2,266 Sq. Ft.
$684 / Sq. Ft.
2,266
Sq. Ft.
$684
per Sq. Ft.

Description

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...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.

Property Details for 345 N Road

Zoning
RES
View
None, Trees/Woods
LISTING UPDATED: 04/20/2026 10:56 PM

Property Details for 345 N Road

StatusActive
MLS #44126
Days on MarketListed Today
Taxes$3,450 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1981
Lot Size0.50 AC / 21,780 SF
CountyDukes County

Location

Listing Courtesy of Flanders Real Estate, Jessica Campbell
Add your commute

Building Information for 345 N Road

Stories-Year Built1981Building Size-Lot Size0.50 AC / 21,780 SF

Payment Calculator

$8,093 per month

30 year fixed, 6.46% Interest

Principal and Interest

$7,805

Property Taxes

$288

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 345 N Road

Summary
Location and General Information
  • Latitude: 41.3644544
  • Longitude: -70.7413908
  • Listing ods: PubBch, Deck, Patio
  • Listing other Building: Grg
  • MLS Area Major: 5
Taxes and HOA Information
  • Tax Assessed Value: $675,700.00
  • Tax Lot: 38
  • Tax Map Number: 20
  • Tax Other Annual Assessment Amount: $567,400.00
  • Tax Year: 2025
Parking
  • Parking Features: Multiple spaces to park
Property
Lot Information
  • Lot Features: Yes
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 23
  • Approval Status: -1
  • Reviewed: Yes
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Exterior Features: PubBch, Deck, Patio
Interior Features
  • Main Level Bedrooms: 0
  • Other Structures: Detached Guest bedroom with full bathroom and Kitchenette. Garage attached to the guest quarters.
  • Rooms Total: 11
  • Appliances: Stove: Yes, Washer: Yes
  • Fireplace Features: 3
  • Fireplace: No
  • Flooring: Bamboo
  • Foundation Details: Concrete Slab
  • Furnished: Unfurnished
  • Heating: Heat Pump
  • Interior 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

Property History for 345 N Road

DateEvent & SourcePriceAppreciation
Apr 20, 2026

Listed (Active)

LINK #44126

$1,550,000
Oct 11, 2025

Expired

Martha's Vineyard MLS #32400300

Sep 23, 2025

Canceled

LINK #42920

$1,625,000
Feb 22, 2025

Listed (Active)

LINK #42920

$1,695,000
Oct 27, 2024

Canceled

Martha's Vineyard MLS #32400300

Oct 27, 2024

Canceled

LINK #42591

$1,800,000
Oct 11, 2024

Expired

Martha's Vineyard MLS #32400300

Oct 11, 2024

Listed (Active)

Martha's Vineyard MLS #32400300

$1,800,000
Oct 11, 2024

Listed (Active)

LINK #42591

$1,800,000
Nov 25, 2019

Sold

LINK #35429

$800,000
Nov 25, 2019

Sold

Martha's Vineyard MLS #21805458

$800,000
Sep 23, 2019

Contingent

LINK #35429

Sep 16, 2019

Price Change

LINK #35429

$825,000
Jul 3, 2019

Listed (Active)

LINK #35429

$855,000
Feb 25, 1994

Sold (Public Record)

Public Record #89169302

$235,000
DateEvent & SourcePrice
04/20/2026

Listed (Active)

LINK #44126

$1,550,000
10/11/2025

Expired

Martha's Vineyard MLS #32400300

09/23/2025

Canceled

LINK #42920

$1,625,000
02/22/2025

Listed (Active)

LINK #42920

$1,695,000
10/27/2024

Canceled

Martha's Vineyard MLS #32400300

10/27/2024

Canceled

LINK #42591

$1,800,000
10/11/2024

Expired

Martha's Vineyard MLS #32400300

10/11/2024

Listed (Active)

Martha's Vineyard MLS #32400300

$1,800,000
10/11/2024

Listed (Active)

LINK #42591

$1,800,000
11/25/2019

Sold

LINK #35429

$800,000
11/25/2019

Sold

Martha's Vineyard MLS #21805458

$800,000
09/23/2019

Contingent

LINK #35429

09/16/2019

Price Change

LINK #35429

$825,000
07/03/2019

Listed (Active)

LINK #35429

$855,000
02/25/1994

Sold (Public Record)

Public Record #89169302

$235,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 345 N Road

Taxable ValueLand$567,400Additions$675,700Total$1,243,100
Tax Record2025$2,797 ($233 / month)
Home Facts
Total Finished SqFt1,260 SqFtAbove Grade Finished SqFt1,260 SqFtStories1Lot Size21,780 SqFtStyleMulti-Family Dwelling (2-4)Year Built1991Zoning2A-3CountyDUKESAPNCHIL M:20 P:38

Schools near 345 N Road

This home is within Up-Island Regional School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - PK to 8
Public - 9 to 12
Rating
School
Distance
Chilmark Elementary School
PublicK to 5

West Tisbury Elementary School
PublicPK to 8

Martha's Vineyard Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

345 N Road is a single family home for sale in Chilmark, MA 02535. This listing's school districts are Up-Island Regional School District, Marthas Vineyard School District. Nearby schools include Chilmark Elementary School, West Tisbury Elementary School and Martha's Vineyard Regional High School. 345 N Road is a 5-bed, 5-bath, 2,266 sqft single family home built in 1981.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Flanders Real Estate, Jessica Campbell

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.