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

365 Middle Rd
Chilmark, MA 02535

  • 5 Beds
  • 3 Baths
  • 3,283 sqft (on 2 acres)

$5,239,900

Trulia Estimate
as of Aug 25, 2026

$5,239,900

Trulia Estimate
as of Aug 25, 2026
5 Beds
3 Baths
3,283 sqft
(on 2 acres)

Home Value

Trulia Estimate
$5.24M
Since last month
Increased$68K (+1.3%)
Since last year
Increased$247K (+5%)
Since last sale
Increased$3M (+123%)
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 +113% in the last 10 years
MonthEstimated value
2026
August 2026$5.24M
July 2026$5.17M
June 2026$5.26M
May 2026$5.17M
April 2026$5.15M
March 2026$5.16M
February 2026$5.09M
January 2026$5.08M
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
31 N Slope Ln, Chilmark, MA
0.90
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
18 Homeward Way, Chilmark, MA
0.81
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
6 Tabor Hls, Chilmark, MA
1.32
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
3 Fulling Mill Rd, Chilmark, MA
0.89
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
25 Osprey Ln, Chilmark, MA
1.20
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
49 Gosnolds Way, Chilmark, MA
1.36
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
10 Mollys Way, Chilmark, MA
1.27
Single-Family Home
$2,550,000
10/02/25
3
2
1,524
94 Menemsha Inn Rd, Chilmark, MA
1.47
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
9 Beetlebung Grove Way, Chilmark, MA
2.13
Single-Family Home
$2,225,000
10/24/25
4
3
2,968
20 Eliot Ave, Chilmark, MA
1.95
Single-Family Home
$6,550,000
11/14/25
4
3.5
3,355

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
1 Pond Mark, Chilmark, MA 02535
0.05
$4,050,500
3
2.5
1,316
Off Market
High Mark, Chilmark, MA 02535
0.14
$1,900,000
-
-
-
For Sale
391 Middle Rd, Chilmark, MA 02535
0.27
$6,281,000
6
4.5
3,859
Off Market
493 South Rd, Chilmark, MA 02535
0.38
-
-
-
-
Off Market
18 Allen Farm Rd, Chilmark, MA 02535
0.72
$2,250,000
1
1
726
For Sale
18 Homeward Way, Chilmark, MA 02535
0.81
$4,325,000
5
2.5
3,885
Recently Sold
43 N Slope Ln, Chilmark, MA 02535
0.82
$1,699,999
3
2
1,540
For Sale
3 Fulling Mill Rd, Chilmark, MA 02535
0.89
$1,775,000
3
2
1,728
Recently Sold
31 N Slope Ln, Chilmark, MA 02535
0.90
$2,537,800
4
3.5
2,300
Off Market
25 Fulling Mill Rd, Chilmark, MA 02535
0.90
$2,250,000
4
3
1,918
For Sale
21 & 25 Fulling Mill Rd, Chilmark, MA 02535
0.90
$2,250,000
4
3
1,918
For Sale
44 Cencelle St, Chilmark, MA 02535
0.93
$4,975,000
4
3
3,432
For Sale

Local Information

  • Map ViewExplore the area around 365 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
1880
Lot Size
2 acres
Living Area
3,283 sqft
Price/Sqft
$1,596

About this House

Enjoy the spectacular Atlantic Ocean views across the protected 31 acre Keith Farm from this 1880 Antique Farm House, Barn & Bunk House. 2.2 beautifully landscaped acres with perennial gardens, fruit trees and walking paths over to the the large post & beam barn which serves as the compounds guest house complete with kitchen, bath and private deck. Slide open the barn doors to take in more pasture & sea views. A wonderful Middle Road location walking distance to Beetlebung Corner and minutes to Lucy Vincent Beach.
365 Middle Rd, Chilmark, MA 02535 is a 5 bedroom, 3 bathroom, 3,283 sqft single-family home built in 1880. It last sold for $2,350,000 on Oct 9, 2015. It is currently off market. The Trulia Estimate is $5,239,900, with a rent estimate of $7,636/month.

Home Details for 365 Middle Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 12Types of Rooms: Dining Room, Family Room, Mud Room
Appliances & Utilities
Cable ReadyDishwasherRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherGardenLawnPatioPorchSprinkler System

Property Information

Year Built
Year Built: 1880
Property Type / Style
Property Type: Single Family HomeArchitecture: conventional

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Oct 9, 2015
Source: LINK #28710
Sold
$2,350,000
May 15, 2006
Source: LINK #9479
Sold
$2,050,000

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!!"
    0
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Frequently asked questions about 365 Middle Rd

  • What is 365 Middle Rd estimated to be worth?
    Trulia's estimated value for 365 Middle Rd in Chilmark, MA is $5,239,900.
  • What is the price history for 365 Middle Rd?
    365 Middle Rd in Chilmark, MA last sold for $2,350,000 in October 2015.
  • 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 365 Middle Rd?
    The closest schools to 365 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).
  • How big is the lot at 365 Middle Rd?
    The lot at 365 Middle Rd in Chilmark, MA is about 2.2 acres.

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