Your Roofing Professional For Over 35 Years

Testimonials –

Welcome to Caldwell Roofing. South Florida’s premier residential Roofing Contractor for over 35 years. Based in Boca Raton, we pride ourselves on being the most respected Professional Roofing Contracting company in South Florida.

Dear Jon,

I can not say enough good things about Caldwell Roofing.

You have to be the very best roofers around. Truly a team of great professionals from top to bottom. Genuinely care about there customers. Top quality workmanship. They are honest, reliable and conscientious.

I would not every consider using any other roofer than Caldwell Roofing when ever I have a roofing problem. You are great people and do a great job. You are truly the best.


Burt Katzman
Polo Club
Boca Raton, FL

Many thanks for your fine workmanship and work ethics! Our roof looks beautiful.

Ray & Annie North
Boca Raton, FL

Dear Caldwell Team:

Yesterday, your firm completed the installation of our new tile roof. I wanted to share some thoughts on this experience.

After receiving quotes and sales pitches from several roofing companies my wife and I visited Caldwell Roofing. Your staff was the most professional we had encountered.

From the first minute the crew arrived to remove the old roof my wife and I were impressed; so were our neighbors. The courtesy, work ethic and craftsmanship of every single Caldwell crew member brought a smile to our faces. There were no delays.

My wife and I extend our thanks and appreciation for the care, courtesy, professionalism and timeliness exhibited by everyone at Caldwell Roofing. We will, with great confidence, heartily recommend Caldwell.


Joe & Diana Schmoke
Boca Raton, FL


We have encouraged some of our neighbors and fiends to use Caldwell for their new roofs or repairs because of your service, reputation, quality workmanship, and attitude of your employees.

Jon, we saw many houses in our development where the roof was left with tar paper or even tiles piled on it for months. Trash containers filled driveways with ladders left leaning on houses, all for a considerable period of time.

Not so your people or schedules. Everything Caldwell did, from start to finish, was done in a prompt, workman like manner without failing to very carefully cleaned up during and after every day’s efforts.

Please thank your “crew” for us on a job well done and Tammy who picked out the tile which looks great. Happy to “show” our roof to any customer.


Dolores and Jerome Bartzoff
Delray Beach, FL


I want to take a minute to thank you and Tammy for the courtesies you extended to me and my wife, Dorothy during our visits to your business.

Its nice people like you and Tammy that make doing business with you very enjoyable.

Wishing you all the best now and in the future.

Warmest Regards,

Rich Neubauer
Deerfield Beach, FL

Dear Jon and Tammy,

Before much more time elapses, I want to write this letter of appreciation. Choosing your firm to repair the damage to my roof, incurred by Hurricane Wilma, could not have been a better one.

All of your employees, under the supervision of Steve, deserve recognition, not only for the excellent results, but for their cooperative spirit and relationship. Having been a manufacturer of promotional advertising products for over 50 years, employing 400 people, I personally know the importance of on going relationships and attitude.

My wife Sarah, joins me in expressing “Thanks, for a job well done”.

Isreal Margolies
Boca Raton, FL

Dear Jon,

Your company has recently completed the installation of a new tile roof on our home in Boca Raton. We are happy to tell you that the experience has been totally positive and trouble free.

We were not looking forward to the enormous step of replacing our roof as so many of our neighbors had had a great deal of aggravation and disappointment with quality, construction time, reliability, etc. We consider ourselves so very fortunate to have found and hired Caldwell Roofing.

You alleviated our concerns from the onset when you came to our home, explained the entire process, and answered all of our questions in a professional and courteous manner. We were very comfortable as clients when we came to your office and signed our contract.

The time frame you projected was on target, and once the job began, it was completed by capable teams of men under judicious supervision. Stephen Rubino checked on his tears often and communicated with us explaining the process and answering all concerns cordially and effectively.

We are very happy with our new roof and thank you r entire company and its employees for their fine workmanship under excellent leadership.

Marilyn Brodsky
Marilyn and Sanford
Boca Raton, FL

Dear Jon and company,

I want to thank you for a job well done! My roof is beautiful. I could not have asked for better service and truly professional.

