SHOWCASING THE WORLD’S FINEST PROPERTIES AND THE STORIES BEHIND THEM

The placid waters of Menemsha Pond eventually find their way to the open horizons of the Vineyard Sound, both sublime settings for sailing. (Tea Lane Associates)

Best-loved spot on Martha’s Vineyard? No-frills Menemsha

In one small village on Martha’s Vineyard, nature gets a standing ovation.

Menemsha, on the western end of the Massachusetts island, commands a faithful audience of devotees who rush to the town beach, roll out blankets, uncork wine bottles and await the big show. 

“Sunset is nearly always an explosion of neon colors and a vibrant red sun that appears to sink into the water off Vineyard Sound each evening at dusk to applause of onlookers,” raves one islander.

No joke, people cheer.

Worthy of applause: sunsets on Menemsha Harbor are a cause for celebration. (Tea Lane Associates)

That’s the kind of love folks feel for Menemsha. In return, the village remains true to itself, a rare old-timey enclave on the island that remains untouched by Starbucks, chain stores and spa hotels.

Part of the larger town of Chilmark, the village keeps its connection to the sea close. The Wampanoags fished these waters for thousands of years before European settlers arrived in the 1600s. The Native Americans (whose descendants live in nearby Aquinnah) shared their fishing and planting skills, vital for the newcomers’ survival. They also taught Plymouth Colony newbies whaling, which became a booming fuel business until the mid-19th century.

Fast forward to the 1900s when Menemsha became known as a mecca for swordfish. Indeed, a 17-foot-tall sculpture at the local beach of a fisherman harpooning one of the sea creatures pays homage to the onetime industry.

In Menemsha – and at 94 Menemsha Inn Road in particular – privacy reigns. Perhaps even more so amid the growing interest from ultra-high-net-worth individuals. (Tea Lane Associates)

But nothing prepared the village for what would happen three decades later. The modest fishing shacks and homes in Menemsha were swept away by the Great New England Hurricane of 1938, a brutal storm that killed 700 people and raked Massachusetts, Connecticut, New York and Rhode Island. Nothing was left standing, the town was wiped off the map.

With gentle strength, the people of Menemsha rebuilt and recaptured their livelihood. The historic harbor today dates to the rebuilt town, which may look familiar, even if you’ve never been there. In 1975, Steven Spielberg tapped Menemsha to serve as a stand-in for the fictional Amity Island in the hit film Jaws

That’s the kind of love folks feel for Menemsha. In return, the village remains true to itself.

Despite the Hollywood star turn, Menemsha avoided becoming a touristy filming stop. Generations of fishermen still sail out in the morning (including the Little Lady, an old manually steered boat that’s the subject of many artists’ paintings) and return to sell freshly caught scallops, crab and the whitefish fluke. A local nonprofit safeguards the livelihood of the fishermen, posting their family’s stories online under the heading “Meet Your Fisherman.” 

So what attracts the ultra-affluent? Ex-presidents, Hollywood celebs and CEOs like Menemsha for the same reasons locals do: it’s a place to sample a slow-paced, simpler island lifestyle without distractions. Lots are large (no McMansions, yet) with plenty of privacy, courtesy of the surrounding bodies of water and natural boundaries.

The town’s setting on one of the inland great ponds, Menemsha Pond, and Vineyard Sound make it a natural for boating, swimming, kayaking and, yes, sunset gawking. Some families visit to make generational memories at summer compounds, far from their more complicated mainland lives.

The most sought-after amenities for homeowners: properties with waterfront and a boating dock. It makes it easy to swim, kayak, canoe, paddle board or even just bird-watch from your backyard. Whether homes face Menemsha Pond or the calmer waters of the Sound, grandfathered-in docks become the center point for water activities. (New permits for new docks can take years to obtain.) 

For example, 1 Clam Point Cove Road comes with a 48-foot boating dock and a separate mooring for access to the pond. The five-bedroom home and a separate contemporary guest house sit on three acres and command views of the pond from just about every inside space. The terraced lawn gives way to a private waterfront for swimming in summer, clamming year-round and just about any other water sport or activity. It was the longtime family home of John Lee Jr., a Yale basketball star in the 1950s who passed up playing professionally for a career in corporate America. 

Permitted or grandfathered-in docks, as at 1 Clam Point Cove Road, remain the region's most prized possession. (Tea Lane Associates)

The private waterfront at 94 Menemsha Inn Road faces Vineyard Sound where waters are calmer than the ocean side of the island. The property looks out on sailboats and gets the best of the island’s incredible sunsets. Sitting on 5.6 acres with a natural buffer of trees and greenery at the end of a quiet road, privacy quietly abounds. 

The main four-bedroom house with a separate one-bedroom guest studio stands at a high point on the property, with plenty of space to expand. A short path leads down to the private beach space. A 20-minute walk takes you to the village for dinner, an ice cream or more sunset-watching on the beach.

Aerial view of 34 Edys Island Way on Martha's Vineyard
Built in 1950 and cared for by four generations of the same Island family, the waterfront home known as Le Rêve enjoys dreamy views of Menemsha Pond. (Tea Lane Associates)

The home at 34 Edy’s Island Way is waterfront with a private dock on Menemsha Pond. It was built in 1950 by a longtime island family who nicknamed their dream home Le Rêve (French for “The Dream”). The four-bedroom house with a detached one-bedroom guest house enjoys views of Menemsha Pond and sunset views of the harbor – and it’s only a short stroll from the house into town. The private dock on Menemsha Pond lets you launch a boat and also access Vineyard Sound.

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