Richard Hampton Jenrette, a well-bred native of Raleigh, North Carolina, who had a successful career with the investment firm Donaldson, Lufkin & Jenrette, is a houseaholic who collects palatial homes—six, so far—in the same way that other collectors chase antiques and art. In summer and early fall, he is normally ensconced at Edgewater, a circa-1820 Palladian villa on a mile-wide stretch of the Hudson River in Barrytown, New York, about 90 miles from Manhattan. Like many Southerners of his generation, Jenrette was profoundly influenced by Gone with the Wind, and appropriately enough, most of his properties have unusual histories and share the Tara-esque white columns gestalt—Edgewater has six two-story, Doric columns facing the river.

Jenrette first saw the house in September 1969, when it was owned by the writer Gore Vidal, who had bought it after World War II. (During the war, President Roosevelt would leave nearby Hyde Park and sit on the porch of Edgewater to watch the sunset.) “Immediately, without even knowing if it was for sale, I knew I had to have Edgewater,” Jenrette says. “It must have been a true Shangri-La for a writer, with its 5 acres on the water and the Octagon Library designed by Alexander Jackson Davis in the 1850s, which Gore used as his study. Vidal wrote quite a bit about the house in his [1997] memoir Palimpsest, and in that era it did have a certain glamour: Truman Capote, Tennessee Williams and Jackie Kennedy would visit, and selling  Edgewater was an emotional decision for Vidal.”

After the closing in 1969, Vidal invited Jenrette to his apartment in New York for a drink. “While he took a phone call from his agent in Hollywood, I had a few vodka martinis with Shirley MacLaine, who happened to be visiting that afternoon and was absolutely delightful,” Jenrette recalls. Apart from his collection of homes, Jenrette also has plenty of more manageable possessions, from Duncan Phyfe furniture to Gilbert Stuart portraits, and concentrates his resources on early 19th-century American furniture, befitting the circumstance of most of his six houses being from that particular period. His first weekend retreat was all white columns and pure charm: the circa-1838 Roper House in Charleston, South Carolina, which he bought in 1968. Over time, he would also acquire Millford Plantation, about 45 miles southeast of Columbia, South Carolina, and built between the years 1839 to 1841 (he calls the property “my Taj Mahal” and the “finest Greek Revival house in the South”) and Cane Garden, an old sugarcane plantation in the Virgin Islands. Jenrette is an ardent preservationist, having earned such honors as the National Trust for Historic Preservation’s Crowninshield Award, but he remains intent on making preservation fun and accessible. Most of his residences, which are run through his foundation, Classical American Homes Preservation Trust, are available for public tours. He has also published a book on his various properties, Adventures with Old Houses (2000). “I collect villas, homes that are actually livable,” he says. “When a house is too overpowering, it’s also less interesting.”

Despite its northern location Edgewater has a gracious Old South flair, from the high ceilings to the raised portico—Jenrette thinks it may have been designed by Robert Mills of Charleston for its original owner, John R. Livingston, who gave the property to his daughter, Margaretta Livingston Brown. But it has one rather squalid feature, two railroad tracks within 75 feet of the rear courtyard door. (The advent of the railroad tracks in 1852, built through eminent domain, was a terrible blow to Brown, who lost her father and husband that same year. She sold the house to transplanted North Carolinian Robert Donaldson—who had built the nearby Hudson River estate Blithewood, now part of the Bard College campus— and disgustedly left America forever.) During World War II, the constant freight train traffic made the place distinctly unpalatable, but now, according to Jenrette, mostly passenger trains pass by and aren’t too objectionable.

The first thing Jenrette did was to improve the view—a high wall in the rear, overgrown with vines, hides the passing trains. He then purchased some 45 adjoining acres, both along the water and in the hills above the train tracks. He repaired the “rickety” front porch, added a fresh coat of paint, and then set to work on the  nuances—uncovering the deep red walls under layers of paint in the morning room and restoring the Duncan Phyfe sofa, custom-made in the 1820s; installing a carpet in the Octagon Library with a design copied from the notorious baths of ancient Pompeii; adding his trademark blue-onblue bedroom, a thematic thread useful for feeling at home when you travel constantly between six different houses.