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Roof repair · Leesburg, FL

Roof repair in Leesburg, FL done right

A state-certified Lake County roofing contractor for Royal Highlands, Plantation, Scottish Highlands, the Haines Creek side and every ZIP in between. Free inspection, written findings, repair first when a repair is the honest answer.

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★★★★★5-Star Google Reviews(352) 747-1164
5.0
Google rating
Real reviews, never invented
10yr
Workmanship warranty
On replacements, transferable once
48h
Estimate turnaround
Mon-Fri, typically sooner
FL
State-certified
#CCC1335465 · #CGC1538852

Roof repair in Leesburg, FL is a different job than it is in a brand-new subdivision, and this site is built around that difference. Pro Specialty Services is a Florida-certified roofing contractor based in Eustis, about 25 minutes east, and most of what Leesburg homeowners ask us about is a roof that is somewhere between 18 and 45 years old: a lifted shingle field in Royal Highlands, a cracked pipe boot in Highland Lakes, step flashing that finally gave up on a 1970s ranch off CR 44, a seam on a manufactured home near Lake Griffin.

The city's housing numbers explain why. The median Leesburg home was built in 1985, more than half of the housing stock (56.8%) predates 1990, and 9% of homes inside the city limits are manufactured, with far more in the 55+ parks along US 27 South and US 441 that sit just outside the city line. That is a lot of roofs in the exact age range where small failures turn into ceiling stains.

So we lead with repair. We inspect for free, photograph what we find, explain it in plain language, and tell you whether a targeted repair, a leak fix or a full replacement is the right call. Every repair carries a 2-year workmanship warranty; every replacement carries a 10-year workmanship warranty. Manufacturer material warranties are separate and come with the product you choose.

What roof repair in Leesburg actually looks like

Most calls we take from Leesburg fall into a handful of patterns, and knowing which one you have tells you a lot about the fix.

  • Wind-lifted or missing shingles after an afternoon storm or a named system. The 2021 Fruitland Park event (52-knot gusts, documented shingle and soffit damage on several homes) is a typical example of the kind of weather that peels a field of 3-tab shingles without touching the house next door.
  • Pipe boots and vent flashings that have split in the sun. Neoprene boots on roofs from the late 1990s and early 2000s are now 20 to 27 years old, and they fail long before the shingles around them do.
  • Step and counter flashing at walls and chimneys on older homes in Palmora Park, Silver Lake and the ranches north and west of downtown, where the original metal has been caulked over three or four times.
  • Nail pops, exposed fasteners and rusted ridge vents on homes from the 1990s building wave in Highland Lakes and the earlier Plantation phases.
  • Seam and fastener leaks on manufactured homes, which we handle on the mobile home roofing page.
  • Soffit, fascia and drip-edge rot where gutters have overflowed for years. Leesburg's normal rainfall is 43.78 inches a year, with June alone averaging 6.98 inches, so a clogged gutter does real damage quickly.

Each of these is repairable when caught early. The roof repair page walks through what each fix involves, what we check around it, and how we decide when a repair is no longer worth your money.

Leesburg roofs by age: what fails and when

Leesburg grew in waves, and each wave left a different roof behind. This is the rough map we carry in our heads when we pull up to a house.

BuiltWhere you see itWhat usually fails first
1947 to 1970sSilver Lake, Palmora Park, the ranches around downtown and off CR 44Step flashing, valleys, rotted plank or thin decking, multiple layers of old roofing
1980 to 1992Scottish Highlands, Pennbrooke Fairways, first Plantation phasesOriginal 3-tab shingles past their life, pipe boots, drip edge, sheathing nailed to the old schedule
1990 to 1999Highland Lakes, mid-Plantation, Legacy's first streetsNail pops, ridge vent rust, granule loss, early architectural shingles curling
1999 to 2008Royal Highlands, Legacy of Leesburg, Arlington Ridge's first sections, late PlantationBoots and sealants at 20+ years, skylight flashing, roofs now hitting the 15-year insurance threshold
2010 onwardArlington Ridge later phases, Lake Denham Estates (2021+)Mostly storm damage and installer defects; repairs, not replacements
Any yearHawthorne, Mid Florida Lakes, Lake Griffin Harbor, Lakeside Village, Coachwood Colony, Spanish VillageMetal seams, fasteners, coatings, roof-over condition

