$45,000,000
7 Beds
12 Baths
14,780 sqft (on 4.90 acres)
18 Point Inner Way, Chilmark, MA 02535
Est. Mortgage $259,302/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 2012
4.9 acre lot
$3,045/sqft
Garage
Local Information
- Map ViewExplore the area around 18 Point Inner Way.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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 Details for 18 Point Inner Way
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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 |
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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 |
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Days on Market: 119 |
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Year Built Year Built: 2012 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
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Price List Price: $45,000,000Price Per Sqft: $3,045 |
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MLS Status: A |
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Direction & Address City: Chilmark |
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Listing Agent Listing ID: 44498 |
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Building Area Building Area: 14780 Square Feet |
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Lot Area: 4.9 Acres |
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Listing Agreement Type: E |
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BasementMls Number: 44498Water ViewWater View: Pond, D/Snd |
Around this home
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.
Market trends in Chilmark
Last updated August 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
40
1MoM
Home Value
Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.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 | |
0.39 | Single-Family Home | $5,250,000 | 09/03/26 | 4 | 3 | 2,746 | |
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 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.20 | $10,035,300 | 6 | 5.5 | 5,808 | Off Market | |
0.28 | $6,063,400 | 6 | 4.5 | 3,143 | Off Market | |
0.29 | $5,563,100 | 5 | 3 | 2,373 | Off Market | |
0.33 | $3,950,000 | 3 | 2 | 1,260 | For Sale | |
0.33 | - | - | - | - | Off Market | |
0.38 | $6,726,400 | 4 | 3.5 | 3,355 | Off Market | |
0.39 | $5,250,000 | 4 | 3 | 2,746 | Recently Sold | |
0.52 | $5,500,000 | 2 | 1 | 808 | For Sale | |
0.57 | $5,750,000 | 2 | 1.5 | 1,446 | Recently Sold | |
0.75 | $10,950,000 | 4 | 3.5 | 2,050 | For Sale | |
0.78 | - | - | - | - | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
May 25, 2026 Source: LINK #44498 | Listed For Sale | $45,000,000 |
Jul 9, 2010 Source: LINK #16988 | Sold | $7,400,000 |
Apr 11, 2009 Source: Agent Provided | ListingRemoved | $10,500,000 |
Mar 17, 2009 Source: Agent Provided | Listed For Sale | $10,500,000 |
| Year | Property tax | Tax assessment |
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| 2025 | $87,646 | $38,953,900 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Alyssa Halisky, Wallace & Co. Sotheby's
© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-21 02:08:26 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.
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Frequently asked questions about 18 Point Inner Way
- What is the estimated monthly payment for 18 Point Inner Way?Based on a $45,000,000 list price with 20% down at today's rates, the estimated monthly payment for 18 Point Inner Way in Chilmark, MA is approximately $265,190 (about $246,365 principal & interest, $18,750 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What are the closest schools to 18 Point Inner Way?The closest schools to 18 Point Inner Way in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
- Does 18 Point Inner Way have a pool?Yes, 18 Point Inner Way in Chilmark, MA has a pool.
- Does 18 Point Inner Way have laundry facilities?Yes, 18 Point Inner Way in Chilmark, MA has laundry facilities.
- How big is the lot at 18 Point Inner Way?The lot at 18 Point Inner Way in Chilmark, MA is about 4.9 acres.
- Does 18 Point Inner Way have a garage?Yes, 18 Point Inner Way in Chilmark, MA has a garage.
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.