Hiltonheadbuy.com Search Results

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.

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.

18 Planters Wood Drive, Hilton Head Island

$2,700,000

SEA PINES COASTAL LUXURY: Panoramic 180-degree green views of stunning Heron Point Fairways and Ridgewood lake! Over 700K in exquisite renovations by legendary Hilton Head builder, this masterful design features wall-to-wall windows, voluminous ceilings in living room, den, stainless steel kitchen and dining. Two spectacular fireplaces. The 3 main floor bedrooms all include beautiful en-suite baths. The second floor offers handsome accommodations for precious family or guests. The new pool and spa offer soothing comfort and privacy! This home is designed for all-on-one-level living and entertaining. Additional features include 2 car attached garage, swing through circular driveway, on a very desirable Sea Pines oversized lot, across this quiet street, from a wooded permanent open area. Just a 10 minute walk or bike to Harbour Town, home of the world famous 18 hole Heritage Golf Classic, and exceptional amenities: golf, tennis, boating, water skiing, fishing, children's playground, multiple shops and restaurants. A short trolley ride takes you to gorgeous, life-guarded Sea Pines Beach Club, with entertainment, oyster roasts, 2 great restaurants, and 2 additional world-class 18 hole golf courses. Less than 15 minute bike ride to Sea Pines Beach Club.

4 Beds ⋅ 5 Baths ⋅ 3,932 SqFt. ⋅ HILTONHEAD-500652 MLS

SEA PINES COASTAL LUXURY: Panoramic 180-degree green views of stunning Heron Point Fairways and Ridgewood lake! Over 700K in exquisite renovations by legendary Hilton Head builder, this masterful design features wall-to-wall windows, voluminous ceilings in living room, den, stainless steel kitchen and dining. Two spectacular fireplaces. The 3 main floor bedrooms all include beautiful en-suite baths. The second floor offers handsome accommodations for precious family or guests. The new pool and spa offer soothing comfort and privacy! This home is designed for all-on-one-level living and entertaining. Additional features include 2 car attached garage, swing through circular driveway, on a very desirable Sea Pines oversized lot, across this quiet street, from a wooded permanent open area. Just a 10 minute walk or bike to Harbour Town, home of the world famous 18 hole Heritage Golf Classic, and exceptional amenities: golf, tennis, boating, water skiing, fishing, children's playground, multiple shops and restaurants. A short trolley ride takes you to gorgeous, life-guarded Sea Pines Beach Club, with entertainment, oyster roasts, 2 great restaurants, and 2 additional world-class 18 hole golf courses. Less than 15 minute bike ride to Sea Pines Beach Club.

18 Planters Wood Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Harbour & Home Real Estate.

$2,575,000

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!

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.

$2,500,000

One of the finest homes in the Harbour Town area, this beautifully updated property offers a perfect blend of Lowcountry charm and modern luxury. Featuring 3 bedrooms, 3.5 baths, a separate office, private pool, and screened porch, this home is completely turnkey and ready to enjoy. The bright, open floor plan showcases high ceilings, new flooring, and an oversized two-car side-entry garage. The newly remodeled kitchen is a showstopper, complete with quartz countertops, stylish backsplash, and a gas range-ideal for entertaining or everyday living. The primary suite and office are conveniently located on the first floor, while each of the bathrooms has been thoughtfully updated. Additional highlights include smooth painted ceilings, a fairway view, and more than $400,000 in recent improvements throughout. Located on one of the most desirable streets in Sea Pines, this home offers the perfect combination of style, comfort, and location-a truly exceptional property.

3 Beds ⋅ 4 Baths ⋅ 3,565 SqFt. ⋅ HILTONHEAD-502230 MLS

One of the finest homes in the Harbour Town area, this beautifully updated property offers a perfect blend of Lowcountry charm and modern luxury. Featuring 3 bedrooms, 3.5 baths, a separate office, private pool, and screened porch, this home is completely turnkey and ready to enjoy. The bright, open floor plan showcases high ceilings, new flooring, and an oversized two-car side-entry garage. The newly remodeled kitchen is a showstopper, complete with quartz countertops, stylish backsplash, and a gas range-ideal for entertaining or everyday living. The primary suite and office are conveniently located on the first floor, while each of the bathrooms has been thoughtfully updated. Additional highlights include smooth painted ceilings, a fairway view, and more than $400,000 in recent improvements throughout. Located on one of the most desirable streets in Sea Pines, this home offers the perfect combination of style, comfort, and location-a truly exceptional property.

