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Welcome to R.W. Caldwell Realty & Insurance

RW Caldwell RealtorsFounded originally in 1937, locally owned and operated R.W. Caldwell, Realtors® and Insurors, is a fourth generation family business. R.W. Caldwell is now Pinellas County's oldest real estate company and is the City of Gulfport's oldest business.

We are very grateful for the trust so many families have given us in the buying or selling of their homes over the many decades that has made us the Gulfport, Pasadena, Southwest St. Petersburg area's leading real estate agency in number of sales, year after year cumulatively. For this faith and reliance we are very honored. We strive daily to live up to the confidence with which we have been entrusted.

We also offer Full Service Property Management and Home, Auto and Business Insurance. Our basic philosophy is to treat everyone we have the chance to serve with hard work, respect and appreciation. We try very hard to live up to our registered service mark, "The Service That Satisfies"sm.

Whether you are buying, selling or renting real estate or in need of home, auto or business insurance, we would be very pleased to serve you. We're here to help. Thank you.

About Us

Founded originally in 1937, locally owned and operated R.W. Caldwell, Realtors® and Insurors, is a fourth generation family business. R.W. Caldwell is now Pinellas County's oldest real estate company and is the City of Gulfport's oldest business.


R.W. Caldwell Park

The entire Caldwell Family was truly honored and appreciative when three generations of R.W. Caldwell’s were recognized by the city of Gulfport with the naming of the park off 64th Street and Gulfport Boulevard in their honor on April 18, 2009. You can view the dedication ceremony here.


Recent Listings

$750 /month

5211 Gulfport Blvd S ,Gulfport FL, Office Space

1 Bedrooms | 1 Bathrooms | Office

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$1,100 /month

7625 Sun Island Drive S,Unit 403, South Pasadena FL, 55 Plus Waterfront Furnished Condo - Annual Rental

1 Bedrooms | 1 Bathrooms | Condo

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$1,275 /month

701 75th Ave N, Saint Petersburg FL, Block Home Located In the Fossil Park Neighborhood

2 Bedrooms | 1 Bathrooms | Single Family

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