Mike DeGirolamo has spent 35 years in the restaurant business, and this spring he picked a spot for his second location. Not Sarasota. Not Nokomis. A stretch of South Tamiami Trail in Osprey, in the plaza that used to hold Bay Leaf, the Indian restaurant that closed out of that space.
When the Business Observer asked why there, DeGirolamo didn't talk about rent or square footage. He talked about the neighborhood itself, saying there was "a lot going on out there in Osprey, Nokomis, Venice, South Sarasota." He also said something worth sitting with if you live here: Osprey is as far south as he and his partners plan to expand. North toward Sun City, maybe. South past Osprey, not really.
That's one data point. On its own it's a nice anecdote about a comfort-food operation moving into a strip mall. Stacked next to what's already happening nearby at a county trailhead and a private nature preserve, it starts to look like something else: three groups with no relationship to each other, betting on the same short run of road within the same year.
The Reasoning Behind The Pin On The Map
Five Nine Grill & Tavern has run out of 5718 Cortez Road W. in Bradenton for more than two years, built around what DeGirolamo calls a "90% scratch kitchen." The menu leans comfort food: burgers, wings, steak, Baja shrimp tacos, a French dip, flatbreads, salads. Daily specials keep regulars coming back, meatloaf on Monday, an 8-ounce sirloin on Thursday, fish and chips on Friday, all priced under $15.
The Osprey location, at 1092 S. Tamiami Trail in Blackburn Point Plaza, is a 3,000-square-foot buildout announced to seat 120. DeGirolamo told the Business Observer the concept would expand into brunch there, on top of lunch and dinner, and that most of the construction work was going into redoing the bar. The group was also working on a liquor license, with an opening the ownership team projected for this past summer.
None of that reads like a company hedging a bet. It reads like an operator who scouted several towns on this stretch of the Gulf Coast and settled on one intersection.
A Trailhead Volunteers Built, Not The County
Osprey Junction Trailhead opened in 2013 as a fairly ordinary county park: fenced parking, picnic tables, bike racks, a water fountain, an information kiosk. What it has become since is less ordinary.
In May 2018, three volunteers who had already been working at the park for years, Chuck Butterfield, Mark Malkasian, and Dave Zimmerman, organized Friends of Osprey Junction Trailhead. Their first real project was converting an old house on the property into a Visitor Center, done through their own volunteer labor and fundraising rather than a county budget line. The county came back around with its own investment too. Park improvements finished in 2023 added a new restroom, paved and unpaved parking, and picnic shelters along the paths.
What actually runs out of that Visitor Center now has a real weekly and monthly rhythm:
- Free pedicab rides along the Legacy Trail, Thursdays at 10 a.m., 11 a.m., and noon, January through April, pedaled by trained county volunteers and funded in part by a $9,500 grant from the Gulf Coast Community Foundation
- A free Florida-Friendly Landscaping demonstration garden tour, led by Sarasota County Master Gardener volunteers, on the fourth Wednesday of every month
Here's the detail that matters if you've been meaning to try the pedicab: the county's own program page currently lists both the 2026 pedicab and surrey seasons as full. A free ride pedaled by a volunteer, on a bike trail, in a county park, sold out its own season. That's not a park limping along on foot traffic. That's a program that outgrew its own capacity.
A Private Preserve That Behaves Like A Public One
A short drive west of the trailhead, off Palmetto Drive, sits Bay Preserve at Osprey, a 4.3-acre waterfront estate on Little Sarasota Bay managed by Big Waters Land Trust. The property centers on the Burrows-Matson House, a 1931 Mediterranean-influenced mansion listed on both the National Register of Historic Places and the Sarasota County Historic Register, named for two families connected to conservation in this part of the county. Elsa Scherer Burrows donated her family's land to create Oscar Scherer State Park. The Matsons later helped establish Bay Preserve itself.
Properties like this usually earn their keep one way: private events. And Bay Preserve does host weddings, with the Great Lawn accommodating tented receptions for up to 285 guests and Michael's On East handling the catering. But the preserve is also open to the public dawn to dusk, seven days a week, free of charge, with public restrooms on site, sitting right next to Historic Spanish Point.
What tells you this isn't just a wedding venue with a public easement is the calendar Big Waters Land Trust runs on top of that. This year alone included the Wild About Nature Festival on March 28, a free family event with food trucks, live music, tree climbing, and kayaking. It drew enough of a crowd that parking had to be routed offsite, to First Baptist Church of Osprey, Victory Baptist Church, the historic Osprey Library, and Evie's on the Bay, with a trolley looping guests back in. A property's own lot running out of room for a free event is the same signal as a volunteer bike ride selling out its season.
Smaller, recurring gatherings fill in the rest of the year. Sunset and S'mores evenings ask for a $5 donation and let visitors cast a line off the dock, roast marshmallows over a campfire, and bring lawn games for the Great Lawn. The Summer Trivia Showdown returned this year on August 19, free to enter with teams of up to eight, food available for purchase from Killik's Kitchen, and a prize of a private guided hike or kayak outing for the winning table.
Same Six Blocks, Three Unrelated Bets
Here's the part that doesn't show up if you only look at one of these on its own. A restaurant group headquartered in Bradenton studied this corridor and picked Osprey as the southern edge of its expansion. A volunteer nonprofit spent eight years turning a county trailhead into a program popular enough to book out a full season. A land trust running a historic estate built a public events calendar substantial enough to overflow its own parking lot.
None of these three coordinated with each other. A restaurant owner chasing brunch traffic has no reason to track a land trust's trivia night, and a Master Gardener leading a Wednesday garden tour isn't thinking about liquor license applications down the road on Tamiami Trail. But all three read the same area the same way, in the same rough window of time, and all three decided it was worth building something that outlasts a single season.
| Who | What they built or run | When it took shape |
|---|---|---|
| Friends of Osprey Junction Trailhead | Visitor Center, Thursday pedicab rides, monthly garden tours | Founded 2018, park upgraded 2023 |
| Big Waters Land Trust | Free festivals, campfire nights, trivia events at Bay Preserve | Ongoing, expanding through 2026 |
| Five Nine Grill & Tavern | Second location in Blackburn Point Plaza | Announced spring 2026 |
For anyone who already calls Osprey home, that convergence is worth knowing even if you never set foot in a real estate listing. It means the next time you're deciding where to grab a Thursday pedicab, watch for a s'mores night on the bay, or try a new brunch spot, you're not chasing three unrelated errands. You're circling the same handful of blocks that a restaurant owner, a land trust, and a group of county volunteers all decided, independently, was worth the investment.
If you ever do find yourself thinking about what a home in this stretch of Osprey might be worth, or wondering what else is quietly shifting along this part of the coast, that's a conversation we're glad to have. What's your property worth? Call The Real Estate Captains for a free market valuation.
