Oak Bluffs, MA

Oak Bluffs Luxury Real Estate

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Newest
New Listing
1/37
47 Winemack Avenue Oak Bluffs MA 02557
47 Winemack Avenue Oak Bluffs MA 02557
47 Winemack Avenue Oak Bluffs MA 02557

$1,199,000

Oak Bluffs, MA

East Chop

47 Winemack Avenue

  • 3 Beds
  • 2 Baths
  • 0.115 Acres
  • 1,302 SqFt
  • 4 Days on Market
MLS#: 44490
New Listing
1/30
44 Tiffany Drive Oak Bluffs MA 02557
44 Tiffany Drive Oak Bluffs MA 02557
44 Tiffany Drive Oak Bluffs MA 02557

$3,245,000

Oak Bluffs, MA

Lagoon/Harbor

44 Tiffany Drive

  • 4 Beds
  • 5 Baths
  • 1.38 Acre
  • 3,927 SqFt
  • 5 Days on Market
MLS#: 44347
New Listing
1/12
0 Temahigan Avenue & Dover Street Oak Bluffs MA 02557
0 Temahigan Avenue & Dover Street Oak Bluffs MA 02557
0 Temahigan Avenue & Dover Street Oak Bluffs MA 02557

$1,200,000

Oak Bluffs, MA

East Chop

Temahigan Avenue & Dover Street

  • Land
  • 0.25 Acres
  • 6 Days on Market
MLS#: 43457
Active Under Contract
1/38
16 Atlantic Avenue Oak Bluffs MA 02557
16 Atlantic Avenue Oak Bluffs MA 02557
16 Atlantic Avenue Oak Bluffs MA 02557

$2,495,000

Oak Bluffs, MA

East Chop

16 Atlantic Avenue

  • 6 Beds
  • 3 Baths
  • 0.497 Acres
  • 2,577 SqFt
  • 12 Days on Market
MLS#: 44455
New Listing
1/41
150 East Chop Drive Oak Bluffs MA 02575
150 East Chop Drive Oak Bluffs MA 02575
150 East Chop Drive Oak Bluffs MA 02575

$8,900,000

Oak Bluffs, MA

East Chop

150 East Chop Drive

  • 8 Beds
  • 8 Baths
  • 0.64 Acres
  • 8,170 SqFt
  • 13 Days on Market
MLS#: 44397
New Listing
1/30
66 Barnes Road Oak Bluffs MA 02557
66 Barnes Road Oak Bluffs MA 02557
66 Barnes Road Oak Bluffs MA 02557

$1,245,000

Oak Bluffs, MA

Lagoon/Harbor

66 Barnes Road

  • 2 Beds
  • 2 Baths
  • 0.115 Acres
  • 1,752 SqFt
  • 15 Days on Market
MLS#: 43795
Open House
1/34
33 Vineyard Avenue Oak Bluffs MA 02557
33 Vineyard Avenue Oak Bluffs MA 02557
33 Vineyard Avenue Oak Bluffs MA 02557

$1,995,000

Oak Bluffs, MA

Downtown

33 Vineyard Avenue

NEXT OPEN HOUSE:

Sun 5/24 11:00 AM to 1:00 PM

  • 3 Beds
  • 3 Baths
  • 0.119 Acres
  • 1,431 SqFt
  • 18 Days on Market
MLS#: 44349
New Listing
1/46
8 Paddock Road Oak Bluffs MA 02557
8 Paddock Road Oak Bluffs MA 02557
8 Paddock Road Oak Bluffs MA 02557

$5,450,000

Oak Bluffs, MA

Central

8 Paddock Road

  • 4 Beds
  • 6 Baths
  • 1.95 Acre
  • 3,300 SqFt
  • 20 Days on Market
MLS#: 44395
New Listing
1/40
46 Kennebec Avenue Oak Bluffs MA 02557
46 Kennebec Avenue Oak Bluffs MA 02557
46 Kennebec Avenue Oak Bluffs MA 02557

$1,395,000

Oak Bluffs, MA

Downtown

46 Kennebec Avenue

  • 4 Beds
  • 2 Baths
  • 0.06 Acres
  • 1,305 SqFt
  • 27 Days on Market
MLS#: 44374
New Listing
1/27
22 Old Harbor Lane Oak Bluffs MA 02557
22 Old Harbor Lane Oak Bluffs MA 02557
22 Old Harbor Lane Oak Bluffs MA 02557

$1,850,000

Oak Bluffs, MA

Sengy

22 Old Harbor Lane

  • 4 Beds
  • 2 Baths
  • 0.47 Acres
  • 1,833 SqFt
  • 27 Days on Market
MLS#: 44113
New Listing
1/16
10 Winthrop Avenue Oak Bluffs MA 02557
10 Winthrop Avenue Oak Bluffs MA 02557
10 Winthrop Avenue Oak Bluffs MA 02557

$1,195,000

Oak Bluffs, MA

Downtown

10 Winthrop Avenue

  • 3 Beds
  • 2 Baths
  • 0.15 Acres
  • 1,188 SqFt
  • 29 Days on Market
MLS#: 44311
1/14
7 Overview Lane Oak Bluffs MA 02557
7 Overview Lane Oak Bluffs MA 02557
7 Overview Lane Oak Bluffs MA 02557

$5,100,000

Oak Bluffs, MA

Sengy

7 Overview Lane

  • Land
  • 2.337 Acres
  • 33 Days on Market
MLS#: 44341

Oak Bluffs Luxury Properties For Sale

Based on information submitted to LINKMV as of May 19, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.