Overlook Place Homes with Two Story Style

Overlook Place Homes with Two Story Style

Welcome to Overlook Place, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This charming subdivision offers residents a perfect blend of tranquility and coastal living, making it an ideal destination for families, retirees, and anyone seeking a serene escape. With its picturesque surroundings and proximity to the island’s pristine beaches, Overlook Place is a community that truly embodies the essence of island life.

One of the standout features of Overlook Place is its stunning two-story homes, designed to provide both elegance and functionality. These spacious residences typically boast open floor plans that seamlessly connect living, dining, and kitchen areas, perfect for entertaining friends and family. With multiple bedrooms and bathrooms, there’s ample space for everyone to enjoy their own sanctuary. Large windows flood the interiors with natural light, while outdoor spaces, including private patios and balconies, allow residents to soak in the beautiful South Carolina sunshine.

Living in Overlook Place means you’re just a stone's throw away from Hilton Head Island’s renowned amenities. Enjoy world-class golf courses, fine dining, and boutique shopping, all within a short drive. For outdoor enthusiasts, the island offers abundant opportunities for biking, hiking, and water sports, ensuring that every day can be an adventure.

Whether you’re looking to settle down or find a vacation retreat, Overlook Place is the perfect place to call home. Embrace the island lifestyle and discover the beauty of Hilton Head Island in this charming community!

Newest Overlook Place Homes with Two Story Style

$3,950,000
3 Beds ⋅ 3 Baths ⋅ 2,733 SqFt. ⋅ HILTONHEAD-511980 MLS
Reimagine oceanfront living on one of Hilton Head Island's most exceptional beachfront properties. Set beneath magnificent live oaks and surrounded by mature natural landscaping, this private retreat offers sweeping ocean views, ample room for expansion, and the rare opportunity to renovate, enhance, or create a new coastal estate tailored to your vision. Ideally positioned in the most coveted section of Port Royal Plantation, the property enjoys a peaceful setting away from the island's resort corridor while remaining minutes from renowned dining, golf, shopping, and amenities. The expansive rear deck is perfectly suited for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. The existing residence offers 3 bedrooms and 2.5 baths, with the half bath easily converted back to its original full-bath configuration. Wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass create warm, inviting interiors that connect seamlessly with the surrounding landscape. Adding to the property's distinction is its remarkable architectural history. Designed by internationally acclaimed architect Dean Winesett, whose work has appeared in *Architectural Digest* and *Southern Living*, the home was also featured in *Southern Living* and reflects his signature Lowcountry style and craftsmanship. Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that define this exclusive oceanfront community. Private amenities reserved for property owners and their guests include an oceanfront Beach House and swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and an array of recreational and social offerings. An irreplaceable beachfront setting, celebrated architectural legacy, exceptional private amenities, and endless possibilities combine to create one of the most compelling oceanfront opportunities currently available on Hilton Head Island.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

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