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Oak Bluffs Multifamily Homes & Duplexes for Sale

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  • /29

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 403-9601

    47 Winemack St, Oak Bluffs, MA 02557
  • /54

    $1,830,000

    • 4 Beds
    • 4 Baths
    • 1,600 Sq Ft

    12 & 14 Maple Ave, Oak Bluffs, MA 02557

    Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

    Leslie Floyd Portfolio Properties

    12 & 14 Maple Ave, Oak Bluffs, MA 02557
  • /39

    $5,325,000

    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

    Katherine Donahue Sandpiper Realty Inc

    4 Canonicus Ave, Oak Bluffs, MA 02557

Why Live in Oak Bluffs

Oak Bluffs, located in the northeast of Martha’s Vineyard, is renowned for its whimsical gingerbread houses and historical significance as a summer haven for Black Americans. This down-island town is a bustling port of entry during the summer season, where tourists disembark from ferry boats and explore attractions like Circuit Avenue, known for its T-shirts and fresh doughnuts. The town features gray-shingled beach houses overlooking the Nantucket Sound, and the commercial district offers pizza parlors, ice cream shops, and clothing stores. Oak Bluffs is home to the oldest platform carousel in the U.S., the Flying Horses Carousel, and hosts the Martha’s Vineyard African American Film Festival and a fireworks show every August. The Ritz Café provides nightlife with live music and karaoke, while the Sweet Life Café offers upscale dining year-round. Ocean Park, with its rolling hills and Victorian homes, and the Martha’s Vineyard Camp Meeting Association, with its brightly colored gingerbread houses, are notable landmarks. The town also has gray-shingled beach cottages, Cape Cods, and farmhouses. Martha’s Vineyard Regional High School, a highly rated institution, serves the island’s students. Health care is accessible at Mass General Brigham Martha’s Vineyard Hospital, which offers comprehensive services. Residents and visitors can enjoy sandy pathways along the Nantucket Sound, beaches like Inkwell Beach, and a skate park near the high school. Oak Bluffs is 10 minutes from Vineyard Haven, 15 minutes from Edgartown, and 15 minutes from Martha’s Vineyard Airport.

Home Trends in Oak Bluffs, MA

Housing Trends

Median Sale Price
$612,247
Median Single Family Sale Price
$545,000
Median Townhouse Sale Price
$284,990
Median 2 Bedroom Sale Price
$287,500
Average Price Per Sq Ft
$248
Number of Homes for Sale
5
Last 12 months Home Sales
16
Months of Supply
3.80
Median List Price
$475,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
32%
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