America is turning 250, but these commercial properties are older

As America celebrates its 250th anniversary, there's a lot of talk about how much has changed since the nation's founding. But when it comes to commercial real estate, there are a number of buildings that have endured.

From a 375-year-old hotel in Puerto Rico to a 272-year-old mill in Maryland, some American properties that were already doing business before the Declaration of Independence was signed are still in use.

Just as conversions have become common in the post-pandemic era, especially the conversion of office buildings into multifamily properties, some of the oldest commercial buildings in the United States have changed their uses over the centuries to adapt to shifting demand. The 320-year-old Ye Olde Centerton Inn in New Jersey, for example, dropped the hotel part of its business, but it has always included a restaurant.

The historic structures often require frequent renovations or repairs, but the properties' owners are determined to foot the bill to preserve the historic buildings — and help pay for restoration by attracting tourists with the lure of history.

A handful of property owners perform maintenance work themselves, like Brian Goode at Ye Olde Centerton Inn in Pittsgrove, New Jersey. But he said owners of very old properties need to be careful when tackling a repair job on their own: "You may think you are replacing a wall, but you end up with something bigger," Goode told CoStar News.

The overall number of commercial buildings that predate the ratification of the Declaration of Independence in 1776 and are still home to businesses is small. In many instances, it's a wonder they survived this long, said Sherri Marsh Johns, an architectural historian who has studied the historic Old Wye Mill in Maryland that supplied flour to George Washington's troops during the War for Independence.

"Mills are located on a waterway, so they're subject to destruction by flooding during extreme weather," Johns said. "The building's survival is quite amazing given we have letters from the 18th century discussing storm damage."

Here are some of the oldest U.S. commercial buildings that are still occupied and open for business.

Christopher Columbus reached Puerto Rico in 1493, and the Spaniard Juan Ponce de León conquered the island in 1508. Because of the early dates of these European explorers' arrival in Puerto Rico, the U.S. territory has several of the nation's oldest buildings still in use.

Hotel El Convento, founded in 1651 and located in the Old San Juan district, is one of the oldest. An $8 million renovation was completed in March, with all guest rooms and public areas receiving a full upgrade, said Henry Neumann, the hotel's general manager.

The ownership group at locally based International Hospitality Development is "deeply committed to the preservation [of the hotel] and protecting its historical, cultural and architectural significance," Neumann said.

The 81-room Hotel El Convento is far from the oldest building in San Juan. La Casa Blanca, a museum, and La Fortaleza, the residence and workplace of Puerto Rico's governor, both opened in the 1500s, and the San Juan City Hall building opened in 1604. The U.S. annexed Puerto Rico as a territory in 1898.

The King of Prussia Inn is neither an inn nor has it been located in the same spot for its entire 307-year history. But the building endures as an office — one dedicated to furthering commerce, no less.

The stone building was constructed in 1719. Roadwork in the 1950s surrounded the building with two sides of U.S. Highway 202. The location rendered the building essentially unusable, and it sat vacant for decades. State and local officials eventually decided to relocate it.

After multiple groups raised money, the building was moved in 2020 about a half mile to its current location on Bill Smith Boulevard, according to the King of Prussia Historical Society. The building was then renovated, and structural repairs were completed.

It's now owned and occupied by the Montgomery County Chamber of Commerce. The organization is hosting a celebration of the nation's 250th anniversary on Aug. 20.

It's tough for a historic building to stand out in a crowd when it's surrounded by other structures that are almost as old and at least as culturally significant.

Union Oyster House in downtown Boston fits that bill. The restaurant, opened in 1716, was frequently visited by President John F. Kennedy — a booth is named for him — and is known for its menu of daily-caught oysters and seafood. It also serves a beer made by the local Samuel Adams brewery that's not available anywhere else.

Nearby is Faneuil Hall, a building that opened in 1742 and continues to serve as a public market and civic space. Also a few steps away is Bell in Hand, a bar that opened in 1795.

Joe Milano, owner of Union Oyster House, tries to maintain the sense of history that permeates the walls of his restaurant.

"It must be preserved as a museum, as living history," Milano said.

The most recent renovation, in 1995, added a gift shop and private dining rooms on the upper floors. All the work was carefully monitored by the city's Landmarks Commission, Milano said.

The Old Wye Mill on Maryland's Eastern Shore is a notable example of a historic building that still serves a practical, commercial function.

The 2,400-square-foot building is the home of a working grist mill. A grain mill has been located on the same site since at least 1668, though the current building dates to 1754, according to the Cloverfields Preservation Foundation, the property's owner. It's the oldest water-powered mill in the U.S. and the oldest continuously operating business in Maryland, according to the Stories of the Chesapeake Heritage Area organization.

The grist produces and sells flour, cornmeal and corn grits using machinery that dates to the period between 1790 and 1810. The Maryland Heritage Areas Authority recently completed an upgrade of the Old Wye Mill to improve the parking area and repair the main entrance.

The Friends of Old Wye Mill, a nonprofit organization that manages the business on behalf of the Cloverfields Preservation Foundation, did not respond to phone and email requests for comment.

At least a dozen small restaurants and bars in New England and the mid-Atlantic date back to the 18th century. Most of these quaint dining and drinking establishments are locally owned and operated, such as White Horse Tavern in Newport, Rhode Island, and the Red Fox Inn & Tavern in Middleburg, Virginia.

