308 South Road, Chilmark MA 02535
Chilmark, MA 02535 • Chilmark
$7,350,000
Est. $38,891/month
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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.
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Property History
Market Insights
Property Timeline
Status: Active under contract
Aug 4, 2026
Active → Active Under Contract
Pending Sale
Aug 3, 2026
Offer accepted, sale pending
Listed for Sale
Feb 18, 2026
$7,350,000
Original listing
Office: Wallace & Co. Sotheby's International Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/04/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 08/03/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 02/18/2026 | 🏠 Listed for Sale | $7,350,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $18,310 | $8,030,800 |
Financial Details
Annual Property Tax
$18,310
Tax Year 2026
Assessed Value
$8,030,800
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1999
Living Area
3,490 sq ft
Lot Size
0.0000
Bedrooms
4
Full Baths
4
Half Baths
1
Total Rooms
10
Interior
Heating
Forced Air, Heat Pump, Active Solar, Ductless
Cooling
Central Air, Heat Pump, Active Solar, Ductless
Flooring
None
Appliances
None
Fireplace
None
Basement
Full, Walk-out Access, Interior Entry
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Cape
Roof
None
Features
None
Pool
None
Spa
None
Fencing
Fenced/enclosed
Patio/Porch
None
Parking
Features
None
Total Spaces
7
Utilities
Electric
None
Water
Private
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$18,310
Assessed Value
$8,030,800
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
None
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)
181 days
Property Overview
Property Type
Single Family Residence
Listing Type
Sale Pending
Year Built
1999
Bedrooms
4
Full Bathrooms
4
Half Bathrooms
1
Living Area
3,490 sq ft
Total Rooms
10
Levels
Multi/Split
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,553 sq ft above grade
937 sq ft below grade
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:
Interior Features:
Windows:
Basement:
Full, Walk-Out Access, Interior Entry
Laundry:
Security:
Construction & Materials
Style:
Cape
Year Built:
1999
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Forced Air, Heat Pump, Active Solar, Ductless
Cooling:
Central Air, Heat Pump, Active Solar, Ductless
Hot Water:
Water Source:
Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Fenced/Enclosed
Other Structures:
Lot Features:
Sloped
Road Surface:
Parking & Garage
Total Parking Spaces:
7
Parking Features:
Special Features
Waterfront:
Yes
Waterfront Type:
Waterfront, Navigable Water, Pond, Dock/Mooring, Frontage, Direct Access, Private, Beach Access, Ocean, Direct Access, 0 to 1/10 Mile To Beach, Beach Ownership(Private,Deeded Rights)
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Nearby Schools
School information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
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
$1,526
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
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
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
308 South Road, Chilmark MA 02535
Chilmark, MA 02535
Listing Information
Listing Agent
Rose Ryley
Listing Office
Wallace & Co. Sotheby's International Realty
Office Phone
508-627-3313
Agent MLS ID
CT005178
Office MLS ID
AN9542
Listing Data Updated
Aug 18, 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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