[1] A preliminary search of Anne Arundel County, Maryland records in the Annapolis Land Office identifies the first traces of the island in 1843 when it was part of the estate of the late Annapolitan Major Richard I. Jones.

Paul Burnett, a Baltimore city attorney and insurance executive, purchased the island in the late 1920s.

Between 1929–1931, Burnett built a Federal Period mansion, part of the early-twentieth-century classical revival movement, modeled after the Homewood Museum on the Johns Hopkins University campus in Baltimore.

[1] The mansion, built on a Palladian style five-part plan, occupies the crest of the island and is the centerpiece of St. Helena.

Other flooring is made from inch-thick mahogany which dented the tools of electricians and telephone mechanics who attempted to string new wiring in the 1950s.

Several other homes on the island served as housing for patients and counselors of the Burnett Hospital for Crippled Children, which operated from 1936–1943.

[1] There is also a conical roofed and a circular brick water tower on the northern point of the island, now converted to an office with a view.

[2] Following Burnett's death in 1944, the island was sold to Eugene Raney, a beer distributor and operator of several bowling alleys in Maryland but who resided in Kensington, MD (Montgomery County).

[1] During this period, St. Helena was recognized for its swanky island club, boasting a casino and regularly hosting members of Congress, judges, and other prominent citizens, including Governor William Preston Lane Jr.

Emmitt Brandt, president of Annapolis Utilities and Robert Merrick, chairman of the board of Equitable Trust occupied homes on the island.

Eugene Raney and his wife continued to use Paul Burnett's brick mansion as their personal vacation home, loaning it out to friends and business colleagues throughout and until the late 1950s.

The fire was brought under control by nearly 100 fireman rushed to the island by private boats from the Herald Harbor, Maryland.

In the late 1990s, controversy surrounded Little Round Bay and St. Helena when Keith Osborne of Fantasy Island Management Inc. purchased Prescott's mansion.

After a great deal opposition from neighbors, the Severn River Association voted to oppose all commercial activity on the island in November 1999.

The Hartman's northern 6.5 acres including the 1929 mansion were on the market in October 2014 for 3.9 million dollars[2] St. Helena Island is bordered on the east and south by the two-mile (3 km)-wide Round Bay, the only part of the generally straight and relatively narrow tidal Severn River to exceed three-quarters of a mile in width.

Little Round Bay borders the island on the north and west and may have been a meander during a time when sea level was lower and the Severn was a freshwater river.

St. Helena is home to a variety of ducks, geese, great blue herons, kingfishers, ospreys and other birds.

The Baltimore Sun Area Men and Slot Machines Seized in Raid on Island Club.