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Testimonials From Middlebury
We were amazed at the effort and proficient manner you and your crew showed.
Testimonial by Gloria C. from Middlebury, CT
Scott - you have the best group...
Testimonial by John F. from Middlebury, CT
Company Awards
Owens Corning Platinum Awards for Excellence 2019
This award recognizes excellence in overall system selling performance for America's #1 most trusted and recognized roofing brand. This... [Read more]
Select Shingle Master
Weathertite Systems LLC has achieved CertainTeed's highest credential and therefore is authorized to operate and represent itself as a SELECT... [Read more]
CertainTeed Award
Ranked Top 10 CertainTeed Installer in 2007... [Read more]
More Awards

Middlebury, CT Roofing & Siding Company

They were amazing. They did everything they said t......
Happy Customers Surrounding Middlebury, CT
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Dependable roofing contractor serving Middlebury, CT

Your roof needs to withstand the worst of Connecticut's weather, keeping you and your family safe during winter storms, rain, and wind. Ever since our beginning in 2002, Weathertite Systems, LLC has been successfully helping homeowners in the Middlebury area with all of their roof repair and roof replacement needs. We are an Owen's Corning Preferred, BBB-accredited roofing company, fully capable of taking on anything from general roof repair and maintenance to emergency roof repair and complete roof installation. When it comes to your home's exterior, we do everything from roof repair and roof replacement to siding installation, window replacement, and more!

No matter how prepared you might be, storm damage can strike your roof when you least expect it. If you have serious roof damage that needs immediate attention, Weathertite Systems, LLC offers emergency roof repair in Middlebury. We also provide general roof repair and maintenance such as roof leak repair, hail damage repair, wood rot repair, and more.

If you need a brand new replacement roof, we offer a lifetime warranty to guarantee long-term quality and weather protection! A new roof installation is an important investment that will keep your home safe for years to come, so it's important to choose the right style and material for your home. Our large selection of roof replacement types includes:

  • Asphalt shingles
  • Composite roofing
  • Flat roofing
  • Energy-efficient shingles
  • Wood shingles/shakes
  • And more!

Weathertite Systems, LLC is your expert in both residential and commercial roofing in Middlebury – no project is too large or small!

Your local deck and siding company in Middlebury, CT

Along with our industry-leading roofing services, Weathertite Systems, LLC also offers residential and commercial siding repair and replacement. While your siding may not seem like a big deal in your home's overall construction, the right kind of siding can actually make a significant difference in your home's energy-efficiency, weather resistance, and curb appeal. Whether you need siding repair for your current siding, a siding replacement, or a brand new siding installation, we have you covered! Our stylish and functional siding options include:

  • Aluminum siding
  • Vinyl siding
  • Fiber cement siding
  • Cedar siding
  • And more!

We also offer durable, weatherproof deck installation and deck restoration services throughout Hamden and nearby. Complete your deck or porch upgrade with beautiful, customized handrails that will provide both safety and aesthetic appeal to your outdoor living space.

Beautiful window replacements for your home

Are you ready to complete your home improvement project with gorgeous and durable replacement windows? Weathertite Systems, LLC uses performance tested, Energy Star rated materials to ensure the best energy-efficiency for your home. Say goodbye to your old, drafty windows that are difficult to open and close! We provide beautiful window installations in every style and material, such as:

  • Aluminum windows
  • Vinyl windows
  • Bay and bow windows
  • Double-hung windows
  • Casement windows
  • And more!

Gutter contractor providing Middlebury with gutter installation and more

Weathertite Systems, LLC also provides a variety of gutter services including gutter installation and gutter replacement services using a wide range of quality materials. We also are proud to offer some of the best gutter protection around with Gutter Helmet by Weathertite Systems. Gutter Helmet by Weathertite Systems lets you keep debris out of your gutters while still letting water in.

Weathertite Systems, LLC is the roofing expert and siding contractor that you can rely on for all of your home improvement needs in Middlebury, CT, and areas nearby. We offer free cost estimates on roof repair, roof replacement, siding installation, window replacement, and all other services – get yours today!

Case Studies From Middlebury
A customer noticed the roof and chimney were leaking. He called Weathertite Systems to inspect his home and fix the problem.
A customer wanted to replace his skylight located in the right main roof section on his home.
After the customer had skylights re-installed on the roof, he called the team to install gutter guards.
Job Stories From Middlebury, CT
Chimney Chase Cover & Pipe Cover Installation - Middlebury, CT

A customer in Middlebury, CT, needed the chimney chase cover replaced as well as the pipe covers, so they contacted Weathertite. Here's what we did for them:


To start the job we:

Removed the 2 existing pipe covers from the chimney 

Removed the existing chimney chase cover

Replaced any damaged sheathing with CDX plywood

Installed ice and water barrier

Installed a new, stainless steel, chimney chase cover

Secured the cover and re-installed the original chimney pipe covers

Sealed all needed areas with tripolymer sealant

Then we: 

Removed the pipe cover from the steel pipe

Installed a metal screen 

Re-installed the original pipe cover

To finish the job we:

Removed all debris


The customer was very pleased with the final results.

