This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected conservation land of Menemsha Hills, the property enjoys a natural buffer along with direct access to scenic walking trails and some of Chilmark’s most iconic views. Ideally located just a short distance from Menemsha and Chilmark Center, it offers both seclusion and accessibility. Homeowners will also have access to Lucy Vinecent and Squibnocket beaches as Chilmark property owners. With an established rental history and full winterization for year-round use, this home is well-suited for both personal enjoyment and income generation. For those seeking a foothold in one of Martha’s Vineyard’s most desirable towns, this is a compelling opportunity not to be missed.
For sale
$1,550,000
345 North Rd, Chilmark, MA 02535
5beds
2,266sqft
Est.:
Single Family Residence
Built in 1981
0.5 Acres Lot
$1,532,900 Zestimate®
$684/sqft
$-- HOA
What's special
Two separate parking areas
- 13 days |
- 768 |
- 23 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Jessica Campbell,
Flanders Real Estate
Source: LINK,MLS#: 44126
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 5
Heating
- Heat Pump
Appliances
- Included: Stove: Yes, Washer: Yes
Features
- Ins, MiniSplit, OSh, WdStove, Floor 1: Entryway leads to the living room, Dining room, Kitchen with a smaller dining area, first-floor bathroom, Laundry, and utility closet., Floor 2: Up the stairs leads to 4 Bedrooms and 3 bathrooms, with a deck off the Primary suite, Floor 3: N/A
- Flooring: Bamboo
- Basement: Slab
- Fireplace features: 3
Interior area
- Total structure area: 2,266
- Total interior livable area: 2,266 sqft
Property
Parking
- Parking features: Multiple spaces to park
Features
- Exterior features: PubBch, Deck, Patio
- Has view: Yes
- View description: None, Trees/Woods
- Frontage type: None
Lot
- Size: 0.5 Acres
- Features: Yes
Details
- Additional structures: Detached Guest bedroom with full bathroom and Kitchenette. Garage attached to the guest quarters.
- Parcel number: CHILM20P38
- Zoning: RES
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Concrete Slab
Condition
- Year built: 1981
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cbl
Community & HOA
Location
- Region: Chilmark
Financial & listing details
- Price per square foot: $684/sqft
- Tax assessed value: $1,243,100
- Annual tax amount: $3,449
- Date on market: 4/20/2026
- Listing agreement: E
Estimated market value
$1,532,900
$1.46M - $1.61M
$7,649/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/20/2026 | Listed for sale | $1,550,000-4.6%$684/sqft |
Source: LINK #44126 Report a problem | ||
| 10/12/2025 | Listing removed | $1,625,000$717/sqft |
Source: Martha's Vineyard MLS #32400300 Report a problem | ||
| 5/9/2025 | Price change | $1,625,000-4.1%$717/sqft |
Source: Martha's Vineyard MLS #32400300 Report a problem | ||
| 2/22/2025 | Listed for sale | $1,695,000-5.8%$748/sqft |
Source: Martha's Vineyard MLS #32400300 Report a problem | ||
| 10/27/2024 | Listing removed | $1,800,000$794/sqft |
Source: LINK #42591 Report a problem | ||
| 10/11/2024 | Listed for sale | $1,800,000+125%$794/sqft |
Source: LINK #42591 Report a problem | ||
| 11/25/2019 | Sold | $800,000-3%$353/sqft |
Source: LINK #35429 Report a problem | ||
| 9/16/2019 | Price change | $825,000-3.5%$364/sqft |
Source: Tea Lane Associates #35429 Report a problem | ||
| 7/4/2019 | Listed for sale | $855,000+263.8%$377/sqft |
Source: Tea Lane Associates #35429 Report a problem | ||
| 2/25/1994 | Sold | $235,000$104/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,797 +15.8% | $1,243,100 +9.1% |
| 2024 | $2,415 +4.5% | $1,139,000 +29.5% |
| 2023 | $2,312 +1.7% | $879,200 +9% |
| 2022 | $2,274 +5% | $806,300 +8.3% |
| 2021 | $2,166 +21.4% | $744,200 +19.3% |
| 2020 | $1,784 +2.8% | $623,800 +3.5% |
| 2019 | $1,735 +4.7% | $602,500 |
| 2018 | $1,657 +2.9% | $602,500 +0.3% |
| 2017 | $1,610 -0.6% | $600,900 +0.6% |
| 2016 | $1,619 | $597,500 |
Find assessor info on the county website
Monthly payment
Est. payment
$8,209/mo
Principal & interest
$7563
Property taxes
$646
More affordability tools
Climate risks
Neighborhood: 02535
Nearby schools
GreatSchools rating
- 8/10Chilmark Elementary SchoolGrades: K-5Distance: 1.6 mi
- 7/10West Tisbury Elementary SchoolGrades: PK-8Distance: 4.9 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 8.4 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Massachusetts
- Dukes County
- Chilmark
- 02535
- 345 North Rd
Nearby cities
Nearby zip codes
Other Chilmark Topics
