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

$5,821,100

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

53 Wequobsque Rd, Chilmark, MA 02535

Est. Refi. Payment $33,670/mo*
Refinance Your Home
Currently Off Market - Sold Sep 9, 2021 for $3,290,000

Home Value

Trulia Estimate
$5.82M
Since last month
Increased$4K (+0.1%)
Since last year
Increased$352K (+6.4%)
Since last sale
Increased$3M (+78.7%)
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 +76% in the last 10 years
MonthEstimated value
2026
October 2026$5.88M
September 2026$5.87M
August 2026$5.83M
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
21 Eliot Avenue, Chilmark, MA
0.96
Single-Family Home
$5,250,000
09/03/26
4
3
2,746
11 Greenhouse Ln, Chilmark, MA
1.10
Single-Family Home
$3,550,000
10/02/26
3
2
1,562
18 Homeward Way, Chilmark, MA
1.86
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
6 Trails End, Chilmark, MA
1.86
Single-Family Home
$2,700,000
09/16/26
4
3
2,346
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
308 South Road, Chilmark, MA
2.15
Single-Family Home
$6,500,000
09/18/26
4
4.5
3,490

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
49 Wequobsque Rd, Chilmark, MA 02535
0.05
$4,953,400
3
4
2,100
Off Market
57 Wequobsque Rd, Chilmark, MA 02535
0.06
-
7
6
3,656
Off Market
Wequobsque Rd, Chilmark, MA 02535
0.10
-
-
-
-
Off Market
Wequobsque Rd, Chilmark, MA 02535
0.10
-
-
-
-
Off Market
45 Wequobsque Rd, Chilmark, MA 02535
0.10
$7,921,900
3
3
3,157
Off Market
25 Wequobsque Rd, Chilmark, MA 02535
0.12
-
-
-
-
Off Market
0 Wequobsque, Chilmark, MA 02535
0.13
-
-
-
-
Off Market
Wequobsque Rd, Chilmark, MA 02535
0.14
-
-
-
-
Off Market
41 Wequobsque Rd, Chilmark, MA 02535
0.17
$6,171,800
2
1
896
Off Market
39 Wequobsque Rd, Chilmark, MA 02535
0.19
$3,007,300
3
3
1,872
Off Market
74 Wequobsque Rd, Chilmark, MA 02535
0.20
-
7
4
4,096
Off Market
15 Periwinkle Ln, Chilmark, MA 02535
0.23
$1,936,100
4
3
1,192
Off Market
35 Wequobsque Rd, Chilmark, MA 02535
0.24
$3,084,000
4
3.5
2,313
Off Market
62 Stonewall Rd, Chilmark, MA 02535
0.26
$5,428,700
4
3
3,877
Off Market
58 Stonewall Rd, Chilmark, MA 02535
0.29
$1,573,400
5
1
1,518
Off Market
14 Rumpus Ridge Rd, Chilmark, MA 02535
0.30
$2,002,400
4
2
1,764
Off Market
9 Periwinkle Ln, Chilmark, MA 02535
0.31
$4,378,900
6
4
3,763
Off Market
18 Wequobsque Rd, Chilmark, MA 02535
0.32
-
2
2
2,836
Off Market
52 Stonewall Rd, Chilmark, MA 02535
0.32
$5,130,500
6
4
3,551
Off Market
11 Wequobsque Rd, Chilmark, MA 02535
0.34
-
-
-
-
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

Single-Family Home
Built in 1998
6.5 acre lot
4,237 sqft
$1,374/sqft

About this House

What's unique:South shoreLarge one car garagePing-pong tableDramatic wequobsque cliffsLarge gathering kitchenHalf bath
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,821,100.

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 September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
8MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Chilmark

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 100% say there are community events
  • 78% say neighbors are friendly
  • 43% say there's holiday spirit
Trulia Trick or TreatStart Ghost Hunt
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!!"
    0
    Flag

LGBTQ Local Legal Protections

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 $5,821,100.
  • 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.

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 53 Wequobsque Rd

Skip to last item
Skip to first item

Homes for sale near 53 Wequobsque Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item