1248 Highland St Unit 116, Holliston, MA 01746
Roofing in Holliston, Massachusetts
Compare contractors serving Holliston, Middlesex County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Holliston — including 7 based in town.
Contractors serving Holliston
- MASTERPIECE ROOFING INCBased in Holliston★★★★★4.8 rating
- Fair Roofing & GuttersBased in Holliston★★★★☆3.7 rating
23 Water St #207, Holliston, MA 01746
- Steven's General ConstructionBased in Holliston★★★★★5.0 rating
408 Washington St, Holliston, MA 01746
- CF Brothers RoofingBased in Holliston★★★★★5.0 rating
191 Hill St, Holliston, MA 01746
- Hendo Construction INCBased in Holliston★★★★★5.0 rating
49 Windsor Dr, Holliston, MA 01746
- Colantonio IncBased in Holliston★★★★★4.9 rating
16 Everett St A, Holliston, MA 01746
- Services PlusBased in Holliston★★★★★4.8 rating
241 Kuniholm Dr bldg 3, Holliston, MA 01746
- Prestige RoofingServes Holliston · 2.0 mi★★★★★4.9 rating
140 Summer St Rear, Medway, MA 02053
- I T Home Improvement IncServes Holliston · 3.5 mi★★★★★5.0 rating
14 Joanne Dr, Ashland, MA 01721
- The Roof InspectorServes Holliston · 3.7 mi★★★★★5.0 rating
130 Cedar St Unit 6, Milford, MA 01757
- Bruin Remodeling GroupServes Holliston · 3.7 mi★★★★★4.9 rating
208 Pond St, Ashland, MA 01721
- Rehobot carpentryServes Holliston · 3.7 mi★★★★★5.0 rating
136 West union street 1164 main st waltham ma 02451, Ashland, MA 01721
- Masters Touch Design BuildServes Holliston · 3.8 mi★★★★★4.7 rating
77 Main St, Medway, MA 02053
- Eternal Pros Construction IncServes Holliston · 4.0 mi★★★★★5.0 rating
40 Medway Rd, Milford, MA 01757
- Serves Holliston · 4.1 mi
3B Governors Way, Milford, MA 01757
- Handyman BrothersServes Holliston · 4.3 mi★★★★★5.0 rating
27 Cedar St, Milford, MA 01757
- Johnson Construction & RemodelingServes Holliston · 4.5 mi★★★★★4.5 rating
23 Holliston St, Medway, MA 02053
- Warren Home InspectionsServes Holliston · 4.5 mi★★★★★5.0 rating
171 Main St, Ashland, MA 01721
- MN General ConstructionServes Holliston · 4.5 mi★★★★★5.0 rating
39 Hayward St, Milford, MA 01757
- Hocol RoofingServes Holliston · 4.5 mi★★★★★5.0 rating
3 Tanglewood Dr, Milford, MA 01757
- Alfa Construction Inc.Serves Holliston · 4.5 mi★★★★★5.0 rating
34 Pearl St, Bellingham, MA 02019
- Vision Design Build LLCServes Holliston · 4.6 mi★★★★★5.0 rating
50 Main St #5, Ashland, MA 01721
- Serves Holliston · 4.7 mi
41 Sumner St, Milford, MA 01757
- Master RoofServes Holliston · 4.7 mi★★★★★4.9 rating
2 Main St, Milford, MA 01757
- LKS ConstructionServes Holliston · 4.8 mi★★★★★5.0 rating
31 Granite St #3, Milford, MA 01757
- Huerta ConstructionServes Holliston · 4.8 mi★★★★★5.0 rating
6 Purchase St, Milford, MA 01757
- Under Pressure Power Washing Inc.Serves Holliston · 4.8 mi★★★★★4.9 rating
88a Elm St, Hopkinton, MA 01748
- Shaddai Home Improvement LLCServes Holliston · 4.9 mi★★★★★5.0 rating
19 Rosenfeld Ave, Milford, MA 01757
- DGL Construction IncServes Holliston · 4.9 mi★★★★★5.0 rating
89-91 School St, Milford, MA 01757
- AEGIS PRESTIGE LLCServes Holliston · 4.9 mi★★★★★5.0 rating
105 Congress St, Milford, MA 01757
- Regulus ConstructionServes Holliston · 5.0 mi★★★★★4.9 rating
36 West St, Milford, MA 01757
- Nova Top Roofing & SidingServes Holliston · 5.0 mi★★★★★5.0 rating
51 Jefferson St #2, Milford, MA 01757
- Betho Construction IncServes Holliston · 5.0 mi★★★★★5.0 rating
26 Jefferson St, Milford, MA 01757
- SGE Solar - Second Generation EnergyServes Holliston · 5.1 mi★★★★★4.6 rating
85 S Bow St #3376, Milford, MA 01757
- Total Guard Construction IncServes Holliston · 5.1 mi★★★★★5.0 rating
40 Depot St, Milford, MA 01757
- Pessote Construction IncServes Holliston · 5.1 mi★★★★☆4.4 rating
89 Nipmuc Rd, Framingham, MA 01702
- Same Day RoofingServes Holliston · 5.2 mi★★★★★4.9 rating
38 Congress St, Milford, MA 01757
- America Carpentry and Services IncServes Holliston · 5.2 mi★★★★★5.0 rating
27 Congress St, Milford, MA 01757
