59 Hagerty Drive Tisbury, MA $ 6,150,000
59 Hagerty Drive
$ 6,150,000
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59 Hagerty Drive

Tisbury, MA, 02568
$ 6,150,000
Bedrooms6 Baths5.2 Sq 5,034

Monthly Estimate*

$ 38,832

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Single Family Home for sale in Tisbury, MA

for $6,150,000 with 6 bedrooms and 5 full baths, 2 half baths. This 5,034 square foot home was built in 2003 on a lot size of 1.15.

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.

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Single Family Active

Price

$ 6,150,000

Bedrooms

6

Full Bath

5

Half Bath

2

Property Type

Single Family

Taxes

$ 32,594

Style

Lot Size

1.15

Year Built

2003

Town/City

Tisbury

County/Region

Dukes

MLS | Web ID

73565263

List By
Carol Shore

Listing Agent

Donnelly + Co.

Broker

Affordability Calculator

$41,548
Per Month
93%
7%
0%
Monthly Principal & Interest
$38,832
Monthly Property Taxes
$2,716
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Pricing History
DatePricePrice ChangeDescription
8/19/2026$6,150,000 Listed Price

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59 Hagerty Drive, Tisbury, MA, 02568 is a Single Family Home for sale at $6,150,000 with 5,034 sqft and a lot size of 1.15. 59 Hagerty Drive has 6 bedrooms, 5.2 baths, and was built in 2003. The property's zip code is 02568 which is in Tisbury, MA