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  • Verified reviews icon1.6k+
    Verified roofing services reviews

Top-Rated Roofers in Winter Springs - Updated Nov 2026

Avatar for Castle Roofing Group, LLC
Castle Roofing Group, LLC
4.8(
39
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For Business

Serving Winter Springs, FL and surrounding areas

Approved

In business since 2020

Free estimates

Warranties offered

The goal of Castle Roofing Group LLC is to focus on providing quality, fair, and honest service to all our customers. A roof replacement is a big decision, and it should never feel confusing or rushed. Castle Roofing Group helps you understand what your roof needs, what your options are , and what the full scope looks like before work begins. \n\nThat Means: \n\n* Clear Answers\n* Evidence-Backed Findings \n* A Scope of Work You Can Understand \n* A Timeline You Can Plan Around \n* A Clean Job Site and Respectful Crews \n* Work We Stand Behind After The Last Nail is In \n\n\n

Our Projects
Our Projects
Our Projects
Our Projects
Our Projects

+6

Response time2 days
42 neighbors recently requested a quote
Recommended by85%of homeowners
Avatar for Sun State Roofing LLC
Sun State Roofing LLC
5.0(
48
)
Asphalt Shingle Roofing - RepairSealant for Roof - ApplyFlat, Foam or Single Ply Roofing - Repair+3 more

Serving Winter Springs, FL and surrounding areas

Approved

Super Service Award Winner

In business since 2023

Free estimates

Credit card accepted

"I had a great experience with Benjamin and Sun State roofing. Ben was very professional and knew exactly what my roof needed. He walked me through the entire process and was there if I had any questions. I would highly recommend Sun State Roofing to anyone who needs roofing work."
Response time5 hrs
Response rate100%
23 neighbors recently requested a quote
Avatar for Roof Squad
Roof Squad
4.8(
225
)
Asphalt Shingle Roofing - Install or ReplaceMetal Roofing - Install or ReplaceAsphalt Shingle Roofing - Repair+1 more

Serving Winter Springs, FL and surrounding areas

Approved (Corporate)

In business since 1990

Free estimates

Emergency services offered

At Roof Squad Orlando, your peace of mind is our top priority. Whether you need residential roofing services or a reliable commercial roofer, we?re here to help. Our team works diligently from the first phone call to the final inspection, ensuring every shingle is installed with precision and care. As your trusted local roofing company, we go the extra mile to deliver exceptional service, quality craftsmanship, and fair pricing?keeping your roof and your home in top shape.

Commercial Roofing
Residential Roofing
Gutter Installs
53 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for Northmen Roofing
Northmen Roofing
4.9(
50
)
Natural Slate Roofing - RepairTraditional Tile Roofing - RepairFlat, Foam or Single Ply Roofing - Repair- For Business+2 more

Serving Winter Springs, FL and surrounding areas

Approved

In business since 2020

Free estimates

Emergency services offered

""We live in Orange County, Florida. In 2016 we replaced our bungalows flat roof. In August, 2019, after a little "blow" we had a few leaking issues. We called the 2016 roof installer and was referred to a third party for repairs: Travis Raper, who is now the Principal of Northman Roofing, was the professional who was assigned the task of replacing 3 skylights because the 3 skylights that were installed were manufactured for peaked roofs. Not Florida flat roofs. ... Did you know that Florida bungalows all have flat roofs? Well, for one, it doesn't snow. Second. A peaked roofs are far more susceptible to wind and rain damage. ... Right after a little "spinner" about 6 weeks ago, I called Mr. Raper about a small leak in the kitchen. Soon thereafter he and crew called and came out to make an assessment. Turns out my kitchen leak was easily resolved, but Mr. Raper took a cursory review of the roof. None of the "boots" at initial installation had been properly installed. ... Long story short: The day before Ian struck Orlando Mr. Raper and 3 members of his Crew were on my roof securing any and all possible leak issues. ... We have zero roof damage, and zero leak issues. ... Thank you Mr. Raper and Crew.""
Northmen Roofing - Concrete Tile Repair
Northmen Roofing - Concrete Tile Roof Inspection
Northmen Roofing - Concrete Tile Repair
Northmen Roofing - Concrete Tile Repair
Northmen Roofing - Concrete Tile Repair

+66

Response time10 hrs
Response rate97%
2 neighbors recently requested a quote
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Roofing FAQs, answered by experts

Metal roofs do not inherently leak more than shingle roofs; when properly installed, they are generally less likely to leak. Asphalt shingle roofs are more susceptible to leaks due to factors like wind uplift, damage from extreme weather, moss growth, and ice dams. Over time, asphalt shingles also lose their protective grit, which reduces their waterproofing capabilities. In contrast, metal is a more resilient material that stands up better to heavy precipitation and high winds. However, metal roofs can develop leaks if they are poorly installed, have improperly sealed fasteners, or experience issues from thermal expansion. For this reason, professional installation and regular maintenance are crucial to ensure a metal roof's longevity and superior protection against leaks.

EPDM roofing is a single-ply roofing material made of rubber, and a professional will install it in a single sheet and seal the seams. Built-up roofing (BUR) consists of multiple layers made from asphalt, adhesives, and roofing felt. A professional will construct the layers of BUR on-site. EPDM is easier to repair and has better resistance to extreme temperatures, while BUR is more fire-resistant and affordable.

The short answer is, yes, cedar shakes do last longer than asphalt shingles. But the long answer is, it depends on maintenance. Asphalt shingles last about 20 years, while cedar shingles typically last about 30 years with proper maintenance. If they are very well maintained and installed in an area with a mild, drier climate, they can last up to 50 years.

Using a staple gun to hang Christmas lights on your roof or shingles is not recommended. Puncturing your roof with staples can cause damage, leading to cracks, leaks, and exposure to the elements. Staples are also less reliable than other methods like roof clips. For a safer alternative that won't damage your roof, use shingle tabs.

Due to the complexity and weight of tiles, DIY is not recommended. Professional installation ensures proper alignment and durability.

The Winter Springs, FL homeowners’ guide to roofing services

From average costs to expert advice, get all the answers you need to get your job done.