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$2,000
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-501423 MLS
Experience the magic of Hilton Head Island. Prime deeded summer weeks 31. Swallowtail at Sea Pines, a beloved and cherished property, offers the dream vacation lifestyle luxurious, carefree. Nestled midway between Harbour Towns iconic lighthouse and the sun-soaked Beach Club, Swallowtail places you steps from world-class golf, pristine beaches, waterfront dining, and vibrant arts. Whether you crave serene mornings by the ocean, sunset sails, or championship fairways, everything you love is just moments away! Your Summer, Your Way Flexibility Included!

70 Swallowtail Road Unit 2901, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,590,000
4 Beds ⋅ 4 Baths ⋅ 2,235 SqFt. ⋅ HILTONHEAD-500985 MLS
Location, location! Overlooking the 2nd fairway of the world-famous Harbour Town Golf Links, this beautifully renovated 4-bedroom, 4-bath home offers the perfect Sea Pines lifestyle. Enjoy front-row views of the Heritage Classic Golf Tournament right from your backyard. Walk around the corner to Sea Pines Center to for dinner. Walk to the Harbor Town Pool in 5 minutes. The Beach Club is reached in no time by hopping on the Trolley at the stop right around the corner; or take a bike on the leisure trails. Recently renovated from top to bottom, the home feels brand new with fresh paint, all-new trim, doors, flooring, lighting and new furniture throughout. The Chef's Kitchen features a brand-new GE gas range with a downdraft and a new GE Refrigerator; a new HVAC system plus all-new duct work provides year-round comfort. Each bedroom has its own full bath, creating the perfect setup for family and guests. Only used as a 2nd home right now, rental projections are $98,800/year. Whether this will be your primary home, vacation retreat, or rental investment, it has a winning combo of modern updates, timeless comfort, and one of the most desirable locations in Hilton Head.

11 Muirfield Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$2,199,000
4 Beds ⋅ 4 Baths ⋅ 3,700 SqFt. ⋅ HILTONHEAD-500571 MLS
This sophisticated Marsh Island turn-key home offers a perfect floor plan and a gorgeous stunning marsh-wrapped view of the free-form pool with a large Stone Works designed surround. The numerous first-class updates in this home, its meticulous care, and only part-time occupancy by the owners add to its endless appeal. Enter into an atrium that opens to the great room and dining area with soaring ceiling, and the kitchen and breakfast area. This magazine-worthy kitchen offers extensive Poggen Pohl cabinets, SubZero refrigerator, Wolf Microwave and cook top, double ovens, Madagascar marble counters, and a laundry/pantry room with wine racks and a wine refrigerator. Also located on the first floor are a separate office and the primary suite. Over the garage is a large bonus room. Off the foyer soars a modern staircase and balcony with stainless handrails and balusters leading to the 3 guest rooms. There is a 220 volt EV charger in the garage. Enjoy the exclusive and coveted Marsh Island residential neighborhood, with close access to Sea Pines Country Club and all that Sea Pines offers.

2 Long Marsh Lane, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$1,299,000
3 Beds ⋅ 2 Baths ⋅ 1,400 SqFt. ⋅ HILTONHEAD-500129 MLS
This highly sought-after Cutter Court Penthouse in the heart of Sea Pines, with its jaw-dropping direct views of the iconic Harbour Town Lighthouse, world-famous Harbour Town Marina, and the shimmering Calibogue Sound, is fully furnished and move-in ready. These penthouses rarely hit the market and sell quickly. This 3BR/2BA retreat has been completely updated and offers the perfect blend of style, comfort, and convenience, along with a strong short-term rental history. The spacious open layout includes a modern kitchen with granite countertops, stainless steel appliances, a dinette, and a bright living area. Relax and take in unforgettable sunsets from the main balcony, showcasing postcard-perfect views of the Lighthouse, Yacht Basin, and Calibogue Sound. The king master suite boasts its own private balcony, while two additional queen bedrooms offer comfort for family or guests. The two bathrooms each feature a walk-in shower, and the many windows throughout the Penthouse provide awesome views and abundant natural light. Its prime location puts you just steps from the Harbour Town Golf Links & Clubhouse, the Sea Pines Racquet Club, waterfront dining at the Quarterdeck and other popular restaurants, as well as charming shops, boutiques, art galleries, and the iconic Lighthouse itself. Enjoy world-class golfing in Sea Pines at the the three championship courses: Harbour Town Golf Links, Heron Point by Pete Dye and Atlantic Dunes by Davis Love III. Additional amenities include tennis and pickleball, Lawton Stables, Sea Pines Forest Preserve, Sea Pines Beach Club with private beach access, South Beach Marina, miles of bike trails, Sea Pines Center, and the free seasonal trolley service. Harbour Town is the vibrant heart of Hilton Head Island, alive with festivals, live music, shops, dining, and endless water activities all year long. Whether you're seeking a high-income short-term rental, a luxurious second home, or a permanent retreat, this Penthouse delivers it all - a prime location, top-floor privacy, as well as designer finishes and low-maintenance living in one of the Islands most prestigious addresses. Don't miss this chance to own a true Harbour Town gem where every day feels like a vacation.

6 Lighthouse Lane Unit 953, Hilton Head Island

Listing courtesy of Premier Properties of Hilton Head Island.

