70 State Rd, Great Barrington, MA 01230
Roofing in Monterey, Massachusetts
Compare contractors serving Monterey, Berkshire County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Monterey.
Contractors serving Monterey
- Serves Monterey · 6.8 mi
- Assis Home ImprovementServes Monterey · 7.3 mi★★★★★5.0 rating
28 Lana Ave, Lee, MA 01238
- Fairview RoofingServes Monterey · 7.6 mi★★★★☆4.3 rating
280 Fairview St, Lee, MA 01238
- Berkshire Roofing Co LLCServes Monterey · 9.0 mi★★★★★4.8 rating
2 Castle Hill Rd, Stockbridge, MA 01262
- J Kuhn CopperServes Monterey · 10.5 mi★★★★★5.0 rating
61 N Egremont Rd, Great Barrington, MA 01230
- Morrison's Home ImprovementServes Monterey · 13.3 mi★★★★★4.5 rating
25 Pittsfield Road Rt. 7 & 20, 25 Veterans Memorial Hwy, Lenox, MA 01240
- J’s Dog Haus ShedsServes Monterey · 13.9 mi★★★★★5.0 rating
36 Pittsfield Rd, Lenox, MA 01240
- East Coast RefinishingServes Monterey · 17.2 mi★★★★★5.0 rating
4 Industrial Dr, Pittsfield, MA 01201
- F&J Construction servicesServes Monterey · 17.6 mi★★★★★4.8 rating
63 Edward Ave, Pittsfield, MA 01201
- R & T Roofing and RemodelingServes Monterey · 17.6 mi★★★★★4.8 rating
30 Putnam Ave, Pittsfield, MA 01201
- Serves Monterey · 18.0 mi
169 Gale Ave, Pittsfield, MA 01201
- AWC Construction LLCServes Monterey · 18.4 mi★★★★★5.0 rating
108 Summer St, Pittsfield, MA 01201
- East Coast Air BarrierServes Monterey · 18.5 mi★★★★★5.0 rating
1591 East St a, Pittsfield, MA 01201
- Gutters & Siding, LLCServes Monterey · 18.6 mi★★★★★5.0 rating
30 Spring St, Pittsfield, MA 01201
- Barile Environmental Inc.Serves Monterey · 19.0 mi★★★★★5.0 rating
78 Plastics Ave, Pittsfield, MA 01201
- JAF ContractingServes Monterey · 19.5 mi★★★★★5.0 rating
346 Wahconah St, Pittsfield, MA 01201
- Ryan Williams RoofingServes Monterey · 19.8 mi★★★★★5.0 rating
25 Judith Dr, Dalton, MA 01226
- Berkshire General Contracting, LLCServes Monterey · 20.5 mi★★★★★5.0 rating
200 North St, Dalton, MA 01226
- Thermo ExpertServes Monterey · 20.5 mi★★★★★4.5 rating
1396 North St, Pittsfield, MA 01201
- PHE Attic Insulation & Roofing Services Co, MAServes Monterey · 22.8 mi★★★★★5.0 rating
44 Montgomery Rd, Southampton, MA 01073
- A-Z Exteriors, INCServes Monterey · 23.6 mi★★★★★5.0 rating
258 Hillside Rd, Southwick, MA 01077
- Andy's Custom Built ShedsServes Monterey · 24.4 mi★★★★★5.0 rating
233 Root Rd Unit 111, Westfield, MA 01085
- JP Carroll RoofingServes Monterey · 24.6 mi★★★★★4.9 rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Supreme Seamless Gutters LLCServes Monterey · 25.1 mi★★★★★5.0 rating
109 White St, Westfield, MA 01085
- Tighe & BondServes Monterey · 25.4 mi★★★★☆4.4 rating
53 Southampton Rd, Westfield, MA 01085
- Hometown Metal RoofingServes Monterey · 25.6 mi★★★★★5.0 rating
627 Southampton Rd, Westfield, MA 01085
- Morton Buildings, Inc.Serves Monterey · 25.6 mi★★★★★5.0 rating
563 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Monterey · 25.6 mi★★★★★5.0 rating
549 Southampton Rd, Westfield, MA 01085
- Serves Monterey · 25.8 mi
109 Bungalow St, Southwick, MA 01077
- Keith G. Roy Construction, Inc.Serves Monterey · 25.8 mi★★★★☆4.3 rating
54 Mainline Dr, Westfield, MA 01085
- Major Home Improvements LLC - RoofingServes Monterey · 25.9 mi★★★★★5.0 rating
22 Verona St, Westfield, MA 01085
- Patrick Kelly Roofing & SidingServes Monterey · 27.0 mi★★★★★5.0 rating
12 Old Feeding Hills Rd, Westfield, MA 01085
- Fortini Construction and Remodeling INCServes Monterey · 27.2 mi★★★★★4.7 rating
138 Feeding Hills Rd, Westfield, MA 01085
- 3D Home ImprovementsServes Monterey · 27.4 mi★★★★★5.0 rating
74 Old Holyoke Rd, Westfield, MA 01085
- Custom GuttersServes Monterey · 28.4 mi★★★★★5.0 rating
2385 Westfield St, West Springfield, MA 01089
- Stone Mountain Roofing LLCServes Monterey · 29.2 mi★★★★★5.0 rating
156 Northampton St, Easthampton, MA 01027
- Peak Performance Roofing LLCServes Monterey · 29.9 mi★★★★★4.9 rating
1 Lovefield St, Easthampton, MA 01027
- Nova Home ImprovementsServes Monterey · 30.2 mi★★★★★4.9 rating
764 Springfield St, Feeding Hills, MA 01030
- Mahan Slate Roofing Co.Serves Monterey · 30.8 mi★★★★☆4.2 rating
699 Silver St, Agawam, MA 01001
- Alliance Home Improvement IncServes Monterey · 30.8 mi★★★★★4.8 rating
375 Chicopee St, Chicopee, MA 01013
- metrica Interior, Inc.Serves Monterey · 30.9 mi★★★★★5.0 rating
209 Earle St, Northampton, MA 01060
- Rapid Quality Construction LLCServes Monterey · 30.9 mi★★★★★5.0 rating
1129 Riverdale St #1016, West Springfield, MA 01089
- Mr GutterServes Monterey · 31.2 mi★★★★★4.8 rating
740 High St, Holyoke, MA 01040
- Yost Manufacturing & SupplyServes Monterey · 31.6 mi★★★★★5.0 rating
86 Norman St, West Springfield, MA 01089
- Homepro Handyman Services Inc. HomePro Of Pioneer ValleyServes Monterey · 31.6 mi★★★★★4.7 rating
