Sarasota’s streets are much more than places to live. They are a refuge and a welcome, a living archive of the town’s history, a setting for our lives. And many times that setting is a thing of extraordinary beauty. Here, a few of the ones we love the most. 

Artfully scattered mid-century modern homes peek out from green tropical landscaping on Siesta Key’s Sandy Hook Road

It winds through a neighborhood where old money meets a bohemian attitude—a tangible link to the key’s earlier incarnation as an artists’ colony where talent and creativity ruled the social scene. Shell roads, perfect for dog walking or an afternoon stroll, preserve the Old Florida feeling. Many of the architecturally significant houses boast spectacular views of the Gulf, and new construction—for the most part—blends in discreetly. Siesta Village is a short walk, and downtown is 10 minutes away.

Old Spanish architecture from the Ringling era and a canopy of perfectly gnarled oaks have earned the corner of Broughton and Holly in Whitfield a place on the National Register of Historic Places. The late afternoon sun, reflected off the bay but filtered through the century-old trees, gives this place a special glow. This was one of Sarasota’s first upscale residential neighborhoods, and though it’s had its ups and downs over the past 80 years, it remains one of the prettiest spots in town.

Gulfstream Avenue, with its prime bayfront location, has always been the most iconic Sarasota street of all. Home of the original settlers, today it’s a sophisticated curve of gracefully aging condos and avant-garde art. We usually see it whizzing by at 40 miles an hour. But it takes on a different aspect when viewed from the water. The bay calms the city down and offers a buffer of peace and beauty—not to mention, for the lucky residents, the loveliest views in Florida. Here you’ll find bobbing sailboats, luxury yachts and sunsets that linger into the evening.

Yes, we’re a little bit country, too. Our authentic cowboy heritage starts just east of Cattlemen Road and extends far out into the pastures and tomato fields of Old Miakka. Today it’s threatened with development, as housing and retail move further and further east. But much still remains: family farms, rodeos, feed stores, gentlemen ranchers. Above, the rural mailboxes and unpaved lanes of old Florida never fail to refresh the senses.

Tucked away in the tiny streets and alleys in Laurel Park just east of downtown are scenes that would look at home in Key West. One of the most scenic: Hawkins Court

For half a century this is where Sarasota lived: the early mayors and judges, the middle-class merchants, the school teachers and the nurses. After a rough period when the population moved south, Laurel Park (along with Washington Park and Towles Court) is now officially back. New million-dollar townhouses sit next to Craftsman cottages that could use a coat of paint. Old, new, rich, poor, this is one of the most historic neighborhoods in town—and now the hippest.

With fabulous mansions on one side and a pristine beach on the other, Casey Key Road snakes down a barrier island where the ultra rich of five continents come to hide away in secluded luxury and total anonymity. It seems like there is a little mystery surrounding each house. Is that where the German billionaire lives? The heir to the publishing fortune? The Mafia don? Resident Stephen King has called it one of the four most beautiful places in the world. You can see why.