Milleridge Inn in Jericho, New York, is in a class by itself. For one, the 354-year-old restaurant, originally built as a two-bedroom house, no longer offers lodging and is not situated in a rural area or small town like many similar properties. Instead, Milleridge Inn is squeezed between two major Long Island highways, Interstate 495 and Jericho Parkway.

Then there are the owners. Kimco Realty, one of the largest U.S. real estate investment trusts that specializes in retail properties, has owned Milleridge Inn since 2015. However, Kimco's ownership is not as unusual as it might seem. The property shares a parking lot with the office building where Kimco's headquarters is located. The same parking lot also serves the Kimco-owned Jericho Commons shopping center.

The Dover Group, an event planner based in Freeport, New York, manages Milleridge Inn and rents the facility for weddings and other events. The Milleridge Inn site also includes shops and a small cafe.

Jennifer Maisch, a spokesperson for Kimco Realty, declined to comment. The restaurant's general manager did not respond to calls and emails seeking a comment.

When a building is about 340 years old, the backlog of deferred maintenance projects seems to never end, Burnie Maybank said.

The roof at the Tavern at Rainbow Row tends to leak, and some rotten wood needs to be replaced, said Maybank, who owns the liquor store in Charleston, South Carolina. Those are just two items on the list, he said.

Then there is the issue of neighbors. In 2021, Maybank placed chairs and tables on the sidewalk outside the store so customers had a place to sit while trying out products. Neighbors sued, claiming the Tavern at Rainbow Row was not authorized to operate a restaurant and asked the court to prohibit the store's customers from parking in a nearby lot. A state judge dismissed the lawsuit in July 2025. The Tavern at Rainbow Row continues to sell liquor and wine, but it does not operate a bar on the premises, Maybank said.

The Tavern at Rainbow Row is the oldest liquor store in North America and the oldest commercial building in Charleston, Maybank said. The name Rainbow Row refers to a group of 13 adjacent buildings on East Bay Street painted in pastel colors. Tavern at Rainbow Row opened as a general goods store in 1686 and probably sold liquor, Maybank said.

Some owners of historic properties in the U.S. take advantage of a federal tax credit to help pay for needed renovations and building repairs.

Not Goode, the owner and general manager of Ye Olde Centerton Inn in Pittsgrove, New Jersey.

The Federal Historic Preservation Tax Incentive program, administered by the National Park Service, provides a tax credit equal to 20% of qualified expenses. Goode eschews the federal tax incentive because of what he sees as its onerous requirements.

The program mandates that owners, if they are renovating, restore the building to precisely how it looked around the time it opened. Meeting those exacting standards ends up costing more than the value of virtually any renovation, Goode said.

"I would do that if I was independently wealthy," Goode said.

Instead, Goode performs most necessary repairs himself. For a South Jersey building that dates to 1706 and was likely built to be a tavern and inn, it's a lot of work.

"It was in average shape when I bought it," Goode said. "I may have upgraded it by now to average-plus."

Goode has replaced tile in the men's bathroom and repaired the leaky roof, among other tasks. Any project requires careful observations because an old building hides its flaws well, he said.

"You've got to be careful with what you unearth," Goode said. "You fix one thing and you realize you need to fix something else. Then you fix that and realized it didn't work and you have to do something else. I went through years of that."

The first floor of Fraunces Tavern in the Financial District of Manhattan is a restaurant that serves standard American gastropub fare, and it was a restaurant before July 4, 1776.

The Fraunces Tavern building and nearby streets and sidewalks have been the site of a number of historic events in American history. The one-time family home became the central location in New York for American Revolutionary activities. Diners have included George Washington, John Hancock, Alexander Hamilton and Aaron Burr. The New York Provincial Congress hosted a banquet there in 1776 at which George Washington addressed the crowd. In 1783, Washington bid farewell to his officers at the site at the end of the Revolutionary War.

In the following decades, Fraunces Tavern passed through a succession of owners and underwent numerous changes in function that reflected the evolving needs of a growing New York City. At various points, it served not only as office space but also as a commercial boarding house, accommodating residents and visitors alike.

Despite its continued use, the building faced significant challenges over time. A series of fires in the mid-1800s destroyed much of the original structure. Recognizing the historical importance of the site, the city of New York assumed control of the property in 1903 and later transferred ownership to the Sons of the Revolution, a group that's still the restaurant's commercial landlord.

In 1640, the Plymouth Colony granted 6 acres to Thomas Dexter on a pond near the town of Sandwich, Massachusetts. Dexter built a grain mill on his parcel, and cornmeal production has taken place at the Cape Cod site ever since.

Milling operations have been temporarily halted at various times over the centuries. The mill was recently closed for the installation of a new wooden millwheel.

For a period during the Industrial Revolution in the mid-19th century, the mill replaced its wooden wheel with one made of iron to speed up production. The town of Sandwich, owner of the mill, later readopted a wooden wheel.

The quaint, wooden building that houses the mill equipment is one of the most photographed locations in New England, according to the tourism group Cape Cod Xplore.

Some commercial buildings still stand, but their uses have shifted to reflect the changing tastes of America. That is the case with the Old Corner Bookstore in Boston.

Opened in 1718, it has hosted a variety of commercial tenants, including an apothecary shop, newspaper offices, an internet cafe, a book publisher and a jewelry retailer. A proposal to demolish the structure in the 1960s led to the creation of Historic Boston, a nonprofit preservation group that still owns the building.

It's also been occupied over the decades by several different bookstores. The last bookstore to call the structure home, the Old Corner Bookstore, closed in 1903 but gave the building its name.

While residents of Boston once flocked to the building for edification, the structure now houses a Chipotle.