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308 South Road, Chilmark, MA 02535

Dukes County

Key Facts

4Beds
5Baths
3,490Sq Ft
1999Year Built

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 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.

Property Information

Property Type

Residential

Sub-Type

Single Family Residence

Style

Cape

Year Built

1999

Living Area

3,490 sq ft

Lot Size

3.4 sq ft

Parking Spaces

7

Zoning

RES

Days on Market

131

MLS® Listing#

73478310

Property Features

Cooling

Central AirHeat PumpDuctless

Heating

Active SolarHeat PumpForced AirDuctless

Basement

FullWalk-Out AccessInterior Entry

Lot Features

SlopedWaterfront

Foundation

Concrete Perimeter

Sewer

Private Sewer

Water Source

Private

Financial Details

HOA

None

Annual Taxes

$18,310

Tax year 2026

Assessed Value

$8,030,800

Parcel Number

3567078

Directions

South Road from down-island, take a left into driveway marked 308 just before Abels Hill.

Affordability Calculator

$1,470,000

Estimated monthly payment

$39,120/mo

Principal $5,880,000 · Est. interest $8,203,123 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Chilmark, MA

$1,000,000
Median Listing Price
44
Median Days on Market
3,458
Median Sq Ft
$1,831
Median Price / Sq Ft
18
Active Listings
  • This home’s price is 635% above the area median.
  • Its price per sq ft is 15% above the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Chilmark, MA.

Location

Map showing the location of 308 South Road, Chilmark, MA 02535

Points of Interest in Chilmark, MA

Showing the Chilmark area map.

Nearby Schools

  • Chilmark Elementary

    Elementary · 1.9 mi away

  • Island Childrens School

    School · 4.3 mi away

  • West Tisbury School

    Elementary · 4.5 mi away

  • Martha's Vineyard Public Charter School

    Secondary · 5.4 mi away

  • Martha's Vineyard Regional High School

    Secondary · 7.5 mi away

  • Tisbury Elementary

    Elementary · 8.8 mi away

  • Martha's Vineyard Regional High School

    Secondary · 8.9 mi away

  • Vineyard Montessori School

    Elementary · 9.6 mi away

  • Oak Bluffs Elementary School

    Elementary · 9.9 mi away

  • The Edgartown School

    Elementary · 10.1 mi away

  • Penikese Island School

    School · 12.3 mi away

  • Children's School of Science

    School · 12.4 mi away

  • Mullen Hall School

    School · 15.0 mi away

  • Village Science Playground

    Elementary · 15.0 mi away

  • Falmouth Community School

    School · 15.1 mi away

  • Lawrence School

    Secondary · 15.1 mi away

  • Morse Pond School

    Secondary · 15.5 mi away

  • Sandpiper Nursery School

    School · 15.6 mi away

  • Teaticket Park

    School · 16.3 mi away

  • Falmouth Public Schools - Massachusetts

    School · 16.4 mi away

Commute Calculator

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Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

AddressPriceBedsBathsSq Ft
49 Gosnolds Way, Chilmark, MA$5,200,000544,044
205 South Rd, Chilmark, MA$5,350,000455,402
35 South Bowl Rd, Chilmark, MA$5,400,000322,710
61 Stonewall Road, Chilmark, MA$5,450,000543,513
308 South Road, Chilmark, MA$7,350,000453,490

Moving Cost Estimate

EXIT Agents in Chilmark

Listing Courtesy: Wallace & Co. Sotheby's International Realty - 5086273313

Presented by: Rose Ryley

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. MLS Property Information Network, Inc. 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. Copyright ©2026 MLS Property Information Network, Inc. All Rights Reserved.

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Data provided by MLS Property Information Network. MLS® Listing#73478310. © 2026EXIT Realty®. All rights reserved.