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59 Hagerty Drive

Tisbury, MA 02568

Offered at$6,150,000

Residential · Active · MLS #73565263
Listing Courtesy of Donnelly + Co. | Carol Shore

6Bedrooms
7Bathrooms
5,034Square feet
2003Year built

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MLS PIN data

About this home

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.

Property information

Details at a glance

Interior

Rooms
14
Heating
Forced Air, Propane
Cooling
Central Air

Building

Style
Single Family Residence
Year built
2003
Garage
2
Parking
8
Foundation
Concrete Perimeter

Land & utilities

Lot size
1.15 acres
Water
Public
Sewer
Private Sewer
Zoning
R50

Financial

Annual taxes
$32,594
Assessment year
2026

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$8,697,802

Estimated range $7,358,330$10,037,274

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Tisbury

MetricThis propertyTisbury
List price$6,150,000$1,997,000208% above local
Price / sq ft$1,222$1,1645% above local
Days on market169283% below local
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Active city listing statistics from MLS PIN as of September 5, 2026. Asking prices are not completed-sale values.

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Common questions

About 59 Hagerty Drive

Can I schedule a private showing?

Yes. Request a tour of 59 Hagerty Drive and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.