Long before Ronald and Judith Davenport owned their gorgeous Oak Bluffs home, they used to sometimes sneak onto its dock from their nearby East Chop rental for a glass of wine at sunset, or onto its beach in search of sea glass. The couple, who first met as students at Pennsylvania State University and moved to Pittsburgh to raise their three children, came to the Vineyard for the first time in 1975 to visit a friend and fell in love with the Island immediately. They rented the same house on East Chop for ten summers and then found another one in Harthaven that they rented for ten more.

Ron is a Yale-educated lawyer who served on the President’s Commission on White House Fellowships in 1993. Judy, who had a dental practice in Pittsburgh for many years, was appointed in 2014 by President Barack Obama to the board of directors of the Corporation for Public Broadcasting. She was an obvious choice: together with their children, the Davenports own the Sheridan Broadcasting Corporation, one of the largest African American–owned broadcasting companies in the country. But though both Ron and Judy were financially successful, they had no real interest in owning property on the Island, until their beloved rental in Harthaven fell through in 1996 on what felt to them like short notice.

Nearly twenty years later there is just a hint of irritation in Judy’s voice when she talks about that broken lease. “We didn’t like this being jacked around,” she said. But from their current vantage point – the sunny enclosed porch of a sprawling waterfront home that they call their own – it’s clear that the lost rental and the resulting decision to look to purchase was more of an opportunity for the Davenports than a setback.

When they heard that the property they used to visit on the sly was for sale, Judy sent their friend and caretaker Everett Whorton to check it out. “Everett was someone I knew we could trust,” said Judy. He called her that very night. “Judy,” he said, “You have to do this.”

One of the former owners was an African American dentist like Judy, which struck her as a fortuitous sign. More important was the fact that, though the house was in “a horrible state of affairs” and the owners were anxious to sell, the Davenports saw its great potential. They bought the old house in the spring of 1997 and spent the next few years designing and building their dream home, which, at nearly 6,000 square feet, includes four bedrooms and seven bathrooms.

Over the almost twenty years that they have owned the place, the Davenports have hosted a number of high-profile events at the home, ranging from their youngest daughter Susan’s wedding with more than 200 guests, to fundraisers for then–presidential candidate Obama. Yet when they first met with various architects to talk about their new purchase, they earnestly described themselves as informal. Eventually they narrowed the field of potential architects to two, whom they referred to privately as French’s mustard and Grey Poupon.

“French’s wore blue jeans and was more into building our home rather than designing a house for his portfolio,” Judy said. They chose Joseph W. Dick, a.k.a. French’s. “He got our lifestyle.”

Dick, who has offices in Yarmouthport and Vineyard Haven, asked the Davenports a series of questions, such as “Are you readers?” (Yes.) “TV watchers?” (No.) “Do you entertain a lot?” (Yes.) “Are you boaters?” (No.) Like many Victorian-era homes, this one – built in 1870, per assessors records – had an inward focus. The Davenports didn’t want to tear down the house, but rather open it up to create a brighter, more family-friendly atmosphere. With that information in mind, Dick went to the drawing board and came back with a design so in sync with the Davenports that aside from switching the dining room and library, the house matches the original drawings exactly. With additional help from interior designer Gil Walsh, of Palm Beach, Pittsburgh, and Edgartown, the finished product is an airy beach house that manages to seamlessly showcase remnants of the dark oak, wood-paneled formal house that it used to be.

The first floor features two porches. Toward the rear of the house, facing the rambling lawn and Nantucket Sound, is where Ron and Judy have an end-of-the-day gin and tonic with friends. On the “street porch,” which faces the busy Temahigan Avenue (though you wouldn’t know it), Judy likes to have breakfast and read the newspaper in the morning light. An accomplished cook, she takes special pride in the kitchen. She wanted to be able to socialize while working. “I didn’t want to cook in a vacuum,” she said, so the room is big enough for helpers or observers, and it looks out to the water porch.

In the basement is a hot tub, sauna, exercise room, and wine cellar, which is noticeably sparse. “We like to drink our wine,” said Judy with mock embarrassment and a wave of her hand. But the main event in the basement is the playroom, stocked with all the fixings for a magical childhood summer: bikes, beach toys, a Ping-Pong table, air hockey, and even an old-
fashioned popcorn machine.

Each of the Davenport children has a bedroom that they consider their own, and that is how Judy describes the rooms: “Susan’s room,” “Ron’s room,” and “Alison’s room.” In the master suite, which Ron and Judy use as a bedroom and office, they kept some of the house’s original furnishings, including bureaus and doorknobs. Last but not least, there is plenty of room for their five grandchildren in the large, open dormitory-style room on the third floor overlooking Vineyard Haven harbor.

All of the doors and many of the windows are original, and the Davenports decided to keep the old brick fireplace in the main sitting room. As she walks through each of the four bedrooms, Judy adjusts paintings and smooths sheets. “I know I’m nuts, but I have to,” she said with a laugh.

The Davenports’ international art collection is a tribute to the places they’ve traveled during their fifty-three-year marriage: the Bahamas, South Africa, Vietnam, China, and Zimbabwe, to name a few. “It’s an eclectic mix of contemporary art from all over the world,” said Judy in an attempt to summarize the works.

Since they officially moved into the house in 2001, Ron and Judy have done very little in the way of renovating, decorating, or even rearranging – a testament to how well the job was done the first time. When they arrive on-Island in June, they settle in with very few disruptions until early September. “The mail gets forwarded and that’s it! We’re here!” said Ron.

“It’s done,” Judy said of the house. “We just live in it now.” With that she pauses to adjust a painting just slightly, gives it a barely discernible smile, and continues on.