The Next Hot Sarasota Neighborhoods

Bob Plunket highlights five up-and-coming Sarasota neighborhoods.

By Robert Plunket Photography by Jenny Acheson April 1, 2012

Just as Manhattanites started moving to Brooklyn and turned it into the hip new place to live, Sarasotans are looking around at neighborhoods that used to be a little declassé, a little square, a little shabby, and thinking, “Hey, I could live there.”

And not only are these neighborhoods getting a second wind; they’re beginning to attract some of the most interesting people in town. They’re developing their own shops and restaurants. And best of all, while they may not have social cachet—yet—they have the greatest luxury of all: location. They got there first. All the attractions that make Sarasota such a great place to live are right around the corner—or a short sprint down Tuttle.

Even the dated look that some of them have is turning to their advantage. Craftsman bungalows have been hot for years. Now Mid-Century Modern is the latest style, and your grandmother’s ranch house circa 1959 is suddenly chic. What’s next may well be the ’70s look—vaulted ceilings, sliding glass doors and what might be the greatest innovation of all: the walk-in closet.

Let’s look at five of these neighborhoods. These are the ones on the cusp of becoming cool. Places like Southside Village and the Ringling Museum area don’t count. They’ve already been discovered. These are the next ones set to take off.

Clockwise from far left: walking through Gillespie Park, the famous  lighthouse, morning coffee at Savory Street, flowers at Citrus Square.NEXT HOT ’HOOD

Gillespie Park

Let’s start with Gillespie Park. Yes, I know it’s been on the verge of taking off for years. Then something always happens and things fizzle out. It’s the neighborhood that cried wolf. Now that it’s finally becoming the hip bohemian enclave it was destined to become, nobody seems to believe that it’s happening.

Why this time? The reason is simple. Downtown has exploded. Aside from the arts scene, new shops and restaurants have sprung up everywhere. And Gillespie Park is right across the street.

A half-mile square area of old cottages and concrete duplexes, Gillespie Park does has to deal with a somewhat shady reputation. Low-income renters are still drawn to the area, and guys fixing cars parked in the front yard are a common sight. But every month, more of the houses are going from shabby to chic. One block—Seventh Street between Orange and Goodrich—has already become semi-famous for its brightly colored 1920s cottages.

Artists and actors have always called the Gillespie area home, but the newcomers are bringing a critical mass of respectability. Patricia Vandenberg, an administrator at Mount Holyoke College, and her husband, Julian Olf, a playwright, epitomize the trend. “Gillespie Park has a sense of becoming,” Patricia says. “It’s not staid. It’s exciting.”

Patricia and Julian stumbled upon the place when his daughter moved there. At first, they were put off by the notion of Florida, but a visit changed their minds. “Our stereotype of boring blue-haired folks on golf carts was blown away by Sarasota,” confesses Patricia. “The vibrant arts culture, the glorious beaches, the great downtown and plenty of people of all ages—it’s the gem of the state, and Gillespie Park’s downtown location at affordable prices makes it unique.”

The touch of Key West in the atmosphere is now being complemented by a more refined style. Check out Citrus Square at North Orange and Fruitville. It’s the most elegant apartment building in Sarasota, with two wonderful restaurants on the ground floor. And what neighborhood can go wrong when your corner market is Whole Foods?


Location: bordered by Fruitville Road on the south, Orange Avenue on the west, 10th Street on the north, and U.S. 301 on the east.

The housing situation: The old bungalows go quick, renovated or not. There’s a nice one at 1936 Eighth St. that’s priced at $149,000.

Local landmark: the famous boat and lighthouse at Fifth and Osprey—soon to become a bed-and-breakfast.

Eat at: Savory Street and Pomona on Orange; The Breakfast House and Canta Rana on Fruitville.

Interior designer Holly Dennis’ 1950s retro ranch house—and cars.NEXT HOT ’HOOD

Paver/Ringling Park

Paver/Ringling Park: These two neighborhoods border downtown on the east. Ringling Park has small custom homes from the 1950s; Paver Park has ranch homes from the same era, but all built at the same time, using two or three different floor plans.

For years nobody paid either of these neighborhoods the slightest bit of attention, but their incredible location finally won out. You can walk to downtown, drive anywhere in minutes—the Y, the beach, the ballpark. And the homes are cute. If they’re not, hire one of the hip designers who live in the neighborhood and they’ll make them cute.

Like Mark Dalton. Back in 2007 he took a look at a ranch house from 1957 on a Friday, and by Monday he was the owner. It had all sorts of things that you just can’t find anymore—cedar closets, plaster walls, bedrooms with corner windows, and a live oak that takes up one-quarter of the 10,000-square-foot lot. After some low-budget fixing up, it’s now the showplace for Mark’s business, Chic on the Cheap. He specializes in remodeling older, solidly built homes with good bones on a shoestring budget.

