Some people enjoy window-shopping, but I have always been drawn to imagining what the interiors of people’s homes look like when passing by outside. So I was thrilled to get a sneak peek inside three of the six residences on the Edgartown Historic Home Tour. The special one-day event, on Monday, August 18, from 10 am to 2 pm, is part of the Vineyard Preservation Trust’s 50th anniversary celebration.
The tour encompasses six remarkable homes and architectural landmarks, each reflecting a distinct aspect of Edgartown’s architectural legacy, from 17th century craftsmanship to contemporary design. “Our first-ever private home tour is a love letter to Edgartown,” says Nevette Previd, executive director of the trust. “Each home reveals a layer of the Island’s story, from its colonial roots to contemporary reinvention. It’s a beautiful reminder of how we preserve, inhabit, and honor the past while living fully in the present.”
Photographer Dena Porter and I first stopped at the Pineapple House, with its stunning 200-year-old linden tree in front. Victor and Jackie Zollo welcomed us into one of the town’s oldest homes. We entered from the South Water Street side, which wasn’t originally there, since everything was oriented toward the water. The house was built in 1682 for blacksmith John Coffin by his father, Tristram, one of Nantucket’s earliest European settlers. It measures 24 feet wide by 32 feet deep, and has two stories, plus a basement at the front and one story at the back. Looking around at his home, Victor commented, “You see by the smallness of the room sizes and flow, it’s not today’s world.”
The interior is cozy, covered with cherry-wood paneling. Everywhere you turn, there are wonderful fireplaces, five of the nine being original. Outside, there is a lovely copper-roofed bay window believed to be more than 200 years old. “We first lived in the house for about 10 years before doing any work, to get a sense of it,” said Jackie. Over the course of three and a half years, the Zollos restored many of the home’s 1800s features using historical photographs.
The family gathers in the formal dining room for the holidays, grandchildren play in the sunroom turned playroom, and art by Ray Ellis — a close friend — graces the walls. A favorite space is the pub in the basement, which, with its rich, large wooden furniture set against exposed stone walls and beamed ceilings, looks like you have stepped back many centuries to Edgartown’s colonial past. “The basement was a dark, scary place when we bought it, with dirt floors,” Jackie explained. “When we started the renovation, the foundation crumbled, so we decided to turn it into a pub, and added a wine cellar.”
Asked if they had any favorite quirks of living in such an old abode, Victor replied, “We know one of the owners was a cobbler, and we found several things in the walls, including a small child’s boot. It was in the wall, probably 300 years old, and we kept it.”
Our second stop was the Conway House, located on North Water. Its light-filled interiors celebrate the harbor view with boundless maritime artwork, including one by Island artist Francisco Rapoza, in which, with careful looking, you can spot a horse swimming in the waves beside a whaling boat. The summer sun shining on the broad wood floors and historic beams enhances the home’s welcoming warmth. As I was walking in, a mural by Twanette Tharp along the stairs leading up to the second floor immediately caught my eye: beach views, the Flying Horses, and the Fourth of July Parade, representing the Conways’children’s favorite summer pastimes.
Kim and Drew Conway bought the house in 1998. They preserved much of the historic home, including a dumbwaiter that Drew uses to haul luggage upstairs when guests visit. Although its origins are uncertain (somewhere between 1753 and 1793), the fact that it’s haunted enhances the feeling that it’s been around for centuries. “The ghost, though, is a servant,” said Kim, because she seems to be on the fourth floor, which was once the servants’ quarters. Drew added, “When Kim and I are here alone, you can hear her walking across the floor right above our bedroom at night. I would go upstairs many times, and there would be nobody.” There’s more to the story, including a possible murder mystery, but you’ll have to ask the couple themselves for details.
Looking out over the water view with a dock, Drew explained, “This is one of the five wharves of Edgartown. The tax collector lived here, and the boats coming in would have to stop, and [he would] assess them.” As you gaze out, you can see the nearby guest cottage, lovingly modified to accommodate the next generation, including a “mermaid room” for granddaughters. The Conways call it “the boathouse,” because there are still tracks coming into it, and a winch where they used to bring the boat in.
Our final stop was something entirely different, on Davis Lane. Cristina Aragona and Gregg Jubin bought the former Davis Academy in 2017. They transformed what was once the site of an 1830s co-ed school and later a lecture hall –– hosting orators like Frederick Douglass –– into a contemporary masterpiece. Straight ahead when you walk in is a large orange fiberglass-and-resin Jackson Pollock–style decorated head by Ancizar Marin, placed near the base of an enormous bright yellow spiral staircase, which is reminiscent of what you might see in a lighthouse. Dramatic features such as a rotatable fireplace, checkered floors, and striking installations by artists Lucy Dahl and Steve Lohman add vibrancy to the space. “Ninety percent of the art is local,” Cristina informed us.
Nestled within the modern aesthetic are original elements, including hand-hewn floors, beehive oven bricks in the basement, vintage sinks, a footed bathtub, and exposed granite and timber beams. “When we bought it, it had to be completely gutted, because it was falling apart,” Cristina explained. “It didn’t have air conditioning. It had one bathroom. You had to unplug a light to put a hairdryer in. But it was charming and always full of light. We loved it.”
Upstairs, the four bedrooms wrap neatly around the staircase. But the basement, once forgotten, is now a destination: “It wasn’t a usable space. It had a dirt floor, a crumbling beehive oven, and beautiful granite walls that weren’t celebrated. We dug away, exposed the stones, and shored them up.” The couple has transformed the area into a fabulous, casual space, showcasing more eclectic art.
The tour will also include the Maloof House, the Charlotte Inn, and the O’Hare House. Docents will be stationed at each site, providing historical context and restoration insights. Visitors will receive a commemorative booklet, a walking map, and access to gardens and grounds throughout Edgartown.
Starting from the Carnegie Heritage Center, 58 North Water St. For tickets, visit bit.ly/Auctria_EdgartownHomesTour.