24 Ridgewood Lane, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$1,850,000

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!

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.

$1,299,900

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 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

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!

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

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.

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.

15 Calibogue Cay Road Unit 388, Hilton Head Island

$940,000

Ideally situated on prestigious Calibogue Cay Road in the heart of Sea Pines, this beautifully remodeled 3-bedroom, 2-bath Briarwood Villa offers serene views overlooking the 9th fairway of the renowned Heron Point Golf Course - a peaceful backdrop of lush greens and classic Lowcountry charm. Uniquely, this villa is one of only two in the entire Briarwood community that is not part of a four-unit building, offering exceptional privacy and a more residential feel rarely found in this neighborhood. Step inside to discover a thoughtfully redesigned interior showcasing quality craftsmanship and modern finishes throughout. The open-concept floor plan features large tinted glass windows with custom blinds that invite in natural light while maintaining privacy and energy efficiency. Recent upgrades include a new HVAC system and water heater, ensuring year-round comfort and peace of mind. Travertine and luxury vinyl flooring combine elegance with durability, while the primary suite's redesigned bath offers a spa-like retreat with contemporary style and refined details. Outdoor living is equally impressive. Enjoy your morning coffee or evening cocktail in the screened and covered atrium, or relax in the enclosed sunroom while taking in tranquil golf course views. The expanded side yard with new sealed patio pavers provides the perfect setting for grilling and entertaining. A custom storage shed with matching pavers offers convenient space for tools, beach gear, or golf accessories. Nestled within the sought-after Sea Pines community, residents enjoy access to miles of leisure trails, championship golf, world-class tennis, the iconic Harbour Town Lighthouse, and pristine beaches. Whether you're seeking a full-time residence, vacation retreat, or investment property, this exceptional Briarwood Villa delivers the very best of Hilton Head Island living - refined, relaxed, and undeniably Sea Pines.

3 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-502508 MLS

Ideally situated on prestigious Calibogue Cay Road in the heart of Sea Pines, this beautifully remodeled 3-bedroom, 2-bath Briarwood Villa offers serene views overlooking the 9th fairway of the renowned Heron Point Golf Course - a peaceful backdrop of lush greens and classic Lowcountry charm. Uniquely, this villa is one of only two in the entire Briarwood community that is not part of a four-unit building, offering exceptional privacy and a more residential feel rarely found in this neighborhood. Step inside to discover a thoughtfully redesigned interior showcasing quality craftsmanship and modern finishes throughout. The open-concept floor plan features large tinted glass windows with custom blinds that invite in natural light while maintaining privacy and energy efficiency. Recent upgrades include a new HVAC system and water heater, ensuring year-round comfort and peace of mind. Travertine and luxury vinyl flooring combine elegance with durability, while the primary suite's redesigned bath offers a spa-like retreat with contemporary style and refined details. Outdoor living is equally impressive. Enjoy your morning coffee or evening cocktail in the screened and covered atrium, or relax in the enclosed sunroom while taking in tranquil golf course views. The expanded side yard with new sealed patio pavers provides the perfect setting for grilling and entertaining. A custom storage shed with matching pavers offers convenient space for tools, beach gear, or golf accessories. Nestled within the sought-after Sea Pines community, residents enjoy access to miles of leisure trails, championship golf, world-class tennis, the iconic Harbour Town Lighthouse, and pristine beaches. Whether you're seeking a full-time residence, vacation retreat, or investment property, this exceptional Briarwood Villa delivers the very best of Hilton Head Island living - refined, relaxed, and undeniably Sea Pines.

15 Calibogue Cay Road Unit 388, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

21 Calibogue Cay Road Unit 378, Hilton Head Island

$939,000

Great 2 bedroom, 2 bath, Briarwood Villa

2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-511365 MLS

Great 2 bedroom, 2 bath, Briarwood Villa

21 Calibogue Cay Road Unit 378, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: Keller Williams Realty.

21 Calibogue Cay Road Unit 363, Hilton Head Island

$885,000

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.

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

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.

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

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.

