At Roofing & Siding of Cape Cod, we are the veteran-owned, fully licensed asphalt roofing contractors Holliston MA homeowners trust when they want the job done right without shortcuts. We back every project with a 50-year guarantee and offer up to $3,000 off on eligible projects — a concrete savings figure for any homeowner making a real budget decision. Get your free estimate today and find out exactly what your roof needs.
Holliston is an inland Middlesex County town with no coastal exposure, but it receives the full New England winter package without exception. Nor’easters deliver snow load that stresses ridge caps and valley flashing on every roof in town. Freeze-thaw cycling through late winter lifts shingle edges and loosens the seal strips that hold them down through repeated expansion and contraction. Poorly ventilated attics — common in Holliston’s older colonials and ranches — create the warm roof deck conditions that generate ice dam formation, forcing meltwater back under shingles at the eaves and into the structure below. Summer UV and heat then degrade the granule layer on aging asphalt shingles, exposing the underlying mat and reducing both weather resistance and energy performance season by season.
Holliston’s housing stock spans several generations, from 1960s split-levels and ranches to the colonials built through the 1990s, meaning roofs at very different stages of their service life exist throughout the same neighborhoods. The oldest unreplaced roofs are well past their replacement window and accumulating risk with every winter. The warning signs Holliston homeowners should watch for include granule loss collecting in gutters and downspouts after storms, curling shingles or cupping at shingle edges, cracking along ridge and valley areas, visible dark staining or moss growth indicating chronic moisture retention, and ice dam formation or water staining on interior ceilings in winter. Any combination of these signals warrants a roof inspection before the next season makes the scope worse.
The distinction between shingle types matters more in a Massachusetts climate than most homeowners realize going into a roofing decision. 3-tab shingles are flat, single-layer, and carry a lower upfront cost — but their 20–25 year design life and limited wind resistance make them the minimum acceptable option rather than the smart one for Holliston’s winter conditions. Architectural shingles — also called dimensional shingles — use multi-layer laminated construction, carry a 30–50 year design life, and are rated for wind resistance up to 130 mph. They perform significantly better through Massachusetts freeze-thaw cycles and snow loading, and their deeper shadow profile suits the traditional New England character of Holliston’s established colonial neighborhoods in a way that flat 3-tab panels simply don’t.
For most Holliston homeowners replacing a roof that’s 20 years or older, architectural shingles are the straightforward recommendation. We install asphalt shingles Holliston MA homeowners can rely on from GAF and CertainTeed — two of the strongest product lines available for New England performance and warranty backing. Every asphalt roofing installation we complete includes ice-and-water shield at all eaves and in all valleys — the non-negotiable protection layer against ice dam infiltration — plus synthetic underlayment across the full deck surface, heavy-gauge drip edge metal at rakes and eaves, and ridge ventilation evaluation to ensure attic thermal performance that extends shingle life over the long term. These are the installation components that separate a roof built to last from one that fails prematurely and quietly.
Our asphalt roofing Holliston MA service scope covers the full range of residential roofing needs. Full roof replacement includes complete tear-off to the deck, a thorough inspection of every section of sheathing, and replacement of any rotted or soft boards before new material is installed — no hidden surprises after the old roof comes off. New roof installation for additions and new construction follows the same standard. For targeted roof repair — missing or cracked shingles, failed chimney flashing, valley resealing, gutter apron repair — we address the specific failure without pushing an unnecessary full replacement. Every engagement starts with a free roof inspection and written findings so you know exactly what you’re dealing with before any decision is made.
Our 50-year guarantee matches the strongest warranty positioning in this market and backs every completed project. Combined with up to $3,000 off on eligible projects, asphalt roof replacement Holliston MA homeowners have been putting off becomes genuinely more accessible. As licensed roofing contractors Holliston MA clients can verify — MA License LIS #102600, HIC REG #170787 — we carry full insurance and meet every state requirement. Our veteran-owned commitment means we do the job completely and correctly, not just adequately. Get your free Holliston roof estimate today — no obligation, no pressure, just straight answers.
3-tab shingles are rated for 20–25 years under Massachusetts conditions. Architectural shingles carry a 30–50 year design life depending on the product line and installation quality. Proper attic ventilation, ice-and-water shield at eaves and valleys, and periodic roof inspection all extend service life meaningfully in Holliston's climate. Roofs at or past 20 years without documented replacement should be assessed — not assumed to have years remaining.
3-tab shingles are single-layer, flat-profile, and lower in upfront cost. Architectural shingles use laminated multi-layer construction, last significantly longer, resist higher wind speeds, and handle freeze-thaw cycling better. For most Holliston homeowners, the modest cost difference between the two systems is well justified by the lifespan, warranty, and performance gap — particularly on a colonial or ranch that will sit under that roof for another 30 years.
Isolated damage — a handful of missing shingles, one failed flashing point — typically calls for targeted asphalt roof repair Holliston MA rather than full replacement. Widespread granule loss, curling shingles across multiple roof planes, a system over 20–25 years old, or recurring leaks in the same area generally indicate that asphalt roof replacement Holliston MA is the more cost-effective long-term path. A free roof inspection gives you a written assessment specific to your roof's actual condition.
Yes, on every project without exception. Ice-and-water shield at eaves and in valleys is standard on all of our asphalt roofing Holliston MA installations — it is the primary line of defense against ice dam infiltration, which is one of the most consistent causes of interior water damage on Holliston homes through the winter months. This is not an optional add-on; it's a standard component of every installation we complete.
