Oak Bluffs, MA

Oak Bluffs Real Estate

65Results

Oak Bluffs is a classic beach resort town on the northeast shore of Martha's Vineyard. Real estate in Oak Bluffs includes condos, single family homes, homes with dock access, acreage, and more. Whether you’re looking for a permanent residence or a vacation home, Hancock Real Estate can help you find your island dream home.

Price High to Low
New Listing
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
  • 29 Days on Market
Listed by Compass LLC
MLS#: 44397

$5,995,000

Oak Bluffs, MA

Sengy

43 Sengekontacket Road

  • 3 Beds
  • 3 Baths
  • 2.897 Acres
  • 2,234 SqFt
  • 114 Days on Market
Listed by Studio Realty
MLS#: 36712

$5,495,000

Oak Bluffs, MA

Lagoon/Harbor

385 Barnes Road

  • 3 Beds
  • 6 Baths
  • 0.98 Acres
  • 3,608 SqFt
  • 59 Days on Market
Listed by Donnelly + Co
MLS#: 42465

$5,450,000

Oak Bluffs, MA

Central

8 Paddock Road

  • 4 Beds
  • 6 Baths
  • 1.95 Acre
  • 3,300 SqFt
  • 36 Days on Market
Listed by Sandpiper Realty
MLS#: 44395

$5,325,000

Oak Bluffs, MA

Downtown

4 Canonicus Avenue

  • 6 Beds
  • 4 Baths
  • 0.2 Acres
  • 2,890 SqFt
  • 344 Days on Market
Listed by Sandpiper Realty
MLS#: 43452

$5,250,000

Oak Bluffs, MA

Lagoon/Harbor

217 Barnes Road

  • 5 Beds
  • 4 Baths
  • 1.8 Acre
  • 3,650 SqFt
  • 65 Days on Market
Listed by Tea Lane Associates
MLS#: 44172

$5,100,000

Oak Bluffs, MA

Sengy

7 Overview Lane

  • Land
  • 2.337 Acres
  • 49 Days on Market
Listed by Wallace & Co. Sotheby's
MLS#: 44341
New Listing

$4,950,000

Oak Bluffs, MA

Sengy

15 Tamarack Lane

  • 6 Beds
  • 6 Baths
  • 3.697 Acres
  • 3,998 SqFt
  • 14 Days on Market
Listed by Donnelly + Co
MLS#: 44208

$4,695,000

Oak Bluffs, MA

Sengy

8 Fresh Pond Road

  • 7 Beds
  • 5 Baths
  • 1.57 Acre
  • 5,320 SqFt
  • 73 Days on Market
Listed by Keller Williams Realty
MLS#: 44237

$3,995,000

Oak Bluffs, MA

Sengy

98 Farm Neck Way

  • Land
  • 1.917 Acre
  • 56 Days on Market
Listed by Compass LLC
MLS#: 44316

$3,750,000

Oak Bluffs, MA

Lagoon/Harbor

28 Beach Road

  • 4 Beds
  • 3 Baths
  • 0.99 Acres
  • 1,800 SqFt
  • 72 Days on Market
Listed by Lewis Real Estate Services,LLC
MLS#: 44234

$3,250,000

Oak Bluffs, MA

East Chop

6 Brewster Avenue

  • 4 Beds
  • 3 Baths
  • 0.115 Acres
  • 1,728 SqFt
  • 277 Days on Market
Listed by Sandpiper Realty
MLS#: 42895

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Based on information submitted to LINKMV as of June 5, 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.