Roofing, Siding, WINDOWS & DOOR in Chester County, PA
Installations, Replacements & Repairs
Chester County is one of Pennsylvania’s most desirable places to own a home — and homeowners here expect their exterior work to match that standard. Dexteriors Roofing & Siding delivers it: GAF Certified, CertainTeed ShingleMaster roofing, siding, windows, doors, and gutter work across the county, from the historic core of West Chester to the newer communities around Exton and Downingtown.
Founded in 2023 by a team carrying 15+ years of combined exterior-remodeling experience, Dexteriors LLC is fully licensed and insured in Pennsylvania — a contractor that does the job right and documents every dollar of it.
Exterior services we provide in Chester County
Premium GAF and CertainTeed shingle systems sized and detailed for the large roof surfaces common on Chester County homes.
Durable vinyl and fiber cement siding in styles that suit Chester County’s range of architecture.
A new roof or full siding job is a five-figure investment. Here’s what you get with us:
Manufacturer-certified
GAF Certified, James Hardie and CertainTeed ShingleMaster, accreditations that signal a properly trained, vetted installer.
Transparent, itemized estimates
Detailed quotes with photos, so a major project comes with zero guesswork.
A 10-year Craftsmanship Guarantee
We stand behind every installation.
Financing up to $250k
Flexible options for larger-scope work.
One accountable team
The same crew and point of contact start to finish.
Towns and townships we serve in Chester County
We work throughout Chester County, including:
Tredyffrin Township, West Whiteland Township, East Whiteland Township, West Goshen Township, East Goshen Township, Uwchlan Township, Upper Uwchlan Township, West Bradford Township, Caln Township, Willistown Township, Westtown Township, New Garden Township, the Borough of West Chester, Phoenixville, and Coatesville.
Built for Chester County homes
Chester County is one of the fastest-growing and most affluent counties in Pennsylvania, and its housing reflects that — large custom homes with substantial, often architecturally complex roof surfaces, alongside preserved historic stone homes and a steady supply of newer development. Each presents a different exterior challenge.
The larger custom homes mean bigger roofing and siding jobs where material quality and proper installation genuinely matter — a poorly installed roof on a 4,000-square-foot home is an expensive mistake. The county’s many homes built in the development booms of the late ’90s and 2000s are now hitting the 20-to-25-year mark, which is exactly when builder-grade roofing fails and original windows start costing real money in lost efficiency.
Chester County’s rolling, open terrain also means homes here can catch more wind than tucked-in suburban lots, and the region’s freeze-thaw winters and humid summers work shingles, siding, and sealant hard. We inspect the whole exterior on the free consultation and give you an honest read on priorities.
Our Process
Free Consultation
We start with a detailed inspection and discuss your options.
Transparent Estimate
You’ll get a clear, upfront price with no hidden fees.
Professional Installation or Repair
Our skilled team uses only quality materials.
Final Walkthrough
We make sure every detail is done right before finishing.
Here's What Our Customers Think
EXCELLENT Based on 51 reviews Posted on Miguel Perez (mikepe111)Trustindex verifies that the original source of the review is Google. Dexteriors is amazing. Last year, Dexteriors built us a huge covered deck, with lights, ceiling fan and stairs to the backyard in about 1 month. They also replaced our old door to the backyard with a sliding door. We used them again this year to screen the deck to reduce the amount of bugs there. The price was very reasonable compared to the other 3 quotes we got from other places. Communication with the team is fantastic, they made the whole process very straight forward. Scheduling is easy and once they start building, THEY BUILD. Thanks to Matt, Rick and the rest of the Dexteriors Team! We will use you again for future projects!Posted on Greg NardiTrustindex verifies that the original source of the review is Google. This is the Second time I have used Dexteriors…..2024 I had them restore my Rear deck which was really in bad shape…. The used the good sound structure and reinforced with more footings and made this look like a Brand New deck. Now 2 years later I was so Impressed with their PREVIOUS WORK I CONTRACTED THE TO DO my ROOF/Gutters and Fascia…….not only their quality work, they treated me like a FREIND….. Brothers: KEVIN AND MATT …..GO WAY BEYOND TO MAKE SURE YOU ARE HAPPY NO MATTER WHAT ALL THROUGH THE PROCESS AND BEYOND. Just received a complimentary card to reserve a 1 year inspection. I am extremely picky when it comes to contractors as I have done extensive remodeling and was a Maintenance tech for over 40 years, So when I encounter A TOP QUALITY CONTRACTOR, I stay with them. If you have them come out you will see for yourself. YOU WILL NOT REGRET CONTRACTING THEM!!!!Posted on Lisa CooperTrustindex verifies that the original source of the review is Google. We had Dexteriors replace our roof, siding, gutters, and some windows. We are so Impressed by the way our home looks! It was a truly amazing experience! We had met with 5 different roofing companies before we selected Dexteriors. Dexteriors stood out above all of them. From our first meeting with Kevin Gilmore, we were impressed. He was so informative and thorough. The entire team was super professional and did impeccable work. The team worked from sun up til sun down. Their attentiveness to