Overlook Ext Homes with Private Pool

Welcome to Overlook Extension, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This charming subdivision offers a blend of coastal elegance and serene living, making it an ideal haven for families, retirees, and anyone seeking a tranquil lifestyle by the sea.

Overlook Extension is renowned for its beautifully designed homes, many of which feature private pools—perfect for those hot summer days or evening gatherings with friends and family. Imagine stepping out into your own backyard oasis, where you can relax by the pool, soak up the sun, or host unforgettable barbecues under the stars. Each home is thoughtfully crafted with modern amenities and tasteful finishes, ensuring that comfort and style go hand in hand.

The community is strategically located to provide easy access to Hilton Head Island's stunning beaches, world-class golf courses, and vibrant dining and shopping venues. Residents enjoy the best of both worlds—an inviting neighborhood atmosphere and the excitement of island living. Whether you’re looking for adventure on the water or a peaceful retreat, Overlook Extension is the perfect place to call home.

With a strong sense of community and an abundance of recreational opportunities, Overlook Extension invites you to experience the laid-back lifestyle that Hilton Head Island is famous for. Come discover your dream home with a private pool in this idyllic subdivision, where every day feels like a vacation. Your slice of paradise awaits!

Newest Overlook Ext Homes with Private Pool

$5,499,800

5 Beds ⋅ 5 Baths ⋅ 4,563 SqFt. ⋅ HILTONHEAD-508634 MLS

Designed for those who love to entertain with purpose and elegance, this custom-built seaside home on a rare 0.77-acre lot offers an unmatched relaxed lifestyle both inside and out. Purposely designed by philanthropic owners, the home's open layout including dual sided fireplace effortlessly accommodates private gatherings and charitable galas for 50+ seated guests-flowing smoothly from indoor living spaces to the expansive, light-filled rear veranda. At the heart of the home, a chef's kitchen features a custom wenge wood-top island flanked by durable finished upper tier cabinetry and a massive butler's pantry built to handle full-service catering or intimate family dinners with equal ease. The outdoor sanctuary continues the theme of year-round hospitality, featuring a screened porch with a cozy fireplace, a custom boardwalk, and a climate-controlled heated and chilled pool for seasonal comfort. Two primary ensuites-conveniently situated on both the main and second levels-provide ultimate privacy and flexibility for hosting overnight guests or multi-generational family living. From grand philanthropic events beneath the veranda to quiet mornings on the shoreline, this home embodies the very best of Port Royal coastal living. Click the video 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 ⋅ 5,725 SqFt. ⋅ 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.

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