Walk This Way

Southside Village Is the Perfect Sarasota Neighborhood

Homes from various decades exist side by side, and practically all have been spruced up and beautifully landscaped.

By Robert Plunket March 5, 2020 Published in the March 2020 issue of Sarasota Magazine

Eclectic homes surround Southside Village.

Image: Jenny Acheson

Everybody wants to live in Southside Village. It is, arguably, the perfect Sarasota neighborhood. Realtor Barbara May, who has lived there for years, tells how, when she has new clients who think they want Longboat or Siesta, she accidentally-on-purpose drives them through Southside Village and they all go, “Wow. What is this place?”

“This place” is a classic American suburb of 50 or 60 years ago. Homes from various decades exist side by side, and practically all have been spruced up and beautifully landscaped. Mature trees shade the streets. There is no doubt that much of its charm is due to the nostalgia factor; many Sarasotans grew up in places like this.

Among Southside Village’s many charms are its historic homes.

Image: Jenny Acheson

Doctors and lawyers lived here back then, but more typical residents were the town’s middle class—the teachers, nurses, cops and plumbers. Circus folk called it home, too; check out the Wallenda compound on Arlington Street, complete with historic marker.

Southside Village has no set boundaries, and everybody describes it a little differently, particularly realtors with a house to sell. From a walkability point of view, let’s say its northern boundary is Bahia Vista and its southern boundary is down around Bougainvillea. The eastern boundary is the Trail; the western is Orange Avenue.  It borders impressive neighborhoods like Harbor Acres and McClellan Park, and parts of them are included in the Southside Village walkability zone.

Eclectic homes surround Southside Village

Image: Jenny Acheson

Much of the walking is being done in three directions. First, to the commercial center, which includes Sarasota Memorial Hospital, an enormous institution that discreetly blends into the neighborhood. And although I can’t seem to conjure up the mental image of a doctor walking to work, they certainly could, and many do live here.

The second place everybody walks to is school. In fact, the whole neighborhood seems to be named after its elementary school, Southside. It’s considered one of the area’s top public schools, and has educated generations of Sarasotans, including Pee-wee Herman, who would walk from his home on nearby Sparrow Court. Kids still walk to school, but these days they are mostly accompanied by their mothers (and sometimes fathers). So many walk, in fact, that locals have learned to avoid the area when school lets out.

Southside Elementary School

Image: Jenny Acheson


Popular Morton’s Gourmet Market

Image: Jenny Acheson 

And, of course, there’s Morton’s Market. This gourmet grocery store has such a strong personality that it’s set the tone for the entire neighborhood. Both offer an old-fashioned WASP-y style, livened up with a dash of Real Housewives glitz.

Southside Village is changing rapidly, and not everyone likes what’s happening. Many of the charming old houses and mature trees are being torn down and replaced with new construction. Some are builders’ models; some are architecturally distinguished modern homes. They blend in surprisingly well. It’s only made the neighborhood more popular, though—you get a brand-new million-dollar home, great restaurants and shopping, and if worse comes to worst, you can walk to the emergency room.

Worth Walking To

Veronica Fish & Oyster

Hip, stylish restaurant, seafood mostly, outdoor seating. 1830 S. Osprey Ave.

Seminole Linear Park

Grassy space with benches and walkway. Pets on leashes allowed. 2100 Mietaw Drive

Five O’Clock Club

Old-time hangout, live music and a full bar. 1930 Hillview St.

Real Estate Sampler

High: 1807 Oleander St.

7 bedrooms, 7.5 baths, 9,492 square feet. French chateau-style, walled mansion built in 2006. $4,499,000.

Low: 1937 Boyce St.

3 bedrooms, 2 baths, 1468 square feet. Built in 1947, set on quarter-acre lot. $495,000.

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