Donna DiFillippo and Michael Ruttner spent years vacationing on the Vineyard before deciding in 2018 that they wanted a home of their own. Their search led them to a secluded Vineyard Haven compound that included a main house, a renovated barn, and two small cottages set beside a pond. It brimmed with whimsical, handcrafted details. Even better, it offered plenty of space for their adult children and grandchildren to spread out and still gather close. They purchased the home and named it The Shire, a nod to the magic conjured by J.R.R. Tolkien. 

Over the years, the family undertook a series of thoughtful renovations. They replaced flooring, improved plumbing in the outbuildings, added a pool, and built an enchanting, fairytale-like woodshed tucked among the trees. They layered each room with art, memorabilia, and carefully curated upscale furniture. The results, featured on page 40 of this issue, speak for themselves. And yet the most extraordinary thing about DiFillippo and Ruttnerʼs home isnʼt the floorboards or furniture; itʼs the warmth that radiates within its walls. For them, a house is more than a series of design decisions; itʼs a place that gathers the people they love. 

The same spirit lives in the home of Nate and Lauren Morgan, featured on page 30. They designed and built a structure wrapped almost entirely in glass so that their children could watch the seasons change. In Oak Bluffs, Melonie Parker’s bungalow (page 60) already has become a compass point for her family. Her grandkids have memorized the walking route to the beach, Parker said proudly – a ritual that will anchor summers for years to come. 

Each of the properties in this issue highlights different styles, settings, architects, and artisans, yet they share a common bond. They open their doors wide, inviting family and friends to settle in, slow down, and pull up a chair. In doing so, they remind us of the quiet magic of an Island home.