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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 84 properties

31 Circuit Ave Ext

For sale

$5,500,000

Listed Oct 1, 2026

31 Circuit Ave Ext

Oak Bluffs, MA 02557

Beds
4
Baths
5
Acres
0.2007
Built
1913
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39 Chickawaukee Street

For sale

$1,475,000

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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15 Pequot Avenue

For sale

$2,150,000

Listed Sep 18, 2026

15 Pequot Avenue

Oak Bluffs, MA 02557

Beds
5
Baths
3
Acres
0.1
Built
1890
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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
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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8 Melrose Avenue

For sale

$1,539,000

Listed Sep 10, 2026

8 Melrose Avenue

Oak Bluffs, MA 02557

Beds
3
Baths
4
Acres
0.25
Built
1978
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267 Barnes Road

For sale

$4,395,000

Listed Sep 8, 2026

267 Barnes Road

Oak Bluffs, MA 02557

Beds
3
Baths
5
Acres
1.25
Built
2000
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4 Periwinkle Lane

For sale

$1,295,000

Listed Sep 8, 2026

4 Periwinkle Lane

Oak Bluffs, MA 02557

Beds
3
Baths
2
Acres
0.26
Built
2014
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3 Oak Bluffs Avenue

For sale

$5,000,000

Listed Sep 5, 2026

3 Oak Bluffs Avenue

Oak Bluffs, MA 02568

Baths
1
Acres
0.28
Built
1975
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51 Winemack Street & 0 Meadow Ave & Nahomon Street

For sale

$2,045,000

Listed Sep 1, 2026

51 Winemack Street & 0 Meadow Ave & Nahomon Street

Oak Bluffs, MA 02557

Beds
2
Baths
2
Acres
0.47
Built
1979
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4 Lagrange Avenue

For sale

$1,450,000

Listed Aug 31, 2026

4 Lagrange Avenue

Oak Bluffs, MA 02557

Beds
3
Baths
2
Acres
0.1768
Built
1998
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53 Circuit Avenue

For sale

$5,500,000

Listed Aug 21, 2026

53 Circuit Avenue

Oak Bluffs, MA 02557

Beds
6
Baths
4
Acres
0.06
Built
1900
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53 Circuit Avenue

For sale

$5,500,000

Listed Aug 21, 2026

53 Circuit Avenue

Oak Bluffs, MA 02557

Beds
6
Baths
4
Acres
0.06
Built
1900
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24 Harrison Avenue

For sale

$2,595,000

Listed Aug 21, 2026

24 Harrison Avenue

Oak Bluffs, MA 02557

Beds
2
Baths
2
Acres
0.16
Built
2018
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21 island Inn Road 38G

For sale

$389,000

Listed Aug 16, 2026

21 island Inn Road 38G

Oak Bluffs, MA 02557

Beds
1
Baths
1
Built
1983
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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.