Benchmark Roofers
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24 companies listed · 11 in Annapolis · 4 open 24/7 · 18 open weekends · all 24 rated 4.5+
Data verified October 21, 2026
Listed for homeowners in and around Annapolis, MD, these 24 companies take roofing work. What each one claims about tear-offs, materials and workmanship cover is taken from its own website; ratings and quoted lines come from public reviews.

Of the 24 companies we list here, 11 are in Annapolis itself and 13 come from towns including Severna Park (2, 8 mi), Arnold (1, 6 mi) and Gambrills (1, 9 mi). The companies on this page are rated from 4.5 to 5.0 across 2,147 reviews; 15 have 50 or more reviews. When customers rate these companies on specific qualities, they most often praise professionalism (92%), quality (85%) and responsiveness (85%). The topics that come up most in reviews of the companies on this page are "estimates", "price" and "communication". 4 are open around the clock; 18 are open on Saturdays and 6 on Sundays. The services the companies on this page list most often on their websites are siding (6), gutters (4), roofing (4), windows (4) and doors (2). 17 show a license on their websites and 11 have a BBB rating of A or A+. 17 have ten or more years of experience, the longest 70 years. 4 offer emergency call-outs; 10 offer financing or payment plans; 16 give free estimates; 7 are family- or locally-owned and 6 list coupons or special offers. We count these figures across the companies on this page; distances are straight-line, and hours and prices change, so confirm the details with the company before you book.
Free estimates are stated by 16 of the 24 companies on this page. A free visit is normal for roof work, but it is a sales call as well as an inspection, so ask for the findings in writing with photos of what was seen up there. Get a second look before you commit to a full replacement.
- “The Benchmark roofing crew showed up on time and did a fantastic job from removing the old shingles to cleaning up the work site -- completing the work in one day.” — customer of Benchmark Roofers
- “I am very happy with the job they did and would highly recommend them to anyone that is looking to do a roof replacement.” — customer of Ram Construction
- “They helped me get a full roof replacement and new gutters along with some minor interior repairs and the service was top notch from start to finish!” — customer of Wells Home Improvements
- “Justin and the entire crew from Benchmark Roofers provided excellent service during our roof replacement.” — customer of Benchmark Roofers
Excerpts from public reviews of the companies listed on this page.
Best Time of Year to Replace a Roof: The 40 Degree Rule
Chimney Inspection Levels 1, 2 and 3: Which Do You Need?
If a Contractor Gets Hurt at Your House, Who Pays?
Contractor Recovery Funds: How to Claim, State by State
How Much to Pay a Contractor Up Front | State Deposit Caps
How to Compare Contractor Bids: A Line-by-Line Guide