- LC General ConstructionServes Holliston · 5.3 mi★★★★★4.7 rating
10 Allen Rd, Milford, MA 01757
- JGC Construction Inc.Serves Holliston · 5.3 mi★★★★★5.0 rating
84 Depot St, Milford, MA 01757
- Mike's Roofing ConstructionServes Holliston · 5.3 mi★★★★★5.0 rating
20 Church St, Milford, MA 01757
- SPG Home Services incServes Holliston · 5.4 mi★★★★★4.9 rating
6 Water St, Milford, MA 01757
- Universal RoofingServes Holliston · 5.4 mi★★★★★5.0 rating
763 Waverly St, Framingham, MA 01702
- Serves Holliston · 5.4 mi
21 Bethany Rd, Framingham, MA 01702
- Oteri Construction IncServes Holliston · 5.4 mi★★★★★4.9 rating
801 Waverly St, Framingham, MA 01702
- Patriot Contracting Corporation IncServes Holliston · 5.5 mi★★★★★4.9 rating
873 Waverly St, Framingham, MA 01702
- Oriel's Construction IncServes Holliston · 5.5 mi★★★★★5.0 rating
703 Waverly St, Framingham, MA 01702
- J&R Construction RoofingServes Holliston · 5.5 mi★★★★★5.0 rating
263 Hollis St, Framingham, MA 01702
- Tiago Tiles ServicesServes Holliston · 5.5 mi★★★★★5.0 rating
111 Depot St, Milford, MA 01757
- Exponential Construction Corp.Serves Holliston · 5.5 mi★★★★★5.0 rating
47 Mellen St ll4, Framingham, MA 01702
Roofing in Holliston — what to know
Insurance & rebates
Roofing isn't a Mass Save rebate item, but two factors drive the work in Holliston. The first is inland snow load — MetroWest winters 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 heavy 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.
Holliston 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 Holliston
Holliston 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 MetroWest snow — plus valley and penetration protection. On Holliston's 1950s-70s homes, tear-off frequently uncovers plank or 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 required inspection.
Typical project cost
Holliston sits in the MetroWest/eastern Massachusetts 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 needing sheathing replacement, or when a home carries multiple roof layers. Low-slope porch or addition sections in EPDM rubber are quoted separately.
About Holliston homes
Holliston is a Middlesex County town of about 14,900 residents across roughly 5,700 housing units, a wooded MetroWest suburb between Milford and Ashland. The median home age is around 60 years, so much of the stock dates to the 1950s-70s suburban era — colonials, capes, garrisons, and raised ranches on generous, often heavily treed lots, almost entirely on asphalt shingle.
With many of those roofs into their second or third covering, full tear-offs are the dominant project here. The town's mature tree canopy is a recurring factor: it shades roofs, slows snowmelt, and drops limbs and debris, all of which contribute to moisture and the ice damming common on Holliston's older homes.
Common questions — Roofing in Holliston
- Why do my Holliston home's roof leaks start in winter?
- Usually ice dams. Snow melts over a warm attic, refreezes at the cold eave, and backs water under the shingles — worse on tree-shaded lots where snowmelt is slow. Better attic insulation, air-sealing, and an eave membrane during re-roofing are the fixes.
- Do I need a permit to replace my roof in Holliston?
- Yes. The Holliston Building Department requires a permit for roof replacement, with an inspection afterward. Licensed roofers handle the filing as part of the job.
- My roof is over 20 years old — will my insurer keep covering it?
- Many carriers now surcharge or decline to renew asphalt roofs past about 20 years, which fits many of Holliston'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. Holliston's mature canopy shades roofs, slows snowmelt, and drops limbs and debris — all of which feed moisture damage and ice dams at the eaves. Keep limbs trimmed back and gutters clear.
- Will tear-off uncover hidden damage?
- Often, on 1950s-70s 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.
