Waterfront home beside a harbor dotted with sailboats, seen from above.
Aerial view of a coastal home among trees, with a dock, boats, and ocean beyond.
Aerial view of waterfront homes along a boat-filled harbor, with the ocean beyond.
Aerial view of a waterfront-adjacent property beside a sheltered harbor dotted with boats.
Aerial view of a modern home beside a boat-filled harbor at sunset.
Modern home entrance with glass doors, broad concrete steps, and purple hydrangeas.
Open living room with white sofas, a modern fireplace, and floor-to-ceiling windows overlooking the water.
Living room with white sofas and floor-to-ceiling windows overlooking the water.
Modern living room with blue sofas and floor-to-ceiling windows overlooking a leafy garden.
Living room with white sofas, a glass-railed mezzanine, and expansive windows overlooking greenery.
Double-height living room with a glass-railed mezzanine, fireplace, white sofas and woven pendant lights.
Sunroom with floor-to-ceiling windows, a wood-paneled ceiling, and woven lounge seating.
Furnished glass-walled sunroom with a wood ceiling, wicker seating, foosball table, and waterfront view.
Open-plan dining room with a long wooden table, sculptural island, and glass partitions.
Modern kitchen dining nook with a curved blue banquette and large windows overlooking trees.
Modern white kitchen with dark stone counters, glass shelving, and a dining area beyond.
Modern kitchen with marble island and gas cooktop, overlooking the water through large windows.
Living room with floor-to-ceiling garden windows, a white sectional, and a blue accent wall.
Living room with built-in media shelving and a black leather chair beside glass doors.
Dining room with a long wooden table overlooking a patio and water through expansive windows.
Bright living room with blue seating, a sculptural wood coffee table, curved staircase, and tall garden-facing windows.
Living room with a white sofa and armchair facing broad windows overlooking the water.
Indoor recreation room with a ping-pong table, basketball hoop, and tall windows overlooking trees.
Wood-paneled recreation room with an air hockey table, basketball hoop, and golf clubs.
Wood-paneled recreation room with an air hockey table, art counters, and an open door to the lawn.
Stone-clad home with an open garage revealing a wood-paneled recreation room and basketball hoop.
Home gym with weight machines and a dramatic veined stone wall.
Home gym with floor-to-ceiling windows, cardio equipment, a punching bag, and dumbbells.
Indoor swimming pool in a marble room with glass walls and views of a sunny lawn.
Indoor hot tub in a wood-paneled spa room with large windows overlooking greenery.
Indoor hot tub in a cedar-paneled room, with a swimming pool visible through glass doors.
Cedar sauna with tiered benches, a wooden bucket and ladle, and a high window overlooking greenery.
Furnished wood-paneled bedroom with a colorful quilted bed beside sliding glass doors overlooking a lawn.
Bedroom with a woven-frame bed and floor-to-ceiling windows overlooking greenery and water.
Modern sitting area with a white chaise lounge facing floor-to-ceiling windows overlooking a garden.
Living room with floor-to-ceiling windows overlooking a green yard and a glimpse of water.
Bright bedroom with floral wallpaper, colorful pillows, and tall windows opening onto a deck.
Bathroom with a glass-enclosed tub and shower, pale stone vanity, and bright pink towels.
Bedroom with blue-and-white bedding, a vaulted ceiling, and tall windows overlooking trees.
Bathroom with a dark marble walk-in shower, glass enclosure, and glossy wood doors.
Modern hallway with a glass-and-metal staircase and polished stone floor.
Modern bedroom with a white single bed, gray chair, colorful artwork, and a window overlooking greenery.
Home theater with rows of black leather recliners and a large projection screen.
Modern white kitchen with a large stone-topped island and suspended glass shelves.
Modern open-riser staircase with patterned metal treads and a glass railing.
Modern hallway with light wood floors, a large orange abstract painting, and bookshelves at the far end.
Wood-paneled bedroom with a vaulted ceiling, writing desk, and bay views through large windows.
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Price Upon Request

18 Point Inner Way

7 Beds 13 Baths

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Description

An Extraordinary Private Waterfront Estate on Menemsha Pond

An exclusive Chilmark luxury vacation rental offering resort-style amenities, exceptional privacy, and an unparalleled Martha's Vineyard experience.

