Best roofing contractors in Milford

★★★★★4.9 (154 reviews)score 92/100

A Plus Exterior backs up a 4.9 rating across 154 reviews with a Platinum Certified Owens Corning credential and HAAG-certified inspectors, which shows up in reviewers' accounts of same-day leak response and a full roof replacement finished in a single day with an eight-person crew. Leadership under Alex and Ray quotes promptly and handles surprises like hidden rot without inflating the price after the fact.

• Platinum Certified Owens Corning contractor with HAAG-certified inspections
• Same-day response on emergency leaks
• Debris cleanup with magnetic sweeps and lift equipment for old shingles
• Handles roofs, gutters, siding, and windows under one crew

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

★★★★★5 (44 reviews)score 87/100

Owner Mark Villano personally runs jobs for this Milford crew, and reviewers describe proposals detailed enough to trust and cleanup thorough enough that properties look undisturbed afterward. A perfect 5.0 rating across 44 reviews, built mostly on word-of-mouth, reflects fair pricing that's never the cheapest bid but consistently seen as honest.

• Owner Mark Villano manages jobs on-site personally
• Crew coordination that wraps most jobs in hours, not days
• Meticulous cleanup and site restoration
• Willing to reschedule around weather rather than rush

Services: flat roofing commercial, roof repair

★★★★★4.9 (96 reviews)score 87/100

JP Carroll fields multiple named project managers who send progress photos and answer questions throughout, which is part of why condo associations and repeat customers trust them with multi-unit roofs alongside routine replacements and storm repair. A 4.9 rating over 96 reviews holds up well, though some customers flag pricing as higher than expected given current material costs.

• Named project managers stay responsive and share progress photos
• Crews often arrive early and finish same-day on smaller jobs
• Thorough site cleanup and property protection
• Experience with slate, shingle, metal, and flat roofing, including large condo projects

Watch out: A few reviewers note pricing runs higher, which they attribute to current material costs.

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

★★★★★5 (35 reviews)score 86/100

Cooper Modifications puts named leads (Anthony, John, Matt) on daily oversight of each job, and across 35 reviews every single one is five stars with no complaints on record. Quoted prices reportedly match final invoices, and crews protect surrounding structures during roof, siding, gutter, and chimney work.

• Named project leads provide daily communication
• Quoted prices match final invoices with no surprise charges
• Protective measures around existing structures during work
• Clean, detail-oriented handoff and walkthrough

Services: flat roofing commercial, metal roofing, gutter services

★★★★★5 (25 reviews)score 85/100

All 25 of PRC Builders' Google reviews are five stars, with owner Pat cited for same-day emergency repairs and full roof replacements wrapped in one to two days. Reviewers specifically call out fair pricing without upselling, though the smaller review count means this track record is still building.

• Same-day emergency roof repair
• One-to-two-day full roof replacements
• Fair pricing with no upselling
• Owner-led communication and spotless cleanup

Watch out: A newer profile with 25 reviews, so the track record is thinner than the top names on this list.

Services: roof replacement installation, gutter services

★★★★★4.9 (41 reviews)score 84/100

Jessie's crew at Bay Restorations gets called in on problems other contractors couldn't solve, spanning traditional, rubber, and commercial roofing plus siding, windows, and interior remodels. A 4.9 rating across 41 reviews reflects punctual, clean work, with a single missed estimate appointment as the main blemish on an otherwise strong record.

• Solves commercial roof problems other contractors miss
• Bonded and licensed with a long local operating history
• No leaks reported years after installation
• Thorough daily jobsite cleanup

Watch out: One reviewer reported a missed estimate appointment.

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

★★★★★5 (18 reviews)score 83/100

Charter Oak, led by owner Mike Plaskon, has a perfect 5.0 rating across all 18 reviews, with customers consistently noting jobs that finish ahead of schedule at fair prices. The review count is smaller than the top of this list, but the sentiment is uniformly strong.