Thank you again,

Judy Mershimer
Delray Beach, FL

Dear Jon,

I wanted to drop you a note to tell you how impressed we are with Caldwell Roofing. The guys were fantastic, friendly, answered all of our questions, and even did a couple of extra things that weren’t a part of the contract. The workmanship is outstanding, the roof looks great, and we are extremely satisfied.

Thanks for everything,

Tim and Cindy Wade
Lighthouse Point, FL


The partnership between Willoughby Supply and Caldwell Roofing over the past 3 years has grown beyond just two companies doing business. The professionalism and commitment to customer service from you and all your employees is much appreciated. Your hands on leadership as an owner and experienced in the South Florida market make Caldwell Roofing a valued business partner now and in the future.


Chris Meister
Florida Manager
Willoughby Supply of Florida

Dear Jon,

I wanted to let you know how pleased and impressed we are with Caldwell Roofing. The crew was extremely clean and kind, and their attention to detail was awesome!

Thanks again for delivering beyond expectation.

Kevin Pearson
Boca Raton, FL

…We have worked with the staff of Caldwell Roofing on several projects, both major and minor in size, and are always greatly appreciative of their willingness to go the extra mile to satisfy our needs. Caldwell Roofing makes every effort to remove any potential “inconvenience” while performing their work, which is not always easy at a facility such as ours.

Ronald J. Tobias, Executive Pastor
Spanish River Church

…I consider Jon Milanese and Caldwell Roofing to be one of the most trustworthy professional business associates in our area.

Bob Powers
House Captains, Inc.

Dear Caldwell Roofing,

We are thoroughly pleased with our service from Caldwell Roofing. While we were appreciative of the fair content price, the high level of integrity, communication, and follow up was simply outstanding

Pat Sklar
Atrium Condominium Association

Dear Jon,

After 20 years of doing business with the staff at Caldwell Roofing, we have realized that companies maintaining a first class commitment to their customers directly affects their ability to maintain the same financial commitments to their suppliers. Caldwell Roofing is one of the best in the roofing industry at achieving these goals.

Customer satisfaction and an incredible understanding of putting on a quality roof is something that you have very little competition on. Keep doing what your doing.

Bob Landrum
Florida Regional Manager
Bradco Supply Corporation

Dear Jon,

You guys rock! Great roof! Thanks!

The Kaskys
Boca Raton, FL

To: Tammy, Jon, Steve, Seth, and Colleen

What an awesome team you all are! We are completely pleased with our new, beautiful roof! You all were so responsive to our needs and concerns. We truly appreciate your professionalism and attention to detail.

We couldn’t believe how clean the exterior of our house was each evening.

Thank you for making the entire process a pleasure. Tammy, your willingness to ride around the neighborhoods to identify the roof tiles I liked was amazing. Also, thank you for taking the time to explain the roof replacement process to me. It feels good to understand the work that is being done. Seth, thanks for keeping us dry as we waited for the rains to pass so we could replace our ailing roof. Jon and Steve, thank you for responding quickly to our concerns as they arose. Colleen, thank you for your kindness thought the process.

Please share with all the men who worked so hard in the hot sun throughout all the phases that we appreciate their fine work and positive attitudes.

Thank you again for your excellent work!

Blair Nadel
Boca Raton, FL

Dear Steve:

We wanted to let you know how much we appreciate our beautiful new roof.

You led your crew in working in a professional, courteous, diligent and timely manner. Every evening they cleaned up after themselves and even used a magnet to locate any nails and/or metal pieces left behind. It was especially nice not to have to have a dumpster in our driveway every evening.

Thank you so much for making this experience positive. We had heard from neighbors of their nightmare roofing stories and we were not looking forward to the process. Caldwell proved to be a great choice for us.

Thank you Again and Good Fishing to You,

Cheryl and Jeff Dean
Boca Raton, FL

Dear Jon:

I want you to know how pleased I am with the quality of work that was done when your company installed by new roof several years ago.

The last two hurricane seasons were quite a test.

In 2004 I sustained no damage at all. In 2005 aside from small damaged caused by flying debris, I did not lose on tile!

Should you ever need a recommendation don’t hesitate to use me as a reference.

Sincerely yours,

Alan L Winniman
Boca Raton, FL


South Florida’s premier residential Roofing Contractor for over 35 years.

Based in Boca Raton, we pride ourselves on being the most respected Professional Roofing Contracting company in South Florida.