An extraordinary waterfront estate on Menemsha Pond, this world-class compound offers an unparalleled luxury rental experience in the heart of Chilmark. Designed for elevated coastal living, the property seamlessly blends sophisticated architecture, resort-style amenities, and breathtaking panoramic water views across an exceptional multi-structure retreat.

The main residence features six beautifully appointed ensuite bedrooms, highlighted by a spectacular first-floor primary suite with dual spa-inspired bathrooms. Thoughtfully designed for both grand entertaining and intimate relaxation, the home offers expansive indoor and outdoor living spaces, a state-of-the-art theater with massage seating, and two designer kitchens outfitted with premium appliances for a truly elevated culinary experience.

Overlooking the water, the expansive waterfront entertaining terrace is designed to host on a remarkable scale. Italian outdoor furnishings accommodate up to 20 guests, while a stunning dining table seats 24 for unforgettable al fresco evenings. Additional outdoor features include a built-in Kalamazoo grill and pizza oven, handcrafted wooden bar, custom stone fire pit, and oversized Tuuci umbrellas—all framed by the beauty of Menemsha Pond.

The resort-style pool house is a private wellness sanctuary featuring an indoor heated 10’ x 30’ pool and spa surrounded by dramatic floor-to-ceiling retractable glass walls that create a seamless indoor-outdoor experience. Additional amenities include a sauna, steam room, wet bar, guest suite, and an expansive second-floor guest residence complete with a spacious bedroom, living room, laundry, and two private balconies.

Perched above the estate, a secluded writer’s cottage captures sweeping hilltop views over the pond, offering an inspiring and tranquil retreat.

Designed with recreation and entertainment in mind, the property also includes a dedicated entertainment pavilion featuring a fully equipped luxury gym with Technogym and Peloton equipment, floor-to-ceiling windows, and an indoor basketball court with an NBA-caliber professional shooting machine. Below, a six-car garage includes Porsche and Tesla charging stations.

Outdoor amenities continue with a tennis court lined for pickleball, a large cedar jungle gym, and a private 115-foot deep-water dock complete with a boathouse and an impressive collection of waterfront equipment including paddleboards, kayaks, wetsuits, and more.

For guests seeking the ultimate on-the-water experience, three custom boats are available for use during your stay:

• A 55-foot custom Italian Novamarine BS160 with five Mercury Racing outboard engines (captain required)
• A MasterCraft X26 designed for wake surfing, water skiing, and wakeboarding with customizable wave technology
• A Zodiac Open 7.0 speed boat powered by a Yamaha 200 HP engine, ideal for coastal cruising and watersports

Located moments from the beaches and the iconic fishing village of Menemsha, guests can enjoy renowned seafood, local markets, art fairs, boating, and some of Martha’s Vineyard’s most spectacular sunsets. From nearly every vantage point on the property, sweeping sunset views over Menemsha Pond create an atmosphere of absolute serenity and coastal sophistication.

This exceptional estate presents a rare opportunity to experience Martha’s Vineyard at the highest level—where privacy, luxury, wellness, and waterfront living come together in one unforgettable destination.

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Location

18 Point Inner Way, Chilmark , MA 02535

Status

For Lease

Property Amenities

Interior
Total Bedrooms: 7
Half Bathrooms: 2
Full Bathrooms: 11
Area & Lot
Water Frontage Menemsha Pond
Status For Lease
Exterior
Garage Space 6
Aerial view of a coastal home among trees, with a dock, boats, and ocean beyond.

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Thank you for your interest in 18 Point Inner Way, Chilmark , MA 02535. We are reviewing your request and will be in touch shortly!
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Island Queen ferry crosses the harbor beyond a wooden pier, with a sailboat nearby.

The Agency Martha’s Vineyard

CONTACT DETAILS

(508) 627-7320

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OFFICE 205 UPPER MAIN ST EDGARTOWN MA 02539 PO BOX 275 EDGARTOWN MA 02539