INQUIRE ABOUT THIS LISTING

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Waterview Chilmark

$16,000 - $16,000/wk

Chilmark Waterview Retreat with Private Dock

Experience the best of Chilmark living in this beautifully appointed four-bedroom, three-bath home with sweeping waterviews and a private dock on Chilmark Pond. Designed for effortless indoor-outdoor living, the home features a spacious deck stretching the full width of the house—perfect for sunset gatherings, alfresco dining, or simply taking in the tranquil pond views.

The airy, open-concept living, dining, and kitchen area showcases exposed beams, cathedral ceilings, and a stylish sleep loft above the kitchen—infusing the space with light and character. Multiple sets of doors connect the interior to the expansive deck, creating a seamless flow for entertaining and relaxation.

The private primary suite enjoys its own wing with direct deck access, while the guest bedrooms are thoughtfully set apart for privacy. The home’s interiors exude a casually sophisticated Vineyard charm—bright, comfortable, and impeccably maintained. Additional amenities include central air conditioning, an outdoor shower, and extra loft sleeping areas for overflow guests.

With deeded south shore beach access by small boat or kayak across the pond, this property offers the rare combination of waterviews, privacy, and direct connection to one of Chilmark’s most beautiful beaches.

At a glance

Listing # 115114
Town Chilmark
Sq Ft 1952
Bedrooms 4
Sleeps 8
First Floor Bedroom
Yes
Baths 2
Priv|Assoc Beach
Yes

AVAILABILITY & RATES

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Turnover day: Saturday
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Owners are currently updating 2026 rates from 2025 and are subject to change. Please call 508.696.9999 or email us to confirm.

RATES

From
To
Weekly
16,000

MORE DETAILS

GENERAL INFO

  • Listing # 115114
  • Check in from 4:00 PM
  • Check out by 10:00 AM
  • Town: Chilmark
  • SQ FT: 1952
  • Bedrooms: 4
  • Sleeps: 8
  • Baths: 2
  • Water View: Yes
  • Priv|Assoc Beach: Yes
  • Beach Description: Atlantic over Pond & Town Beaches
  • Air Conditioning: Central AC
  • No Smoking
  • No Pets Accepted

BEDROOM CONFIGURATION

  • 1 King Bed(s)
  • 2 Queen Bed(s)
  • 1 Double Bed(s)
  • 3 Single Bed(s)
  • BR 1 - King with private bath, 1st Floor
  • BR 2 - Twin, 1st Floor
  • BR 3 - Double, 1st Floor
  • BR 4 - 2 Queens & 2 Twins, Loft

KITCHEN

  • Dishwasher
  • Microwave
  • Coffee Maker
  • Toaster
  • Blender
  • Lobster Pot
  • Food Processor

INTERNET / ELECTRONICS

  • High Speed Internet
  • 2 TVs
  • Cable TV
  • DVD
  • 2 DVDs

OUTDOOR

  • Outside Shower
  • Deck
  • Deck Furniture
  • BBQ Charcoal
  • BBQ Gas
  • Beach Equipment
  • Enclosed Outside Shower

HOUSEKEEPING

  • Washer
  • Dryer
  • Iron
  • Ironing Board
  • Vacuum Cleaner
  • Linens Provided

5 Osprey Lane, Chilmark

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