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- Roof repair · Leesburg, FL

Roof repair in Leesburg that holds

Leaks, wind-lifted shingles, split pipe boots, failed flashing, rotted fascia and storm patches on roofs from Scottish Highlands to Royal Highlands. Free inspection first, written price second, 2-year workmanship warranty on every repair.

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Roof repair in Leesburg is mostly a question of age and water. More than half of the city's homes were built before 1990, the median build year is 1985, and the big 55+ communities along US 27 South went up between 1987 and 2008. Those roofs are now at the point where a boot splits, a flashing lets go or a wind gust lifts a dozen shingles, and the homeowner has to decide between a repair and a replacement without a lot of good information.

Pro Specialty Services is a Florida-certified roofing contractor (CCC1335465) based in Eustis, about 25 minutes from Leesburg. We treat repair as the first option, and we are comfortable saying "that is a repair" when it is one. Our free inspection produces photos and a written summary; our repair contract spells out the scope and carries a 2-year workmanship warranty on the repaired area, backed by our Leak-Free Promise.

This page covers the repairs we do most in Leesburg, what each one involves, how the Florida 25% rule shapes the repair-versus-replace decision, and what to expect from the day we show up.

The roof repairs we do most in Leesburg

Nearly every Leesburg repair call falls into one of these categories. Each has a right way and several wrong ways to fix it.

Leaks

A ceiling stain is a symptom; the entry point is usually uphill and often a few feet sideways. We trace it from the attic and the roof surface before pulling anything apart. The roof leak repair page goes deep on where Leesburg roofs leak by age.

Missing, lifted or creased shingles

Wind gets under a tab whose sealant strip has let go, folds it back, and either tears it off or leaves a crease that will fail next time. We replace the damaged courses, hand-seal the courses above and below, and check the rest of the slope for broken seals. On 3-tab roofs from the 1980s and early 1990s, matching color is approximate at best; we tell you that up front.

Flashing

Step flashing at sidewalls, apron flashing at headwalls, counterflashing at chimneys, kickout flashing where a roof edge meets a wall. On older homes in Palmora Park, Silver Lake and the ranch streets north of downtown, the original galvanized metal has often been caulked over repeatedly. We replace the metal rather than add another bead.

Pipe boots and vents

Neoprene boots from the 1999 to 2006 Royal Highlands and Legacy construction wave are at the end of their life. The fix is a new boot or a lead or metal-collar boot that outlasts the shingles, plus resealed goose-necks, off-ridge vents and turbine bases.

Soffit, fascia and drip edge

Overflowing gutters and missing drip edge rot fascia boards first, then the soffit, then the rafter tails. We replace the wood, add drip edge where it was never installed, and re-hang the gutter.

Storm patches and emergency tarping

After a wind event we secure the opening the same visit when it is safe to work, document the damage, and write the permanent repair scope. The storm damage page covers tarping, photos and insurance paperwork.

What a Leesburg roof repair visit looks like

You call or book online; we confirm a window, typically within 48 hours on weekdays. Active leaks go to the front of the schedule.

  1. Inspection. We walk the roof when the pitch and surface allow it, photograph the suspect area and every other penetration, valley and flashing, then check the attic side for staining, daylight and wet insulation.
  2. Written summary. You get the photos and a plain-language note: what is wrong, what caused it, what else is close to failing, and whether a repair is sensible.
  3. Written price. A repair contract with the scope, materials and price. The number on the contract is the number you pay; if we open the roof and find something we could not see, we stop and get your written approval before doing anything extra.
  4. The repair. Most single-area repairs take a few hours to a day. We bring the matching shingle, flashing stock, boots, sealant, underlayment and decking so a hidden surprise does not mean a second trip.
  5. Photos and warranty. You get after photos and a written 2-year workmanship warranty on the repaired area. If it ever leaks because of our work, we are on site within 48 hours at no cost.

If a permit is required for the scope (decking replacement, or a repair large enough to count against the 25% rule), we pull it from the City of Leesburg Building Division at 501 W Meadow St, (352) 728-9700, for addresses inside the city, or from the Lake County Office of Building Services in Tavares, (352) 343-9653, for unincorporated addresses, which includes most of 34788 and Haines Creek.

