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554 East 4th St
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  1. Home
  2. Listings
  3. 59 Hagerty Drive, Tisbury, MA 02568
Active
2 Days on market
59 Hagerty Drive Tisbury — Photo 1 of 37

59 Hagerty Drive Tisbury — Photo 1 of 37

$6,150,000

59 Hagerty Drive, Tisbury, MA 02568

Tisbury, MA 02568

Beds

6

Baths

6

SqFt

5,034

Style

Single Family

Built

2003

Tucked away on a quiet street in coveted West Chop, this pristine property offers exceptional privacy, stunning scenery, and easy access to downtown Vineyard Haven. Designed for effortless indoor-outdoor living, this sophisticated compound combines timeless charm with every modern amenity. The first floor features an inviting open-concept layout ideal for both relaxed family living and entertaining. The kitchen overlooks the dining area, an intimate sitting area, and a versatile game and reading area beyond. The spacious TV and family room features custom built-in bookcases and French doors that open onto a bluestone patio and the pool area beyond. A generous screened porch provides additional living space. Completing the first floor is a large guest bedroom with an ensuite bath, along with a powder room, pantry, mudroom, and laundry room. Upstairs, the gracious primary suite features vaulted ceilings, a sitting area, and a luxurious bath with a soaking tub. There are two additional guest bedrooms, each with an ensuite bath. A private sun deck overlooks the pool and beautifully landscaped grounds, offering a wonderful spot to relax and enjoy distant water views. A dedicated office with water views toward Woods Hole and the Elizabeth Islands provides an inspiring setting for work or quiet retreat. Above the garage, a separate one-bedroom apartment offers a full kitchen, bath, and laundry, with convenient interior and exterior access. The living space in the apartment is currently being used as the sixth bedroom. Outside, the property transforms into a private oasis. The upper garden patio features an inviting sofa seating, while a stone staircase leads down to the heated 20' x 40' pool with spa. The expansive pool terrace is furnished with comfortable loungers and the pool cabana provides additional seating and a welcome retreat from the sun, all surrounded by lush, mature plantings. Other amenities include a gym, two enclosed outside showers and a pool powder room. With its exceptional privacy, generous living spaces, water views, pool and cabana, guest accommodations, this stunning property is truly one of the Grand Dames of West Chop.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$1222/sqft
Local Avg (Tisbury)$1207/sqft
1% AboveMarket Average

* Analysis is based on 21 actively listed and recently sold comparable properties strictly within Tisbury, MA.

Property Details

Financials

Original Price$6,150,000
Annual Taxes$32,594

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms14
FireplacesNone
Flooring--
BasementFull, Partially Finished

Climate & Utilities

HeatingForced Air, Propane
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter
ZoningR50

Property & Lot

Acres1.15
SqFt Lot50,093
Lot FeaturesGentle Sloping

Amenities & Appliances

Water Heater

Geography

Population

9,412

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$115K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

21.5%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Dukes County

164 housing units permitted in the last 12 months (+80% vs the prior 12 months) — 35 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 5,034 sq ft principal dwelling). Lot size: 50,093 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Tisbury, MA market report ZIP 02568 market data
Listing Provided By

Listing Agent: Carol Shore

Listing Office: Donnelly + Co.

MLS® Number: 73565263

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