385 Barnes Road
Oak Bluffs, MA · $5,495,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

385 Barnes Road

Oak Bluffs, MA 02557
$5,495,000
1 days on market · Listed Apr 7, 2026
Data refreshed Apr 8, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
3
Baths
5.5
Sq Ft
3,608
Acres
0.98
Year Built
2004
$ / Sq Ft
$1,523
Days on Market
1

Investment Snapshot

🟡 MEDIUM RISK
Monthly Carrying
$30,113
Cash Flow / yr
$-269,865
Cash-on-Cash
-17.5%
Cash Required
$1,538,600
Projected Revenue / yr
$146,891
Avg Daily Rate
$805
Occupancy
50%
STR Range (P50)
$108,512
🟡 MEDIUM RISK — Registration required. Town meeting regulations.
STR revenue range: $71,411$148,861

Location & Nearby

Map of 385 Barnes Road, Oak Bluffs MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Aquila at the Y Cafe - Smoothies & Acai
    1.19 mi
  • B
    🐕 Tisbury Dog Park (John G Rogers)
    1.52 mi
  • C
    🍽️ YEMVegan
    1.54 mi
  • D
    🛝 Community Services Playground
    1.56 mi
  • E
    🍽️ The Cove - Golf & Grill
    1.56 mi
  • F
    🍽️ The Cove - Golf & Grill
    1.56 mi
  • G
    🍽️ Catboat Coffee Co.
    1.62 mi
  • H
    🍽️ Rocco's Pizzeria
    1.62 mi

About this property

Set along 125 feet of private Lagoon frontage, this beautifully designed home offers over 5,400 sq. ft. of light-filled living space across three levels. High ceilings, skylights, and walls of glass capture sweeping water views, while a decorative stone fireplace anchors the main living area. The chef's kitchen features stainless appliances, stone counters, custom cabinetry, and a large island, complemented by a wet bar and casual dining area. Three ensuite bedrooms include a primary suite with water views, a sitting area, walk-in closet, pool access, and a spa-like bath. The walk-out lower level offers a game room, media area, kitchenette, wine storage, and bonus room. Outdoors, enjoy a heated pool, spa, bluestone terrace, and direct access to calm waters for swimming, boating, and some of the best steamers, littleneck, and cherry stones on the Island. Offered furnished with strong rental history.

📋 Oak Bluffs Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Oak Bluffs
Listed by Stephanie Roache, Donnelly + Co.