Oak Bluffs

Once a suburb of Edgartown, Oak Bluffs came into its own in the mid-19th century thanks to the establishment of the Methodist Campgrounds. Today, however, Oak Bluffs has become to the place to go for nightlife on the island.

Sales

28 Beach Road, Oak Bluffs

$ 1,595,000
VIEWS, VIEWS & MORE VIEWS! Designed to not only capture the views of Vineyard Sound and beyond to Woods Holes as well as a straight shot down the Lagoon, but this home was also created to be a co [more]
VIEWS, VIEWS & MORE VIEWS! Designed to not only capture the views of Vineyard Sound a [more]
42.5 1,800 ft2full info
Sales

32 Temahigan Avenue, Oak Bluffs

$ 4,350,000
HISTORIC EAST CHOP WATERFRONT ESTATE WITH BOATHOUSE AND DEEP WATER DOCK. Originally built in 1870 with all of the grandeur of a 19th century seaside estate, this grand historic home features over 6,00 [more]
HISTORIC EAST CHOP WATERFRONT ESTATE WITH BOATHOUSE AND DEEP WATER DOCK. Originally built [more]
66 6,441 ft2full info
Sales

20 Bayes Hill Road, Oak Bluffs

$ 925,000
Bayes Hill Charmer…Three bedroom three and a half bath home surrounded by lovely perennial gardens with a wonderful open porch on the front and large private deck across the back of the home.
Bayes Hill Charmer…Three bedroom three and a half bath home surrounded by lovely per [more]
33.5 2,401 ft2full info
Sales

0 Front Street, Oak Bluffs

$ 175,000
Affordable building lot near the dog park. Currently a 1 bedroom lot requiring an enhanced treatment septic system. Recent Survey.
Affordable building lot near the dog park. Currently a 1 bedroom lot requiring an enhanced [more]
Sales

32 Iron Hill Road, Oak Bluffs

$ 829,000
A must see hidden gem this home lies on 1.52 acres featuring over 100k of reclaimed antique stone work. Located in a very private setting down island, 10 minutes from ferry and 15 minutes from beaches [more]
A must see hidden gem this home lies on 1.52 acres featuring over 100k of reclaimed antiqu [more]
32 1,534 ft2full info
Sales

10 Paddock Road, Oak Bluffs

$ 2,320,000
Under Construction: 4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of “The Preserve”. This home meets all the modern buyer’s nee [more]
Under Construction: 4000 sq ft of brand-new construction tucked nicely on a beautiful lot [more]
54.5 4,000 ft2full info
Sales

3 Nahomon Street, Oak Bluffs

$ 710,000
Don’t miss this opportunity to own the perfect Oak Bluffs get-away with a pool. Every inch of this Cape-style home has been well cared for. The home features brazilian cherry floors, updated kit [more]
Don’t miss this opportunity to own the perfect Oak Bluffs get-away with a pool. Ever [more]
22 1,131 ft2full info
Sales

311 East Chop Drive, Oak Bluffs

$ 2,250,000
Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can [more]
Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Ext [more]
42.5 1,496 ft2full info
Sales

50 Circuit Avenue, Oak Bluffs

$ 1,500,000
50 Circuit Avenue, circa 1900, completely renovated in 2003 and currently leased to the The Slice of Life, a long-established restaurant, is being offered for the first time in 15 years. The building [more]
50 Circuit Avenue, circa 1900, completely renovated in 2003 and currently leased to the Th [more]
11.5 1,753 ft2full info
Sales

225 East Chop Drive, Oak Bluffs

$ 3,950,000
Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece o [more]
Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. [more]
33.5 2,449 ft2full info
Sales

90 Dukes County Avenue, Oak Bluffs

$ 2,195,000
ULTRA CHIC + LUXE IN-TOWN MIXED-USE COMPOUND. Located within walking distance to Oak Bluffs town center and harbor, this luxurious designer’s own property is a one-of-a-kind opportunity — [more]
ULTRA CHIC + LUXE IN-TOWN MIXED-USE COMPOUND. Located within walking distance to Oak Bluff [more]
55.5 3,740 ft2full info
Sales

52 Head of the Pond Road, Oak Bluffs

$ 935,000
This contemporary 5 bedroom home is located in a nice area of fine homes and close to farm fields and conservation walking trails. The open floor plan includes a newly renovated kitchen, spacious livi [more]
This contemporary 5 bedroom home is located in a nice area of fine homes and close to farm [more]
53.5 3,100 ft2full info

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