365 Middle Rd, Chilmark, MA 02535
OFF MARKET

365 Middle Rd
Chilmark, MA 02535

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

$5,279,000

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $28,664/mo*

$5,279,000

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $28,664/mo*
5 Beds
3 Baths
3,283 sqft
(on 2 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 365 Middle Rd

DatePriceEventSource
10/09/2015$2,350,000Sold
LINK #28710
05/15/2006$2,050,000Sold
LINK #9479
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Property Tax and Assessment

Year2025
Tax$13,663
Assessment$6,072,500
Home facts updated by county records

Comparable Sales for 365 Middle Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.90
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
0.81
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
1.32
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
0.89
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
1.56
Single-Family Home
$1,607,000
07/10/25
4
3
2,850
1.20
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
1.35
Single-Family Home
$3,100,000
07/03/25
6
3
1,500
1.06
Single-Family Home
$1,050,000
05/29/25
4
2
1,701
1.40
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
1.27
Single-Family Home
$2,550,000
10/02/25
3
2
1,524

Nearby homes

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Assigned Schools

These are the assigned schools for 365 Middle Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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!!"

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 365 Middle Rd

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Off Market Homes Near 365 Middle Rd

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Homes for rent near 365 Middle Rd

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365 Middle Rd, Chilmark, MA 02535 is a 5 bedroom, 3 bathroom, 3,283 sqft single-family home built in 1880. This property is not currently available for sale. 365 Middle Rd was last sold on Oct 9, 2015 for $2,350,000. The current Trulia Estimate for 365 Middle Rd is $5,279,000.