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Properties For Sale In Oak Bluffs

Properties For Sale In 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.

1 - 18 of 80 properties

51 Winemack Street

For sale

$1,245,000

Listed Oct 31, 2026

51 Winemack Street

Oak Bluffs, MA 02557

Beds
2
Baths
2
Acres
0.23
Built
1979
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1 Paulding Avenue

For sale

$4,000,000

Listed Oct 30, 2026

1 Paulding Avenue

Oak Bluffs, MA 02568

Beds
6
Baths
6.5
Acres
0.35
Built
2022
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38 Meadow View Road

For sale

$1,699,000

Listed Oct 30, 2026

38 Meadow View Road

Oak Bluffs, MA 02557

Beds
4
Baths
2.5
Acres
0.79
Built
1995
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4 Beryl Way

For sale

$995,000

Listed Oct 26, 2026

4 Beryl Way

Oak Bluffs, MA 02557

Beds
2
Baths
1
Acres
0.3
Built
1900
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25 Oak Avenue

For sale

$1,950,000

Listed Oct 22, 2026

25 Oak Avenue

Oak Bluffs, MA 02557

Beds
2
Baths
2
Acres
0.2297
Built
1900
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31 Beacon Avenue

For sale

$895,000

Listed Oct 17, 2026

31 Beacon Avenue

Oak Bluffs, MA 02557

Beds
3
Baths
1.5
Acres
0.11
Built
1982
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15 Stone Pound Way

For sale

$2,490,000

Listed Oct 14, 2026

15 Stone Pound Way

Oak Bluffs, MA 02557

Beds
3
Baths
3.5
Acres
0.3
Built
1980
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22 Trinity Park

For sale

$1,550,000

Listed Oct 7, 2026

22 Trinity Park

Oak Bluffs, MA 02557

Beds
4
Baths
2
Built
1870
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109 Forest Avenue

For sale

$425,000

Listed Oct 6, 2026

109 Forest Avenue

Oak Bluffs, MA 02557

Acres
0.2506
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8 Pequot Avenue

For sale

$1,775,000

Listed Oct 5, 2026

8 Pequot Avenue

Oak Bluffs, MA 02557

Beds
5
Baths
1.5
Acres
0.0599
Built
1870
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10 Ploughshare Lane

For sale

$1,489,000

Listed Oct 3, 2026

10 Ploughshare Lane

Oak Bluffs, MA 02557

Beds
3
Baths
2.5
Acres
13068
Built
1981
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31 Circuit Avenue Extension

For sale

$5,500,000

Listed Oct 1, 2026

31 Circuit Avenue Extension

Oak Bluffs, MA 02557

Beds
4
Baths
5
Acres
0.2007
Built
1913
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39 Chickawaukee Street

For sale

$1,399,000

Listed Sep 24, 2026

39 Chickawaukee Street

Oak Bluffs, MA 02557

Beds
3
Baths
2
Acres
0.1199
Built
1996
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455 County Road

For sale

$1,200,000

Listed Sep 24, 2026

455 County Road

Oak Bluffs, MA 02557

Acres
1.397
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234 County Road

For sale

$1,375,000

Listed Sep 23, 2026

234 County Road

Oak Bluffs, MA 02557

Beds
5
Baths
2
Acres
0.2399
Built
1973
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68 Front Street

For sale

$1,755,000

Listed Sep 17, 2026

68 Front Street

Oak Bluffs, MA 02557

Beds
3
Baths
3
Acres
0.3443
Built
1995
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61 Canonicus Avenue

For sale

$2,200,000

Listed Sep 12, 2026

61 Canonicus Avenue

Oak Bluffs, MA 02557

Beds
3
Baths
2.5
Acres
0.23
Built
1999
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15 Rogers Way

For sale

$850,000

Listed Sep 11, 2026

15 Rogers Way

Oak Bluffs, MA 02557

Acres
0.25
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Martha's Vineyard Real Estate Properties By Town

Vineyard Haven

Vineyard Haven

Vineyard Haven Areas

Oak Bluffs

Oak Bluffs

Oak Bluffs Areas

Edgartown

Edgartown

Edgartown Areas

West Tisbury

West Tisbury

West Tisbury Areas

Chilmark

Chilmark

Chilmark Areas

Aquinnah

Aquinnah

Aquinnah Areas

Martha's Vineyard Real Estate Properties By Type

Single Family Homes in Martha's Vineyard

Single Family

Searching for a single-family home on Martha's Vineyard? With Anchor Realty Real Estate, you can count on receiving personalized service & solutions! Call +1 (508) 696-7777 today.

Condos for Sale in Martha's Vineyard

Condos

Anchor Realty Real Estate is your source for all of your real estate needs. Whether you're looking for a condo or a second home, we are here for you. Call +1 (508) 696-7777 today.

Commercial Properties for Sale in Martha's Vineyard

Commercial

Looking for commercial properties for sale in Martha's Vineyard? Count on the team at Anchor Realty Real Estate for all of your real estate needs. Call +1 (508) 696-7777 today.

Land for Sale in Martha's Vineyard

Land

Looking for land for sale in Martha's Vineyard? The team at Anchor Realty Real Estate is your source for expert real estate services, resources & more. Call +1 (508) 696-7777 today.

Multi-Family Homes in Martha's Vineyard

Multi Family

With Anchor Realty Real Estate, you can count on us to help you find the perfect multi-family home on Martha's Vineyard. Contact us today for listings & more. Call +1 (508) 696-7777 today.