• 239-766-4202
  • Year Established: 1949
  • Homeowners Served: 50,000+
  • Number of Employees: 12+
  • License Number(s): CCC052474
"In 1990, the Woolston family purchased Montgomery Winslow Roofing, founded in 1949, serving Lee, Charlotte, and Collier counties. Whether you are repairing or replacing your roof, no job is too big or too small for our professional, courteous staff of factory-trained installers, all covered by our workers' compensation and general liability insurance. We provide trained, uniformed professionals who are drug and background checked, never using day laborers. We will help you overcome any roofing challenge you may have."

John Woolston, Owner
Principal Owners / Key Managers
John Woolston, Owner
Brad Woolston, Manager
Orlando Calderon, Manager
Melissa Smith, Manager
Five Star Guarantee
We stand behind every Five Star Rated company with Our Guarantee. We've done the research for you and identified the best home service pros in your neighborhood.
Homeowner Reviews

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

“Excellent job! They have pride in their work and do what is needed. Good communication with the owner and office personnel.”

“Good attention to details and prompt answers to my questions. Honest and good value for their quality work.”

“Family customer since the 1950's. Earnest workers who know their trade. Good job.”

  • 239-766-4202
  • Year Established: 1949
  • Homeowners Served: 50,000+
  • Number of Employees: 12+
  • License Number(s): CCC052474
"In 1990, the Woolston family purchased Montgomery Winslow Roofing, founded in 1949, serving Lee, Charlotte, and Collier counties. Whether you are repairing or replacing your roof, no job is too big or too small for our professional, courteous staff of factory-trained installers, all covered by our workers' compensation and general liability insurance. We provide trained, uniformed professionals who are drug and background checked, never using day laborers. We will help you overcome any roofing challenge you may have."

John Woolston, Owner
Principal Owners / Key Managers
John Woolston, Owner
Brad Woolston, Manager
Orlando Calderon, Manager
Melissa Smith, Manager
Top Company Features
  • Five Star Guarantee
  • Licensed
  • General Liability Insurance
  • Workers' Compensation Insurance
  • Employees Background Checked
  • Employees Drug Tested
Services Offered
All roof types; shingle, tile, metal, and flat
Commercial and residential
Roof leak repair, roof replacement, and new construction
Roof inspections
Maintenance service agreements
Emergency response
Insurance
General Liability & Workers' Compensation
Warranties / Guarantees
Ten-year warranty on re-roof installations
No deposit required
Recognitions
Florida Roofing and Sheet Metal Contractors Association (FRSA) member
Kiwanis Club member since 1996