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- About us · Leesburg, FL

The Leesburg roofing company behind this site

Pro Specialty Services is a state-certified roofing contractor in Eustis, 25 minutes from Leesburg, owned and run by Caleb Hutchinson since 2019. Here is who you are hiring and how we work.

- Who you are hiring

Pro Specialty Services

Owner
Caleb Hutchinson, licensed contractor
Office
3105 Kurt St, Eustis, FL 32726
Established
2019 · 7 years serving Lake County
Florida licenses
#CCC1335465 · #CCC1332012 · #CGC1538852 · #CRC1332909

- Free · no obligation

Request your free estimate.

★★★★★5-Star Google Reviews(352) 747-1164

If you are comparing a Leesburg roofing company against the others in your search results, start with the things you can check. Pro Specialty Services holds four Florida contractor licenses, carries liability insurance, has a 5.0 rating on Google from real customers, and was voted a 2025 Nextdoor Neighborhood Fave by Lake County neighbors. Our office is at 3105 Kurt St, Eustis, FL 32726, about 15 road miles and 25 minutes from central Leesburg.

We built this site because roof repair in Leesburg is a different job from a re-roof in a new subdivision. The city's housing stock is mostly 1980s and 90s, a large share of it in 55+ communities with their own approval boards, and a meaningful share is manufactured homes. That calls for a repair-first contractor who knows the neighborhoods, both permit offices, and the state rules that decide whether a roof gets patched or replaced.

Who you are hiring

Pro Specialty Services is owned by Caleb Hutchinson, a licensed contractor who still looks at the roofs himself. The person who inspects your roof is the person who writes the scope and stands behind it.

We are family-owned, established in 2019, and based in Eustis. We work across Lake County, with Leesburg, Fruitland Park, Lady Lake, Tavares and the US 27 South corridor as our core area. We do not claim to be the biggest roofer in Lake County; we aim to be the one whose paperwork, photos and warranty hold up.

Four Florida licenses you can look up

Every license number we advertise is verifiable on the state's site at myfloridalicense.com. Pro Specialty Services holds:

  • CCC1335465, Certified Roofing Contractor
  • CCC1332012, Certified Roofing Contractor
  • CGC1538852, Certified General Contractor
  • CRC1332909, Certified Residential Contractor

Certified, as opposed to registered, means the license is valid statewide, not just in one county. The general and residential contractor licenses matter on roofing jobs more often than you would think: when a leak has rotted fascia, soffit or a section of wall, the same licensed company can repair the structure instead of handing you off to a second contractor.

We carry liability insurance on every job. Ask for the certificate; we send it with the estimate. Unlicensed roofing activity rises after every named storm, so verify any bid against the state database and against the permit record at the building office before money changes hands.

Two named guarantees, in writing

Promises are only worth what is on paper, so ours have names and terms.

Leak-Free Promise. If our work leaks, we are on site within 48 hours and fix it at no cost to you. This runs for the whole length of your workmanship warranty. Call or text the owner; there are no claim forms, no service fee and no trip charge. It covers leaks caused by our installation; storm damage, other contractors' work and owner alterations are not workmanship. If it is unsafe to be on the roof within 48 hours, we tarp or dry it in first and complete the repair as soon as conditions allow.

Price-Is-the-Price. The number on your contract is the number you pay. The only common change order is rotten decking, at the per-sheet price written into your contract, and we photograph every sheet we replace. Any other hidden-condition work needs your written approval before we do it. No surprise dump fees, permit add-ons or "while we were up there" upgrades.

The full wording of both is on the guarantees page of the main Pro Specialty Services site.

The warranty: 10 years on replacements, 2 years on repairs

Pro Specialty Services gives a 10-year workmanship warranty on roof replacements paid cash or financed, transferable once to a new owner. Repairs carry a 2-year workmanship warranty on the repaired area, and all insurance-funded projects carry a 2-year workmanship warranty. Manufacturer material warranties are separate and are registered in your name at the end of the job.

Workmanship means the way the roof was installed: fastening, flashing, sealing, underlayment laps, ventilation. That is the part a contractor controls and the part that causes most leaks in the first years of a roof's life, which is why the warranty is on us and not only on the shingle manufacturer.

How we work on a Leesburg roof

  1. Free inspection within 48 hours of your request. We walk the roof, check the attic when there is access, photograph everything, and leave you a written summary. If the right answer is "it is fine, call us in two years," that is what the summary says.
  2. Written scope and price. The estimate lists materials by product name, the flashing and ventilation details, the per-sheet decking price, and the warranty terms. You can compare it line by line against any other bid.
  3. HOA or ARC paperwork. In Royal Highlands, Plantation, Legacy, Highland Lakes, Arlington Ridge and Pennbrooke Fairways, we prepare the approval submission before ordering material.
  4. The right permit office. Leesburg parcels inside city limits permit through the City of Leesburg Building Division; most of 34788 and much of the US 27 South corridor permit through Lake County in Tavares. We are registered with both.
  5. Installation and inspections. Pre-2002 homes get the code-required sheathing re-nail; every replacement gets the secondary water barrier the state requires; progress photos go to the inspector; the final inspection closes the permit.
  6. Clean-up and paperwork. Magnet sweep for nails, debris hauled, warranty documents and the permit closure delivered to you.

