For sale

$4,995,000

Est. $28,075/mo —

•

5,402

sq ft

205 South Rd, Chilmark, MA 02575

About this home

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, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

Single-familyProperty Type

1940Year Built

5.99 acresLot Size

$925Price/Sq.Ft.

3 garage spacesParking

Listed by Tina Miller • Donnelly + Co.

Listed by • Donnelly + Co.

Listing updated: Aug 3, 2026 at 03:07am

Redfin checked: a few seconds ago

•Source:MLS PIN #73495595

Payment calculator

$28,075 per month

Principal and interest$25,918

Property taxes

$1,158

HOA dues

Home insurance

$999

Utilities

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Around this home

Schools

K - 12
Preschool & daycare

Chilmark Elementary School

Public K-5 • Assigned • 2.7mi

8/10

West Tisbury Elementary School

Public PreK-8 • Assigned • 3.6mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 6.6mi

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

Offer insights

205 South Rd · $4,995,000

Strong offer

$4.89M and above

75% chance or better to win

Why $4.89M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 63 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Nine total rooms
Full, partially finished basement
One fireplace

Bathrooms
Four full bathrooms
One half bathroom
Master bathroom present

Kitchen
Water heater listed among appliances

Heating & cooling
Radiant heating
Heat pump heating and cooling

Sale and tax history for 205 South Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$11,338 (+6.5%)

$1,174,100 + $3,136,800

$4,310,900

2022

$10,643 (+7.7%)

$1,089,900 + $2,684,100

$3,774,000

2021

$9,886 (+3.6%)

$1,089,900 + $2,307,300

$3,397,200

2020

$9,547 (+22.1%)

$1,068,500 + $2,269,500

$3,338,000

2019

$7,816 (+4.7%)

$1,068,500 + $1,645,400

$2,713,900

2018

$7,463 (+3.2%)

$1,068,500 + $1,645,400

$2,713,900

2017

$7,235 (−0.5%)

$1,068,500 + $1,631,300

$2,699,800

2016

$7,274 (+2.4%)

$1,068,500 + $1,615,500

$2,684,000

2015

$7,102

$1,068,500 + $1,631,700

$2,700,200

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

5.99 Acres

Year renovated

—

Finished Sq. Ft.

—

Unfinished Sq. Ft.

—

Total Sq. Ft.

—

Year built

—

Style

Other

County

Dukes County

APN

3566352

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

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

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Chilmark, MA • 02575

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

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Provided by Shadowmap

Redfin Estimate for 205 South Rd

$4,688,927

$306K under list price of $5.00M

Nearby comparable homes

The Redfin Estimate uses 5 recent nearby sales, priced between $1.9M 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
$245/sq ft
smaller lot
62 years newer
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
$96/sq ft
smaller lot
46 years newer
SOLD NOV 21, 2025
$2,500,000 Last sold price
5 beds4.5 baths4,982 sq ft
79 David Ave, Vineyard Haven, MA 02568
$423/sq ft
smaller lot
47 years newer
SOLD DEC 10, 2025
$2,250,000 Last sold price
4 beds3.5 baths3,014 sq ft
10 Wood Duck, Oak Bluffs, MA 02557
$178/sq ft
smaller lot
40 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
$336/sq ft
smaller lot
47 years newer

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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

See this home in person

Nearby open houses (1)

Around this home

Schools

Offer insights

Property details

Sale and tax history for 205 South Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 205 South Rd

Early Access listings

Nearby similar homes

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