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.

21 Calibogue Cay Road Unit 369, Hilton Head Island

$755,000

Located off of quiet Calibogue Cay Road nestled between the marsh and Heron Point Golf Course. One of the best views in Briarwood with lagoon and Heron Point Golf Views across #9 fairway of Heron Point and down #10 fairway. Wood Shutters in every bedroom window, extensive built-in's in both bedrooms, all three walk-in closets feature customized shelving, smooth ceilings and a gorgeous sun room. Seller is a SC licensed referral agent

2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-501739 MLS

Located off of quiet Calibogue Cay Road nestled between the marsh and Heron Point Golf Course. One of the best views in Briarwood with lagoon and Heron Point Golf Views across #9 fairway of Heron Point and down #10 fairway. Wood Shutters in every bedroom window, extensive built-in's in both bedrooms, all three walk-in closets feature customized shelving, smooth ceilings and a gorgeous sun room. Seller is a SC licensed referral agent

21 Calibogue Cay Road Unit 369, Hilton Head Island

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

15 Calibogue Cay Road Unit 391, Hilton Head Island

$749,000

Updated & beautifully furnished, this Briarwood is truly a 3BR all 3 with walk-in closets! Owners built a hallway creating a true 3rd BR, so front 2 BRs can either be J&J bedrooms or a master/office suite. Gorgeous rolling golf view and a large screened porch to enjoy it! Full of natural light with built in bookshelves in the living area. Hardwood flooring. Very private location! Updated kitchen with pantry and brick courtyard for cocktails, dining and grilling! Pool in complex and easy access to Harbour Town!

2 Beds ⋅ 2 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-454270 MLS

Updated & beautifully furnished, this Briarwood is truly a 3BR all 3 with walk-in closets! Owners built a hallway creating a true 3rd BR, so front 2 BRs can either be J&J bedrooms or a master/office suite. Gorgeous rolling golf view and a large screened porch to enjoy it! Full of natural light with built in bookshelves in the living area. Hardwood flooring. Very private location! Updated kitchen with pantry and brick courtyard for cocktails, dining and grilling! Pool in complex and easy access to Harbour Town!

15 Calibogue Cay Road Unit 391, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach. Selling Office: Howard Hanna Allen Tate Hilton Head.

40 Planters Wood Drive Unit 2527, Hilton Head Island

$700,000

Welcome to Fairway Oaks! Unveil the charm of a hidden treasure within the prestigious Sea Pines community! This exceptional 2-bedroom, 2-bathroom end-unit villa offers true one-floor living across 1,800+ sq. ft. of inviting space. Soaring ceilings crown the open living, dining, and kitchen areas, where gleaming hardwood floors and walls of glass showcase serene lagoon views bringing the beauty of the Low Country right inside. Three newly redone Trex decks and a cozy porch provide the perfect spots to relax and enjoy the coastal breeze. An attached one-car garage adds convenience, while the villa itself presents a blank canvas ready for your personal touch. (Sold unfurnished) Fairway Oaks is an intimate 38-villa enclave set on 11 acres of beautifully landscaped grounds. Residents enjoy exclusive access to a private pool, tennis courts, and two pickleball courts. With no short-term rentals allowed, the community offers a true neighborhood feel. Perfectly located near Harbour Town and pristine beaches, this villa is ideal as a primary residence or second home. Rare opportunity! Don't let it slip away! FYI there is room to add space as several identical units have added 200+- additional sq ft. Ask to see the Video. Regime fee monthly is $981 allocated: $417 to Operating Expenses, $213 to Capital Expenses and $351 to Insurance Reserves.