Repair or replace: the Florida 25% rule explained

Florida's existing-building code sets a bright line that every Leesburg homeowner with an older roof should know. Under the Florida Building Code, Existing Building, section 706.1.1, if more than 25% of a roof section is repaired, replaced or recovered within a 12-month period, the whole section has to be brought up to current code, which in practice means a full replacement.

There is one important exception, written into Florida Statute 553.844(5) in 2022: the rule does not force a replacement if the existing roof was built or replaced to the 2007 Florida Building Code or later. The 2007 code took effect on March 1, 2009. So:

  • A roof installed on or after March 1, 2009 can have more than 25% of a section repaired without triggering a full replacement.
  • A roof older than that, which describes most of Scottish Highlands, Pennbrooke Fairways, Highland Lakes, Plantation, Royal Highlands and the original Legacy streets, is limited to 25% of a section in any 12 months before the code requires replacement of that section.

"Section" matters. A hip roof on a Royal Highlands villa has four or more sections; a gable ranch off CR 44 has two. Storm damage confined to the back slope can often be repaired even on an older roof, because 25% of one slope is a lot of shingles. Damage scattered across every slope usually cannot.

We measure, photograph and put the math in the written summary so you can see which side of the line you are on, and so the inspector sees it too. Guessing wrong in either direction costs money: a repair the code will not allow has to be torn out, and a replacement that was never required is the most expensive repair there is.

Repair versus replacement: the decision table

Beyond the code, here is how we weigh the call on a Leesburg roof. None of these rows is a rule by itself; two or three together usually settle it.

What we findUsually a repairUsually a replacement
Roof age (architectural shingle)Under about 18 years, one failed componentPast 22 to 25 years with widespread wear, or any age where every repair breaks the shingles around it
Roof age (3-tab shingle)Under about 12 yearsPast 15 to 18 years; most remaining 3-tab in Leesburg dates to the 1980s and early 1990s
Damage areaOne slope, under 25% of that section (or any size on a post-March-2009 roof)Over 25% of a section on a pre-2009 roof in a 12-month period
DeckingSolid; one or two soft spots at a known leakSoft or delaminated across multiple areas, or plank decking with gaps on a 1950s to 1960s home
Granule lossLocal, around a leak or a ventGranules filling gutters, fiberglass mat showing through on sun-facing slopes
Leak historyFirst leak, clear causeThird or fourth leak in different places; patches on top of patches
Insurance positionRoof under 15 years, or a 15+ roof that will pass a 5-years-remaining inspection after the repairCarrier has already asked for roof replacement at renewal and the inspection cannot honestly show five years of life
LayersSingle layerSecond layer of shingles over the first (common on older ranches); repairs never seal well through two layers

If the table points to replacement, the roof replacement page explains the process, the Lake County re-nail requirement for pre-2002 homes, decking terms and the 10-year workmanship warranty. Financing is available on replacements; see the financing page.

Roof repair for Leesburg's 55+ communities

Royal Highlands, Plantation at Leesburg, Legacy of Leesburg, Arlington Ridge, Pennbrooke Fairways, Highland Lakes and Scottish Highlands are the communities this page is written for, and they have a few things in common.

  • Same builder, same roof, same year. When one boot fails on a street of 2003 villas, the rest of the street is next. We will tell you if the repair you called about is a symptom of a roof-wide pattern, and we will tell you if it is not.
  • Architectural review. Most of these HOAs require ARC approval for visible changes. A like-for-like repair rarely needs it; a color change, a switch to metal, or a replacement usually does. We prepare the submission when it is required.
  • Attached and zero-lot-line homes. Villas and duplexes in Highland Lakes, Scottish Highlands and parts of Plantation share roofs or sit a few feet apart. We coordinate with the neighbor when a repair crosses the party line and keep ladders and debris off their side.
  • Insurance timing. A roof installed in 2004 passed the 15-year mark in 2019. Under Florida Statute 627.7011(5) a carrier may ask for an inspection showing at least five years of useful life. A clean repair followed by that inspection is often the difference between renewing and shopping for coverage. We are licensed roofing contractors, which the statute names as authorized inspectors.

