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 Tools

Property Details of 18 Homeward Way, North

Property Details

Interior Features

Community

Other Details

Map Location

Listed by Studio Realty

Listing Sold by Feiner Real Estate

Based on information submitted to LINKMV as of December 7, 2025 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from Hancock Real Estate. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

$

Do not fill in this field:

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.