Sarasota has long lured the gifted and creative to its Gulf of Mexico shores. Perhaps it’s the turquoise-tinged water, the white-sand beaches or maybe those coastline-hugging barrier islands that inspire the imagination and even lead to reinvention. It happened to Californian Kathy Kittinger, a corporate executive turned photographer, who followed family here in 2005 and quickly piqued local curiosity as she converted the grounds of a bungalow in the Towles Court arts colony into her outdoor garden studio. “Everyone wanted to come in and stay,” she says. “Then they wanted to buy my accessories and furniture.” The Garden Room (a small, quaint cafe and gift shop) at Shoogie Boogies was born. “I never dreamed I’d be a photographer, let alone a cafe owner,” she says.
Dreams, however, are the stuff of Sarasota history. Its earliest pioneers arrived in the 1840s, tempted by water teeming with fish and prospects of cattle and citrus farming. Soon the city began enticing wealthy wintertime residents like John and Mable Ringling. The circus king of America was an avid land developer of the Sarasota Keys in the 1920s; the Ringlings were also passionate art collectors. Their bayside home, Cà d’Zan, and the John & Mable Ringling Museum of Art remain city landmarks.
“Sarasota has always had a sought-after lifestyle,” says Michael Moulton, a realtor with Michael Saunders & Co. “Sarasota has the amenities and culture of a city of 1.5 million people [although it has just under 52,000 residents], and buyers get more bang for their buck here,” Moulton says. “We’re on the radar for anyone considering Florida as the place to retire or semiretire.” That was the case for noted author John Jakes, who made the transition from winter resident to full timer last December. “Sarasota’s professional theaters are first-rate and the quality of our opera house is incredible for a small city,” says Jakes, whose Civil War series was adapted into the 1980s TV miniseries North and South. “I always thought I’d end up here.”
Explore Sarasota and Her Islands
Sarasota’s five main barrier islands — Longboat, Lido, St. Armands, Bird and Siesta — are called keys. Connected to downtown by the John Ringling Causeway, here wealthy, often famous, residents live nestled between Sarasota Bay and the Gulf beaches. Northernmost Longboat Key boasts prime real estate, reinforced by limited public beach access and the Longboat Key Club & Resort where annual and seasonal memberships are available to nonresidents. Longboat, Moulton explains, also has less traffic than Lido and Siesta, which have large public beaches.
Prices on Longboat have dipped as low as $350,000 for an older two-bedroom, two-bath Gulf-view condo; $3 million buys into newer mid-rise buildings En Provence and La Firenza. St. Armands and Lido keys, separated by a barely noticeable canal, offer a mix of older motels turned timeshares, bungalows, a handful of 1920s homes built during Ringling’s reign, and midcentury Sarasota School of Architecture masterpieces. At Lido’s southern tip, Ritz-Carlton Beach Residences start at $1.5 million. Homes on St. Armands Key rim the circle, a Ringling-created garden with Italian statuary that offers shops and restaurants like Café L’Europe, once the place to be seen, says Betsy Coolidge, whose visit 25 years ago led to her marrying one of its owners.
Bird Key, a man-made island between downtown and St. Armands, has a yacht club and just 510 homes — all single-family, and one-third of them on the bay or wide canals. Home to TV talk show host Jerry Springer, the key has nonwater properties that are half their former $1 million asking price. Many will fall to the raze-and-rebuild trend seen in Miami. Homes on the bay start around $3 million, says Moulton, who resides here.
Siesta Key is an island unto itself, literally and figuratively. “You’re going to get 25 to 30 percent more house on Siesta than Longboat for the same price,” Moulton says. Its northernmost access is a mile or so from the causeway, and its easygoing ambience is embodied by Siesta Key Village, with places like the Siesta Key Oyster Bar and Sunday drum circles on its powdery sands. Beach “experts” of all sorts have proclaimed Siesta Key’s beach one of the best in the country.
Bayfront communities in coveted locations just west of U.S. Highway 41 include “Harbor Acres’ McMansions and Cherokee Park, where a lot of Sarasota’s old money lives,” Moulton says. Both are close to Southside Village, home to tea boutique Spice Girls, Morton’s Gourmet Market and Libby’s Café + Bar. Sarasota’s downtown condos offer views of Sarasota Bay and range from $300,000 (usually in need of a major rehab) to $1 million-plus. “The typical downtown condo buyer is coming from a single-family home on the islands,” Moulton says. These residents can walk to Marina Jack or to the six-block downtown, where they find homegrown boutiques like Belle de Jour and plenty of restaurants, including newcomer Brasserie Belge.
The number of available homes is now at its lowest since 2008. “The overall market is just under six months inventory,” Moulton says, and some neighborhoods could soon experience an uptick in pricing, making Sarasota a good buy now.