Kennedy Investments is a family owned and operated real estate investment firm with a long history of investing in Florida.

After 5 years in the Miami real estate market, David Kennedy and his business partner, Mike Frost, took a leap of faith and in 1975, they moved their commercial real estate company back to David’s hometown with the help of one of their investors, Tampa businessman and philanthropist, Hinks Shimberg.

Their portfolio included apartments, industrial buildings, retail centers, and land development deals ranging from Jacksonville to the Tampa Bay region. In the 1980’s, their holdings grew to include the Orlando market when they bought the Royal Plaza Hotel and also built the 1,000 room hotel, Buena Vista Palace; both located in Disney World’s Lake Buena Vista area. Over the years, the partnerships changed and each decided to focus on their individual areas of expertise. It was then that David founded Kennedy Investments in 1986.

Jay Kennedy began his real estate career in Tampa Bay in 1995 and chose to join the family firm in 2001, bringing diverse commercial real estate experience ranging from investment brokerage to retail and office development. Jay Kennedy bought the company from his father in 2011. Over his twenty-plus year career, he has completed more than $500,000,000 in real estate transactions, executed hundreds of commercial leases and completed several commercial developments.

Throughout different economic cycles, Kennedy Investments has owned and managed retail, office, multifamily and industrial properties, among others. We believe that all commercial property types can provide superior returns with sound acquisition strategies and exceptional property management. The firm invests throughout the greater Tampa Bay area, but has also developed, owned and managed around the state, including in the Jacksonville, Ocala, Fort Meyers and Orlando areas. In addition to our own portfolio, Kennedy Investments provides property management services to select 3rd party commercial real estate owners in Tampa Bay. We are committed to providing the same level of attention, detail, and expertise to our clients that we give our own properties.

Today, Kennedy Investments manages over 1,000,000 square feet of real estate assets in the Tampa Bay region, valued in excess of $200 million. Although we have been successfully investing in Florida for more than 50 years, our strategy remains the same: to provide our clients superior returns while minimizing their exposure to the risks of commercial real estate investing.


David Kennedy

Founder (Retired)

Learn More


Ryan Hutkowski

Director of Leasing and Brokerage

Learn More
Christopher Leandri

Director of Asset Management

Learn More