252 Middle Rd, Chilmark, MA 02535
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Property image
OFF MARKET

252 Middle Rd
Chilmark, MA 02535

  • 3 Beds
  • 1.5 Baths
  • 1,224 sqft (on 1.30 acres)

$1,611,400

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $8,860/mo*
Refinance Your Home

$1,611,400

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $8,860/mo*
Refinance Your Home
3 Beds
1.5 Baths
1,224 sqft
(on 1.30 acres)

Home Value

Trulia Estimate
$1.61M
Since last month
Decreased$18K (-1.1%)
Since last year
Increased$71K (+4.6%)
Since last sale
Increased$557K (+53.1%)
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 +48% in the last 10 years
MonthEstimated value
2026
August 2026$1.6M
July 2026$1.62M
June 2026$1.65M
May 2026$1.63M
April 2026$1.61M
March 2026$1.59M
February 2026$1.57M
January 2026$1.57M
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
3 Fulling Mill Rd, Chilmark, MA
0.16
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
6 Tabor Hls, Chilmark, MA
0.32
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
31 N Slope Ln, Chilmark, MA
0.91
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
9 Beetlebung Grove Way, Chilmark, MA
1.41
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
25 Osprey Ln, Chilmark, MA
1.01
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
18 Homeward Way, Chilmark, MA
1.02
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
60 Meeting House Rd, Chilmark, MA
0.95
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
15 Old Farm Rd, Chilmark, MA
1.72
Single-Family Home
$3,710,000
03/12/26
3
5
3,171
10 Mollys Way, Chilmark, MA
2.17
Single-Family Home
$2,550,000
10/02/25
3
2
1,524
49 Gosnolds Way, Chilmark, MA
1.44
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044

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
3 Fulling Mill Rd, Chilmark, MA 02535
0.16
$1,775,000
3
2
1,728
Recently Sold
Cencelle, Chilmark, MA 02535
0.19
$1,275,000
-
-
-
For Sale
44 Cencelle St, Chilmark, MA 02535
0.26
$4,975,000
4
3
3,432
For Sale
6 Tabor Hls, Chilmark, MA 02535
0.33
$2,100,000
4
3
2,544
Recently Sold
21 & 25 Fulling Mill Rd, Chilmark, MA 02535
0.31
$2,250,000
4
3
1,918
For Sale
25 Fulling Mill Rd, Chilmark, MA 02535
0.31
$2,250,000
4
3
1,918
For Sale
31 Cross Rip Ln, Chilmark, MA 02535
0.58
$1,090,400
1
1
512
Off Market
27 Ocean View Farm Rd, Chilmark, MA 02535
0.57
$3,003,400
4
3
2,450
Off Market
22 Ocean View Farm Rd #B, Chilmark, MA 02535
0.64
$1,176,700
2
1.5
1,520
Off Market
18 Allen Farm Rd, Chilmark, MA 02535
0.66
$2,250,000
1
1
726
For Sale
174 Middle Road, Chilmark, MA 02535
0.74
$1,695,000
3
3
3,702
For Sale
34 Ebens Lane, Chilmark, MA 02535
0.78
$2,725,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 252 Middle 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
1973
Lot Size
1.3 acres
Living Area
1,224 sqft
Price/Sqft
$1,317

About this House

Charming two cottage Chilmark retreat tucked away on Middle Road. Nestled into a rolling hill, the main structure overlooks the quintessential up-island setting: a lower pasture lined with ancient stone walls and mature trees. Completing the main house is a first-floor ensuite master, two additional bedrooms, a dramatic wall of windows, and a sizable deck perfect for summer evenings. The separate one-bedroom guest house offers an idyllic, private refuge with a wood-burning fireplace, ample natural light, and a bonus sleeping loft. Situated on 1.3 acres, this property is in close proximity to all that Chilmark offers- Lucy Vincent Beach, Squibnocket, Chilmark General Store, and an abundance of scenic hiking trails. Renovations have just begun to refurbish this 1973 cottage, making it an excellent opportunity for a buyer to perfect their up-island sanctuary.
252 Middle Rd, Chilmark, MA 02535 is a 3 bedroom, 2 bathroom, 1,224 sqft single-family home built in 1973. It last sold for $1,047,500 on Jan 7, 2021. More recently, it was listed as a rental in March 2018 with an asking price of $3,750 per month. That rental listing was removed on March 25, 2018. It is currently off market. The Trulia Estimate is $1,611,400, with a rent estimate of $5,018/month.

Home Details for 252 Middle Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Interior Details
Number of Rooms: 6
Appliances & Utilities
DryerWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
Exterior: Other
Parking & Garage
Parking: Off Street

Community

Units in Building: 1

Lot Information

Lot Area: 1.30 acres

Price and Tax history

DateEventPrice
Jan 7, 2021
Source: LINK #37589
Sold
$1,047,500
Nov 30, 2020
Source: Agent Provided
Listed For Sale
$1,135,000
Oct 22, 2020
Source: LINK #35294
Sold
$975,000
Aug 5, 2020
Source: Agent Provided
Listed For Sale
$1,060,000
Dec 3, 2019
Source: Agent Provided
ListingRemoved
$1,060,000

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

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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Frequently asked questions about 252 Middle Rd

  • What is 252 Middle Rd estimated to be worth?
    Trulia's estimated value for 252 Middle Rd in Chilmark, MA is $1,611,400.
  • What is the price history for 252 Middle Rd?
    252 Middle Rd in Chilmark, MA last sold for $1,047,500 in January 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 252 Middle Rd?
    The closest schools to 252 Middle 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 252 Middle Rd have laundry facilities?
    Yes, 252 Middle Rd in Chilmark, MA has in-unit laundry.
  • How big is the lot at 252 Middle Rd?
    The lot at 252 Middle Rd in Chilmark, MA is about 1.3 acres.

Apartments for Rent

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Off Market Homes Near 252 Middle Rd

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