59 Hagerty Drive, Tisbury, MA 02568 (MLS # 73565263)
Twitter
Facebook
Email
|
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.
| LAST UPDATED | 8/18/2026 | YEAR BUILT | 2003 |
|---|---|---|---|
| GARAGE SPACES | 2.0 | COUNTY | Dukes |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Zoned |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Water Heater |
| BASEMENT | Full, Partially Finished, Yes |
| GARAGE | Yes |
| HEAT | Forced Air, Propane, Zoned |
| LOT | 1.15 acre(s) |
| LOT DESCRIPTION | Gentle Sloping |
| PARKING | Attached, Off Street, Garage |
| SEWER | Private Sewer |
| STYLE | Other |
| TAXES | 32594 |
| VIEW | Yes |
| VIEW DESCRIPTION | Water, Scenic |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
0
P
I
*Estimate only
| SATELLITE VIEW |
| / | |
We respect your online privacy and will never spam you. By submitting this form with your telephone number
you are consenting for Jessica
Larsen to contact you even if your name is on a Federal or State
"Do not call List".
Listing provided by Carol Shore, Donnelly + Co.
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
This IDX solution is (c) Diverse Solutions 2026.