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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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Immediate service. Honest, affordable & dependable.

"Immediate service. Honest, affordable & dependable. Would recommend. They cleaned up so that you can't even tell anyone came!"

Phillip R.

They cleaned up so that you can’t even tell anyone came!

“Referred from Angie's List. Immediate service, Honest, affordable, & dependable. Would recommend. They cleaned up so that you can't even tell anyone came!”

Phillip R.

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.

They did an awesome job installing a new metal roof.

They did an awesome job installing a new metal roof. The price and workmanship are great! Thanks Paul and Carl.

Jaferleen P.

I know a number of friends he has helped as well.

John really knows his stuff about roofing and he will not tell you anything that’s not true about your roofing needs; I know a number of friends he has helped as well.

Paul N.

I’m very satisfied and would recommend them!

“I selected Montgomery Winslow Roofing after conversations with the owner, John Woolston. I’m very satisfied and would recommend them.”

Dennis F.

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.

Thank you, Montgomery Winslow Roofing!

“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 Roofing.”

Nancy B.

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.
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Servicing Fort Myers, Cape Coral, And More

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