The age of your roof also matters to your insurer. Under Florida Statute 627.7011(5), a carrier may not refuse to write or renew a policy solely because a roof is under 15 years old. Once it passes 15, an inspection showing at least five years of remaining useful life is what protects you, and licensed roofing contractors are among the inspectors the statute names. Our free inspection is where that conversation starts.

Every roofing service we offer in Leesburg

This is a repair-first site, but the full list is here because the honest answer is sometimes bigger than a patch.

  • Roof repair: leaks, shingle replacement, flashing, boots, vents, soffit and fascia, storm patches, with a 2-year workmanship warranty on the repaired area.
  • Roof leak repair: finding the actual entry point, not just the stain, and stopping it the first time.
  • Storm damage roof repair: emergency tarping, photo documentation and a written scope after wind, hail or a fallen limb.
  • Roof replacement: architectural shingle or metal re-roofs with the Lake County re-nail and secondary water barrier done to the letter, and a 10-year workmanship warranty.
  • Metal roofing: standing seam and exposed-fastener panels, metal repairs and coatings, including over manufactured homes.
  • Mobile home roofing: roof-overs, metal and silicone coatings for the 55+ communities on both sides of the city.
  • Free roof inspection: photos, a written summary, and straight answers about whether anything needs doing at all.

Financing is available on replacement and metal projects; the financing page explains how to see the options. Repairs are usually simple enough that nobody needs it.

Why hire a state-certified Lake County contractor

Florida licenses roofers at two levels. A registered contractor can work only in the local jurisdictions that registered them; a certified contractor is licensed by the state to work anywhere in Florida. Pro Specialty Services holds state certifications as a roofing contractor (CCC1335465 and CCC1332012), a general contractor (CGC1538852) and a residential contractor (CRC1332909). You can look all four up on the Department of Business and Professional Regulation site in about a minute, and we would rather you did.

Why it matters on a Leesburg roof specifically:

  • Permits are not optional. Florida Statute 553.79 requires a permit for roof work, and both the City of Leesburg and Lake County enforce it. An unpermitted repair or re-roof becomes your problem at sale time and at claim time.
  • The Lake County re-nail rule. Any detached single-family home built before March 1, 2002 that gets a new roof must have its sheathing re-nailed with 8d nails at 6 inches on center. That covers Scottish Highlands, Pennbrooke, Highland Lakes and most of Plantation. We photograph it for the inspector; it is not a surprise upcharge.
  • Wind design. Leesburg sits in Lake County's 130-140 mph design-wind band. It is not a high-velocity hurricane zone and not in the wind-borne debris region, which means some coastal retrofit requirements simply do not apply here, and a contractor who knows that will not sell you work the code does not ask for.
  • Insurance. We carry liability coverage on every job. Ask for the certificate. Anyone who hesitates is telling you something.

More about the company, the owner and how we work is on the about page.

Two permit offices, one city name

This trips up homeowners and plenty of out-of-area roofers. A Leesburg mailing address does not mean a Leesburg building permit.

  • Inside the city limits (most of 34748, including downtown and the west and south sides; the city line also takes in some of the US 27 South communities, which we confirm parcel by parcel): permits come from the City of Leesburg Building Division, 501 W Meadow St, (352) 728-9700, Monday to Friday 8:00 to 4:30. Applications go through the city's online permitting portal, and the contractor has to be registered with the city first.
  • Unincorporated Lake County (most of 34788, the Haines Creek and Lake Griffin side, Scottish Highlands, the big manufactured-home parks, and pockets along US 27 South outside the line): permits come from the Lake County Office of Building Services, 315 W Main St in Tavares, (352) 343-9653. Residential re-roofs there are auto-issued online, which usually means a faster start.

