Walk Connecticut Avenue between Macomb and Newark on a Saturday morning and you'll pass three storefronts that changed hands in the last eight months, plus one that hasn't changed anything since March 2020. That gap is the story. The turnover happening right now on this stretch of Cleveland Park isn't coming from new construction or a developer breaking ground. It's coming from operators who took over buildings that already existed, kept the bones, and moved fast. The one project that actually requires tearing into a building and reinventing it from the studs out is the one still sitting dark.
If you've noticed the block filling back in but can't quite name why it feels different than it did a year ago, this is why. The fast movers didn't build anything. The slow mover is trying to build something entirely new inside a 90-year-old shell, and that's a much harder job.
Same Building, New Sign
Highlands Tavern opened at 3421 Connecticut Avenue NW before the end of August, taking over the exact address that had been home to Cleveland Park Bar & Grill for years. The liquor license placard posted outside months earlier even said so directly, noting the space was previously home to Cleveland Park Bar and Grill and listing a total occupancy of 117, an 87-person indoor capacity with seating for 77, plus a summer garden capacity of 30 with seating for 29.
What changed is the concept, not the building. Highlands Tavern is a family-friendly, multi-level restaurant and bar co-founded by George Grau, a D.C. native and Culinary Institute of America graduate who runs the scratch kitchen, and Ki Yoon, who also co-owns Magruders. Day-to-day operations and the beverage program fall to general manager Jeffrey Diaz, a longtime DC restaurant veteran, while Chicago-born chef Mathew Douglas runs the kitchen. The menu leans into wood-fired pizzas, burgers, and a 12-tap draft list, and the ownership team has already claimed a niche most of Connecticut Avenue didn't have before: Highlands Tavern is now the official watch party spot for Notre Dame Football, with the rooftop and the multi-level dining room both wired for game day.
None of that required a new building. It required a full interior renovation and a new name on an old address, which is a very different, and much faster, kind of project.
The Wine Bar That Chose to Get Smaller
A few doors down at 3504 Connecticut Avenue NW, in a spot that used to be Yanni's near Medium Rare, Cork Wine Bar and Market opened its third location on January 8. Owners Diane Gross and Khalid Pitts have run the original Cork on 14th Street since 2008 and opened a Spring Valley location in 2021, but the Cleveland Park outpost is intentionally smaller than either. There's no server model here. It's counter service only, with a condensed kitchen, about 350 bottles on the retail shelves, and a rotating list of 15 wines by the glass.
That downsizing wasn't an accident. Gross has spoken publicly about opening into a genuinely uncertain moment for the wine and restaurant business, from tariff threats on European wine to unresolved questions about the district's tipped wage and a wave of federal layoffs hitting the local customer base. Rather than wait it out or scale up and hope, Cork scaled down and opened anyway.
"We are excited to join the Cleveland Park community. We are looking forward to meeting our new neighbors and seeing old friends and regulars, and introducing them to the new Cork, a neighborhood place where guests can gather to enjoy good food, excellent company, and delicious wine."
The bottles are still mostly old-world, still small production, still the kind of list Gross has built Cork's reputation on for nearly two decades. What's different is the format. A smaller footprint means a lower cost to open, which means a faster yes when a storefront becomes available.
A few more addresses along the same strip follow the identical pattern, existing buildings, new operators, no new square footage:
- 3421 Connecticut Ave NW — Cleveland Park Bar & Grill became Highlands Tavern
- 3504 Connecticut Ave NW — Yanni's, next to Medium Rare, became Cork Wine Bar and Market
- 3501 Connecticut Ave NW — a space that once held a California Tortilla and, before that, a Pizzeria Uno, is now home to Buffalo & Bergen, which added pastries, hot pockets, and pizza to its bagel lineup this spring
Three different owners, three different concepts, one shared strategy. Take an existing box, renovate the inside, open under a new name.
The One Address Still Waiting on Its Renovation
Then there's the Uptown Theater, which sits about a block away at 3426 Connecticut Avenue NW and hasn't shown a movie since March 2020. The single-screen, art deco theater opened in 1936, hosted the world premiere of 2001: A Space Odyssey, and was one of only 32 theaters in the country to screen Star Wars on its opening day. It's also on the National Register of Historic Places, which raises the degree of difficulty for whoever takes it on next.
In October 2024, the theater sold to Sandro Kereselidze and Tatiana Pastukhova, the husband and wife team behind Artechouse, the immersive digital art venue. They signed a 20-year lease and floated plans for something they described as a multipurpose cultural art center for immersive art, performance, and theatrical experiences. A liquor license placard went up in early 2025 listing a seating capacity of 25 and a total occupancy load of 350, numbers that suggest a much smaller footprint than the theater's historic 850-seat capacity. But as recently as this summer, local coverage tracking the project has noted there's been no visible progress since that placard went up in early 2025, a stretch now well past a year.
That silence isn't a scandal. It's what happens when a project requires an actual gut renovation of a historic building rather than a tenant swap. Highlands Tavern and Cork could open in months because the buildings they moved into didn't need historic review, didn't need a total reimagining of the interior architecture, and didn't need the kind of capital a full theater conversion demands. The Uptown does need all of that, and buildings under National Register protection move at their own pace no matter how excited the new owners are.
There's a broader signal here too. The neighborhood's own advisory commission, ANC 3C, has already voted to support taller building heights and greater density around both the Cleveland Park and Woodley Park Metro stations. That's the kind of vote that clears regulatory room for genuinely new construction down the line. But nothing about the current wave of openings has come from new buildings. It's come from operators willing to take on an existing shell and move quickly. The zoning room to build bigger exists. The activity on the ground, for the moment, is still happening inside buildings that were already standing.
What Still Anchors the Block
Not everything on this stretch is in motion. The Cleveland Park Farmers Market still runs Saturdays from 9 a.m. to 1 p.m., April through December, the same rhythm it's kept for years regardless of what's opening or closing around it. It's a small thing, but it's the kind of fixed point that makes the churn elsewhere easier to track. You notice a new tavern faster when the market stall selling the same tomatoes is still exactly where it was last August.
If you live here, the practical takeaway is simple. Expect more of this pattern before you expect the Uptown Theater to reopen. Empty storefronts on this corridor tend not to stay empty long, because the path back to open for business runs through renovation, not reconstruction. The theater is a different kind of project entirely, tied to a historic designation and a much bigger vision, and those move on a longer clock. Keep walking the block. The next name change is probably closer than the marquee lighting back up.
If you're curious what any of this means for your own corner of Cleveland Park, or just want to talk through what's changing on your street, the Rebecca Weiner Group knows this stretch of Connecticut Avenue block by block. Let's connect, no pressure, just a conversation about the neighborhood you're already living in.