2 Beds ⋅ 2 Baths ⋅ 1,846 SqFt. ⋅ HILTONHEAD-454779 MLS

Welcome to Fairway Oaks! Unveil the charm of a hidden treasure within the prestigious Sea Pines community! This exceptional 2-bedroom, 2-bathroom end-unit villa offers true one-floor living across 1,800+ sq. ft. of inviting space. Soaring ceilings crown the open living, dining, and kitchen areas, where gleaming hardwood floors and walls of glass showcase serene lagoon views bringing the beauty of the Low Country right inside. Three newly redone Trex decks and a cozy porch provide the perfect spots to relax and enjoy the coastal breeze. An attached one-car garage adds convenience, while the villa itself presents a blank canvas ready for your personal touch. (Sold unfurnished) Fairway Oaks is an intimate 38-villa enclave set on 11 acres of beautifully landscaped grounds. Residents enjoy exclusive access to a private pool, tennis courts, and two pickleball courts. With no short-term rentals allowed, the community offers a true neighborhood feel. Perfectly located near Harbour Town and pristine beaches, this villa is ideal as a primary residence or second home. Rare opportunity! Don't let it slip away! FYI there is room to add space as several identical units have added 200+- additional sq ft. Ask to see the Video. Regime fee monthly is $981 allocated: $417 to Operating Expenses, $213 to Capital Expenses and $351 to Insurance Reserves.

40 Planters Wood Drive Unit 2527, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: ERA Evergreen Real Estate Company.

70 Lighthouse Road Unit 2889, Hilton Head Island

$3,500

Rare 2-Week Ownership: Own an extended summer escape! This deeded ownership of consecutive Weeks 31 and 32 in Swallowtail's Unit 2889 offers a unique opportunity to experience the best of Sea Pines without interruption. Enjoy a serene, golf course view of Heron Point from your island retreat. Perfectly located across the street from the Shops at Sea Pines Center where you'll find designer boutiques and dining or enjoy Harbour Town's lighthouse, dining, and shopping, as well as the sun-drenched beaches of the Beach Club. Ideal for those who crave a longer, more relaxed vacation. Make this your annual two-week paradise!

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-501335 MLS

Rare 2-Week Ownership: Own an extended summer escape! This deeded ownership of consecutive Weeks 31 and 32 in Swallowtail's Unit 2889 offers a unique opportunity to experience the best of Sea Pines without interruption. Enjoy a serene, golf course view of Heron Point from your island retreat. Perfectly located across the street from the Shops at Sea Pines Center where you'll find designer boutiques and dining or enjoy Harbour Town's lighthouse, dining, and shopping, as well as the sun-drenched beaches of the Beach Club. Ideal for those who crave a longer, more relaxed vacation. Make this your annual two-week paradise!

70 Lighthouse Road Unit 2889, Hilton Head Island

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

70 Lighthouse Road Unit 2893, Hilton Head Island

$2,100

Swallowtail at Sea Pines, Week 19 falls during a peaceful, sought after time of year making it an ideal retreat for those who appreciate Sea Pimes at iots most relaxing. The perfect timing to enjoy Hilton Head's glorious spring weather. This end-unit villa in prestigious Sea Pines offers exceptional natural light and one of the best golf views in all of Swallowtail-a sweeping panorama of the tee box across the fairway and lagoon to the par-3 green. Enjoy world-class golf, scenic bike paths, Harbour Town, and the Sea Pines Beach Club just moments away. Experience the Lowcountry lifestyle year after year in your own Hilton Head getaway.

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-502765 MLS

Swallowtail at Sea Pines, Week 19 falls during a peaceful, sought after time of year making it an ideal retreat for those who appreciate Sea Pimes at iots most relaxing. The perfect timing to enjoy Hilton Head's glorious spring weather. This end-unit villa in prestigious Sea Pines offers exceptional natural light and one of the best golf views in all of Swallowtail-a sweeping panorama of the tee box across the fairway and lagoon to the par-3 green. Enjoy world-class golf, scenic bike paths, Harbour Town, and the Sea Pines Beach Club just moments away. Experience the Lowcountry lifestyle year after year in your own Hilton Head getaway.

70 Lighthouse Road Unit 2893, Hilton Head Island

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

70 Lighthouse Rd Unit 2870, Hilton Head Island

$1,800

Own Your Summer Escape at Swallowtail in Sea Pines! One deeded June week (Week 24) is available in this highly sought-after Hilton Head Island community. Perfectly positioned between Harbour Town's iconic lighthouse and the sun-drenched Beach Club, Swallowtail offers effortless access to championship golf, pristine beaches, waterfront dining, and a vibrant arts scene. Enjoy the best of early summer - warm ocean breezes, uncrowded beaches, sunset sails, and evenings spent strolling Harbour Town. Embrace a luxurious, low-maintenance coastal lifestyle just steps from the sand and Sea Pines' premier amenities. Act now to claim your piece of paradise!

