6,162 Sq. Ft.
$868 / Sq. Ft.
6,162
Sq. Ft.
$868
per Sq. Ft.

Description

Classic chilmark retreat. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space. The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and...Classic chilmark retreat. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space. The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and entertaining. An expanded primary suite wing includes a spacious primary bedroom, full bath, bright office, half bath, and dedicated laundry. A second-story space offers flexibility as an art studio, office, or media room. A classic three-season living room invites relaxed enjoyment of the surrounding landscape, including distant winter waterviews. Well-suited for compound living, the property is perfect for the equestrian and includes a guest house, horse barn, fenced pastureland, garage, and an old boat shed—providing exceptional flexibility for family, guests, and a wide range of outdoor pursuits. Deeded access to Chilmark Pond and South Shore Beach offers a rare opportunity to enjoy swimming, kayaking, and some of the Island’s most beautiful and unspoiled coastline. This property has a seven-bedroom septic, full solar, and abuts acres of conservation land. Ideally located in the heart of Chilmark, the property is just minutes from Alley’s Store, Lucy Vincent Beach, Chilmark Tavern, Beetlebung Farm, the Chilmark Store, and more—perfectly capturing the essence of the Chilmark lifestyle and the very best of Vineyard living.

Property Details for 205 S Road

Zoning
RES
View
None, Pasture
LISTING UPDATED: 05/14/2026 08:10 AM

Property Details for 205 S Road

StatusActive
MLS #44028
Days on Market61
Taxes$13,900 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1940
Lot Size5.99 AC / 260,924 SF
CountyDukes County

Location

Listing Courtesy of Donnelly + Co, Tina Miller
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Building Information for 205 S Road

Stories-Year Built1940Building Size-Lot Size5.99 AC / 260,924 SF

Payment Calculator

$27,818 per month

30 year fixed, 6.36% Interest

Principal and Interest

$26,660

Property Taxes

$1,158

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 205 S Road

Summary
Location and General Information
  • Latitude: 41.3572121
  • Longitude: -70.69473
  • Listing ods: Deck, Patio, DdBch, Garden
  • Listing other Building: Grg
  • MLS Area Major: 5
Taxes and HOA Information
  • Tax Assessed Value: $4,351,000.00
  • Tax Lot: 18
  • Tax Map Number: 107
  • Tax Other Annual Assessment Amount: $1,508,000.00
  • Tax Year: 2026
Parking
  • Parking Features: ample
Property
Lot Information
  • Lot Features: ample
  • Lot Size Units: Acres
  • Property Type: 1 Family
Property and Assessments
  • Parcel Number: 3566352
  • Photos Count: 48
  • Approval Status: -1
  • Reviewed: Yes
  • Year Built Effective: 2014
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Patio, DdBch, Garden
Interior Features
  • Main Level Bedrooms: 3
  • Other Structures: Guest house, Horse Barn or Party Barn, Three Bay Garage, Boat House, Grid Tied Solar Panels System and Fenced Pasture land.
  • Rooms Total: 9
  • Appliances: Stove: Bertazzoni, Washer: Yes
  • Fireplace Features: 1
  • Fireplace: No
  • Flooring: 1.5
  • Foundation Details: Poured concrete
  • Furnished: Unfurnished
  • Heating: GFHA
  • Interior Features: Ins,OSh, Floor 1: Open kitchen, living room, sprawling primary bedroom wing. Three-season living area, two en suite bedrooms, Floor 2: Art studio, office or media space. Also, a loft area off the living room.

Property History for 205 S Road

DateEvent & SourcePriceAppreciation
May 14, 2026

Price Change

MLS PIN #73495595

$5,350,000
May 14, 2026

Price Change

LINK #44028

$5,350,000
Apr 3, 2026

Listed (Active)

MLS PIN #73495595

$5,650,000
DateEvent & SourcePrice
05/14/2026

Price Change

MLS PIN #73495595

$5,350,000
05/14/2026

Price Change

LINK #44028

$5,350,000
04/03/2026

Listed (Active)

MLS PIN #73495595

$5,650,000

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

Public Records for 205 S Road

Taxable ValueLand$1,436,100Additions$4,178,000Total$5,614,100
Tax Record2025$12,632 ($1,053 / month)
Home Facts
Total Finished SqFt5,506 SqFtAbove Grade Finished SqFt5,506 SqFtStories1Lot Size260,924 SqFtStyleMulti-Family Dwelling (2-4)Year Built1940Year Renovated2006Zoning1-3CountyDUKESAPNCHIL M:18 P:107

Schools near 205 S 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

205 S Road is a single family home for sale in Chilmark, MA 02535. This property was listed for sale on April 3, 2026 by Donnelly + Co, it's currently listed at $5,350,000. It has been on the market for a total of 61 days and was last sold on September 26, 2003. 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. 205 S Road is a 4-bed, 5-bath, 6,162 sqft single family home built in 1940.

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 Donnelly + Co, Tina Miller

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.