Sarasota is said to be the city where the modern condominium was invented, back in the early 1960s, by the late developer I.Z. Mann. He kicked off a condo-building boom that’s still going strong. Today, Sarasota has hundreds of condos—and a few apartment buildings from earlier eras—but only a handful stand out from the crowd. Sometimes it’s because of their exclusivity and the price tag that accompanies that. Other times it’s their unique architectural style, either aesthetically superb or wonderfully wacky. Or maybe it’s the social history that has unfolded behind their walls and around their swimming pools. Here’s my list of 10 buildings that define apartment living in Sarasota. If you’re looking for a condo, this is where to start your search. But which one is for you?  

If you aspire to a place in the Old Guard, check out Sarabande. It’s a society page of a building, crammed with old-timers who live in elegant, glass-walled apartments overlooking the bay. Philanthropist Betty Schoenbaum makes her home in the penthouse and travels by elevator to see her friends from boards and committees. Sarabande was built in 1998 and is starting to look a little dated—along with, one might say, its residents (Betty just turned 100)—but when units come on the market (they start at just under a million) they go quickly. 340 S. Palm Ave.

If you’re an artist with a modest nest egg or a millennial dying to live downtown, do something daring. Ignore the Rosemary District and take a look at The Frances Carlton, built in 1924 and probably the oldest apartment building in town. The Frances Carlton has a great look: pastel colors and whimsically arched windows. It’s in the heart of downtown, right next door to Florida Studio Theatre. Most of the units are tiny—700 square feet—and their layouts suggest a railroad tenement of yore. It doesn’t matter, that’s part of their charm. They’ve been all gussied up and are perfect for singles who don’t need much closet space. Prices start around $300,000. 1221 N. Palm Ave.

If you’re a billionaire hedge fund manager who wants a place for three weeks a year, consider Vizcaya. Ever since it was built in 1997, Vizcaya has been regarded as the place to live on Longboat Key. Visually, it’s just a grouping of low-rise Mediterranean buildings surrounded by trees and green space. But inside, house-size units ramble on from room to room, all with beautiful views out to the greenery and the Gulf. The concierge service is said to be the best in town—they’ll stock your refrigerator before you arrive from one of your three or four other homes. The Jenkins family (they own Publix) had a place here. Homes range from $3 million to $5 million. 2355 Gulf of Mexico Drive

If you crave kitschy glamor, don’t miss Le Chateau. It’s a gaudy, guilty pleasure of a building, a great-big pink wedding cake with white piping. Built in 1971, it has the exuberance—part Miami, part French Riviera—lacking in the more timid buildings of its era. Check out the signature curved balconies with their wrought-iron railings. It’s got a great location next to the Ritz-Carlton, Sarasota, with much better views. You can buy in for around half a million. 37 Sunset Drive

If you’re a discreet multimillionaire who’s indifferent to the beach but wants a pied-a-terre in Sarasota, I recommend The Tower Residences at the Ritz-Carlton. This is not the Ritz hotel. To paraphrase Yogi Berra, nobody lives at the Ritz; it’s much too crowded. But they do live in the building next door. Here the hubbub of the hotel has vanished. The lobby is pin-drop quiet and the vast expanses of public space are empty, but in a good way. The atmosphere is elegant and a little bit urban. Best of all, the services—and food—of the Ritz are just a phone call away. $1.5 million to $5 million. 35 Watergate Drive

If you must have a condo on Siesta Key, take a look at The Terrace. Poor Siesta Key, the country’s best beach, and the town’s worst apartment buildings. All those weekly rental vacation complexes took up all the good space and now we’re stuck with them. An exception is The Terrace, a glorious throwback to 1970, when it was built by architect Frank Folsom Smith. (If you detect a resemblance to Plymouth Harbor, the posh retirement community on John Ringling Boulevard, it’s because he designed both.) The Terrace is 17 stories high and its premium location, on the nicest, widest stretch of beach, makes it highly desirable for year-round living. It’s on the edge of Siesta Village but just far enough away so you don’t hear the endless choruses of “Margaritaville” from the bars. Prices start at $600,000 and go up to $2 million. 6400 Ocean Blvd.

If you’re a Sarasota history junkie, the Orange Blossom would be the perfect choice. It was the town’s first real high-rise, built in 1926 as an office building. It then became a hotel, possibly the best in town, and played host to all the visiting celebrities of the day, including Esther Williams, Peter Lawford and the entire cast of the 1952 film The Greatest Show on Earth. Then came a stint as an old-age home. It was rescued and remodeled back in 2000 by the late entrepreneur Jay Foley. Now it has seven large (4,000 square feet) full-floor apartments and a two-story penthouse. Units are highly individualistic and some are quite elaborate and glamorous. It’s at the very epicenter of downtown and residents are entitled to use the amenities—pool, parking—at 1350 Main, right across the street. Expect to pay $1.5 million to $2 million. 1330 Main St.

If you’re a fan of the late mystery writer John D. MacDonald, consider the Siesta Royale. One of the early condo buildings on Siesta Key, it’s become a time warp of Sarasota circa 1960. Everything has remained the same—the zig-zag roof line, the iconic logo splashed across the white concrete block façade. True, the interiors of the apartments mostly one-bedroom, have been updated, but the atmosphere is still the same: fun in the sun, but just under the surface there may be something nefarious going on. The Crescent Club is right across the street. It’s the key’s oldest dive bar and plays a starring role in MacDonald’s novel about a monster hurricane—titled, appropriately enough, Condominium. Units start at around $350,000. Keep in mind, your neighbors will be short-term vacationers. 6334 Midnight Pass Road

If you’d rather be living in Manhattan, head to Cityscape at Courthouse Centre, where the 19 units—all on the top two floors of this mixed-use building—have a chic urban feel. They are designed like lofts, with a two-story living area and a staircase that ascends to an upper level with bedrooms. The building itself is sculpturally modernistic and the location, at the eastern end of Main Street, has great restaurants and the Hollywood 20 movie complex right across the street. Also across the street—the county courthouse, where you might find yourself if you default on the building’s unusually high monthly maintenance fees. Units go for half a million up to $700,000. 1990 Main St.

And finally, if you thrive on the pursuit of all that’s new and glamorous, the big new Vue on Gulfstream may be just the thing. True, it’s controversial—the building people love to hate. But it’s intertwined with the new Westin hotel (actually, they are two separate buildings) and this gives it a crazy energy that the other new condos downtown just don’t have. Some of the apartments are on the small side, with interior dens and a service hall that runs, motel-like, on the outside of the building. And the glamorous modern décor of the public spaces is so on-trend that it already seems a little dated. But from the rooftop bar of the hotel you enjoy the best view in town. You can sip your mojito while looking down at the terrified tourists trying to cross U.S. 41. It’s an instant landmark, a sort of Lido Casino for the 21st century that we will be enjoying for a very long time. Just one question—where’s the damn front door? At press time, two units remained, one for $1.5 million and one for $1.7 million. It’s too soon for resales, but they will probably run from around $1 million and go up to $4 million. 1155 Gulfstream Ave.