Overlook Ext Homes with Trail(s) Association Amenities

Welcome to Overlook Extension, a hidden gem nestled in the picturesque Hilton Head Island, South Carolina. This charming subdivision in Beaufort County offers a unique blend of tranquil living and vibrant community spirit, making it the perfect place to call home. With its stunning natural surroundings and close proximity to the island's famed beaches, Overlook Extension is an ideal setting for families, retirees, and everyone in between.

One of the standout features of Overlook Extension is its commitment to outdoor living, exemplified by the Homes with Trail(s) Association. Residents have exclusive access to a network of scenic trails that wind through the lush landscape, perfect for leisurely strolls, invigorating jogs, or serene bike rides. The trails offer a wonderful opportunity to immerse yourself in nature while enjoying the fresh coastal air.

In addition to the trails, the community boasts a range of amenities designed to enhance your lifestyle. Imagine spending weekends at the community pool, hosting gatherings at the clubhouse, or enjoying friendly games at the sports courts. The sense of camaraderie among neighbors creates a welcoming and supportive atmosphere, where friendships flourish and memories are made.

Living in Overlook Extension means embracing a laid-back lifestyle with all the conveniences of Hilton Head Island at your fingertips. From world-class dining and shopping to pristine golf courses and water activities, this vibrant locale has something for everyone. Come discover the charm and beauty of Overlook Extension—your dream home awaits!

Newest Overlook Ext Homes with Trail(s) Association Amenities

$5,999,000

5 Beds ⋅ 5 Baths ⋅ HILTONHEAD-508634 MLS

Welcome to Refined Coastal Simplicity on the Port Royal Shoreline. Sited on a rare, private .77 acre lot, this custom-built home was designed for an effortless lifestyle where understated luxury is felt, not just seen. Inside discover culinary artistry with a home chef's kitchen anchored by a curated wood-top island and a massive butler's pantry- perfect for seamless entertaining. Dual Primary Ensuites (Main and 2nd Floor) provide flexible sanctuary for guests or multi-generational families. Step outside and transition from the screened porch with its cozy fireplace to the heated and chilled pool, ensuring the perfect temperature regardless of the season. From the boardwalk to the expansive rear veranda, every inch of this Port Royal property is designed to make coastal living entirely uncomplicated. This exceptional seaside home is a must see in private Port Royal Plantation. Click the vidoe link to view interior and drone exterior footage.

3 Wagener Place, Hilton Head Island

Listing courtesy of Charter One Realty.

$6,500,000

3 Beds ⋅ 5 Baths ⋅ HILTONHEAD-502804 MLS

Spectacular must-see modern and dramatic Wayne Windham designed oceanfront estate in residential Port Royal. This gorgeous home offers a flexible floor plan with a gourmet kitchen and great room, 3-4 bedroom suites, and endless extra living areas to accommodate an office, children's area, game tables, piano room, work-out room, you name it! Perfect for family living as well as entertaining! Located on a prime ocean view lot, this home has been lightly lived in. Professional landscaping, free-standing columns, dramatic sweeping twin staircases, saturnia inlayed flooring, Vitricore kitchen cabinets, fireplace, glass brick walls, infinity pool, are just some of the upscale appointments of this light-filled masterpiece.

20 N Port Royal Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

Start Your Search

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.