Oak Bluffs Investment Properties
Gingerbread cottages, harbor nightlife, and the Vineyard's most rental-friendly zoning.
Active Listings
34
Median Price
$1,599,000
Lowest
$549,000
Highest
$5,995,000
Recent Oak Bluffs Listings
43 Sengekontacket Road$5,995,000 · 3 bd · 3 ba · 2,234 sqft
59 Tuckernuck Avenue$2,650,000 · 4 bd · 2.5 ba · 1,858 sqft
28 Beach Road$3,675,000 · 4 bd · 2.5 ba · 1,800 sqft
21 Butler Avenue, Unit 1$1,075,000 · 3 bd · 2 ba · 1,135 sqft
26 Winthrop Avenue$839,000 · 1 bd · 1 ba · 804 sqft
68 Pond View Drive$975,000
Browse Oak Bluffs by Property Type
📋 Oak Bluffs Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for Airbnb & VRBO rentals in Oak Bluffs →