Perched atop the highest point on the South Shore, Heart Rock Bluff is one of Chilmark’s most iconic rental compounds—offering panoramic ocean views from Chappaquiddick to Aquinnah and direct access to over 1/3 mile of private beach adjacent to Lucy Vincent. Set on 6 acres of manicured grounds, the estate includes three distinct structures, thoughtfully designed for luxurious summer living.
The Main House features 3 bedrooms, 4 bathrooms, 2 outdoor showers, a chef’s kitchen, cozy TV room, and a screened-in dining porch that opens fully for seamless indoor-outdoor entertaining. The expansive primary suite spans the entire second floor with two full bathrooms, private outdoor space, and dual walk-in closets. Outside, a wraparound mahogany deck hosts a cedar hot tub, Argentinian grill, and oversized dining table for al fresco gatherings.
The Pool House includes 2 bedrooms, 1.5 baths, a full kitchen, and floor-to-ceiling glass doors that open to a heated saltwater pool. Across the lawn, the Tennis Loft offers 2 additional bedrooms, 1.5 baths, and a fully equipped gym with a Pilates Reformer, Peloton, and views of the tennis & pickleball court (shared with one neighbor).
With designer interiors, curated furnishings, and best-in-class amenities, this estate is ideal for families, reunions, retreats, or intimate weddings.
Breakdown by Structure:
Main House (3BR | 4BA):
King primary suite with 2 full bathrooms
2 guest bedrooms with queen beds
2 additional full bathrooms
2 outdoor showers
Pool House (2BR | 1.5BA):
Queen bedroom with ensuite bath
Bedroom with two twin beds
Full bath, full kitchen, living room
1 outdoor shower
Tennis Loft (2BR | 1.5BA):
Queen bedroom with powder room
Upstairs queen bedroom with ensuite bath
Workout room & outdoor shower
Amenities:
Private beach access
Heated saltwater pool
Outdoor hot tub
Tennis & pickleball court
Sauna
Gym with weights, Peloton, and Pilates Reformer
Chef’s kitchen
Screened-in porch
Argentinian grill
Fire pit
Vegetable & cutting garden
John Robshaw bedding
Central heat & AC in all structures
Laundry in each house
High-end water filtration system
Sonos-integrated AV, 65” 4K TVs
Board games, books, and poker/cards
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.