Homes with Pools on Martha’s Vineyard

62Results

Find Martha’s Vineyard homes with pools in Aquinnah, Chilmark, Edgartown, West Tisbury, Oak Bluffs, and Vineyard Haven. Martha’s Vineyard offers a wonderful seaside experience with world-class beaches, beautiful conservation areas, and a laid back lifestyle. 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
18 Point Inner Way Chilmark MA 02535

$45,000,000

Chilmark, MA

South

18 Point Inner Way

  • 7 Beds
  • 12 Baths
  • 4.9 Acres
  • 14,780 SqFt
  • 11 Days on Market
Listed by Wallace & Co. Sotheby's
MLS#: 44498

$22,950,000

West Tisbury, MA

Lambert's Cove

60 Bartimus Luce Road

  • 7 Beds
  • 9 Baths
  • 3.33 Acres
  • 8,200 SqFt
  • 389 Days on Market
Listed by Landvest MV
MLS#: 43263

$21,500,000

Edgartown, MA

Downtown

56 North Summer Street

  • 10 Beds
  • 13 Baths
  • 0.236 Acres
  • 7,598 SqFt
  • 59 Days on Market
Listed by Wallace & Co. Sotheby's
MLS#: 44194
New Listing

$19,900,000

Edgartown, MA

South Shore

33 Boldwater Road

  • 5 Beds
  • 6 Baths
  • 9.1 Acres
  • 6,577 SqFt
  • 29 Days on Market
Listed by Hancock Real Estate
MLS#: 44437

$16,900,000

Edgartown, MA

Downtown

114 North Water Street

  • 8 Beds
  • 8 Baths
  • 0 Acres
  • 6,041 SqFt
  • 86 Days on Market
Listed by Donnelly + Co
MLS#: 44182

$15,000,000

Edgartown, MA

Sengy

14 Cow Bay Road

  • 7 Beds
  • 8 Baths
  • 1.5 Acre
  • 6,462 SqFt
  • 35 Days on Market
Listed by Landvest MV
MLS#: 44402

$14,500,000

Chilmark, MA

South

64 Squibnocket Farm Road

  • 4 Beds
  • 5 Baths
  • 3.3 Acres
  • 3,705 SqFt
  • 675 Days on Market
Listed by Wallace & Co. Sotheby's
MLS#: 40007

$14,250,000

Edgartown, MA

Downtown

68 North Water Street

  • 6 Beds
  • 8 Baths
  • 0.306 Acres
  • 4,820 SqFt
  • 623 Days on Market
Listed by Wallace & Co. Sotheby's
MLS#: 42130

$12,500,000

Chilmark, MA

South

18 Spruce Gate Road

  • 5 Beds
  • 4 Baths
  • 6.2 Acres
  • 3,700 SqFt
  • 392 Days on Market
Listed by Wallace & Co. Sotheby's
MLS#: 43244
Pending

$12,500,000

West Tisbury, MA

Lambert's Cove

44 Forest Road

  • 6 Beds
  • 4 Baths
  • 4.2 Acres
  • 4,876 SqFt
  • 130 Days on Market
Listed by Studio Realty
MLS#: 44064
New Listing

$11,250,000

Edgartown, MA

Sengy

14 Trapps Pond Road

  • 7 Beds
  • 7 Baths
  • 1.79 Acre
  • 10,142 SqFt
  • 30 Days on Market
Listed by Landvest MV
MLS#: 44424
New Listing

$9,875,000

Chilmark, MA

South

6 Wakeman Road

  • 6 Beds
  • 6 Baths
  • 4 Acres
  • 3,758 SqFt
  • 9 Days on Market
Listed by Tea Lane Associates
MLS#: 44509

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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.