$6,150,000
6 Beds
6 Baths
5,034 sqft (on 1.15 acres)
59 Hagerty Dr, Tisbury, MA 02568
Est. Mortgage $33,833/mo*
Get Pre-QualifiedWe estimate this home will sell faster than 84% nearby.
Home Highlights
Single-Family Home
Built in 2003
1.15 acre lot
$1,222/sqft
Local Information
- Map ViewExplore the area around 59 Hagerty Dr.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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.
Last check for updates: about 8 hours ago
Listing courtesy of Carol Shore
Donnelly + Co
We estimate this home will sell faster than 84% nearby.
Home Details for 59 Hagerty Dr
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Interior Details Basement: Full - UnfinishedNumber of Rooms: 14 |
Beds & Baths Number of Bedrooms: 6Main Level Bedrooms: 1Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 5034 Square Feet |
Appliances & Utilities Utilities: NoneAppliances: Stove: Viking (Main House)/KitchenAid (Garage Apartment), Washer: Maytag (Main House)/LG (Garage Apartment) |
Heating & Cooling Heating: GFHANo CoolingHas HeatingHeating Fuel: GFHA |
Windows, Doors, Floors & Walls Flooring: Hardwood, Tile and Carpet |
Levels, Entrance, & Accessibility Floors: Hardwood, Tile And Carpet |
View Has a ViewView: D/Snd, Trees/Woods |
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Exterior Home Features Exterior: WViews, Deck, Garden, Patio, Porch, ScrPorch, P/Pool, Gym, PubBch, H/TubFoundation: Poured ConcreteGarden |
Parking & Garage No CarportNo GarageNo Attached GarageParking: Yes |
Frontage Frontage Type: NoneNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Days on Market: 18 |
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Year Built Year Built: 2003Year Renovated: 2021 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Property Information Parcel Number: 29D11 |
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Price List Price: $6,150,000Price Per Sqft: $1,222 |
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MLS Status: A |
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Direction & Address City: Vineyard Haven |
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Listing Agent Listing ID: 44845 |
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Building Area Building Area: 5034 Square Feet |
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Lot Area: 1.15 Acres |
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Listing Agreement Type: E |
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BasementMls Number: 44845Water ViewWater View: D/Snd |
Around this home
What Locals Say about Tisbury
At least 26 Trulia users voted on each feature.
87 % Say yards are well-kept
80 % Say it's walkable to grocery stores
78 % Say kids play outside
77 % Say people would walk alone at night
75 % Say it's quiet
72 % Say it's dog friendly
72 % Say it's walkable to restaurants
71 % Say there's holiday spirit
70 % Say there's wildlife
68 % Say car is needed
64 % Say they plan to stay for at least 5 years
63 % Say there are sidewalks
61 % Say parking is easy
53 % Say there are community events
44 % Say neighbors are friendly
39 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
Market trends in Tisbury
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
55
8MoM
Home Value
Trulia Estimate
$5.75MSince last month
Increased$935K (+19.3%)Since last year
Increased$1M (+22.7%)Since last sale
Increased$1M (+29.7%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +159% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $5.77M |
| August 2026 | $5.75M |
| July 2026 | $4.84M |
| June 2026 | $4.83M |
| May 2026 | $4.8M |
| April 2026 | $4.73M |
| March 2026 | $4.75M |
| February 2026 | $4.64M |
| January 2026 | $4.57M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $4,895,000 | 02/13/26 | 5 | 6.5 | 4,216 | |
0.14 | Single-Family Home | $4,450,000 | 02/13/26 | 5 | 5 | 4,185 | |
0.10 | Single-Family Home | $2,036,000 | 10/01/25 | 5 | 3.5 | 3,587 | |
0.08 | Single-Family Home | $2,485,000 | 04/17/26 | 6 | 3.5 | 3,000 | |
0.22 | Single-Family Home | $2,630,000 | 06/29/26 | 5 | 4 | 3,361 | |
0.68 | Single-Family Home | $3,925,000 | 09/24/25 | 8 | 4.5 | 3,954 | |
0.63 | Single-Family Home | $1,650,000 | 01/09/26 | 4 | 3.5 | 2,194 | |
0.66 | Single-Family Home | $1,910,000 | 04/03/26 | 5 | 3.5 | 3,250 | |
1.22 | Single-Family Home | $3,600,000 | 08/19/26 | 5 | 6.5 | 4,372 | |
0.94 | Single-Family Home | $2,000,000 | 05/28/26 | 4 | 3.5 | 2,690 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.06 | $1,376,200 | 3 | 1 | 1,118 | Off Market | |
0.07 | $4,895,000 | 5 | 6.5 | 4,216 | Recently Sold | |
0.07 | - | - | - | - | Off Market | |
0.07 | - | - | - | - | Off Market | |
0.08 | $2,485,000 | 6 | 3.5 | 3,000 | Recently Sold | |
0.08 | - | - | - | - | Off Market | |
0.10 | $2,085,700 | 5 | 3.5 | 3,587 | Off Market | |
0.12 | $2,681,100 | 3 | 2 | 2,064 | Off Market | |
0.13 | - | - | - | - | Off Market | |
0.12 | $1,755,400 | 3 | 2 | 1,883 | Off Market | |
0.14 | $4,450,000 | 5 | 5 | 4,185 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 18, 2026 Source: LINK #44845 | Listed For Sale | $6,150,000 |
Apr 6, 2023 Source: LINK #40483 | Sold | $4,450,000 |
Mar 15, 2023 Source: LINK #40483 | Pending | $4,450,000 |
Mar 6, 2023 Source: Martha's Vineyard MLS #32300054 | Contingent | $4,450,000 |
Mar 3, 2023 Source: LINK #40483 | Listed For Sale | $4,450,000 |
Sep 12, 2001 Source: N/A | Sold | $630,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $31,925 | $4,217,300 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Carol Shore, Donnelly + Co
© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-04 14:59:24 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.
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Frequently asked questions about 59 Hagerty Dr
- What is the estimated monthly payment for 59 Hagerty Dr?Based on a $6,150,000 list price with 20% down at today's rates, the estimated monthly payment for 59 Hagerty Dr in Tisbury, MA is approximately $35,137 (about $32,499 principal & interest, $2,563 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Tisbury?Residents describe Tisbury, MA as well-kept, walkable to grocery stores, and quiet. See homes for sale in Tisbury, MA.
- What are the closest schools to 59 Hagerty Dr?The closest schools to 59 Hagerty Dr in Tisbury, MA are Martha's Vineyard Regional High School (rated 6/10), Tisbury Elementary School (Pre-K/Middle, rated 4/10).
- What is 59 Hagerty Dr estimated to be worth?Trulia's estimated value for 59 Hagerty Dr in Tisbury, MA is $5,748,000.
- Does 59 Hagerty Dr have a pool?Yes, 59 Hagerty Dr in Tisbury, MA has a pool.
- How big is the lot at 59 Hagerty Dr?The lot at 59 Hagerty Dr in Tisbury, MA is about 1.1 acres.
59 Hagerty Dr, Tisbury, MA 02568 is a 6 bedroom, 7 bathroom, 5,034 sqft single-family home built in 2003. This property is currently available for sale and was listed by LINK on Aug 18, 2026. The MLS # for this home is MLS# 44845.