$6,359,100
6 Beds
4.5 Baths
3,859 sqft (on 3.30 acres)
391 Middle Rd, Chilmark, MA 02535
Est. Refi. Payment $34,981/mo*
Refinance Your HomeCurrently Off Market - Sold Oct 16, 2024 for $6,100,000
Home Value
Trulia Estimate
$6.36MSince last month
Increased$37K (+0.6%)Since last year
Increased$122K (+1.9%)Since last sale
Increased$259K (+4.2%)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 +136% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $6.36M |
| August 2026 | $6.34M |
| July 2026 | $6.32M |
| June 2026 | $6.45M |
| May 2026 | $6.36M |
| April 2026 | $6.29M |
| March 2026 | $6.36M |
| February 2026 | $6.34M |
| January 2026 | $6.27M |
2025 | |
2024 | |
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 |
|---|---|---|---|---|---|---|---|
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 | |
1.52 | Single-Family Home | $8,178,500 | 10/27/25 | 6 | 4.5 | 4,104 | |
1.52 | Single-Family Home | $4,850,000 | 12/05/25 | 5 | 3.5 | 4,044 | |
1.55 | Single-Family Home | $2,800,000 | 08/27/26 | 4 | 3.5 | 2,515 | |
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 | |
1.71 | Single-Family Home | $5,250,000 | 09/03/26 | 4 | 3 | 2,746 | |
1.16 | Single-Family Home | $1,775,000 | 11/07/25 | 3 | 2 | 1,728 |
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 |
|---|---|---|---|---|---|---|
0.23 | $4,103,900 | 3 | 2.5 | 1,316 | Off Market | |
0.31 | - | - | - | - | Off Market | |
0.33 | $3,762,900 | 4 | 4.5 | 3,900 | Off Market | |
0.40 | $1,900,000 | - | - | - | For Sale | |
0.75 | $1,550,000 | 4 | 2 | 1,757 | For Sale | |
0.79 | $1,080,100 | 4 | 2 | 1,701 | Off Market | |
0.83 | $9,750,000 | 7 | 5 | 3,617 | For Sale | |
0.91 | $2,250,000 | 1 | 1 | 726 | For Sale | |
0.95 | $1,897,700 | 4 | 2 | 3,093 | Off Market | |
0.94 | $1,593,500 | 3 | 2 | 1,200 | Off Market | |
1.00 | $1,902,900 | 4 | 3 | 2,780 | Off Market |
Local Information
- Map ViewExplore the area around 391 Middle Rd.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Single-Family Home
Built in 1941
3.3 acre lot
3,859 sqft
$1,648/sqft
About this House
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.
391 Middle Rd, Chilmark, MA 02535 is a 6 bedroom, 5 bathroom, 3,859 sqft single-family home built in 1941. It last sold for $6,100,000 on Oct 16, 2024 (6% below the $6,485,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $6,359,100.
Last check for updates: about 3 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
Home Details for 391 Middle Rd
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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 |
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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 |
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Year Built Year Built: 1941Year Renovated: 2018 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Property Information Usage of Home: 688 |
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Price List Price: $6,485,000 |
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MLS Status: S |
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Direction & Address City: Chilmark |
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Building Area Building Area: 3859 Square Feet |
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Lot Area: 3.3 Acres |
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Listing Agreement Type: E |
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BasementMls Number: 42440 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Oct 16, 2024 Source: LINK #42440 | Sold | $6,100,000 |
Sep 28, 2024 Source: LINK #42440 | Pending | $6,485,000 |
Sep 10, 2024 Source: LINK #42440 | PriceChange | $6,485,000 Price decreased by 7% |
Aug 21, 2024 Source: LINK #42440 | Listed For Sale | $6,950,000 |
Nov 5, 1998 Source: N/A | Sold | $1,400,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $12,396 | $5,509,400 |
Home facts updated by county records
Market trends in Chilmark
Last updated July 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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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.
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© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-06 17:29:43 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.
Frequently asked questions about 391 Middle Rd
- What is 391 Middle Rd estimated to be worth?Trulia's estimated value for 391 Middle Rd in Chilmark, MA is $6,359,100.
- What is the price history for 391 Middle Rd?391 Middle Rd in Chilmark, MA last sold for $6,100,000 in October 2024.
- 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 391 Middle Rd?The closest schools to 391 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 391 Middle Rd?The lot at 391 Middle Rd in Chilmark, MA is about 3.3 acres.
- Does 391 Middle Rd have a garage?Yes, 391 Middle Rd in Chilmark, MA has a garage.
Apartments for Rent
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Off Market Homes Near 391 Middle Rd
SOLDSEP 3, 2026Wallace & Co. Sotheby's International Realty
SOLDAUG 27, 2026Tea Lane Associates
SOLDJUN 26, 2026Tea Lane Associates
SOLDMAY 28, 2026Wallace & Co. Sotheby's
SOLDAPR 10, 2026Flanders Real Estate
SOLDMAR 24, 2026Feiner Real Estate
SOLDMAR 17, 2026Wallace & Co. Sotheby's
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Homes for sale near 391 Middle Rd
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