Editorial & advertising disclosure: JDH Remodeling publishes this comparison and is ranked #1 below. We list competing Annapolis-area roofers in good faith using publicly available ratings and licensing data. We do not accept payment for placement. Verify every company's license, insurance, and reviews independently before hiring.
At a Glance
Annapolis roofers compared
A quick side-by-side of the five companies in this guide. Ratings and licensing are reader-verifiable via each profile's Google link below.
Rank
Company
Rating
Best For
License
Warranty
1
JDH RemodelingTop Pick
4.9★ · 425 reviews
Full roof replacement & storm claims
MHIC #137491
50-yr OC Platinum
2
Black Anchor Roofing
5.0★ · 228 reviews
High-volume residential roofing
MHIC Licensed
GAF Golden Pledge eligible
3
Benchmark Roofers
5.0★ · 133 reviews
Boutique residential roofs
MHIC Licensed
CertainTeed 4-Star & GAF
4
Chesapeake Roofing, Windows & Siding
Founded 1987 · 37+ years
Multi-trade roof + siding + windows
MHIC #126792
GAF Certified · CertainTeed 5-Star
5
Alton's Roofing
50+ years in Annapolis
Long-established local roofer
Verify MHIC before hire
Workmanship (per operator)
Methodology
How We Ranked the Best Roofers in Annapolis, MD
Every roofer on this list met four objective criteria:
Active Maryland Home Improvement Commission (MHIC) licensing. Verified through the MHIC public license search. Any contractor without a current MHIC license is automatically excluded.
Minimum 4.5-star Google rating with at least 50 reviews. Review depth matters more than a perfect score from 10 reviews. We weighted review count alongside rating.
Demonstrated local service history in Anne Arundel County. Either a physical location in or near Annapolis, or a documented service area covering Annapolis as a primary market.
Advanced manufacturer credentials where applicable. Owens Corning Platinum, GAF Master Elite, or CertainTeed 4-Star ShingleMaster status reflects extended training, warranty access, and accountability that standard licensing does not.
Independence note: JDH Remodeling produces this list. JDH ranks #1 because of verifiable credentials: Owens Corning Platinum (held by fewer than 1% of US roofers) and HAAG Master Roof Inspector. The other 4 contractors are evaluated against the same criteria, with the same level of detail.
The Rankings
5 best roofing companies in Annapolis, MD
Ranked on rating volume, licensing, warranty strength, and local track record. Verify each company yourself with the Google link in every card.
Top Choice
1
JDH Remodeling
Owens Corning Platinum Preferred · Serving Annapolis & Anne Arundel County
★★★★★
4.9 / 5
425 Google reviews · 1,498+ multi-platform
Best for Full roof replacement & insurance storm claims
JDH Remodeling is a MHIC-licensed (#137491), Owens Corning Platinum Preferred contractor serving central Maryland since 1986, with 1,460+ documented roof inspections on record. Annapolis homeowners choose JDH for transparent scoped pricing, a manufacturer-backed 50-year warranty, and a documented storm-claim process.
Strengths
Owens Corning Platinum Preferred, top 1% of contractors
50-year manufacturer warranty in writing
4.9★ across 425 Google reviews, 1,498+ multi-platform
Documented insurance & storm-claim support
$8M liability coverage · MHIC #137491
Consider If
Booked 1 to 2 weeks out in peak storm season
Focused on full systems, not one-shingle patch jobs
Black Anchor Roofing is a Maryland-licensed contractor based in Annapolis at Moreland Parkway. The operator focuses on residential roof system work, including asphalt, metal, and storm repair, has accumulated a 5.0-star rating across 228 Google reviews, and serves Annapolis as a primary market.
Strengths
228 verified Google reviews at a 5.0 rating, top-quartile review depth
Annapolis-resident operation on Moreland Parkway near the Eastport district
Dedicated roof system specialization across asphalt, metal, and storm repair work
Limitations
Roof-focused brand vs JDH's full multi-trade exterior platform (roof + siding + windows + gutters under one project owner)
No published Owens Corning Platinum or HAAG Master credential on their public GBP profile
Benchmark Roofers is a Maryland-licensed contractor based in Annapolis at Giddings Avenue. The operator focuses on residential roof system work, including asphalt, metal, and storm repair, has accumulated a 5.0-star rating across 133 Google reviews, and serves Annapolis as a primary market.
