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$1,299,000
3 Beds ⋅ 2 Baths ⋅ 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.

$1,249,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-500380 MLS
Completed in 2024, this custom Allison Ramsey-designed home sits on a 1.14-acre marshfront lot, created by consolidating part of a neighboring parcel to enhance privacy, space, and views. Designed to embrace its surroundings, the elevated home offers sweeping marsh views and a blend of Lowcountry charm and casual luxury. Built by CMS with top-tier finishes, it features approx. 2,500 sq ft, French oak floors, Andersen windows and doors, 10-foot ceilings, and a new elevator. A rare opportunity for buyers seeking a brand-new home without the time and hassle of building. The kitchen features Thermador and Bosch appliances, custom cabinetry, and a large island. Outdoor living includes a wraparound porch, tabby fireplace, gas lanterns, irrigation, and a tankless water heater.

108 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$6,100,000
5 Beds ⋅ 5 Baths ⋅ 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.

$1,799,999
4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-452326 MLS
Stunning Custom-Built 4-Bedroom Home in Prime Folly Field, Hilton Head - Steps from the Beach. Discover your dream coastal retreat in the highly desirable Folly Field neighborhood of Hilton Head Island. This exceptional custom-built 4-bedroom (plus unique loft), 3-bath home offers 2,523 square feet of timeless elegance and modern luxury on a generous lot. Just a short 7-10 minute stroll to Folly Field Beach Park, this property delivers the perfect blend of beach access, privacy, and investment potential. Step inside to an inviting open-concept floor plan flooded with natural light. Soaring vaulted ceilings and a dramatic wall of windows frame the gorgeous great room, creating an airy, spacious feel ideal for relaxing and entertaining. The chef's dream gourmet kitchen features elegant marble countertops, high-end stainless steel appliances (including a premium Bertazzoni range, Bosch, and Blomberg), and beautiful custom stone and tile work. Charming barn doors, a step-down living area, and an expansive balcony add character and functionality. Bonus First-Floor Apartment: This home includes a completely separate 1-bedroom, 1-bath apartment with its own full kitchen and private lanai - offering two distinct living/rental units for the price of one. Whether you're looking for a primary residence, second home, or turnkey investment, the strong short-term rental demand in Folly Field makes this a high-performing opportunity.

9 Mimosa St, Hilton Head Island

Listing courtesy of Charter One Realty.

$499,700
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-454081 MLS
This 3,152 sq ft 4BR/3.5BA cottage in Haig Point is one of the community's rare homes with only a POA--offering the convenience of 24/7 mainland access. Designed for flexibility, the home features two principal suites, one on the main level and another upstairs, perfect for multi-generational living or hosting guests.The spacious open concept living and dining area flows easily into the kitchen, while outdoor living is maximized with a wide front porch, a screened back porch, and an upstairs porch off the principal suite. Inside, you'll also find a large laundry room, abundant storage, and an elegant staircase that anchors the homes character.Nestled within The Cottages at Haig Point, privacy abounds in this serene setting. With renovations and finishing touches, this home offers a unique opportunity to create your ideal island retreat. Once membership is added, enjoy world-class amenities including championship golf, tennis, pickleball, pools, and two restaurants.Offered AS IS, WHERE IS, this cottage combines space, convenience, and potential in one of Daufuskie Islands most sought-after communities. Come explore the Lowcountry lifestyle today!Enjoy island living without the crowds in this rare coastal retreat on a bridgeless island, where every day feels like a private getaway. Haig Point offers a park-like setting of open spaces, centuries-old oaks, and sweeping water views, with amenities including a Rees Jones Signature 20-hole golf course plus a 9-hole course, racquet sports, fitness center, pools, and dining. Stroll for miles along uncrowded beaches or enjoy seamless mainland access with a private ferry and 24/7 water taxi to Harbour Town. With 24/7 security, daily UPS and FedEx delivery, Instacart to your door, and even dry-cleaning pickup, this unique community blends privacy, luxury, and convenience.

