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Roofing Company in Fort Myers, FL

Wide Selection. Detail-Obsessed Workmanship. Residential Roofing Pros.

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Residential & Commercial Roofing Services in Southwest Florida

Explore our services to find what works best for your residential or commercial roofing project.

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Residential Roof Repair in Fort Myers & Lee County
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Residential Roof Replacement for Fort Myers Homeowners
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New Construction Roofing in Southwest Florida
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Commercial Roof Repair in Fort Myers & Cape Coral
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Commercial Roof Replacement for Southwest Florida Businesses
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Commercial New Construction Roofing in Lee County

A Family-Owned Roofing Company with 75 Years
in Southwest Florida

Our Residential Roofing Systems Are Built For Long-Term Home Protection

We get it. Whether you’re a Southwest Florida homeowner or in the commercial sector, anything roofing can seem overwhelming. But at Montgomery Winslow Roofing, our professionally trained and certified team is here to guide you through the process.

From roof repairs to full roof replacements or new construction projects, we offer diverse options and customized services to meet your needs. By listening to you, we’re able to pair you with quality products that match your wants and needs and give you uncompromised, long-lasting results.

Plus, with our no-corners-cut installations and outstanding warranties, you’re guaranteed long-term roofing excellence and total peace of mind.

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Fort Myers Roofing Contractor Serving Cape Coral & Lee County

At Montgomery Winslow Roofing, the term “family-owned” is more than a buzzword. It means trust in an established company invested in your roofing success. Our company is more than just our livelihood – it’s a commitment to giving our community and neighbors the long-term roofing results they deserve.

Why Choose Us

Roof Replacement & Repair Products Built for Florida's Climate

We don’t limit ourselves to one roofing manufacturer. Instead, we offer a variety of heavy-duty products from brand names we’ve come to trust and depend on 100% of the time. With our decades-long manufacturer relationships, we can assure you get uncompromised quality and reliable warranties.

Heavy Duty Products

Integrity Above All - The New Roofing Standard

Accountability. Trustworthiness. Integrity. These are not often words associated with roofing contractors. At Montgomery Winslow Roofing, our unflinching core values help us break the mold when it comes to the roofing standard. You should expect more from your contractor…and our core values ensure we give you just that – more.

Our Core Values

What Fort Myers Homeowners Say About Montgomery Winslow

Hear From Our Happy Southwest Florida Customers

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The experience was easy!

“I would recommend this roofing company to others because I believe they are fair. The experience was easy.”

Barbara & Monti

Thank you to all the workers for a job well done!

“From the first meeting with Paul till today, when my roof is done, I have had nothing but praise for this company! The workers were exceptionally meticulous and truly took extra care not to leave anything behind, from tear-off to shingles. I'm so happy my son suggested I call Paul...

Connie P.

The 10 year warranty makes us feel a lot better too.

This company rates a 5 star plus rating. Everything was completed as promised and then some. They installed a beautiful new cement flat tile roof for us and John, Dane, Melissa, and Pat were wonderful to work with from start to finish. They were very helpful in selecting the style...

George H.

Thank you to all the workers for a job well done!

From the first meeting with Paul till today when my roof is done I have had nothing but praise for this company! The workers were exceptionally meticulous and truly took extra care to not leave anything behind from tear off to shingles. I'm so happy my son suggested I call...

Connie P.

Everyone was pleasant, knowledgeable and experienced;

I thought Montgomery Winslow Roofing was the most qualified of the three estimates I received. Everyone was pleasant, knowledgeable and experienced; they did more than they said.

Ray A.

I like everything about the experience!

“I would recommend this roofing company to others because I believe they are the best & I like everything about the experience.”

Carole L.

Honest, good value for their quality work. Excellent job.

Good attention to details and prompt answers to my questions. Honest, good value for their quality work. Excellent job.

Sanford M.

Good job. Also personnel explained what they had done.

Family customer since 1950's. Ernest workers who know their trade. Good job. Also personnel explained what they had done.

Philippe C.

My experience with this company was excellent.

My experience with this company was excellent. John and his crew are experienced roofers, professional and personable. Melissa is the "go to girl" in the office who keeps things running smoothly. Thank you Montgomery Winslow.

Nancy B.
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