every detail was impressive. Kevin and Matt Gilmore were so patient and guided us through all of the decisions that needed to be made for our project. Kevin, Matt and their team have a very impressive work ethic. We could not be happier with the results of our project. Dexteriors was great!Posted on Amy S.Trustindex verifies that the original source of the review is Google. So happy we chose Dexteriors! We had a few companies come out and give us estimates and ideas. Honestly, I was put off by some of the other companies that came out (and I'd say we are pretty easy to please). Other companies were very pushy and didn't seem to listen to what me any my husband were envisioning. Then Dexteriors came out. Happy with them the first day we spoke to them, during the build, and after! They listened, they offered ideas based on our budget, had great communication through the whole process, very friendly workers, keep a tidy work space, and do BEAUTIFUL, HIGH QUALITY WORK with ATTENTION TO DETAIL. Thank you Dexteriors for building our wonderful deck!!! Just a couple of pictures attached. They constructed the trex deck, railings, two gates, two staircases, added/extended roof to go over it, installed gutters, installed a sliding glass door, added lights/fan and outdoor outlets. The pictures do not reflect how beautiful it is in person!Posted on ED CALTERTrustindex verifies that the original source of the review is Google. Matt & his crew at Dexteriors did a phenomenal job removing our two tier deck and replaced with Trex. We will definitely be using them for future projects.Posted on Andrea JohnsonTrustindex verifies that the original source of the review is Google. We couldn’t be happier with our experience working with Dexteriors. Before choosing a contractor, we interviewed multiple companies, and Dexteriors stood out immediately. Their quote was fair, clearly explained, and gave us confidence right from the start. Thank you to Kevin Gilmore for our first meeting and for making such a great impression, he represented the company beautifully. We hired Dexteriors to build a roof over our patio and a custom media wall using materials that I specifically chose, even though they weren’t the easiest to work with. Despite that, the team handled everything with skill and professionalism, and the craftsmanship shows in every detail. Thank you to Rick Michael for the excellent communication and for doing such an outstanding job. A special thank you to our project manager, Matt Gilmore, who was absolutely excellent. He was highly responsive throughout the entire project, and whenever I had a question or concern, he addressed it quickly and thoroughly. His communication and attentiveness truly instilled confidence and made the entire process smooth and stress-free. The crew worked incredibly hard, showed up consistently, and maintained a high level of professionalism from start to finish. We are thrilled with the final result and genuinely so glad we chose Dexteriors for this project. Highly recommend!Posted on Shelby LeightTrustindex verifies that the original source of the review is Google. Dexteriors Roofing and Siding are fantastic to work with! They are clear in their communication ( often not the case with contractors) and they got our job done within the promised time frame they said they would. Again another rarity in the industry. Would definitely recommend you contact Dexteriors for any and all of your exterior home needs!Posted on Adam WeinraubTrustindex verifies that the original source of the review is Google. Matt and his team at Dexteriors is excellent. Originally met Matt to do my primary bathroom and kitchen which we are absolutely in love with. We then hired him to replace all of the windows in our house. He did an excellent job there as well. Not only does he do great work, he does it at a fair price and won’t cut corners or stop till the job is done right. I could not recommend matt and Dexteriors morePosted on David RTrustindex verifies that the original source of the review is Google. We couldn’t be happier with our experience with Dexteriors! They replaced our deck and installed a rain escape system, and from start to finish they went above and beyond. The crew’s attention to detail was outstanding, and they made sure every part of the project was perfect before wrapping up. Their professionalism, workmanship, and genuine care for customer satisfaction truly set them apart. We highly recommend Dexteriors to anyone looking for quality work done right!Posted on Tom TraubertTrustindex verifies that the original source of the review is Google. After a tree took out our existing deck, I obtained 4 quotes to replace and improve it. Dexteriors offered a competitive price and had completed similar projects to mine (i.e., a 20X20-ft Trex deck with a 10X15-ft screen room). The quality of the work exceeded my expectations and we are quite pleased with the new "room" of the house. In-progress photo attached (just completed last week).Verified by TrustindexTrustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more
Frequently Asked Questions
Do you handle large custom-home roofs in Chester County?
Yes — larger, more complex roofs are routine for us, and proper installation on them is exactly what manufacturer certification ensures.
Are you licensed and insured in Pennsylvania?
Yes. Dexteriors LLC is fully licensed and insured in both Pennsylvania and New Jersey.
Is the estimate really free?
Yes, every estimate is free and comes with no obligation.
My development is about 20 years old — is it time for a new roof?
Often, yes — builder-grade roofs typically show their age at 20–25 years. A free inspection will tell you definitively.