• 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
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Homeowner Reviews

“The workers were exceptionally meticulous and truly took extra care to not leave anything behind, from tear off to shingles. His suggestion turned out wonderfully.”

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

“This company rates a five-star-plus rating. Everything was completed as promised and then some. They were very helpful in selecting the style and color of tile that went perfectly with the exterior of our home.”

  • 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
Services Offered
All Roof Types; Shingle, Tile, Metal, Flat
Roof Leak Repair/Replacement and New Construction
Commercial and Residential
Roof Inspections, Maintenance Service Agreements, Emergency Response
Insurance
General Liability & Workers' Compensation
Warranties / Guarantees
10 Year Warranty on Re-roof Installation
No Deposit Required
Recognitions
Florida Roofing & Sheet Metal Association Member
Kiwanis Since 1996