Mysterious island off Chesapeake Bay lists for $2.1M

Tippity Wichity might have been a bordello and illegal distillery

Gail Harmon with Tippity Wichity Island (Harmon, Curran, Spielberg & Eisenberg; ​​​​​Sotheby’s International Realty)
Gail Harmon with Tippity Wichity Island (Harmon, Curran, Spielberg & Eisenberg; ​​​​​Sotheby’s International Realty)

Private islands with mysterious – perhaps shady – histories are the best kind, right?

One such landmass – the 5-acre Tippity Wichity Island, which is a 90-minute drive outside Washington, D.C., just off the Chesapeake Bay – hit the market recently for $2.1 million, Insider reports.

The island includes a three-bedroom cottage with an open-plan living and dining room, as well as a wood-burning stove. There’s also a dock, beach, launch area for kayaks and canoes and a heated outdoor swimming pool.

TTR Southeby’s has the listing for the island.

One of Tippity Wichity’s major selling points, however, is its colorful history.

It’s been owned by Gail and John Harmon since the 1970s, when they and another couple bought it after seeing an ad in the classified section of a local newspaper. (The Harmons bought the other couple’s share about a decade ago.)

The Harmons set about unraveling the island’s fascinating, curious past, with some evidence suggesting that, just after the Civil War, it served as a bordello possibly operated by a soldier named Capt. Henry Howgate, who had his own murky narrative that could include convictions for fraud and embezzlement, Insider reported.

The name “Tippity Wichity” could serve as a clue to its former use, as locals believe the name is a derivative of “Tippling and Witchery Island,” which was a “house of ill-repute” after the war, the outlet reported.

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The island also could have served as home to an illegal distillery during the Prohibition Era, which ended in the early 1930s. A friend told Gail Harmon that their bootlegger father would transport casks of whiskey to the island during that era.

Tippity Wichity now serves a more above-board purpose as a vacation getaway.

But GailHarmon said that, given its proximity to shore – it’s a 5-minute boat ride from the mainland – and an electric system that includes a backup generator, the island could serve as a full-time residence.

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

Tippity Wichity isn’t the only private island to hit the market this year.

Much larger in scale and price, the 350-acre Cromwell Island in Montana, which includes a 45,000-square-foot villa, listed in May for $72 million.

Also in May, Great Harbour Mansion, situated on an island on Lake George at Cooper’s Point, went back on the market for $8.4 million.

– Ted Glanzer