Best Roofing Companies Near You in Westport, CT (2026)
Top Roofers in Westport, CT
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Flying Colors earns consistent praise from customers for their professionalism, transparency, and quality craftsmanship across roof replacements, gutter installations, and related work. Customers particularly appreciate the team's communication throughout projects—from detailed explanations of materials and options to step-by-step photo documentation—as well as their reliability in meeting tight timelines and handling challenging jobs efficiently. The company stands out for fair pricing, meticulous cleanup, and genuine integrity demonstrated by leadership like Nello, who combines sales expertise with hands-on roofing knowledge to build customer confidence in projects that represent significant investments.
"I cannot say enough good things about Flying Colors work, and specifically, Nello, Diego and Jorge. I'm always skeptical of something that I am not an expert on myself and employing someone else (what don't I know that I need to) and Nello took the time, genuinely, not only to inform me/educate me, but to also be consistent, present, and accessible throughout the process. Diego was exceptional in his work and with his crew. He was available to…" — Cindi H.
+1 203-918-8950
Premier Gutter Protection earns consistent praise for fast response times, professional workmanship, and competitive pricing. Owner Nick and his team are known for their reliability, punctuality, and thorough communication in addressing customer concerns from initial estimate through project completion. Customers consistently recommend them for quality gutter cleaning, leaf guard installation, and additional roofing services.
"Premier Gutter protection is absolutely fabulous ! Nick the owner is very high class and the team he has working are extremely courageous and knowledgeable. Don’t look elsewhere! If you want a fabulous job done, along with courteous staff, Nick and his staff are the place to go. The BEST!!!" — EW E.
+1 631-707-0663
Triple Crown Exteriors - Roofing and Siding
Triple Crown Exteriors, led by owner Kyle, earns consistent praise from customers for exceptional professionalism, clear communication, and meticulous attention to detail on roofing and exterior projects. Clients appreciate Kyle's hands-on oversight throughout each job, honest pricing, quick response times, and commitment to thorough cleanup and quality workmanship. The team is recognized for being reliable, respectful, and easy to work with, consistently delivering results that exceed customer expectations.
"We used Triple Crown Exteriors recently for a roof replacement and were extremely happy with Kyle and his crew. From the initial quick response for the estimate to the final review and cleanup, and all in between, Kyle was a pleasure to work with. He got us on his schedule within a few days after a snow storm caused leaking inside my home. He explained everything in detail on the job scope, did not put any pressure on us, and made it very…" — Shawn F.
+1 631-682-5572
Martino Construction Group earns consistent praise from customers for exceptional communication, reliability, and quality craftsmanship. Homeowners particularly appreciate the daily updates from team members like Heather and project managers who keep them informed throughout every phase of work, along with the punctuality and professionalism of the entire crew from initial consultation to project completion. Customers also value the company's problem-solving approach, fair pricing, and commitment to detail—with no corners cut—making them a trusted choice for bathroom renovations, kitchen upgrades, and larger projects like basement finishing.
"We retained Vinny and his team to build out a new finished basement, and renovate an existing guest bathroom. The experience -- from the start when they recommended an excellent architect for the project, to the on-time finish of the work -- was excellent. We've done many home renovation in the past, and have worked with a number of contractors, some more reliable and honorable than other; The Martino Group clearly exceeded our expectations on…" — Michael S.
+1 631-603-6518
Newhouse Restoration earns consistent praise from customers for their professionalism, expertise, and customer-focused approach to water damage and restoration projects. Clients specifically appreciate their prompt response times, thorough use of advanced drying and dehumidifying equipment, and clear communication throughout the process—with technicians taking time to explain their work and ensure complete moisture removal before repairs begin. The team is recognized for their reliability, organized work ethic, and ability to transform stressful situations into manageable experiences while delivering exceptional craftsmanship and workmanship.
"Josh, Ray and the crew were all amazing. From the very beginning when Josh came to assess our house, we knew we were in good hands. He was our 8th contractor to come and right away we felt at ease. He took time to explain everything and even offered to show us what he meant. Once work started everyone was professional, tidy and courteous. They took a stressful situation and made it bearable. The workmanship they did is amazing. The crawl space…" — Jessica G.
+1 631-604-8590
JIP Construction, led by owner Jose Alfonso, is renowned for exceptional craftsmanship and outstanding customer service. Customers consistently praise the team's professionalism, reliability, and meticulous attention to detail on paving, masonry, and landscaping projects, with many noting work completed ahead of schedule and within budget. Alfonso's responsive communication, hands-on involvement, and ability to deliver on promises—even through challenging weather conditions—have earned the company a strong reputation for quality work and dependable service.
"From start to finish J.I.P. Construction did an excellent job executing our vision. Within the same week after speaking, Alfonso (Owner) came down to give us an estimate and a detailed proposed contract of the work to be done, which was totally reasonable and in budget. He was clear, informative and always prompt even with the smallest updates. Alfonso was very much involved with the project and always kept us updated, a rarity to see nowadays.…" — Cecily P.
