Tippity Wichity Island With Dark Past for Sale Near the Chesapeake Bay

Tippity Wichity, a private island in a sheltered cove near the Chesapeake Bay, is on the market for $2.1 million.

Down river from the Chesapeake Bay lies a 5-acre landmass known as Tippity Wichity Island, just a 90-minute drive from Washington, DC.

It recently hit the market with Sotheby’s for $2.1 million.

Current owners Gail and John Harmon, a couple in their late seventies, bought the island in the 1970s after seeing a small ad for it in The Washingtonian, a local paper. Gail, a retired lawyer, told Insider they were on the hunt for a vacation home by the water when they moved to Washington, DC, for a military commitment John had at the time.

That’s when a listing for the Tippity Wichity listing caught her eye, which she said included a quote from William Shakespeare’s play, “Richard II,” that read: “This other Eden, demi-paradise, This fortress built by Nature for herself.”

But there’s more to the island than meets the eye, Gail said. She believes it was once run as a “house of ill repute.”

Records show that one of the first residents of Tippity Wichity Island was a soldier by the name of Captain Henry Howgate, the Sotheby’s listing states. And depending on what you believe, it adds, Howgate was either a confederate or union soldier, who purchased the island in 1879 after the civil war.

Regardless of the side he was on, Gail believes he was up to no good on the island. “It’s a house of ill repute,” she said.

An article published in 1895 by The News, a publication from Maryland, reported that a person by the name of Captain Henry Howgate was later convicted for forgery and embezzlement. It’s unclear if he was the same Howgate to have once owned Tippity Wichity.

Local lore suggests the island’s unique name hints at its storied past.

While passing Tippity Wichity Island on a Potomac River cruise in 2017, Jody Argo Schroath reported in Chesapeake Bay Magazine that some locals believe the name suggests a bordello was built on the island after the civil war.

Schroath wrote that it’s “a corruption of the name ‘Tippling and Witchery Island,’ named for a house of ill-repute located there following the Civil War.”

David DeSantis, the broker in charge of the listing, told Insider it’s not hard to believe the “debaucherous” stories told about the island’s history. “Washington, DC, was still a small outpost in the 1800s,” he said. “It was the wilderness. There was a lot of piracy on the water, it was sort of a lawless environment.”

What’s more, Gail said she has reason to believe Tippity Wichity was home to an illegal distillery during prohibition.

A close friend of Gail and John who grew up near the island told the couple that as a child they would come to the island transporting big casks of whiskey with their father, who was a bootlegger.

If true, that would mean the island housed an illegal distillery during the prohibition era when the manufacture, sale, and transportation of alcohol within the US was outlawed. It lasted until 1933.

“It was a perfect place to meet your purchasers,” Gail said. “If the federal government came up the river, you could go roll off the back.”

Potentially murky history aside, Gail and John fell in love with the island. They ended up buying it as a timeshare for $125,000.

When they enquired about the property, Gail said they couldn’t believe no one else had snatched it up first. “We said, ‘We don’t believe it. What’s wrong with it?'” she told Insider. Her first thoughts were that maybe other prospective buyers were put off by a nuclear power plant 20 miles away from it.

But when they saw Tippity Wichity Island for the first time, she said they were “blown away by how wonderful it was.”

They ended up buying it with another couple as a timeshare. For 30 years, she said they alternated weekends with the other couple until they decided to sell their share to Gail and John roughly 10 years ago.

“It worked out quite well,” Gail said. “We knew people who lost friendships because they shared vacation property.”

The island came with a fully-furnished house, which Gail said they cleared out when they made renovations.

“The house was furnished with kind of cute 1950s furniture,” she said. But as they began renovating the three-bedroom home, they eventually sold most of the furnishing left over from the previous owners, who decided to sell when they were getting older, she said.

A few changes they made included making the house open plan and adding sliding doors to the principal bedroom and kitchen.

DeSantis said the Harmons remodeled the property into a modest but charming summer home.

“By current standards of what people think of in the US as beachfront summer homes, this is still pretty modest,” DeSantis said. “But it’s got a lot of charm.”

The house is more like an “expanded cottage,” he added. “It’s not like living in a mansion on an island. You could turn it into that if you wanted to but that’s not their vibe.”

While the Harmons never lived on the island full-time, DeSantis said new owners could make it a year-round residence.

According to Gail, the island is a mere five-minute boat ride from a jetty on the mainland. It’s so close, in fact, that she said her son and his friend once swam it when they were kids.

The proximity to shore and the fact that the island is equipped with a functional electric system and a backup generator means that it could be used as a full-time residence, DeSantis said.

“There is no reason why, if you didn’t mind the inconvenience of having to get into a boat every day if you wanted to go somewhere,” he added.

It wouldn’t be the first time it’s been someone’s primary home, according to Gail.

“The people who built the house lived there full-time for a while,” Gail said.

She said she heard through friends that the former residents raised a daughter on the island, who would commute to school in a small boat.

Large windows in the great room offer sweeping views of the surrounding waters.

The open-plan living and dining room is the central gathering place in the home, the listing states.

It also has a wood-burning fireplace and large windows that provide views down the river as well as access to the back porch and the garden.

According to Gail, the winter sunrises are “beautiful” to watch through the windows in the dining area. “The sun of course moves a bit during the course of the year,” she said. “And in the winter it’s in a position that is just glorious.”

One of Gail’s favorite places to cozy up on the island is the enclosed gazebo because it offers spectacular sunset views.

“We have this wonderful octagonal screened porch, which is quite beautiful and it provides a good view of the sunset when you’re having dinner out there,” she said.

According to the listing, future owners can enjoy dining there year-round since the gazebo is largely protected from the elements.

Gail and John also built a pool on the island, where she said they hosted many friends over the decades.

“We would have big parties on holiday weekends for friends from Washington and local friends,” Gail said.

On warmer days, everyone could congregate in spots like the pool, which they built on the island after buying it, she added.

While you may think living on an island may be lonely, Gail said her experience has been the opposite.

From joining the local yacht club to water skiing with neighbors and exploring the nearby picturesque town surrounding St. Mary’s College of Maryland, Gail said there’s plenty of opportunity for new owners to enjoy a rich social life as well as the privacy that comes with owning an island.

“Isolated sounds absolutely the opposite of what I’m saying,” she said, adding they never felt lonely because of how many close friends they’ve made in the local riverside community.

If interested parties are nature lovers, Gail says the ecosystem of Tippity Wichity is rich with wildlife and beauty.

“We have a number of great blue herons nesting on the island, and they are just beautiful strange birds,” she said. Birdwatchers can also expect to see a host of other species, including bluebirds, seagulls, woodpeckers, and flycatchers, Gail added.

And recently, Tippity Wichity Island has become the home of a single fox, which Gail believes made its way onto the island from the mainland last winter when a thin layer of ice covered the river.

“We used to have woodchucks, but now that we have the fox, we don’t have woodchucks,” she added.

As both Gail and John are nearing 80, she said age played a factor in their decision to sell the island.

“It’s bittersweet,” Gail said of her and John’s decision to leave Tippity Wichity for good.

Both she and John are 79, which is part of the reason why they’ve decided to sell. “We’re just getting older and the idea of jumping in and out of the boat is a bit of a challenge,” she added.

They also didn’t want to leave their children, who live in Boston, with the burden of selling the house.

Even so, Gail said they won’t be going too far. “Our plan is to get a small house on the land with a water view,” she said.