391 Middle Rd, Chilmark, MA 02535
OFF MARKET

391 Middle Rd
Chilmark, MA 02535

  • 6 Beds
  • 4.5 Baths
  • 3,859 sqft (on 3.30 acres)

$6,355,700

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $33,897/mo*

$6,355,700

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $33,897/mo*
6 Beds
4.5 Baths
3,859 sqft
(on 3.30 acres)

Local Information

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

Description

This iconic property and location is truly a once-in-a-lifetime opportunity. Exceptional house and guest house that is ready to move into . The exterior resonates with what is beloved about Chilmark but the interior is contemporary and fresh. The main house has views overlooking the Keith farm and the Atlantic Ocean beyond, old stone walls and open meadows. A new owner will have the gratification of the three existing structures already built. Designed and built by two well-known craftsmen, the owners spared no expense on the renovation of the main house and the new post and beam guest house and barn. The open floor plan of the living, state-of-the-art kitchen, and dining room has southern-facing views over the Keith Farm and Atlantic Ocean. There is a first-floor primary bedroom with ocean and farm views as well as a private office. The second floor has a second primary suite with views and two additional bedrooms that share a full bath. Stone patios are lined with vibrant perennial gardens and old stonewalls including glacial boulders that line the property boundaries. In addition to the main house, there is a privately-sited custom post and beam guest house with two bedrooms, an open kitchen living space, and a full bath. Fir floors and trim throughout this cottage, oversized windows, and high ceilings. There is a sweet garage off of Middle Road as well as a shed at the top of the driveway for bikes and beach equipment. The owners added a beautiful Amish framed barn for kayaks, car, boat or potential party barn. This location lends itself to easy living in the heart of Chilmark. Walk to the Chilmark Community Center, the Chilmark Store, the Tavern, the library, and the fabulous Beetlebung Farm Stand.
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. This description is from October 24, 2024

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 391 Middle Rd

Interior Features

Interior Details
Basement: yes partial full basement with systems and storageNumber of Rooms: 11
Beds & Baths
Number of Bedrooms: 6Main Level Bedrooms: 1Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3859 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: 5 burner Wolf with double ovens, Washer: yes
Heating & Cooling
Heating: GFHANo CoolingHas HeatingHeating Fuel: GFHA
Fireplace & Spa
Fireplace: yes
Windows, Doors, Floors & Walls
Flooring: fir floors
Levels, Entrance, & Accessibility
Floors: Fir Floors
View
Has a ViewView: Pasture

Exterior Features

Exterior Home Features
Other Structures: Guest house 800 sq ft, barn is generous 27'9" by 14' with a loft that is 9'3" by 14', garage and storage shedExterior: WViews, Garden, Patio, Porch, PubBchFoundation: yes partial full basementGarden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Yes plenty
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1941Year Renovated: 2018
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Usage of Home: 688

Price & Status

Price
List Price: $6,485,000

Active Status

MLS Status: S

Location

Direction & Address
City: Chilmark

Building

Building Area
Building Area: 3859 Square Feet

Lot Information

Lot Area: 3.3 Acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 42440
Last check for updates: about 19 hours ago
Listed by Jill Hobby Napior 508-642-0831
Tea Lane Associates
Bought with: Meg Bodnar 508-221-2782, Tea Lane Associates
Source: LINK, MLS#42440

Price History for 391 Middle Rd

DatePriceEventSource
10/16/2024$6,100,000Sold
LINK #42440
09/28/2024$6,485,000PendingLINK #42440
09/10/2024$6,485,000PriceChange
LINK #42440
08/21/2024$6,950,000Listed For SaleLINK #42440
11/05/1998$1,400,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$12,396
Assessment$5,509,400
Home facts updated by county records

Comparable Sales for 391 Middle Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1.33
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
1.00
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
1.13
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
1.52
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
1.57
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
1.23
Single-Family Home
$3,100,000
07/03/25
6
3
1,500
1.59
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
1.68
Single-Family Home
$6,550,000
11/14/25
4
3.5
3,355
2.11
Single-Family Home
$5,900,000
10/31/25
6
4.5
3,143
1.16
Single-Family Home
$1,775,000
11/07/25
3
2
1,728

Nearby homes

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Assigned Schools

These are the assigned schools for 391 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!!"

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Apartments for Rent

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Homes for sale near 391 Middle Rd

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Off Market Homes Near 391 Middle Rd

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© 2026 LINK, All Rights Reserved. Data last updated: 2026-06-01 10:07:37 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Homes for rent near 391 Middle Rd

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391 Middle Rd, Chilmark, MA 02535 is a 6 bedroom, 5 bathroom, 3,859 sqft single-family home built in 1941. This property is not currently available for sale. 391 Middle Rd was last sold on Oct 16, 2024 for $6,100,000 (6% lower than the asking price of $6,485,000). The current Trulia Estimate for 391 Middle Rd is $6,355,700.