+1 516-410-0312
Guidice Contracting earns consistent praise from customers for exceptional craftsmanship, meticulous attention to detail, and professional execution across renovation projects ranging from kitchens and bathrooms to extensive fire damage restoration. Clients particularly appreciate Anthony's responsive communication, clear project timelines, organized planning, and ability to deliver results that exceed expectations while maintaining clean, respectful work environments. The company's reliability, trustworthiness, and seamless coordination with insurance companies and outside contractors have made them a trusted choice for repeat customers and referrals.
"Thank you Guidice Contracting for bringing my Pinterest picture to life!! My husband and I love how the bathrooms came out, they are absolutely beautiful! I will consistently give this company a 5-star rating as we have used them for prior projects. This time it was for two bathrooms. Every detail came out perfectly and any questions or concerns I had were always addressed. Equally important are all the other things that go along with the…" — Alda D.
+1 631-633-4876
Skyline roofing & siding
Skyline Roofing & Siding consistently delivers exceptional craftsmanship and transformative results, with customers praising the dramatic before-and-after improvements to their homes. Tom and his crew are known for their professionalism, responsiveness, fair pricing, and meticulous attention to detail—including thorough cleanup and daily punctuality. Customers particularly appreciate Tom's honest guidance, willingness to provide temporary solutions when needed, and commitment to quality backed by a 10-year warranty.
"I was looking for a roofing company after seeing leaks in the ceiling when it would rain outside. Honestly, I was nervous at first because I read reviews from other roofing companies and they were awful ...of course everyone has an opinion. My brother sent me the link for Skyline Roofing & Siding and when I read all of the positive reviews from this company, I decided to give it a try. Tom came and inspected my roof and showed me pictures of what…" — K. W.
+1 631-685-3039
Customers consistently praise Spartan Restoration for exceptional professionalism, responsiveness, and genuine care during stressful situations like floods, fires, and sewage backups. The team—led by Mike, Dan, Rob, and Bobby—is recognized for arriving quickly, explaining work clearly at every step, maintaining meticulous organization and cleanliness, and providing thorough documentation for insurance claims. Their combination of efficient execution, transparent communication, and respect for customers' homes has earned strong recommendations across multiple emergency restoration scenarios.
"Spartan Resto exceeded all my expectations. From the very first contact, Mike and his crew showed professionalism, speed, and most importantly, a genuine commitment to helping people. They arrived in record time, assessed the situation clearly, and got to work immediately. The team was extremely organized, clean, and detail-oriented. They didn’t just mitigate the damage efficiently; they also took the time to explain every step of the process,…" — Michael S.
+1 631-502-7580
Pappy's Ultimate Remodeling and Construction consistently earns five-star reviews for exceptional craftsmanship, competitive pricing, and reliable project completion on time and on budget. Customers particularly praise the team's professionalism, transparent communication throughout projects, and attention to detail—from daily WhatsApp updates to careful explanations of work and thorough cleanup. The company's personable approach and commitment to customer satisfaction have earned them strong recommendations for roofing, remodeling, and general construction work.
"We are very pleased with Pappy's Ultimate Remodeling and Construction. They do amazing work at an affordable price. They get here on time and do great work. Our work was extensive: they remodeled our kitchen completely, moved our laundry room and dining area by tearing down an exterior wall and lifting up a floor to make our breezeway part of the house. Renovated a full bathroom and half bathrooms. They did new cabinets, appliances, doors, and a…" — Mike B.
+1 631-710-9974
Why Hire a Local Roofer in Westport?
Local Climate Knowledge
Westport roofers understand Connecticut's specific weather patterns and choose materials built to last in local conditions.
Building Code Compliance
Local contractors know Westport's permit requirements and code standards, ensuring your repair passes inspection.
Faster Response Times
A local company can respond to emergencies quickly and follow up easily if issues arise after the repair.
Typical Roof Repair Costs in Westport
| Repair Type | Typical Cost Range |
|---|---|
| Minor Leak Repair | $150 – $400 |
| Shingle Replacement (small area) | $300 – $900 |
| Flashing Repair | $200 – $600 |
| Gutter Repair / Replacement | $150 – $500 |
| Section Repair (large area) | $1,500 – $5,000 |
| Emergency Repair | $500 – $1,500 |
| Full Roof Replacement | $8,000 – $25,000+ |
* Estimates only. Actual costs vary by scope, materials, and contractor. Get at least 3 quotes.
FAQ: Roof Repair in Westport, CT
Roof repair costs in Westport typically range from $150–$400 for minor leak repairs to $1,500–$5,000 for extensive section repairs. Emergency repairs can cost more. The exact price depends on the extent of damage, roofing material, roof pitch, and the contractor you choose. Always get 3 quotes before committing.
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