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★★★★★ 5.0 (352) 272-8854

Roofing in Leesburg, Florida.

We're the Leesburg roofing contractor handling everything from Plantation re-roofs to commercial flat roofs along the US-27 corridor. Licensed Florida roofer (FL #CCC1335465) based in Eustis, 18 minutes away - estimates within 48 hours, written quotes in plain English, and a 5-year workmanship warranty.

FL License
#CCC1335465

- Free · no obligation

Request your quote.

★★★★★5-Star Google Reviews(352) 272-8854
7+
Years Local
Serving Lake County
500+
Roofs Completed
Across Lake County
5.0
Google Rating
5-Star Reviews
18 minutes
Response Time
From Eustis HQ
- Leesburg Local Knowledge

Roofing in Leesburg, done right.

Pro Specialty Services serves Leesburg homeowners with expert roofing. We're just 10 miles (18 minutes drive) from our Eustis headquarters - Leesburg is squarely in our core service area, which means faster response and real accountability on every project.

Leesburg stands as Lake County's largest city with approximately 27,000 residents, earning its nickname as the "Lakefront City" thanks to its prime location between two of Central Florida's most significant bodies of water - Lake Harris to the south and Lake Griffin to the north. This dynamic community blends historic character with modern growth across a diverse landscape of neighborhoods and commercial centers. The crown jewel of Leesburg's parks system is Venetian Gardens, a stunning 25-acre waterfront park on the shores of Lake Harris featuring manicured gardens, scenic boardwalks, a fishing pier, and boat ramps that make it a premier recreation destination in Lake County. Downtown Leesburg has undergone a vibrant revitalization with restored historic buildings housing local restaurants, craft breweries, boutique shops, and community event spaces along Main Street. The city's commercial corridor along US-27 serves as a major retail and business hub for the entire region, with major shopping centers, medical facilities, and professional offices. Leesburg hosts Florida's largest motorcycle event - Leesburg Bikefest - drawing over 250,000 visitors annually, plus popular seasonal events like the Leesburg Art Festival and the downtown Mardi Gras celebration. Established neighborhoods like Royal Highlands (a 55+ active adult community), Plantation at Leesburg, and the Silver Lake Estates area offer mature landscaping and established community amenities, while newer developments continue to expand the city's footprint. The Leesburg area also includes surrounding communities like Haines Creek, Lisbon, and Okahumpka that share the same roofing challenges and service needs.

Leesburg's unique position between Lake Harris and Lake Griffin creates a dual-lake microclimate that presents significant roofing challenges. Properties along both waterfronts experience elevated humidity from two directions, accelerating shingle deterioration, promoting algae and moss growth, and increasing the risk of moisture intrusion through aging underlayment. Waterfront homes in Silver Lake Estates and along the Lake Harris shoreline face stronger wind exposure during storms, with open water fetch allowing wind gusts to build momentum before hitting rooflines. The city's diverse housing stock spans over six decades - from 1960s ranch homes in the historic district with original roof structures and potentially asbestos-containing materials, to 1980s-90s construction in Royal Highlands and Plantation with aging 3-tab shingles, to newer subdivisions with builder-grade roofing that may underperform during severe weather. Leesburg's growing commercial sector along US-27 includes flat-roof retail buildings, medical offices, and warehouse facilities that require specialized commercial roofing expertise including TPO membranes, modified bitumen systems, and standing seam metal roofing. The area's summer storm patterns are particularly intense, with Lake Harris and Lake Griffin creating a thermal corridor that amplifies afternoon thunderstorm activity - bringing heavy rain, damaging hail, and high winds that cause more roofing damage per capita than many surrounding Lake County communities. Metal roofing has become increasingly popular among Leesburg homeowners seeking long-term durability, with standing seam and stone-coated steel options offering superior wind resistance rated for 140+ mph, energy efficiency through reflective coatings, and lifespans of 40-70 years that outperform traditional shingles by decades.

We know the Lake County permit office, we know which HOAs require architectural shingles over 3-tab, and we know which Leesburg neighborhoods insurance adjusters inspect hardest. That's the advantage of hiring local.

