140 Summer St Rear, Medway, MA 02053
Roofing in Medway, Massachusetts
Compare contractors serving Medway, Norfolk County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Medway — including 3 based in town.
Contractors serving Medway
- Prestige RoofingBased in Medway★★★★★4.9 rating
- Masters Touch Design BuildBased in Medway★★★★★4.7 rating
77 Main St, Medway, MA 02053
- Johnson Construction & RemodelingBased in Medway★★★★★4.5 rating
23 Holliston St, Medway, MA 02053
- CF Brothers RoofingServes Medway · 1.7 mi★★★★★5.0 rating
191 Hill St, Holliston, MA 01746
- Alfa Construction Inc.Serves Medway · 1.9 mi★★★★★5.0 rating
34 Pearl St, Bellingham, MA 02019
- MASTERPIECE ROOFING INCServes Medway · 2.5 mi★★★★★4.8 rating
1248 Highland St Unit 116, Holliston, MA 01746
- Fair Roofing & GuttersServes Medway · 2.8 mi★★★★☆3.7 rating
23 Water St #207, Holliston, MA 01746
- Eternal Pros Construction IncServes Medway · 3.6 mi★★★★★5.0 rating
40 Medway Rd, Milford, MA 01757
- Steven's General ConstructionServes Medway · 3.8 mi★★★★★5.0 rating
408 Washington St, Holliston, MA 01746
- The Roof InspectorServes Medway · 4.0 mi★★★★★5.0 rating
130 Cedar St Unit 6, Milford, MA 01757
- Colantonio IncServes Medway · 4.1 mi★★★★★4.9 rating
16 Everett St A, Holliston, MA 01746
- MN General ConstructionServes Medway · 4.1 mi★★★★★5.0 rating
39 Hayward St, Milford, MA 01757
- Handyman BrothersServes Medway · 4.1 mi★★★★★5.0 rating
27 Cedar St, Milford, MA 01757
- Regulus ConstructionServes Medway · 4.3 mi★★★★★4.9 rating
36 West St, Milford, MA 01757
- JP Creative MaintenanceServes Medway · 4.3 mi★★★★★5.0 rating
19 Stonehedge Rd, Bellingham, MA 02019
- Master RoofServes Medway · 4.3 mi★★★★★4.9 rating
2 Main St, Milford, MA 01757
- Tucker ConstructionServes Medway · 4.4 mi★★★★★5.0 rating
124 Grove St, Bellingham, MA 02019
- Usa Roofing inc.Serves Medway · 4.4 mi★★★★★5.0 rating
112 Grove St #1004, Bellingham, MA 02019
- LKS ConstructionServes Medway · 4.5 mi★★★★★5.0 rating
31 Granite St #3, Milford, MA 01757
- Serves Medway · 4.5 mi
41 Sumner St, Milford, MA 01757
- Total Guard Construction IncServes Medway · 4.5 mi★★★★★5.0 rating
40 Depot St, Milford, MA 01757
- Nova Top Roofing & SidingServes Medway · 4.6 mi★★★★★5.0 rating
51 Jefferson St #2, Milford, MA 01757
- SGE Solar - Second Generation EnergyServes Medway · 4.6 mi★★★★★4.6 rating
85 S Bow St #3376, Milford, MA 01757
- JGC Construction Inc.Serves Medway · 4.6 mi★★★★★5.0 rating
84 Depot St, Milford, MA 01757
- DGL Construction IncServes Medway · 4.6 mi★★★★★5.0 rating
89-91 School St, Milford, MA 01757
- Betho Construction IncServes Medway · 4.6 mi★★★★★5.0 rating
26 Jefferson St, Milford, MA 01757
- Huerta ConstructionServes Medway · 4.6 mi★★★★★5.0 rating
6 Purchase St, Milford, MA 01757
- New England ExteriorsServes Medway · 4.7 mi★★★★★5.0 rating
59 5th Ave, Bellingham, MA 02019
- Hendo Construction INCServes Medway · 4.7 mi★★★★★5.0 rating
49 Windsor Dr, Holliston, MA 01746
- Tiago Tiles ServicesServes Medway · 4.8 mi★★★★★5.0 rating
111 Depot St, Milford, MA 01757
- Serves Medway · 4.8 mi
3B Governors Way, Milford, MA 01757
- America Carpentry and Services IncServes Medway · 4.9 mi★★★★★5.0 rating
27 Congress St, Milford, MA 01757
- Same Day RoofingServes Medway · 4.9 mi★★★★★4.9 rating
38 Congress St, Milford, MA 01757
- AEGIS PRESTIGE LLCServes Medway · 4.9 mi★★★★★5.0 rating
105 Congress St, Milford, MA 01757
- Shaddai Home Improvement LLCServes Medway · 4.9 mi★★★★★5.0 rating
19 Rosenfeld Ave, Milford, MA 01757
- SPG Home Services incServes Medway · 4.9 mi★★★★★4.9 rating
6 Water St, Milford, MA 01757
- Mike's Roofing ConstructionServes Medway · 4.9 mi★★★★★5.0 rating
20 Church St, Milford, MA 01757
- Tyee Construction CorpServes Medway · 5.0 mi★★★★★5.0 rating
6-8 Otis St, Milford, MA 01757
- Services PlusServes Medway · 5.0 mi★★★★★4.8 rating
241 Kuniholm Dr bldg 3, Holliston, MA 01746
- Professional A Construction INCServes Medway · 5.2 mi★★★★★5.0 rating
62 Water St, Milford, MA 01757
- R F Arthur Home ImprovementServes Medway · 5.3 mi★★★★★4.9 rating
26 Longfellow Dr, Franklin, MA 02038
- GT Roofing CompanyServes Medway · 5.3 mi★★★★★5.0 rating
61 Water St, Milford, MA 01757
- Titan RestorationServes Medway · 5.4 mi★★★★★4.8 rating
40 Prospect St, Milford, MA 01757
- New Generation Custom HomesServes Medway · 5.4 mi★★★★★5.0 rating
40 Alpine Row, Franklin, MA 02038
- Affordable RoofingServes Medway · 5.4 mi★★★★★5.0 rating
33 Forge Hill Rd, Franklin, MA 02038
