18 Point Inner Way, Chilmark, MA 02535
Property image
Property image
FOR SALE
3D VIEW
4.9 ACRES

18 Point Inner Way
Chilmark, MA 02535

  • 7 Beds
  • 12 Baths
  • 14,780 sqft (on 4.90 acres)

$45,000,000

Est. Mortgage $246,369/mo*

$45,000,000

Est. Mortgage $246,369/mo*
7 Beds
12 Baths
14,780 sqft
(on 4.90 acres)

Local Information

  • Map ViewExplore the area around 18 Point Inner Way.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, and outdoor shower. Set just beyond, the pool house is designed as a private wellness retreat, featuring a heated indoor pool, spa, sauna, steam room, and cold plunge, all surrounded by retractable walls of glass that seamlessly blend indoor and outdoor living. The first floor also includes a full bath, kitchenette, laundry area, and spacious enclosed porch. The second level offers a luxurious guest suite complete with a bedroom, living room, spa-inspired bath with dual showers and soaking tub, and two private balconies overlooking the pond. The estate also includes an impressive barn-style entertainment pavilion with a professionally designed fitness center featuring floor-to-ceiling windows and scenic pond views. Adjacent is a sprawling recreation lounge designed for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage ideal for luxury vehicles, boating equipment, and recreational storage. Completing the compound are a private tennis court, hilltop writer’s cottage with panoramic water views, and a charming boathouse by the dock for waterfront gear. An unparalleled modern waterfront retreat in one of Martha’s Vineyard’s most exclusive settings.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
$3,045
Listed
57 days ago

Home Details for 18 Point Inner Way

Interior Features

Interior Details
Basement: See Floor PlansNumber of Rooms: 25
Beds & Baths
Number of Bedrooms: 7Main Level Bedrooms: 1Number of Bathrooms: 13Number of Bathrooms (full): 11Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 14780 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes - 2 kitchens in main house, Washer: Yes - (Laundry room in main house and pool house)
Heating & Cooling
Heating: GFHANo CoolingHas HeatingHeating Fuel: GFHA
Fireplace & Spa
Fireplace: 1
Windows, Doors, Floors & Walls
Flooring: 3
Levels, Entrance, & Accessibility
Floors: 3
View
Has a ViewView: Pond, D/Snd

Exterior Features

Exterior Home Features
Other Structures: Dock, Boat House, 1, 927 sq. ft. Barn (Gym and Recreation space), Tennis Court, Writer's Cottage, 6-Car Garage, Storage Shed.Exterior: PvtBch, Deck, Garden, Gym, H/Tub, Tennis, P/Pool, ScrPorch, Porch, Patio, WViewsFoundation: Full foundationGarden
Parking & Garage
No CarportHas a GarageNo Attached GarageParking: Private stone driveway. 6-Car Garage
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: 57

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $45,000,000Price Per Sqft: $3,045

Active Status

MLS Status: A

Location

Direction & Address
City: Chilmark

Agent Information

Listing Agent
Listing ID: 44498

Building

Building Area
Building Area: 14780 Square Feet

Lot Information

Lot Area: 4.9 Acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 44498Water ViewWater View: Pond, D/Snd
Last check for updates: about 21 hours ago
Listing courtesy of Alyssa Halisky
Wallace & Co. Sotheby's
Source: LINK, MLS#44498
Also Listed on MLS PIN, MLS PIN, LINK.

Market trends in Chilmark

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
31
4
MoM

Price History for 18 Point Inner Way

DatePriceEventSource
05/25/2026$45,000,000Listed For SaleLINK #44498
07/09/2010$7,400,000Sold
LINK #16988
04/11/2009$10,500,000ListingRemovedAgent Provided
03/17/2009$10,500,000Listed For SaleAgent Provided

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Property Tax and Assessment

Year2025
Tax$87,646
Assessment$38,953,900
Home facts updated by county records

Comparable Sales for 18 Point Inner Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.28
Single-Family Home
$5,900,000
10/31/25
6
4.5
3,143
0.38
Single-Family Home
$6,550,000
11/14/25
4
3.5
3,355
0.57
Single-Family Home
$5,750,000
04/10/26
2
1.5
1,446
0.92
Single-Family Home
$10,500,000
03/12/26
4
2.5
3,200
1.93
Single-Family Home
$6,650,000
03/17/26
5
4.5
5,000
2.76
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
2.87
Single-Family Home
$7,289,000
10/15/25
4
5
3,777
1.81
Single-Family Home
$2,550,000
10/02/25
3
2
1,524
2.78
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
3.14
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044

Nearby homes

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Assigned Schools

These are the assigned schools for 18 Point Inner Way.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chilmark

At least 2 Trulia users voted on each feature.
  • 100 % Say there's wildlife

  • 100 % Say there are community events

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 78 % Say neighbors are friendly

  • 75 % Say it's dog friendly

  • 75 % Say people would walk alone at night

  • 67 % Say parking is easy

  • 67 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 43 % Say there's holiday spirit

  • 33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Elaine V.
    "I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"

LGBTQ Local Legal Protections

Alyssa Halisky, Wallace & Co. Sotheby's
© 2026 LINK, All Rights Reserved. Data last updated: 2026-07-20 10:14:46 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.
18 Point Inner Way, Chilmark, MA 02535 is a 7 bedroom, 13 bathroom, 14,780 sqft single-family home built in 2012. This property is currently available for sale and was listed by LINK on May 25, 2026. The MLS # for this home is MLS# 44498.