30 Spring St, Pittsfield, MA 01201
Siding in Windsor, Massachusetts
Compare contractors serving Windsor, Berkshire County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Windsor.
Contractors serving Windsor
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
- Gutters & Siding, LLCServes Windsor · 10.8 mi★★★★★5.0 Google rating
- JAF ContractingServes Windsor · 10.8 mi★★★★★5.0 Google rating
346 Wahconah St, Pittsfield, MA 01201
- AWC Construction LLCServes Windsor · 11.5 mi★★★★★5.0 Google rating
108 Summer St, Pittsfield, MA 01201
- Broadwell Carpentry Inc.Serves Windsor · 14.6 mi★★★★★5.0 Google rating
62 Stratton Rd, Williamstown, MA 01267
- Burnham Custom Building and RemodelingServes Windsor · 15.5 mi★★★★★5.0 Google rating
610 N Hoosac Rd, Williamstown, MA 01267
- SFB Construction LLCServes Windsor · 15.8 mi★★★★★5.0 Google rating
165 Cold Spring Rd, Williamstown, MA 01267
- Guiel ConstructionServes Windsor · 17.5 mi★★★★★5.0 Google rating
63 Chesterfield Rd, Williamsburg, MA 01096
- Assis Home ImprovementServes Windsor · 18.6 mi★★★★★5.0 Google rating
28 Lana Ave, Lee, MA 01238
- Yeoman Design BuildServes Windsor · 21.7 mi★★★★★5.0 Google rating
123 Sandgully Rd N, South Deerfield, MA 01373
- d. hayward restorationServes Windsor · 22.8 mi★★★★★5.0 Google rating
111 River St, Greenfield, MA 01301
- BRJ BuildersServes Windsor · 23.4 mi★★★★★5.0 Google rating
30 Olive St, Greenfield, MA 01301
- GL FOUR STAR HOME IMPROVEMENT INCServes Windsor · 24.7 mi★★★★★5.0 Google rating
80 Damon Rd # 1, Northampton, MA 01060
- Stone Mountain Roofing LLCServes Windsor · 25.5 mi★★★★★5.0 Google rating
156 Northampton St, Easthampton, MA 01027
- Integrity Development & ConstructionServes Windsor · 27.9 mi★★★★★5.0 Google rating
110 Pulpit Hill Rd, Amherst, MA 01002
- Lively Builders IncServes Windsor · 26.2 mi★★★★★4.9 Google rating
11 Hillside Rd, Montague, MA 01351
- R & T Roofing and RemodelingServes Windsor · 10.7 mi★★★★★4.8 Google rating
30 Putnam Ave, Pittsfield, MA 01201
- F&J Construction servicesServes Windsor · 11.0 mi★★★★★4.8 Google rating
63 Edward Ave, Pittsfield, MA 01201
- Berkshire Roofing Co LLCServes Windsor · 22.1 mi★★★★★4.8 Google rating
2 Castle Hill Rd, Stockbridge, MA 01262
- Sexton Roofing & SidingServes Windsor · 23.6 mi★★★★★4.8 Google rating
6 Church Ave, West Hatfield, MA 01088
- C&S Wood DesignServes Windsor · 25.4 mi★★★★★4.8 Google rating
59 Division St, Great Barrington, MA 01230
- Berkshire Home Pros, IncServes Windsor · 7.0 mi★★★★★4.7 Google rating
90 Flansburg Ave, Dalton, MA 01226
- First Generation Construction LLCServes Windsor · 23.4 mi★★★★★4.7 Google rating
324 Main St, Greenfield, MA 01301
- Larkin LTD Enterprises LLCServes Windsor · 27.9 mi★★★★★4.7 Google rating
974 S Main St, Great Barrington, MA 01230
- Chagnon Building & Remodeling, LLCServes Windsor · 27.0 mi★★★★★4.6 Google rating
91 Stockbridge St, Hadley, MA 01035
- Morrison's Home ImprovementServes Windsor · 15.3 mi★★★★★4.5 Google rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- Fairview RoofingServes Windsor · 18.8 mi★★★★☆4.3 Google rating
280 Fairview St, Lee, MA 01238
- Hawkins RoofingServes Windsor · 24.6 mi★★★★☆4.0 Google rating
15 Sunrise Ave, Deerfield, MA 01342
- Serves Windsor · 12.1 mi
116 Mohawk Trail, North Adams, MA 01247
- Serves Windsor · 13.3 mi
169 Gale Ave, Pittsfield, MA 01201
- Serves Windsor · 19.4 mi
13 Interlaken Rd, Stockbridge, MA 01262
Siding in Windsor — what to know
Energy & rebates
Windsor is served by Eversource, so homeowners are fully Mass Save eligible. The cladding itself isn't rebated, but on a Windsor house, a re-side is the cheapest moment by a wide margin to add cavity insulation, air-seal aggressively, and lay continuous exterior insulation that the original wall almost certainly didn't have.
