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2 Willow Oak W Road, Hilton Head Island
$2,750,010
4 Beds ⋅ 5 Baths ⋅ 3,216 SqFt. ⋅ HILTONHEAD-504056 MLS
Welcome to 2 Willow Oak Road West, an extraordinary and masterfully renovated residence located in the heart of Sea Pines on Hilton Head Island. Thoughtfully redesigned with impeccable attention to detail, this stunning home now offers 4 bedrooms, 4.5 bathrooms, and a seamless blend of modern luxury and Lowcountry sophistication. Every inch of the home has been transformed, featuring top-of-the-line appliances, including a Fulgor Milano Fridge/Freezer ($25,000 value), Perlick Wine Fridge, a brand new Jen Air Gas range/stove with downdraft, new stainless steel microwave, and two Dishwashers for ultimate convenience, PLUS 2-brand new hot water heaters, and brand new roof. An additional bedroom and bathroom were added to enhance both functionality and comfort, creating ideal accommodations for family and guests alike. The open-concept living spaces flow effortlessly to the outdoors, where a brand-new wraparound and extended Trex deck provides the perfect setting for entertaining or relaxing while enjoying breathtaking views of the 16th hole of the Heron Point Golf Course. Situated on a private 1.09 acre lot, the property offers a rare level of privacy and space. The resort-style backyard features a brand new in-ground pool and hot tub, completing this exceptional outdoor oasis. Located within the world-renowned Sea Pines Resort, residents enjoy access to 3 championship golf courses with flexible access, pristine beaches, marina, dining, and endless amenities. Ideally situated in the heart of the community, you're just minutes from Harbour Town, the Sea Pines Beach Club, Lawton Stables, the Forest Preserve, and the miles of scenic bike trails that connect it all. This is a truly exceptional opportunity to own a move-in-ready luxury home in an unparalleled setting.

2 Willow Oak W Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

7 Red Maple Road, Hilton Head Island
$2,575,000
4 Beds ⋅ 4 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-506349 MLS
Gorgeous! Just gorgeous! Extensively renovated in 2022, this beautifully reimagined, single-level, Sea Pines residence blends refined design with exceptional privacy on an oversized (1/2 acre+) property. Relax and recharge and take a refreshing dip in the private pool with scenic golf views beyond, while the cart path on the other side of the fairway adds to the privacy. The open, light-filled interior features hardwood flooring, smooth ceilings with vaulted areas, plantation shutters, and current finishes throughout. A designer chef-inspired kitchen showcases an oversized quartz island, upgraded stainless appliances, recessed LED lighting, and picturesque views from abundant windows and glass. Four (well-positioned) bedrooms, including a large bunk-style room for the youngies, a double garage, AND a new roof in 2022. Note that the leisure trail at the end of the street connects to Plantation Club and the Beach Club!

7 Red Maple Road, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Harbour & Home Real Estate.

50 Plantation Drive, Hilton Head Island
$1,850,000
3 Beds ⋅ 4 Baths ⋅ 2,721 SqFt. ⋅ HILTONHEAD-511600 MLS
Nestled on prestigious Plantation Drive, in amenity-rich Sea Pines Community, this quintessential Tom Parker-designed Sea Pines home enjoys an exceptional location, beneath magnificent live oaks, perfectly situated within near distance to Harbour Town & the SP Beach Club. Set on just under a half-acre overlooking the 8th fairway of Heron Pointe Golf Course, this beautifully updated home offers more than 2,700 square feet of light-filled living space w/timeless charm, elevated first-floor construction, classic brick accents & serene golf course views.Step inside to a welcoming slate-floored entry that opens to hardwood flooring throughout the main living areas & bedrooms.The open-concept kitchen, family room, & living area create an ideal setting for everyday living & entertaining, anchored by a stunning floor-to-ceiling quartz gas fireplace. The beautifully renovated kitchen features custom cabinetry, GE Café & Bosch appliances, a gas range, gorgeous countertops w/hand-made back splash & updated lighting.The thoughtfully designed floor plan includes the primary suite & a guest suite on the main level, w/a spacious third en-suite bedroom above the garage that serves perfectly as a second primary suite or a private guest retreat. All bedrooms feature en-suite baths, & an additional half-bath is conveniently located for guests. The fabulous 550+ square-foot 2025 primary suite addition, offers breathtaking golf course views, a generous walk-in closet, & a luxurious spa-inspired bath featuring a double-sink vanity w/marble countertops & a custom-tiled walk-in shower. Add'l improvements include a comprehensive 2020 renovation with 3 new hurricane-impact sliding glass doors, a beautifully updated kitchen, & new lighting throughout. A GE wash/dryer & a new water heater were installed in 2021, while 2025 upgrades include a new furnace, ductwork, & hurricane-impact garage doors.Outdoor living is equally impressive w/a newly added (2025) covered screened porch measuring approximately 19' x 14', offering stunning golf course views & an adjacent elevated patio-perfect for relaxing or entertaining family & friends.Enjoy the best of Sea Pines with an easy walk or bike ride to Harbour Town or SP Beach Club. Owners enjoy access to miles of pristine beaches, a pvt residents' beach, world-class golf, tennis, marinas, a nature preserve, equestrian stables & countless other amenities. Experience the Sea Pines Lifestyle at its finest, you deserve to love where you live!