For storm damage, add one more step: we document the roof with photos and measurements and write a scope you can hand to your carrier. We are roofing contractors, not public adjusters. We do not file, negotiate or interpret your claim, and your insurer decides the outcome.

What we do not do

  • We do not offer anything of value for letting us inspect a roof or for filing a claim. Florida law forbids it, and it is bad business.
  • We do not recommend a replacement when a repair will hold. Repairs are most of what Leesburg homeowners call about, and the roof repair page explains how we decide.
  • We do not quote from satellite photos. Someone from our company stands on the roof before you get a number.
  • We do not hand off the inspection or the warranty. The company whose name is on the permit is the company that answers the phone in year nine.
  • We do not invent reviews. The reviews page shows every Google review under the reviewer's own name.

Verify us in five minutes

Before you let any roofer onto a Leesburg roof, spend five minutes checking them. Here is the checklist we would want you to run on us, in the order that catches the most problems.

  1. License lookup. Search each number above on the Florida Department of Business and Professional Regulation site. Confirm the status reads current and active, the name matches the company on the estimate, and the license class is roofing, not a handyman registration.
  2. Permit record. Both the City of Leesburg portal and the Lake County portal let the public search permits by contractor. A roofer who claims a long local track record but has no permit history in either system is telling you something.
  3. Certificate of insurance. Ask for the liability certificate issued directly from the carrier with your address listed as the certificate holder. Expired dates and photocopies are the two common tells.
  4. Corporate filing. Sunbiz, the state's corporate registry, shows how long the entity has existed and who the officers are.
  5. Reviews under real names. Open the Google Business Profile, not a screenshot on a flyer, and read the newest twenty.

When you call us, it also speeds things up to have your ZIP code, the HOA or park name, the approximate roof age, your insurance renewal date and any photos of stains, debris or lifted shingles. None of it is required.

- Check us out

Credentials you can verify

  • 2025

    Nextdoor Neighborhood Fave

  • 5.0★

    Rated on Google

  • FL

    State-certified contractor

    CCC1335465 · CCC1332012 · CGC1538852 · CRC1332909

  • 10 yr

    Written workmanship warranty

  • ✓

    Fully insured

  • 2019

    Locally owned · 7 years

- In writing, on every contract

Two promises we put our name on

Workmanship warranty: 10 years on replacements paid cash or financed, 2 years on repairs and on insurance-funded work. These two promises ride on top of it.

- Guarantee 01

Leak-Free Promise

If our work leaks, we are on site within 48 hours and fix it at no cost to you.

This runs for your whole workmanship warranty: 10 years on a replacement paid cash or financed, 2 years on a repair (the repaired area) and on insurance-funded work. Call or text the owner. No claim forms, no service fee, no trip charge.

Covers leaks caused by our installation. Storm damage, other contractors' work and owner alterations are not workmanship. If it is unsafe to work on the roof within 48 hours, we tarp or dry it in first and complete the repair as soon as conditions allow.

- Guarantee 02

Price-Is-the-Price

The number on your contract is the number you pay.

The only common change order is rotten decking, at the per-sheet price written in your contract (2026 shingle contracts: $125 per 4x8 sheet), and we photograph every sheet we replace. Any other hidden-condition work needs your written approval before we do it.

No surprise dump fees, permit add-ons or "while we were up there" upgrades. Anything you ask us to add is quoted in writing first, and you can say no.

- Ready when you are

Free Leesburg estimate, no obligation.

- FAQ

Questions Leesburg homeowners
ask us

Don't see what you're looking for? Give us a call - the owner picks up.

- Prefer to talk?

(352) 747-1164

Mon-Fri · 8am-5pm

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Yes. We hold two Florida Certified Roofing Contractor licenses, CCC1335465 and CCC1332012, plus a Certified General Contractor license, CGC1538852, and a Certified Residential Contractor license, CRC1332909. Certified licenses are valid statewide, so they cover Leesburg, unincorporated Lake County and every neighboring town. You can verify each one at myfloridalicense.com.
Our office is at 3105 Kurt St, Eustis, FL 32726. Central Leesburg is about 15 road miles and 25 minutes away by CR 44 and US 441. We schedule free inspections within 48 hours of a request and take storm emergency calls any time.
Workmanship means how the roof was installed: fastening, flashing, sealing, underlayment and ventilation. On a roof replacement paid cash or financed the workmanship warranty is 10 years, transferable once. On a repair it is 2 years on the repaired area, and insurance-funded projects carry 2 years. Manufacturer warranties on the materials are separate.
We inspect, photograph and document the damage and write a scope you can give your carrier, and we meet the adjuster on the roof if you ask. We are roofing contractors, not public adjusters: we do not file or negotiate claims, and we never offer anything in exchange for an inspection or a claim.
The inspection and the written scope come from the owner or a licensed representative of the company. Installation is done under our license and insurance, the permit is in our name, and the work is checked before the final inspection is called in.
Booking this week in Leesburg

Meet the contractor before you sign anything.

Free inspection, written scope, four verifiable licenses, two named guarantees. Call or book a time that works for you.

5-star ratedLicensed & insured