Top-rated roofing contractors in Medway, MA

Medway has 10 roof replacement companies on this page; we don't have a license file for Medway, so they're ranked by Google rating instead. Between 50 and 182 reviews back each listing, which is part of how we decided who qualified. See How We Verify for the full method behind Medway's list.

Google Maps ratings checked September 30, 2026 · How we rank

1976median year homes were built

Homes in Medway

86% of occupied homes in Medway are owner-occupied rather than rented.

13,436 people call Medway home as of the latest Census estimate.

Data: U.S. Census Bureau, American Community Survey 5-Year Estimates, table-based Summary File (2024 table-based Summary File) (2024 table-based Summary File).

10 top-rated roofing contractors in and near Medway

Sorted highest first by a Google rating weighted against how many reviews back it; that sort isn't a license check, so confirm the paperwork yourself.

Top-rated roofing contractors in and near Medway, MA, with Google ratings
Rank	Business	Google rating	Reviews	Category	Area	Google Maps listing
1	Master Roof	5.0 out of 5 on Google	182	Roofing contractor	Milford 01757	Google reviews
2	D.R. Roof	5.0 out of 5 on Google	107	Roofing contractor	Bellingham 02019	Google reviews
3	HomeXpert Construction Inc.	5.0 out of 5 on Google	85	Roofing contractor	Milford 01757	Google reviews
4	Yupa's Construction Inc	5.0 out of 5 on Google	84	Roofing contractor	Milford 01757	Google reviews
5	Huerta Construction	5.0 out of 5 on Google	80	Roofing contractor	Milford 01757	Google reviews
6	Leland Siding, Roofing & Windows	5.0 out of 5 on Google	65	Roofing contractor	Medway 02053	Google reviews
7	Tyee Premier Roofing	5.0 out of 5 on Google	64	Roofing contractor	Milford 01757	Google reviews
8	LCT Construction & Services Inc.	4.9 out of 5 on Google	165	Roofing contractor	Hopedale 01747	Google reviews
9	Advantage Home Exteriors	5.0 out of 5 on Google	52	Roofing contractor	Hopedale 01747	Google reviews
10	Synergy Skylights and Roofing	5.0 out of 5 on Google	50	Roofing contractor	Holliston 01746	Google reviews

Questions to ask before you sign

Can you show me your license or registration number, and does it match what's on file with the state?
Will you pull the roofing permit yourself, and will you give me the permit number once it's issued?
How many existing layers are on my roof now, and does that allow a recover under the building code, or does it need to come off?
What's the full written scope: materials, brand, quantity, start date, and payment schedule?
What does the manufacturer's warranty cover, separate from your own workmanship warranty?
Who is responsible if a subcontractor or material supplier on my job goes unpaid?

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