“People have finally discovered what a great neighborhood this is,” Mark says. And though the homes are on the smallish side for today’s families, they’re perfect for the young professionals who are moving here. “When I moved in, I had the nicest car in the neighborhood,” says Mark. “Now everybody has nice cars.”

And speaking of cars, check out the collection that Holly Dennis, also an interior designer, has parked in her driveway. Holly’s 1950s retro ranch was the hit of this year’s Designer Digs Showcase put on by the ASID.


Clockwise from top: skateboarding at Payne Park, Mark Dalton’s redone Ringling Park house, out for a spin, raking up oak leaves, inside the Shamrock Pub.Location: bordered on the west by Lime Avenue, on the north by Fruitville Road, on the east by Tuttle Avenue and on the south by Wood Street.

The housing situation: older ranch-style homes that average around 1,100 feet. The good ones go

immediately, but when they’re on the market, they start in the low $100,000s. There’s a beautifully remodeled house on Pelican Drive for $214,000—high for the neighborhood.

Local landmark: The Sarasota High building, with its Paul Rudolph architecture; the original 1920s Collegiate Gothic structure next to it will soon be a modern art museum.

Best hangout: the old Shamrock Pub on Ringling has become a favorite with the young arty set. Film star Elijah Wood dropped by after he spoke at Ringling College. Payne Park is great for tennis, dog-walking and skateboarding.


Pastries at Ooh La La, inside Hurricane Mike’s in Gulf Gate VillageNEXT HOT ’HOOD

Gulf Gate

The quintessential neighborhood of Florida retirement circa 1975 is about to undergo a big change. With the original residents going to a better place, they’re being replaced by young families, young professionals and younger retirees. But what’s giving Gulf Gate “street cred” for an acceptable place to live is the unlikely success of Gulf Gate Village.

The village used to be famous for its motley assortment of pathetic-looking stores—seriously bad consignment shops and low-rent tanning salons. I seem to remember the Moose Club was there. The streets were always full of potholes. It was tacky and unworthy of the name “Gulf Gate” or “Sarasota.”

Now it’s the hippest place in town. Those lowdown bars are now the heart and soul of Sarasota’s music scene. It’s by far the biggest and best bar scene in town. Who doesn’t love an evening at Mr. Beery’s—currently the “it” bar—or perhaps the Angry Pickle.

But wait—there’s more.

It’s also become a food destination. Many of the latest must-try restaurants are there, from Veg to Piatti. And it’s somehow become the place to go for gourmet oddities, European groceries, great sushi, cupcakes and a snack-bar dive that has become world-famous for its over-the-top junk food.

Brooklyn didn’t take off until it got better restaurants and bars. That’s what makes the difference when it comes to attracting new residents. So this, coupled with the easy bike ride to Siesta Key, means that Gulf Gate is suddenly becoming very attractive.

It’s taken me years to come to terms with the average Gulf Gate home, as it practically has “Genteel Retirement” stamped all over it. These are modest homes, and they are very similar to each other. They have no grandeur, no individuality, or so I used to think. Now I see them as architectural classics. They’re the Craftsman bungalows of tomorrow.

You can get one very inexpensively right now. Bad examples can be had for around $100,000, and an average home in Gulf Gate proper, updated, will be around $150,000. Gulf Gate East and Gulf Gate Woods are adjacent but farther east. The homes here are newer and more expensive, but the general feeling is the same. Still, when you’re that far east, you can’t walk to the Angry Pickle. You’d be defeating your whole reason for moving there.


dining at Il Panificio, Gulf Gate ranch, stores in Gulf Gate Village, classic Florida living.Location: Bordered on the west by U.S. 41, on the east by Beneva Road, on the north by Clark Road and on the south (roughly) by Cass Street.

Any condos? A few around the edges, again to the east. There are also rental apartments off Gateway Avenue, just a block from the action.

Local landmark: The striking, modern St. Thomas More Church and the Chelsea Center, designed by Carl Abbott, one of his signature buildings.

Eat at: Vizen, Mamma Mia, Piccolo’s, Piatti, Il Panificio, Word of Mouth—and that’s just the beginning.

Don’t miss: Ooh La La, a new French bakery (try the chocolate-almond croissants), Nancy Dunn’s Estate Sale Outlet, with an eclectic mix of art, antiques and jewelry.



