Our History
RW Caldwell Realty
A Tradition of Excellence Since 1937
Founded in 1937, R.W. Caldwell Realty is a family-owned and operated real estate, insurance and property management company. The business dates back to 1935 when our founder began in insurance before opening R.W. Caldwell Realty and Insurance in 1937. RW Caldwell is the longest-standing real estate firm in Pinellas County and the longest-
Longevity in the city accounts for much of the firm’s success.
The Legacy of R.W. Caldwell Sr.
R.W. Caldwell Sr. became known as the “father” of Gulfport’s beach after he proposed and then helped pay for a dredging project that created the sandy strip along the Boca Ciega Bay shoreline.
The Leadership of R.W. Caldwell Jr.
R.W. Caldwell Jr. came back to Gulfport in 1951 with his wife Adele and their three children. His plan was to work with his Dad and open the building division of R.W. Caldwell, Inc., a real estate and insurance business originally started by his father in 1937. In late 1952, Bob found himself running the entire company after his father's untimely death. He was a successful investor and land developer and was elected in 1954 President of the Contractors and Builders Association of Pinellas County. Bob was the first President of the Gulfport Chamber of Commerce and was President of the Friends of the Gulfport Library when the new library was built at 28th and Beach Boulevard.
July 9, 1943 – April 2, 2025
In Loving Memory of Poul Hornsleth
Poul Hornsleth was born in 1943, in Orange, New Jersey. Poul was named after his father and proudly embraced his Danish heritage and its spelling of 'Poul'. He graduated from the Wooster School in Danbury, CT and later graduated from the Ivy League University of Pennsylvania where he met the love of his life, April Caldwell. They were married for 56 years.
A Commitment to Civil Rights
After college, Poul began his lifelong dedication to civil rights by teaching high school mathematics at Edison High School in inner city Philadelphia. His work as an educator inspired his ongoing involvement with the NAACP, where he remained a steadfast advocate for expanding access to opportunities and educational choice for all.
Leading the Family Business
In the early 1970s, Poul and April moved to Gulfport, Florida, her hometown, where they took over R.W. Caldwell Realty and Insurance which was founded by her grandfather in 1937, and is now the oldest real estate office in Pinellas County. Poul and April led the business with integrity and vision, becoming respected leaders in the community. Poul blended his civic-minded ideals with a deep commitment to the local area, proudly promoting both boys' and girls' Caldwell sponsored Little League teams for more than 50 years. Poul was also a keen supporter for many years of the Gulfport Lions Club and Keep Pinellas Beautiful among many other local organizations, schools and events that took place in Gulfport.
Belief in Education
He believed deeply in the promise of America, the country's potential and the rewards that hard work could bring. Just as strongly, he believed in the power of education. "You only get one chance to educate your kids," he often said. He lived by that conviction, sending his son, Poul III, and daughter, Jody, to New England preparatory schools and later to the University of Michigan Ann Arbor and Columbia University in the City of New York, respectively.
Passing the Torch
Poul took great pride in passing the family business, Gulfport's oldest, to the fourth generation when his daughter Jody assumed leadership of the real estate and property management divisions, while her husband Rob oversaw insurance. Working alongside them every day brought him great pleasure, and he cherished the opportunity to see them and members of the Caldwell family all grow the firm together.
A Devoted Grandfather
Later in life, Poul found immense joy in becoming a grandfather. He was a devoted and playful presence in the lives of his granddaughters, Sarah and Cecilie, daughters of Jody and Rob, who affectionately called him 'Chi Chi.' Poul delighted in giving each of them special nicknames and making up songs just for them. His joy grew even deeper this past Christmas when his daughter-in-law, Rita, surprised him with the news that his expected grandson, born in January, would carry on his name as Poul IV. Being able to spend the last few months of his life seeing his newborn grandson was truly a blessing.
A Lasting Legacy
Poul Hornsleth leaves behind a legacy of love, patriotism, and the unwavering belief in doing what is right. He will be remembered for a life well-lived, and the values he passed on to the generations that follow.
Today’s Caldwell Realty
Caldwell Realty operates from an old house on Gulfport Boulevard. The lobby walls are adorned with a huge, mounted tarpon that was dispatched with a hammer after it jumped into a boat and aerial photos of the Gulfport area dating back to the early 1900s.
In addition to Gulfport, the agency handles property in southwest St. Petersburg and South Pasadena. The firm is a full-service agency, doing residential and commercial (transactions) and manage about 300 rentals, in addition to insurance.
The agency has continued its tradition of community involvement by supporting youth baseball and other Gulfport activities.
