Real Estate

This Private Island For Sale Off the Chesapeake Comes With a Fascinating Past

Tippity Wichity Island once housed a secret “bordello” and distillery.

This Private Island For Sale Off the Chesapeake Comes With a Fascinating Past
Tippity Wichity Island. Photo by Townsend Visuals LLC.

When Gail and John Harmon considered buying a vacation property somewhere near their DC home, they imagined finding a place with a water view. They got a lot more than that when they bought their private island on the St. Mary’s River. 

The couple originally discovered the island via a classified ad in the back of a 1977 issue of Washingtonian magazine. The Harmons purchased the island in 1978, and it’s been their refuge ever since.

“We’ve used the island in every season, not just as a summer place,” says Gail. “We’ve had to break ice in the river with the bow of our boat to get there in the winter, but this is our idea of fun and adventure.”

Good news: It could soon be your refuge, too—if you have $2.1 million to spare, that is. The property, known as Tippity Wichity Island, is listed for sale via TTR Sotheby’s. For that price, you’ll get a five-acre island, a three-bedroom house, a dock with a boat lift, a small beach, and a launch area for kayaks and canoes and a nature trail. A heated swimming pool surrounded by a garden is adjacent to the house.

An aerial shot of the island and the house. Photo by Townsend Visuals LLC.
The house and the dock. Photo by Townsend Visuals LLC.

You’ll also get a lot of history. 

The exact story of Tippity Wichity is murky, according to the listing. Some claim it was originally a Native American settlement: “My husband likes to joke that the name comes from this being a Native American burial ground to spook people who are staying overnight,” says Gail. 

While it is known that Captain Henry Howgate purchased the island after the Civil War, it’s up for debate whether he was a former Confederate or Union troop. Either way, Howgate used the island as a stop for traders traveling along the Chesapeake, opening a distillery and what Gail calls “a big Victorian-style house that was used as a bordello” after similar spots in Alexandria were forced to close. 

That house burned down before the Harmons bought the island. Some people think “Tippity” refers to being tipsy—a nod to its former inhabitant, says Gail. According to local legend, it’s an abbreviation for the name “Tippling and Witchery Island,” says a Chesapeake Bay magazine story.

The view of the St. Mary’s River from the dock. Photo by Townsend Visuals LLC.
The island is five acres. Photo by Townsend Visuals LLC.
Visitors access the island via a five-minute boat ride from the nearby shoreline. Photo by Townsend Visuals LLC.

Its recent history has been much more PG-rated: When the Harmons purchased Tippity Wichity for $125,000, the island included a simple 1950s-style ranch house with three bedrooms and two full bathrooms. The couple redid the kitchen and bunk room and added a deck, sliding glass doors, and a screened porch for watching the sunset. 

“We’ve had big parties for the Fourth of July and Labor Day with 20 or more friends from DC and from the local yacht club,” Gail says. “When our son was in middle school, we put up two big tents, one for the boys and one for the girls, for a weekend of waterskiing and swimming.”

The view from the deck. Photo by Townsend Visuals LLC.
The house comes with an octagonal screened-in porch. Photo by Townsend Visuals LLC.
The heated pool. Photo by Townsend Visuals LLC.

In the fall and winter, friends and family gather in the open great room around a central wood-burning fireplace.

“When you’re on the island, you feel very alone because there are very few lights around,” says Gail. “It’s a very special place if you love nature and the water.”

The deck leading to the house. Photo by Townsend Visuals LLC.
The “great room.” Photo by Townsend Visuals LLC.
The dining area overlooks the view of the water. Photo by Townsend Visuals LLC.

Tippity Wichity is about a 90-minute drive from DC and comes with an easement on the mainland where the owners can leave a small motorboat for the five-minute ride across the water to the island.

St. Mary’s College, where Gail is a board member, is about a 10-minute boat ride from the island, and Leonardtown is nearby for restaurants and shops.

The island also sits about 10 feet above the water, so it’s protected from floods and rising sea levels, Gail says. Mean low water is about six feet, so the owners and their friends can dock sailboats and powerboats between trips down the St. Mary’s River, across the Potomac, and into the Chesapeake Bay.

Being on Tippity Wichity is like being on an adventure, and the Harmons are ready to give someone else a shot at it, says Gail: “Now that we’re nearly 80, we decided it’s not a great idea to be jumping into boats to reach the island.”

Michele Lerner

Michele Lerner ([email protected]) covers real estate, interior design, and personal finance.