50 Plantation Drive, Hilton Head Island

Listing courtesy of C 21 A Low Country Realty. Selling Office: BESTNEST By Beverly Serral.

3 Tupelo Road, Hilton Head Island
$1,299,900
3 Beds ⋅ 2 Baths ⋅ 1,809 SqFt. ⋅ HILTONHEAD-507403 MLS
Private Sea Pines Retreat with Pool & Coastal Vibe! Tucked beneath a canopy of mature oaks in Sea Pines, this inviting 3-bedroom, 2-bath coastal cottage captures the easy, breezy spirit of island living-whether as a primary residence, second home, or short-term vacation rental opportunity. A welcoming circular driveway offers plenty of parking for both owners and guests, setting the tone for relaxed gatherings from the moment you arrive. Inside, the light-filled interior comes alive with elevated ceilings and wide-plank flooring, creating a warm yet airy feel. The open-concept living space is anchored by a fireplace, perfect for cozy evenings, while the living, dining, and kitchen areas flow effortlessly-ideal for entertaining, reconnecting, and simply enjoying time together. The kitchen features generous counter space, stainless steel appliances, and a central island that keeps everyone part of the conversation. The sunroom adds a bright and cheerful retreat, bringing the outdoors in and offering the perfect spot for morning coffee, afternoon reading, or a quiet escape after a day in the sun. The layout provides comfortable bedroom separation, giving both owners and guests space to relax and unwind. Step outside and the lifestyle truly takes over. A private pool, multiple-level decks, and low-maintenance composite decking create the ultimate backdrop for outdoor living-from sunny afternoons poolside to evening dinners under the trees. Surrounded by lush landscaping, the setting feels private, peaceful, and effortlessly coastal. Imagine starting your morning with coffee in the sunroom, biking to the Beach Club by midday, and ending the day with a swim in your private pool as the island quiets down around you. Enjoy easy access to Harbour Town, Lawton Stables, and miles of leisure trails-placing the very best of Sea Pines right at your fingertips. Come experience the energy, the setting, and the lifestyle-this is Hilton Head living at its best. Schedule your private showing today.

3 Tupelo Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Coastal Luxury Real Estate.

40 Planters Wood Drive Unit 2518, Hilton Head Island
$1,060,000
3 Beds ⋅ 3 Baths ⋅ 2,205 SqFt. ⋅ HILTONHEAD-511154 MLS
Beautifully remodeled Sea Pines villa offering the perfect blend of Lowcountry charm and modern updates. Three-bedroom villas in Fairway Oaks rarely become available - don't miss this incredible opportunity! This spacious 3-bedroom, 2.5-bath residence features a rare 2-car garage and stunning cathedral ceilings that create an open, airy living space filled with natural light. The updated kitchen showcases stainless steel appliances, a stylish backsplash, and beautiful finishes throughout. Thoughtful design details include grasscloth wallpaper in the foyer, a wet bar perfect for entertaining, and seamless indoor/outdoor living. The spacious primary suite offers a private retreat complete with a glass walk-in shower and freestanding soaking tub. Enjoy your morning coffee on the screened porch or unwind on the expansive back deck overlooking the peaceful lagoon setting. Ideally located in the heart of Sea Pines just minutes from Harbour Town, this villa is a fantastic opportunity as a full-time residence or second home. Owners enjoy world-class Sea Pines amenities including miles of leisure trails, beach access, the Sea Pines Beach Club, Harbour Town Marina, championship golf courses, tennis and pickleball, Lawton Stables, dining, shopping, and endless Lowcountry recreation. A rare Fairway Oaks offering you won't want to miss!