Asphalt shingles Holliston MA pricing varies based on roof size, pitch, system type selected, and the condition of the decking uncovered during tear-off. Most full roof replacement Holliston MA projects on a standard colonial or ranch fall in the $9,000–$19,000 range. We provide a detailed written estimate after every free roof inspection. Qualifying projects are eligible for up to $3,000 off. Schedule a free roof inspection for your Holliston home — the assessment is free and the estimate is in writing with no obligation.
Experience the difference across Boston and Greater Boston. Our commitment to excellence sets us apart.
Our team's skills ensure top-notch quality in every project.
We use eco-friendly materials for a greener future.
Tailored services to meet your specific needs.
Quality services at affordable rates.
A company with a commitment to integrity and excellence.
Decades of experience specific to Boston's New England climate.
Scott DicksonTrustindex verifies that the original source of the review is Google. Best company I’ve ever done business with. Great experience would recommend them over and over again. Susan McCarthyTrustindex verifies that the original source of the review is Google. We are very happy with our new roof! We knew we were in good hands as they had done a roof at our neighbors and done outside work at my sister’s house and both were very pleased with their work. Our experience was the same. They came when they said they were coming. The roof they installed was very professionally done and looks great. They cleaned up after themselves and were just great to work with all around. Dmitry, the president, was a pleasure to work with as well. He was very responsive to questions and very helpful throughout the process. I will definitely hire them again for any outside work we may need in the future. Henri Pierre SalleTrustindex verifies that the original source of the review is Google. Roofing and Siding of Cape Cod delivered an excellent roof replacement in two days from start to finish. The owner, Dmitry Labkovich, is very professional, attentive to detail, and accessible at all times. The installation crew was sensitive to customer requests. Clean up each day was thorough and complete. We are completely satisfied with installation of our new roof. Tom McTrustindex verifies that the original source of the review is Google. I don’t normally take the time to write reviews but the project Dmitry did for us is an exception. I obtained 8 quotes to replace a 25 year old roof and an existing skylight. My decision came down to Dmitry and another contractor. I choose to go with Dmitry based on three factors; his written proposal was excellent and included every detail of what he planned to do, his price was very competitive, I prefer to do business with the company owner when I have the option and I called four referrals that all had nothings but good things to say about his work. Dmitry is very easy to work with, he is very flexible about changes and add-ons and his crew is outstanding. We also added some siding work during the project and Dmitry responded to our needs immediately. I definitely intend to do more projects with him in the future and highly recommend you include Roofing and Siding of Cape Cod and Boston in your quoting process. You can be confident when Dmitry says it will get done, that exactly what he does. MarcTrustindex verifies that the original source of the review is Google. Overall they did a nice job on the roof work, however dealing with them throughout the project was extremely challenging. In fact one of the references they gave me when I was deciding said the same thing but I didn't listen. Anyway, once I made my final payment, they stopped servicing me. They failed to register my roof warranty!!!! VERY important if we ever need repairs and need coverage. They also took away all the extra shingles after they told me that they would leave an open bundle. It was their recommendation to use shingles from the same bundle in case a repair is ever needed, so it matches the roof. They did the same thing with the siding and didn't leave us any. Anyway, the roof/siding started at the end of September. The project didn't complete until November, and I am still tracking them down follow up with me and I keep getting the runaround. No shingles, no warranty. Disappointed. kim lavachTrustindex verifies that the original source of the review is Google. Thank you so much for doing such a fantastic job replacing so much of the trim on my mom's home (14 windows, both front vertical pieces, and both sets of angled pieces below the roof). Your company was able to complete the job quickly and professionally and the house looks brand new. The window trim had been in particularly bad shape and we couldn't be more please with the outcome. I highly recommend your services! Thank you. David FryxellTrustindex verifies that the original source of the review is Google. Fair price, friendly staff, and super quick turnaround. Thanks Dmitry and team! T LeonTrustindex verifies that the original source of the review is Google. Roofing and Siding of Cape Cod, LLC did a fantastic job replacing the siding on our home. The quality of the materials and craftsmanship were top-notch, and the team worked with real precision. Communication was clear the entire way through, and the project finished right on schedule. Couldn’t be happier with how everything turned out. David WoolsonTrustindex verifies that the original source of the review is Google. Recently moved my Dad into an older home that needed a new roof. Bill and his teams evaluated the underlayment and made the proper repairs, keeping us updated the entire time. At the completion of the project, the entire site wash thoroughly cleaned of debris. We are very please with the professionalism of this team. ErikTrustindex verifies that the original source of the review is Google. We recently had our roof replaced by Roofing and Siding of Cape Cod, and couldn’t be happier with the results. Dmitry Labkovich provided a detailed quote, explained every step of the process, and made sure the project ran smoothly from start to finish. The crew arrived on time each day, completed the work efficiently, and cleaned up thoroughly afterward. Our new roof looks fantastic and gives us peace of mind before the winter season. Great experience — highly recommend Dmitry and his team!Google rating score: 4.9 of 5, based on 155 reviews
See how we’ve transformed homes of all sizes and styles, and you’ll get an idea of the quality and craftsmanship that you can expect from Roofing & Siding of Cape Cod.




Real projects. Real results. See how we transform homes — one job at a time.
Contact us for a free estimate and start your journey towards a beautiful, durable home exterior.
Contact us for a free estimate and start your journey towards a beautiful, durable home exterior.