205 S Rd

Chilmark, MA 02535

$5,650,000
Price
4
Beds
5,402 Sq. Ft.
$1,046 / Sq. Ft.
5,402
Sq. Ft.
$1,046
per Sq. Ft.
Get preapproved with Rocket Mortgage1

Description

Classic chilmark retreat. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing...Classic chilmark retreat. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.
  1. Listed by Tina Miller • Donnelly + Co.

Property Details for 205 S Road

Town
Chilmark
MLS Area
Chilmark
Area
MA-Chilmark-Chilmark, MA-Chilmark
Architectural Style
Cape
Style
Cape
Garage Spaces
3
Open Parking Spaces
8.00
Parking Spaces Total
11
LISTING UPDATED: 04/05/2026 08:48 AM

Property Details for 205 S Road

StatusNew
MLS #73495595
Days on Market3
Taxes$13,900 / year
HOA Fees-
Compass TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1940
CountyDukes County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Donnelly + Co., Tina Miller
Add your commute

Building Information for 205 S Road

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

Payment Calculator

Get preapproved with Rocket Mortgage1

$29,609 per month

30 year fixed, 6.46% Interest

Principal and Interest

$28,451

Property Taxes

$1,158

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 205 S Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Living Area: 5402.0
  • SqFt with Basement: No
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Water Heater
  • Basement Features: Full, Partially Finished
  • Num of Baths: 5.0
  • Num of Full Baths: 4
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 4.50
  • Bathrooms Total Integer: 5
  • FireplaceFeatures: 1
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Flooring: 1.5
  • Interior Features: AC,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.
  • Main Level Bedrooms: 3
  • Primary Bath: Yes
  • SpaYN: No
Exterior Features
  • Exterior Features: Deck, Patio, DdBch, Garden
  • Fencing: Fenced/Enclosed
  • Lot Description: Wooded, Cleared, Gentle Sloping
  • Other Structures: Guest house, Horse Barn or Party Barn, Three Bay Garage, Boat House, and Fenced Pasture land. Owned Solar.
  • View: None, Pasture
  • Waterfront Features: Ocean, 3/10 to 1/2 Mile To Beach, Beach Ownership(Deeded Rights)
Parking Features
  • Attached Garage: No
  • Carport: No
  • Covered Spaces: 3.00
  • Garage: Yes
  • Garage Parking: Detached
  • Parking Features: Detached
Utilities
  • Cooling: Central Air, Heat Pump
  • Cooling: Yes
  • Heating: Central
  • Heating: Yes
  • Sewer: Inspection Required for Sale
  • Utility Connections: Cbl
  • Water: Private
Property Information
Property Info
  • UFFI: No
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
Tax Information
  • Tax ID: 3566352
  • Assessments: $5,859
  • Book: 971
  • Lot: 18
  • Map: 107
  • Tax Year: 2025
  • Zoning: RES
Building / Association Information
Living Characteristics
  • Beds Total: 4
Other Building Characteristics
  • Foundation: Concrete Perimeter
Complex & Association Information
  • Adult Community: No

Property History for 205 S Road

DateEvent & SourcePriceAppreciation
Apr 3, 2026

Listed (Active)

MLS PIN #73495595

$5,650,000—
Apr 3, 2026

Listed (Active)

LINK #44028

$5,650,000—
Oct 24, 2025

Canceled

LINK #42251

—
Sep 26, 2003

Sold (Public Record)

Public Record #326395415

$1

-97.0% / yr

Nov 10, 1999

Sold (Public Record)

Public Record #89169042

$750,000—
Nov 10, 1999

Sold (Public Record)

Public Record #89169043

$750,000—
DateEvent & SourcePrice
04/03/2026

Listed (Active)

MLS PIN #73495595

$5,650,000
04/03/2026

Listed (Active)

LINK #44028

$5,650,000
10/24/2025

Canceled

LINK #42251

—
09/26/2003

Sold (Public Record)

Public Record #326395415

$1

-97.0% / yr

11/10/1999

Sold (Public Record)

Public Record #89169042

$750,000
11/10/1999

Sold (Public Record)

Public Record #89169043

$750,000

For completeness, Compass 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
Chilmark Elementary School
Public - K to 5
West Tisbury Elementary School
Public - PK to 8
Martha's Vineyard Regional High School
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

Explore Nearby Homes

More information about 205 S Road, Chilmark, MA 02535

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 $5,650,000. It has been on the market for a total of 3 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, 5,402 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. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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.