Fairview on Greenleaf: A Vineyard Haven of Memory, History, and Unbeatable Views
Tucked into one of Oak Bluffs' most beloved streets, Fairview on Greenleaf Avenue isn’t just a home—it’s a front-row seat to the magic of Martha’s Vineyard. From its highest perch above Sunset Lake, the property offers panoramic views of Oak Bluffs Harbor and Nantucket Sound, where sunrises dazzle the sky and summer fireworks light up the night like a private show.
Lovingly cared for by the same family for over 27 years, this three-bedroom home was designed by island architect Jaime Weisman to reflect the whimsical charm of the nearby gingerbread cottages. It includes a finished basement for flexible living or working space, and a multipurpose outbuilding that doubles as a shed and garage. With off-street parking and a private yard, the home is both serene and conveniently located—just steps away from Ocean Park, the Tabernacle, Illumination Night, and the best of Oak Bluffs.
A Window Into the Past—and a Bright Future
Once known as “Crossing the Jordan,” this footbridge over Sunset Lake was the main entry point to Oak Bluffs in the early 1900s. Residents and visitors alike would stroll across it, row beneath it, and gather in the adjacent park for clamming, boating, and relaxing along the shoreline. Though the bridge no longer stands, the area is experiencing a renaissance.
In 2021, the Town of Oak Bluffs, together with the Friends and Neighbors of Sunset Lake (FANS), launched a $750,000 restoration initiative to revitalize this historic waterway. The project included the removal of invasive species, installation of bioretention systems to improve water quality, and new landscaping with native vegetation. A pedestrian pathway now winds around the lake, complemented by bike racks, a welcome kiosk, and dog-friendly amenities.
The results? Healthier water, a thriving park, and a renewed sense of community around this gem. The lake is once again a serene focal point, adding both beauty and ecological value to the neighborhood—and to Fairview’s front-row view.
Generations of Family, Fun, and Island Traditions
Fairview isn’t just a house—it’s a family’s memory vault. Over the years, it has been the site of August chaos with cousins, sunset cocktail parties on the roof deck, and magical nights of stargazing. It’s where kids watched fireworks from their own rooftop, and where one unforgettable visit to the old OB fire station led to a spontaneous joyride in a fire truck—an iconic small-town moment if there ever was one.
From beach days at Inkwell and South Beach to sugar-fueled birthdays with flourless chocolate cake from The Scottish Bakehouse, this house has been at the heart of decades of Vineyard traditions. The family spent spring breaks here, walked their dogs through Trade Wind Fields Preserve, and made annual pilgrimages to the Ag Fair to watch skillet tosses and admire local art. And of course, one fateful summer, they watched the mechanical shark from Jaws being worked on daily near their beach—scarring one sibling into a lifetime of landlocked living. Thanks, Spielberg.
Deep Roots in Oak Bluffs History
The home sits on land once part of a trio of lots owned by the Legg family in the early 20th century. In the 1920s, John L. Legg and his wife Ida built their cottage on what is now the back section of 24 Greenleaf. Their sons inherited the adjacent parcels, and the current owners purchased the home at #22 from John Legg after he relocated to England. It’s believed Ida may have played a role in preserving the undeveloped stretch of Lakeside Park across the street, helping to ensure that the views from Fairview would remain open and unobstructed for generations to come.
Architectural Soul Meets Everyday Comfort
Designed with intention and heart, Fairview captures the spirit of the island without sacrificing function. With three bedrooms, a finished basement, ample outdoor space, and a yard perfect for entertaining or relaxing, the home offers flexibility and peace. The garage/shed outbuilding, private parking, and unbeatable location round out a property that’s as livable as it is lovable.
A Rare Opportunity to Own a Slice of Vineyard Lore
Fairview on Greenleaf is that rare find—rich in history, brimming with character, and blessed with some of the best views on Martha’s Vineyard. Whether you’re looking for a legacy property, a personal retreat, or a home base to build new traditions, Fairview is ready for its next chapter.
And yes, the fireworks are still spectacular from the roof.
