Island Living     

The dream usually begins with a novel, a movie, a vacation—maybe even your honeymoon. You want to capture the magic, the romance, that carefree island vibe, not just for a week or a month but for the rest of your life. Unfortunately, the island lifestyles of Hemingway, Gauguin and Brando are not sustainable for ordinary mortals who need good schools for the kids, Wi-Fi, theater, art—and restaurants. Civilization: You can’t live with it, but try living on a far-off island without it. In a really short time the fantasy morphs from bartering beads to couture shopping.

That’s where Sarasota comes in. Eight of Florida’s beautiful barrier islands—we call them “keys”—are between five and 45 minutes away from the heart of downtown. All have gorgeous beaches, tropical foliage, breathtaking sunsets and the most precious of attributes: waterfront property with some of the most spectacular views on the planet.

For Americans, there are no visas to contend with. No shipping in foods you crave from back home. You won’t be cut off from family and friends, because they can afford to visit—and they have a choice of flying into three international airports, none of them more than an hour from your door.

Residents from Anna Maria Island (just north of Longboat Key) to Manasota Key (bordering Sarasota and Charlotte counties) have staked out their slices of paradise based on lifestyle wants and needs. And that’s a good thing, because each island in the Sarasota region has its own personality and ambiance (laid-back, remote, exclusive, private, lively—even sophisticated). To find the perfect match for his clients, Alan Galletto, broker-associate with Island Real Estate on Anna Maria, devotes at least an hour to a thorough overview and comparison. “All of these islands—Longboat Key, Siesta Key—have different feels to them, and you have to find your feel,” he says. “In an island home, the most important thing people look for is a place they’d be comfortable with. Once they can actually feel themselves living there, then they can start looking for a specific home.”

That’s critical on any island, but especially so for Anna Maria. A seven-mile sliver of Florida’s barefoot past, the island has three cities: Bradenton Beach, Holmes Beach and Anna Maria, all surrounded by the waters of the Gulf of Mexico, Sarasota Bay, Anna Maria Sound or Tampa Bay. “Most buyers of property on Anna Maria stumble onto the island—literally,” Galletto says. “They like the feel of it and then they buy.”

At the southernmost tip of our demographic area, Manasota Key is more remote and secluded than other Sarasota barrier islands. “Ours is a very private island,” Nelda Thompson of Nelda Thompson & Associates explains. “If a client comes here and asks where the shopping is, I tell them I’m not sure they would be happy here.”

Indeed, Manasota Key attracts high-profile people who pay a premium for their solitude. “Our residents are very private people: celebrities or heads of companies who love being able to walk on the beach with anonymity here,” Thompson says. Regardless of which island they’ll eventually choose, Thompson says buyers who home in on the Gulf Coast all have one common motivator. “It’s the dream of a beautiful view of the sunset, the bay, the Gulf—water is everything to them,” she explains. 

Most prospective buyers have a pretty good handle on Siesta Key’s renowned white sand beaches and Longboat’s manicured grounds and resort-style amenities. But Deborah Beacham of Michael Saunders & Company likes to introduce prospective clients to residential islands like Casey Key that are less known (or accessible) to tourists.

“I’ve lived on Casey Key for 16 years, and it’s more of a residential community than the other islands,” Beacham says. “There are fewer than 400 single-family homes—no high-rise condos—and it’s ideal for people who really like to relax. It’s all about the beach, fishing—and boating is big because we’re right on

the Intracoastal.”

As you drive to the northern tip of Casey Key, the island becomes narrow enough that you can see the Gulf on one side of the road and Blackburn Bay on the other. “We have an eight-mile island with no traffic lights. It’s a laid-back lifestyle, with lots of mega-mansions, but we still have a number of cottages and Old Florida homes,” Beacham says.

Still, some clients find Casey Key a bit remote for their tastes, and prefer Longboat, Bird, Lido and Siesta keys because they’re closer to Sarasota’s cultural activities, restaurants and shopping. Brokers will point out that condo living is quite different from island to island. Nothing more than two stories high can be built on Anna Maria. Longboat has the bulk of the region’s luxury beach-front high-rises, and Siesta Key has a mixture of both.  

Once you find your island comfort zone, it’s time to snap back to reality with a discussion of price. Alan Galletto says half of the clients who think they want a certain kind of property or location change their minds when he’s finished educating them. “They don’t know all the ramifications, so it’s important to educate about the areas, the values and the pros and cons of different kinds of property,” he explains.

“Out here, three-quarters of what you are buying is land value [whether you are on the Gulf or the middle of the island], and one-quarter is the improvement—the home itself,” Galletto says. “That’s the opposite of mainland property, where one-quarter of the value is in the land and three-quarters in the house. People don’t necessarily know that, and it really impacts their final decision.”

Knowing land values helps prospective buyers determine the size and location of their island paradise. On Anna Maria, for example, 50 feet of direct Gulf frontage is worth about $2 million; 100 feet is $2.5 million. Galletto rattles off the numbers: “A bayfront lot looking directly at the Sunshine Skyway is around $900,000. A lot at the end of a canal where you have 180 degrees into the open water [the bay or Intracoastal] is $700,000. A canal lot is $400,000 to $450,000, because you’re looking across at another house. Finally, a lot in the middle of the island on Anna Maria is $200,000 to $250,000.”

Though prices increase somewhat as you drive south from Anna Maria to Longboat Key, Siesta and beyond, deals on similar properties across the region are common right now. “Prices have dropped tremendously on Manasota Key; properties that were formerly $3 million, $3.5 million or $4 million are now priced below $2 million,” says Nelda Thompson.

Deborah Beacham reports similar reductions. “All land values have come down in the county this year— about 30 percent since the boom of 2006. People who have to sell are making deals happen,” she says. She notes that on Casey Key a home listed for $6.89 million sold in September for $5,127,000—including a trade of a Siesta Key condo valued at $1.3 million. “Trades are becoming more prevalent. People are getting creative in this economy,” Beacham concludes.

What Your Money Can Buy

$399,000 Anna Maria Cottage

Alan Galletto, broker-associate with Island Real Estate, says this adorable Old Florida beach cottage in nostalgic Key West design is just 350 feet from the beach. Located in Holmes Beach on Anna Maria Island, the condo/town home has two bedrooms, two baths, and comes with large private courtyard. Contact: (941) 778-8611

$2,375,000 Manasota Key Showcase

Simple elegance defines this dramatic home, designed by the owners and Jerry Van Deelen of New York and Palm Springs. Listed by JoAnn Schlip of Nelda Thompson and Associates and set directly on Lemon Bay, the home has spacious interiors with 1,000-foot master suite and lush private gardens and pool area. Contact: (941) 475-8572

$6,295,000 Casey Key Estate

Listed by Deborah Beacham of Michael Saunders & Company, this beachfront estate designed by renowned local architect Guy Peterson is called “Oasis by the Sea.” Completed in 2008 by master builder Michael Walker, the 7,722-square-foot home has four bedrooms, 4.5 baths and every amenity, including floor-to-ceiling glass for unobstructed, panoramic views of the Gulf. Contact: (941) 376-2688