22 Greenleaf Avenue, Oak Bluffs MA 02539

Immersed in the picturesque setting of Oak Bluffs on Martha’s Vineyard, Fairview on Greenleaf Avenue, one of only ten homes in this coveted location, harmoniously blends historical charm with coastal serenity. This cherished family home holds a special place in the hearts of its owners, with roots tracing back to childhood memories and the family’s Rochester, NY home on Fairview Crescent.

Architecturally designed to echo the local gingerbread cottages, an addition seamlessly integrates with Oak Bluffs’ historical aesthetic. The highlight? A rooftop deck, offering unparalleled views—the highest point on Greenleaf Ave—overlooking Lakeside Park, the rejuvenated Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound beyond. This commanding viewpoint makes Fairview the ideal spot for enjoying the annual Oak Bluffs fireworks display and glorious sunrises.

For over 27 years, Fairview has been a sanctuary of family memories, lovingly maintained and enjoyed by multiple generations. It features three bedrooms and a finished basement that provides additional flexible living space. See the included photos to envision how the lower level would look with furniture and a traditional staircase. The spacious backyard and the large multipurpose building, which functions as both a shed and garage, add to the property’s charm and utility. The large lot includes ample parking off of Gorham Ave.

Located on a peaceful side street, Fairview enjoys proximity to the heart of Oak Bluffs’ vibrant community life, including traditions like Illumination Night, concerts at the Tabernacle, and walks to Ocean Park. Yet, it offers a quiet retreat, close to all the town’s amenities without being in the midst of the hustle and bustle.

Noteworthy is the involvement of Island architect Jaime Weisman in the addition, ensuring thoughtful design and execution. Fairview isn’t just a home; it’s a gateway to a lifestyle enriched by the enchantment of Oak Bluffs, celebrated for its historic landmarks and coastal charm. It represents a rare opportunity to continue a legacy of creating memories in a setting that combines the best of Martha’s Vineyard’s natural beauty and cultural richness.