63 Chesterfield Rd, Williamsburg, MA 01096
Siding in Chester, Massachusetts
Compare contractors serving Chester, Hampden County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Chester.
Contractors serving Chester
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
- Guiel ConstructionServes Chester · 12.2 mi★★★★★5.0 Google rating
- Hometown Metal RoofingServes Chester · 13.1 mi★★★★★5.0 Google rating
627 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Chester · 13.2 mi★★★★★5.0 Google rating
549 Southampton Rd, Westfield, MA 01085
- Stone Mountain Roofing LLCServes Chester · 13.7 mi★★★★★5.0 Google rating
156 Northampton St, Easthampton, MA 01027
- A-Z Exteriors, INCServes Chester · 14.5 mi★★★★★5.0 Google rating
258 Hillside Rd, Southwick, MA 01077
- Major Home Improvements LLC - RoofingServes Chester · 15.1 mi★★★★★5.0 Google rating
22 Verona St, Westfield, MA 01085
- 3D Home ImprovementsServes Chester · 15.3 mi★★★★★5.0 Google rating
74 Old Holyoke Rd, Westfield, MA 01085
- Assis Home ImprovementServes Chester · 15.9 mi★★★★★5.0 Google rating
28 Lana Ave, Lee, MA 01238
- GL FOUR STAR HOME IMPROVEMENT INCServes Chester · 16.1 mi★★★★★5.0 Google rating
80 Damon Rd # 1, Northampton, MA 01060
- Patrick Kelly Roofing & SidingServes Chester · 16.5 mi★★★★★5.0 Google rating
12 Old Feeding Hills Rd, Westfield, MA 01085
- Mayers Enterprise LLCServes Chester · 16.7 mi★★★★★5.0 Google rating
427 Beech St, Holyoke, MA 01040
- A.R.K. BuildersServes Chester · 17.2 mi★★★★★5.0 Google rating
32 Marlene Dr, Feeding Hills, MA 01030
- Cedar Falls ConstructionServes Chester · 18.2 mi★★★★★5.0 Google rating
209 Prospect St, Chicopee, MA 01013
- Chamberland CedarServes Chester · 18.6 mi★★★★★5.0 Google rating
14 Exchange St, Chicopee, MA 01013
- JP Carroll RoofingServes Chester · 12.5 mi★★★★★4.9 Google rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Green CollarServes Chester · 17.9 mi★★★★★4.9 Google rating
48 Lamb St, South Hadley, MA 01075
- Nova VC ConstructionServes Chester · 18.6 mi★★★★★4.9 Google rating
591 Grattan St, Chicopee, MA 01020
- Sexton Roofing & SidingServes Chester · 16.9 mi★★★★★4.8 Google rating
6 Church Ave, West Hatfield, MA 01088
- Alliance Home Improvement IncServes Chester · 17.3 mi★★★★★4.8 Google rating
375 Chicopee St, Chicopee, MA 01013
- Dicky Matos Roofing IncServes Chester · 17.6 mi★★★★★4.8 Google rating
23 Hadley Mill Rd, Holyoke, MA 01040
- R & T Roofing and RemodelingServes Chester · 19.3 mi★★★★★4.8 Google rating
30 Putnam Ave, Pittsfield, MA 01201
- F&J Construction servicesServes Chester · 19.5 mi★★★★★4.8 Google rating
63 Edward Ave, Pittsfield, MA 01201
- Fortini Construction and Remodeling INCServes Chester · 16.4 mi★★★★★4.7 Google rating
138 Feeding Hills Rd, Westfield, MA 01085
- Berkshire Home Pros, IncServes Chester · 18.7 mi★★★★★4.7 Google rating
90 Flansburg Ave, Dalton, MA 01226
- Morrison's Home ImprovementServes Chester · 19.0 mi★★★★★4.5 Google rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- Keith G. Roy Construction, Inc.Serves Chester · 15.1 mi★★★★☆4.3 Google rating
54 Mainline Dr, Westfield, MA 01085
- Fairview RoofingServes Chester · 16.7 mi★★★★☆4.3 Google rating
280 Fairview St, Lee, MA 01238
- N. Riley Construction, Inc.Serves Chester · 18.5 mi★★★★☆4.1 Google rating
621 Grattan St, Chicopee, MA 01020
- The Axxion Company, LLCServes Chester · 17.2 mi★★★★☆4.0 Google rating
67 Suffolk St, Holyoke, MA 01040
- Serves Chester · 17.9 mi
109 Bungalow St, Southwick, MA 01077
Siding in Chester — what to know
Energy & rebates
Mass Save does **not** apply in Chester: electricity is provided by the Chester Municipal Light Plant and the town has no natural gas service, so Mass Save weatherization rebates, the heat-pump incentive and the 0% HEAT Loan are not available here. This is the single most important fact for any energy-related project in town.