178 Center St, Chicopee, MA 01013
- Empire Metal RoofingServes Monterey · 31.7 mi★★★★★5.0 rating
58 Fairview Ave, West Springfield, MA 01089
- Earthlight TechnologiesServes Monterey · 31.8 mi★★★★★5.0 rating
25 Main St #338, Northampton, MA 01060
- LA Roofing LLCServes Monterey · 31.8 mi★★★★☆4.3 rating
36 Windsor St, West Springfield, MA 01089
- Dicky Matos Roofing IncServes Monterey · 32.0 mi★★★★★4.8 rating
23 Hadley Mill Rd, Holyoke, MA 01040
- GL FOUR STAR HOME IMPROVEMENT INCServes Monterey · 32.0 mi★★★★★5.0 rating
80 Damon Rd # 1, Northampton, MA 01060
Roofing in Monterey — what to know
Insurance & rebates
Monterey's roofing risk is south Berkshire snow load and ice dams, not coastal wind. Elevation, lake-effect snow off Lake Garfield, and shaded woodland exposures drive deep, persistent snowpack and chronic ice dams on broad eaves and porch transitions, where most local leaks originate. Insurance carriers in the south Berkshires routinely decline to renew on roofs past about 20 years; second-home roofs that go uninspected for months get caught by this often.
National Grid is the electric utility, so Mass Save applies. Mass Save never pays for a roof, but attic insulation and air-sealing — often thin or original-spec on the converted lake cottages — are typically subsidized at 75% or more after a free Home Energy Assessment.
Permits in Monterey
Monterey requires a building permit for roof replacement through the town Building Department, and Massachusetts code requires ice-and-water shield at the eaves and valleys. Properties around Lake Garfield, Lake Buel, and the smaller ponds frequently trigger Conservation Commission review under the Wetlands Protection Act for any associated structural work — common in a town where so much of the housing stock is lake-adjacent. Permit turnaround typically runs a few business days.
Typical project cost
Roofing in Monterey runs at the lower-to-mid end of the Massachusetts band, in line with the rest of the south Berkshires. A full asphalt tear-off typically runs $7,500–$20,000 depending on roof size, pitch, and access; flat or low-slope EPDM rubber on porch and lakeside sections runs $6,000–$14,000; standing-seam metal $17,000–$38,000. Lake-house geometry with multiple dormers, skylights, and porch transitions pushes asphalt toward the high end.
About Monterey homes
Monterey is a south Berkshire town of about 983 year-round residents but roughly 923 housing units — close to one-to-one, with a heavy seasonal-home share around Lake Garfield. The median home age is around 52 years, with stock weighted toward 1960s–1990s lake cottages and contemporaries on the water, plus an older village center along Route 23 and back-road farmhouses in the hills toward Tyringham and New Marlborough.
That lake-and-hilltown mix defines the roofing work. A high share of Monterey homes are steep, complex contemporaries with multiple roof planes, dormers, skylights, and low-slope porch sections facing Lake Garfield or Lake Buel — exactly the geometry where ice-dam and flashing leaks start. Many seasonal homes go uninspected for months between owner visits.
Common questions — Roofing in Monterey
- My house is on Lake Garfield — do I need wetlands review for a re-roof?
- A simple tear-off and reinstall typically does not. Anything structural — adding a dormer, expanding eaves, replacing a porch deck below the roof — within the buffer zone usually triggers Conservation Commission review under the Wetlands Protection Act.
- Does Mass Save help with my Monterey roof?
- No — Mass Save never funds roofing. Monterey is National Grid territory, though, so attic insulation and air-sealing are typically subsidized at 75% or more after a free assessment, and that work is the real defense against the ice dams driving most local damage.
- Do I need a permit to replace my roof in Monterey?
- Yes. The Monterey Building Department issues the permit, and state code requires ice-and-water shield at eaves and valleys. Lake- and pond-adjacent properties may also need Conservation Commission sign-off for any associated structural work.
- I own a Monterey second home — what's the right inspection cadence?
- Annual inspection after the late-winter thaw and another after any named storm. Most catastrophic south-Berkshire second-home losses start as small ice-dam leaks that go undetected for months and rot sheathing before the owner returns.
- Is standing-seam metal worth the cost on a Monterey lake house?
- On steep, complex roofs with chronic ice-dam history, often yes. Metal sheds snow cleanly and lasts 50-plus years versus 20–25 for architectural asphalt; cost is roughly $17,000–$38,000 versus $7,500–$20,000.
