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Caldwell Roofing

Boca Raton
Licensed & insured DBPR verified
Roof RepairRoof ReplacementNew Roof ConstructionRoof Inspections+4 more
4.932 Google reviews
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About

Caldwell Roofing is a State of Florida certified roofing contractor based in Boca Raton with more than 40 years of professional roofing experience in South Florida. The company is family owned and operated under the leadership of President Jon Milanese, providing daily hands-on management on every project. Caldwell Roofing handles residential and commercial roof repairs, replacements, and new construction using its own in-house crews without subcontractors. Its primary service area spans Boca Raton, Boynton Beach, Delray Beach, and surrounding Palm Beach and Broward County communities.

Highlights

Over 40 years of professional roofing experience in South Florida
Family owned and operated with daily on-site management
All work performed by in-house crews — no subcontractors
State of Florida certified roofing contractor (CCC-033696)
Comprehensive insurance exceeding Florida state minimums

Services

Roof Repair
Roof Replacement
New Roof Construction
Roof Inspections
Reroofing
Residential Roofing
Commercial Roofing
Emergency Roof Services

License verification

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

CompanyCaldwell Roofing
License typeCCC, Certified Roofing Contractor
License no.CCC033696
Status Active & current
License boardFL DBPR
RegionBoca Raton
DBPR verified Licensed in FL

Confirm this license yourself at myfloridalicense.com.

Google reviews

4.9
Rated by 32 verified Google reviewers Verified by Google
Charles Chase· 7 months ago

I could not be happier with the work performed by Caldwell Roofing. From the owner to the site supervisors, project managers, and the crew, every member of the team was exceptionally professional. They were respectful of our property and our condominium owners, keeping the worksite clean and organized throughout the entire project. Jon & Josh completed the project ahead of schedule and was more than fair in pricing the necessary change orders, which were due to significant termite damage in the original roof structure. If you are looking for a reputable, honest roofing company that provides excellent work at a fair price, I highly recommend Caldwell Roofing.

Michelle LaMorte· a year ago

I recently had my concrete S tile roof installed by Caldwell Roofing, and I couldn't be happier with the results! From start to finish, their professionalism, expertise, and attention to detail were truly top-notch. The team worked efficiently and ensured everything was done with precision, using a high-quality Polyglass underlayment that gives me peace of mind about durability and protection. Throughout the process, communication was excellent. They kept me informed, addressed any concerns promptly, and delivered exactly what was promised. The craftsmanship speaks for itself—my roof looks fantastic and is built to last. If you're looking for a reliable and skilled roofing company, I highly recommend Caldwell Roofing. Exceptional service and quality workmanship!

Christopher Hibbard· 3 months ago

Did my replacement roof 22 years ago and now made some repairs. Incredibly professional. Nothing needed to be cleaned up after them. All my neighbors using them have the same experience. Highly recommend

Thomas Stallone· a year ago

Caldwell Roofing swiftly replaced the roof of my HOA 2200 SQFT home, their team was very communicative. There was no check list in the end because the job came out perfect the first time. I am very happy with their services, and their pricing was very reasonable. I live in Delray Beach next to the Medical Center.

Hunter Pearl· a year ago

John, Josh, and their crew were fantastic. Needed roofing repairs done to satisfy insurance in a very short amount of time and they were able to get it done in just a few days. They were on top of everything, great communication, and follow up. Price was extremely fair, especially compared to other companies in the area. Can’t recommend them enough!!

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Verification badges

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

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Frequently asked

What is Caldwell Roofing's Florida license number?
Caldwell Roofing holds Florida Certified Roofing Contractor license CCC-033696, issued by the Florida Department of Business and Professional Regulation.
How long has Caldwell Roofing been in business?
Caldwell Roofing has been providing professional roofing services in South Florida for more than 40 years.
Does Caldwell Roofing use subcontractors?
No. All work is performed by Caldwell Roofing's own skilled employees to ensure a consistent, high standard of quality on every project.
What types of roofing services does Caldwell Roofing offer?
Caldwell Roofing offers roof repairs, roof replacements, new roof construction, and roof inspections for both residential and commercial properties.
What roofing materials does Caldwell Roofing work with?
The company works with asphalt shingles, clay tiles, flat roofing systems, and metal roofs, guiding clients in selecting the best material for Florida's climate.
What areas does Caldwell Roofing serve?
Caldwell Roofing is based in Boca Raton and services Boynton Beach, Delray Beach, and communities throughout Palm Beach County and Broward County, including Fort Lauderdale and Parkland.
Is Caldwell Roofing insured?
Yes. The company carries comprehensive general liability insurance with coverage limits that exceed Florida state mandates, and all employees are covered by Workers Compensation insurance.
Does Caldwell Roofing require a large deposit upfront?
No. Caldwell Roofing requires only a small upfront deposit to cover the permit application and filing process, funding all construction operations from its own financial resources.
Is Caldwell Roofing licensed at the state level or only locally?
Caldwell Roofing is fully licensed by the State of Florida, not merely at the county level, which allows the company to work throughout the state.
How do I get a quote from Caldwell Roofing?
You can call Caldwell Roofing directly at (561) 392-0971 or submit the free quote request form on caldwellroofing.com.