- Systems We Install & Repair

Roofing Services in Leesburg

Illustration of a residential roof replacement of the kind Pro Specialty Services performs for Leesburg homeowners
Illustration of a residential roof replacement of the kind Pro Specialty Services performs for Leesburg homeowners
Illustration of residential roofing work of the kind Pro Specialty Services performs in Leesburg, Florida
Illustration of residential roofing work of the kind Pro Specialty Services performs in Leesburg, Florida
Illustration of a flat roof roof system installed by licensed Florida roofing contractors
Illustration of a flat roof roof system installed by licensed Florida roofing contractors
Illustration of a metal roof system installed by licensed Florida roofing contractors
Illustration of a metal roof system installed by licensed Florida roofing contractors
- Reviews from Leesburg

All five-star reviews.
Real work. Real neighbors.

5.0
Google verified · 5-Star Rating
Read all on Google →
Google review · Verified
Caleb of Pro Specialty Services put a new roof on our house. The job was superb and done without delay. We were kept informed and knew when every step was going to happen, with no surprises. I would highly recommend Pro Specialty Services to my family and friends. It's a case of professional people doing a pro job and they made sure that we, as the customer were satisfied and I felt that the pricing was very competitive.
James Ross
Google review
Google review · Verified
Caleb was great to work with. He showed me options and didn’t try to push me into the most expensive. He’s honest and hard working
Pat Darrow
Google review
Google review · Verified
Caleb and his crew went above and beyond. Their service is meticulous. We were quoted one price and they stuck to it. There was a lot of wood damage on our shed and they repaired/replaced the wood and painted it. It doesn't even look like it was repaired. It looks new and fresh. Years ago we had a panel roof installed and Caleb said it was done incorrectly. They repaired flashing along the panel roof, removed vinyl siding, installed flashing correctly and sealed the roof. Great job!! A new door was installed in the garage, painted the porch banister and many more things. The list can go on and on. Everything was done to our satisfaction. Everyone on the team was friendly and co-operative. We highly recommend their services.
Janis Herpst Black
Google review
- Book it

Book a visit in Leesburg.

Tell us what you need, pick a day and a time window, and we’ll confirm the exact time. Your slot is held before we ask for a phone number.

Rather call? (352) 272-8854

Step 1 of 3

What do you need?

- Quick quote

Get a fixed price,
in writing.

Tell us about your Leesburg roof. We'll follow up within 48 hours with a free, no-pressure estimate. We actually go up on the roof to quote it.

- Free · no obligation

Request your quote.

★★★★★5-Star Google Reviews(352) 272-8854
- FAQ

Leesburg homeowners
keep asking these.

If your question isn't here, call us or drop it in the form. We'll answer honestly - even if the answer is "you don't need a new roof yet."

Do you serve all of Leesburg?
Yes, we serve all Leesburg neighborhoods from downtown to the newer developments near US-27. At just 10 miles from our Eustis office, Leesburg is well within our core service area. We can typically schedule inspections within 24-48 hours.
How much does roof replacement cost in Leesburg?
Roof replacement costs in Leesburg typically range from $8,500 to $28,000 depending on roof size, pitch, materials, and complexity. The average Leesburg home (around 1,800 sq ft) costs $12,000-$18,000 for quality architectural shingles. We provide detailed, itemized estimates at no charge.
Do you work on commercial buildings in Leesburg?
Yes, we handle commercial roofing projects in Leesburg including flat roofs (TPO, modified bitumen), metal roofing, and more. Our commercial experience includes retail buildings, offices, and warehouses throughout Lake County.
What's the best roofing for new Leesburg developments?
Many new Leesburg homes come with basic 3-tab shingles that may not hold up well long-term. We recommend upgrading to architectural shingles or metal roofing for better durability, wind resistance, and curb appeal. These upgrades typically add significant value to your home.
How much does metal roofing cost in Leesburg?
Metal roofing in Leesburg typically costs $15,000-$30,000 depending on roof size, metal type, and complexity. Standing seam metal roofing is the premium option at $18,000-$30,000, while stone-coated steel offers a more affordable metal option at $15,000-$22,000. Metal roofs last 40-70 years and can significantly reduce cooling costs - a smart investment for Leesburg's dual-lake humidity. We provide free metal roofing estimates with material samples.
Who is the best roof repair company in Leesburg?
Pro Specialty Services is the top-rated roofing contractor serving Leesburg with consistent 5-star Google reviews. At just 18 minutes from our Eustis office, we offer faster response times than Orlando-based contractors. We install GAF, Owens Corning, and CertainTeed shingles to manufacturer spec, are fully licensed (CCC1335465), and provide free inspections. Our owner, Caleb, personally oversees every Leesburg project for quality assurance.
Do you handle commercial flat roofs in Leesburg?
Yes, we specialize in commercial flat roofing throughout Leesburg's US-27 business corridor and downtown area. We install and repair TPO, modified bitumen, and EPDM flat roof systems for retail buildings, offices, warehouses, and multi-tenant properties. We also offer commercial roof maintenance programs to extend your roof's lifespan and prevent costly emergency repairs.
Can you help with roof insurance claims in Leesburg?
Absolutely. Leesburg's position between Lake Harris and Lake Griffin means more storm exposure and more insurance claims. We have extensive experience documenting storm damage, meeting with insurance adjusters, and ensuring homeowners receive fair claim settlements. We provide detailed photo documentation, damage reports, and can supplement underpaid claims.
- Your Local Roofer

