Best gutters & siding contractors in Milford

★★★★★4.9 (154 reviews)score 92/100

A Plus Exterior tops the list with the widest review base in Milford's gutters and siding field and a 4.9 average across 154 reviews. Crews are known for showing up on time, protecting the property with tarps and magnetic sweeps, and keeping owners Alex and Ray in the loop when hidden problems like rot turn up mid-job. When a gutter color came out wrong on one job, the team fixed it within 24 hours.

• Owens Corning Platinum Certified contractor
• HAAG certified for roof inspections
• Same-day response to emergency leaks
• Debris cleared with magnetic sweeps and lift equipment

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

★★★★★5 (35 reviews)score 86/100

Cooper Modifications posts a perfect 5.0 across 35 reviews with no complaints on record, backed by named project leads (Anthony, John, Matt) who stay in daily contact through roof, siding, gutter, and chimney work. Customers point to quotes that match the final invoice and crews that protect the property before tearing into a job.

• Named leads manage each project start to finish
• Daily communication throughout the job
• Quoted prices hold through the final invoice
• Crews protect the property and clean up thoroughly

Services: flat roofing commercial, metal roofing, gutter services

★★★★★5 (25 reviews)score 85/100

PRC Builders has a clean sweep of five-star reviews, and owner Pat gets singled out for same-day emergency repairs and two-day roof replacements without upselling. With 25 reviews behind it, the record is shorter than the top two picks but consistent.

• Same-day response for emergency repairs
• Fair pricing with no upselling
• Full roof replacements finished in 1-2 days
• Owner-led communication on every job

Watch out: A smaller review count than the top picks, so it's worth confirming current availability before you commit.

Services: roof replacement installation, gutter services

★★★★★4.9 (41 reviews)score 84/100

Bay Restorations built its reputation solving roof problems other contractors gave up on, from traditional shingles to rubber and commercial systems, under crew lead Jessie. Customers report no leaks years after installation and thorough cleanup at the end of each work day, backed by a claimed 75-plus year operating history.

• Solves roofing issues other contractors couldn't fix
• No leaks reported years after installation
• Efficient crews that work full days
• Thorough daily jobsite cleanup

Watch out: One recent review flagged a missed estimate appointment.

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

★★★★★4.8 (45 reviews)score 78/100

Berkeley Exteriors has served Fairfield and New Haven counties out of Milford since 1992, and recent work under Chris and Anthony draws praise for fair pricing, clear communication, and 50-year warranties on materials. The team routinely pairs gutter and siding work with roof installs and handles insurance claim coordination.

• Pricing that beats competitor quotes
• Transparent communication and fair adjustments mid-project
• Clean jobsites and crews that work around your schedule
• 50-year warranties on roofing materials

Watch out: An older complaint, about 20 years back, cites unresolved window trim and warranty issues under prior leadership, separate from the strong recent reviews.

Services: metal roofing, roof inspection insurance, gutter services

★★★★★5 (11 reviews)score 72/100

This second A Plus Exterior listing shares the same Owens Corning Platinum Preferred status, and reviewers highlight its in-house custom fabrication and insurance claims handling. With only 11 reviews on this listing, treat it as an early-stage read rather than a full track record.

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

Watch out: Only 11 reviews on this listing, so the sample is small.

Services: roof replacement installation, gutter services, roof repair

★★★★★4.5 (13 reviews)score 67/100

Rick's Roofing and Siding is owner-operated with more than 20 years of local experience, and reviewers cite quotes that beat competitors on full tearoff and replace jobs, with permits and dumpster fees built into the price. Sentiment is mixed: strong marks on big projects, but some recent gaps in communication on smaller repair calls.

• Owner-operated with 20-plus years of local experience
• Quotes often undercut competitors on full tearoffs
• Permits and dumpster included in pricing
• Reliable follow-up on repair work

Watch out: Some reviewers cite slow communication on smaller repair jobs, plus one long-standing quality complaint.

Services: roof repair, gutter services

★★★★★5 (15 reviews)score 64/100

Advanced Building Solutions earns a clean 5.0 across 15 reviews for on-time work and fair pricing, but nearly all of that feedback covers kitchen and bathroom remodeling rather than roofing or gutters. It's included as a lower-confidence option until more gutter and siding-specific reviews come in.

• On-time project completion
• Quality workmanship noted by reviewers
• Clean jobsite practices
• Fair, straightforward pricing

Watch out: Most of the review history is about kitchen and bath remodeling, not gutters or siding specifically.

Services: gutter services, roof replacement installation, roof repair

★★★★★5 (6 reviews)score 67/100

Seal-Tite is a small, family-owned shop best known for a decade-long relationship maintaining 36 historic roofs in Black Rock, with Kim's metalwork and welding singled out by name. All six reviews are five-star, though that's a small sample to judge by.

• Decade-long client relationships
• Specialized metalwork and welding skills

Watch out: Only 6 reviews on file, so treat this as an early signal rather than a full track record.

Services: flat roofing commercial, metal roofing, gutter services

score 30/100moderate

Sears Heating and Air Conditioning shows up in Milford's gutters and siding results, but it has zero Google reviews, and its public service listings center on air conditioning, furnace, and heat pump repair rather than roofing or gutter work. Confirm directly that they still take on exterior jobs before requesting a quote.

• Listed as an active Milford-based contractor in this category

Watch out: No reviews yet, and its stated services are HVAC-focused rather than gutters or siding, so verify fit before reaching out.

Services: roof replacement installation, roof repair, gutter services · Price: moderate

score 26/100

T.kovalik Remodeling doesn't yet have enough reviews for a reliable sentiment read, and it carries the lowest composite score on this list. It's included for completeness in Milford's gutters and siding category, but there is little public track record to go on.

• Listed as a Milford-area contractor in the gutters and siding category

Watch out: No reviews on file yet, so ask for references or recent job photos directly before hiring.

Services: roof repair, gutter services