1 Pheasant Ln, South Dennis, MA 02660
Roofing in Dennis, Massachusetts
Compare contractors serving Dennis, Barnstable County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Dennis — including 8 based in town.
Contractors serving Dennis
- O.T.R. Siding & Trim CorpBased in Dennis★★★★☆3.9 rating
- CPP Home Builders and Remodeling on Cape CodBased in Dennis★★★★★5.0 rating
394 Main St Unit 1, West Dennis, MA 02670
- G.I.P. Construction & Remodeling Inc.Based in Dennis★★★★★5.0 rating
45 Lockwood Dr, South Dennis, MA 02660
- Coastline ConstructionBased in Dennis★★★★★5.0 rating
494 Upper County Rd, South Dennis, MA 02660
- Custom Crafted HomesBased in Dennis★★★★★5.0 rating
667 Main St Building 3-30, Dennis, MA 02638
- Betterwood Homes Inc.Based in Dennis★★★★★5.0 rating
744 Main St, Dennis, MA 02638
- Meyer and Sons Builders, IncBased in Dennis★★★★★4.8 rating
852 Main St, West Dennis, MA 02670
- Philbrook Construction Services Group, Inc.Based in Dennis★★★★★5.0 rating
107 Beach St, Dennis, MA 02638
- Imagine ConstructionServes Dennis · 2.3 mi★★★★★5.0 rating
4 Ruth St, Harwich, MA 02645
- HyTech Roofing SolutionsServes Dennis · 2.5 mi★★★★★5.0 rating
714A MA-6A, Yarmouth Port, MA 02675
- Junior's Odd JobsServes Dennis · 2.5 mi★★★★☆4.3 rating
178 Main St, Harwich, MA 02645
- PLJ Carpentry Inc.Serves Dennis · 3.0 mi★★★★★4.9 rating
15 Fruean Ave, South Yarmouth, MA 02664
- Gulfeagle SupplyServes Dennis · 3.5 mi★★★★☆3.7 rating
181 Queen Anne Rd, Harwich, MA 02645
- Cape Cod Home ImprovementServes Dennis · 5.9 mi★★★★★5.0 rating
27 Mill Pond Rd, West Yarmouth, MA 02673
- Sullivan Home ImprovementServes Dennis · 5.9 mi★★★★★5.0 rating
620 Yarmouth Rd, Hyannis, MA 02601
- Mr. Painting and More INCServes Dennis · 6.2 mi★★★★★4.9 rating
105 Ferndoc St c3, Hyannis, MA 02601
- Duomo Group IncServes Dennis · 6.8 mi★★★★★5.0 rating
270 Communication Wy #4g, Hyannis, MA 02601
- Belport Building & Remodeling, LLCServes Dennis · 6.8 mi★★★★★4.8 rating
270 Communication Wy #2H, Hyannis, MA 02601
- Keen Mind Home ImprovementServes Dennis · 6.9 mi★★★★★5.0 rating
42 Kings Way, Hyannis, MA 02601
- Starbuck Construction ServicesServes Dennis · 7.0 mi★★★★★5.0 rating
67 Willow Ave, Hyannis, MA 02601
- Shepley Wood ProductsServes Dennis · 7.0 mi★★★★★4.6 rating
60 Benjamin Franklin Way, Hyannis, MA 02601
- George W Blakely BuildersServes Dennis · 7.0 mi★★★★★5.0 rating
11 Cit Ave, Hyannis, MA 02601
- Wisdom Home GroupServes Dennis · 7.1 mi★★★★★4.8 rating
178 Thornton Dr Unit 1-D, Hyannis, MA 02601
- United constructors incServes Dennis · 7.1 mi★★★☆☆3.0 rating
150 Hinckley Rd, Hyannis, MA 02601
- Gutter Pro EnterprisesServes Dennis · 7.3 mi★★★★★5.0 rating
100 Independence Dr Suite 7-811, Hyannis, MA 02601
- Flawless Facilities MaintenanceServes Dennis · 7.4 mi★★★★★5.0 rating
94 Quaker Rd, Hyannis, MA 02601
- Compass Home GroupServes Dennis · 7.5 mi★★★★★5.0 rating
47-4 Warehouse Rd, Hyannis, MA 02601
- Total Care PaintingServes Dennis · 7.5 mi★★★★★5.0 rating
576 Main St Unit 3, Hyannis, MA 02601
- Schmidt PaintingServes Dennis · 7.6 mi★★★★★4.9 rating
14 Pepper Ln, Hyannis, MA 02601
- Hickory Harbor HomesServes Dennis · 7.6 mi★★★★★5.0 rating
1070 Iyannough Rd #323, Hyannis, MA 02601
- Barnstable Home ImprovementServes Dennis · 7.6 mi★★★★★5.0 rating
1070 Iyannough Rd suite 356, Hyannis, MA 02601
- Best Quality Painting CompanyServes Dennis · 7.6 mi★★★★★5.0 rating
9 Kelley Rd, Hyannis, MA 02601
- Byam ConstructionServes Dennis · 7.7 mi★★★★★4.9 rating
124 Sea St, Hyannis, MA 02601
- Perullo ConstructionServes Dennis · 7.8 mi★★★★★5.0 rating
90 Commerce Park, South Chatham, MA 02659
- LEO'S PAINTING & HOME SOLUTIONSServes Dennis · 7.9 mi★★★★★4.9 rating
205 Beth Ln, Hyannis, MA 02601
- Falcon Homes General ContractorServes Dennis · 8.1 mi★★★★★4.9 rating
10 Pine Grove Ave STE 2, Hyannis, MA 02601
- Serves Dennis · 8.4 mi
28 Marks Path, Hyannis, MA 02601
- Best Deal Home GroupServes Dennis · 8.4 mi★★★★★5.0 rating
52 Goose Point Rd, Centerville, MA 02632
- Built Different Construction, Inc.Serves Dennis · 8.4 mi★★★★★5.0 rating
745 Falmouth Rd, Hyannis, MA 02601
- Peter E Comeau Builders IncServes Dennis · 8.5 mi★★★★★4.8 rating
42 Wolley Rd #2410, Hyannis, MA 02601
- Coastal Roofing & SidingServes Dennis · 8.6 mi★★★★★4.9 rating
850 Falmouth Rd, Hyannis, MA 02601
- Outside Cleaners LLCServes Dennis · 9.0 mi★★★★★5.0 rating
3844 Main St, Brewster, MA 02631
- Cape Cod RenovationServes Dennis · 10.0 mi★★★★★4.9 rating
1645 Falmouth Rd, Centerville, MA 02632
- Stuart ConstructionServes Dennis · 10.4 mi★★★★★5.0 rating
1851 Falmouth Rd, Centerville, MA 02632
- MAZZEO Construction LLCServes Dennis · 10.6 mi★★★★★4.6 rating
56 Main St Unit F, Orleans, MA 02653