We are registered with both, we pull the permit in our name, and we schedule the final inspection. If the job cost exceeds $5,000, Florida law also requires a Notice of Commencement to be recorded before the first inspection; we handle that too. The service area page lists which office covers which neighborhood.

Storm history Leesburg roofs have already lived through

When we say a roof has "been through a few storms," these are the storms. Hurricane Irma in September 2017 produced a 69 mph gust at Leesburg International Airport, 8.18 inches of rain at the airport and 10.13 inches at a gauge a few miles northwest. Hurricane Ian in September 2022 gusted to 56 mph here. Hurricane Milton, on October 9 and 10, 2024, is the one most Leesburg roofs still show: the National Hurricane Center lists a 72-knot (about 83 mph) gust at the airport and 8.89 inches of rain, Lake County logged 285 affected structures (216 minor, 66 major, 7 destroyed), and 108,268 of the county's 201,960 electric customers lost power, including 18,972 on Leesburg Electric. No tornado was confirmed in Lake County from Milton; the damage was straight-line wind and water.

Between the named storms, ordinary Central Florida weather does steady work. NOAA's storm database shows 50-knot-plus wind at Leesburg on March 30, 2021 (the same day Okahumpka took inch-diameter hail), April 25, 2023 and May 18, 2024. Over 1950 to 2020 Lake County recorded 61 tornadoes, 103 hail reports and 132 severe-wind reports, peaking in April, May and June respectively. Florida also leads the country in lightning density.

What that means for you: a roof installed before Irma has now taken three named hurricanes plus seven summers of thunderstorms. If it has never been inspected since, the storm damage page explains what to look for and how we document it.

How the free inspection works

You call or book online. We confirm a window, usually within 48 hours on weekdays. On the day, one of us walks the roof (or inspects from a ladder and the attic if the surface is unsafe), photographs every penetration, valley, flashing and soft spot, checks the attic side of the decking for staining, and looks at gutters, soffit and fascia from the ground.

Tell us anything you have noticed, even if it seems unrelated: a musty smell in a bedroom closet, discolored insulation, daylight through the attic boards, a sagging gutter run, nails or granules at the downspouts, squirrels in the soffit, a dark streak that appears only after a northeast wind. Those clues often point straight at the entry point. Steep, two-story or wet roofs we inspect from the ladder, the attic and binoculars rather than walking them, which protects both the shingles and us.

Then you get a short written summary with the photos, and one of three answers:

  1. Nothing needs doing. This happens more than people expect, and we will say so.
  2. A repair will hold. You get a written repair price with the scope spelled out and a 2-year workmanship warranty on the repaired area.
  3. A repair is throwing good money after bad. You get a written replacement price with the decking terms in the contract, a 10-year workmanship warranty, and the option to see financing.

There is no obligation and no sales pitch at the door. If you are in a 55+ community with an architectural review committee, we prepare the paperwork for the ARC. If you need a 4-point or wind mitigation inspection for insurance, those are separate paid reports; the inspection page explains the difference so you order the right one.

Roof terms you will hear on your inspection

We try to explain findings without jargon, but a few words come up on nearly every Leesburg roof and it helps to know them before we hand you the photos.

