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59 Hagerty Drive, Tisbury MA 02568

$6,150,000

Estimated $40,611/month Calculator

Single Family

6 Bedrooms

Baths

5034

Total Parking: 10 (2 Garage)

50,093 (1.15)

Built in 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.

This home has been viewed 4 times

Last Checked: September 15th, 2026 at 5:33am (Source: MLS PIN #73565263)

Garage Parking

Air Conditioning

Waterview

Lead Paint Free

General Information for 59 Hagerty Drive, Tisbury MA 02568

Listing ID73565263

Property TypeSingle Family / Detached

Price$6,150,000 ($1,221.69/SqFt)

StyleColonial

CityTisbury

CountyDukes

Neighborhood(s)

Garage Parking2

ZoningR50

Year Built2003

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 59 Hagerty Drive, Tisbury MA 02568

Approximate Living Area Total5034

Living Area Includes BasementNo

Rooms14

Bedrooms6

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

Flooring

Electric

Exterior Features for 59 Hagerty Drive, Tisbury MA 02568

Approximate Lot Size (Acres)1.15

Approximate Lot Size (Square Feet)50093

Total Parking10 (2 Garage)

Garage Parking2

WaterPublic

SewerPrivate Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior Features

Foundation Materials

Construction Materials

Road Frontage Type

Patio & Porch

Roof Material

Utility Connections

Water ViewsYes

Water Views Features

Waterfront0

Waterfront FeaturesRiver

Pool Features

Horse Permitted0

Horse AmenitiesRiver

Disclosures for 59 Hagerty Drive, Tisbury MA 02568

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsExcluded: Washer And Dryer Excluded.

Title 5D

Compensation Based On

Financial Information for 59 Hagerty Drive, Tisbury MA 02568

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax32594

Tax Year2026

Assessed Value$4,392,700

Location Information for 59 Hagerty Drive, Tisbury MA 02568

Neighborhood(s)

Area Amenities

Contact Information for 59 Hagerty Drive, Tisbury MA 02568

Agent

Name: Carol Shore

Office

Name: Donnelly + Co.

Phone: 508-627-1022

Team Members

Payment Calculator

, Interest

Property Taxes 2716.17

Principal & Interest 37894.34

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Donnelly + Co.

Carol Shore

Agent Phone

Office Phone

(508) 627-1022

Text Agent Call Agent Call Office

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EXIT

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