Manufactured homes in Hawthorne, Mid Florida Lakes, Lake Griffin Harbor, Lakeside Village, Coachwood Colony and Spanish Village are a different animal: seams, fasteners, coatings and roof-overs rather than shingles. They have their own page at mobile home roofing.

Repairs on older downtown and CR 44 ranches

The 1950s to 1970s homes in Palmora Park, Silver Lake and the grid north and west of downtown are the other half of the Leesburg housing picture, and they fail differently. The roofs are lower-pitched, the decking is often tongue-and-groove plank or thin early plywood, and there has usually been at least one re-roof, sometimes over the original layer.

What we watch for on these houses:

  • Two layers. A second layer of shingles over the first was legal for decades. Repairs through two layers rarely seal, nails do not reach solid wood, and the weight adds up. We will show you the edge where the layers are visible.
  • Plank gaps and rot at the eaves. Decades of overflowing gutters rot the first foot of decking. A repair here includes new sheathing and drip edge, not just shingles.
  • Chimney and wall flashing on additions. Many of these homes have a Florida room or carport addition tied into the main roof with a shallow pitch and a caulked seam. That seam is the leak.
  • Valleys. Closed-cut shingle valleys on low pitches hold water. We often convert to an open metal valley during a repair.

Landlords: we send the written summary and photos to you, schedule around the tenant, and invoice the entity on the deed. If the house is in unincorporated Lake County, re-roof permits are auto-issued online, which keeps a turnover window short.

Storm damage repair and the weather Leesburg roofs face

Leesburg sits in Lake County's 130-140 mph design-wind band, outside the high-velocity hurricane zone and outside the wind-borne debris region. That is good news for the code requirements you face, but the weather still arrives. Hurricane Milton on October 9 and 10, 2024 brought a 72-knot gust (about 83 mph) and 8.89 inches of rain to Leesburg per the National Hurricane Center, with 285 Lake County structures affected and 18,972 Leesburg Electric customers in the dark. Irma in 2017 gusted to 69 mph here with more than 8 inches of rain; Ian in 2022 gusted to 56 mph.

The smaller events do more cumulative damage. NOAA logged 50-knot-plus wind at Leesburg on March 30, 2021, April 25, 2023 and May 18, 2024, and inch-diameter hail at Okahumpka in 2021. Over seven decades Lake County has averaged nearly a tornado and three severe-wind reports a year, with hail peaking in May and wind in June. Normal rainfall is 43.78 inches, nearly 7 of them in June alone.

After any of these, a storm repair means: secure the opening, photograph everything, write a scope, fix it right. If you decide to file a claim, we meet the adjuster on the roof with the same photos. We are roofing contractors, not public adjusters; we do not file or negotiate claims, and the carrier decides the outcome. The main site's Leesburg storm damage guide walks through the first 48 hours after a storm step by step.

Before we arrive: what to do about an active leak

If water is coming in right now, a few minutes of effort limits the damage and makes the repair cheaper.

  1. Catch the water. Bucket or trash can under the drip, towels around it, a tarp or shower curtain over furniture, rugs and electronics.
  2. Relieve a bulging ceiling. A sagging drywall bubble is holding gallons. Poke a small hole at the lowest point with a screwdriver and let it drain into the bucket; it prevents a collapse that brings the whole panel down.
  3. Kill power to the room if water is near a light fixture, ceiling fan or outlet. Breaker first, then look.
  4. Photograph everything with a timestamp: the stain, the drip, the yard debris, any shingles on the lawn. Keep the broken pieces.
  5. Stay off the roof. Wet shingles, metal and tile are slick, and the soft spot you are walking toward is the one that gives way. Ladders in a Florida thunderstorm are a bad idea for anyone.
  6. Call the number at the top of this page. Tell us the ZIP, the roof type, roughly how old it is and where the water is appearing. That lets us load the truck with the right boot, flashing stock, underlayment and decking before we leave Eustis.

We stock the common Leesburg repair materials on the truck: architectural and 3-tab shingles in the standard Florida colors, galvanized and aluminum flashing, lead and metal-collar pipe boots, synthetic underlayment, peel-and-stick membrane, ridge cap, drip edge, fascia board, half-inch and five-eighths plywood, and roofing-grade polyurethane sealant for the places sealant actually belongs. Specialty items (a discontinued shingle profile, a specific metal panel color, a skylight curb) are ordered after the inspection and installed on a second scheduled visit.

