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TRUSTED BY MIDDLEBURY, VT HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon96
    Verified roofing services reviews

Top-Rated Roofers in Middlebury - Updated Nov 2026

Avatar for Home Evolution Roofing LLC
Home Evolution Roofing LLC
4.7(
273
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairFlat, Foam or Single Ply Roofing - Repair+2 more

Serving Middlebury, VT and surrounding areas

Approved

Super Service Award Winner

In business since 2000

Free estimates

Warranties offered

"Serge and his crew did a very thorough and professional job in their demolition and removal of my badly-rotted and leaking rubber roof on a back addition of my house. They also fixed a couple of joist/rafters to solidify the roof frame, and then they installed new plywood decking along with an insulated layer prior to finishing with a new rubber surface. All debris was cleaned up from the job, and I'm very happy with the outstanding job they did. The crew arrived on schedule, and did all of their work in a timely and safe manner. I feel it was a very good value for the money, and I wouldn't hesitate to hire them again for further future work, thank you. Best Regards, Dave Gaba 432 Saratoga Rd. (Rt. 50) Glenville, NY"
ROOFING
ROOF & SIDING
ROOF & SIDING
Response time7 hrs
Response rate100%
4 neighbors recently requested a quote
Avatar for Big Als Roofing
Big Als Roofing
4.4(
22
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Middlebury, VT and surrounding areas

Approved

In business since 2003

Free estimates

Emergency services offered

"Fantastic! Alex was incredibly responsive throughout the preparation and installation process. I'm building an unconventional house, an Earthship, and it was an interesting challenge to bring together the original roof construction design, required updates, and the rubber roof requirements. Alex is always upbeat, patient and a pleasure to work with. Thank you!!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+25

3 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Stormwise Roofing
Stormwise Roofing
4.6(
88
)
Asphalt Shingle Roofing - RepairNatural Slate Roofing - RepairAsphalt Shingle Roofing - Repair - For Business+3 more

Serving Middlebury, VT and surrounding areas

Approved

In business since 2005

Free estimates

Emergency services offered

"I hired Northland Roofing last week to repair my chimney, re-joint my patio and walkways, and replace a section of my roof. Antonio, the owner of the company, offered me a very fair price and did a fantastic job on all the work completed. He even came back at my request to improve on one area, which without hesitation, just completed today. I am very pleased with the way he handled himself from the original estimate to completing the work to everyone's satisfaction. My roof looks great, and turned out even better than expected because he suggested he install a copper strip at the peak of the roof to prevent additional mold and mildew, which my roof was getting due to a lot of shade on my property. I would absolutely recommend Antonio and North Land Roofing for anyone who needs excellent roofing and masonry work done at their home. They were very efficient, professional, and extremely competitive with pricing as well. I will certainly hire him again when i need additional work done."
Siding
Response time5 days
Response rate98%
18 neighbors recently requested a quote
Avatar for Five Star Roofing
Five Star Roofing
4.6(
26
)
Asphalt Shingle Roofing - Install or Replace

Serving Middlebury, VT and surrounding areas

Approved

In business since 2022

Free estimates

Emergency services offered

"Five Star Roofing did a great job replacing my roof. Everything was on time and they did great with communication. Everything covered during removal and cleaned up. Done in 6 hours!!"
Setting up
Finishing
Finishing
Finished
11/12 pitch

+3

Response time9 hrs
Response rate94%
41 neighbors recently requested a quote
Avatar for DaBella - Burlington (Roofing/Windows)
DaBella - Burlington (Roofing/Windows)
3.8(
1,137
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+4 more

Serving Middlebury, VT and surrounding areas

Approved

In business since 2011

Free estimates

Warranties offered

We are the premiere home improvement company, with service and products that will keep you happy for years to come. \n \nOur customers receive unmatched warranties and exclusive products. We offer exclusive roofing, siding and window systems that are manufactured in America and installed by factory-trained installers, delivering the best possible result every time. \n \nDaBella Baths is our exclusive bath division, specializing in tub and shower conversions, bathtub replacement, walk-in showers and walk-in tubs. \n \nIf you want to work with a contractor who is passionate about service, committed to quality and determined to delight you, then DaBella is for you! \n \nWe're ready to turn your dreams into a beautiful reality. \n

