22 Greenleaf Ave

Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect Jaime Weisman. Lovingly maintained by one family for over 27 years, it now awaits its next chapter.Fairview includes three bedrooms, a finished basement for flexible living or work space, and a multipurpose outbuilding that functions as both shed and garage. With off-street parking and a generous yard, the property offers convenience and charm. Just steps from the heart of Oak Bluffs—Illumination Night, Tabernacle concerts, Ocean Park strolls—yet still a private, serene retreat.A rare chance to own a home with incredible views, historic charm, and space to make it your own.