A Few of His Favorite Things

Jim Ferraro’s “top ten” list for his Vineyard Haven estate offers a glimpse inside one of the Island’s more expansive and elaborate properties.

During the summer of 1976, twenty-year-old University of Miami undergraduate Jim Ferraro and a friend hired on to move an acquaintance’s belongings to Martha’s Vineyard. With no room reservations to be found, they ended up sleeping in the back of their truck in the parking lot by the Gay Head Light.

Contrast that humble introduction to the Vineyard with where Jim is today. A successful trial attorney, he has transformed a two-and-a-half-acre site on Vineyard Haven’s Main Street into his own 21,000-square-foot private family resort. His West Chop property overlooks Nantucket Sound and a wildflower-filled waterfront meadow he calls “the crown jewel of the Sheriff’s Meadow Foundation,” the conservation group that owns the open field.

Back in 2003, Jim was jogging on West Chop when he noticed a small “For Sale” sign in front of a world-weary home set above Main Street with sweeping views of the outer harbor. Although he already owned a home on Hines Point in Vineyard Haven, he engaged in a bidding war for the property against another potential buyer and emerged the new owner. “I’d always admired the view,” he says today, standing on the deck of his now-completed compound.

With forty-five relatives descending for an annual one-week summer reunion, Jim is utilizing nearly every inch of his property’s fourteen bedrooms and twenty bathrooms. In addition to his mother and ninety-nine-year-old grandmother, a nervous chihuahua, two Pomeranians, and a Maltese, there’s a mélange of cousins, aunts, uncles, children, and staff, who appear to be enthusiastically engaged in a variety of activities throughout the property.

Relaxed and casual in khaki shorts, a golf shirt, and a baseball cap, Jim is a congenial host, stopping to greet newly arriving guests and fielding calls from his son and architect, all the while pointing out many of the compound’s noteworthy features: two gyms, a large outdoor pool, a tastefully tucked-away tennis court, nine- hole putting green, bocce court, and a garden with an overflow of fresh herbs he has shared with the popular Oak Bluffs Italian restaurant Jimmy Seas for its garlic-laden dishes.

And while there’s no denying that Jim was thorough in his quest to create a first-class retreat from the fracas of a demanding legal career, he also worked earnestly to screen the property’s three additional structures and abundant amenities from the road. The main house dominates the view, with building placement, landscaping, a stone wall, and a large gate carefully planned to minimize the visual impact. “As big as it is,” he says, “it doesn’t seem overbearing.”

His primary goal, he asserts, was to create a property where his three children – twenty-five-year-old James, twenty-one-year-old Andrew, and eighteen-year-old Alexis – can come with their children and their children’s children. “I wanted to build something they can all share and use anytime, with enough room for everyone. It’s a family asset.” He now uses the estate as his summer base but intends to stretch his season to five or six months in coming years. He also enjoys hosting holidays on the Island. “I love it here,” he says. “The Vineyard is a place that values family time and that’s very important to me.”

Although it was tough to whittle it down to a short list, these might well be his ten favorite features at the Ferraro compound.

Jim’s Top Ten List

1. Widow’s walk. Perched high atop the main house at chimney level, it’s outfitted with chairs and serves as Jim’s quiet escape. “I come up here when I don’t want to be found,” he admits.

2. An abundance of wood. Jim hired Vineyard contractor Gary Maynard of Holmes Hole Builders because of his many years of custom boatbuilding experience. Intricate inlaid foyer floors, the great room’s soaring ceiling, woven-wood railings, and graceful curved stairways are woodworking showcases for Gary’s crew and subcontractors.

3. Putting green. An avid golfer with an eight handicap, Jim plays a round at least three times a week at the Vineyard Golf Club in Edgartown. His own putting green with water views helps keep his short game tuned up.

4. Office. Spacious and light-filled with dramatic views, Jim’s office is paneled in sycamore. It features a nook with a round conference table and swivel chairs, video conferencing capabilities, and personal collectibles. With offices in Miami, New York City, Washington, D.C., and Cleveland, Jim specializes in mass tort litigation and won a landmark suit that was the first case successfully prosecuted against a chemical company for causing a birth defect; now his two firms represent nearly fifty thousand asbestos claimants. On-Island, he often plays host to business associates who, following comfortable sessions in the office and adjoining library, can hit the links or relax around the estate.

5. Sports bar. Although Jim insists the lower level in the main house is a magnet for his children and their friends, it’s hard to imagine a “man cave” better suited to meet the stereotypical American man’s needs with its bar, multiple flat-screen televisions, movie theater, pool and roulette tables, fireplace, comfortable sofas and lounge chairs, poker table, and adjacent fully stocked wine cellar.

6. Library. Designed as a retreat for his late father, the library is adjacent to Jim’s office. “He died before he had a chance to use it,” Jim says, “but my father would have loved this room.” With its earthy, soothing palette and bookshelf-lined walls, the library now serves as a quiet retreat for visiting business colleagues and as a gentle reminder of the close relationship Jim shared with his dad. “He inspired the three rules I live by,” Jim says. “Have fun. Don’t hurt anyone. And in the scorecard of your life, how many people did you help along the way?”

7. Gyms. Yes, that’s two gyms: one in the guest house for weight training and another in the pool house for cardio. A fitness buff (along with his children), Jim hits the gyms almost every day, and adds biking, running, and golfing to his list of healthy pursuits.

8. Sports memorabilia. It’s everywhere – in his office, throughout the guest house, and, most of all, in the main house’s lower-level sports bar. Jim’s collections include framed boxing shorts, football helmets, baseball bats, and photographs that tell the story of American professional sports during the last several decades. He enjoys his collection so much that he spent more than a year hanging each item himself with the help of an assistant. Jim’s a former Greenwich (Connecticut) High School and University of Miami Hurricanes football player and current majority owner of the Cleveland Gladiators franchise of the Arena Football League.

9. Master bedroom. Photos of his children adorn the walls and, during the day, the adjoining nook and outdoor deck are nothing short of spectacular for views of the water and picturesque boats. Jim says, “At the end of the day, late at night, it’s my favorite place to relax.”

10. Family dining room. It’s the stage for the annual Ferraro Thanksgiving dinner and the July family reunion, and comfortably seats twenty-two for the main reunion meal (with additional dining tables in nearby rooms to accommodate the overflow). With its coffered ceiling and unique inset fireplace with cozy built-in benches, the room offers the kind of warm gathering place Jim considers a main priority.