If you've driven Tamiami Trail through Osprey any time in the last few weeks, you've probably sat behind a line of cars at Blackburn Point while a boat came through and someone cranked the bridge open by hand. It's been happening since 1926. What's new is what's sitting on the other side of that wait: a 120-seat restaurant that didn't exist here in July, serving brunch at 9 a.m. to a corridor that a lot of outside investors still describe as sleepy.
Two things happened at this same quarter-mile stretch of road this summer, and neither one got much attention outside its own lane of coverage. Put them next to each other and they tell you something about where this pocket of South Sarasota County is actually headed.
What Opened at Blackburn Point Plaza
Five Nine Grill & Tavern soft-opened its Osprey location on August 10, with a grand opening the following Monday, August 17. It's the first time the Bradenton restaurant has expanded anywhere. Owners Mike and Holly DeGirolamo, along with partner Quincy Watkins, took over the former Bay Leaf space at 1092 S. Tamiami Trail in Blackburn Point Plaza and gutted it. The Osprey dining room runs about 3,000 square feet, seats roughly 120, and staffs up to 60, all larger than the 2,400-square-foot original on Cortez Road West.
The menu carries over the Bradenton favorites, scratch-made comfort food with a rotating seasonal list, but the Osprey location leans harder into brunch, served daily starting at 9 a.m. Biscuits and gravy, shrimp and grits, a fried green tomato omelet topped with pimento cheese. Lunch and dinner bring the Giant Tavern Pork Tenderloin Sandwich and the Cortez Cordon Bleu Melt, both $14, a Fresh Grouper Sandwich at $21, and a full bar pouring Casamigos margaritas alongside local craft beer.
DeGirolamo told a reporter earlier this year that he and his partners had their eye on this stretch for a while. "We always liked the area," he said of Osprey, Nokomis, and Venice. That's a modest way to describe committing to a second location, your first ever, in a plaza your customers reach by crossing a bridge that a bridge master has to open by hand.
The Bridge Nobody Expected to Still Be a Live Question
The Blackburn Point Swing Bridge crosses the Intracoastal at Little Sarasota Bay, connecting the Osprey mainland to Casey Key. It's listed on the National Register of Historic Places and is one of the last historic swing bridges still operating in Florida. Sarasota County has been signaling for years that it would rather replace the span than keep maintaining it, citing safety concerns and the lack of room for pedestrians and cyclists.
That plan hit a real obstacle three days ago. On September 13, a new technical review commissioned by the Sarasota Alliance for Historic Preservation and prepared by Bach Ornamental & Structural Steel, a Michigan firm that specializes in historic bridge restoration, put rehabilitation costs at roughly $17 million through 2043, split between an estimated $6 million in 2028 and about $11 million in ongoing maintenance after that. The county's own estimate for a full replacement runs $65 million to $75 million, and that figure doesn't include the cost of widening the approach roads.
That's not a small gap. It's the difference between a project a county can plausibly fund out of routine capital budgets and one that competes with much bigger line items. The review does come with a caveat: Bach Steel hasn't yet completed its on-site inspection, so the number could move once engineers actually get hands on the truss.
The preservation fight has real numbers behind it too. The Alliance says nearly 2,000 residents have contacted the county commission or signed on to save the bridge since it landed on the group's 2025 "Six to Save" list of at-risk historic resources. SAHP co-president Jan Vertefeuille put the stakes plainly: "For many, the bridge is a source of community pride." The county commission is expected to take up the bridge's future later this year, but as of now there's no vote scheduled.
Why These Are the Same Story
Here's the part that's easy to miss if you only read one of these stories and not the other. A restaurant just placed a real bet, new construction, new staff, a menu built around getting people there for breakfast, on a plaza whose only water crossing still runs on a system designed for 1926 traffic volumes. Every time a sailboat needs through, the crank turns, the bridge swings, and cars queue up on both sides. That's not a hypothetical inconvenience. It's the daily operating condition Five Nine's owners chose to build a second location around.
Whichever way the county eventually rules, something changes for that corner. Replace the bridge with something wider and faster, and you get a plaza with fewer traffic pinch points but a mechanism that took a century to earn its spot on the National Register gone for good. Rehabilitate it instead, and Blackburn Point keeps its identity, the hand crank, the swing, the occasional five-minute wait behind a shrimp boat, right as a new business is counting on steady car traffic to make its numbers work. Neither outcome is obviously the growth story or the preservation story. They're both, at the same time, at the same plaza.
What's Worth Watching Between Now and the Vote
There's no hearing date yet, so this isn't a countdown. But a few things are worth keeping an eye on if you're in this part of Osprey regularly. The county commission's eventual decision will likely reference the Bach Steel findings directly, so watch for a formal response from county engineering once the on-site inspection wraps. If the county sticks with its $65 to $75 million replacement estimate despite a competing number that's a fraction of that, the disagreement itself becomes the story worth following.
In the meantime, the corner keeps functioning the way it always has. Blackburn Point Park, just past the bridge, still has its paved kayak launches on both sides of Blackburn Point Road, a boat ramp, a fishing pier, and enough shade to make it a real stop rather than a drive-by. Five Nine is open seven days a week, 9 a.m. to 10 p.m., for anyone who wants to see what a 35-year restaurant veteran does with a bigger kitchen and a brunch menu.
Osprey doesn't get talked about as much as Sarasota or Venice, and that's part of what's made this stretch appealing to people paying attention. A new restaurant betting on it and a preservation group willing to commission its own engineering review to protect a hundred-year-old bridge are both signs of a place people care enough about to invest in, in very different ways, at the exact same address.
If you're watching this corridor for reasons that go beyond dinner plans, whether you already own here or you're weighing what a stretch like Blackburn Point actually offers long term, Susan Phelps has spent more than 40 years getting to know Sarasota and Manatee County corner by corner. Reach out when you're ready to talk specifics, or use Search Homes on her site to see what's currently available nearby.
