Best roofing contractors in Milford

★★★★★4.9 (158 reviews)score 90/100

A Plus Exterior posts the highest composite score in Milford on the back of 158 reviews at a 4.9 average, with owner Alex quoting same-day and crews responding to emergencies within the hour. The jobsite discipline (magnetic nail sweeps, tarps, lift equipment) shows up repeatedly in customer accounts.

• Same-day quotes directly from owner Alex
• Emergency response within about an hour
• Magnetic nail sweep and tarp protection on every job
• Honest assessments that avoid unnecessary repairs

Watch out: A few customers noted communication before the crew arrives can lag.

Services: metal roofing, roof inspection insurance, roof replacement installation, roof repair

★★★★★5 (47 reviews)score 88/100

Advantage Roofing carries a perfect 5.0 average across 47 reviews, with Mark Villano personally overseeing shingle, flat, and rubber roof jobs that typically wrap in a single day. Reviewers consistently mention fair, detailed pricing and spotless cleanup, and no complaints surface in the available feedback.

• Same-day completion on most jobs
• Owner Mark Villano manages projects personally
• Thorough on-site cleanup after every job
• Fair, detailed pricing

Services: gutter services, flat roofing commercial, roof repair, metal roofing

★★★★★4.9 (96 reviews)score 87/100

JP Carroll Roofing pairs a 4.9 average over 96 reviews with a bench of named project managers who share progress photos and stay reachable throughout a job. The company handles everything from routine repairs to full multi-unit condo re-roofs, and repeat customers over a decade back up the consistency.

• Named project managers stay responsive with photo updates
• Same-day completion on smaller jobs
• Handles large multi-unit and commercial-scale projects
• Thorough site cleanup and property protection

Watch out: Some reviewers flagged pricing as higher than expected, though tied to current material costs.

Services: roof repair, metal roofing, roof replacement installation, roof inspection insurance

★★★★★5 (38 reviews)score 87/100

Cooper Modifications holds a perfect 5.0 average across 38 reviews and 30-plus years of combined crew experience backed by GAF and James Hardie certification. Staff like John Daley and Anthony Alvarado send daily photo updates, and reviewers repeatedly praise the meticulous detail work around windows and corners.

• Daily photo updates and transparent communication
• GAF and James Hardie certified crew leadership
• High-quality materials and careful detail work
• Meets timelines without budget surprises

Services: flat roofing commercial, metal roofing, roof repair, roof replacement installation

★★★★★5 (25 reviews)score 85/100

PRC Builders has a clean 5.0 average across 25 reviews, with owner Pat handling same-day emergency repairs and two-day full roof replacements without upselling extras. Cleanup and professionalism come up in every review, though the smaller review count keeps confidence at medium rather than high.

• Same-day emergency repair response
• 1-2 day roof replacements
• Fair pricing with no upselling
• Owner-led communication throughout

Watch out: Fewer reviews than the top contractors, so the track record is thinner.

Services: gutter services, roof repair, roof replacement installation, 24 7 emergency roofing

★★★★★4.9 (43 reviews)score 84/100

Bay Restorations earns a 4.9 average over 43 reviews, with multiple customers reporting no leaks years after the crew, led by Jessie, finished. The business handles metal, flat, and traditional roofing plus siding for both residential and commercial clients, backed by A+ BBB status and bonding.

• Results holding up with no leaks years later
• Clean jobsites with daily debris removal
• Handles both residential and commercial roofing
• A+ BBB rating and bonded

Watch out: One reviewer reported being stood up for an estimate appointment.

Services: metal roofing, gutter services, roof replacement installation, flat roofing commercial

★★★★★5 (21 reviews)score 84/100

Charter Oak Roofing has a perfect 5.0 average across all 21 reviews, with owner Mike Plaskon personally handling consultations and reportedly undercutting competitor quotes. One reviewer bought a home with hidden storm damage and got a fair, fast full replacement, the kind of story that shows up repeatedly in the feedback.

• Owner Mike Plaskon handles consultations directly
• All reviews rate five stars
• Fast response and turnaround times
• Pricing that undercuts competitors

Watch out: Review volume (21) is smaller than the top-ranked contractors.

