MW

Montgomery Winslow Roofing

North Fort Myers
Licensed & insured DBPR verified
Residential roof replacementResidential roof repairResidential new construction roofingCommercial roof replacement+2 more
4.317 Google reviews
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About

Montgomery Winslow Roofing is a Southwest Florida roofing institution with roots dating to 1949, when Haywood and Katie Montgomery founded the original Montgomery Roofing. The Woolston family purchased the business in 1990, with F. John Woolston leading operations today. Based in North Fort Myers, Lee County, the company serves residential and commercial clients across Lee, Charlotte, and Collier counties, covering communities from Fort Myers and Cape Coral to Naples, Bonita Springs, and Port Charlotte. Montgomery Winslow holds a GAF Certified Commercial Contractor credential and is certified by Polyglass U.S.A., in addition to its Florida Certified Roofing Contractor license (CCC057707). The company is a founding member and two-time past president of the Southwest Florida Roofing Contractors Association and an FRSA member, reflecting its deep community and industry standing built over more than 75 years.

Highlights

Founded in 1949, over 75 years of Southwest Florida roofing history
GAF Certified Commercial Contractor and Polyglass certified
Founding member and two-time past president of SWFRCA
Residential and commercial roofing across Lee, Charlotte, and Collier counties
Family-owned and operated since 1990 under the Woolston family

Services

Residential roof replacement
Residential roof repair
Residential new construction roofing
Commercial roof replacement
Commercial roof repair
Commercial new construction roofing

License verification

License checked against the Florida Department of Business & Professional Regulation (DBPR). Confirm current status before signing any contract.

CompanyMontgomery Winslow Roofing
License typeCCC, Certified Roofing Contractor
License no.CCC057707
Status Active & current
License boardFL DBPR
RegionNorth Fort Myers
DBPR verified Licensed in FL

Confirm this license yourself at myfloridalicense.com.

Certifications

Florida Certified Roofing Contractor CCC057707Listed credential
GAF Certified Commercial ContractorListed credential
Polyglass U.S.A. Certified ContractorListed credential
FRSA MemberListed credential
Southwest Florida Roofing Contractors Association Founding MemberListed credential

Google reviews

4.3
Rated by 17 verified Google reviewers Verified by Google
Debbie Killijgsworth· 7 months ago

They are a great company to work with. Not only they did a great job on my new roof but they were very caring and went out of their way to help with any questions or needs I had. I would highly recommend them.

George Hagen· 7 years ago

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 and color of tile that went perfectly with the exterior of our home. The workmanship was impeccable and the work was completed in a very timely manner. There were no hidden fees or surprises and best of all they were in the lower tier of bids from the numerous ones we received before selecting this company. We wanted a perfect job and we got it! I would highly recommend this company based on the great work they did for us. And, in addition, the 10 year warranty makes us feel a lot better too. Job well done! Dr. George Hagen

Connie Peska· 8 years ago

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 Paul as I had made up my mind to go with another company. His suggestion turned out wonderfully. Thank you to all the workers for a job well done!

Nancy Bastin· 8 years ago

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.

George P.· 7 years ago

TERRIBLE customer service from a so called roofing company. They will string you along forever. Estimate for a total re-roof received mid-Oct '17. Each month after, they indicated "we have other jobs scheduled before you...but don't worry, you're on our list". 9 months later, Montgomery Winslow still could not provide a start date. This is one of those FL companies you'll want to stay away from...

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Verification badges

Earned from Montgomery Winslow Roofing's verified Florida license, live Google rating, and standing in North Fort Myers. Every badge links back to this profile so anyone can confirm it, and it updates automatically if the underlying status changes.

Verified on Roofing Companies Florida — Montgomery Winslow Roofing Established on Roofing Companies Florida — Montgomery Winslow Roofing

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Frequently asked

What is Montgomery Winslow Roofing's Florida contractor license number?
Montgomery Winslow Roofing holds Florida Certified Roofing Contractor license CCC057707, which is active and expires August 31, 2026.
How long has Montgomery Winslow Roofing been in business?
Montgomery Winslow Roofing traces its origins to 1949, giving it over 75 years of history in the region.
Where is Montgomery Winslow Roofing located?
The company is based at 11300 Deal Road, North Fort Myers, FL 33917, in Lee County.
What areas does Montgomery Winslow Roofing serve?
Montgomery Winslow Roofing serves Lee, Charlotte, and Collier counties, including Fort Myers, North Fort Myers, Cape Coral, Bonita Springs, Estero, Naples, Port Charlotte, and La Belle.
What certifications does Montgomery Winslow Roofing hold?
The company is a GAF Certified Commercial Contractor and a Polyglass U.S.A. certified contractor. It holds Florida Certified Roofing Contractor license CCC057707 and is a member of the FRSA and a founding member of the Southwest Florida Roofing Contractors Association.
Does Montgomery Winslow Roofing handle both residential and commercial roofing?
Yes. Montgomery Winslow Roofing performs residential and commercial roof replacement, repair, and new construction projects throughout Southwest Florida.
What roofing materials does Montgomery Winslow Roofing install?
The company works with asphalt shingles, tile, metal, and flat/single-ply roofing systems, including Polyglass products for flat and low-slope applications.
What are Montgomery Winslow Roofing's business hours?
Montgomery Winslow Roofing is open Monday through Friday, 9:00 AM to 5:00 PM, and is closed on Saturday and Sunday.
Who owns and operates Montgomery Winslow Roofing today?
The Woolston family has owned Montgomery Winslow Roofing since 1990. F. John Woolston currently leads the company, with Kathleen Anne Woolston serving as the qualifying license holder.
How can I get a quote from Montgomery Winslow Roofing?
Call Montgomery Winslow Roofing at (239) 694-1056, email info@montgomerywinslow.com, or visit montgomerywinslowroofing.com to request a quote.