Walk down San Marco Boulevard this month and you will pass three storefronts mid-transformation. One has scaffolding up and a permit taped to the glass. One has a new sign where a French bistro sign hung for a quarter century. One looks almost exactly like it did in 1938, on purpose. If you have lived here a while, you have probably noticed at least one of these and wondered what happened. The honest answer is that all three are part of the same season on the Square, but they are not the same kind of change, and the difference tells you something about how this particular block actually works.
The corner that just spent $2.2 million to stay put
Underwood Jewelers, at 2044 San Marco Blvd., is not going anywhere. That is the point of the $2.2 million renovation the city permitted this past March. Jeff Thompson Construction Co. is handling a full facade rebuild and interior remodel of the 9,260-square-foot building, and the work is happening because Underwood's parent company, Bromberg and Co., bought the property outright in June 2025 for $4.865 million.
Clayton Bromberg, the company's chairman, put it plainly when he described the project: the building "needs to be a showplace." He also noted the practical rhythm behind it: watch brands like Rolex expect a store refresh roughly every decade, and Underwood's last one was in 2015. This is not a business testing the neighborhood. Underwood's San Marco branch dates back to 1953, more than seventy years on this same stretch of San Marco Boulevard. A business that has been here that long, spending that kind of money on a building it owns, is a business planning for the next decade rather than the next lease renewal.
Sherwin-Williams occupies one end of that same building, and Theatre Jacksonville, the oldest community theatre in the country, sits a few doors down at 2032 San Marco Blvd. None of that is changing. The Underwood project is a facelift on a fixture, not a changing of hands.
The corner where a 25-year fixture didn't make it
A few blocks away at 1440 San Marco Blvd., the story runs the opposite direction. That address held Bistro AIX for 25 years, dating back to 1999, and it was the kind of place regulars measured time by. Owner Marcello Villani had already renamed it Bistro X and added a lighter sister concept called Limoncello Ristorante in the same space. Both closed for good on September 28, 2024. Villani pointed to changing tastes as the reason: "People are getting tired of French cuisine. They want something fresher, newer and younger."
What is there now opened in February 2026, and it looks nothing like the place it replaced. Cafe San Marco and Bar San Marco are run by Daimi Morales and David Revuelta, and the concept is deliberately smaller than what came before. Morales, who grew up in Cuba, wanted something closer to a neighborhood cafe than a full restaurant. "It was going to be tapas. Just something small. Not something big like a full restaurant," she said of the original plan. The couple's connection to the space is personal too. When they were dating, they used to sit at a table by the window facing San Marco Boulevard, in the same building where they now hold the lease.
The build-out ran about $60,000, with the biggest single expense being a $13,000 coffee maker, a detail that says something about how central the coffee service is to what they are building. Cafe San Marco runs mornings, from a 6 a.m. grab-and-go opening through a full breakfast menu at 8 and lunch service until 2 p.m. Bar San Marco takes over the same space in the evenings, Wednesday through Sunday from 5 to 10 p.m., with a Spanish-influenced tapas menu. The kitchen keeps working past the cafe's closing time too, selling pizza for pickup and delivery until around 10 p.m.
Twenty-five years of institutional memory left that building in 2024. What replaced it is a much smaller operation built around a personal story rather than a franchise playbook, on a month-to-month bet that a neighborhood cafe can hold the same corner a French bistro held for a generation.
The building that kept its bones on purpose
Then there is 1996 San Marco Blvd., the address of the old San Marco Theatre. Built in 1938 and designed by Jacksonville architect Roy Benjamin, the building's owner, TSG Realty, made a specific commitment when the space changed hands: the historic facade would stay intact. What moved in is Electric Dough Pizza Co., chef Tom Gray's third concept in the area, which opened in June 2025 inside the 4,200-square-foot theater space.
The restaurant leaned into the building's history rather than erasing it. The original film projector sits staged near the entrance, and design details echo the old theater curtains throughout the dining room. Gray, who also owns Town Hall a few storefronts away and Prati Italia at St. Johns Town Center, said the decision to put a restaurant inside the theater "seemed like a no-brainer." This is a business that treated a historic shell as an asset worth preserving rather than a constraint to design around, which is a different kind of continuity than either of the other two stories on this block.
Two different clocks on the same sidewalk
Put the three side by side and a pattern shows up that a single storefront story would miss. Underwood owns its building outright, has occupied it since 1953, and is investing seven figures precisely because it plans to stay. Electric Dough leases inside a building whose owner chose to protect its 1938 shell rather than gut it, so the history stays visible even as the tenant changes. Cafe San Marco and Bar San Marco lease a space with no such protection, in a building that has cycled through several concepts since Bistro AIX's 25-year run ended in 2024, and the newest tenants are betting on something smaller and more personal than what came before.
None of that makes one approach right and the other wrong. It does mean that if you are the kind of person who walks the Square regularly, the pace of change you see on any given block has less to do with San Marco's overall character and more to do with who owns the building underneath it. A block anchored by long-term owners moves slowly and predictably. A block full of leased storefronts moves faster, and the businesses that survive there tend to be the ones willing to bet small and personal rather than big and established.
That is worth knowing the next time a storefront on the Square goes dark for a few months. It is not necessarily a sign the neighborhood is struggling or thriving. It is usually just a sign of who holds the deed.
What it means for the walk you take tomorrow
For now, the practical version is simple. Underwood's scaffolding will likely be up for a while longer given the scope of the project, so expect some sidewalk detours near 2044 San Marco Blvd. Cafe San Marco is worth an early visit if you have not tried the morning grab-and-go yet, and Bar San Marco is the better bet if you want the tapas menu on a weekend evening. Electric Dough is still the spot if you want to see how a 1938 theater looks with a pizza oven where the concession stand used to be.
If any of this has you thinking further down the road about what it would actually mean to buy or sell property on a block like this, where ownership history shapes so much of what you see day to day, that is a conversation Ernie McKinney has regularly with people looking at San Marco. Schedule a Call whenever that day comes.
