Welcome to 18 Homeward Way — a peaceful Chilmark retreat tucked off scenic North Road, just minutes from the storied fishing village of Menemsha. This rare 15-acre offering includes two buildable parcels, creating an extraordinary opportunity for a Vineyard compound. The impeccably maintained residence, built in 1986, radiates classic Vineyard charm. Its thoughtful single-level layout fosters both privacy and connection, with sunlit gathering spaces balanced by serene bedrooms. Wake to light streaming through mature trees, entertain on the patio, or meander through the landscaped grounds. An enchanting hillside sweeps down from the house to a private tennis court, adding to the property’s sense of retreat. Whether envisioned as a tranquil sanctuary or a generational estate, this exceptional property offers boundless potential — all with Chilmark’s pristine beaches and up-island amenities at your fingertips.
Sold for $4,325,000
$4,325,000
18 Homeward Way, Chilmark, MA 02535
5beds
3,885sqft
Single Family Residence
Built in 1986
15 Acres Lot
$4,386,800 Zestimate®
$1,113/sqft
$6,386 Estimated rent
Home value
$4,386,800
Estimated sales range
Not available
$6,386/mo
Zestimate® history
Loading...
Owner options
List your home for rent
$6,386/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
Learn more$6,386/mo
Rent Zestimate®
Refinance and save
$25,471/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
See today's rates$25,471/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked: 7 hours ago
Listing updated: December 11, 2025 at 07:43pm
Listed by:
Bill Rossi,
Studio Realty
Bought with:
Jim Feiner
Feiner Real Estate
Source: LINK,MLS#: 43717
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bedrooms: 5
Heating
- Heat Pump
Appliances
- Included: Stove: Yes, Washer: Yes
Features
- AC, MiniSplit, Floor 1: Open dining/living room area, Den, three season room and five bedrooms, two and one half baths
- Flooring: Hardwood/tile/carpet
- Basement: Partial
- Fireplace features: 2 Wood Stoves
Interior area
- Total structure area: 3,885
- Total interior livable area: 3,885 sqft
Property
Parking
- Parking features: Gravel drive and parking
Features
- Exterior features: PubBch, Tennis, ScrPorch
- Has view: Yes
- View description: None, Pasture
- Frontage type: None
Lot
- Size: 15 Acres
- Features: Landscaped yard
Details
- Additional structures: Tennis Court, Viewing shed, utility shed.
- Parcel number: CHILM20P104
- Zoning: R3
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Irregular
Condition
- Year built: 1986
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cbl
Community & neighborhood
Location
- Region: Chilmark
Other
Other facts
- Listing agreement: E
Price history
| Date | Event | Price |
|---|---|---|
| 12/5/2025 | Sold | $4,325,000-7.9%$1,113/sqft |
Source: LINK #43717 Report a problem | ||
| 11/5/2025 | Pending sale | $4,695,000$1,208/sqft |
Source: LINK #43717 Report a problem | ||
| 9/21/2025 | Contingent | $4,695,000$1,208/sqft |
Source: LINK #43717 Report a problem | ||
| 9/13/2025 | Listed for sale | $4,695,000$1,208/sqft |
Source: LINK #43717 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,064 +13.6% | $2,694,900 +7% |
| 2024 | $5,339 +3.8% | $2,518,400 +28.8% |
| 2023 | $5,143 +5.6% | $1,955,700 +13.2% |
Find assessor info on the county website
Neighborhood: 02535
Nearby schools
GreatSchools rating
- 8/10Chilmark Elementary SchoolGrades: K-5Distance: 1.3 mi
- 7/10West Tisbury Elementary SchoolGrades: PK-8Distance: 5.1 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 8.5 mi
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$4,386,800
2% more
+$87,736
With Zillow Showcase(estimated)
$4,474,536
- Massachusetts
- Dukes County
- Chilmark
- 02535
- 18 Homeward Way