22 Greenleaf Avenue

Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill the sky with color and a front-row seat to the town’s iconic fireworks display. This home’s unique architectural style nods to the area’s beloved gingerbread cottages, blending classic Vineyard character with thoughtful design by Island architect Jaime Weisman. The home has been lovingly maintained for over 27 years by one family, and now offers a wonderful opportunity for the next chapter. Fairview includes three bedrooms, a finished basement that offers flexible space for relaxing, entertaining, or working from home, and a multipurpose outbuilding that doubles as a shed and garage. With off-street parking and ample yard space, the property provides both convenience and charm. Though located just steps from the vibrant energy of Oak Bluffs—like Illumination Night, concerts at the Tabernacle, and strolls through Ocean Park—Fairview remains a serene retreat, offering privacy and tranquility. This is a rare chance to own a home that combines unbeatable views, a storied location, and the opportunity to update and personalize a treasured piece of Martha’s Vineyard.