Overlook Place Homes with Pickleball Association amenities

Overlook Place Homes with Pickleball Association amenities

Welcome to Overlook Place, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This picturesque subdivision in Beaufort County offers an idyllic coastal lifestyle, blending the charm of Southern living with modern conveniences. Overlook Place is not just a neighborhood; it’s a vibrant community where residents enjoy the best of what island life has to offer.

The homes in Overlook Place are thoughtfully designed, featuring spacious layouts and beautiful outdoor spaces that invite you to soak up the sun and enjoy the coastal breeze. With a variety of architectural styles, each residence reflects the unique character of the island, ensuring that you find a home that perfectly suits your taste.

One of the standout features of Overlook Place is its commitment to an active lifestyle, highlighted by the Pickleball Association amenities available to residents. Whether you’re a seasoned player or just looking to learn a new sport, the pickleball courts provide a fantastic opportunity for socializing and staying fit. This fast-paced game is perfect for all ages, fostering a sense of community as neighbors come together for friendly matches and events.

In addition to pickleball, Overlook Place is conveniently located near stunning beaches, world-class golf courses, and a plethora of dining and shopping options. The charm of Hilton Head Island is at your fingertips, making it easy to indulge in leisurely strolls along the shore or savor fresh seafood at local eateries.

Discover the enchanting lifestyle that awaits you at Overlook Place, where your dream home and vibrant community life come together seamlessly. Welcome home!

Newest Overlook Place Homes with Pickleball Association amenities

$7,800,000
6 Beds ⋅ 8 Baths ⋅ 6,208 SqFt. ⋅ HILTONHEAD-510819 MLS
Experience unparalleled oceanfront luxury in the exclusive, private community of Port Royal on Hilton Head Island. This 6,208-square-foot, two-story coastal home features six bedrooms, five full baths, and three half baths, offering an exceptional blend of timeless architecture. Meticulously enhanced with extensive modern updates, the home welcomes you with a grand foyer, soaring ceilings, and open, light-filled living spaces. Stunning 2-story glass frames sweeping panoramic Atlantic vistas and the maritime landscape from nearly every room. The newly remodeled chef's kitchen is complete with leather-stamped quartz countertops, a premium Sub-Zero refrigerator, a gas Bertazzoni Range, 2 stainless steel sinks, a farmer sink and a customized bar area. A generous island designed for effortless entertaining seats six. Throughout the interior, earth toned tile, stone and wood flooring complement the home's design. The primary suite serves as a serene sanctuary with stunning ocean views and a spa-inspired bathroom while each guest suite ensures ultimate comfort with private en-suites. Notably, three of the six bedrooms boast breathtaking direct ocean views.The luxury extends outdoors to a private beachfront oasis designed for relaxation and entertainment. Expansive patios, second-story veranda balcony, and an oceanside salt water pool offer front-row seats to legendary sunrises, cool sea breezes, and the tranquil lapping of the waves. Enjoy direct, private access to Hilton Head's pristine shoreline right from your backyard. Thoughtfully updated, the property features a durable metal roof, a classic stucco exterior, a spacious three-car garage, newly paved driveway plus paver pathways and refreshed landscaping. Situated on one of Port Royal's private, winding, oak-tree-lined cul-de-sac streets, this gated-community oceanfront residence offers a rare combination of luxury, privacy, and coastal living at its best.

10 Drayton Place, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$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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