When we began our search for Sarasota’s prettiest houses, we had no idea it would lead to such variety. We asked savvy realtors and design professionals—and you, the readers, through our Web site and Facebook page—to nominate their favorites without taking into account cost or age or architectural style—or the way it looked inside. This was strictly about exterior beauty. The result, after weeks of winnowing down the final selection, is a surprising collection of big and small, old and new, humble and grandiose.

What do they all have in common? Very little, except for that indefinable element that makes each one—well, beautiful. And—something we had not expected—almost every one turned out to be a Sarasota archetype.

We estimate they range in value from $300,000 or so all the way up to $20 million. The oldest one dates back almost a hundred years. The newest are products of our recent, dearly departed building boom. Our only rule was that you have to be able to get a good look from the street. Or, this being Sarasota, the water.

These are private homes, don’t forget, and the owners—who in no way helped out with this article—deserve their privacy. But we can look, can’t we?

We posted some runners-up on our Web site. Feel free to add your own nominations. Or comment on what’s posted.

 

3710 Bayou Louise, Siesta Key

This home, dating from the 1960s but remodeled over the years, epitomizes what Sarasota is all about: the water, the sun, the view, the lure of the tropics. The waves lapping on the tiny private beach raise this residence into a class by itself.

 

408 Venezia Parkway, Venice. 

This Venice charmer is so picture-perfect you can spend hours poring over the details. The home is approaching its 90th birthday with all its original style intact. Its descendants are everywhere, but here is proof that you can’t top the original.

 

1300 Westway Drive, Lido Key

Paul Rudolph’s famous Umbrella  House was considered revolutionary when built back in 1954. Some years ago a hurricane destroyed the “umbrella”—a beamed trellis that covered the pool. Plans are underway to restore the umbrella; in the meantime passers-by can admire the subtle simplicity of Rudolph’s mid-century façade.

 

7219 Broughton St. Broughton Street in Whitfield Estates is a treasure trove of Spanish homes dating back to the 1920s. This one was all our judges' favorite. The gnarled oaks complete the beautiful picture—asymmetry against geometry, dappled with sunlight.

156 Beach Road, Sarasota

In a town of fabulous beach houses, our panel chose this 1970s classic near Siesta Village. It’s a house that suggests more than it shows. We can so easily picture the perfect vacation going on inside—the endless afternoons, the breeze from the Gulf, the margaritas, the hot, hot sun.

 

1219 Westway Drive, Lido Key 

Sometimes less isn’t more. Certainly not when it comes to the Spanish Mediterranean mansions that changed the face of Sarasota during the boom. It’s hard to pick our favorite—most of them are mind-numbingly similar—but we had to surrender to the sheer audacity of the wonderfully over-the-top example at right and below.

 

8011 Longbay Blvd.

This Guy Peterson-designed mansion in Whitfield stops traffic every time. It’s enormous, overpowering, even a little shocking. But it’s never vulgar. As  an example of sophisticated taste writ large, there’s nothing else like it in town.

 

44 S. Washington Drive, St. Armands. 

The Sarasota School of Architecture was many things­—simple, elegant, modern. But it was rarely pretty. This home (opposite) is the exception. “A lollipop of a house,” said one of the panelists. Our favorite touch: the mounted sculpture on the façade, which the house wears like a prized piece of jewelry.

 

159 Island Circle, Siesta Key

Maybe you have to be an old-timer to appreciate this cottage. Most of Sarasota used to look like this. Today it’s a nostalgic piece of folk art, a reminder of a simpler time and place. Notice the old-fashioned, farmhouse style landscaping and the playful color choices around the front door.

 

1546 Bay View Drive

Cherokee Park is full of magnificent houses from all eras. There are Spanish, ranch, even moderne. We looked at them all, but we kept coming back to the classic simplicity of this pre-war Colonial Revival. A good example of how the perfect landscaping, honed by time, can make a house sublime.