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139 Chappaquiddick Road and 75 Landing Place Road

$12,250,000

Chappy, Edgartown, MA 02539

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7 beds

4 baths

17 rooms

4,855 SqFt

MLS #44777

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, highlighted by a beloved clay tennis court framed by water views. Cherished by the same family for generations, this extraordinary waterfront compound is a truly special place.

Property highlights

Unfurnished

Tennis Court

Private Beach

Public Beach

Water Views

Porch

Hot Tub

Garden

Deck

Harbor View

Property Details

Association Fee:
Association Fee Includes:
Basement:
Partial basement under kitchen with built-in storage and work bench.
Fireplace Features:
2 - wood burning
Flooring:
Wood, Tile
Foundation Types:
Partial basement and crawl space.
Frontage Type:
Bay/Harbor
Heating:
GFHA
Interior Features:
A,AC,Ins,Irr,OShFloor 1: Upon entry, you are welcomed into a fully equipped kitchen that flows into the main living areas of the home, including a formal living and dining space. A built-in bar area, with an ice machine and refrigerator, sits just outside the enclosed porch, which offers ample space for both dining and relaxation, overlooking a large back deck and Edgartown Harbor. Two bedroom wings, each with three bedrooms and a full bath. A full bath with exterior access to the tennis court and outdoor shower.Floor 2: Private staircase to the primary suite, which boasts water views, an ensuite bathroom, and a large walk-in closet. A separate spiral staircase brings you to the "cupola," perfect as an office or sitting room with expansive water views. Two large attics with built-in storage.
Link MLS Comments:
From Chappy Ferry, take Chappaquiddick Road for roughly a mile, #139 is on the left.
Lot Features:
Lush and well manicured
Parking Features:
Plenty
Possible Use:
Assessed Building Value:
2800800.00
Assessed Land Value:
5095141.00

Price History

August 12, 2026
$12,250,000

Tax Information

This property was most recently assessed in 2026. It has been assessed at a value of $7,895,941. The annual tax responsibility for this property is $19,582.

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