For Sale
Single family home for sale at 59 Hagerty Dr, Vineyard Haven, MA 02568 | MLS# 73565263 | Listing updated on 2026-08-22
Photo 1 of Single family home for sale at 59 Hagerty Dr, Vineyard Haven, MA 02568 | MLS# 73565263 | Listing updated on 2026-08-22
Photo 2 of Single family home for sale at 59 Hagerty Dr, Vineyard Haven, MA 02568 | MLS# 73565263 | Listing updated on 2026-08-22
Photo 3 of Single family home for sale at 59 Hagerty Dr, Vineyard Haven, MA 02568 | MLS# 73565263 | Listing updated on 2026-08-22
Photo 4 of Single family home for sale at 59 Hagerty Dr, Vineyard Haven, MA 02568 | MLS# 73565263 | Listing updated on 2026-08-22
33+
Beds Icon

Street View

$6,150,000

Monthly Est:$30,611

  • Beds Icon6 Beds
  • Beds Icon
    7 Baths
  • Beds Icon5,034sqft

59 Hagerty Dr, Vineyard Haven, MA 02568

$30,611/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2003

  • $-- HOA

  • 1.15 acres lot

  • $1,222/sq.ft

Description

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.

  • Houzeo last checked: 12 minutes ago
  • Listing updated: August 22, 2026 at 7:05 am
  • Listing Provided by: Carol Shore (508) 221-8186 | Donnelly + Co. (508) 627-1022
  • Source: MLS Property Information Network-MA | MLS#: 73565263 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Dukes County

  • City

    Vineyard Haven

  • Neighborhood

    --

  • Year Built

    2003

  • HOA Fees

    -

  • Finished Area

    5,034 sqft

  • Lot Size

    1.15 acres lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73565263

  • MLS Status

    Active

  • Days on Market

    73

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 7

Interior

  • Cooling

    Central Air

  • Appliances

    Water Heater

  • Heating

    Forced Air, Propane

  • Sewer

    Private Sewer

Construction

  • Year Built

    Year Built: 2003

  • Home type

    Single Family Residence

  • Foundation Details

    Concrete Perimeter

  • Architectural Style

    Other (see Remarks)

Utilities & Energy

  • Basement

    Full, Partially Finished

  • Water Source

    Public

  • Parking Features

    Attached, Off Street

Other Features

  • Lot Features

    Gentle Sloping

Price History

DateEventPrice

08/19/2026

Source: mls_logoMLS Property Information Network-MA #73565263

Listed for Sale

$6,150,000

$1,222/sqft

Getting Around 59 Hagerty Dr

Bike Score®

Bike Score

Somewhat Bikeable

31/100

Walk Score®

Walk Score

Car-Dependent

6/100

Data provided by Redfin

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 31, 2026, 07:15AM. The property listing data and information, or the Images, 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, and the Images, 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, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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