252 Middle Rd
Chilmark, MA 02535
- 3 Beds
- 1.5 Baths
- 1,224 sqft (on 1.30 acres)
3 Beds
1.5 Baths
1,224 sqft
(on 1.30 acres)
Local Information
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Description
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.
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
No Info
A/C
Cooling only
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 252 Middle Rd
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Levels, Entrance, & Accessibility Stories: 1Floors: Hardwood |
Interior Details Number of Rooms: 6 |
Appliances & Utilities DryerWasher |
Heating & Cooling Cooling System: Other |
Fireplace & Spa Fireplace |
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Year Built Year Built: 1973 |
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary |
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Exterior Home Features Exterior: Other |
Parking & Garage Parking: Off Street |
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Units in Building: 1 |
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Lot Area: 1.30 acres |
Price History for 252 Middle Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 01/07/2021 | $1,047,500 | Sold | LINK #37589 |
| 11/30/2020 | $1,135,000 | Listed For Sale | Agent Provided |
| 10/22/2020 | $975,000 | Sold | LINK #35294 |
| 08/05/2020 | $1,060,000 | Listed For Sale | Agent Provided |
| 12/03/2019 | $1,060,000 | ListingRemoved | Agent Provided |
| 06/05/2019 | $1,060,000 | Listed For Sale | Agent Provided |
| 03/25/2018 | $3,750 | ListingRemoved | Agent Provided |
| 03/24/2018 | $3,750 | Listed For Rent | Agent Provided |
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $3,167 |
| Assessment | $1,407,600 |
Home facts updated by county records
Comparable Sales for 252 Middle Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $1,775,000 | 11/07/25 | 3 | 2 | 1,728 | |
0.32 | Single-Family Home | $2,100,000 | 11/25/25 | 4 | 3 | 2,544 | |
0.93 | Single-Family Home | $1,607,000 | 07/10/25 | 4 | 3 | 2,850 | |
0.91 | Single-Family Home | $2,475,000 | 09/05/25 | 4 | 3.5 | 2,300 | |
1.41 | Single-Family Home | $2,225,000 | 10/24/25 | 4 | 3 | 2,968 | |
1.01 | Single-Family Home | $7,289,000 | 10/15/25 | 4 | 5 | 3,777 | |
1.02 | Single-Family Home | $4,325,000 | 12/05/25 | 5 | 2.5 | 3,885 | |
2.08 | Single-Family Home | $1,050,000 | 05/29/25 | 4 | 2 | 1,701 | |
0.95 | Single-Family Home | $6,100,000 | 03/24/26 | 6 | 7 | 5,660 | |
1.72 | Single-Family Home | $3,710,000 | 03/12/26 | 3 | 5 | 3,171 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 252 Middle Rd.
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.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 252 Middle Rd
Off Market Homes Near 252 Middle Rd
Homes for rent near 252 Middle Rd
252 Middle Rd, Chilmark, MA 02535 is a 3 bedroom, 2 bathroom, 1,224 sqft single-family home built in 1973. This property is not currently available for sale. 252 Middle Rd was last sold on Jan 7, 2021 for $1,047,500. The current Trulia Estimate for 252 Middle Rd is $1,617,700.

