
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.
Key facts
It was listed on August 18, 2026. The annual property taxes are $32,594 (2026 tax year). It sits on a 1.15-acre (50,093 sq ft) lot.
Market Value Analysis
* Analysis is based on 17 actively listed and recently sold comparable properties strictly within Tisbury, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater
Geography
Questions about this home
When was 59 Hagerty Drive, Tisbury listed?
59 Hagerty Drive, Tisbury was listed on August 18, 2026.
Has the price of 59 Hagerty Drive, Tisbury changed?
The price hasn't changed since it was listed at $6,150,000.
What are the property taxes for 59 Hagerty Drive, Tisbury?
The annual property taxes for 59 Hagerty Drive, Tisbury are $32,594 (2026 tax year).
How big is the lot at 59 Hagerty Drive, Tisbury?
59 Hagerty Drive, Tisbury sits on a 1.15-acre (50,093 sq ft) lot.
What is the status of 59 Hagerty Drive, Tisbury?
59 Hagerty Drive, Tisbury is actively listed for sale.
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
170 housing units permitted in the last 12 months (+110% vs the prior 12 months) — 35 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '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.
Listing Agent: Carol Shore
Listing Office: Donnelly + Co.
MLS® Number: 73565263







