The first time Eileen Guggenheim walked through the doors of the 12th-century Tuscan farmhouse that would become her dream home, the atmosphere didn't exactly suggest a domestic idyll. "Animals used to live on the first floor," recalls Guggenheim, chairwoman of the New York Academy of Art's Board of Trustees. "It was all dirt, and there were troughs in the living room."

But the podere did have great bones, epic views of the surrounding countryside, and endless acres of unkempt gardens that were begging to be resuscitated. So Guggenheim and her husband, retired gallerist Russell Wilkinson—who first fell for the velvety green spoils of Tuscany while visiting the nearby home of artist friends Sheppard Craige and Frances Lansing—decided to snap it up. Together they spent three and a half years faithfully restoring the property, and now divide their time between the horn-honking metropolis of New York City and this meditative paradise on the outskirts of an ancient hill town. "Russell always says that this is really his home," Guggenheim explains. "I feel the same way. You really appreciate the little things, knowing people. It's a sweet life."

Although the house was in clear need of an overhaul, its barnlike origins gave it a sense of depth and rustic character. Guggenheim chose to keep the charming original open-lattice brickwork in the master bedroom—once a hayloft—but rebuild many of the stone walls and brick arches. Old wooden ceiling beams were sourced from neighboring farmhouses, slabs of marble were cut from local quarries, and quaint painted furniture was acquired in nearby towns—"the kind you would have found in a Tuscan house 100 years ago," she says. Terra-cotta-painted rooms now serve as backdrops for vibrant embroidered tapestries, rugs by Jules Leleu, and the couple's collection of Italian pottery, which includes everything from pieces that Marcello Fantoni created for Raymor in the 1960s to a gold-and-white luster vase by Ulisse Cantagalli, considered the Louis Comfort Tiffany of Italy. "I tried to respect the house," Guggenheim says. "Around here you don't really decorate."

Outside the jasmine-covered main house, an emerald swimming pool shimmers at the top of a silky lawn. Rosebushes border the hedges of a formal garden, while manicured shrubbery mingles with century-old olive trees, giant clay vases, and stone pozzo wells. The lush surrounding landscape, which is dominated by wild tufts of rosemary and lavender that fall off into a field of orange poppies, was planned by Wilkinson—and inspired, in part, by the verdant grounds at Prince Charles's country home, Highgrove, where the couple have stayed as guests. (Guggenheim spent four years working at one of the prince's charitable organizations, the Prince's Foundation.) "He found an amazing black tulip to plant," Wilkinson remarks of the prince's horticultural endeavors. "He's obsessed with it, and seeing his passion has had an effect on us."

The land had its challenges: More than a hundred dead trees had to be cut down, overgrown areas were in dramatic need of scaling back, and all the grass had to be reseeded. "Eileen and I made a pact when we first got into this, and it probably saved our marriage," Wilkinson recalls. "There was a dividing line—she would handle everything inside, and I would handle everything outside. Neither of us really knew what we were doing, but it worked." Blooming begonias now fill moss-green urns that border wrought-iron gates, while a loggia with exposed cross beams has been transformed into a garden shed where Wilkinson stores watering cans, shovels and spades, copper pots, and woven flower baskets.

Guggenheim's love affair with Tuscany first took root when she was an undergraduate and spending summers volunteering at an orphanage in Florence. But her decision to work in the arts drew her back home.She received her Ph.D. in art history from Princeton, and went on to teach at the University of California, Santa Barbara, then Princeton, and finally at the New York Academy of Art, a small private graduate school in Manhattan's TriBeCa neighborhood that was cofounded by Andy Warhol in 1982. (A fellow art lover, Wilkinson once headed the board before Guggenheim was appointed its chairwoman in 2008.)

"With a last name like Guggenheim, how can you not be an art historian?" she says lightly, referring to America's preeminent art patrons, to whom she is distantly related. In her 30-year run at the academy, where she's wrangled artists including John Currin, Rachel Feinstein, Eric Fischl, and Jenny Saville as guest lecturers, she has championed young artists as well as a return to the forgotten techniques of the Old Masters. "The idea behind the school is the preservation of traditional painting, drawing, and sculpting," Guggenheim explains, noting the rise of digital and video-based art. "At art fairs now, you see these monolithic conceptual installations but rarely the hand of the artist. If you come to our place, you end up drawing like Raphael."

"Her passion and energy have really helped build the institution into the go-to place to establish emerging artists," says friend Naomi Watts, who, with partner Liev Schreiber, has supported the school for almost a decade. Chief among Guggenheim's achievements at the academy has been her masterminding of the Tribeca Ball, an open-studio party held on the school grounds; and the Take Home a Nude auction at Sotheby's. The two events not only help keep the academy funded but also have become highlights of the New York social calendar, drawing guests like Jeff Koons, Jason Wu, and Mary-Kate Olsen. "We go to lots of these kinds of events," adds Watts, "but what I love about [the ball] is that you always end up sitting next to someone you really want to talk to."

Not surprisingly, Guggenheim's art-world life spills over into Tuscany: Throughout the house one stumbles across unpretentious pockets of Post-Impressionist and contemporary art—be it an interiors scene by the French artist Blanche Camus, Frances Lansing's encaustic paintings, or a striking canvas of a giant cow's head by Maggie Rose. Many pieces are by students at the academy, and they coexist comfortably with turquoise-painted Tuscan chests, 17th-century walnut tables, and carved bird lamps found in junk shops. The house is kept up with the help of Guggenheim's "very own super Tuscans"—a hunky gardener who oversees the sprawling vegetable and herb garden, and a chef who is called in for special dinners with friends like interior designer Steven Gambrel, photographer Sally Gall, and painter Stephen Hannock, along with an international mix of artists, writers, and musicians who live nearby.

The couple's life in Italy is languid and meant to be savored, like a swirl of Brunello di Montalcino in the mouth. But it's far from sedate—a competitive triathlete, Guggenheim wakes up early and bikes 35 miles, swims laps in the pool, or runs. Most afternoons she can be found reading, exploring neighboring towns, or spending time with her daughter, Isabel Wilkinson, the fashion and arts editor at The Daily Beast, who pops in whenever she can. (Conveniently, a Brunello Cucinelli outlet is nearby; Guggenheim also makes sure to stock up on breezy resort pieces from Valentino, Lanvin, Bottega Veneta, Prada, and J. Crew.)

But as this region was the cradle of the Renaissance, it's the cultural jewels that have captured Guggenheim's interest and imagination the most. "There's always some amazing little museum or a church full of frescoes," she says blissfully. "All I have to do is come here, and then I realize that what we're doing at the academy is highly relevant."

CLICK THROUGH TO SEE PHOTOS FROM EILEEN GUGGENHEIM'S ITALIAN FARMHOUSE.

Pictured above: Guggenheim on the threshold of her Italian retreat. J. Mendel dress, $3,250, jmendel.com. Christian Louboutin shoes, $625. Similar styles available at Christian Louboutin, NYC; 212-255-1910. Fashion editor: Joanna Hillman