85 Gloucester Road

Tucked beneath moss-draped oaks and framed by serene lagoon waters and whispering palms, 85 Gloucester Road is not just a vacation home - it’s a storybook retreat where relaxation, nature, and Southern elegance intertwine. Located within the prestigious Shipyard Plantation, this custom-built gem combines Lowcountry charm with refined luxury welcoming up to 12 guests. Think of a peaceful world of slow mornings, sunlit afternoons, and golden evenings all surrounded by the natural beauty of Hilton Head Island!

Step inside, and a sense of calm washes over you. Sunlight filters through expansive windows, gliding across rich wood beams and airy vaulted ceilings. The heart of the home - a stunning chef’s kitchen - is a dream for culinary creatives, boasting high-end appliances, a six-burner gas range, and a stylish island perfect for sipping wine while dinner simmers. Flowing effortlessly into the cozy yet sophisticated living room, this open-concept space invites togetherness, whether you're curled up by the fireplace or gathered around the Smart TV for a movie night. Open the French doors and let your world expand onto a wrap-around screened porch - a sanctuary of its own, with plush seating, a flickering outdoor fireplace, and gentle lagoon breezes that make every meal feel like a special occasion.

As the stars rise, retreat to your private quarters. Each of the four en-suite bedrooms is thoughtfully curated for deep rest and comfort, featuring plush mattresses, premium linens, and spa-like bathrooms. The main-floor primary suite feels like a personal spa, complete with a freestanding soaking tub, dual vanities, and an oversized walk-in shower. Upstairs, a playful King and bunk room adds a fun twist for families, while the Queen suite with a sleeper sofa offers the perfect mix of comfort and flexibility. Every guest has their own peaceful corner - designed not just to sleep, but to truly unwind.

Outside, your private resort-style backyard awaits. The pool* glistens under the sun, complete with a tanning ledge perfect for lounging, while astroturf lawns keep everything green and barefoot-friendly. Sip lemonade poolside, refresh in the outdoor half bath, or light up the grill for an evening barbecue under string lights. And when you’re ready for adventure, Shipyard’s trails beckon - leading you past fairways and forests to the soft sands of the beach just two miles away.

From sunrise coffee on the porch to sunset strolls under the oaks, 85 Gloucester Road is where memories linger long after your suitcase is packed. Here, every detail whispers luxury - from high-speed Wi-Fi and Smart TVs to curated beach gear and a welcome basket filled with treats to start your stay with a smile. It’s the kind of place where time slows down, laughter comes easy, and the only question is why you didn’t come sooner. Enjoy a vacation reimagined with host2coast, your trusted Hilton Head Island Property Management partner.


PROPERTY SPECIFIC DETAILS:

* Shipyard is a gated community in which every vehicle must have a gate pass for entry. One gate pass is included with your reservation at the time of booking. If you require additional passes, please request the exact number needed to ensure they are prepared in advance. Each pass has a fee of $45. All gate passes must be picked up at the host2coast office prior to entry.
* Pool does not heat.
* Fireplace is not available for guest use.

STR Permit # 76390