139 Chappaquiddick Road, Edgartown MA 02539
Edgartown, MA 02539 • Chappaquiddick
$12,250,000
Est. $63,774/month
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About this home
You truly can have it all—just over a mile from the Chappaquiddick Ferry and the shops and restaurants of Edgartown Village, yet set along one of the most spectacular stretches of beach, with a 190’ private dock with mooring and sweeping views across Edgartown Outer Harbor to the iconic Edgartown Lighthouse. A gentle slope leads to the sandy shore, where days unfold along the pristine waters of the harbor. Inside, casual elegance defines the home, with a seamless blend of gracious formal spaces and inviting areas for relaxed gatherings. An enclosed porch opens onto a spacious deck overlooking the harbor, creating the perfect setting to take in picture-worthy sunsets, the beloved Fourth of July fireworks display, and the ever-changing scenery. The grounds are equally captivating, made even more exceptional by the inclusion of 75 Landing Place Road and a beloved clay tennis court framed by sweeping water views. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Aug 13, 2026
$12,250,000
Original listing
Agent: Katie Donahue & Rachel Serwa Group
Office: Sandpiper Realty, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/13/2026 | 🏠 Listed for Sale | $12,250,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $19,582 | $7,895,941 |
Financial Details
Annual Property Tax
$19,582
Tax Year 2026
Assessed Value
$7,895,941
Facts & Features
1 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1938
Living Area
4,855 sq ft
Lot Size
5.03 acres
Bedrooms
7
Full Baths
4
Total Rooms
17
Interior
Heating
Forced Air
Cooling
Central Air
Flooring
None
Appliances
None
Fireplace
None
Fireplaces
2
Basement
Partial, Crawl Space, Interior Entry
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Other (see Remarks)
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Garage Spaces
1
Has Garage
Yes
Features
Detached
Total Spaces
7
Utilities
Electric
None
Water
Private
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$19,582
Assessed Value
$7,895,941
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Dukes
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1938
Bedrooms
7
Full Bathrooms
4
Living Area
4,855 sq ft
Total Rooms
17
Floor Layout
Interactive room guide
Floor Layout
Finished Area
4,855 sq ft above 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:
Partial, Crawl Space, Interior Entry
Laundry:
Security:
Construction & Materials
Style:
Other (See Remarks)
Year Built:
1938
Structure Type:
Exterior Materials:
Roof:
Foundation:
Other
Heating, Cooling & Utilities
Heating:
Forced Air
Cooling:
Central Air
Hot Water:
Water Source:
Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Cleared, Gentle Sloping, Level
Road Surface:
Parking & Garage
Garage Spaces:
1
Total Parking Spaces:
7
Parking Features:
Detached
Special Features
Fireplaces:
2
Fireplace Type:
Waterfront:
Yes
Waterfront Type:
Waterfront, Ocean, Harbor, Dock/Mooring, Private, Harbor, Ocean, Direct Access, 0 to 1/10 Mile To Beach, Beach Ownership(Private,Public)
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Nearby Schools
School District
Edgartown School District local
School Safety
2024-25
0.0%
Very Low (Safest)
5.5% below state avg
Elementary Schools
1 school
B+
Edgartown Elementary School
1.9 mi
|
#121 of 352
|
Score: 47.3
Improved 45 spots from last year
-10.9 below state avg
357 students
Diverse
Rising School
Grades PK-08
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Monthly Payment Calculator
Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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After down payment
Total Interest
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Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$1,632
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
$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
Chappaquiddick
139 Chappaquiddick Road, Edgartown MA 02539
Edgartown, MA 02539
Listing Information
Listing Agent
Katie Donahue & Rachel Serwa Group
Listing Office
Sandpiper Realty, Inc.
Office Phone
508-627-3737
Agent MLS ID
TM362163
Office MLS ID
AN9490
Listing Data Updated
Aug 13, 2026 11:49 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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