  • Decking or sheathing: the plywood, OSB or (on older ranches) tongue-and-groove planks the roof is nailed to. Soft, delaminated or blackened decking is the single biggest cost variable on any job.
  • Underlayment: the felt or synthetic membrane between decking and shingles. Modern Florida re-roofs add a peel-and-stick secondary water barrier, which is what keeps wind-driven rain out when shingles lift.
  • Drip edge, starter strip, rake and eave: the metal and shingle courses along the edges. Missing drip edge is why fascia rots.
  • Valley, hip and ridge: where slopes meet. Valleys carry the most water; open metal valleys outlast closed-cut shingle valleys in heavy rain.
  • Step flashing, apron, counterflashing, kickout and cricket: the bent metal that seals walls, chimneys and dormers. Caulk is not flashing, no matter how much of it a previous handyman used.
  • Pipe boot, collar, goose-neck and off-ridge vent: the penetrations. Sun-cracked neoprene and rusted turbine bases are everyday Leesburg leaks.
  • Granule loss, cupping, clawing and blistering: the ways asphalt shingles show their age. Algae streaks and lichen are cosmetic until they lift the tabs.
  • Galvalume, gauge, Kynar and clip: metal roofing words covering the steel, its thickness, the paint finish and how standing-seam panels attach.
  • Elastomeric, silicone and acrylic: the coating families used on manufactured-home and low-slope roofs; they are not interchangeable.

When you call, it helps to have your ZIP code, the HOA or park name, the approximate roof age, your insurance renewal date and any photos of stains or debris. None of it is required; all of it speeds up the written summary.

Our two written promises

We put two promises in writing on every Leesburg contract, and they are the same on a one-boot repair and a full re-roof.

Leak-Free Promise. If our work leaks during the workmanship warranty, we are on site within 48 hours and fix it at no cost to you. No claim forms, no service fee, no trip charge. If it is not safe to work on the roof within 48 hours, we tarp or dry it in first and finish as soon as conditions allow. This covers leaks caused by our installation, not storm damage, other contractors' work or owner alterations.

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

Read the full wording on the about page or on the main site's guarantees page, then read what people who hired us actually wrote on the reviews page. Every quote there is a verbatim Google review under the reviewer's own name.

- Ready when you are

Free Leesburg estimate, no obligation.

- Google reviews

What homeowners say

  • ★★★★★

    “Caleb and his team did an amazing job with our roof repair”

    Caleb and his team did an amazing job with our roof repair. Quick to respond. Great communication. Extremely knowledgeable. Completed the job in a timely manner. Great attention to detail. Highly recommend!!!
    Karen Zuchowski · Google · October
  • ★★★★★

    My experience Caleb with Pro Specialty Services was outstanding very professional great price and very knowledgeable about all aspects of roofing for my particular project I would recommend him for all your Roofing and General Repair needs
    Rod Johnson · Google · September
  • ★★★★★

    “The attention to detail really shows”

    We couldn’t be happier with Pro Specialty Services! They took what was basically an unusable porch and completely transformed it into a beautiful, functional space that we now use for exercise, recreation, and watching nature. We had a serious water problem where rain would literally create a waterfall between the door from our house and the porch. Caleb figured it out, fixed the issue, and improved the pan roof so it actually does its job now! They went far beyond just fixing the water issue. They removed the old paneling, treated the mold, replaced rotten supports, and completely redid the exterior and interior walls. The old jalousie windows that were on every wall of the porch were replaced with beautiful, functional windows and solid wall sections. They also replaced the ceiling tiles and rusted ceiling rails, upgraded the old fluorescent lights to flat-panel LEDs, and replaced the exterior door with one that actually closes, locks, and has a proper threshold. He even worked to create a custom vent opening for our portable AC/dehumidifier, which allows us to keep the porch at a comfortable temperature and protect the things we have stored out there. They also repaired a deteriorating soffit on the front of the house and did a great job making all the new materials blend with the existing house. The attention to detail really shows. Caleb was fantastic throughout the entire process. He kept me involved with material selections, checked in regularly, answered all my questions, and genuinely cared about making sure we were happy with the finished product. The crew was professional, respectful of our property, and fun to have around. They even came back and put our car tent back up after we had to move it for access to the backyard. They cleaned everything up when they were finished, too! We went from having a porch that was basically just a storage area exposed to Florida’s heat, humidity, and rain to having a comfortable, usable extension of our home. Pro Specialty Services didn’t just fix our porch, they completely transformed it. We absolutely love the finished space and would highly recommend them!
    Candice Whitford · Google · August

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Licensed, insured, local

  • 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

- Financing available

Financing available on your roof

Financing is available for qualified homeowners through a third-party lender and is offered with every estimate. Details on the main Pro Specialty Services site.

