Milestone

Beachfront hosted by Monique Truss

About this listing

Milestone is a newly relaunched oceanfront retreat set directly on the white sands of Grace Bay Beach, offering a rare blend of playful character, polished comfort and exceptional service. Designed as a relaxed yet stylish family home with a whimsical Los Angeles beach house feel, the property sits within the private and exclusive Leeward community, just two miles from the centre of Grace Bay and its celebrated restaurants, boutiques and resorts. From the moment you arrive, the views are striking, with uninterrupted sea vistas and a sense of openness that defines life at the water’s edge.

The house unfolds generously across the main residence and a separate guest cottage, allowing families and groups to come together while still enjoying space and privacy. Six bedrooms are set within the main house across both ground and upper levels, complemented by two further bedrooms in the guest cottage, including a children’s room designed for easy family living. Interiors feel light, contemporary and welcoming, with thoughtful details throughout, from ocean facing family television spaces upstairs to a dedicated office with desktop computers for those who need to stay lightly connected.

Life at Milestone is designed to flow seamlessly between indoors and out. Two newly appointed kitchens in the main house, including a chef’s kitchen with premium appliances, invite long lunches and relaxed evenings, centred around a striking thirteen foot dining table that naturally becomes the heart of the home. Outside, a newly built fifty foot heated pool with Baja decks and an integrated spa takes centre stage, framed by landscaped gardens and the beach beyond. Pavilions for outdoor dining, lounging and entertaining create shaded spaces throughout the day, with an outdoor bar, grill area and television making evenings under the stars especially inviting.

Wellbeing and play are woven into the experience. A full gym with Peloton bike and treadmill sits alongside a private massage room with its own bathroom, while a regulation size lighted pickleball court adds a lively social element to afternoons. Kayaks, paddleboards, snorkelling equipment and bicycles encourage easy exploration of both sea and shore, while a fire pit with seating on the beach provides a memorable setting as the sun dips below the horizon and the shoreline glows with soft lighting.

Service is discreet yet comprehensive, with a private chef, villa host, housekeeper and daily lifestyle concierge ensuring every detail is handled with care. High speed WiFi, an integrated indoor and outdoor sound system, gated security, mosquito misting and thoughtful lighting throughout the grounds create a sense of ease and reassurance without detracting from the relaxed atmosphere.

Milestone captures the essence of barefoot luxury on Grace Bay, where days are shaped by sunshine, sea breezes and effortless living, and evenings settle into a rhythm of shared meals, soft music and ocean air. It is a place to slow down, reconnect and enjoy the Caribbean at its most comfortable, sociable and beautifully unforced.