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Anthony C. Leonard Roofing

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9.7

Overall Score

Author: Kaitlyn Short

LAST UPDATED: September 24th, 2025

Since the early 1980s, Anthony C. Leonard Roofing has built a legacy rooted in trust, craftsmanship, and Florida-wide reliability. As a family-owned contractor now operated by the Leonard family’s third generation, the company brings more than four decades of experience delivering top-tier roofing, gutter, soffit, and fascia solutions across Southwest Florida. The focus extends beyond installing roofs, providing homeowners and businesses with enduring quality backed by a Leak-Free Guarantee.

Florida’s climate brings unique challenges like intense sun, high humidity, and unpredictable hurricane conditions demand roofs built to last. Using premium materials and professional-grade techniques tailored to the Gulf Coast environment ensures every project, from tile and shingle roofing to metal, flat roofing, and roof repairs, meets high performance and aesthetic standards while standing up to the elements. Seamless gutter upgrades and comprehensive roof solutions provide reliable protection year-round.

At the heart of Anthony C. Leonard Roofing’s work are the values that have guided the company since its founding: respect, integrity, and community. Properties are treated with the utmost care, and job sites are left cleaner and stronger than before. No unnecessary services are recommended, and deposits are never required plus the quality craftsmanship and customer satisfaction speak for themselves. Choosing Anthony C. Leonard Roofing means partnering with a company dedicated to protecting what matters most to clients.

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The Good

  • Residential and Commercial Roofing
  • Roof Repairs
  • Gutter Installation and Maintenance
  • Soffit and Fascia Services
  • Leak-Free Guarantee
  • Storm Damage Assessment and Solutions

Residential and Commercial Roofing

Anthony C. Leonard Roofing provides comprehensive roofing solutions for both residential and commercial properties. This includes the installation of tile, shingle, metal, and flat roofing systems designed to withstand Florida’s unique weather challenges. Residential roofing focuses on protecting homes from sun, rain, and storms while enhancing curb appeal. Commercial roofing solutions address durability, energy efficiency, and structural safety for office buildings, retail spaces, and other commercial facilities.

The benefit of choosing professional roofing services is the peace of mind that comes from knowing the roof will perform optimally for years. Proper installation and quality materials reduce the likelihood of leaks, structural damage, and costly repairs. Prospective clients gain confidence knowing that their investment is protected, and their property maintains value over time. Additionally, expert craftsmanship ensures that the roofing system complements the building’s design, increasing both functionality and aesthetic appeal.

Roof Repairs

Roof repairs are a critical service offered to maintain the integrity of any roofing system. Whether addressing minor leaks, storm damage, or general wear and tear, timely repairs prevent small issues from escalating into expensive problems. Anthony C. Leonard Roofing’s repair services include inspection, damage assessment, and high-quality repair work tailored to the specific type of roof—whether tile, shingle, metal, or flat.

The primary benefit to clients is prevention. Early detection and repair of roofing issues protect the interior of the building from water damage, mold, and structural weakening. Professional repair services also extend the lifespan of the roof, saving money in the long term. Clients can rest assured that their property is secure, minimizing disruption to daily life or business operations. Additionally, repairs performed by experts maintain warranty coverage and uphold the overall value of the roof system.

Gutter Installation and Maintenance

Seamless gutters and downspouts are essential components of a property’s exterior, directing water away from the foundation and preventing flooding, erosion, and water damage. Anthony C. Leonard Roofing specializes in the installation, maintenance, and repair of gutter systems that protect homes and commercial buildings alike. Properly installed gutters also reduce the risk of basement leaks and preserve landscaping by controlling runoff.

For prospective clients, the benefits of professional gutter services are significant. High-quality gutters prevent costly foundation and structural issues, reduce mold and mildew growth, and protect landscaping investments. Maintenance ensures that debris, leaves, and other blockages do not compromise the system’s performance. By investing in seamless, expertly installed gutters, clients secure long-term protection for their property while avoiding the expense and hassle of frequent repairs.

Soffit and Fascia Services

Soffits and fascia boards are critical yet often overlooked components of a roofing system. Soffits provide ventilation to the attic, reducing heat buildup and preventing moisture-related problems. Fascia boards support gutters and protect roof edges from water damage and pests. Anthony C. Leonard Roofing offers installation, repair, and replacement services to ensure these elements function optimally.

The benefits of professional soffit and fascia services are multifaceted. Proper ventilation improves energy efficiency, keeping homes cooler in the Florida heat and reducing utility bills. Correctly installed fascia prevents water infiltration and structural damage, while also providing a polished, finished look to the roofline. For clients, this means a safer, more durable roofing system and an aesthetically pleasing exterior that enhances curb appeal.

Leak-Free Guarantee

Anthony C. Leonard Roofing stands behind its work with a Leak-Free Guarantee, ensuring that all roofing projects, whether installations or repairs, meet the highest standards of quality and durability. This commitment gives clients confidence that their roof will perform as expected, protecting the interior of their property from water damage and other issues.

The main benefit of the Leak-Free Guarantee is peace of mind. Clients can trust that the roofing system will remain reliable through Florida’s heavy rains, storms, and extreme weather conditions. This guarantee also reflects the company’s dedication to exceptional craftsmanship and long-term client satisfaction. Prospective clients know they are partnering with a roofing contractor that values accountability and stands by its work, reducing the risk of unexpected costs or damage in the future.

Storm Damage Assessment and Solutions

Florida’s weather can be unpredictable and intense, making storm damage assessment and repair a critical service. Anthony C. Leonard Roofing offers comprehensive evaluation and restoration services after hurricanes, heavy storms, or wind events. This includes inspecting the roof for missing shingles, structural damage, or leaks, and providing expert repairs or replacements as needed.

