Before Danroy “Dan” and Angella Henry purchased the house now known as Dragonfly at the corner of Canonicus and Seaview Avenues in Oak Bluffs, they had a summer home on Cape Cod. The “beauty, charm, and diversity of Martha’s Vineyard” eventually lured the family to cross the Sound and, along with their three children, DJ, Kyle, and Amber, the Henrys tried different rentals over several seasons. But after DJ, who was named for his father, tragically lost his life in New York in 2010 just shy of his twenty-first birthday, the peaceful pull of the Vineyard was even stronger. Following DJ’s death, the family looked for a permanent place to call their Island home.

Like many Vineyard house hunts, there were missed opportunities. The stars finally aligned in 2017 when they toured an open house for a waterfront property close to downtown Oak Bluffs. After the visit, Dan and Angella walked to Ocean Park to mull over the opportunity and challenge of committing to this particular house. They sat on a park bench – the bench that they had placed at the corner of Seaview by a lamppost and dedicated to their late son, DJ Henry. As Angella described it: “Suddenly, where we had sat many times, we were enveloped in a swarm of dragonflies – something we had never experienced.”

Dan and Angella recognized the urgent flutter of dragonfly wings swirling around DJ’s bench as “a clear sign that we had found our home.” And not just any home, but a visible cornerstone in the historic heart of Oak Bluffs.

It’s safe to say that no seaside corner captures the charm and energy of the town more than where Canonicus and Seaview Avenues meet. In many ways, it’s been the Island’s epicenter for summer gatherings since the turn of the century. In 1907 the neighborhood was home to the new Sea View Hotel, built after the original had burned down in 1892, and advertised in the summer address directory as “the finest located hotel on the Island situated among the most costly villas on Sea View Avenue and Waban Park.”

Since purchasing the house in 2017, the Henry family has greeted bikers and runners coming off the path and cordially acknowledged drivers backed up in bumper-to-bumper traffic past their front porch when both the Steamship and New Bedford ferries load at the Oak Bluffs terminal on August afternoons.

Appropriate for a home purchased with their own family in mind, the villa had survived generations of families and guests alighting on its verandas to watch the world go by. The Henrys loved the house for and despite its quirks, but also recognized that it was sorely tired and had endured more than a few alterations over the decades. In 2020, they began a meticulous restoration.

Because the home is located in two historic districts that encompass the area surrounding Ocean Park – the Copeland Plan District and Cottage City Historic District – the first steps for the restoration involved navigating review boards to meet their standards of cultural continuity and appropriateness. With the help of Joshua Gothard, whose Music Street Architects specializes in the restoration of historic homes, plans were drawn and meetings were set.

“Our first goal was to restore, reuse, and reconfigure the original cottage, which was lost in unfortunate updates during different eras,” said Gothard. “It was our intention to restore what the house had lost over the years, especially the ornate details typical of Oak Bluffs cottages at the turn of the century.”

The Cottage City Historic District Commission review gives weight to any surviving documentation, and the Henrys were able to present historic photographs of the original structure to back up their plans. “Most of all,” Gothard recalled of the meeting, “it was the Henrys’ mission and passion to honor the house and save the history that impressed the committees.”

Construction began in the fall of 2020, creating an interesting diversion for year-rounders who monitored the progress of the house while traveling the thoroughfare to Edgartown. “Be aware!” Dan remembered his Vineyard Home Improvements contractor telling him. “The whole Island is watching!”

And they were. The Henrys documented the progress of the renovation on their Instagram account, @dragonfly_house_mv, and as the house grew so did their Instagram following. In keeping with the name they had chosen for their home, they began adding dragonfly touches: gilded in the exterior porch eaves, carved into a custom table by Rafter Revivers, shining in stained glass, and spinning at the top of the tower wind vane.

From the start, the team on-site worked to thoughtfully rethink and reclaim the house’s original plan and craftsmanship. The foundation stones were among the first treasures to be unearthed in the digging of the home’s new base and were set aside for the landscaping phase. Today, they form the vertical anchors in the curved stone walls encircling the property. The next surprise was the reveal of fourteen additional inches of ceiling height in between perfectly preserved beams, which Dan, who is tall in stature, readily welcomed.

As with many houses of a certain age, at the time of purchase the first floor was a warren of five rooms, none of them really suitable for today’s lifestyle. The Henrys and their team developed a plan to open the space and make it more functional and inviting. Now a full first-floor living space is centered in the open kitchen, with contemporary elements that create a hospitable and breathable living space. Pigeon gray cabinetry with polished gold pulls are complemented by antique-inspired lighting in a weathered-bronze finish, details that seem to jump from the pages of a design book.

On summer mornings, the talking and laughter of the Polar Bears, the famous predominantly African American swimming club, waft into the sun-spilled kitchen where the Henrys savor their coffee and an unobstructed view to the east.