22 Carnoustie Ct, Daufuskie Island

Listing courtesy of Charter One Realty.

$4,300,000
6 Beds ⋅ 7 Baths ⋅ HILTONHEAD-453824 MLS
Your Dream Awaits with a 4-minute walk to the beach, inside this stunning, renovated, luxury masterpiece nestled in an exclusive beachside gated community. This Goliath-sized, breathtaking home is a place to live, a lifestyle, and a lucrative STR investment. Enjoy a very short walk to the beach, one of your many private terraces overlooking your private heated pool or the golf course, and evenings spent entertaining in exquisite designer spaces. Modern amenities, Expansive floor plan, peaceful, private & gated, & a proven rental revenue stream. Your chance has arrived to own a slice of heaven that could pay for itself. Community/home video available.

12 Port Tack, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$3,390,000
4 Beds ⋅ 5 Baths ⋅ 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.

$6,000,000
5 Beds ⋅ 7 Baths ⋅ HILTONHEAD-452750 MLS
Stately, Sound front home with Ocean views. 199 ft of Waterfront. Water views from every room to include Ocean, Sound, Lagoon and #6 Oyster Reef Golf green. The home boasts man-made and natural elements that make it Dazzle. Designed for Cooking and Entertaining with large open concept spaces surrounded by glass. Well designed Chefs Kitchen to include Sub zero refrigerators, Wolf cooktop and Miele appliances. Formal living spaces include Cypress ceilings, Rosewood inlays, White Oak flooring, Teak inlays and 2-story Stone and Copper clad Fireplace. Expansive Resort style Pool with Spa, Wading area, new decking and Pool House. 4 Car Garage with quiet lift door mechanisms. Glass door Elevator, Wine Room, Den, Game & Theater rooms.

16 Oyster Shell Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$3,499,000
9 Beds ⋅ 11 Baths ⋅ HILTONHEAD-448624 MLS
Brand New Home Just Completed! 5,300 heated sq. ft. 9 BR's 10 1/2 baths. Private Infinity Edge Pool. Amazing ocean and marsh views from this ideal location. Finest finishes, details, trim, fixtures, appliances. Parking garage for 6+ cars, plus 4 on the driveway. Elevator. Penthouse gathering room with beamed ceilings, kitchen open to huge dining area and great room. Best views in the home are on this level, with a large covered porch to admire the sunshine, breathe in the salt air, gaze over the marsh and ocean, listen to the shore birds calling and celebrating another gift of a day! Brand new homes all around, resort style atmosphere. Just a short distance to the beach. Additionally, the open space to the side and rear of this home create a uniquely open feeling! New on the rental market, already a favorite, expected to generate significant income.

13 Bradley Circle, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$4,750,000
6 Beds ⋅ 8 Baths ⋅ HILTONHEAD-451281 MLS
The ultimate home, perfect for entertaining! Spacious 2nd-row, 6 BR | 6 BA | 2 HB home on Armada in Palmetto Dunes just steps from 3 miles of award-winning beach. Freshly painted with coastal-chic décor, this home has a spectacular 1st floor featuring a chef's eat-in kitchen, dining room, living room, wet bar off the leisure room, powder room & sunroom. Offers a 3-stop elevator & three primary suites on the 2nd-floor. Outdoor entertainment area offers an idyllic wooded view, a covered lounging & dining area with a wet bar and grill, & a large pool with a spa. Ample parking with a large driveway & garage. Guests and owners have access to all the amenities in Palmetto Dunes: golf, tennis, pickleball, an 11-mile lagoon, golf at the Arthur Hills Golf Course in Leamington, and much more. Short walk or bike ride to the heart of Palmetto Dunes. Seasonal Dunes Buggy is available throughout Palmetto Dunes and the Shelter Cove area. Short walk or bike ride to resort amenities!

9 Armada Street, Hilton Head Island

Listing courtesy of Schembra Real Estate Group.

$4,250,000
6 Beds ⋅ 6 Baths ⋅ 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.

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