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59 Hagerty Drive, Vineyard Haven

$6,150,000

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.

HIGHLIGHTS

Link ID 44845
Bedrooms 6
Baths 5
Half Baths 2
Rooms 14
Living Space 5034
Acreage 1.15
Waterview
Yes

FEATURES AND AMENITIES

Link ID
44845
Price
$6,150,000
Baths
5
Half Baths
2
Rooms
14
Living Space
5034
Acreage
1.15
Zoning
R50
Water
Town
Sewer
Septic Tank
Heat
GFHA
2026 Tax Assessment
$4,392,700
Building Assessment
$3,436,100
Land Assessment
$956,600
Estimated Taxes
$32,594
Outdoor Spaces
Water Views
Deck
Garden
Patio
Porch
Porch - Screened
Private Pool
Gym
Beach Access - Public
Hot Tub
Year Built
2003
Fireplaces
None
Flooring
Hardwood, Tile and Carpet
Listing Broker
Donnelly + Co

59 Hagerty Drive, Vineyard Haven

Copyright 2026 LINK MV. All rights reserved. Information deemed reliable but is not guaranteed.
Buyer note, 2% Land Bank fee.
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