Chappy Waterfront Estate with 140-Foot Deepwater Dock & Guest House

8 Bedrooms7.0 Baths16 GuestsNo PetsHOUSE in Edgartown
Guests

Property Details

Experience the ultimate Vineyard getaway at this extraordinary Chappy waterfront estate. Complete with a 140-foot deepwater dock, a five-bedroom main house and a three-bedroom guest house, this property offers a rare blend of seclusion, luxury and recreation, just minutes from Edgartown village yet worlds apart in privacy and tranquility.

The main residence is architecturally striking yet warm and welcoming. Nearly every room enjoys sweeping views of Nantucket Sound, with fir floors, shiplap walls and a large porch supported by locust posts. The home features five bedrooms, including a second-floor primary suite with panoramic water views. A fully equipped gym with steam shower and sauna is on the lower level, and the expansive great room with large dining table makes entertaining effortless.

Rolling lawns extend to a private sandy beach, perfect for swimming, paddle boarding or relaxing on one of two floating platforms at the dock, with a front-row seat to yacht regattas and sunsets. The deepwater dock accommodates vessels with a 6-8 ft draft.

The guest house is privately set apart with its own kitchen, living area and three bedrooms, ideal for extended family or guests.

Located across from the Royal and Ancient Chappaquiddick Links, and minutes to downtown Edgartown's shops and restaurants.

Sleeping Arrangements

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Bedroom 5

2 Single Beds

Bedroom 6

1 Queen Bed

Bedroom 7

1 Single Bed

Bedroom 8

2 Single Beds

Amenities

Airbnb Only

  • Boat Slip
  • Exercise Equipment
  • Outdoor Dining Area
  • Outdoor Furniture
  • Outdoor Shower
  • Sea View

Entertainment

  • Ping Pong Table

Features

  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Fitness Room / Equipment
  • Internet - Wifi
  • Linens Provided
  • Parking
  • Washing Machine

Flexcation

  • Smart TV

Kitchen

  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster

Location

  • Downtown
  • Water View
  • Waterfront

Outdoor

  • Garden
  • Veranda

Pool

  • Sauna

Availability

2026
November 2026
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Location

37 North Neck Road
Edgartown, MassachusettsOpen in Maps

Policies

Cancellation Policy

CANCELLATION POLICY: In the event of a cancellation Tenant must notify Portfolio Properties in writing. Portfolio Properties will then make every effort to re-rent this property for the lease rental period. If the property is re-rented for the full rental period at the amount specified in this lease document, a refund will be issued less 15% of the total amount of the lease to be retained by Portfolio Properties. In the event Portfolio Properties is unable to re-rent the property, the tenant agrees to be responsible for the full amount of the rental as outlined in the payment schedule. If Portfolio Properties is able to re-rent the property for less than the full rental amount, the tenant will be responsible for 15% of the original rental amount and any difference between the original rate and the new rental rate.

from $2857.14 / night