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-503750 MLS

Own Your Summer Escape at Swallowtail in Sea Pines! One deeded June week (Week 24) is available in this highly sought-after Hilton Head Island community. Perfectly positioned between Harbour Town's iconic lighthouse and the sun-drenched Beach Club, Swallowtail offers effortless access to championship golf, pristine beaches, waterfront dining, and a vibrant arts scene. Enjoy the best of early summer - warm ocean breezes, uncrowded beaches, sunset sails, and evenings spent strolling Harbour Town. Embrace a luxurious, low-maintenance coastal lifestyle just steps from the sand and Sea Pines' premier amenities. Act now to claim your piece of paradise!

70 Lighthouse Rd Unit 2870, Hilton Head Island

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

70 Lighthouse Road Unit 2875, Hilton Head Island

$1,600

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.

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.

70 Lighthouse Realty Unit 2882, Hilton Head Island

$1,300

Own Your Summer Escape – Make Hilton Head your summer tradition! Enjoy prime summer living with deeded ownership of Week 33 at Swallowtail, nestled in the heart of Hilton Head Island’s prestigious Sea Pines community. Perfectly positioned between the iconic Harbour Town Lighthouse and the Beach Club, this property places you steps from world-class golf, white-sand beaches, waterfront dining, and vibrant cultural events. Experience the best of coastal living—spend mornings on the beach, sail into stunning sunsets, and soak in the charm of Harbour Town. With luxurious, low-maintenance ownership, your summer getaway is always waiting.

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-454317 MLS

Own Your Summer Escape – Make Hilton Head your summer tradition! Enjoy prime summer living with deeded ownership of Week 33 at Swallowtail, nestled in the heart of Hilton Head Island’s prestigious Sea Pines community. Perfectly positioned between the iconic Harbour Town Lighthouse and the Beach Club, this property places you steps from world-class golf, white-sand beaches, waterfront dining, and vibrant cultural events. Experience the best of coastal living—spend mornings on the beach, sail into stunning sunsets, and soak in the charm of Harbour Town. With luxurious, low-maintenance ownership, your summer getaway is always waiting.

70 Lighthouse Realty Unit 2882, Hilton Head Island

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

70 Lighthouse Road Unit 2879, Hilton Head Island

$750

Discοver your реrfeсt ѕрring rеtrеat at Swallowtail іn Sеa Pines with Week 10 ownership! Set in the heart of Hilton Head Island, this mid-March getaway offers a refreshing change of pace, with mild coastal weather, blooming scenery, and a more relaxed island vibe. Overlooking the 12th fairway of the Heron Point Golf Course, the property combines scenic golf views with easy access to everything that makes Sea Pines so special. You're just a short distance from the Harbour Town lighthouse, the Beach Club, and an array of dining, shopping, and outdoor experiences. Spend your days enjoying early rounds of golf, beach walks, or biking beneath moss-draped oaks, and your evenings unwinding in the charm of Harbour Town. With its low-maintenance ownership and prime location, Swallowtail offers an effortless way to enjoy Hilton Head year after year. Take advantage of this opportunity to claim your own slice of Sea Pines in one of the island's most inviting seasons-Week 10 is waiting.

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-506994 MLS

Discοver your реrfeсt ѕрring rеtrеat at Swallowtail іn Sеa Pines with Week 10 ownership! Set in the heart of Hilton Head Island, this mid-March getaway offers a refreshing change of pace, with mild coastal weather, blooming scenery, and a more relaxed island vibe. Overlooking the 12th fairway of the Heron Point Golf Course, the property combines scenic golf views with easy access to everything that makes Sea Pines so special. You're just a short distance from the Harbour Town lighthouse, the Beach Club, and an array of dining, shopping, and outdoor experiences. Spend your days enjoying early rounds of golf, beach walks, or biking beneath moss-draped oaks, and your evenings unwinding in the charm of Harbour Town. With its low-maintenance ownership and prime location, Swallowtail offers an effortless way to enjoy Hilton Head year after year. Take advantage of this opportunity to claim your own slice of Sea Pines in one of the island's most inviting seasons-Week 10 is waiting.

70 Lighthouse Road Unit 2879, Hilton Head Island

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

Premium Properties of Hilton Head

Search

Resources

About