
- Sexton Roofing & SidingServes Cheshire · 29.5 mi★★★★★4.8 Google rating
6 Church Ave, West Hatfield, MA 01088
- Berkshire Home Pros, IncServes Cheshire · 6.3 mi★★★★★4.7 Google rating
90 Flansburg Ave, Dalton, MA 01226
- First Generation Construction LLCServes Cheshire · 28.0 mi★★★★★4.7 Google rating
324 Main St, Greenfield, MA 01301
- Larkin LTD Enterprises LLCServes Cheshire · 28.2 mi★★★★★4.7 Google rating
974 S Main St, Great Barrington, MA 01230
- Chagnon Building & Remodeling, LLCServes Cheshire · 32.9 mi★★★★★4.6 Google rating
91 Stockbridge St, Hadley, MA 01035
- Morrison's Home ImprovementServes Cheshire · 14.7 mi★★★★★4.5 Google rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- Fairview RoofingServes Cheshire · 19.5 mi★★★★☆4.3 Google rating
280 Fairview St, Lee, MA 01238
- Hawkins RoofingServes Cheshire · 29.9 mi★★★★☆4.0 Google rating
15 Sunrise Ave, Deerfield, MA 01342
- Serves Cheshire · 10.6 mi
116 Mohawk Trail, North Adams, MA 01247
- Serves Cheshire · 11.0 mi
169 Gale Ave, Pittsfield, MA 01201
- Serves Cheshire · 19.0 mi
13 Interlaken Rd, Stockbridge, MA 01262
Siding in Cheshire — what to know
Energy & rebates
Cheshire is served by National Grid, an investor-owned utility, so homeowners qualify for the full Mass Save program. The siding itself isn't rebated, but on the kind of mid-century cape or ranch that dominates Cheshire — often with minimal wall insulation — a re-side is the cheapest moment to fix the envelope.
Mass Save typically covers weatherization at 75% or more after a free Home Energy Assessment, and the 0% HEAT Loan can finance qualifying envelope work. Pairing the rebated air-sealing and insulation with new siding meaningfully reduces heating cost in a Berkshire winter, and on the converted reservoir cottages it's often the first time the walls have ever been properly insulated.
Permits in Cheshire
Cheshire requires a building permit for residential re-siding through the town Building Department, and a reputable contractor pulls it. Projects near Cheshire Reservoir or the Hoosic River may trigger Conservation Commission review under the Wetlands Protection Act, so confirm setbacks before staging materials. With a 62-year median build and a strong pre-1978 share, the federal lead RRP rule applies on most older homes, requiring a Lead-Safe Certified crew. Asbestos-cement shingle is common on this stock and, when confirmed by testing, must be removed under Massachusetts DEP abatement rules.
Where a permit is required, siding work in Cheshire is filed with the Cheshire Building Department; see the Cheshire Building Department’s contact, portal and who pulls the permit on permits.llc.
Typical project cost
Re-siding a typical Cheshire single-family runs roughly $10,000–$21,000 for standard vinyl, depending on size and stories. Insulated vinyl with foam backing generally lands around $13,000–$26,000. Fiber-cement such as James Hardie runs about $16,000–$36,000, with cedar above that on the older farmhouses. Berkshire labor rates run below eastern Massachusetts, keeping base quotes lower. The bigger swing in Cheshire is what's hiding under the old cladding — asbestos-cement, lead paint, and the occasional rotted balloon-framed wall on the older homes all push real-world costs up.
About Cheshire homes
Cheshire is a small Berkshire County town between Adams and Lanesborough in the Hoosic River valley, with about 3,239 residents across roughly 1,698 housing units. The Ashuwillticook Rail Trail runs the length of town along the old rail bed, and Cheshire Reservoir anchors the south end.
The median home is around 62 years old, with the housing mix including 19th-century farmhouses near the village, mid-20th-century ranches and capes spreading from the village center, and lake-edge homes around the reservoir that started as cottages. A lot of the original aluminum and asbestos-cement shingle from the postwar build is being replaced now, and the Hoosic valley's tougher Berkshire winters age cladding faster than rates near the coast.
Common questions — Siding in Cheshire
- Could my Cheshire home have asbestos siding?
- Possibly. Asbestos-cement shingle was a common re-clad on Berkshire mid-century stock. Testing before tear-off is wise; if confirmed, removal must follow Massachusetts DEP abatement rules.
- Does Mass Save apply to insulation under new siding in Cheshire?
- Yes. Cheshire is National Grid territory, so homeowners qualify for Mass Save. The siding itself isn't rebated, but insulation and air-sealing behind it can be subsidized at 75%+ after a free Home Energy Assessment.
- My Cheshire reservoir cottage was built for summer — is re-siding the right time to fix that?
- Often yes. With the cladding off, you can air-seal, insulate the walls properly, and address the rim joist — Mass Save subsidizes most of that work, and it's much cheaper than doing it later from inside finished rooms.
- Is lead paint a concern when re-siding in Cheshire?
- On the older stock, yes. Any pre-1978 home needs a Lead-Safe Certified (RRP) crew when old painted wood is disturbed, and Cheshire has a meaningful share of pre-1978 homes.
- Do I need a permit to re-side my house in Cheshire?
- Yes. The Cheshire Building Department requires a permit for re-siding, and reputable contractors handle the paperwork and inspection as part of the project.
