Best Roofing Companies Near You in Highland, MA (2026)
Top Roofers in Highland, MA
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Flynn Roofing is an owner-operated company known for exceptional craftsmanship, meticulous attention to detail, and honest, pressure-free customer service. Led by owner Stephen Flynn, who is consistently present on job sites, the team delivers professional, efficient work with thorough cleanup and reliable adherence to timelines and estimates. Customers particularly value the company's combination of competitive pricing, high-quality materials, and personalized follow-up care that extends beyond project completion.
"After receiving estimates from several roofing companies we landed on Flynn Roofing. While pricing was similar, Flynn stood out as small owner operated company. Engaging, but not pushy, they answered every annoying question we had. The owner was on site every day and checked to make sure we were happy as the job progressed. The result was transformational. The roof looks great and Steve Flynn came back the day after the job was done to…" — Janet
+1 617-479-3431
+1 617-201-3595
Commonwealth Roofing and Siding earns consistent praise for their responsive communication, efficient project management, and exceptional workmanship. Customers particularly appreciate owner Alex's accessibility and his team's professionalism—from quick emergency response to ice dam situations to thorough attention to detail and property protection during installations. The company also stands out for competitive pricing, fair quotes, and going above and beyond, such as completing work ahead of schedule or including unexpected work at no extra charge.
"⭐⭐⭐⭐⭐ Outstanding Roof Replacement Experience! I couldn’t be happier with my experience with Commonwealth Roofing and Siding. From start to finish, their team was professional, knowledgeable, and incredibly easy to work with. They took the time to explain the entire roof replacement process, answered all my questions, and made sure I felt confident every step of the way. The crew arrived on time, worked efficiently, and showed great attention…" — Mark A.
+1 800-672-7497
Dave brings exceptional craftsmanship and attention to detail to every project, from roof repairs to porch restoration, consistently delivering quality work that exceeds customer expectations. Customers consistently praise his professionalism, responsiveness, and fair pricing—he typically responds within an hour, provides transparent quotes, and often comes in under estimates. His combination of extensive knowledge, courteous communication throughout projects, and genuine care for his work makes him a trusted choice for both urgent repairs and long-term home improvements.
"I called Dave for a door frame repair. Within an hour, he was there to inspect the site and gave me options and quotes for the job! He is professional and courteous. His rates are very reasonable. Dave arrived promptly at the designated time and kept me informed of the progress. He cleaned up when the job was finished and had me inspect the area . I definitely will be using Dave again for all my carpentry needs!!" — Jeanne R.
+1 401-475-1447
Local Flow Restoration stands out for its professional crew, fast response times, and meticulous attention to detail on water damage and mold restoration projects. Customers consistently praise the company's clear communication, fair pricing, and comprehensive warranty coverage that provides peace of mind. The team's respectful approach to protecting customers' belongings and completing jobs efficiently has earned strong loyalty and repeat business.
"Great company with a professional team. They explained everything before starting the job. Warranty and pricing were both excellent. Highly recommend local flow restoration. Amazing people to work with trust me." — Jeremiah J.
+1 857-337-2202
Huerta Construction earns consistent praise from customers for their promptness, professionalism, and attention to detail across projects ranging from snow and ice dam removal to outdoor lighting installation. Clients appreciate their reasonable pricing, reliable scheduling, and willingness to go above and beyond the original scope of work. The team is particularly noted for their clear communication, timely follow-up, and ability to execute custom designs with precision.
"Huerta Construction did an outstanding job installing my Govee outdoor permanent lights. They were very professional throughout the entire process and executed the design I gave them perfectly. Their attention to detail and expertise really showed in the final result. Highly recommend their services!" — Yan X.
+1 508-383-3482
Optima Home Improvement, led by owner Leo, consistently delivers high-quality craftsmanship on basement finishing, bathroom installation, and structural projects while maintaining excellent communication and reliability throughout each job. Customers praise Leo's responsiveness, attention to detail, and ability to complete projects on time and within budget, while treating homes with respect and minimizing disruption. The team's efficiency, combined with Leo's personable approach to understanding client needs and keeping homeowners informed at every stage, has earned strong loyalty with multiple customers returning for additional projects.
"We have use optima Home improvement twice and plan to use Leo again. Our first project, we hired Optima Home Improvement to remove our bulkhead and construct an entryway for our basement, and we couldn’t be more pleased with the outcome. This project took a few days, and they communicated through the entire process. Our second project was the shower in our basement. We asked him to fix and waterproof the walls so that later on we could tile. I…" — Christine B.
+1 617-987-1995
Keenan Masonry
Keenan Masonry earns consistent praise for exceptional craftsmanship, prompt and professional service, and clear communication throughout projects. Customers particularly appreciate the crew's attention to detail, daily cleanup, fair pricing, and collaborative approach that makes clients feel involved in the design process. The team's reliability and courtesy have made them a top choice for masonry work, with clients enthusiastically recommending them for everything from walkways and steps to fireplaces and large-scale projects.
"Sean and his crew did an excellent job on my front walk way and steps. The quality of the work was top notch. The price was very fair for the work done. At all times, Sean and his crew were incredibly prompt, professional and courteous. They cleaned up incredibly well from all the work they did. I would hire Keenan Masonry again in a heart beat and recommend them to anyone looking for mason work in the area." — Steven R.
+1 508-408-0588
Vault Roofing earns consistent praise from customers for their knowledgeable and personable representatives who take time to thoroughly explain roofing needs and options in detail. Clients particularly appreciate the company's collaborative approach to budgeting, attentive communication throughout projects, and the friendly professionalism of both their inspection specialists and crew supervisors. The team's combination of expertise, trustworthiness, and customer-focused service consistently exceeds expectations.
"We are very happy with this company!!! James came to go over everything, and I mean everything. We had no questions for him at the end of our visit and he worked with us to stick within our budget. He was very friendly and knows his stuff! Our crew supervisor, Andrew was also great! He kept in constant communication and was also very friendly. They and the crew make their job look effortless with the best results. I can't say enough good things…" — tina B.
+1 774-545-8604
Skyway Exteriors earns consistent praise from customers for Tony's professionalism, responsiveness, and willingness to go above and beyond—from same-day emergency service for ice dams to thorough photo documentation of repairs and detailed explanations throughout the process. Customers particularly appreciate the company's reliability, fair pricing with no surprise costs, meticulous attention to detail, and exceptional cleanup work. The team's combination of efficient execution, honest communication, and genuine care for customer satisfaction makes them a trusted choice for roofing needs throughout New England.
"I had 3 companies come and give me estimates for a roof repair and skylight installation. I went with Skyway Exteriors for the incredible service they provided. Tony came and evaluated my roof and skylight. He took pictures and gave me a detailed written estimate of the work needed. I called him several times with questions and he was always patient and pleasant. He came and did the work in one day, again taking pictures and explaining what he…" — Beth L.
+1 508-272-6895
Why Hire a Local Roofer in Highland?
Local Climate Knowledge
Highland roofers understand Massachusetts's specific weather patterns and choose materials built to last in local conditions.
Building Code Compliance
Local contractors know Highland'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 Highland
| 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 Highland, MA
Roof repair costs in Highland 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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