3,490 Sq. Ft.
$2,106 / Sq. Ft.
3,490
Sq. Ft.
$2,106
per Sq. Ft.

Description

Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond...Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot, included in this sale. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to embracing the Chilmark lifestyle defined by privacy, water access, and understated elegance.
  1. Listed by Rose Ryley • Wallace & Co. Sotheby's International Realty

Property Details for 308 S Road

Parking Features
Ample driveway parking
Waterfront
Yes
Zoning
RES
Style
Cape Cod, Contemporary
TopographyLot Desc:View
Oceanfront
LISTING UPDATED: 01/09/2026 09:51 AM

Property Details for 308 S Road

StatusActive
MLS #32600003
Days on Market14
Taxes$17,211 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1999
Lot Size3.40 AC / 148,104 SF
CountyDukes County

Location

Listing Courtesy of Wallace & Co. Sotheby's International Realty, Rose Ryley
Add your commute

Building Information for 308 S Road

Stories3Year Built1999Building Size-Lot Size3.40 AC / 148,104 SF

Payment Calculator

$37,257 per month

30 year fixed, 6.15% Interest

Principal and Interest

$35,823

Property Taxes

$1,434

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 308 S Road

Summary
Location and General Information
  • MLS Area Major: 5
Taxes and HOA Information
  • Tax Year: 2025.0
  • Parcel Number: CHIL M:24 P:204
  • Annual Assoc Fee: $0
  • Annual Taxes: $17,211
  • Other Assessments: 0.0
  • Legal and Taxes:Annual Taxes: $17,211
Parking
  • Garage: No
Property
Lot Information
  • Additional SqFt Source: Plans
  • Lot Features: Beautifully landscaped tiered yard with gorgeous water views
  • Acres: 3.4
  • Lot Size Units: Acres
  • Lot Size Square Feet: 148104.0
  • Total Finished Space: 3490.0
  • Legal and Taxes:Map/Lot: CHIL M:24 P:204
  • General Property Info:Leased Land: No
Property and Assessments
  • Year Built Details: Actual
  • Year Built: 1999
  • Property Sub-Type: Single Family Residence
  • Property Type: Residential
  • Legal and Taxes:Land Assessments: 4949500.0
  • Legal and Taxes:Building Assessments: 2699900.0
  • Legal and Taxes:Other Assessments: 0.0
  • Legal and Taxes:Total Assessment: 7649400.0
Utilities
  • Water Source: Well
  • Fuel Type:Electric: True
  • Utilities: Cbl
Interior and Exterior Features
Interior Features
  • Heating: Forced Air, Heat Pump
  • Stories: 3
  • Cooling: Central Air
  • Number of Fireplaces: 0
  • Fireplace: No
  • Interior Features: A,AC,Ins,Irr,MiniSplit,OSh, Floor 1: See floor plans, Floor 2: See floor plans
  • Basement: Yes
  • Flooring: Hardwood
  • Foundation Details: Poured concrete - full basement
  • Room Total: 10
  • Total Floor Plans Count: 4
  • Bathrooms Total (Integer): 4
  • Bathrooms Total (Decimal): 3.50
  • Bathrooms Total (Notational): 3.10
  • Cooling: Yes
  • Fireplace Features: No
  • Heating: Yes
  • Bedrooms - Total: 4
  • Baths - Full: 3
  • Baths - Half: 1
  • Kitchen Appliances: Water Heater
  • Basement Description:Interior Access: Yes
  • Basement Description:Walk Out: Yes
  • Floors:Hardwood: Yes
  • Heating:Heat Pump: Yes
  • Cooling:Central Air: Yes
Exterior Features
  • Exterior Features: WViews, Deck, Garden, Patio, PvtBch, DdBch
Rental
Rental Information
  • Landlord Pays:Sewer: Septic Tank

Property History for 308 S Road

DateEvent & SourcePriceAppreciation
Jan 9, 2026

Listed (Active)

LINK #43955

$7,350,000—
Jan 9, 2026

Listed (Active)

Martha's Vineyard MLS #32600003

$7,350,000—
Nov 1, 2025

Expired

Martha's Vineyard MLS #32500143

—
Oct 31, 2025

Canceled

Martha's Vineyard MLS #32500143

—
Oct 31, 2025

Canceled

LINK #43117

$7,350,000—
Sep 16, 2025

Price Change

Martha's Vineyard MLS #32500143

$7,350,000—
May 8, 2025

Listed (Active)

LINK #43117

$7,950,000—
May 8, 2025

Listed (Active)

Martha's Vineyard MLS #32500143

$7,950,000—
Oct 19, 2020

Price Change

LINK #11170

$5,950,000—
Jan 22, 2007

Sold (Public Record)

Public Record #214143039

$5,050,000

+12.1% / yr

Jan 22, 2007

Sold

LINK #11170

$5,050,000—
Jun 14, 2006

Listed (Active)

LINK #11170

$5,950,000—
Jan 16, 1998

Sold (Public Record)

Public Record #89169052

$1,800,000—
DateEvent & SourcePrice
01/09/2026

Listed (Active)

LINK #43955

$7,350,000
01/09/2026

Listed (Active)

Martha's Vineyard MLS #32600003

$7,350,000
11/01/2025

Expired

Martha's Vineyard MLS #32500143

—
10/31/2025

Canceled

Martha's Vineyard MLS #32500143

—
10/31/2025

Canceled

LINK #43117

$7,350,000
09/16/2025

Price Change

Martha's Vineyard MLS #32500143

$7,350,000
05/08/2025

Listed (Active)

LINK #43117

$7,950,000
05/08/2025

Listed (Active)

Martha's Vineyard MLS #32500143

$7,950,000
10/19/2020

Price Change

LINK #11170

$5,950,000
01/22/2007

Sold (Public Record)

Public Record #214143039

$5,050,000

+12.1% / yr

01/22/2007

Sold

LINK #11170

$5,050,000
06/14/2006

Listed (Active)

LINK #11170

$5,950,000
01/16/1998

Sold (Public Record)

Public Record #89169052

$1,800,000

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

Public Records for 308 S Road

Taxable ValueLand$4,949,500Additions$2,699,900Total$7,649,400
Tax Record2025$17,211 ($1,434 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,553 SqFtAbove Grade Finished SqFt2,553 SqFtStories2Lot Size148,104 SqFtStyleSingle Family ResidenceYear Built1999Zoning2B-3CountyDUKESAPNCHIL M:24 P:204

Schools near 308 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

Similar Sold Homes

308 S Road is a single family home for sale in Chilmark, MA 02535. This property was listed for sale on January 9, 2026 by Wallace & Co. Sotheby's International Realty, it's currently listed at $7,350,000. It has been on the market for a total of 14 days and was last sold on January 22, 2007. 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. 308 S Road is a 4-bed, 4-bath, 3,490 sqft single family home built in 1999.

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 makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Wallace & Co. Sotheby's International Realty, Rose Ryley

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.