As they worked together, Gothard was continually impressed by how Dan “found inspiration and ideas even in the rotted beams of the original tower sill.” It was Dan’s idea to repurpose driftwood-hewn staves into a beach house design detail: the wood was used to inset a section of the staircase wall as a curio cabinet where visitors now contribute their beachcombing treasures. Elsewhere, a pair of original diamond pattern windows were sent to experts to be refurbished as colorful interior cabinet facings.

His creativity and ingenuity is also apparent in the design of the unique access to the basement, now a fully furnished living area. The proximity of neighbors would not allow for a typical raised metal entrance in the side yard, so Dan and his contractor partners constructed access through the floorboards of the front porch with pistons that lift the hatch and drop it back down to disappear into the porch floor.

But his most inspired creation may be the light fixture fashioned on a notched angled beam, wrapped with rope lights hung with seeded glass globes. Now the centerpiece of the newly expansive second floor landing, Dan described it as, “more than a conversation piece, but a piece of history!”

As part of the renovation, new history is being made at Dragonfly as visitors climb the reconfigured staircase to second-floor gathering spaces and the pinnacle of the project: an expanded tower previously only accessible by a ladder. Gothard gained the additional space for the third story from a “valley between two roof lines” to create the airy tower that now soars above Nantucket Sound, changing the horizon slightly for passengers arriving at the Oak Bluffs Steamship Authority dock.

New though the tower is, it’s designed to blend in with its surroundings. Dan added the interior detail of a repurposed beam marking the tower’s original elevation. He also found a New York artisan to mill and turn carved poplar balustrades for a banister that feels as if it has been grasped for a hundred years. Dan and Angella have a vision of their own grandchildren one day climbing their way to the top as “a perfect place for grandkids to build forts.”

While they anticipate the arrival of their own next generation, they are making a difference for a community of young people on the Island. Their DJ Henry Dream Fund is a nonprofit foundation that supports kids throughout Massachusetts and on the Island in partnership with the Martha’s Vineyard Boys & Girls Club. “Our mission on the Island is to provide [uniforms and free access], making it possible for a child to pursue a sport without the burden of the cost,” explained Angella. In 2021, a summer night of comedy at the Tabernacle in Oak Bluffs, with Seth Meyers and Amy Schumer donating their performances, launched the Boys & Girls Club collaboration. Angella is looking forward to doing more: “We want to have a greater impact on the Island we love.”

While the Dragonfly restoration was a labor of love to realize a dream of a family home, their appreciation for and commitment to the Island was strengthened during the process. Construction revealed original materials and clues to the history of the house, which the owners had only scant knowledge of when they made their purchase. But once their high-profile project began, history came knocking.

First it was information from Oak Bluffs historian and Martha’s Vineyard Camp Meeting Association president Andrew Patch, who produced a photograph of the house that shows summer revelers posing on high-wheeled bicycles and clear views across Waban Park (also known as Dennis P. Alley Park) to the peak of the Union Chapel – all of which predate 1900. The Henrys had previously ordered a wooden sign they displayed outside their home: “Built 1900: Restored 2021.” With the forensic information and more documents from Patch, the Henrys now date the house to 1874.

And, as it happens in Oak Bluffs, a woman stopped by the porch one summer day to share that her grandparents owned the house in the 1950s, which they operated as an inn, Eastman’s by the Sea. That woman, Dominique Milton, was sure that the home was listed in the Negro Motorist Green Book, which guided African American visitors to safe and hospitable accommodations while traveling. The historic Shearer Cottage in East Chop is cited as one such Green Book destination on Martha’s Vineyard. Milton’s memory spurred Dan to dig deeper, and he was able to find an Oak Bluffs property, “Eastman’s,” listed in the Green Book as early as 1954 with a P.O. Box that matched her grandparents’. When he confirmed this legacy to Milton, he said, “She had tears in her eyes, and I couldn’t believe our home was the only waterfront location in the book.”

Last summer, another property listed in the Green Book – Dunmere by the Sea, on Pennacook Avenue – was added to the African-American Heritage Trail of Martha’s Vineyard. The Henrys hope that someday their property may be added to the list of trail sites, which document formerly unrecognized contributions made by people of African descent to the history of the Island.

“We are continuing to learn the history; and it is coming to us across the threshold because we have honored the ancestors here. They are exposing to us all that energy and the gift of learning more,” said Dan.

In May 2022, after more than a year and a half of construction, the Dragonfly house was move-in ready, though there were still a few small projects that need to be completed. Following their first August in the refurbished house, Angella was delighted with the results and the lively dynamic at their corner of Oak Bluffs.

“We love people-watching from the porch,” she said. And while they are able to interact as much or as little as they want, the Henrys are undaunted by their special location, which can serve as a “bike repair shop, information center, and triage stop.”

Now, when the traffic slows, Islanders often shout congratulations and praise for the finished Dragonfly house project, which, Dan said with pride, some people “have begun to call ‘our house.’”