53 Wequobsque Rd, Chilmark, MA 02535
Property image
Property image
OFF MARKET

53 Wequobsque Rd
Chilmark, MA 02535

  • 5 Beds
  • 4.5 Baths
  • 4,237 sqft (on 6.50 acres)

$5,694,600

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $31,513/mo*
Refinance Your Home

$5,694,600

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $31,513/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,237 sqft
(on 6.50 acres)

Home Value

Trulia Estimate
$5.7M
Since last month
Decreased$125K (-2.2%)
Since last year
Increased$162K (+2.9%)
Since last sale
Increased$2M (+71.7%)
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 +64% in the last 10 years
MonthEstimated value
2026
August 2026$5.65M
July 2026$5.69M
June 2026$5.77M
May 2026$5.73M
April 2026$5.66M
March 2026$5.73M
February 2026$5.62M
January 2026$5.59M
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
12 Squibnocket Rd, Chilmark, MA
1.38
Single-Family Home
$5,900,000
10/31/25
6
4.5
3,143
20 Eliot Ave, Chilmark, MA
0.94
Single-Family Home
$6,550,000
11/14/25
4
3.5
3,355
25 Osprey Ln, Chilmark, MA
1.61
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
18 Homeward Way, Chilmark, MA
1.86
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
31 N Slope Ln, Chilmark, MA
1.98
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
94 Menemsha Inn Rd, Chilmark, MA
2.23
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
49 Gosnolds Way, Chilmark, MA
2.36
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
23 Chockers Ln, Chilmark, MA
1.54
Single-Family Home
$5,750,000
04/10/26
2
1.5
1,446
51 Squibnocket Farm Rd, Chilmark, MA
2.02
Single-Family Home
$10,500,000
03/12/26
4
2.5
3,200
10 Mollys Way, Chilmark, MA
1.51
Single-Family Home
$2,550,000
10/02/25
3
2
1,524

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
8 Rumpus Ridge Rd, Chilmark, MA 02535
0.38
$1,550,000
4
2
1,757
For Sale
10 Rumpus Ridge Rd, Chilmark, MA 02535
0.38
$1,080,100
4
2
1,701
Off Market
61 Stonewall Road, Chilmark, MA 02535
0.40
$5,100,000
5
4
3,513
For Sale
76 State Rd, Chilmark, MA 02535
0.53
$1,897,000
4
2
3,093
Off Market
32 Stonewall Rd, Chilmark, MA 02535
0.54
-
-
-
-
Off Market
10 Abels Neck Rd, Chilmark, MA 02535
0.60
$1,450,000
3
2
1,749
For Sale
493 South Rd, Chilmark, MA 02535
0.80
-
-
-
-
Off Market
391 Middle Rd, Chilmark, MA 02535
0.86
$6,214,200
6
4.5
3,859
Off Market
Eliot Ave, Chilmark, MA 02535
0.93
-
-
-
-
Off Market
131 State Rd, Chilmark, MA 02535
0.93
$3,950,000
3
2
1,260
For Sale
20 Eliot Ave, Chilmark, MA 02535
0.94
$6,550,000
4
3.5
3,355
Recently Sold
1 Pond Mark, Chilmark, MA 02535
1.06
$4,025,000
3
2.5
1,316
Off Market

Local Information

  • Map ViewExplore the area around 53 Wequobsque Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1998
Lot Size
6.5 acres
Living Area
4,237 sqft
Price/Sqft
$1,344

About this House

Waterfront in Chilmark with Private Ocean Beach. This home on 6 acres nestled atop the magnificent Wequobsque Cliffs on Chilmark's south shore was built by one of the island's finest builders, John Early Construction. The home enjoys views of the Atlantic Ocean and private ownership of over 300 ft of white sand beach (Note: Seller is installing beach stairs which will be complete by the start of the summer season). There are 5 bedrooms spread over 4000 square feet with several separate living spaces including the ''party barn'' that makes up the west wing of the property. Look no further if your dream is to own a home waterfront on Chilmark's south shore.
53 Wequobsque Rd, Chilmark, MA 02535 is a 5 bedroom, 5 bathroom, 4,237 sqft single-family home built in 1998. It last sold for $3,290,000 on Sep 9, 2021. It is currently off market. The Trulia Estimate is $5,694,600, with a rent estimate of $7,606/month.

Home Details for 53 Wequobsque Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood

Property Information

Year Built
Year Built: 1998Year Updated: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 6.50 acres

Price and Tax history

DateEventPrice
Jul 29, 2022
Source: LINK #39258
ListingRemoved
$4,500,000
Jul 5, 2022
Source: LINK #39258
PriceChange
$4,500,000
Price decreased by 8%
Feb 11, 2022
Source: LINK #39258
Listed For Sale
$4,900,000
Sep 9, 2021
Source: LINK #38565
Sold
$3,290,000
May 22, 2021
Source: Martha's Vineyard MLS #32100178
Listed For Sale
$4,250,000

Market trends in Chilmark

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
8MoM
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Around this home

What Locals Say about Chilmark

At least 2 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 100 % Say there are community events

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 78 % Say neighbors are friendly

  • 75 % Say it's dog friendly

  • 75 % Say people would walk alone at night

  • 67 % Say parking is easy

  • 67 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 43 % Say there's holiday spirit

  • 33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Elaine V.
    "I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"
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Apartments for Rent

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Homes for sale near 53 Wequobsque Rd

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Off Market Homes Near 53 Wequobsque Rd

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Frequently asked questions about 53 Wequobsque Rd

  • What is 53 Wequobsque Rd estimated to be worth?
    Trulia's estimated value for 53 Wequobsque Rd in Chilmark, MA is $5,694,600.
  • What is the price history for 53 Wequobsque Rd?
    53 Wequobsque Rd in Chilmark, MA last sold for $3,290,000 in September 2021.
  • Is Chilmark a buyer's or seller's market?
    Chilmark is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 53 Wequobsque Rd?
    The closest schools to 53 Wequobsque Rd in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
  • Does 53 Wequobsque Rd have air conditioning?
    Yes, 53 Wequobsque Rd in Chilmark, MA has air conditioning.
  • How big is the lot at 53 Wequobsque Rd?
    The lot at 53 Wequobsque Rd in Chilmark, MA is about 6.5 acres.