59 Hagerty Drive, Tisbury MA 02568
Tisbury, MA 02568
$6,150,000
Est. $34,014/month
Track this home for price, status, and open-house alerts.
About this home
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.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
BMN Estimate
Get the number an algorithm can't give you
A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.
Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Aug 19, 2026
$6,150,000
Original listing
Agent: Carol Shore
Office: Donnelly + Co.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/19/2026 | 🏠 Listed for Sale | $6,150,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $32,594 | $4,392,700 |
Financial Details
Annual Property Tax
$32,594
Tax Year 2026
Assessed Value
$4,392,700
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
2003
Living Area
5,034 sq ft
Lot Size
1.15 acres
Bedrooms
6
Full Baths
5
Half Baths
2
Total Rooms
14
Interior
Heating
Forced Air, Propane
Cooling
Central Air
Flooring
None
Appliances
Water Heater
Fireplace
None
Basement
Full, Partially Finished
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Other (see Remarks)
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Off Street
Total Spaces
8
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$32,594
Assessed Value
$4,392,700
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Dukes
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2003
Bedrooms
6
Full Bathrooms
5
Half Bathrooms
2
Living Area
5,034 sq ft
Total Rooms
14
Floor Layout
Interactive room guide
Floor Layout
Finished Area
5,034 sq ft above grade
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Water Heater
Interior Features:
Windows:
Basement:
Full, Partially Finished
Laundry:
Security:
Construction & Materials
Style:
Other (See Remarks)
Year Built:
2003
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Forced Air, Propane
Heating Zones:
5
Cooling:
Central Air
Cooling Zones:
5
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Gentle Sloping
Road Surface:
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
8
Parking Features:
Attached, Off Street
Special Features
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Nearby Schools
School District
Martha's Vineyard School District local
School Safety
2024-25
5.0%
Above Average
5.0%
Suspensions
1.3%
In-School
0.5% below state avg
Elementary Schools
3 schools
Vineyard Montessori School
0.9 mi
Grades PK-08
C+
Tisbury Elementary School
1.5 mi
|
#239 of 352
|
Score: 37.3
Dropped 104 spots from last year
-20.9 below state avg
312 students
Diverse
Diverse Student Body
Grades PK-08
A-
Oak Bluffs Elementary School
2.9 mi
|
#105 of 352
|
Score: 49.0
Improved 16 spots from last year
-9.2 below state avg
402 students
Diverse
Grades PK-08
High Schools
1 school
A-
Martha's Vineyard Regional High School
4.1 mi
|
#95 of 346
|
Score: 60.5
Improved 49 spots from last year
+2.3 above state avg
744 students
Diverse
19 sports
• 1,209 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades 09-12
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$2,716
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
Loading map...
Neighborhood
59 Hagerty Drive, Tisbury MA 02568
Tisbury, MA 02568
Listing Information
Listing Agent
Carol Shore
Listing Office
Donnelly + Co.
Office Phone
508-627-1022
Agent MLS ID
CN238163
Office MLS ID
AN6036
Listing Data Updated
Aug 18, 2026 8:33 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
Contact Us
Ask about this property — free, no obligation.
Similar Homes for Sale
Comparable Properties
Customize Comparable Search
Finding comparable properties...
Loading market insights for Tisbury.