40 Planters Wood Drive Unit 2518, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

15 Calibogue Cay Road Unit 394, Hilton Head Island
$940,000
2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-512196 MLS
Move‐in-reаdу, Brіаrwοod Vіllаs 394 offers the featurеs еxperienced Sea Pines buyers value: an end-unit, private entrance, single-level living, and one of Briarwood's best golf views-looking directly up the 9th hole of Pete Dye's Heron Point.The two-bedroom, two-bath floor plan includes a flexible office/den and light-filled atrium. Clerestory windows accent the dramatic double-height living-room ceiling, adding architectural interest and abundant natural light. The remodeled kitchen opens to the living area, while built-ins enhance the family room. Painted in 2024, the villa features new LVP flooring in both bedrooms and flex area; new ceiling fans; updated window treatments; and a smooth family-room ceiling. The renewed courtyard/solarium offers overhead screening, leveled new pavers, catch basin drainage, repaired woodwork, and a comfort fan. Pavers also replaced the rear wood deck and service-area stones. With no short-term rentals, a community pool, and a sought-after central Sea Pines address, this is an exceptional right-size opportunity in enduringly desirable Briarwood.

15 Calibogue Cay Road Unit 394, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Sea Pines Real Estate South Beach.

21 Calibogue Cay Road Unit 363, Hilton Head Island
$885,000
2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-504848 MLS
Rare opportunity to own a beautifully positioned 2-bedroom, 2-bath Briarwood villa in Sea Pines, as these villas rarely come on the market. This private end unit offers stunning lagoon and fairway views and is surrounded by lagoon, marsh, and open green space. The light-filled, single-level layout features a completely updated kitchen with stainless steel appliances, open living areas, and high ceilings. Both bathrooms are updated, and the bright Carolina room adds additional living space. Private interior courtyard for outdoor dining or relaxing. Located minutes from Harbour Town, golf, beaches, and Sea Pines leisure trails. Currently furnished but being sold unfurnished.

21 Calibogue Cay Road Unit 363, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Hodde Real Estate.

40 Planters Wood Drive Unit 2519, Hilton Head Island
$829,000
2 Beds ⋅ 2 Baths ⋅ 1,846 SqFt. ⋅ HILTONHEAD-505632 MLS
Totally turnkey and beautifully updated, this 2-bedroom, 2-bath Fairway Oaks villa features a rare 1-car garage and tranquil lagoon views. The kitchen has been updated with granite countertops, stainless steel appliances, and a stylish backsplash, opening to a bright breakfast area. The living room offers vaulted ceilings, an open layout, and a cozy fireplace. The primary bedroom includes an updated walk-in shower, dual vanities, new countertops, and tile. Ideally located just steps from the community pool and close to all that Harbour Town has to offer, this villa also provides convenient access to the amenities of Sea Pines Resort, including multiple beaches, bike trails, golf courses, tennis and pickleball courts, marinas, dining, and 24-hour gated security. Perfect as a primary residence, seasonal home, or investment property.

40 Planters Wood Drive Unit 2519, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Harbour & Home Real Estate.

40 Planters Wood Drive Unit 2507, Hilton Head Island
$825,000
2 Beds ⋅ 2 Baths ⋅ 1,846 SqFt. ⋅ HILTONHEAD-501300 MLS
Welcome to this charming 2 bedroom, 2 bath end-unit villa offering stunning views of the Pete Dye-designed Heron Pointe Golf Course. This well-maintained home features a bright and open layout with a gas fireplace, elegant plantation shutters, and a mix of wood, stone, and carpet flooring throughout. The kitchen boasts granite countertops, perfect for both cooking and entertaining. Step outside to a spacious rear deck and enjoy the serene golf course scenery, or relax in your private courtyard patio with fencing ideal for pets or gardening. Additional features include a 1-car garage, community pool and tennis courts, and the privacy of an end-unit location. Whether you are looking for a primary residence, vacation getaway, or investment property, this villa offers a perfect blend of comfort, style, and location.

40 Planters Wood Drive Unit 2507, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Sea Pines Real Estate South Beach.

70 Lighthouse Road Unit 2875, Hilton Head Island
$1,600
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-507801 MLS
Discover Hilton Head Island at its most inviting during deeded Week 36 in mid-September, a time when the pace slows, the weather remains beautifully warm, and the island takes on a more calm, laid-back feel. Swallowtail at Sea Pines delivers an effortless blend of comfort and coastal elegance, perfectly positioned between the famous Harbour Town lighthouse and the scenic Beach Club. From here, you're just a short stroll or bike ride from top-tier golf courses, unspoiled beaches, waterfront restaurants, and local galleries. Spend your days enjoying quiet sunrise walks along the shore, leisurely rides under canopies of moss-draped oaks, or afternoons on the fairways in ideal early fall conditions. Whether you're seeking relaxation or recreation, everything is within easy reach. Enjoy your autumn getaway your way, with the flexibility to make it truly yours.

70 Lighthouse Road Unit 2875, Hilton Head Island

Listing courtesy of Lighthouse Realty. Selling Office: Lighthouse Realty.

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