- Service area

Roofing across Leesburg

Every neighborhood in Leesburg (ZIP 34748, 34788, 34749) plus the towns around it, from our office in Eustis.

Downtown Leesburg
Silver Lake
Royal Highlands
Plantation at Leesburg
Legacy of Leesburg
Arlington Ridge
Pennbrooke Fairways
Hawthorne at Leesburg
Lake Griffin
Haines Creek
Highland Lakes
Scottish Highlands
Lake Harris Shores
Palmora Park

Also serving: Fruitland Park · Lady Lake · Tavares · Okahumpka · Yalaha · Eustis. All Lake County service areas

Office
3105 Kurt St · Eustis, FL
(352) 747-1164

- FAQ

Questions Leesburg homeowners
ask us

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(352) 747-1164

Mon-Fri · 8am-5pm

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Repair is the first answer we look for. Most Leesburg calls are a leak, a wind-lifted section, a split pipe boot or rotted fascia on a roof that still has years left, and a repair with a 2-year workmanship warranty is the right fix for those. We only recommend replacement when the roof is past its life, when damage exceeds what the 25% rule allows us to patch, or when repairs would cost more than they save.
If you are inside the city limits (most of ZIP 34748) the permit comes from the City of Leesburg Building Division at 501 W Meadow St, (352) 728-9700. If you are in unincorporated Lake County (most of 34788, Haines Creek, Scottish Highlands, the large manufactured-home parks and parts of the US 27 South corridor) it comes from the Lake County Office of Building Services in Tavares, (352) 343-9653. We are registered with both and pull the permit for you.
Age alone is not the test; condition is. A 22-year-old architectural shingle roof in Royal Highlands with one failed boot is a repair. A 22-year-old 3-tab roof with granules in every gutter and shingles that crack when lifted is not, because every repair will damage the shingles around it. The free inspection photos make the call obvious in most cases, and we tell you which side of the line you are on.
Your carrier decides that, not us. What we can do is inspect, photograph and write a scope that describes exactly what is on the roof, and meet the adjuster on site if you file. We are roofing contractors, not public adjusters; we do not file or negotiate claims, and we never tie any offer to a claim or an inspection. For roofs past 15 years, Florida Statute 627.7011(5) lets you use an inspection showing five or more years of useful life, which is often the document that matters most.
Free estimates are typically booked within 48 hours on weekdays. Active leaks and storm emergencies go to the front of the line, and you can call the number at the top of this page any time after a storm. Our office is at 3105 Kurt St in Eustis, about 15 road miles and 25 minutes from most of Leesburg, so the drive is never the holdup.
Repairs carry a 2-year workmanship warranty on the repaired area. Full replacements carry a 10-year workmanship warranty, transferable once to a buyer. Both include our Leak-Free Promise: if our work leaks, we are on site within 48 hours at no cost. Manufacturer warranties on shingles, metal panels and coatings are separate and depend on the product you choose.
Yes. Royal Highlands, Plantation at Leesburg, Legacy, Arlington Ridge, Pennbrooke Fairways, Highland Lakes and Scottish Highlands are the communities this site is written for, and we prepare the architectural review paperwork when the HOA requires it. For Hawthorne, Mid Florida Lakes, Lake Griffin Harbor, Lakeside Village, Coachwood Colony, Lakes at Leesburg and Spanish Village, see the mobile home roofing page for roof-overs, metal and coatings.
It is free, and there is no catch. We inspect, photograph and give you a written summary whether or not you hire us. The business reason is simple: a homeowner who has seen the photos and heard a straight answer tends to call us when work is actually needed. We do not offer gifts, rebates or anything else for letting us on the roof, because Florida law prohibits it and because it is not how we want to earn the job.
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Start with a free Leesburg roof inspection

Photos, a written summary and a straight answer about repair or replacement. Call the number on this page or book online; the owner confirms the appointment.

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