The municipal utility runs its own efficiency program — typically narrower than Mass Save, with lower or different rebate amounts — so check directly with Chester MLP before assuming any specific subsidy. A re-side is still the cheapest moment to insulate cavities, air-seal, and lay a proper WRB; the work just won't be subsidized at Mass Save's 75%+ rate. Pay for the envelope work as part of the project anyway — the lifetime energy savings remain real.
Permits in Chester
Chester requires a building permit for residential re-siding through the town Building Department. The Westfield River and substantial Wild & Scenic state-forest abutters put a meaningful share of parcels inside Wetlands Protection Act buffer zones, and Conservation Commission review is common for streamside projects. With a 71-year median build, lead RRP applies to nearly every project, and asbestos-cement shingle is common on the mid-century stock and requires MassDEP-licensed abatement when confirmed — encapsulation is often the right call when the shingle is intact.
Where a permit is required, siding work in Chester is filed with the Chester Building Department; see the Chester Building Department’s contact, portal and who pulls the permit on permits.llc.
Typical project cost
Re-siding a typical Chester single-family runs roughly $9,500–$20,000 for vinyl, $12,000–$24,000 for insulated vinyl, and $16,000–$35,000 for fiber-cement. Hilltown labor rates run below the Springfield area and well below the Boston metro. Chester-specific cost drivers are long, steep driveways, hillside staging, MLP-territory billing for any electrical permits that might tag along, and the abatement work that the mid-century stock often forces.
About Chester homes
Chester is a Hampden County hill town of about 1,403 residents across roughly 689 housing units, on the Westfield River in the heart of the Berkshires' eastern ridges. The town has a small village along the river and the rail line, surrounded by steep state forest and dispersed rural homes.
The median home is around 71 years old, weighted to a mix of 19th- and early-20th-century houses in the village, mid-century capes and ranches on the older subdivided land, and a thinner layer of contemporary back-road builds. Pre-1978 stock dominates, which makes lead-safe handling part of nearly every project, and asbestos-cement shingle is widespread on mid-century houses.
Common questions — Siding in Chester
- Does Mass Save apply to insulation under new siding in Chester?
- No. Chester is served by the Chester Municipal Light Plant, not Eversource or National Grid, and has no natural gas service, so Mass Save's 75%+ weatherization rebates and the 0% HEAT Loan do not apply.
- Is there any rebate help I should ask about?
- Check directly with Chester MLP. Municipal utilities often run their own narrower efficiency programs with different rebate amounts and rules — what's available changes from year to year.
- Should I still insulate during the re-side if there's no rebate?
- Usually yes. Even without the Mass Save subsidy, dense-pack cellulose and a real air barrier added with the cladding off cost a fraction of doing them later, and the lifetime energy savings are real.
- Is asbestos siding common on Chester houses?
- On the mid-century capes and ranches, yes. Asbestos-cement shingle was widely used through the 1960s, and any suspect material should be sampled by a licensed inspector before demo.
- Do I need a permit to re-side in Chester?
- Yes. The Chester Building Department requires a permit, and a reputable contractor handles the paperwork and inspections.
