Oak Bluffs Investment Properties
Gingerbread cottages, harbor nightlife, and the Vineyard's most rental-friendly zoning.
Active Listings
29
Median Price
$1,595,000
Lowest
$599,000
Highest
$5,450,000
Recent Oak Bluffs Listings
82 Pennsylvania Avenue$1,296,000 · 3 bd · 1.5 ba · 1,144 sqft
40 Hidden Cove Road$1,595,000 · 3 bd · 3.5 ba · 2,739 sqft
11 Beach Road$1,745,000 · 2 bd · 1 ba · 561 sqft
60r Carol Lane$794,000 · 2 bd · 1 ba · 624 sqft
37 Circuit Avenue, Unit 5$869,000 · 1 bd · 1 ba · 797 sqft
47 Winemack Street$1,199,000 · 3 bd · 2 ba · 1,302 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 →