The Tradewind Legacy

The Tradewind Estate Homes Legacy

Tradewind Estate Homes is remembered for friendly, quality workmanship across Cape Coral and Southwest Florida.

The DePaola-era company history included residential remodeling, commercial remodeling, new construction, additions, kitchens, baths, office build-outs, outdoor living spaces, pool areas, structural work, and custom homes planned around each client’s needs.

DePaola Family Construction Roots

The Tradewind story was connected to DePaola Bros. Construction, a family construction company originally established in Fall River, Massachusetts, by brothers Walter and Joseph DePaola.

Walter’s son, Tom DePaola, brought that family construction tradition to Cape Coral in 1979.

Tradewind Estate Homes in Cape Coral

After moving to Cape Coral, Debi and Tom continued the DePaola family’s building tradition in Southwest Florida.

Debi joined the company, learned the industry from the ground up, studied construction, received her Building Contractor license in 1988, and established Tradewind Estate Homes.

Together, Tom and Debi built many commercial and residential projects in Cape Coral and throughout Southwest Florida.

Built with Pride, Skill, and Experience

Tradewind Estate Homes was remembered for craftsmanship, planning, reliability, and a hands-on approach.

Tom was known for being on the job himself, personally working on homes and insisting on the best from employees and subcontractors. Debi and the office team helped guide projects through planning, permits, client communication, and the many details that bring a project together.

Timeline

pre-1979

Fall River, Massachusetts

The DePaola construction story began before Tradewind Estate Homes. DePaola Bros. Construction was established in Fall River, Massachusetts, by brothers Walter and Joseph DePaola.

1979

Cape Coral Begins

Debi and Tom DePaola moved from Tiverton, Rhode Island, to Cape Coral, Florida, in 1979.

Together, they raised three sons in Cape Coral. Tom also brought the DePaola family construction tradition to Southwest Florida.

March 1988

Debi Earns Building License

After working in construction with Tom and learning the industry from the ground up, Debi earned her Building Contractor license in 1988.

Her licensing marked an important step in carrying forward the DePaola family construction tradition.

October 1990

Tradewind Estate Homes Is Established

In October 1990, Debi and Tom established Tradewind Estate Homes.

From that point forward, Tradewind Estate Homes became part of the DePaola legacy, remembered for quality workmanship and honest service.

1990s

Community Roots

Debi and Tom became members of St. Katherine Drexel Catholic Church when the church began in 1990. They were also connected to St. Andrew Catholic Church, St. Andrew Catholic School, youth organizations, the CCCIA, and the Cape Coral Chamber of Commerce.

2009

Semi-Retirement

Debi and Tom DePaola semi-retired from construction, leaving a legacy of honesty, dependability, craftsmanship, respectful crews, attention to detail, and long-term trust.

April 2019

Remembering Tom DePaola

Tom DePaola passed away in April 2019.

His memory remains part of the DePaola family’s Cape Coral story and the legacy of Tradewind Estate Homes. Through his work, relationships, and commitment to building things the right way, Tom left a lasting mark on family, clients, friends, and the Southwest Florida community.

December 2021

Remembering Debi DePaola

Debi DePaola passed away in December 2021.

Debi’s legacy lives on through her family, her community, and the company history she helped shape. As a Building Contractor and the cofounder of Tradewind Estate Homes, she carried forward the DePaola tradition of pride, skill, experience, and care for the people behind every project.

walter and joe depaola friendly pose on a sunny porch — The original DePaola brothers, Walter and Joe DePaola

tom and steve depaola — Walter DePaola’s son, Tom, and Joe DePaola’s son, Steve. The descendants of the original DePaola brothers.

depaola bros rustic red chevrolet in rural setting

worker on ladder at construction site — Tom DePaola was known as an expert framer.

roof work — There were few things Tom DePaola didn’t do on the jobsite. Whether it was framing, masonry, roofing, plaster, tile, painting, or finish carpentry, Tom took pride in every aspect of his work.

The DePaola tradition was simple:

Build it right and build it to last.

This memorial archive preserves that tradition and the people behind it.

View Project Archive