150 East Chop Drive
Tisbury, MA · $8,900,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

150 East Chop Drive

Tisbury, MA 02557
$8,900,000
307 days on market · Listed Mar 1, 2026
Data refreshed Apr 8, 2026
🌊 WaterfrontTax: $60,820/yr (2026)
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Type
SF
Beds
8
Baths
8
Sq Ft
8,560
Acres
0.64
Year Built
2017
$ / Sq Ft
$1,040
Days on Market
307

Investment Snapshot

🟡 MEDIUM RISK
Monthly Carrying
$48,771
Cash Flow / yr
$-454,844
Cash-on-Cash
-18.3%
Cash Required
$2,492,000
Projected Revenue / yr
$213,525
Avg Daily Rate
$1,147
Occupancy
51%
STR Range (P50)
$155,707
🟡 MEDIUM RISK — Registration required. Town meeting regulations.
STR revenue range: $99,272$216,117

Location & Nearby

Map of 150 East Chop Drive, Tisbury MA with nearby beaches and points of interest
HThis property
  • A
    East Chop Yacht Club
    0.43 mi
  • B
    🌲 Brightwood Park
    0.56 mi
  • C
    Oak Bluffs Marina
    0.71 mi
  • D
    🚤 Oak Bluffs Harbor Boat Ramp
    0.72 mi
  • E
    🍽️ Winston’s Kitchen
    0.78 mi
  • F
    🍽️ Honorary Tavern
    0.80 mi
  • G
    🍽️ Dockside Marketplace & Marina
    0.83 mi
  • H
    🍽️ The Black Dog Dockside Cafe (OB Harbor)
    0.83 mi

About this property

Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha's Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef's kitchen with island, high-end appliances, wet bar, and sunlit breakfast room flow seamlessly into the great room and screened porch. Spectacular dining room, reading room, laundry and 1st floor bedroom suite.The primary suite features panoramic water views, a private balcony, fireplace, outdoor shower, spa-like bath, and two dressing rooms. Seven additional bedrooms, create ample space for guests to luxuriate and relax. Lower level includes game room and gym. Outside, enjoy a sprawling lawn, decks, lush landscaping, and two outdoor showers. Close to East Chop Beach Club, Tennis Club, Yacht Club, Ferry, and Oak Bluffs shops. Be the envy of all you see!

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📋 Tisbury Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Tisbury
Listed by Melissa Dailey, Coldwell Banker Realty - Wellesley