Verified record
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Leland Siding, Roofing & Windows. Use it to sanity-check bids, then get the real number in writing.
Estimated range
$4,000 – $11,000
Typical exterior project around $7,500
Leland Siding, Roofing & Windows is a Medway, Massachusetts contractor built around exterior remodeling — the business homeowners call for a full re-siding, a one-day roof tear-off and reshingle, or a run of replacement windows. The company says it has been family-owned and operated since Tony Leland founded it in Medway in 1990, and it holds an active Massachusetts home improvement contractor registration under that name. The Google reviews back that up with detail rather than just star counts: 61 ratings average five stars, and the write-ups keep landing on the same specifics — Tony walking homeowners through the quote personally, a crew that can strip and reshingle a full roof in a single day, and a jobsite that's clean and quiet by the time they leave. That pattern holds across six years of reviews, from 2022 through this year, without a negative one in the mix. Several reviewers say the finished trim and detail work covered more than the original quote described. Repeat business shows up too: one reviewer had their siding done and came back years later for a roof, and another's 2019 siding and window job led to a 2025 reroof when it came due. The company's own site lists a specific service area — Medway plus roughly a dozen nearby Metrowest towns, including Framingham, Franklin, Holliston, and Wellesley — worth checking if you're outside that footprint. Alongside siding, roofing, windows, gutters, and doors, it also advertises custom home design-build work, though the reviews on file are almost entirely about exterior remodeling rather than ground-up construction. For an aging roof or worn-out siding, this is a contractor with a long, consistently positive history on exactly that kind of job — the one thing worth nailing down before signing is precisely what the quote covers, since more than one customer found the finished scope ran ahead of what was written down.
I've used Leland multiple times and always have a great experience and find the work to be top-rate.
Tony and team do great work. We had Leland replace 30 year old wood siding and original windows on our home. Given the age, we had some rot issues which Leland were very thorough in finding and replacing. Even with the additional repairs needed, the team finished on time and accommodated our vacation schedule. Workmanship is of high quality. The siding installation was fast and the team took their time with the detailed trim we wanted to give the house character. Tony was very responsive throughout the whole project to answer any questions that we had. Pricing was very reasonable compared to all other estimates we received for the project and we never felt pressured as we did with some others. We are very happy with the final results and plan to use Leland again for any roofing or siding needs.
Leland replaced the sliding on our house as well as installing new sliding glass doors on our sunroom. Tony's quote understated the details of the siding work, while he quoted what seemed to be a basic siding installation the actual work surprised us with the added detail work that they did. The style of the corner trim, and the extra trim details around all of the windows made for a surprising impression. His work teams were on time and cleaned up well after each day's work. Also, the window installation didn't stop with just the carpentry work, all of the stickers were removed and the windows were cleaned so that we just got to walk into our sunroom and enjoy the new windows.
Had my home done with beautiful vinyl siding
Tony and his crew delivered everything as promised. His crew worked straight through a heatwave! They were amazing. We had all the siding replaced along with some windows, all the gutters, soffits and shutters! We are so happy that our 75 yr old house looks brand new! Don't hesitate to hire Tony Leland Siding...he's the best!
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Certified attributes are verified against the public registry. Others are the business's own statement.
1 change recorded — last scanned Sep 5, 2026.
Custom frameless shower doors4.9
Broad remodeling scope3.3
Price held firm5.0
Honest diagnosis over upselling repairs5.0
Fast response4.2