- LC General ConstructionServes Medway · 5.5 mi★★★★★4.7 rating
10 Allen Rd, Milford, MA 01757
- ACP Construction IncServes Medway · 5.7 mi★★★★★5.0 rating
3 Forest Path, Hopedale, MA 01747
- Chuma Construction IncServes Medway · 5.8 mi★★★★★5.0 rating
127 Jones Rd, Hopedale, MA 01747
- Hocol RoofingServes Medway · 6.0 mi★★★★★5.0 rating
3 Tanglewood Dr, Milford, MA 01757
- Outdoor PersoniaServes Medway · 6.2 mi★★★★★4.5 rating
1048 S Main St, Bellingham, MA 02019
Roofing in Medway — what to know
Insurance & rebates
Roofing isn't a Mass Save rebate item, but two factors drive the work in Medway. The first is inland snow load — winters here bring real accumulation, and ice dams forming at cold eaves are the leading cause of interior water damage on the town's mid-century colonials and capes, worsened where tree cover slows snowmelt. The second is insurance: carriers track roof age, and an asphalt roof past about 20 years often draws a surcharge or non-renewal. Document any storm, hail, or falling-limb damage before filing.
Medway is in Eversource territory, so the home qualifies for Mass Save weatherization. The roof isn't subsidized, but a tear-off is the cheapest moment to air-seal and insulate the attic — Mass Save covers that at 75% or more for Eversource customers, and it directly reduces the heat loss feeding ice dams.
Permits in Medway
Medway requires a building permit for roof replacement, filed through the Building Department at Town Hall. Massachusetts code requires an ice-and-water shield membrane at the eaves extending at least 24 inches past the warm-wall line — important given inland snow — plus valley and penetration protection. On Medway's 1960s-80s homes, tear-off can uncover soft sheathing at the eaves from past ice damming or tree-shaded moisture, and that deck repair is folded into the permitted scope. Licensed contractors pull the permit and schedule the inspection.
Typical project cost
Medway sits in the eastern Massachusetts/MetroWest cost band, modestly above the statewide average. A standard asphalt tear-off and re-roof on a typical colonial, cape, or raised ranch runs roughly $9,000-$18,000, with larger homes and steep multi-gable rooflines pushing toward $22,000. Switching from three-tab to architectural shingle adds modestly. Costs climb when tear-off uncovers deck rot at the eaves, or when a home carries multiple roof layers. Low-slope porch or addition sections in EPDM rubber are quoted separately.
About Medway homes
Medway is a Norfolk County town of about 13,200 residents across roughly 4,600 housing units, a suburban community on the Charles River near Franklin, Millis, and Holliston. The median home age is around 50 years, so much of the stock dates to the 1960s-80s suburban era — colonials, capes, garrisons, and raised ranches on wooded lots, with newer subdivisions on the edges, almost all on asphalt shingle.
With many of those roofs into their second covering, full tear-offs are the dominant project here. Medway's wooded suburban terrain and inland location mean real winter snowfall and tree-shaded eaves, both of which feed the ice damming common on the town's mid-century homes.
Common questions — Roofing in Medway
- Do I need a permit to re-roof in Medway?
- Yes. The Medway Building Department requires a permit for any roof replacement, with an inspection to follow. Licensed roofers handle the filing as part of the job.
- My mid-century home gets ice dams every winter — what's the fix?
- Ice dams form when heat escapes into the attic and melts snow that refreezes at the cold eave. The durable fix pairs a proper ice-and-water shield with attic air-sealing and insulation, which Eversource customers can subsidize through Mass Save.
- Will my insurer renew a 20-year-old roof?
- Many carriers now surcharge or decline to renew asphalt roofs past about 20 years, which fits many of Medway's mid-century homes. A new roof can preserve coverage and may lower your premium.
- Do the trees on my lot affect my roof?
- Yes. Medway's wooded lots shade roofs, slow snowmelt, and drop limbs and debris — all of which feed moisture damage and ice dams at the eaves. Keep limbs trimmed and gutters clear.
- Will tear-off uncover hidden damage?
- Sometimes, on 1960s-80s homes here. Stripping the old shingles can reveal soft or rotted deck sheathing at the eaves. Reputable contractors quote deck repair as a per-sheet add-on rather than a surprise.