Your Local Leesburg Roofer

Finding a reliable roofing contractor in Leesburg shouldn't be a gamble. Pro Specialty Services is fully licensed (CCC1335465, CGC1538852) and insured, serving Lake County since 2019.

Owner Caleb Hutchinson personally oversees every project - you'll never be handed off to a salesperson or subcontractor. We've built our reputation one Leesburg roof at a time.

Meet Caleb & the team →
- Insured
Fully Insured
Your home protected
- Materials
Premium Brands
GAF · OC · CertainTeed
- Local
18 minutes away
From Leesburg
- Family
Family Owned
Since 2019

- Manufacturer Partners

GAF shingles installed by PSSCertainTeed shingles installed by PSSABC Supply Partner - premium roofing materials supplierROMAC supplier partnerTri-County supplier partner
- Storm Response

24/7 Emergency Roof Repair

When storm damage strikes your Leesburg home, you need a roofing contractor who responds fast. Pro Specialty Services offers 24/7 emergency roof repair across Lake County. Located just 18 minutes away, we reach Leesburg quickly when you need us.

From emergency tarping that prevents further water damage to permanent repairs and full insurance claim handling, we manage every step of your Leesburg roof emergency.

- 01
24/7 Storm Response
Day or night for Leesburg homeowners
- 02
Emergency Tarping
Immediate protection from water intrusion
- 03
Insurance Claims
We handle paperwork and meet adjusters
- 04
Permanent Repairs
Quality fixes that restore protection
Available 24/7

Roof emergency in Leesburg?

Don't wait. Call now for immediate emergency service.

(352) 272-8854
- Peace of Mind

Financing & warranty protection.

- Flexible Financing

Make your roof affordable.

Get the roof you need with monthly payments that fit your budget.

  • 0% interest options available
  • Low monthly payments
  • Quick approval process
  • No prepayment penalties
Ask about financing
- Warranty Protection

Your investment, protected.

Industry-leading warranties for lasting peace of mind.

  • Manufacturer warranties up to 50 years
  • Workmanship guarantee included
  • Transferable to new owners
  • No-hassle claim process
Learn about warranties
- Neighborhoods

Leesburg areas we serve.

Roofing services throughout Leesburg and surrounding neighborhoods.

Downtown Leesburg
Royal Highlands
Plantation at Leesburg
Silver Lake Estates
Venetian GardensLearn more →
Lake Harris Shores
Haines Creek
North Lake Business District
US-27 Corridor

Don't see your neighborhood? Contact us to confirm

- Service Area

Serving Leesburg & Lake County.

- Our Office

Eustis, FL headquarters

3105 Kurt St, Eustis, FL 32726

- Leesburg Coverage

Leesburg, FL

10 miles from office · 18 minutes drive

- Nearby · Lake County

One crew, the whole county.

Same pricing, same warranty, same phone number whether you're in Leesburg or a neighboring town.

From office
10 miles
Drive time
18 minutes
Response
< 24 hr

Ready for your free roof estimate in Leesburg?

On-site inspection, photos of every problem area, and a written quote within 48 hours. No pitch, no pressure.

- Ready when you are

Roof trouble in
Leesburg?

Free, no-pressure estimate. We actually go up on the roof to quote it. Fixed price in writing, valid 60 days. Most estimates scheduled within 48 hours.

- Prefer to talk?
(352) 272-8854
Mon-Sat · 7am-7pm
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