SOLD OCT 6, 2026

Sold on oct 2026

$4,550,000

•

5,402

sq ft

205 South Rd, Chilmark, MA 02575

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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

$842Price/Sq.Ft.

3 garage spacesParking

Listed by Tina Miller • Donnelly + Co.

Listed by • Donnelly + Co.

Bought with Non Member • Non Member Office

Redfin checked: 2 minutes ago

•Source:MLS PIN #73495595

Redfin Estimate

$5,061,519

$512K since sold in October 2026$639K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 30% higher than the average sale price ($3.89M) of 5 comparable homes.

SOLD SEP 18, 2026
$6,500,000
A
4 beds4.5 baths3,490 sq ft
308 South Rd, Chilmark, MA 02535
SOLD SEP 3, 2026
$5,250,000
B
4 beds3 baths2,746 sq ft
21 Eliot Ave, Chilmark, MA 02535
SOLD AUG 5, 2026
$2,013,500
C
4 beds3.5 baths2,428 sq ft
35 Nats Farm Ln, West Tisbury, MA 02575
SOLD AUG 27, 2026
$2,800,000
D
4 beds3.5 baths2,515 sq ft
300 North Rd/18 Belhaven Way, Chilmark, MA 02535
SOLD MAR 30, 2026
$2,900,000
E
4 beds4 baths5,165 sq ft
63 Bayes Hill Rd, Oak Bluffs, MA 02557

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Market trends in 02535, MA

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

94.0%

2.5% MoM

Median sale price

$5.2M

$2M MoM

Avg. days on market

43d

0 days MoM

Recently sold homes

1 MoM

New listings for sale

$1,995,000
4 beds3 baths1,918 sq ft
25 Fulling Mill Rd, Chilmark, MA 02535
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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

—

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.

Property details

Parking

Parking Information
Has Garage
# of Garage Spaces: 3
# of Covered Spaces: 3
Open Parking Spaces: 8
Parking Spaces: 11
Parking Features: Detached

Interior

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Basement Information
Basement: Full, Partially Finished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1

Appliances
Appliances: Water Heater

Interior Features
# of Rooms (Total): 9

Exterior

Building Information
Building Area (Total): 5,402
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Fencing: Fenced/Enclosed

Property Information
PropertySubType: Single Family Residence
Above Grade Finished Area: 5402
ADU: N

Lot Information
Lot Size (Acres): 5.99
Lot Features: Wooded, Cleared, Gentle Sloping
Waterfront Features: Ocean, 3/10 to 1/2 Mile To Beach, Beach Ownership(Deeded Rights)

Financial

Tax Information
Tax Annual Amount: $13,900
Tax Year: 2025

Utilities

Utility Information
Sewer: Inspection Required for Sale
Water Source: Private

Heating & Cooling
Has Heating
Has Cooling
Heating: Radiant, Heat Pump
Cooling: Heat Pump

Location

Location Information
Directions: Heading Up-Island, 205 South Rd will be on your right. PROPERTY IS OCCUPIED. Please NO drive bys.
UnparsedAddress: 205 South Rd, Chilmark MA 02575

Community Information
Senior CommunityYN: No

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 5.99 acres
Style: Other
Year Built: —
Year Renovated: —
County: Dukes County
APN: 3566352

Home facts updated by county records on Jul 19, 2023

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

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

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

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$4.81M – $5.82M

Sell confidently with a local market expert in Chilmark.

Nearby similar homes

$3,790,000

7 beds4.5 baths4,464 sq ft

31 Josiah Sachem Way, West Tisbury, MA 02575

$2,999,000

3 beds3.5 baths3,082 sq ft

53 Stoney Hill Rd, West Tisbury, MA 02575

$5,900,000

7 beds4.5 baths6,921 sq ft

19 Locust Ln, Aquinnah, MA 02535

$1,800,000

4 beds3 baths2,864 sq ft

18 Wood Duck Way, Edgartown, MA 02539

$2,195,000

3 beds2 baths2,510 sq ft

26 Bijahs Way, Chilmark, MA 02535

$1,095,000

3 beds1 bath998 sq ft

299 Daggett Ave Unit A, Vineyard Haven, MA 02568

New listings for sale in 02535

$1,995,000

4 beds3 baths1,918 sq ft

25 Fulling Mill Rd, Chilmark, MA 02535

Home values near 205 South Rd

Data from public records.

Address	Redfin Estimate
218 South Rd, Chilmark, MA - Beds \| - Baths \| - Sq. Ft.	—
195 South Rd, Chilmark, MA - Beds \| - Baths \| - Sq. Ft.	—

Address	Redfin Estimate
187 South Rd, Chilmark, MA - Beds \| - Baths \| - Sq. Ft.	$1,030,020
214 South Rd, Chilmark, MA - Beds \| - Baths \| - Sq. Ft.	—

Address	Redfin Estimate
181 South Rd, Chilmark, MA 5 Beds \| 3.5 Baths \| 2656 Sq. Ft.	$2,753,737
182 South Rd, Chilmark, MA 4 Beds \| 4 Baths \| 3400 Sq. Ft.	$3,829,313

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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205 South Rd, Chilmark, MA 02575

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About this home

Redfin Estimate

Market trends in 02535, MA

Homeowner tools

Sale and tax history for 205 South Rd

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Other

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02535

Home values near 205 South Rd

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