Tucked into the woods off Lambert’s Cove Road, where tree branches weave a canopy over a mossy lawn, a cedar shingled house rests beside a wetland pond. Its entryway is triangular and framed by two tree trunks where rain sometimes drips from the sides. Carved into the shingles above is a silhouette of a wizard with a long beard. He holds a wand, poised to cast a spell. 
      
Donna DiFillippo and Michael Ruttner call their home the Shire, a nod to J.R.R. Tolkien’s book The Hobbit. The couple is retired: DiFillippo is the former executive director of an early literacy nonprofit called Raising a Reader Massachusetts, and Ruttner helped run a work-clothing company called UniFirst. They have three kids, Carly, Julia, and Ben, and four grandchildren, Isabel, Harper, Luca, and Beaux. The family had visited the Island for many summers and wanted to find a home just as whimsical as their story-filled memories. But what mattered most when looking for a home was that it had to be big enough to keep their family together for years to come. 

DiFillippo and Ruttner were already anchored to the Island from their summer stays. In the early days, the family would rent at The Duck Inn in Aquinnah, eating breakfast by the cliffs in the morning, walking to Philbin Beach or driving to Menemsha for ice cream during the day, and lighting lanterns at night. They were enchanted by and bonded to their Island routine and wanted a permanent home up-Island, where the secluded woods and water could be the playground their grandchildren grew up exploring.   

When the couple saw the Shire for the first time, they were surprised the same remote, woodsy feel could be found in the down-Island town of Vineyard Haven. They soon discovered that many of the homes off the Vineyard Haven end of Lambert’s Cove Road offer a secluded up-Island feel, as well as the benefit of proximity to grocery stores and nightlife.   

The house itself felt magical. The previous owners had installed wooden door handles and stair railings whittled to depict faces or to look like owls and fish. A stone fireplace in the primary bedroom featured a heart-shaped stone at the center. Even the mossy lawn served as a carpet for outdoor games. DiFillippo and Ruttner pictured their grandkids peering out of little circular windows located beside lofted bed frames.  

“This house had all these handmade touches that made it feel like home,” DiFillippo said.  

They purchased the house in 2018. What sealed the deal was the layout of the property, which resembles a quaint campus. The main house, where DiFillippo and Ruttner live, sits at the heart of it, with winding paths that extend to two smaller cabins and a barn where their children stay with their families. Each building feels both connected and independent, giving everyone space while keeping the family close.  

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Since purchasing the Shire, the couple has undertaken a series of thoughtful renovations, carefully updating the spaces to fit their multigenerational needs and yet preserving the handcrafted charm of the home. That charm dates to the 1960s, when the home was artfully constructed by Bernie Fierro. His wife, Lee Fierro, was a local theater teacher and actor who had a prominent role in Jaws. 

The main house was Bernie and Lee’s carpentry project and has many handcrafted elements, such as cabinets and statement windows. A door to the kitchen has panels made up of different sized trapezoids fitted together like a puzzle. Large glass windows illuminate the living room, which has an A-frame roof line. 

Adjacent to the main house is a barn built by the Fierros in the 1970s to give them more space. It has large sliding doors that open to a living room. DiFillippo and Ruttner’s grandchildren’s play sets are now strewn throughout the floor, evidence that the barn has become the main indoor gathering place for the couple’s grandkids. The room is furnished with sofas and chairs large enough for a guest to sleep on, and is decorated with vintage baseball memorabilia and Martha’s Vineyard Agricultural Fair posters. The couple added a kitchen for their family to prepare meals, which are eaten on a long dining table with bench seating. It also has a bedroom with a daybed next to a window.  

“This is really, basically, the hangout,” Ruttner said.  

There are also two smaller cabins on the property for the family to stay in. The more secluded one, called the writer’s cabin, was built for Lee, who was writing a play at the time. To get to the cabin, the family walks down a moss-covered staircase that’s lit at night by outdoor fairy lights strung beside it. Bamboo obscures the staircase from the neighborhood road. In the spring, the fairytale-like path is in bloom with daffodils.  

Originally, the cabin didn’t have any plumbing. When DiFillippo and Ruttner bought the property, the bathroom included a composting toilet that didn’t work and an outdoor shower that had seen better days. They worked with the town’s building inspector to install a standard toilet that was up to code and updated the outdoor shower. With the additions, the writer’s cabin now functions as its own self-contained unit. It’s perfect for their son, Ben, a musician who often stays up late working on songs with friends.  

The other cabin is positioned on a hill overlooking the property. It has the same interior as the rest of the buildings: wood-paneled walls painted white. Its one bedroom is just big enough for a queen-size bed, and a door that opens to a porch with a table. Each of the cabins has its own refrigerator but no kitchen, so guests use the kitchen inside the barn for most of their cooking. DiFillippo and Ruttner transformed a former potting room in the cabin into a bathroom, complete with a washer and dryer. The cabin sits in front of a swimming pool that, on this particular day, the family was enjoying.

“How’s your belly?” DiFillippo asked her granddaughter Harper, who had just taken a belly flop.  

“It feels great,” Harper said with a mischievous grin after she surfaced.  

The pool is not the only place fit for play at the Shire. Tucked among the trees, the family created what they call the woodshed, a magical space that looks like a fairy house brought to human scale. Its sloped wooden walls form a cozy tent-like structure, held up by sturdy branches as if it had just fallen out of a tree. Inside, the woodshed is filled with playthings, such as a leather boxing bag, a miniature dollhouse, and wind chimes that dance when a breeze comes through. Rocking chairs are where the grandchildren imagine pirate adventures and daring quests.  

DiFillippo and Ruttner said they learned a great deal while renovating the Shire to suit the needs of their extended family. Their main piece of advice for anyone looking to purchase and restore a home on the Island was to cultivate strong relationships with the caretakers and rely on trusted contractors. Their house is so unique that only the caretaker could answer certain questions about its original construction, and the Vineyard is so small that, once you find a reliable contractor, it’s wise to hold onto them. 

The family has no plans to ever sell the Shire. They hope it will be passed down to their children, then their grandchildren, through future generations. DiFillippo reflects on the ski home her parents purchased in Maine, where she and her siblings brought their kids, who got to know their cousins well. She cherishes those memories and sees that same sense of rootedness in her grandchildren. Watching them play together outdoors, she can hear their laughter mingling with the rustle of leaves. 

She and Ruttner smiled, knowing the house has given their family the space not just to grow close, but to explore and create memories in a setting that feels as magical as they felt coming to the Vineyard the first time. 

THE TEAM

Builder: Bernie Fierro
Interior Design: Catherine Finch
Masonry: Contemporary Landscapes
Renovation General Contractor: Blair Emin
Swimming Pool Contractor: Island Pools
Barn Flooring: Vermont Hardwoods