Removal of existing pipe cover - Middlebury, CT

The following was completed to a Middlebury residence:

First our team:

Removed the existing pipe cover from the chimney chase cover located on the rear of the home and saved it

Removed the pipe collar and discarded

Removed the chase cover and discarded

Next, we:

Installed ice and water barrier to the area

Installed a new, stainless steel chase cover to the area removed

Installed a new pipe collar to the area removed

To finish the job in Middlebury, we:

Sealed all needed areas with tri polymer sealant

Removed all debris

Chimney Repair in Middlebury

Once our associate guided John through the necessary steps of getting his chimney repaired, the job begun.  Our crew completed the following for John:

First we grounded the chimney down to the roof line.  After this, our crew blew out all the joints, re-pointed the chimney front, painted the wash cap with acrylic 60 for strength, applied a slurry coat, and waterproofed the entire chimney.  After these steps, we removed the roofing shingles down to the decking from around the base of the chimney, installed an ice and water barrier to the area, and installed new shingles of like style and color with new bibs, corners, step-flashing and lead counter-flashing.  To finish the job, we sealed the lead to the chimney with tri polymer sealant, and removed all debris.  

John was pleased with the service he received and the result of the job completed!

Shingle / Gutter Replacement - Middlebury, CT

After measurements were taken on Stephen’s home in Middlebury, the following was completed to his home in March of 2013:

  • Remove the shingles damaged by the tree branches
  • Cut the existing plywood decking back to the nearest rafters
  • Install 1/2” CDX, 4-ply plywood where removed
  • Install new ice and water barrier where removed or damaged
  • Install new felt paper in areas removed or damaged
  • Remove and replace all damaged rake metal
  • Remove and replace all drip edge metal
  • Remove and replace all damaged shingles
  • Remove and replace the damaged gutter on the complete rear of the home
  • Remove all debris

The above stated work was completed in one day and Stephen was happy with what was completed.  We were happy to accommodate his home repair needs.

Roof Installation- Middlebury, CT

Alex called Weathertite Systems looking to have his roof redone.  We sent out our project manager and Alex agreed to the free estimate our project manager came up with.

We did the following:

-          Strip the roof of the existing three layers.

-          Apply SA Modified Bitumen Roofing System

-          Replace any damaged sheathing

-          Apply ice and water barrier at eaves

-          Apply new aluminum edging to the complete perimeter of the roof.

-          Apply underlayment

-          Apply new vent pipe boots

-          Apply new roofing shingles

-          Apply new counterflashing on chimneys

-          Apply Ridgevent to ridges

-          Remove existing gutters and downspouts and discard.

-          Apply new Seamless Aluminum Gutter System

-          Apply new aluminum downspouts

-          Clean up daily and remove related debris from the premises.

Alex was very pleased with the work completed by Weathertite Systems

Gutter replacement - Middlebury, CT

Fortunately, when Jeff called our office in early 2012, we solved his damaged gutter problems only a couple weeks after!  After sending a company associate to his property in Middlebury, more details on when to begin were sorted out.  Measurements were taken and necessary concerns were addressed.  After all was said and done, a date was set to begin work and our crew arrived on time and prepared.  The following work was completed in January of 2012:

  • Removed the damaged gutter located on the front lower roof eave section on the home and discard
  • Remove the damaged section of leader on the downspout located on the front right section
  • Install a new, eggshell colored, 5” seamless gutter to the area removed
  • Install one new elbow and a section of leader to the existing downspout
  • Seal all endcaps and popout with tri polymer sealant
  • Remove all debris

Jeff’s property looked as if we were never there!  He was happy with how his new gutter system looked and thanks us for a job well done.  Our customer service is something we stand by, and we were happy to accommodate Jeff’s needs!

Roof Repair - Middlebury, CT

Early to mid-July of 2009-this is when Antonio B. contacted Weathertite with some roof work that he was interested in having done.  We set up an appointment for one of our sales associates to meet with him at his Middlebury residence.  Our sales rep. took necessary precautions and pointed out what Antonio should consider.  The work which was eventually completed includes:

  • Installed 3-2 foot pieces of white brake bent aluminum diverters to the 2 rakes and to the gutter located on the right rear roof section of the home. 
  • Removed the shingles down to the decking in a 6 x 6 area from the roof section above the rear rubber roof
  • Installed ice and water barrier to the area and new shingles of like style and color with new step flashing behind the fascia underneath the valley
  • Remove the shingles and flashing from around the base of the chimney located on the front main roof
  • Install ice and water barrier to the area and new shingles of like style and color with new corners, step flashing, and lead counter flashing
  • Sealed the lead to the chimney with try polymer sealant
  • Waterproofed the entire chimney.

