18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
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18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
18 Homeward Way
For Sale

18 Homeward Way

18 Homeward Way, Chilmark, MA 02535

$4,695,000
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.

5
beds

3
baths

3,885 Sq.Ft. LIVING AREA

15 Acres lot

Features & Amenities

Interior

  • total bedrooms5
  • Total bathrooms3
  • full bathrooms2
  • half bathroom1
  • Flooring Hardwood/tile/carpet
  • Fireplace 2 Wood Stoves
  • APPLIANCES Stove: Yes, Washer: Yes
  • other interior Features AC, Mini Split, Floor 1: Open dining/living room area, Den, three season room and five bedrooms, two and one half baths

Area & Lot

  • Status For Sale
  • Living Area3,885 Sq.Ft.
  • Total Area3,885 Sq.Ft.
  • Lot Area15 Acres
  • MLS® ID43717
  • TypeResidential
  • YEAR BUILT1986
  • View DescriptionNone, Pasture

Exterior

  • water SourceWell
  • utilitiesCbl
  • lot featuresLandscaped yard
  • parkingGravel drive and parking
  • HEAT TYPEHeat Pump
  • sewerSeptic Tank
  • SubstructureIrregular
  • other exterior FeaturesPub Bch, Tennis, Scr Porch

Financial

  • Sales Price$4,695,000
  • Zoning R3
 Bill Rossi

Bill Rossi

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From representing sellers through a comprehensive marketing plan to representing buyers with an educated view of the current market, Peyton & Bill strive to provide the highest quality service and go beyond the expected.

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