Robert Dowling

Helping Naples Clients for over 42 Years !  

Rob Dowling has been in Naples, Florida Real Estate over 42 Years since coming to the area in 1982 and now with Over 650 Naples transactions as a single agent.

Personally hired at prestigious Wyndemere by Canadien Developer Gerry Livingston (Livingston Road) in 1982 as the Tennis Pro and Management Team member to oversee the tennis, swim and fitness operations. Wyndemere is the high-end golf and country club real estate development

Helping Naples Clients for over 42 Years !  

Rob Dowling has been in Naples, Florida Real Estate over 42 Years since coming to the area in 1982 and now with Over 650 Naples transactions as a single agent.

Personally hired at prestigious Wyndemere by Canadien Developer Gerry Livingston (Livingston Road) in 1982 as the Tennis Pro and Management Team member to oversee the tennis, swim and fitness operations. Wyndemere is the high-end golf and country club real estate development with 27 championship holes, tennis stadium, luxury spa , resort pool, and new pickle complex. After making it Naples' best tennis facilities in five years, Rob moved into the Wyndemere Real Estate Division for seven years selling over 150 homes.

Rob's knowledge, experience and Naples success has afforded his clients the information they need to make the right decisions in the sophisticated Naples market. As a 20 year Wyndemere member and resident, he's sold over 325 homes in this fine community, along with fine condominiums and homes in high-end golf and tennis areas such as Gulf Shore Boulevard and other popular Naples communities.

Rob is a Broker, a 39-year Naples agent (32 years with John R. Wood Christie's International Real Estate), past Board Of Director at John R. Wood, the #1 Real Estate Brokerage in Southwest Florida and 35th largest nationally. Rob is rated a Five Star Agent by Gulf Shore Magazine and a Hall of Fame inductee. 

From Cleveland, Ohio, R$ob was the Naples City tennis champ (pro division), USPTA Tennis Pro, Member of Team Naples at the USPTA Nationals, played Division 1 college tennis and captained Bowling Green with wins over Ohio State, Notre Dame, Penn State, Miami, Cincinnati and named to the Ohio Junior Davis Cup team.

Rob’s wife, Mikki, assists in the business and grew up in Naples and Chicago. She previously owned the family’s 20-acre golf business in Naples, The Blue Caribbean driving range—opened in the 1950s and located on U.S. 41 next to Coastland Mall—as well as the Ikki Mikki retail store on Fifth Avenue. Their daughter, Grace, was the Florida State High School Tennis Champion at Naples’ Barron Collier High School, went on to star in collegiate tennis at Lake Forest College in Chicago, earned a master’s degree from Georgetown University, competed professionally with the ATP and WTA, and now works with the Tampa Bay Rays Baseball Organization.