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. At Windsor's elevation, heating loads are higher than almost anywhere else in the state, and the rebated envelope work behind new siding usually delivers more comfort and bill improvement than any single other upgrade.
Permits in Windsor
Windsor requires a building permit for residential re-siding through the town Building Department. The Westfield River headwaters, Notchview, and the Windsor State Forest abutters put many parcels inside Wetlands Protection Act buffer zones, and Conservation Commission review is common for streamside work. With a 54-year median build, lead RRP applies to a meaningful share of stock, and asbestos-cement shingle still turns up on mid-century capes and ranches and requires MassDEP-licensed abatement when confirmed.
Where a permit is required, siding work in Windsor is filed with the Windsor Building Department; see the Windsor Building Department’s contact, portal and who pulls the permit on permits.llc.
Typical project cost
Re-siding a typical Windsor single-family runs roughly $10,500–$22,000 for vinyl, $13,000–$26,000 for insulated vinyl, and $17,000–$38,000 for fiber-cement. Berkshire hilltown labor sits well below eastern Massachusetts. Windsor-specific drivers are real: long, often-icy driveways, the heavier fastener and flashing spec for the elevation, an aggressively short working season (snow comes early and leaves late), and the abatement work the older stock sometimes forces.
About Windsor homes
Windsor is a Berkshire County hill town of about 1,030 residents across roughly 544 housing units, on the high plateau between Dalton and Cummington. Much of Windsor sits at elevations above 1,800 feet, including some of the highest sustained inhabited terrain in the state, and Windsor State Forest and Notchview Reservation cover a large share of the town.
The median home is around 54 years old, with a stock that runs from older farmhouses along the original roads to 1960s–80s rural ranches and capes, to a thinner layer of newer back-road customs. The defining variable here is elevation: winters are longer, ice loading is heavier, and wind exposure on the upper sites is brutal compared to the river valleys a few miles east.
Common questions — Siding in Windsor
- Does Mass Save cover insulation behind new siding in Windsor?
- Yes. Windsor is Eversource territory, so homeowners qualify for the full Mass Save program. The siding isn't rebated, but cavity insulation and air-sealing behind it are typically subsidized at 75%+ after a free Home Energy Assessment — and at Windsor's elevation, the payback is among the strongest in the state.
- What siding holds up at 1,800-plus feet?
- Fiber-cement and high-grade insulated vinyl both handle the wind and ice loading well. Detail the fasteners, flashing, and house wrap as carefully as the panel choice — the assembly behind the cladding has to do most of the work at altitude.
- How does Windsor's short season affect scheduling?
- Practically, the productive siding window is shorter than the valley. Contractors often book Windsor work tight against weather, and starting in early fall risks getting caught by snow. Plan around it and consider June–early September if possible.
- Is asbestos common on Windsor 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 Windsor?
- Yes. The Windsor Building Department requires a permit, and a reputable contractor handles the paperwork and inspections.
