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22 Greenleaf Avenue, Oak Bluffs

$2,390,000

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.

HIGHLIGHTS

Link ID 43058
Bedrooms 3
Baths 2
Rooms 7
Living Space 1608
Acreage 0.18

FEATURES AND AMENITIES

Link ID
43058
Price
$2,390,000
Baths
2
Rooms
7
Living Space
1608
Acreage
0.18
Zoning
R1
Water
Town
Sewer
Septic Tank
Heat
Electric
2025 Tax Assessment
$1,928,600
Building Assessment
$598,700
Land Assessment
$1,329,900
Estimated Taxes
$9,348
Outdoor Spaces
Beach Access - Public
Deck
Porch
Year Built
1987
Fireplaces
None
Flooring
3
Listing Broker
Compass | The O'Hanlon Group

22 Greenleaf Avenue, Oak Bluffs

Copyright 2025 LINK MV. All rights reserved. Information deemed reliable but is not guaranteed.
Buyer note, 2% Land Bank fee.
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