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Susan Lelansky
REALTOR®
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59 Hagerty Drive, Tisbury, MA 02568

$6,150,000
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BEDS6 BATHS5 full 2 partial SQUARE FEET5,034 MLS#73565263
STATUSActive PROPERTY TYPEResidential - Single Family

Property 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.

59 Hagerty Drive | MLS# 73565263

This single family home located at 59 Hagerty Drive, Tisbury, MA 02568 is currently listed for sale with an asking price of $6,150,000. This property was built in 2003 and has 6 bedrooms and 5 full and 2 partial baths with 5034 sq. ft. Search Tisbury real estate on susanlelansky.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Partially Finished
Cooling: Central Air
Garage: 2 car attached
Heating: Forced Air, Propane
Lot Size: 1.15 Acres
Taxes: $32,594
Year Built: 2003

Feature Descriptions

Appliances: Water Heater
Building Area Total: 5034
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 26
GarageY/N: Yes
HeatingY/N: 1
Lot Features: Gentle Sloping
Parcel Number: 2451324
Parking Features: Attached, Off Street
Parking Total: 8
Rooms Total: 14
Sewer: Private Sewer
Special View Info: Scenic View(s)
Water: Public
Waterfront Features: Sound,1/2 to 1 Mile To Beach, Beach Ownership(Public)

Listed By / Shown By

Listed By

Agency Name: Donnelly + Co.
Agent Name: Carol Shore
Agency Phone: 508-627-1022

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Estimated Payment

$ 18,197.15 per month $13,687.23 Principal & Interest $2,716.17 Property Tax $1,793.75 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 09/14/2026. The listing information on this page last changed on 09/14/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 09/14/2026 12:00:26 AM EST) or MLSPIN MLS (last updated Sun 09/13/2026 11:38:26 PM EST) or Prime MLS (last updated Sun 09/13/2026 11:33:22 PM EST) or MREIS (last updated Sun 09/13/2026 11:55:17 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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