Strengths
133 Google reviews at a 5.0 rating, established customer satisfaction history
Annapolis-resident operation on Giddings Avenue near Forest Drive
Dedicated roof system specialization across asphalt, metal, and storm repair work
Limitations
Roof-focused brand vs JDH's full multi-trade exterior platform (roof + siding + windows + gutters under one project owner)
No published Owens Corning Platinum or HAAG Master credential on their public GBP profile
Best for Multi-trade roof + siding + windows in Anne Arundel County
Chesapeake Roofing, Windows & Siding Inc. is a Maryland-licensed contractor (MHIC #126792) headquartered at 910 Soaring Eagle Ct in Davidsonville, roughly 10 miles west of downtown Annapolis. Founded in 1987, they run a 37+ year multi-trade exterior operation across roofing, siding, and windows, and consistently appear in Google's Annapolis roofing map pack across every major search query. Their public site states they are "the only DMV company with the prestigious 5-Star Installer Certification for both CertainTeed Siding and Roofing."
Strengths
37+ years in business (founded 1987), among the longest-tenured roofers in the greater Annapolis market
MHIC #126792 published in their site footer, verifiable via the Maryland MHIC public search
Consistent inclusion in Google's Annapolis roofing local pack across every major query in our independent SERP research
Advanced manufacturer credentials: GAF Certified Contractor and CertainTeed 5-Star Installer (both roofing and siding)
Limitations
Headquartered in Davidsonville, roughly 10 miles west of downtown Annapolis, not Annapolis-resident
No published Owens Corning Platinum or HAAG Master certification on their public profile
Alton's Roofing is an Annapolis-based residential roofing contractor at 66 Silopanna Rd near the Bay Ridge / Hillsmere corridor, in operation for more than 50 years per their public site. They appear in Google's top-10 organic results across every major Annapolis roofing query in our independent SERP research, indicating strong local search authority. Their public site displays a 5-star customer rating; specific review count and MHIC license number are not published on their homepage, so homeowners should verify licensing via the Maryland MHIC public search before hiring.
Strengths
50+ years in business, one of the longest-tenured Annapolis-resident roofing operations
Physical Annapolis address at 66 Silopanna Rd near the Bay Ridge and Hillsmere neighborhoods
Consistent top-10 Google organic ranking across every major Annapolis roofing search query in our independent SERP research
Limitations
MHIC license number not published on their public website (verify via Maryland MHIC public search before hiring)
No published Owens Corning Platinum or HAAG Master credential
Roof-focused brand vs JDH's full multi-trade exterior platform (roof + siding + windows + gutters)
Most full asphalt-shingle roof replacements in Annapolis and Anne Arundel County run $14,000 to $32,000 in 2026. Smaller or simpler roofs can fall below that range; large, steep, or complex roofs run higher. Always get the scope and warranty in writing.
Maryland home-improvement contractors must hold an active MHIC license. Ask for the number and look it up on the Maryland Department of Labor's license-lookup tool. JDH Remodeling's MHIC license is #137491. Also confirm general-liability insurance before any work begins.
Ask for the MHIC license number, proof of liability insurance, a written scope of work, the manufacturer warranty offered, and references or recent local addresses. Get 2 or 3 written estimates and compare what's actually included, not just the bottom-line price.
A manufacturer warranty (e.g. Owens Corning's 50-year Platinum) covers the materials and is only available through certified contractors. A workmanship warranty covers the installer's labor. The strongest protection is having both, so ask each company which they provide and for how long.
Yes. JDH provides a documented storm-claim inspection and works directly with homeowners through the insurance process across central Maryland. Call (443) 241-7356 to schedule a free inspection.
Get a free roof inspection from Annapolis's #1-ranked roofer
No-pressure, no-obligation. A JDH inspector will assess your roof and provide a scoped, written estimate.
