Oak Bluffs Investment Properties
Gingerbread cottages, harbor nightlife, and the Vineyard's most rental-friendly zoning.
Active Listings
17
Median Price
$1,595,000
Lowest
$510,000
Highest
$5,495,000
Recent Oak Bluffs Listings
19 Perkins Avenue$825,000 · 2 bd · 1 ba · 985 sqft
61 Ocean Avenue, Unit 4$1,399,000 · 1 bd · 1 ba · 546 sqft
22 Firehouse$950,000 · 2 bd · 1 ba · 1,074 sqft
Temahigan Avenue & Dover Street$1,200,000
33 Vineyard Avenue$1,995,000 · 3 bd · 2.5 ba · 1,431 sqft
22 Old Harbor Lane$1,850,000 · 4 bd · 2 ba · 1,833 sqft
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 →