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
$4,416,200 Zestimate®
$1,113/sqft
$7,821 Estimated rent
Home value
$4,416,200
Estimated sales range
Not available
$7,821/mo
Zestimate® history
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$24,997/mo
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List your homeWhat's special
Classic vineyard charmPrivate tennis courtEntertain on the patioScenic north roadSingle-level layoutMature treesSerene bedrooms
Zillow last checked:
Listing updated:
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 & HOA
Location
- Region: Chilmark
Financial & listing details
- Price per square foot: $1,113/sqft
- Tax assessed value: $3,924,000
- Annual tax amount: $6,064
- Date on market: 9/13/2025
- 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% |
| 2022 | $4,871 +4.6% | $1,727,200 +7.9% |
| 2021 | $4,657 +3.7% | $1,600,200 +1.9% |
| 2020 | $4,489 +2.8% | $1,569,600 +3.5% |
| 2019 | $4,367 +4.7% | $1,516,300 |
| 2018 | $4,170 +3.5% | $1,516,300 +0.9% |
| 2017 | $4,029 -0.7% | $1,503,300 +0.4% |
| 2016 | $4,059 | $1,497,800 |
Find assessor info on the county website
Neighborhood: 02535
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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
- Massachusetts
- Dukes County
- Chilmark
- 02535
- 18 Homeward Way
Nearby cities
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