Services: metal roofing, roof repair, roof replacement installation, flat roofing commercial

★★★★★5 (14 reviews)score 82/100

Ace Roofing holds a perfect 5.0 average across 14 reviews, with Jonathan's crew arriving quickly for emergencies and walking customers through insurance claims rather than just doing the repair. Reviewers also mention the crew treats small repair jobs with the same care as full replacements.

• Same-day emergency response
• Handles repairs and replacements equally well
• Guides customers through insurance claims
• Fair, reasonable pricing

Watch out: Review count (14) is modest, so weigh the pattern rather than the volume.

Services: roof inspection insurance, metal roofing, flat roofing commercial, roof repair

★★★★★5 (15 reviews)score 80/100

Approved Roofing carries a 5.0 average across 15 reviews, with James and his crew earning praise for arriving on time and staying in touch throughout the project. Reviewers describe results that exceed expectations on both repairs and full replacements.

• Quick response and on-time arrival
• Professional, experienced crew
• Fair pricing
• Good communication throughout the job

Watch out: Smaller review base (15) and a recency score below the top tier.

Services: roof repair, roof replacement installation, gutter services

★★★★★4.8 (45 reviews)score 78/100

Berkeley Exteriors has run out of Milford since 1992 and pairs recent five-star roofing work with 50-year warranties on materials. Chris and Anthony lead crews that reviewers describe as clean and communicative, and the business also does gutters and siding alongside roofing.

• 50-year roof warranties and quality materials
• Family-run since 1992, serving Fairfield and New Haven counties
• Pricing that beats competitor quotes
• Crews keep jobsites clean and flex around schedules

Watch out: An older complaint (about 20 years back) cites unresolved window trim and warranty follow-up under previous leadership.

Services: metal roofing, roof inspection insurance, roof replacement installation, gutter services

★★★★★4.6 (89 reviews)score 76/100

Prime Energy Services draws a 4.6 average across 89 reviews, with the bulk of praise going to professional solar installation work and responsive communication during the sale and install. It's worth including for anyone bundling roof work with solar, though recent reviews raise real questions about warranty follow-through.

• Professional installation workmanship
• Clear explanations during the sales process
• Integrated solar and roof project management
• Named staff cited by reviewers

Watch out: Recent one-star reviews flag warranty disputes and slow response to post-sale problems.

Services: roof repair, metal roofing, roof replacement installation, gutter services

★★★★★5 (11 reviews)score 72/100

This second, separately-listed A Plus Exterior LLC holds a 5.0 average across 11 reviews and carries Owens Corning Platinum Preferred Contractor status, with reviewers pointing to skilled siding and roofing work plus hands-on insurance claim coordination. The review count is small, so treat the score as an early signal rather than a settled track record.

• Owens Corning Platinum Preferred Contractor
• Insurance claim coordination and handling
• Custom in-house fabrication
• Responsive, same-day service availability

Watch out: Only 11 reviews on record, which keeps confidence low despite the perfect rating.

Services: gutter services, roof repair, roof replacement installation, roof inspection insurance

★★★★★5 (2 reviews)score 70/100

Professional Roofers LLC has just two reviews, both five stars, describing a team that caught storm damage other inspectors missed and guided the claim from inspection through approval. It's a promising early signal for insurance-heavy jobs, but the sample size is very small.

• Navigates insurance claims from inspection to approval
• Spots storm damage clients miss

Watch out: Only two reviews on record, so this is a low-confidence pick.

Services: roof inspection insurance, gutter services, metal roofing, roof repair

★★★★★5 (2 reviews)score 70/100

JLP Pro Services has two five-star reviews praising quick issue resolution and strong customer care, plus OSHA and GAF certification behind the roofing and siding work. The free-gutters-with-new-roof offer and insurance claims handling stand out, but there's very little review history to lean on yet.

• OSHA and GAF certified
• Free gutters included with a new roof purchase

Watch out: Only two reviews so far, making this an early-stage pick.

Services: roof inspection insurance, roof repair, gutter services, flat roofing commercial

★★★★★5 (3 reviews)score 68/100

Oaklands Roofing & Masonry has three five-star reviews describing a technically knowledgeable owner who stays on-site daily until a job is finished, with at least one customer returning for repeat work. It's a small sample, but the combination of roofing and masonry skill is a genuine niche.

• Technically knowledgeable owner
• Reliable daily presence until the job is done

Watch out: Only three reviews on record, so confidence in the pattern is limited.

Services: gutter services, roof repair, roof replacement installation