Pending

$7,350,000

Est. $41,072/mo —

•

3,490

sq ft

308 South Rd, Chilmark, MA 02535

About this home

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-familyProperty Type

1999Year Built

3 sq ftLot Size

$2,106Price/Sq.Ft.

7 spacesParking

Listed by Rose Ryley • Wallace & Co. Sotheby's International Realty

Listing updated: Aug 18, 2026 at 03:10am

Redfin checked: 2 minutes ago

•Source:MLS PIN #73478310

Payment calculator

$41,072 per month

Principal and interest$38,138

Property taxes

$1,526

HOA dues

Home insurance

$1,409

Utilities

Add

5 minutes to get started. No credit impact.

Mortgage resources

Open houses

No upcoming open houses.

Nearby open houses (2)

Around this home

Schools

K - 12
Preschool & daycare

Chilmark Elementary School

Public K-5 • Assigned • 1.9mi

8/10

West Tisbury Elementary School

Public PreK-8 • Assigned • 4.5mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 7.6mi

6/10

Provided by GreatSchools

About Martha's

Vineyard

Martha's Vineyard, located between Vineyard Sound and Nantucket Sound, is a coastal and rural West Tisbury neighborhood with wooded back roads and broad farm fields. The neighborhood’s character concentrates around the West Tisbury Village Center at State Road and Edgartown–West Tisbury Road, where the library lawn, small shops, and a low-key town-green rhythm set the pace. Architecture leans to shingled cottages, classic capes, and working farm outbuildings tucked behind stone walls. The Polly Hill Arboretum adds curated woodland paths and rare plantings to the island’s natural palette. The Grange Hall anchors a calendar of community gatherings, while Alley’s General Store keeps the everyday essentials distinctly local. Long Point Wildlife Refuge and nearby beaches frame a lifestyle shaped by trails, ponds, and salt air.

Provided by Walk Score and Local Logic

Market insights

308 South Rd · $7,350,000

DAYS ON MARKET

The average home goes pending in 54 days.

SALE-TO-LIST

Most homes are selling 5% below list price.

LIST PRICE

Median sale price in this area is $2,623,032. (64% lower than this home)

PRICE DROP

13% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
10 total rooms
Full walk-out basement with interior entry

Bathrooms
4 full bathrooms
1 half bathroom

Heating & cooling
Forced air heating
Heat pump
Active solar heating
Ductless heating
Central air conditioning
Heat pump cooling
Active solar cooling
Ductless cooling

Sale and tax history for 308 South Rd

Sale History
Tax History

Date

Event

Price

MLS PIN #73478310

Aug 18, 2026

Pending

—

Aug 4, 2026

Contingent

—

Feb 18, 2026

Listed

$7,350,000

$2,106/sq ft

CCIMLS #22602746

Aug 4, 2026

Pending

—

Jan 22, 2026

Listed

$7,350,000

$2,106/sq ft

+35

Public Records

Jan 22, 2007

Sold

$5,050,000

$1,447/sq ft

Public Records

Jan 16, 1998

Sold

$1,800,000

$516/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$15,010 (+2.4%)

$3,685,200 + $2,021,900

$5,707,100

2022

$14,654 (+1.6%)

$3,476,500 + $1,720,000

$5,196,500

2021

$14,418 (+3.4%)

$3,476,500 + $1,478,200

$4,954,700

2020

$13,946 (+1.3%)

$3,408,300 + $1,468,000

$4,876,300

2019

$13,767 (+4.7%)

$3,408,300 + $1,371,800

$4,780,100

2018

$13,145 (+2.9%)

$3,408,300 + $1,371,800

$4,780,100

2017

$12,780 (−0.9%)

$3,408,300 + $1,360,500

$4,768,800

2016

$12,895 (+2.7%)

$3,408,300 + $1,349,900

$4,758,200

2015

$12,555

$3,408,300 + $1,365,300

$4,773,600

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

3.4 Acres

Year renovated

1999

Finished Sq. Ft.

2,609

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,609

Year built

1999

Style

Single Family Residential

County

Dukes County

APN

3567078

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 30, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 87° expected this year, 20 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Chilmark, MA • 02535

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

97/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.2 hrs

6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 308 South Rd

$6,970,123

$380K under list price of $7.35M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.6M to $3.7M.

SOLD MAR 12, 2026
$3,710,000 Last sold price
3 beds5 baths3,171 sq ft
15 Old Farm Rd, Chilmark, MA 02535
$936/sq ft
larger lot
3 years newer
SOLD JAN 9, 2026
$1,575,000 Last sold price
3 beds3 baths2,308 sq ft
453 Lighthouse Rd, Aquinnah, MA 02535
$1424/sq ft
larger lot
29 years older
SOLD AUG 5, 2026
$2,013,500 Last sold price
4 beds3.5 baths2,428 sq ft
35 Nats Farm Ln, West Tisbury, MA 02575
$1277/sq ft
larger lot
13 years older
SOLD OCT 24, 2025
$2,225,000 Last sold price
4 beds3 baths2,968 sq ft
9 Beetlebung Grove Way, Chilmark, MA 02535
$1356/sq ft
larger lot
5 years older
SOLD MAY 28, 2026
$2,000,000 Last sold price
4 beds3.5 baths2,690 sq ft
151 Tashmoo Ave, Tisbury, MA 02468
$1363/sq ft
larger lot
23 years newer
SOLD MAR 31, 2026
$1,850,000 Last sold price
4 beds3 baths3,142 sq ft
7 South Meadow Ln, Oak Bluffs, MA 02557
$1517/sq ft
larger lot
12 years older

Rental earnings

Est. $4,354 per month, based on comparable rentals

This home is pending

The seller has accepted an offer, and this property is now .

Questions? Redfin partner agents are here to help

Typically responds in about 1 minute.

Nearby similar homes

$1,499,000

3 beds2.5 baths1,645 sq ft

7 Ploughshare Ln, Oak Bluffs, MA 02557

$1,140,000

4 beds2 baths2,059 sq ft

4 Rock Pond Rd, West Tisbury, MA 02575

$2,800,000

4 beds4.5 baths3,927 sq ft

44 Tiffany Dr, Oak Bluffs, MA 02557

$1,800,000

4 beds3 baths2,864 sq ft

18 Wood Duck Way, Edgartown, MA 02539

$639,000

Land— sq ft

52 Heath Hen Ln, Vineyard Haven, MA 02568

$1,175,000

3 beds1 bath998 sq ft

299 Daggett Ave Unit A, Vineyard Haven, MA 02568

Details provided by MLS PIN and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Mortgage resources

Open houses

Nearby open houses (2)

Around this home

Schools

Market insights

Property details

Sale and tax history for 308 South Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 308 South Rd

This home is pending

Questions? Redfin partner agents are here to help

Nearby similar homes

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