Ex-Playboy president lists Siesta Key retreat
Nearly completed home has a $19.95M price tag
A Siesta Key property owned by the former president of Playboy Entertainment has been listed for sale for $19.95 million.
The owner, Randy Nicolau, bought the site in 2018 for $2.5 million, according to Sarasota County property records. The home was a personal retreat, but the entrepreneur demolished it in 2022 and appears ready to capitalize on the rapid rise in Sarasota real estate value.
Construction is expected to wrap up at 5151 Jungle Plum Road in Siesta Key’s Hidden Harbor community for what is described in marketing materials as an “exquisite waterfront property.”
Nicolau was the president of Playboy Entertainment from 2001 to 2005. After his stint at Playboy, the Harvard University graduate founded two successful companies, including most recently Poppin, which was acquired by Kimball International in 2020.
The eye-catching nearly $20 million price tag for the property ranks among the most expensive in the region, just below a $22 million listing at 3799 Flamingo Ave. on the north end of Siesta Key and a $21 million listing at 8250 Sanderling Road.
But both are well behind the $33.8 million listing that hit the market in September for a newly constructed home in the Harbor Acres neighborhood.
While the Sarasota real estate market has seen some moderation in prices, closed sales are well behind last year, though a luxury property sold in 2023 on Lido Key for nearly $14 million.
Joel Schemmel, a Realtor with Premier Sotheby’s International Realty’s Downtown Sarasota office, listed the property on Jungle Plum Road for sale.
When completed, the residence will total 8,165-square with six bedrooms and six bathrooms. The boat dock has water deep enough for yachts, according to the listing.
“Step into unparalleled luxury at this Siesta Key waterfront retreat within the esteemed Hidden Harbor community,” marketing material reads. “Truly the perfect combination of architectural significance and an extraordinary site — the result being awe-inspiring positive energy accentuated by extensive bay views that stretch all the way to Sarasota’s downtown skyline.”
Sarasota-based DSDG Architects provided design services for the property in the Hidden Harbor community.
“This Siesta Key gem is situated in a charming old-Florida style community, a boater’s paradise mere moments from award-winning white sandy beaches,” Schemmel said. “The home, currently undergoing meticulous construction, promises an unparalleled living experience, marked by architectural significance and an exceptional location.”