When Jesse Iliff was a boy, trips to St. Helena Island in the Severn River were full of enchantment.

The brick walls around the mansion were medieval battlements. The menagerie pens held exotic beasts. An old gambling vault was a prison.

“It was a really magical, kind of wonderland,” said Iliff, executive director of the Severn River Association. His grandfather had owned the fantasy island estate in the 1970s and 1980s.

Now, the brick mansion with half of St. Helena Island — the only habitable island in the Severn River — is for sale again.

Listed for $2.98 million, the nearly 7-acre property comes with a 7,100-square-foot mansion, guest cottage, water tower-turned-office and pier. Arrive by boat or by helicopter.

The estate occupies about half of the island in the middle of Round Bay, just off the shores of Crownsville in Anne Arundel County. The Pinkard family of Baltimore have owned the other half of the island for decades as a summer home.

“This is often the type of property that would be handed down from generation to generation and rarely comes to the open market,” said Brad Kappel, the listing agent.

In fact, Kappel is having a moment himself, with concurrent listings of luxury waterfront homes. He’s working to finalize a sale of Dobbins Island in the Magothy River, a popular raft-up spot for summer boaters. That’s listed for $1.98 million.

He’s selling the former Capuchin monastery known as the Friary. The sprawling Severn River estate owned by the Phillips Seafood CEO is listed for $19.9 million.

And he sold a house this spring on the shores of West Annapolis for $17.5 million. That was the highest waterfront sale in Maryland history, he said.

Rich people are pouring money into the Severn River waterfront, Kappel said.

In this glitzy portfolio, St. Helena Island holds a singular place for its colorful, even illicit, history.

There are no roads on the island and a few homes in addition to the century-old brick mansion. Built in the 1920s by Paul M. Burnett, chairman of the board of the Monumental Life Insurance Company, the mansion was modeled off Baltimore’s famous Homewood House.

“Burnett left enduring mysteries by building into the mansion a series of safes, including a safe within a safe, and a secret compartment in a closet,” The Washington Post wrote in the 1980s after visiting the grounds.

Burnett sold the island in the 1940s to Eugene J.C. Raney, of Montgomery County, a beer distributor, firefighter and owner of bowling alleys.

In the summer of 1951, Anne Arundel County Police raided the island and found Raney and partners operating an illegal gambling den. Officers seized the nickel slot machines known as “one-armed bandits.” Raney was convicted of gambling violations in Anne Arundel Circuit Court and fined $500.

After a riot and escape at nearby Crownsville State Hospital two years later, one county official suggested the state buy the island and build a prison like a Maryland Alcatraz — a proposal that fizzled.

Then in May 1955, county police returned to search the island after a pickle jar washed ashore with an alarming note.

“Help. Am on St. Helena Island, Severn River. Am being chased by crazy occupant who eats people alive. Get police and come back. Arthur Smite,” according to a May 1955 article in The Post. Police concluded it was a hoax.

The Johns Hopkins University eye doctor and professor Dr. Charles Iliff owned the island in the 1970s and 1980s. His grandson, Jesse, still remembers the frightening vault. Island legend has it that the enclosed pen once held a herd of miniature deer.

In the late 1990s, shoreside neighbors opposed plans by the company Fantasy Island Management Inc. to turn the island into a wedding and party destination. The neighbors complained about the blaring of “Louie Louie” across the water, The Baltimore Sun reported. The island was also owned by a judge, a prominent lawyer, and a real estate tycoon.

In 2019, David Clickner, a wood-floor wholesaler in Glen Burnie, bought the mansion and half of the island for $2.37 million, according to state tax records.

Clickner also owns Dobbins Island in the Magothy. His plans to build a home on Dobbins and limit public access there brought years of litigation.

Now, he appears to be giving up island life. He did not respond to a message.

With Dobbins Island under contract, his St. Helena estate heads to auction on Oct. 22. That’s if no one buys the property for the listing price of almost $3 million.

Opening bids are expected between $1 million and $2 million.

The story has been updated to reflect Dr. Charles Iliff owned the island in the 1970s, too.