Prior to all of this being completed, we ran through the details with Antonio before actually beginning.  As for the finished product, he was pleased! The newly updated roofing areas and chimney were very much to his liking. 

Siding Installation - Middlebury, CT

Nadar B. from Middlebury had contacted one of our office associates in late August of 2011.  The call was regarding the current siding on her home, and how it needed some work done.  We informed her that she was entitled to a free estimate, so we sent out one of our associates to get some measurements.  Nadar was ready to go with us by the end of the appointment, so a date was set to begin work.  Some of the work included:

  • Install new, white, smooth, brake bent, aluminum trimming to the area missing on the left gable end on the home
  • Back nail all the aluminum trimming located on all the gable ends on the entire home
  • Remove the vinyl siding from around the 4” louver located on the rear left section on the home and save
  • Remove the 4” louver and discard
  • Install a new, white, vinyl, J-block louver to the area removed
  • Install Tyvek tape to the perimeter of the J-block
  • Re-Install the original siding to the area removed

All debris were removed from the property once the job was complete.  Nadar was pleased with her new siding and thanked our crew for the job.  We were happy to accommodate her siding needs!  

Roof Installation- Middlebury, CT

Alexander called Weathertite because he needed a new roof.  We sent over our project manager to take a look at the work that needed to be done.  After the project manager assessed the property, he wrote up a free quote for Alexander.  Alexander signed the quote and we began work a couple weeks later.  Our work included:

  • Strip the roof of the existing two layers.
  • Apply SA Modified Bitumin Roofing System to the rear low slope section over the garage.
  • Replace any damaged sheathing.
  • Apply ice and water barrier at the eaves and valleys.
  • Apply new aluminum edging to complete roof areas.
  • Apply underlayment, 15 lb. felt paper.
  • Apply new roofing shingles.
  • Apply Ridgevent to the ridges.
  • Remove existing front main gutter and discard. 
  • Apply new Seamless Aluminum Gutter Standard 5”
  • Re-use the existing downspout and elbows.
  • Clean up daily and remove all job related debris from the premises when complete.
  • Clean all roofing debris from the gutters when complete.

Alexander was very satisfied with the work our Weathertite crew did at his home.  He did it right with Weathertite!

Gutter Instillation- Middlebury, CT

Steven called Weathertite Systems looking for a new gutter system to be installed.  His had been worn due to the harsh New England patterns.  We sent over or project manager to assess the job that needed to be done, and we wrote up a free quote.  Steven agreed to the price presented and was ready for our crew to get the work that week.  Our work included:

  • Remove the existing ice guards from the front fascia area of the home and discard.
  • The small screws from the ice guards are to be put back in the holes.
  • Remove the existing screws from the drip metal in that area and discard.
  • Install a new white, 5”, seamless, .032 gutters to the area removed with a new inside miter.
  • Install a new 3x4 downspout to the new gutter.
  • Apply Tripolymer gutter sealant where needed.
  • Remove debris.

Steven was very pleased with the work our team did on his home.  The new gutter system looked great and was very functional.  

Siding - Middlebury, CT

Mid-March, 2013, we received a call from a customer names Tom A. in regards to a small job that needed to be done to his home.  After explaining what he needed, we agreed to have our project manager take a look at his home to assess the actual job to be done. 

Tom went ahead and signed with us, which allowed us to complete the following job:

  • Remove the remaining aluminum trimming from the dormer located on the front main roof section on the home
  • Install new, white, brake bent, aluminum trimming to the area removed

We were accommodating to Tom’s needs, whatever they might have been, and made sure he was pleased with the work completed.  We also made sure to clean up all debris left, and remove them from the property.  

Gutter Replacement - Middlebury, CT

Steven P realized that the current gutters on his home were not suitable to withstand any more harsh weather.  He decided to give us a call just to see what could be done.  Gutter work and replacement is something we are known for, so calling us was no mistake!  After explaining the gutter situation on his home, Steven decided it was best to have someone come take a look at what needed to be done.  One of our reps took a drive out and gladly inspected the gutter issues that arose for Steven, and explained that all he needed was a mere gutter replacement to two thirds of his home.  

Steven signed with us and we started work in no time.  We finished the job in a day and guaranteed his gutters to last for a very long time.  Steven was pleased with the service we provided but even more with his new Weathertite gutter system!  

Work Requests From Middlebury, CT
Vicinity of Kentwood Ct in Middlebury
Water leak in chimney
Vicinity of Cambridge Court in Middlebury
You fixed our roof last september... we now have 2 broken shingles on the front at the bottom just above the gutter. can you please let me know cost to fix? thank you.
Vicinity of Steinmann Ave. in Middlebury
New roof & gutters
Vicinity of Saint Joseph Ave, in Middlebury
Looking for new siding and gutters. Thanks.
Vicinity of White Avenue in Middlebury