Vineyard Haven, MA 02568 59 Hagerty Drive

59 Hagerty Drive Vineyard Haven, MA - Image 159 Hagerty Drive Vineyard Haven, MA - Image 259 Hagerty Drive Vineyard Haven, MA - Image 3
33 more
59 Hagerty Drive Vineyard Haven, MA - Image 459 Hagerty Drive Vineyard Haven, MA - Image 559 Hagerty Drive Vineyard Haven, MA - Image 659 Hagerty Drive Vineyard Haven, MA - Image 759 Hagerty Drive Vineyard Haven, MA - Image 859 Hagerty Drive Vineyard Haven, MA - Image 959 Hagerty Drive Vineyard Haven, MA - Image 1059 Hagerty Drive Vineyard Haven, MA - Image 1159 Hagerty Drive Vineyard Haven, MA - Image 1259 Hagerty Drive Vineyard Haven, MA - Image 1359 Hagerty Drive Vineyard Haven, MA - Image 1459 Hagerty Drive Vineyard Haven, MA - Image 1559 Hagerty Drive Vineyard Haven, MA - Image 1659 Hagerty Drive Vineyard Haven, MA - Image 1759 Hagerty Drive Vineyard Haven, MA - Image 1859 Hagerty Drive Vineyard Haven, MA - Image 1959 Hagerty Drive Vineyard Haven, MA - Image 2059 Hagerty Drive Vineyard Haven, MA - Image 2159 Hagerty Drive Vineyard Haven, MA - Image 2259 Hagerty Drive Vineyard Haven, MA - Image 2359 Hagerty Drive Vineyard Haven, MA - Image 2459 Hagerty Drive Vineyard Haven, MA - Image 2559 Hagerty Drive Vineyard Haven, MA - Image 2659 Hagerty Drive Vineyard Haven, MA - Image 2759 Hagerty Drive Vineyard Haven, MA - Image 2859 Hagerty Drive Vineyard Haven, MA - Image 2959 Hagerty Drive Vineyard Haven, MA - Image 3059 Hagerty Drive Vineyard Haven, MA - Image 3159 Hagerty Drive Vineyard Haven, MA - Image 3259 Hagerty Drive Vineyard Haven, MA - Image 3359 Hagerty Drive Vineyard Haven, MA - Image 3459 Hagerty Drive Vineyard Haven, MA - Image 3559 Hagerty Drive Vineyard Haven, MA - Image 3659 Hagerty Drive Vineyard Haven, MA - Image 37
Presented By: Carol Shore with Donnelly + Co -
  • MLS# 44845
  • 08/18/2026
  • Request Tour
  • Request Info
  • Beds • 6
  • Full/Half Baths • 5 / 2
  • SQFT • 5,034

Home Details

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. 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.
Presented By: Carol Shore with Donnelly + Co -

Interior Features for 59 Hagerty Drive

Bedrooms

Main Level Bedrooms1
Total Bedrooms6

Bathrooms

Half Baths2

Other Interior Features

BasementFull - Unfinished
Fireplace Y/NNo
FlooringHardwood, Tile and Carpet
Furnished Y/NUnfurnished
Interior AmenitiesA, AC, Ins, Irr, OSh, Floor 1: The first floor features a spacious living room, dining area, sitting area, versatile game/reading area and kitchen. The 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., Floor 2: The second floor is comprised of the primary suite with luxurious bath and two additional guest bedrooms, each with an ensuite bath. A large sun deck overlooks the pool as well as an office all with distant water views. Above the garage is a separate one-bedroom apartment with full kitchen, bath, laundry and convenient interior and exterior access. The living space in the apartment is currently being used as the sixth bedroom.

General for 59 Hagerty Drive

AppliancesStove: Viking (Main House)/KitchenAid (Garage Apartment), Washer: Maytag (Main House)/LG (Garage Apartment)
Building Area UnitsSquare Feet
CityVineyard Haven
Full Baths5
HeatingGFHA
Lot Size Square Feet50093
MLS Area1
Property SubtypeSingle Family Residence
Property Type1 Family
SewerSeptic Tank
Standard StatusActive
StatusA
Tax Annual Amount32594
Tax Assessed Value3436100
Tax Lot11
Tax Year2026
TaxOtherAnnualAssessmentAmount956600
Total Rooms14
UtilitiesNone
ViewD/Snd, Trees/Woods
Year Built2003
Year Built Effective2021
ZoningR50

Exterior for 59 Hagerty Drive

Building Area Total5034
Exterior AmenitiesWViews, Deck, Garden, Patio, Porch, ScrPorch, P/Pool, Gym, PubBch, H/Tub
Foundation DetailsPoured Concrete
Frontage TypeNone
Lot FeaturesManicured, sloped
Lot Size Acres1.15
Lot Size Area1.15
Parking FeaturesYes
Water SourceTown

Additional Details

Price History

John O'Connell

Associate Broker
Price $6,150,000
MLS#44845
List Date 08/18/2026
Property Type Single Family
Phone 617.429.5219
Request Tour
Request Info
Visit My Website

Similar Properties to 59 Hagerty Drive