90 Flansburg Ave, Dalton, MA 01226
Siding in Cheshire, Massachusetts
Compare contractors serving Cheshire, Berkshire County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Cheshire.
Contractors serving Cheshire
- Berkshire Home Pros, IncServes Cheshire · 6.3 mi★★★★★4.7 rating
- Thermo ExpertServes Cheshire · 7.5 mi★★★★★4.5 rating
1396 North St, Pittsfield, MA 01201
- JAF ContractingServes Cheshire · 8.4 mi★★★★★5.0 rating
346 Wahconah St, Pittsfield, MA 01201
- Gutters & Siding, LLCServes Cheshire · 8.9 mi★★★★★5.0 rating
30 Spring St, Pittsfield, MA 01201
- AWC Construction LLCServes Cheshire · 9.4 mi★★★★★5.0 rating
108 Summer St, Pittsfield, MA 01201
- R & T Roofing and RemodelingServes Cheshire · 9.5 mi★★★★★4.8 rating
30 Putnam Ave, Pittsfield, MA 01201
- F&J Construction servicesServes Cheshire · 9.6 mi★★★★★4.8 rating
63 Edward Ave, Pittsfield, MA 01201
- Broadwell Carpentry Inc.Serves Cheshire · 9.8 mi★★★★★5.0 rating
62 Stratton Rd, Williamstown, MA 01267
- Serves Cheshire · 10.6 mi
116 Mohawk Trail, North Adams, MA 01247
- SFB Construction LLCServes Cheshire · 10.7 mi★★★★★5.0 rating
165 Cold Spring Rd, Williamstown, MA 01267
- rk MILESServes Cheshire · 10.8 mi★★★★☆4.3 rating
385 Cole Ave, Williamstown, MA 01267
- Burnham Custom Building and RemodelingServes Cheshire · 10.8 mi★★★★★5.0 rating
610 N Hoosac Rd, Williamstown, MA 01267
- Serves Cheshire · 11.0 mi
169 Gale Ave, Pittsfield, MA 01201
- Morrison's Home ImprovementServes Cheshire · 14.7 mi★★★★★4.5 rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- Serves Cheshire · 19.0 mi
13 Interlaken Rd, Stockbridge, MA 01262
- Assis Home ImprovementServes Cheshire · 19.5 mi★★★★★5.0 rating
28 Lana Ave, Lee, MA 01238
- Fairview RoofingServes Cheshire · 19.5 mi★★★★☆4.3 rating
280 Fairview St, Lee, MA 01238
- Berkshire Roofing Co LLCServes Cheshire · 21.8 mi★★★★★4.8 rating
2 Castle Hill Rd, Stockbridge, MA 01262
- Guiel ConstructionServes Cheshire · 23.5 mi★★★★★5.0 rating
63 Chesterfield Rd, Williamsburg, MA 01096
- C&S Wood DesignServes Cheshire · 25.4 mi★★★★★4.8 rating
59 Division St, Great Barrington, MA 01230
- Yeoman Design BuildServes Cheshire · 27.1 mi★★★★★5.0 rating
123 Sandgully Rd N, South Deerfield, MA 01373
- Galvez Bros Painting LLCServes Cheshire · 27.2 mi★★★★★5.0 rating
124 Laurel St, Greenfield, MA 01301
- d. hayward restorationServes Cheshire · 27.5 mi★★★★★5.0 rating
111 River St, Greenfield, MA 01301
- First Generation Construction LLCServes Cheshire · 28.0 mi★★★★★4.7 rating
324 Main St, Greenfield, MA 01301
- BRJ BuildersServes Cheshire · 28.0 mi★★★★★5.0 rating
30 Olive St, Greenfield, MA 01301
- Eli PaintingServes Cheshire · 28.1 mi★★★★★4.8 rating
199 Deerfield St, Greenfield, MA 01301
- Larkin LTD Enterprises LLCServes Cheshire · 28.2 mi★★★★★4.7 rating
974 S Main St, Great Barrington, MA 01230
- Dunn Rite Handyman Services LLCServes Cheshire · 28.9 mi★★★★★4.8 rating
264 Long Plain Rd, South Deerfield, MA 01373
- Serves Cheshire · 29.1 mi
348 High St, Greenfield, MA 01301
- Sexton Roofing & SidingServes Cheshire · 29.5 mi★★★★★4.8 rating
6 Church Ave, West Hatfield, MA 01088
- Hawkins RoofingServes Cheshire · 29.9 mi★★★★☆4.0 rating
15 Sunrise Ave, Deerfield, MA 01342
- GL FOUR STAR HOME IMPROVEMENT INCServes Cheshire · 30.6 mi★★★★★5.0 rating
80 Damon Rd # 1, Northampton, MA 01060
- Lively Builders IncServes Cheshire · 30.9 mi★★★★★4.9 rating
11 Hillside Rd, Montague, MA 01351
- Stone Mountain Roofing LLCServes Cheshire · 31.4 mi★★★★★5.0 rating
156 Northampton St, Easthampton, MA 01027
- Chagnon Building & Remodeling, LLCServes Cheshire · 32.9 mi★★★★★4.6 rating
91 Stockbridge St, Hadley, MA 01035
- Cowls Building SupplyServes Cheshire · 33.2 mi★★★★★4.6 rating
125 Sunderland Rd, Amherst, MA 01059
- Window Works, LLCServes Cheshire · 33.5 mi★★★★★4.8 rating
321 Russell St, Hadley, MA 01035
- Integrity Development & ConstructionServes Cheshire · 33.6 mi★★★★★5.0 rating
110 Pulpit Hill Rd, Amherst, MA 01002
- Northeastern Log HomesServes Cheshire · 34.1 mi★★★★☆4.4 rating
1126 Southampton Rd, Westfield, MA 01085
- Serves Cheshire · 34.4 mi
115 Market Hill Rd, Amherst, MA 01002
- Cameron Painting Inc / Established 1988Serves Cheshire · 34.9 mi★★★★★4.5 rating
22 Whippletree Ln, Amherst, MA 01002
- JP Carroll RoofingServes Cheshire · 35.1 mi★★★★★4.9 rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Hometown Metal RoofingServes Cheshire · 35.3 mi★★★★★5.0 rating
627 Southampton Rd, Westfield, MA 01085
- Morton Buildings, Inc.Serves Cheshire · 35.4 mi★★★★★5.0 rating
563 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Cheshire · 35.5 mi★★★★★5.0 rating
549 Southampton Rd, Westfield, MA 01085
- Etinde PaintingServes Cheshire · 35.8 mi★★★★☆3.7 rating
730 West St, Amherst, MA 01002
- Mayers Enterprise LLCServes Cheshire · 36.8 mi★★★★★5.0 rating
427 Beech St, Holyoke, MA 01040
- The Axxion Company, LLCServes Cheshire · 37.1 mi★★★★☆4.0 rating
67 Suffolk St, Holyoke, MA 01040
- Green CollarServes Cheshire · 37.2 mi★★★★★4.9 rating
48 Lamb St, South Hadley, MA 01075
- Dicky Matos Roofing IncServes Cheshire · 37.2 mi★★★★★4.8 rating
23 Hadley Mill Rd, Holyoke, MA 01040
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.
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.
