In 2015, Mark Pentecost paid $14.5 million for a 104-acre Florida island; after pouring millions into upgrades, it is asking $89 million with a 9-hole golf course and 29 developable lots
Eleven years after buying a private retreat off Florida’s west coast for $14.5 million, entrepreneur Mark Pentecost has listed the 104-acre property for $89 million after spending millions on its transformation. The estate, historically known as Little Bokeelia Island, was listed through Coldwell Banker Realty and featured in Realtor.com’s round-up of high-value American homes. The sharp rise in its value follows major improvements, including a private nine-hole golf course, upgraded infrastructure and 29 developable residential lots.
From classroom teacher to island owner
Pentecost, a former high-school mathematics teacher and basketball coach, made his fortune after founding the multi-level marketing company It Works! in 2001. The health and beauty business grew into a company worth hundreds of millions of dollars, allowing Pentecost and his wife, Cindy, to buy the island in July 2015. The couple paid much less than the property’s original asking price of $29.5 million. At the time, the sale was recorded as one of the most expensive residential property deals in South-West Florida. Speaking shortly after the purchase, Pentecost described his vision for the private retreat. “Little Bokeelia is a slice of paradise that allows you to enjoy friendship, fun, freedom and to unplug from the chaos of today,” Mark Pentecost said in a statement released at the time. “It’s in these moments when you’re able to relax that you can brainstorm and innovate.”
Historical roots and modern upgrades
Located in Pine Island Sound between Sarasota and Naples, the island has a history dating back to the early 20th century. Industrialist and dry-cell battery inventor Charles Frederick Burgess bought the property in 1924 and built a Spanish-style villa in 1928. He hosted notable guests there, including inventor Thomas Edison. During his 10 years of ownership, Pentecost transformed the island into a fully equipped corporate retreat and family compound. The estate is centred around the restored 1920s Addison Mizner-style main mansion, along with four guest cottages, a clubhouse, a caretaker’s home and several recreational facilities. Together, the buildings contain 11 bedrooms, 10 full bathrooms and three half-baths. Along with the new nine-hole golf course, the property now has a pickleball court, full tennis and basketball courts, four deep-water docks, a resort-style swimming pool and a commercial-grade helipad for travel to and from the mainland. Property records from listing brokerages Coldwell Banker Realty and SWFLMLS show that the estate covers 104 acres with a large amount of shoreline. The 29 subdivided, developable lots could allow a future owner to turn the private island into an exclusive residential community or keep it as one large estate.
Market positioning
With an asking price of $89 million, Little Bokeelia Island is now among the most expensive private island properties listed in the United States. Property records show annual taxes of about $115,166. Although the island is secluded and can only be reached by helicopter or boat, it is close to deep-water tarpon fishing and coastal areas near the historic Gasparilla Inn on nearby Boca Grande. Coldwell Banker and Pentecost’s representatives have not publicly said whether the property will be sold as one unplatted parcel or whether developers will be able to buy individual subdivided lots. The sale is one of the most notable private island property offerings on the Gulf Coast in recent decades.
