18 Homeward Way

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, 18 Homeward Way offers boundless potential — all with Chilmark’s pristine beaches and up-island amenities at your fingertips.