Historic homes have some truly great stories to tell. Elements of different styles from decades gone by, famous past residents or visiting luminaries, and local legends as old as the hills make estates of a certain vintage irresistible to buyers who love a captivating tale. In Europe and North America, these homes all hail from different time periods, but they share connections to the histories of their cities or towns, important designers and architects, and the jet-setters of their particular eras.

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Sears Cottage
Islesboro, Maine

One of the grandest waterfront estates on the island of Isleboro, Maine, Sears Cottage commands more than 21 acres with over 1,110 feet of shorefront on Gilkey Harbor. The summer “cottage” was commissioned in 1907 Richard Dudley “Dick” Sears, an American tennis player who won the first seven consecutive US National Championships from 1881 to 1887. The greatest player of his generation, he still holds the record for the most singles titles (seven) and doubles titles (six) at what is now the US Open; he was also the first American to play in the men’s final at the Wimbledon Championships. The two-story residence is characteristic of the Renaissance Revival Style with its stucco façade, hip roof, sun porch to the south end and ell wing to the north. The house is complemented by a carriage house/stable, billiards house, guest cottage with four-car garage, and deepwater dock. The grounds are landscaped with lawns, flowering shrubs, specimen trees, formal and informal gardens interspersed with natural Maine woods.

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The Branford-Horry House
Charleston, South Carolina

Considered one of Charleston’s most significant colonial residences, the Branford-Horry House is a unique pre-Revolutionary dwelling in the heart of the city’s oldest neighborhood. Built circa 1767, the three-story brick and stucco house is associated with Charleston’s earliest acts of historic preservation and was listed on the National Register of Historic Places in 1970. The two-story portico, which was constructed in the 19th century, defines the residence as a rare and exceptional architectural resource within the Charleston Historic District. The Georgian interiors have remained beautifully intact, from the cypress paneling, cornices, and pilasters, to the elaborately carved mahogany mantelpieces. Grandly scaled for elegant entertaining, the 6,217-square-foot living spaces include an entrance hall, several reception rooms, formal dining room, a modern kitchen, and private quarters comprising four bedrooms and four and a half bathrooms.

Vintage Florida Glam
Westway Drive, Sarasota, Florida

This four-bedroom 1956 estate on Florida’s Gulf Coast offers a suite of luxury amenities—and enough Rat Pack-era lore to fascinate connoisseurs of 1950s pop culture. “Blue Velvet” crooner Bobby Vinton once called it home, and the blue velvet drapes he installed are still in place. A French count and filmmaker who once owned the property had an enormous vault installed to protect his art collection when he wasn’t in residence. A subsequent owner, the CEO of a boating company called Wellcraft, had to seek the protection of the FBI. The estate was designed by noted post-war modernist architect Philip Hiss, known as the developer of Lido Shores. Hiss traveled extensively and drew inspiration from the architecture of Bali, where high temperatures have always called for innovation to keep interiors cool and breezy. At nearly 12,000 square feet, including the 9,000-square-foot main residence, this tropical home has been fully updated and boasts floor-to-ceiling windows that open onto stunning water views. The outdoor areas include a spa, cabana with dry sauna, and even a tropical bar area, as well as deep-water dockage for boats. An ideal setting in any era, this home’s storied past lends it an extra dose of vintage charm.

Private Island Paradise
Greece

A private island within an hour of Athens International Airport, this property is a rare offering with a pedigree and history rivaling the finest properties in Greece. Since its heyday in the 1960s, the island has hosted many celebrities and dignitaries, including the Beatles, Sir. Winston Churchill, the Greek royal family, and Ethiopian Emperor Haile Selassie. The 12.45-acre island is an oasis of tranquility with mature olive, pistachio, and cypress trees, surrounded by pristine beaches and turquoise waters replete with marine life. There are nine separate buildings, including a four-bedroom main residence, a guest house, and two-bedroom staff house. The picturesque chapel, host to family weddings and baptisms over the years, features wall murals painted by the property’s former owner, who was an artist. Nearby is the Venetian stone tower that served as his atelier. The infrastructure includes roads and pathways, a main dock, and an independent water source.