66 Hudson Avenue
Oak Bluffs, MA · $1,296,000
Zillow ↗
📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

66 Hudson Avenue

Oak Bluffs, MA 02557
$1,296,000
2 days on market · Listed Aug 14, 2026
Data refreshed Aug 14, 2026
🌊 Not in FEMA SFHA
View on Zillow ↗
Type
SF
Beds
3
Baths
2
Sq Ft
908
Acres
0.23
Year Built
1988
$ / Sq Ft
$1,427
Days on Market
2

Investment Snapshot

Monthly Carrying
$••,•••
Cash Flow / yr
$••,•••
Cash-on-Cash
••%
Cash Required
$••,•••
Projected Revenue / yr
$••,•••
Avg Daily Rate
$••,•••
Occupancy
••%
STR Range (P50)
$••,•••

Location & Nearby

Map of 66 Hudson Avenue, Oak Bluffs MA with nearby beaches and points of interest
HThis property
  • A
    🚴 County Road Bike Path
    0.69 mi
  • B
    🌲 Trade Wind Fields Preserve
    0.72 mi
  • C
    🍽️ Farm Neck Cafe
    0.90 mi
  • D
    Farm Neck Golf Club
    0.93 mi
  • E
    🍽️ Mo's Lunch
    0.93 mi
  • F
    🛒 Tony's Market
    1.07 mi
  • G
    🍽️ Black Joy Kitchen
    1.09 mi
  • H
    🌲 Doug's Cove Preserve
    1.19 mi

About this property

This warm and welcoming home with exceptional outdoor living space is sited on a beautifully landscaped lot just 1.5 miles from downtown Oak Bluffs. The private backyard, designed and cultivated by Donaroma's, features a fenced lawn with irrigation, fire pit, outdoor dining area, and built-in grill-ideal for entertaining and relaxing. The open kitchen and living floor plan overlooks the backyard. Two bedrooms and a full bath on the main level. The finished lower level adds approximately 908 square feet, including a third bedroom, full bath, and den-perfect for guests, movie nights, or extended living. Medeiras Cove is approximately 0.4 miles away, offering access for kayaking, paddle boarding, and sunset views over the Lagoon. A convenient foot bath makes beach days easy. Offered furnished with a short list of exclusions, this property is ideal as a year-round home, vacation retreat, or investment property. The third bedroom, not reflected on the field card, is engineer-approved and has been reviewed by the Oak Bluffs Board of Health.

Similar listings in Oak Bluffs

📋 Oak Bluffs Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Oak Bluffs
Listed by Diana M Gilmore, Island Real Estate