Why repairs fail, and how ours are built not to

Most of the "repairs" we are called to redo failed for one of five reasons. Avoiding them is not complicated; it is just slower.

  • Caulk instead of metal. Sealant is a gasket, not a flashing. It lasts a season or two in Florida sun. We replace flashing with new metal, lapped and fastened the way the shingle manufacturer and the code specify.
  • Face-nailed shingles. Nails through the exposed face of a shingle are a future leak. Replacement courses are nailed under the course above and hand-sealed.
  • Wrong boot for the pipe. A boot that is a size off, or a cheap neoprene one on a sun-facing slope, cracks in a few years. We size it and use a collar that will outlast the roof.
  • Not fixing the cause. A rotted fascia board with no drip edge will rot again. A valley that holds water will leak again. The repair has to remove the reason, not just the evidence.
  • No attic check. Wet insulation and stained decking tell you where water has really been going. Skipping the attic is how a "repaired" leak shows up two rooms over.

Every repair we do carries a 2-year workmanship warranty on the repaired area and the Leak-Free Promise: if our work leaks, we are on site within 48 hours and fix it at no cost, no claim forms, no trip charge. Manufacturer warranties on the materials are separate. Read how people describe the experience on the reviews page, and more about us on the about page.

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Free roof repair estimate in Leesburg.

- 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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It depends on what failed, how high and steep the roof is, whether decking is involved and whether a permit is required, so we do not quote from the phone. The free inspection produces a written price with the scope spelled out, and that number is the number you pay unless we find a hidden condition and you approve the extra work in writing first. Most single-area repairs are a fraction of a replacement, which is exactly why we recommend them when they will hold.
Often, yes. The Florida 25% rule applies per roof section, so damage confined to one slope is frequently under the limit even on a pre-2009 roof. We measure the damaged area against the section, photograph it, and put the calculation in your written summary. If the damage crosses 25% of a section on a roof built before March 1, 2009, the code requires replacing that section, and we will say so rather than do a repair that fails inspection.
Small like-for-like repairs generally do not, but decking replacement and larger repair areas do, and the City of Leesburg and Lake County each handle their own addresses. Inside the city limits the permit comes from the Building Division at 501 W Meadow St, (352) 728-9700; in unincorporated Lake County, including most of 34788, it comes from Building Services in Tavares, (352) 343-9653. We tell you whether your scope needs one and we pull it in our name.
A written 2-year workmanship warranty on the repaired area, plus our Leak-Free Promise: if our work leaks in that time, we are on site within 48 hours and fix it at no cost to you, with no claim forms or trip charge. It covers leaks caused by our installation, not new storm damage, other contractors' work or changes you make afterward. Manufacturer warranties on shingles, boots and flashing products are separate.
On architectural shingles from the last 15 to 20 years, usually close enough that nobody notices from the street, especially after a few months of weathering. On 3-tab roofs from the 1980s and early 1990s, exact colors are often discontinued and the old shingles have faded, so the patch will be visible up close. We show you the closest match before we order it and tell you honestly how it will look.
Yes. A like-for-like repair rarely needs architectural review, but anything visible from the street that changes color or material, and every full replacement, usually does. We prepare the submission with the product data and color sample the ARC asks for. Tell us the community when you book and we will tell you whether your repair is likely to need it.
Free estimates are typically scheduled within 48 hours on weekdays, and active leaks go ahead of routine inspections. For storm emergencies call the number at the top of this page any time; when it is safe to be on the roof we secure the opening first and write the permanent scope afterward. Our office is in Eustis, about 25 minutes away, so travel is never the delay.
Your carrier decides that, and we cannot promise an outcome. What we provide is an honest inspection, photographs and a written scope that describes what is actually on the roof, and we will meet the adjuster on site if you choose to file. We are roofing contractors, not public adjusters, so we do not file or negotiate claims, and we never offer anything in exchange for an inspection or a claim.
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Free inspection with photos and a written summary. If it is a repair, you get a written price and a 2-year workmanship warranty; if it is not, we tell you that too.

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