• Fair pricing with free roof inspections
• Frequently finishes ahead of schedule
• Clear communication throughout the job
• Licensed and insured

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

★★★★★5 (12 reviews)score 81/100

Jonathan's crew at Ace Roofing earns praise for showing up same-day on repairs and walking homeowners through insurance claims, even on small jobs some other contractors turned down. All 12 reviews are five-star, and complimentary roof inspections come standard with the work.

• Same-day or next-day emergency repairs
• Guides homeowners through insurance claims
• No job considered too small
• Complimentary roof inspections included

Watch out: A smaller review base of 12, so worth confirming current availability directly.

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

★★★★★5 (15 reviews)score 80/100

James and his team at Approved Roofing show up on time and stay in touch through the whole job, which is a common thread across their 15 five-star reviews covering both repairs and replacements. Fair pricing and attention to detail come up repeatedly as reasons customers say the work exceeded expectations.

• Quick, on-time arrival
• Fair pricing
• Quality workmanship with attention to detail
• Consistent communication throughout the project

Watch out: Review volume is modest at 15, so it's a newer public track record.

Services: roof replacement installation

★★★★★4.8 (45 reviews)score 78/100

Berkeley Exteriors has run as a family operation out of Milford since 1992, and Chris and Anthony's crews are cited for on-time, on-budget work with 50-year roof warranties standard. Recent reviews are strong, though a long-standing complaint from 20 years back about window trim and warranty follow-up under previous leadership still shows up in the record.

• 50-year roof warranties and quality materials standard
• Pricing that reviewers say beats competitors
• Family-run leadership involved directly in projects
• Coordinates insurance claims and works around client schedules

Watch out: An older complaint (roughly 20 years back) about window trim and warranty follow-up predates current leadership's more recent track record.

Services: metal roofing, roof inspection insurance, gutter services

★★★★★4.6 (89 reviews)score 76/100

Prime Energy Services pairs solar installation with roofing work, and most of its 89 reviews praise professional installation and responsive communication. A run of recent one-star reviews raising warranty enforcement and post-sale responsiveness concerns is worth weighing against the otherwise solid installation reputation.

• Professional installation workmanship
• Integrated solar and roof project management
• Named, experienced staff on projects
• Claims 20 years in operation

Watch out: Recent reviews flag warranty disputes and slow response to post-sale issues, so get warranty terms in writing upfront.

Services: metal roofing

★★★★★5 (11 reviews)score 72/100

This is a separate A Plus Exterior LLC listing from the top-ranked profile, with its own set of 11 five-star reviews praising responsive service, competitive pricing, and insurance claims handling on siding and roofing work. The smaller review count means this listing's track record is still limited.

• 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 this specific listing, so treat the track record as early-stage.

Services: roof replacement installation, gutter services, roof repair

★★★★★5 (2 reviews)score 70/100

Professional Roofers LLC has just two reviews on record, both five-star, describing staff who spotted storm damage other inspections missed and guided customers through insurance approval on roof and window jobs. That's too small a sample to draw firm conclusions from, but the specifics reported are positive.

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

Watch out: Only two reviews on record, so this is a limited sample to judge consistency from.

Services: roof inspection insurance, metal roofing

★★★★★5 (3 reviews)score 68/100

Oaklands Roofing & Masonry has three five-star reviews citing a technically knowledgeable owner who stays on-site daily until a job is finished, with one customer returning for repeat work. It's a very small sample, but what's there points to hands-on, responsive service.

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

Watch out: Only three reviews on record, so there isn't much public track record yet.

Services: roof repair

★★★★★4.5 (13 reviews)score 67/100

Rick's Roofing And Siding draws praise for fast scheduling and quotes that beat competitors on full tearoff-and-replace jobs, including permits and dumpster costs built into the price. Sentiment is mixed rather than uniformly positive: reviewers note communication gaps on smaller repair jobs and one long-standing quality complaint from a past installation.

• Owner-operated with 20+ years of local experience
• Quotes often undercut competitors on full tearoff jobs
• Permits and dumpster included in pricing
• Thorough cleanup after larger jobs

Watch out: Some reviewers report weaker communication on small repair requests, and there's a past complaint about installation quality holding up years later.

Services: roof repair, gutter services