$6,999,000
5 Beds ⋅ 6 Baths ⋅ 3,669 SqFt. ⋅ HILTONHEAD-500303 MLS
Welcome to your coastal sanctuary in Sea Pines Resort-an exquisite 2ND ROW new-construction home designed for luxury living and / or exceptional rental potential. This 5-bedroom, 5.5-bath masterpiece offers approximately 3,669 heated square feet of finely crafted space, perfectly positioned on a 2nd-row homesite with STRONG OCEAN VIEWS and effortless access to the wide white sand beaches of Hilton Head Island.From the moment you enter, a private elevator and light-filled foyer set the tone for a home that blends coastal elegance with modern comfort. The open-concept main level showcases a chef's kitchen with premium appliances, custom cabinetry, and a large island that flows seamlessly into the dining and living areas-ideal for entertaining large groups or enjoying intimate family gatherings. Expansive windows and glass doors draw your eye outward to the ocean and to the resort-style outdoor living spaces.Step outside to your private oasis: an infinity-edge pool and spa that appear to melt into the horizon, framed by a spacious covered lanai and multiple porches. Enjoy al fresco dining, lounging, or watching the sunset by the outdoor fireplace-this home was designed to embrace indoor-outdoor living at its finest. Just steps away, a convenient beach path delivers you onto one of Hilton Head's most beautiful stretches of sand.Each of the six bedrooms is thoughtfully appointed with its own en-suite bath, offering comfort and privacy for owners and guests alike. Multiple primary suites, generous bunk or guest rooms, and carefully planned bath layouts make this home ideal for multi-generational living or high-occupancy vacation rentals. The half bath is perfectly positioned for pool and common-area use.Every detail was considered for both luxury and durability: high-end finishes, impact-rated windows and doors, designer lighting, and a floor plan optimized for today's coastal lifestyle. Ample storage, a ground-level drop zone for beach gear, and flexible gathering spaces ensure that the home is as functional as it is beautiful.

18 Oyster Catcher Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$6,100,000
5 Beds ⋅ 5 Baths ⋅ 4,449 SqFt. ⋅ HILTONHEAD-500143 MLS
Welcome to 30 E Beach Lagoon, a stunningly remodeled Oceanfront home located on one of Sea Pines most prestigious streets. Rarely does a property blend luxury, charm, and location this seamlessly. Designed with timeless coastal elegance, this home offers an exceptional lifestyle, 5 bedrooms, 5 baths, and just steps from your private deeded beach access. Inside, soaring vaulted ceilings with exposed beams, a masonry brick fireplace, and wide-plank wood floors create a warm, inviting atmosphere. The kitchen features high-end natural wood cabinetry, sleek countertops, and stainless steel appliances ideal for entertaining or quiet mornings at home. The main house flows beautifully into a spacious living area filled with natural light, while the private, attached guest house offers flexibility for hosting friends or extended family. The primary suite features a private deck with peekaboo ocean views and easy access via the in-home elevator. Outside, enjoy your own private pool surrounded by lush, mature landscaping, creating a serene retreat that feels both secluded and coastal. The home also includes a two-car garage and has never been used as a rental, offering pristine condition and pride of ownership. Whether you're searching for a luxury second home or a high-performing short-term rental, 30 E Beach Lagoon delivers on all fronts location, design, and lifestyle all within the gates of Sea Pines Resort.

30 E Beach Lagoon Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$3,390,000
4 Beds ⋅ 5 Baths ⋅ 3,100 SqFt. ⋅ HILTONHEAD-452729 MLS
SECOND ROW OCEANFRONT HOME IN THE SOUTH BEACH AREA OF SEA PINES PLANTATION is available to make your dreams come true!!! LOCATION! LOCATION! LOCATION! Living life in the Low Country only MINUTES away from our nationally recognized beach is now a REALITY! This custom built 2nd ROW OCEAN beauty has very close proximity to the beach & to the South Beach Marina area where your ultimate island experiences await. There are soooooo many direct views of the ocean from the multiple levels and balconies! All newly renovated coastal bathrooms give this home a current vibe! Fun local activities include biking, boating, dining, shopping, kayaking, dolphin watching, tennis, pickle ball & MORE! The cathedral ceilings in the living area, travertine floors & open concept living w/outside wrap-around balconies towards the ocean complement the Low Country lifestyle! The kitchen has a Viking stove, newer refrigerator, floating shelves, Italian imported marble countertops & a huge pantry! The entire lowest floor has as much space as you can imagine to store all your beach/pool/bikes and MORE!! During high season you can take the trolley anywhere in Sea Pines so you can park your car and never have to drive while you are visiting. The gorgeous pool has a spa with a water fountain and the pool also has had a heater added to it so you can swim in the pool year round! If you are looking for the perfect house in the PERFECT easy location....you have just found it!

4 Gadwall Road, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$4,250,000
6 Beds ⋅ 6 Baths ⋅ 6,000 SqFt. ⋅ HILTONHEAD-450230 MLS
Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

25 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

$4,600,000
4 Beds ⋅ 6 Baths ⋅ 6,042 SqFt. ⋅ HILTONHEAD-447864 MLS
This one-of-a-kind property is privately sited on almost an acre lot with panoramic marsh and water views providing the perfect backdrop for spectacular sunsets. Kermit Huggins, renowned architect, designed this property with 2 structures that harmoniously co-exist with their natural surroundings. Special features include new metal roof, hardwood flooring, pella windows/doors, renovated kitchen,& interior paint. The main house boasts an upper level luxurious owner suite & guest house has 2 en-suite bedrooms plus kitchenette. Incredible outdoor living with heated/chilled saltwater pool, expansive deck, and private dock. Waterfront Perfection!

29 Baynard Park Road, Hilton Head Island

Listing courtesy of Charter One Realty.

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