308 South Road Chilmark, MA ^$ 7,350,000

308 South Road

^$ 7,350,000

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308 South Road

Chilmark, MA, 02535

^$ 7,350,000

Bedrooms4 Baths4.1 Sq 3,490

Monthly Estimate*

^$ 45,255

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Single Family Home for sale in Chilmark, MA

for $7,350,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,490 square foot home was built in 1999 on a lot size of 3.4.

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.

Single Family Active

Price

^$ 7,350,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 18,000

Style

Cape Cod, Contemporary

Lot Size

3.4

Year Built

1999

Town/City

Chilmark

County/Region

Dukes

MLS | Web ID

22602746

Features

General

Sewer Septic Tank

Cooling Central Air

Roof Pitched Shingle

Appliances Electric Water Heater

Zoning RES

Architectural Style Cape Cod Contemporary

Construction Materials Shingle Siding

Year Built 1999

Stories Count 3

Township Chilmark

Property Subtype Single Family Residence

Tax Year 2026

County Dukes

New Construction false

Property Type Residential

HOA false

Garage Y/N false

Total Rooms 10

Full Baths 4

Status Active

Directions South Road from down-island take a left into driveway marked 308 just before Abel's Hill.

City Chilmark

Body of Water Chilmark Pond

High School District Martha's Vineyard

Lot Size Units Acres

Lot Size Square Feet 148104

Property Attached Y/N false

Land Lease Y/N false

Tax Annual Amount 18000

Home Warranty Y/N false

Property Condition Updated/Remodeled Actual

Virtual Tour https://mls.ricoh360.com/38fd3066-66ba-4d18-8ac7-ede9db067cc5 https://mls.ricoh360.com/38fd3066-66ba-4d18-8ac7-ede9db067cc5

Building Area Units Square Feet

Living Area Units Square Feet

Standard Status Active

Middle/Junior School District Martha's Vineyard

Elementary School District Martha's Vineyard

Tax Assessed Value 8030800

Waterview Y/N Ocean

Interior

Basement Finished Interior Entry Full

Flooring Hardwood

Air Conditioning Y/N true

Heating Y/N true

Fireplace Y/N false

Half Baths 1

Total Bedrooms 4

Below Grade Finished Area Unit Type Square Feet

Total Baths 5

Exterior

Exterior Amenities Outdoor Shower Garden

Water Source Well

Lot Size Area 3.4

Foundation Details Poured

Building Area Total 3490

Lot Size Acres 3.4

Road Surface Type Paved

Lot Size Source Assessor

Waterfront Y/N true

Road Frontage Type Public

Dock None

* Excluded Features

List By

Rose E Ryley

Listing Agent

Wallace & Co. Sotheby's International Realty

Broker

rose@wallacemv.com

Affordability Calculator

$46,755

Per Month

Monthly Principal & Interest: $45,255
Monthly Property Taxes: $1,500
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Chilmark, MA

Average List Price ^$6,726,250

Percent of Sale Price 8%

About Chilmark, MA

871 Population

5% Since 2002

^$91,667 Median Income

52.93 Median Age

17% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

2088120 Elementary School

2088116 Middle School

Unknown High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
6/8/2026	$7,350,000		Listed Price

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308 South Road, Chilmark, MA, 02535 is a Single Family Home for sale at $7,350,000 with 3,490 sqft and a lot size of 3.4. 308 South Road has 4 bedrooms, 4.1 baths, and was built in 1999. The property's zip code is 02535 which is in Chilmark, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Weichert Realtors include the name of the listing broker company. Neither the listing company nor Weichert Realtors shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 6/11/2026. All properties are subject to prior sale, changes, or withdrawal.

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308 South Road

Single Family Home for sale in Chilmark, MA

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