205 South Rd, Chilmark MA 02575
Chilmark, MA 02575 • Chilmark
$5,650,000
$4,995,000
Est. $26,616/month
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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.
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Recently Sold Nearby
Property History
Market Insights
2
Price Changes
11.6%
Price Range
Property Timeline
Price Reduced
Jul 30, 2026
$4,995,000
$355,000
(-6.64%)
From $5,350,000 to $4,995,000 (-6.6%)
Price Reduced
May 14, 2026
$5,350,000
$300,000
(-5.31%)
From $5,650,000 to $5,350,000 (-5.3%)
Listed for Sale
Apr 3, 2026
$5,650,000
Original listing
Agent: Tina Miller
Office: Donnelly + Co.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/30/2026 | ↓ Price Reduced | $4,995,000 | $355,000 | - | From $5,350,000 to $4,995,000 (-6.6%) |
| 05/14/2026 | ↓ Price Reduced | $5,350,000 | $300,000 | - | From $5,650,000 to $5,350,000 (-5.3%) |
| 04/03/2026 | 🏠 Listed for Sale | $5,650,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $13,900 | $5,859 |
Financial Details
Annual Property Tax
$13,900
Tax Year 2025
Assessed Value
$5,859
Facts & Features
3 Car Garage
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1940
Living Area
5,402 sq ft
Lot Size
5.99 acres
Bedrooms
4
Full Baths
4
Half Baths
1
Total Rooms
9
Interior
Heating
Radiant, Heat Pump
Cooling
Heat Pump
Flooring
None
Appliances
Water Heater
Fireplace
None
Fireplaces
1
Basement
Full, Partially Finished
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Cape
Roof
None
Features
None
Pool
None
Spa
None
Fencing
Fenced/enclosed
Patio/Porch
None
Parking
Garage Spaces
3
Has Garage
Yes
Features
Detached
Total Spaces
11
Utilities
Electric
None
Water
Private
Sewer
Inspection Required For Sale
Gas
None
Other
None
Financial
Annual Tax
$13,900
Assessed Value
$5,859
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Dukes
Total market time (incl. prior listings)
122 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1940
Bedrooms
4
Full Bathrooms
4
Half Bathrooms
1
Living Area
5,402 sq ft
Total Rooms
9
Floor Layout
Interactive room guide
Floor Layout
Finished Area
5,402 sq ft above grade
FeaturesYes
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Water Heater
Interior Features:
Windows:
Basement:
Full, Partially Finished
Laundry:
Security:
Construction & Materials
Style:
Cape
Year Built:
1940
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Radiant, Heat Pump
Cooling:
Heat Pump
Hot Water:
Water Source:
Private
Sewer:
Inspection Required for Sale
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Fenced/Enclosed
Other Structures:
Lot Features:
Wooded, Cleared, Gentle Sloping
Road Surface:
Parking & Garage
Garage Spaces:
3
Total Parking Spaces:
11
Parking Features:
Detached
Special Features
Fireplaces:
1
Fireplace Type:
Community Amenities:
Nearby Schools
School District
Martha's Vineyard School District local
School Safety
2024-25
5.0%
Above Average
5.0%
Suspensions
1.3%
In-School
0.5% below state avg
Elementary Schools
3 schools
A
Chilmark Elementary School
2.8 mi
|
#88 of 824
|
Score: 59.8
Dropped 87 spots from last year
+1.6 above state avg
69 students
Less Diverse
Grades K-05
B
West Tisbury Elementary School
3.6 mi
|
#167 of 352
|
Score: 43.0
Dropped 58 spots from last year
-15.2 below state avg
321 students
Moderate
Grades PK-08
C-
Martha's Vineyard Public Charter School
4.6 mi
|
#299 of 346
|
Score: 38.0
Dropped 30 spots from last year
-20.2 below state avg
176 students
Moderate
College Ready Curriculum
Grades K-12
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Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$1,158
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
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Current Rate
$0/mo
+0.5% Rate
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Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
Chilmark
205 South Rd, Chilmark MA 02575
Chilmark, MA 02575
Listing Information
Listing Agent
Tina Miller
Listing Office
Donnelly + Co.
Office Phone
508-627-1022
Agent MLS ID
CN236935
Office MLS ID
AN6036
Listing Data Updated
Aug 3, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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