Clockwise from top: Looking across Sarasota Bay from a Pine Shores dock, pretty lawns and tall pines everywhere, boats are common in driveways.NEXT HOT ’HOOD

Pine Shores

This almost unknown neighborhood has the distinction of being the only mainland community that’s an easy walk to Siesta Key. It’s right over the South Bridge, in fact. You cross the bridge and Midnight Pass Road, head down the beach access path and there you are, on the country’s best beach. It took you less time than most people who live on Siesta Key to get to the beach. And it’s all from the low $100s.

Of all the waterfront communities west of the Trail, Pines Shores is both the sleepiest and the cheapest. It has a drowsy 1950s suburban air, with low-slung houses on large plots of land. They are ranch houses, but compared to their neighbors in Gulf Gate, they’re a little blowsy and eccentric.

There are three parts of Pine Shores: the newer, expensive homes on the water, the tightly manicured one-story condos, and the older homes nearer the Trail. The newer expensive homes need not concern us, nor do the condos, nice as they are. It’s the older homes that give Pine Shores its old Sarasota feeling.

A row of 1950s Florida ranches; below, The Oaks draws barbecue lovers from all over town.Amenities are few. In fact, I can’t think of any. But once you leave the time capsule there’s all sorts of stuff. On the other side of Stickney Point Road the old health food store and Carrabba’s Restaurant have been joined by some new shops and another good chain restaurant. Gulf Gate Village is less than a mile—if you survive getting through the busiest intersection in Sarasota. Across the bridge is a whole cluster of shops and eateries, including the famous Crescent Club, a gourmet grocery store, karaoke at Captain Curt’s and some very nice restaurants.

Location: bordered by U.S. 41 on the east, Sarasota Bay on the west, Stickney Point Road on the south and Phillippi Estate Park on the north.

Landmark: The Oaks Open Pit BBQ, on the eastern edge, is a longtime local favorite. And The Boatyard shopping and dining area, right on the Intracoastal, could develop into a great destination for both locals and tourists.


A Panamanian student at IMG, bayfront walkway at Wild Oak Bay.NEXT HOT ’HOOD

IMG / El Conquistador

The IMG/El Conquistador neighborhood is not hip and probably never will be. It’s a classic Florida golf and tennis community, geared toward well-to-do retirement. But its association with the glamorous sports training and management company IMG gives it a definite cool factor. And its upscale atmosphere and convenient location make it an unbeatable value.

Located in southern Manatee County, it is a mere 12 minutes from the Van Wezel Performing Arts Hall. Originally El Conquistador Country Club, it was developed in the mid-1970s. In 1978, tennis coach Nick Bollettieri founded a tennis academy nearby and began training a long list of tennis champs—including Andre Agassi and Maria Sharapova. IMG acquired Bollettieri’s academy in 1988, and expanded it to include golf, baseball and others sports. In 2005, IMG built a campus, which includes condos and villas, and renovated the golf course. IMG is now regarded as one of the top sports training centers in the world.

The athletic prodigies (whose parents often buy second homes here) and retirees co-exist in harmony, both benefiting from a wide range of facilities. Drive down El Conquistador Parkway and you’ll see the always busy practice range, putting green, etc. And there’s a lot of socializing at the IMG country club.

IMG/El Con has various neighborhoods, mostly with large custom homes. But the real bargain here are the condo developments that date back to the 1970s.

Wild Oak Bay is the best, a large but low-key community of almost 1,000 units. The setting is right on Sarasota Bay, and the view from the waterfront units is one of the best around—over an unspoiled shoreline out to Longboat Key, miles off in the distance. It’s a great spot for bird watching.

The less elaborate units at Wild Oak Bay are nice, too. They all have patios and gardens and nature views, and the landscaping is extraordinary—manicured yet tropical, heavy on the hibiscus and flowering trees. You can find single-story, villa-style, two-bedroom apartments in the low $100s.

Even less expensive are the other condo communities, like Valencia. The apartments are almost as nice, and many have golf course views. These days some are selling for under $100,000.

Clockwise from top: garden views at Wild Oak Bay, look out for golf carts, hitting on the practice range.The immediate neighborhood is nothing special, but shopping (including Target and Publix) is a couple of minutes away. Add another 10 minutes or so and you’re in downtown Sarasota. If you want golf and tennis in an upscale atmosphere that looks more expensive than it actually is, IMG/El Con may be just the thing.

Location: bordered on the east by 34th Street West, on the north by 53rd Avenue West and on the south and west by Sarasota Bay.

The look: Each community has a different style. Most common are the simple, geometric 1970 condos; newest are the elaborate Spanish rococo mansions in Legends Bay. (Golf legend Paula Creamer built a house there.)

Who lives there: an eclectic mix of retirees, old Bradenton, international athletes and their families.

Robert Plunket writes our “Real Estate Junkie” column and weekly blog; he recently reported on Florida luxury real estate for Barron’s magazine.

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