Drive south on Tamiami Trail past Bee Ridge and you'll pass a building that looks like it's dying. The Macy's box has sat empty since March 2025, one more shuttered anchor in a chain of 66 closures that year. The Dillard's pad next to it has been dark even longer. If you didn't know better, you'd assume the whole property, technically called The Crossings at Siesta Key now, was just waiting for a wrecking ball.
You'd be half right. But the more interesting thing happening inside that building right now isn't decline. It's a theater district.
South Gate the neighborhood and the shopping center at its front door were born within about two years of each other. Developers Rolland King and Frank Smith broke ground on the first South Gate homes in 1955, on land that had been Bertha Palmer's orange groves. The South Gate Community Center, the mid-century hall on Phillippi Creek designed by Sarasota School architect Victor Lundy, was dedicated on September 2, 1956. The shopping plaza across Tamiami Trail opened four months later, on January 15, 1957, as an open-air strip called South Gate Shopping Plaza. Roughly seven decades later, those two structures are aging on completely different timelines, and understanding why tells you more about where South Gate is headed than any listing description will.
What's Actually Still Open Behind the Vacant Anchors
Walk past the empty department store pads and you'll find, tucked into former restaurant and retail space, no fewer than three community theater companies operating within a few footsteps of each other. Rise Above Performing Arts, a youth-oriented company, just moved into a bigger space inside the mall, up to 193 seats from its previous 160. Katherine Michelle Tanner's Tree Fort Productions runs its classes, cabarets, and plays a short walk away. And the 97-year-old Sarasota Players, the city's oldest community theater, is still performing there too, though it's slated to move to a permanent home in Payne Park in the coming season.
Add CMX CineBistro and Connors Steak & Seafood, the two tenants that representatives for the property's ownership group told the city's Planning Board in 2024 were performing well even as the rest of the tenant mix struggled, and LA Fitness in a former Dillard's wing, and you have a building that reads as abandoned from the parking lot and functions as a small performing arts campus from the inside. It's an odd kind of tenant mix to end up with by accident, department stores and gyms giving way to stages and box offices, but that's what seven decades of lease turnover has produced.
The Corporate Clock: Ten to Fifteen Years, Building by Building
None of this is permanent. Benderson Development, which bought the roughly 35-acre property in 2022, has a Sarasota City Commission-approved Comprehensive Plan amendment that clears the way for up to 848 apartments, a mix of retail, office space, and a boutique hotel component, with 10 percent of the housing built as attainable units under a phased proffer, 20 units among the first 400 built, 50 among the first 450, 85 among the first 750.
What's worth noting for anyone living nearby is how slowly this is supposed to unfold. Benderson's director of development told the Planning Board the redevelopment requires demolishing the existing mall building and building stormwater mitigation infrastructure that doesn't currently exist on the site, and that the early phases have to cover those costs before later phases can proceed. Estimates for how long the full build-out will take have moved around depending on who you ask and when. At a 2023 community workshop, Benderson's team floated a timeline of two decades or more. A 2026 reassessment put it closer to 10 to 15 years. Either way, this isn't a project where a resident wakes up one year to a finished town center. It's block by block, lease by lease, with the theater companies likely to keep operating in whatever space remains available until their particular building comes up in the rotation.
The Volunteer Clock, Three Blocks East
Contrast that corporate, phased, multi-decade approach with what's happening at the South Gate Community Center itself, a few streets into the neighborhood proper. The historic Lundy-designed hall and its pool, described by the Community Association as the oldest continuously operated public pool in the Sarasota area, run on a completely different model: an all-volunteer nonprofit funded by optional annual memberships and event rentals.
That funding structure has real limits. The Association has publicly acknowledged ongoing maintenance costs it struggles to cover continuously, and at one point explored the possibility of the county acquiring the historic hall. But the calendar for 2026 shows an organization still very much running its own show. The pool reopened for the season on March 28. A joint garage sale with the neighboring Forest Lakes community drew sign-ups for an interactive map in March. A volunteer cleanup day, described on the Association's own channels as push the leaves, pull the weeds, pizza party, ran the same month. A splash pool party followed on May 1. None of that looks like an organization mid-liquidation. It looks like a group stretching a 1956 building and a 1956-era funding model about as far as either can go, one membership renewal at a time.
The Creek That Runs Under Both
Here's the connection that doesn't show up if you only look at one property or the other. Both the mall's redevelopment and the neighborhood's community center sit on or near Phillippi Creek, and both have been forced to reckon with the same 2024 storm season, when Debby, Helene, and Milton pushed creek levels near the Bahia Vista bridge to some of their highest points in decades.
On the private side, Benderson's own phase-one plan for the mall property includes building stormwater infrastructure from scratch, since none currently exists there. On the public side, Sarasota County secured a federal permit in October 2025 to dredge Phillippi Creek, and the creek is being actively dredged this year to reduce flood risk during storms, a project the South Gate Community Association's Civic Affairs Committee had been pushing county commissioners on directly, partly through a Stormwater Decision Makers panel the Association hosted at its own community center. These are two unrelated engineering projects, one driven by a developer's permitting requirements and one by county disaster recovery funding, happening on the same waterway in the same window of years. Neither one exists because of the other, but a resident watching construction equipment near the creek this year is probably watching both.
What This Means for a Tuesday in South Gate Right Now
None of the long-term uncertainty at the mall changes what's actually available to do in the neighborhood this week. The pool is open for the season. There's a show running somewhere inside the Crossings, whether that's Rise Above's youth program, Tree Fort's next cabaret, or one of the Sarasota Players' final productions before its Payne Park move. Connors and CineBistro are both still open on the same footprint they've occupied for years. And the Community Association's volunteer calendar, cleanup days, pool parties, the annual garage sale, keeps running regardless of what happens to the shopping center across the street.
The honest read on South Gate right now is that it's a neighborhood where two structures built within about two years of each other in the mid-1950s are aging on completely different clocks. One is being demolished and rebuilt by a developer on a ten-to-fifteen-year corporate schedule. The other is being kept alive by neighbors who show up with rakes and pizza. Both are still standing today, and for anyone who lives here, that's the version of the story worth knowing, not the flattened one where the mall is simply dying.
If you're weighing what any of this means for a home in South Gate specifically, whether you're watching the redevelopment from a few blocks away or thinking about buying into the neighborhood while it's mid-transition, Tyler Hahne can walk you through what's actually happening on the ground, block by block, the same way he tracks it for clients across Sarasota and Manatee counties.
