Sleeper is said to have been tutored at home due to his frail health, and no trace of any formal education has been found. Some oral histories state that he studied at the Ecole des Beaux-Arts in Paris, though this claim is not supported by that institution’s records. When Henry reached the age of eleven, the Sleeper family began spending summers in their new home on Marblehead Neck, designed by architect Arthur Little. Henry’s father built the home in 1888 and died while summering there three years later. After his mother sold the home in 1902, Sleeper saw that he would have to purchase another summer retreat for his family to escape the city heat. When he visited Eastern Point in 1906, he was determined that this would be the site of their new refuge.
The social enclave of Eastern Point was created in the 1880s by wealthy Bostonians John and David Greenough, who formed the Eastern Point Associates to purchase farmland in east Gloucester from the heirs of farmer Thomas Niles. They bought the land on November 12, 1887, for $100,000 and began laying out streets and dividing the parcel into building lots. On a map of the subdivision produced for the Associates in 1889, the future site of Beauport occupied the lot designated as number 101. In 1901 the lot was sold to well-known Cape Ann hotel builder George O. Stacey, who already had sites including the Moorland Hotel, the Magnolia Hotel, and the Hawthorne Inn to his credit. One year later, Stacey purchased three adjoining lots and a few parcels across the road for the 300-room Colonial Arms Hotel which opened for the season in 1904. Stacey separated the southernmost lot, 101, and sold it to Henry Sleeper on August 13, 1907. Sleeper began construction in the fall of that year and occupied Beauport by May 12, 1908, when Andrew was his first houseguest.
Sleeper’s original Little Beauport, named after Le Beau Port, French explorer Samuel de Champlain’s description of Gloucester Harbor, was a relatively small cottage situated on a modest lot. Henry soon became the last official member of “Dabsville,” a self-imposed acronym invented by a group of artists and intellectuals who inhabited homes along a small section of Eastern Point Boulevard. The D stood for Joanna Davidge of Virginia, proprietress of Miss Davidge’s classes, a finishing school for young ladies in New York, who inhabited a cottage called Pierlane next to Red Roof. A, of course, was for its owner, A. Piatt Andrew. B was for well-regarded Philadelphia portrait painter Cecilia Beaux who resided in Green Alley, the southernmost Dabsville property. S stood for Henry Sleeper but also for South Carolina native Caroline Sinkler, whose home was sandwiched between Red Roof and Beauport. She called her cottage Wrong Roof in a joking jab at Andrew’s home. Despite that colorful bit of levity, Miss Sinkler had experienced a tragedy that left an equally indelible image. Shortly before her winter wedding, her fiancé, John Stewardson of Philadelphia, drowned while skating on the Schuylkill River. From that day forward, Sinkler wore mourning clothes in hues of lavender and black which earned her the name of “the Lavender Lady” among the members of Dabsville. Completing the assortment of unique individuals was the compulsive collector, Mistress of Fenway Court, Isabella Stewart Gardner as an honorary member. For Henry Davis Sleeper, this group of friends was his source of entertainment and inspiration for his great pride, Beauport.
Shortly after Sleeper purchased the lot on Eastern Point, he and Andrew discovered the William Cogswell house in Essex while on their way to visit Emily Tyson, who had recently restored Hamilton House in South Berwick, Maine. Sleeper eventually purchased the interior of this dilapidated eighteenth-century farmhouse and used the paneling and shutters to form the Cogswell’s Hall and the Green Dining Room, both on the original 1908 floor plan. It was this purchase that began Sleeper’s interest in architectural salvage which he used throughout his summer home, making his new house appear old.