Loading
home-banner

Roofing Company in Fort Myers, FL

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

Free Roof Cost Estimator

Get Your Free Quote

This field is for validation purposes and should be left unchanged.
First Name(Required)

By submitting this form, you agree to receive automated texts or calls from Montgomery Winslow Roofing. Msg & data rates may apply. Reply STOP to cancel. You also agree to the Terms of Service and Privacy Policy. Consent is not a condition of purchase.

Residential & Commercial Roofing Services in Southwest Florida

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

residential roof repair roofing southwest florida

Residential Roof Repair in Fort Myers & Lee County
residential roof replacement roofing southwest florida

Residential Roof Replacement for Fort Myers Homeowners
residential new construction roofing southwest florida

New Construction Roofing in Southwest Florida
commercial roof repair roofing southwest florida

Commercial Roof Repair in Fort Myers & Cape Coral
commercial roof replacement roofing southwest florida

Commercial Roof Replacement for Southwest Florida Businesses
commercial new construction roofing southwest florida

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.

home intro
home id

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

home reviews

Finally fixed eight years of problems that many roofing companies could not fix!

“Montgomery Winslow Roofing was the only company that finally fixed eight years of problems that many roofing companies could not fix. I only wish I had known them first!”

Phyllis R.

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.

Thanks so much for your help with our insurance!

Thanks so much for your help with our insurance company requests. We will keep your name and number for any roofing needs we have in the future.

Christopher T.

The owner checked all the progress!

“Very professional. Good reputation and award on Angie's List. The owner checked all the progress... They were very honest.”

Harold E.

I would recommend them to anyone!

“The price quoted and the job done were the best re-roof job I have ever done (out of nine). They did what they promised and did the job in three days from start to finish. I would recommend them to anyone.”

Friedhelm S.

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.

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.

Excellent job!

“Thank you for an excellent job and for a joyful company operation.”

Jim H.

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.
Our Blog

Latest Residential Roofing News For Southwest Florida Homeowners

Our Southwest Florida Roofing Service Areas

Servicing Fort Myers, Cape Coral, And More

Our Service Areas