For clients, the benefits are immediate and long-lasting. Timely assessment and repair prevent small issues from becoming major problems, protecting the property’s structure and interior. Professional storm services also ensure compliance with insurance requirements, maximizing claims and minimizing out-of-pocket expenses. Additionally, having experts handle damage assessment and repairs reduces stress and ensures the property is restored safely, efficiently, and effectively.

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The Bad

  • Geographic Service Area
  • Material and Design Limitations
  • Weather-Dependent Work
  • Insurance and Permit Requirements

Geographic Service Area

Anthony C. Leonard Roofing serves Southwest Florida. Clients outside this area may face limited availability, longer response times, or additional travel-related costs. Prospective clients should confirm that their property falls within the company’s service range before engaging.

Material and Design Limitations

While Anthony C. Leonard Roofing offers a variety of roofing types: tile, shingle, metal, and flat roofs. Some specialized materials or architectural designs may require alternative contractors. Certain historic homes, extremely steep roofs, or unconventional designs may pose additional challenges or cost considerations.

Weather-Dependent Work

Roofing and exterior projects are inherently weather-dependent. Heavy rain, hurricanes, or other severe weather can delay timelines, even for experienced contractors. Clients should anticipate that scheduling flexibility may be required during Florida’s rainy season or hurricane-prone periods.

Insurance and Permit Requirements

Roofing work in Florida often requires permits and may involve insurance claims, especially after storm damage. While the company can assist with these processes, clients are ultimately responsible for ensuring coverage and permitting compliance. Delays in permits or claims approval can affect project timelines.

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The Bottom Line

Anthony C. Leonard Roofing combines decades of experience, expert craftsmanship, and a commitment to quality that has made it a trusted name in Southwest Florida. Every project, whether a full roof installation, repair, or gutter upgrade, is approached with precision, attention to detail, and the highest standards of professionalism. With a focus on durability, safety, and aesthetic appeal, the company ensures that each property is protected against Florida’s unique weather challenges while enhancing its overall value.

The company’s dedication to customer satisfaction is evident in its comprehensive services, from roof inspections and repairs to seamless gutter systems and storm damage restoration. With the Leak-Free Guarantee, clients gain peace of mind knowing that every job is completed to rigorous standards and backed by a promise of lasting performance. Every interaction reflects the values of integrity, respect, and community that have guided the company since its founding.

Choosing Anthony C. Leonard Roofing means partnering with a roofing contractor that prioritizes both quality and client trust. Properties are treated with care, projects are completed efficiently, and solutions are tailored to meet each client’s unique needs. For homeowners and businesses seeking a dependable, experienced, and results-driven roofing partner, Anthony C. Leonard Roofing stands out as a name synonymous with reliability, excellence, and long-term protection.

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What people are saying on Google

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Rhonda Manyak

After a three-year ordeal with our roof settlement from Hurricane Ian, Anthony C. Leonard Roofing was a breath of fresh air! From day one, they made our home a priority and exceeded every expectation. Our experience was stellar from start to finish. Tyler, our roof rep, was patient, professional, and quick to answer every question (and there were many!). Heather ensured our color and material selections were perfect, Melissa handled scheduling with speed and efficiency, and Sam oversaw the project with care and attention to detail. The communication from this team was outstanding — we were kept informed every step of the way. We had spoken to several other roofing companies before, but Leonard Roofing instantly gave us confidence. Dan, the owner, even joined our first meeting at our kitchen table — something no other company did. They came prepared with multiple roof system options, complete with clear estimates and explanations. That professionalism and transparency made our decision easy. Their construction prep was impressive — they covered and protected our landscaping, fountain, shutters, and even took the extra step to safeguard our neighbor’s property. Our biggest concern was driveway damage from heavy equipment, and Leonard Roofing immediately assured us they used construction mats rated up to 80,000 pounds. That sealed the deal — and they followed through flawlessly. Every team member was polite, considerate, and professional. Our yard was cleaned daily, and the crew’s respect for our property (and our neighbors) did not go unnoticed — no loud music, no mess, just hard work and pride in what they do. They even surprised my husband with a birthday treat during the project — such a thoughtful gesture! It’s rare to find a company that delivers both quality and genuine care, but Anthony C. Leonard Roofing does exactly that. They don’t just install roofs — they build trust.

1 week ago

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sun rize

this is one of the most professional companies that I’ve dealt with in Florida. As a commercial general contractor in Missouri for 40 years, I have dealt with hundreds of subs ……so I have seen the good and the not so good. This company is fair, professional and kept their commitments I would not hesitate in the least to use them again in the future

1 week ago

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Cindy Shipley

Anthony Leonard repaired my roof after hurricane Milton. They came on time when scheduled, and made the necessary repairs in a timely fashion. I would recommend them for your roofing needs.

1 week ago

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Christine Arch

The transition of my roof replacement went very smoothly. From Sales to Labor, I was satisfied with the 3 P's: (Price, Promptness & Professionalism) as well as Great Communication!

2 weeks ago

Star Rating

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5.0

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41 Reviews

Review Breakdown

5 grade

95%

4 grade

5%

3 grade

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2 grade

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1 grade

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Sentiment Criteria

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Quality

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Service

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Trustworthiness

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Verified Customer

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Review Source

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Stephen Carden

There was a slight miscommunication in that I had to reach out to them in order to move the contract process forward, but once that was done they scheduled quickly and did a great job. I would definitely recommend this company to others.

3 months ago

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Verified Customer

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Review Source

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Tim Fahey

Great crew and Supervisor. Just need to train the rookies better. I wouldn't hesitate hiring them for a new roof!

3 months ago