- Herks Carpentry IncServes Dennis · 10.8 mi★★★★★5.0 rating
23 Derby Dr, West Barnstable, MA 02668
- ANPoint ExteriorsServes Dennis · 10.8 mi★★★★★5.0 rating
221 Saddler Ln, West Barnstable, MA 02668
- Celtic Services, Inc PowerwashingServes Dennis · 11.8 mi★★★★★5.0 rating
599 Old Falmouth Rd, Marstons Mills, MA 02648
- Paul Johnson Home ImprovementServes Dennis · 12.0 mi★★★★★5.0 rating
15 Mallard Ln, Eastham, MA 02642
- Rogers & Marney Builders Inc.Serves Dennis · 12.3 mi★★★★★4.9 rating
445 Osterville West Barnstable Rd #2, Osterville, MA 02655
Roofing in Dennis — what to know
Insurance & rebates
Roofing isn't a Mass Save rebate item, but two financial threads shape a Dennis re-roof. The first is insurance: as Cape Cod high-wind territory, carriers scrutinize roof age and wind resistance, and many will surcharge or non-renew an asphalt roof past 15-18 years — sooner than inland Massachusetts. Wind and storm-damage claims are common after named storms; document damage before filing, and a new wind-rated roof often earns a premium reduction. Salt-corroded fasteners near the water are a genuine durability factor.
Dennis is in Eversource territory, so the home qualifies for Mass Save weatherization, and the Cape Light Compact sometimes layers additional offers. The roof isn't subsidized, but a tear-off is the cheapest moment to add attic insulation and air-sealing — work Mass Save covers at 75% or more for Eversource customers, valuable on the town's older bayside homes.
Permits in Dennis
Dennis 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 and around penetrations, and Cape high-wind code provisions drive enhanced fastening and reinforced edge metal at permit review. The key Cape-specific step is historic review: Old King's Highway covers the Route 6A corridor through Dennis Village, and any visible roof material change there — for example switching from cedar to asphalt — needs Historic District Commission approval. Licensed contractors handle the filings and inspection.
Typical project cost
Dennis runs a bit above the state average because wind-rated detailing, corrosion-resistant flashing, and seasonal labor demand all add cost. A standard asphalt re-roof on a typical single-family or cottage runs roughly $8,000-$18,000; larger bayside homes push toward $25,000. Cedar shingle re-roofs on Route 6A antique homes are substantially higher — often $20,000-$45,000 — given material and labor. Flat EPDM rubber on condo and low-slope sections is quoted separately. Waterfront sites with long access and steep dormered rooflines reach the upper end.
About Dennis homes
Dennis is a Barnstable County town on the Mid-Cape, stretching from Cape Cod Bay to Nantucket Sound — about 14,700 year-round residents but roughly 15,300 housing units, a striking gap that reflects how heavily seasonal this town is. The median home age is around 56 years, a mix spanning antique homes along Route 6A in Dennis Village, postwar cottages, and condo and resort development in Dennis Port and West Dennis.
Roofs run mostly asphalt shingle and cedar, with cedar more common on the bayside antique homes. The defining roofing variable is coastal exposure: salt air corrodes fasteners and flashing, and steady wind drives shingle uplift, so corrosion-resistant detailing matters far more than inland.
Common questions — Roofing in Dennis
- Does salt air affect roofs in Dennis?
- Yes. Within a mile or so of either shore, salt corrodes standard fasteners and flashing. Roofers here use stainless or coated fasteners and corrosion-resistant aluminum or copper flashing on coastal sites.
- Will my Route 6A home need historic approval to re-roof?
- If you're changing the visible material — say from cedar to asphalt or metal — yes. Old King's Highway covers the Route 6A corridor through Dennis Village, and visible roof changes need Historic District Commission approval. Like-for-like replacement is simpler.
- How does roof age affect my Cape Cod insurance?
- Closely. In high-wind coastal territory, carriers often surcharge or decline to renew asphalt roofs past 15-18 years. A new wind-rated roof can earn a premium reduction and keep coverage available.
- I have a seasonal home in Dennis — does that change anything?
- It raises the stakes. Unoccupied seasonal homes can develop leaks and storm damage that go unnoticed for months. A wind-rated roof and an annual inspection help protect a property you're not there to watch.
- Cedar or asphalt for a bayside Dennis home?
- Both are common. Cedar fits the antique aesthetic and may be expected on Route 6A, but it costs $20,000-$45,000 and needs upkeep. Architectural asphalt is far cheaper and now comes in cedar-look profiles; historic rules may steer the choice.
