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Listing broker remarks

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.— Donnelly + Co.

Key details

  • 5,034 sq ft
  • 1.15 acres
  • 6 beds
  • 5 baths
  • 2003 built
  • $1,221 / sq ft
  • $32,594 2026 taxes
MLS #
7⁠3⁠5⁠6⁠5⁠2⁠6⁠3⁠
Last updated
Address
59 Hagerty Drive
Town
Tisbury, MA
ZIP
02568
Deed (Bk/Pg)
1651 / 958

Map

Neighborhood: Tisbury

National Historic Landmark

Federally designated as nationally significant — the highest U.S. historic recognition. Section 106 review applies to federal undertakings affecting the property.

National Register

Listed on the National Register of Historic Places. Owners may qualify for the 20% federal Historic Rehabilitation Tax Credit on certified rehabilitation work.

State Register

Listed on the Massachusetts State Register of Historic Places.

Local Historic District

Inside a Local Historic District. Exterior changes visible from a public way require approval from the local historic district commission.

Local Landmark

Individually designated by the town as a local landmark. Exterior alterations require commission approval.

MACRIS Inventory

Documented in MACRIS, the state historic inventory. Informational only — no regulatory constraints.

Article 85 (Boston)

Subject to Boston Article 85 demolition-delay review, which can pause demolition of buildings 50+ years old for up to 90 days.

Ch. 91 Waterways License

An active MassDEP permit for a dock, pier, seawall, or other structure on or over a Massachusetts waterway. Many older licenses are not digitized; this record is provided for reference only.

Massachusetts Great Pond

A Great Pond under M.G.L. Ch. 91 — the Commonwealth retains public rights to fish and navigate these state-designated waters. Private docks and other waterfront structures require a Waterways License from MassDEP.

Likely Great Pond

The MLS listing describes this property as being on a Great Pond, which would be a state-designated water body under M.G.L. Ch. 91. GIS data did not independently confirm the pond name — verification needed.