Single Family Residence at 49 Gosnolds Way, Chilmark MA 02535
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32 photos

$5,200,000

49 Gosnolds Way, Chilmark MA 02535
Chilmark, MA 02535
Listed by Bonnie Pierce
Bedrooms
5
Bathrooms
3.5
Living area
4,044 sqft
Year built
2003

About this home

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

Highlights

ViewFireplace

Property details

MLS
MLS Property Information Network
MLS #
73534187
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
132
On market date
June 11, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
1
Parking spaces
9
Lot size
9.8 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Chilmark Elementary
1.81 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
57
Student:teacher ratio
14.3:1
District
Up-Island Regional
Middle
None found nearby
High
Martha's Vineyard Regional High
8.55 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
706
Student:teacher ratio
9.3:1
District
Martha's Vineyard

Walkability

Blended score for Chilmark's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

45
Somewhat walkable
out of 100
EPA National Walkability Index
11.7 / 20 -- Above average walkable
Google Places amenity density
25 / 100
Restaurants & cafes0
Grocery stores0
Parks3
Schools0
Transit stops3
Pharmacies0

Market position

How this listing compares to current activity in Chilmark, from live MLS data.

On the market 132 days -- 909 fewer days than Chilmark's current average of 1041 days.
For reference, the median list price across 35 active listings in Chilmark right now is $50,700.

Mortgage calculator

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Est. monthly payment
$31,465/mo
$1,040,000 down
$4,160,000 loan
Principal & interest$26,982
Property tax (est.)$4,333
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 16, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.