Chilmark Retreat on 8 Acres with Panoramic Ocean Views

Escape to the ultimate private getaway at this stunning 5-bedroom, 4.5-bathroom home on Peaked Hill, the highest point on Martha’s Vineyard. Nestled on 8 pristine acres and surrounded by Land Bank Reservation walking trails, this Chilmark retreat offers unparalleled views of the Atlantic Ocean and the island’s south shore.

The main house, spanning just under 4,500 sq. ft., is designed for relaxation and family gatherings. Enjoy breathtaking ocean vistas from the living room, dining area, and chef’s kitchen. Three of the bedrooms are ensuite, including a second-floor primary suite with a fireplace and south-facing views. A detached structure adds flexibility with 4 twin beds, a half bathroom, and a ping-pong table.

Outside, savor a hot tub accessed via a path through ancient glacial boulders, swings and hammocks throughout the property, and lush blooming gardens. Explore the private walking trail within the 8-acre grounds, which connects to Land Bank Reservation trails, or pick fresh produce and flowers from the vegetable and cutting garden. The property also features a second-floor deck with south shore views, an outdoor shower, a basketball hoop, and all beach and game amenities.

Bedrooms & Bathrooms
First Level: Primary suite with king bed and ensuite bath; half bath
Second Level: Second primary suite with queen bed, fireplace and ensuite bath; guest bedroom with queen bed and ensuite bath; guest bedroom with two twin beds; guest bedroom with one full bed and twin bunk beds
Detached Structure: Four twin beds for overflow guests, ping pong table, half bath

Note: We always recommend making every effort to personally view a property before booking. We represent the condition, size, and location of each home as accurately as possible, although all information is deemed reliable but not guaranteed. As rental agents, we represent the landlord. Please also be aware that any home built prior to 1978 may contain lead paint. Various types of mold occur naturally on Martha’s Vineyard, and some individuals may be sensitive or have allergic reactions to them.