History Unfolds Inside Two Martha’s Vineyard Greek Revival Homes

Martha’s Vineyard, 2025: a desirable, discreet summer-home island for celebrities, politicos and affluent city dwellers escaping the concrete jungle. But in the 18th and 19th centuries, those celebrities were sea captains whose wealth and foresight developed a neighborhood that would become a particularly coveted island address.

What started with just a few houses along the harbor grew to include a Main Street and continued up the hill when Thomas Bradley, William Downs and William Daggett each bought large parcels of land in 1833. A new residential neighborhood took shape, and by 1858 it had swelled to 40 buildings, now known as the William Street Historic District. Originally known as Holmes Hole, the village named itself Vineyard Haven in 1871.

But the mid-19th century was a while ago and, as with any home, at some point renovations—for safety, comfort or aesthetic reasons—become essential. The historic homes in Vineyard Haven are no exception.

“The goal here is to repair rather than replace,” says Alexis Holden, realtor at Tea Lane Associates, who represents two special listings in Vineyard Haven—one on William Street itself, the other just around the corner on Spring Street. Most of these 56 buildings and residential homes were built in the Greek Revival style and are carefully preserved in this historic neighborhood.

Greek Revival Meets Quintessential New England

Built in 1880 and known as the Captain George Harding Home, 118 William Street is, says Holden, one of the area’s grander properties. Listed at $4,495,000, the address has had few owners considering its vintage. Most notable were the couple who bought it in 1941: Hamilton “Benzie” Benz, an organist, church choir director and director of the Vineyard Sinfonietta, and his wife Goodie Prior. “Benzie was quite a character on William Street,” says Holden. “He and Goodie used to host theater practices at their house, and they had two back-to-back pianos in their living room.

The story goes that the couple invited Leonard Bernstein and playwright Lillian Hellman, also a Vineyard Haven resident, over for a visit, where they composed part of the operetta Candide right at the house.” Clearly a case of “you can’t make this stuff up.” Other past Vineyard Haven residents of note include American novelist William Styron (Sophie’s Choice); the late director Mike Nichols and his wife, journalist Diane Sawyer; legendary newsman Walter Cronkite; musician Carly Simon; and the Obamas.

The present owners bought the William Street house in 2016 and chose to renovate in 2020, completing works in 2024. Honoring the home’s heritage, the refurbishment blends elements of modern luxury with historic charms and original features. Careful restoration followed William Street Historic District guidelines, including a rebuild of the wrap-around porch complete with spindle railing, wooden rocking chairs, crisp-white exterior paint and black-framed windows—all quintessential New England hallmarks. Inside, high ceilings, bay windows and a Carrara marble fireplace imported from Scotland command attention

Old, uneven floors were replaced with beautiful new fir flooring, says Holden, but the single-pane, two-over-two original bay windows to the front and sides of the house were kept—decisions that honored the integrity of the home’s grand old bones.

Architect Chuck Sullivan can be credited for handling this project with such care. “I live and work in Oak Bluffs but deal with the William Street Historic District on a regular basis,” he says. “There are a variety of architectural styles including Greek Revival, Victorian and Carpenter Gothic, and we typically source old photos of the neighborhood or the specific house we’re working on, bringing back as many original details as possible. The William Street Historic District is very thorough, detail-oriented, familiar with each and every property and very careful with their decision-making.”

Vineyard Haven’s first and only residential swimming pool was recently installed here, made private by lush green arborvitae, and welcoming with an outdoor kitchen and patio. A one-bedroom guest cottage with a kitchen and bathroom gives visitors a place to call home too.

Back in 1883, a devastating fire swept through Main Street, taking with it numerous buildings and homes, yet miraculously William Street was spared. “Perhaps that’s another reason why the homes on this street are so special,” says Holden.

The House That Jane Built

A classic East Coast-style home with shutters and a white picket fence, surrounded by hydrangeas and roses, is what many of us imagine when we dream of idyllic summer cottage living. Simple pleasures in a small seaside town where you can stroll up the street for ice cream. Or sit out on your porch on a warm starry evening with the sound of crickets gently hinting that another perfect day has come to a close. A lovely home on 27 Spring Street, also within the William Street Historic District, was built in 1842 and has its own interesting backstory.

On the market for $3,195,000, the property was built by Jane Smith Luce, the great-great granddaughter of Isaac Chase, a prominent businessman in Holmes Hole. Jane’s great-grandmother and grandmother both ran their own businesses as tavern owners and passed on their sense of independence as women to Jane who chose to reject the title of ‘widow’ when her husband died, adopting ‘trader’ instead.

Jane built this home in 1842 for her adult son Jirah and his young family, and according to Holden, was “quite the formidable lady of her time, choosing a grand-scale house with many large windows—a sign of wealth in those days.”

Today the home has five bedrooms, four full bathrooms and five fireplaces, plus the original winding staircase in the heart of the home. A mudroom, laundry room, central heating and air conditioning, plus a screened porch add modern comforts.

The present owner, architect Stephen Vanze, chose kitchen upgrades in keeping with the home’s traditional character. And in other rooms, painted black floors. Why black? “Most of the floors were like that when I bought the house so there was no going back,” Vanze says. “I suspect they were painted to hide the patina that they had already acquired.”

Vineyard Haven: A Creative And Community Hub

The town of Vineyard Haven is a perennially sought-after summer destination for “writers, the theatrical community, artists and composers,” says Holden, and one doesn’t need to spend much time immersed here to experience that welcoming creative vibe. The common hub both properties share is of course, Main Street, just one block from each address. Expect a charming mix of local independent shops, restaurants that champion local seafood, plus the Martha’s Vineyard Playhouse.

Martha’s Vineyard Museum, located just off Main Street, is in the old marine hospital, offering a depth of knowledge about the whaling industry’s history, and, until September 7, 2025, the exhibition Jaws at 50: A Deeper Dive celebrates 50 years since the classic Steven Spielberg film was released. Martha’s Vineyard was a key location for the production, and Vineyard Haven became the fictional beach town known as Amity on screen.

Amenities, walking path and easy proximity to the ocean are important in coastal cottage living. The Vineyard Haven Ferry sails year-round from Woods Hole on the southwestern tip of Cape Cod, and crosses Vineyard Sound in just 45 minutes. “This ferry does allow vehicles, but even better, your guests who arrive as foot passengers can walk from the ferry right to your home.”

Alexis Holden holds the listings for 118 William Street and 27 Spring Street. Tea Lane Associates is a member of Forbes Global Properties, the invitation-only network of top-tier brokerages worldwide and the exclusive real-estate partner of Forbes.