Overlook Ext Homes with Pool Association Amenities

Welcome to Overlook Extension, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This charming subdivision is a perfect blend of coastal serenity and vibrant community life, making it an ideal destination for families, retirees, and anyone looking to embrace the laid-back island lifestyle.

Overlook Extension boasts a variety of beautifully designed homes, each exuding character and warmth. Many of these residences feature private pools, offering a refreshing retreat right in your backyard. Imagine basking in the South Carolina sun, enjoying leisurely afternoons by the pool, or hosting unforgettable summer barbecues with friends and family.

As a resident of Overlook Extension, you’ll also enjoy exclusive access to a range of community amenities that enhance your living experience. The Homes with Pool Association provides a welcoming environment where neighbors become friends. Take advantage of the well-maintained common areas, perfect for leisurely strolls or picnics with loved ones. The community pool is a fantastic spot to unwind, socialize, and create lasting memories with fellow residents.

Located just a stone's throw from Hilton Head Island's stunning beaches, world-class golf courses, and a variety of dining and shopping options, Overlook Extension offers the perfect balance between tranquility and convenience. Whether you’re looking for a vacation home or a permanent residence, this community is sure to capture your heart.

Discover the charm of Overlook Extension and experience the best of island living today! Your dream home awaits in this picturesque paradise.

Newest Overlook Ext Homes with Pool Association Amenities

52 N Port Royal Drive, Hilton Head Island

$7,800,000

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-513205 MLS

Set dirеctly on thе οcеаn іn the рrіvate community of Ρort Rοyal on Hilton Head Island, this custom beachfront home has undergone an exceptional interior transformation, resulting in a 'Like New' premium state of the art beach home as special as its oceanfront backdrop. The entire main living area was reconfigured and upgraded offering natural light, enhanced ocean views and overall, a superior easy living floorplan. The kitchen, living and dining spaces now flow together seamlessly and are anchored by an oversized granite island, custom cabinetry and statement lighting. Walls of windows fill the home with natural light and frame the ocean beyond, while extensive custom millwork, built-ins and beautiful wood floors give the home a level of character you simply don't find everywhere. Two gas fireplaces, separate living and family rooms, a private office, home gym and elevator add to the way this home actually lives. There are two ocean-view primary suites, including one on the main level. Upstairs, the completely redesigned primary suite feels like its own private retreat. The bedroom opens to a private oceanfront balcony, while the bath features two separate water closets, dual vanities, two custom walk-in closets, a large soaking tub and oversized tiled shower. Outside is where the setting really takes over. A screened porch overlooks the private pool, fenced yard, serene landscaping and ocean beyond. Custom outdoor lighting carries the home into the evening, while mature trees and thoughtfully designed landscaping create privacy without taking away from the view. Offering over 5000 heated square feet of private oceanfront living with 2 living rooms, 4 large bedrooms, a huge oceanfront office, oceanfront gym & elevator. This isn't simply a home near the beach. This is private oceanfront living at its very finest.

52 N Port Royal Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$5,499,800

5 Beds ⋅ 5 Baths ⋅ 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.

20 N Port Royal Drive, Hilton Head Island

$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.

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