Overlook Ext Homes with Two Story Architectural Style

Welcome to Overlook Extension, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This charming subdivision offers a unique blend of coastal living and suburban tranquility, making it an ideal choice for families, retirees, and everyone in between. With its lush landscapes, serene atmosphere, and proximity to beautiful beaches, Overlook Extension is the perfect place to call home.

The homes in this delightful community are characterized by their stunning two-story architectural style, which adds a touch of elegance and sophistication to the neighborhood. These spacious residences are designed with an open-concept layout, allowing for ample natural light and seamless flow between living spaces. Whether you're hosting a family gathering or enjoying a quiet evening, the two-story designs provide both comfort and functionality.

Residents of Overlook Extension enjoy easy access to a variety of amenities, including world-class golf courses, gourmet dining options, and boutique shopping experiences. The community is also just a short drive away from the pristine beaches that Hilton Head Island is famous for, where you can soak up the sun or engage in exciting water sports.

In addition to its prime location and beautiful homes, Overlook Extension fosters a strong sense of community. Neighbors often gather for social events, creating lasting friendships and a welcoming atmosphere. If you're looking to embrace the idyllic coastal lifestyle while enjoying the charm of a close-knit community, Overlook Extension is the perfect place to settle down. Discover your dream home in this enchanting subdivision today!

Newest Overlook Ext Homes with Two Story Architectural Style

$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.