Bath
Bath
Bath
Bath
Roofing

+16

18 neighbors recently requested a quote
Recommended by89%of homeowners
Avatar for ASAP Pressure Washing
ASAP Pressure Washing
4.6(
92
)
Roof - Clean

Serving Middlebury, VT and surrounding areas

Approved

Super Service Award Winner

In business since 2020

Free estimates

Small jobs welcome

"Cheerful, energetic and positive human beings are rare, but London was one and it was a pleasure to watch teamwork go so smoothly! . The work itself was performed by someone who clearly understood roofs; the gutters were pressure washed, and the dirt and root- filled downpours were dislodged and emptied of the content all in a cheerful manner. Lastly, three decks were cleared of the roof debris using water spraying with a lower pressure.. To me, the people, London and his 2 helpers were a pleasure to watch at work; very rarely have I witnessed that kind of positivity at work; it was inspiring!!"
Response time1 day
56 neighbors recently requested a quote
Recommended by82%of homeowners
Avatar for Vermont Construction Company
Vermont Construction Company
5.0(
1
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - RepairMetal Roofing - Install or Replace+26 more

Serving Middlebury, VT and surrounding areas

Approved

In business since 2014

Free estimates

Emergency services offered

Vermont Construction is a leading roofing and siding contractor, specializing in residential asphalt and standing seam roofs. We provide fast, reliable service with estimates delivered within 24 hours and most roofs completed in just one day. As one of the few Owens Corning Platinum Preferred Contractors in Vermont, we offer unmatched quality backed by a 50-year manufacturer warranty and a 10-year craftsmanship warranty, ensuring long-lasting protection for your home. Working with Vermont Construction is simple, efficient, and hassle-free.

Condo Development, Owens Corning Duration Architectural Shingle in Driftwood - South Burlington
Asphalt Shingle Roof Replacement, Owens Corning – Modern Farmhouse in Charlotte, VT
Vinyl Siding Install - Saint Albens, VT
Hyde Park Siding, Windows and Doors
Condo Development, Owens Corning Duration Architectural Shingle in Driftwood - South Burlington

+19

Response time2 days
Response rate100%
10 neighbors recently requested a quote
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Showing 1-10 of 104
Roofing FAQs, answered by experts

After you've chosen the best roofer for you, schedule an inspection and review the final contract. Your roofing company should be able to provide options for scheduling the work and a potential timeline for obtaining the permits and starting the job. Remember to always request everything in writing before work begins.

Most Cape Cod houses are two stories tall at the peak, although they’re considered one-and-a-half stories tall because the steep roof pitch cuts off a portion of the living space on the second story. Unless you raise the roof on your Cape Cod house to add a dormer, the interior rooms upstairs will lose some usable living space to the sloped ceilings.

You should plan on waiting as long as it takes for the roof deck to dry out completely if it gets wet. In most cases, this will take about 24 hours, but it could take longer if you have shading on your roof or cloudy weather after the rainfall that prevents the sun from drying the material.

The purchase price of 3-tab shingles is less than that of other material varieties, such as architectural shingles. However, 3-tab shingles generally last far fewer years than even the least expensive architectural ones. Other roofing types, such as metal or clay, also cost more than 3-tab shingles. However, if you plan to stay in your home for many years, the long-term cost of any of these options can compete with 3-tabs because of their longevity.

A spray foam roof costs an average of $6,000 to install, making it one of the most affordable flat roofing options available. Costs can increase if you have a complex roof design with many roof vents or have a roof that’s larger than average. While up-front costs are relatively low, keep in mind that ongoing maintenance and repairs tend to be more expensive than you’d see with other flat roof materials.

The Middlebury, VT homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.