2,350 Sq. Ft.
$1,053 / Sq. Ft.
2,350
Sq. Ft.
$1,053
per Sq. Ft.

Description

Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian...Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian pursuits or a small gentleman’s farm—an increasingly uncommon offering in Chilmark at this price point. The open acreage invites outdoor living, from summer entertaining and gardening to quiet enjoyment of the surrounding landscape and privacy. Inside, the home balances antique charm with thoughtful updates. Four bedrooms and three full baths include two main-level bedrooms and two second-floor en-suite guest rooms, creating a comfortable and flexible layout for hosting family and friends. Living spaces are warm and inviting, with a masonry double fireplace, preserved period details, and an updated kitchen and baths. Recent improvements include HVAC, windows, insulation, and a five-bedroom septic system, offering flexibility for future expansion and barn renovation. Located steps from West Tisbury village, Alleys General Store, the library, the Yoga Barn, the Grange Hall and nearby conservation trails, the setting combines convenience with the privacy and natural beauty that define Chilmark. A distinctive Vineyard offering with uncommon versatility—equally suited as a summer retreat, year-round residence, or small-scale farmstead.

Property Details for 16 S Road

Zoning
RES
View
None, Pasture
LISTING UPDATED: 03/28/2026 04:47 PM

Property Details for 16 S Road

StatusActive
MLS #44181
Days on Market31
Taxes$4,100 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1885
Lot Size1.60 AC / 69,696 SF
CountyDukes County

Location

Listing Courtesy of Vineyard Village Realty, Michele Casavant
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Building Information for 16 S Road

Stories-Year Built1885Building Size-Lot Size1.60 AC / 69,696 SF

Payment Calculator

$12,805 per month

30 year fixed, 6.46% Interest

Principal and Interest

$12,463

Property Taxes

$342

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 16 S Road

Summary
Location and General Information
  • Latitude: 41.3761642
  • Longitude: -70.6787215
  • Listing ods: Deck, Garden, Patio, Porch
  • MLS Area Major: 5
Taxes and HOA Information
  • Tax Assessed Value: $905,900.00
  • Tax Lot: 20
  • Tax Map Number: 11
  • Tax Other Annual Assessment Amount: $697,800.00
  • Tax Year: 2025
Parking
  • Parking Features: plenty of off street parking
Property
Lot Information
  • Lot Features: Boundary Line Agreement book 01373, page 0990, expansive large yard and field for horses, animals and gardneing
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 30
  • Deed No: 1668
  • Approval Status: -1
  • Reviewed: Yes
  • Year Built Effective: 2018
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Garden, Patio, Porch
Interior Features
  • Main Level Bedrooms: 2
  • Other Structures: Large barn with electricity, two levels and garage area. Chicken coop and shed. Horse run-in barn with two stalls.
  • Rooms Total: 8
  • Appliances: Stove: Thermador, Washer: yes
  • Fireplace Features: yes
  • Fireplace: No
  • Flooring: hardwood and tile
  • Foundation Details: mixed-parital poured concrete, partial granite
  • Furnished: Unfurnished
  • Heating: Propane
  • Interior Features: AC,Ins,MiniSplit, Floor 1: Front and side foyer, two lounge areas, one with a masonry fireplace, cathedral ceiling and oversized for dining. A kitchen with a cathedral ceiling, and kitchen island, a full bath. A breaze way for additional storage of shoes, coats and sporting equipment. Two bedrooms., Floor 2: Two bedroom en-suites, each with their own bathroom., Floor 3: Attic space

Property History for 16 S Road

DateEvent & SourcePriceAppreciation
Mar 28, 2026

Price Change

LINK #44181

$2,475,000
Mar 9, 2026

Listed (Active)

LINK #44181

$2,500,000
Dec 15, 2025

Canceled

LINK #43515

$2,500,000
Jul 30, 2025

Canceled

MLS PIN #73399410

$2,500,000
Jul 3, 2025

Listed (Active)

MLS PIN #73399410

$2,500,000
Jul 2, 2025

Listed (Active)

LINK #43515

$2,500,000
Nov 15, 2023

Sold

LINK #41375

$2,012,000
Nov 14, 2023

Sold

Martha's Vineyard MLS #32300406

$2,012,000
Oct 3, 2023

Under Agreement

LINK #41375

Oct 3, 2023

Contingent

LINK #41375

Sep 29, 2023

Listed (Active)

LINK #41375

$1,900,000
Apr 17, 2015

Sold (Public Record)

Public Record #521028485

$800,000
Apr 17, 2015

Sold

LINK #27378

$800,000
Jan 6, 2015

Contingent

LINK #27378

Oct 1, 2014

Listed (Active)

LINK #27378

$899,000
DateEvent & SourcePrice
03/28/2026

Price Change

LINK #44181

$2,475,000
03/09/2026

Listed (Active)

LINK #44181

$2,500,000
12/15/2025

Canceled

LINK #43515

$2,500,000
07/30/2025

Canceled

MLS PIN #73399410

$2,500,000
07/03/2025

Listed (Active)

MLS PIN #73399410

$2,500,000
07/02/2025

Listed (Active)

LINK #43515

$2,500,000
11/15/2023

Sold

LINK #41375

$2,012,000
11/14/2023

Sold

Martha's Vineyard MLS #32300406

$2,012,000
10/03/2023

Under Agreement

LINK #41375

10/03/2023

Contingent

LINK #41375

09/29/2023

Listed (Active)

LINK #41375

$1,900,000
04/17/2015

Sold (Public Record)

Public Record #521028485

$800,000
04/17/2015

Sold

LINK #27378

$800,000
01/06/2015

Contingent

LINK #27378

10/01/2014

Listed (Active)

LINK #27378

$899,000

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

Public Records for 16 S Road

Taxable ValueLand$697,800Additions$952,700Total$1,650,500
Tax Record2025$3,714 ($310 / month)
Home Facts
Beds4Baths2Total Finished SqFt2,204 SqFtAbove Grade Finished SqFt2,204 SqFtStories2Lot Size69,696 SqFtStyleSingle Family ResidenceYear Built1885Year Renovated1982Zoning1-3CountyDUKESAPNCHIL M:11 P:20

Schools near 16 S Road

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

Martha's Vineyard Regional High School
Public9 to 12

Chilmark Elementary School
PublicK to 5

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

16 S Road is a single family home for sale in Chilmark, MA 02535. This property was listed for sale on March 9, 2026 by Vineyard Village Realty, it's currently listed at $2,475,000. It has been on the market for a total of 31 days and was last sold on November 15, 2023. This listing's school districts are Up-Island Regional School District, Marthas Vineyard School District. Nearby schools include West Tisbury Elementary School, Martha's Vineyard Regional High School and Chilmark Elementary School. 16 S Road is a 4-bed, 3-bath, 2,350 sqft single family home built in 1885.

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 Vineyard Village Realty, Michele Casavant

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.