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18 Point Inner Way, Chilmark single family home — photo 1 of 53
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18 Point Inner Way

7112Sleeps 14

Chilmark

18 Point Inner Way

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Exceptional rental opportunity on Menemsha Pond. This stunning compound features a main house with six ensuite bedrooms, showcasing a remarkable first-floor primary suite with two full bathrooms. Two kitchens, equipped with top-of-the-line appliances, provide a luxurious culinary experience. Additional features include a home theater with massage chairs and expansive indoor and outdoor living spaces against the backdrop of breathtaking water views. Included with the main house is a large waterfront deck with outdoor Italian seating that can comfortably accommodate 20 people. There is an outdoor dining table that can accommodate 24 guests, as well as a large built in Kalamazoo grill and pizza oven, an outdoor wooden bar, an outdoor built in stone fire pit and two large built in Tucci umbrellas. The pool house serves as a haven of relaxation, featuring an indoor heated 10' X 30' pool and a spa surrounded by floor-to-ceiling sliding glass doors that seamlessly blend the interior with the exterior. Additional amenities include a sauna, steam room, wet bar, and guest bedroom. The second-floor is a full guest suite, including a large bedroom, washer and dryer, a living room and two spacious balconies. Perched atop the compound is a hilltop writer's cottage, offering panoramic views overlooking the pond. Also included on the property is an entertainment building including a large full gym with various cardio and weight machines by Technogym and Peloton. The gym features floor-to-ceiling windows providing scenic views. There is also an indoor basketball court with an NBA professional basketball shooting machine. Below is a 6 car garage with Porsche and Tesla electric car charging stations. Guests can also enjoy outdoor recreational activities with a tennis court that doubles as a pickle ball court with appropriate lines, and a large cedar jungle gym. The property includes a 115' deep-water dock with a boat house featuring numerous waterfront activities including paddle boards, kayaks, and wetsuits for added convenience. Additionally, three purpose-designed boats are available for use during the stay. Guests have the option to rent one, two, or all three:
Boat One is a 55-foot Novamarine BS160, custom made in Italy, equipped with 5 outboard Mercury Racing engines and significant customization (captain required). Boat Two is a Mastercraft X26, perfect for water skiing, wake surfing, wakeboarding, etc. The boat features a computer touch panel for creating a customizable surf wave behind the boat.
Boat Three is a Zodiac Open 7.0 speed boat, versatile for water skiing and well-suited for navigating open oceans with waves. This 26-foot boat is powered by a Yamaha 200 HorsePower outboard engine, offering both agility and stability on the water.
The nearby beaches offer delightful opportunities for sunbathing, swimming, and savoring the picturesque ocean views. Menemsha, a charming fishing village nestled in Chilmark, is celebrated for its delightful harbor, delicious seafood, and enchanting sunsets. From the property itself, guests can enjoy breathtaking views of Menemsha Pond, particularly at sunset, when warm hues paint the sky and cast reflections on the serene waters, creating a tranquil and visually captivating setting. The island plays host to a variety of events and activities, including farmers' markets, art fairs, and community gatherings. The lush green surroundings, invigorating coastal breezes, and overall sense of serenity make it an attractive destination for those in search of an escape. This rental opportunity guarantees an immersive, high-end escape where guests can unwind in a serene atmosphere, surrounded by the beauty of nature and the thoughtful luxury woven into every aspect of the property.

*Two week minimum, price upon request*

Wallace & Co. Sotheby’s International Realty attempts to accurately represent the Premises to the best of our ability. Our information is deemed reliable but not guaranteed. Opinions as to the condition of the Premises vary from individual to individual and are very subjective. We highly recommend that you personally view the property before signing the lease to verify the information in the advertised listing sheet. Be aware that numerous types of molds occur naturally on Martha’s Vineyard; some people may be sensitive to and have allergic reactions from the same. Any house built prior to 1978 may contain lead paint.

Bedrooms

Bedroom 1

Main House - First level: Primary suite, King Bed, (2) Full Private Baths

Bedroom 2

Main House - Second Level: King Bed, Private Bath

Bedroom 3

Main House - Second Level: (2) Queen Beds, Private Bath

Bedroom 4

Main House - Second Level: Queen Bed, Private Bath

Bedroom 5

Main House - Lower Level: Twin Bed, Crib, Private Bath

Bedroom 6

Main House - Lower Level: Queen Bed, Private Bath

Bedroom 7

Guest House - Second Level: King Bed, Private Bath

Amenities

Featured Amenities

  • Lawn / Garden Area
  • Pool - Heated
  • Waterfront
  • Outdoor Shower
  • Tennis Courts - Private
  • Hot Tub
  • AC - Central Air
  • Guest House

Indoor Amenities

  • Den
  • Exercise Equipment
  • Finished Basement
  • Fireplace
  • Garage Parking
  • Home Office / Study
  • Private - In Home Gym
  • Sauna
  • Sunroom
  • Wet Bar

General

  • Crib
  • Hair Dryer
  • High Chair
  • Iron/Ironing Board
  • Washer/Dryer
  • Vacuum

Linens

  • Linens - Provided

Kitchen And Dining

  • Bakeware
  • Beverage Refrigerator
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Additional Dishwasher
  • Food Processor
  • Gourmet Kitchen
  • Lobster Pot
  • Microwave
  • Mixer
  • Oven/Stove
  • Additional Oven/Stove
  • Pantry Items
  • Pizza Oven
  • Refrigerator
  • Toaster
  • Wine Fridge
  • Wet Bar - Outside

Entertainment

  • Media Room
  • Wireless Internet
  • Surround Sound System
  • TV - Cable

Outdoor Amenities

  • Hot Tub
  • Beach Chairs
  • Beach Toys
  • Beach Umbrella
  • Cooler
  • Dock
  • Driveway Parking
  • Patio
  • Balcony
  • Screened Porch
  • Deck
  • Grill - Gas
  • Kayak(s)
  • Life Jackets
  • Outdoor Dining Area
  • Outdoor Furniture
  • Outdoor Kitchen
  • Outdoor Fireplace
  • Pool House
  • Pool Toys

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October 2026

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Rates & Availability

May 2027 – August 2027

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Available BookedCheck-out day — available from middayCheck-in day — available until the afternoon

Rates and availability are subject to change and may not be current. Published rates do not include local & state taxes. Please contact your Wallace & Co. Sotheby’s International Realty agent to confirm current rates and availability.

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Location

Chilmark

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