18 Homeward Way Chilmark, MA 02535
Chilmark NeighborhoodEstimated payment $25,299/month
Highlights
- 15 Acre Lot
- Wood Flooring
- Screened Porch
- Pasture Views
About This Home
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.
Listing Agent
Bill Rossi
Studio Realty Listed on: 09/13/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $6,064
Year Built
- Built in 1986
Lot Details
- 15 Acre Lot
- Property is zoned R3
Interior Spaces
- 3,885 Sq Ft Home
- Screened Porch
- Wood Flooring
- Pasture Views
- Partial Basement
- Stove
- Washer
Bedrooms and Bathrooms
- 5 Bedrooms
Utilities
- Heat Pump System
- Well
- Septic Tank
- Cable TV Available
Listing and Financial Details
- Tax Lot 104,97 and 99.2
- $2,451,800 per year additional tax assessments
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $6,064 | $2,694,900 | $1,130,100 | $1,564,800 |
| 2024 | $5,339 | $2,518,400 | $1,105,500 | $1,412,900 |
| 2023 | $5,143 | $1,955,700 | $850,300 | $1,105,400 |
| 2022 | $4,871 | $1,727,200 | $833,600 | $893,600 |
| 2021 | $4,657 | $1,600,200 | $833,600 | $766,600 |
| 2020 | $4,489 | $1,569,600 | $817,200 | $752,400 |
| 2019 | $4,367 | $1,516,300 | $817,200 | $699,100 |
| 2018 | $4,170 | $1,516,300 | $817,200 | $699,100 |
| 2017 | $4,029 | $1,503,300 | $817,200 | $686,100 |
| 2016 | $4,059 | $1,497,800 | $817,200 | $680,600 |
| 2015 | $3,939 | $1,497,800 | $817,200 | $680,600 |
| 2014 | $5,397 | $2,176,100 | $1,386,000 | $790,100 |
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 09/13/2025 09/13/25 | For Sale | $4,695,000 | -- | $1,208 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Land Court Massachusetts | -- | -- | |
| Land Court Massachusetts | -- | -- |
Source: LINK (Vineyard)
MLS Number: 43717
APN: CHIL-000020-000000-000104
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