323 listings, but only 250 max can be displayed.
Sort by
226 S Sea Pines Drive Unit 1592, Hilton Head Island
$900,000
2 Beds ⋅ 2 Baths ⋅ 1,086 SqFt. ⋅ HILTONHEAD-503952 MLS
An amazing opportunity to own an updated South Beach Lagoon Villa. This rare 1086 SF 2-bedroom, 2-bath villa features an updated kitchen and bathrooms. The spacious living area has a shiplap vaulted ceiling, and large patio doors that open to a very generous deck, providing tranquil water views. Just a short walk/bike ride to South Beach, South Beach Marina and the iconic Salty Dog make this the perfect getaway for relaxation and fun. Smooth ceilings throughout added insulation in the crawl space and roof area. The condo comes fully furnished and includes 2 designated parking spaces, a large storage closed and outdoor shower. This spacious and bright villa is perfect as a second home or rental investment property.

226 S Sea Pines Drive Unit 1592, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: The Hilton Head Agency.

226 S Sea Pines Drive Unit 1585, Hilton Head Island
$900,000
2 Beds ⋅ 2 Baths ⋅ 1,086 SqFt. ⋅ HILTONHEAD-501169 MLS
Fantastic South Beach Villa! This rare 2-bedroom, 2-bath Lagoon Villa in Sea Pines offers tranquil water views and comes with all new furnishings! Thoughtfully updated, it features smooth ceilings, just painted in, huge Trex deck with lighting, and a storage shed. Enjoy a brick entryway, an extended rear deck overlooking the serene lagoon, and the convenience of 2 dedicated parking spaces. Just a short walk to the beach, South Beach Marina, and the iconic Salty Dog, this villa is ideally located for relaxation and fun. With a strong regime and a history of never being rented, it's perfect as a second home or could serve as a desirable rental investment. Regime fee is quarterly

226 S Sea Pines Drive Unit 1585, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Sea Pines Real Estate - Beach Club.

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.

1 Stoney Creek Road Unit 265, Hilton Head Island
$885,000
3 Beds ⋅ 3 Baths ⋅ 1,750 SqFt. ⋅ HILTONHEAD-502909 MLS
Exceptional Lowcountry living at its best with sweeping marsh-to-sound views. Beautifully updated 3-bedroom, 3-bath townhouse villa featuring a newer kitchen opening to a light and bright dining area, a two-story great room and newly renovated bathrooms, along with a highly desirable first-floor bedroom. Nearly every room, including the primary suite captures stunning water views, filling the home with light and coastal charm. Enjoy an oversized rear patio perfect for relaxing or entertaining while overlooking the marsh. The community offers a lovely pool, and the location is unbeatable-just a short walk to the world-renowned Harbor Town Marina with its boutique shops, restaurants, tennis, and championship golf. A rare opportunity to own a truly special property with unmatched views and amenities

1 Stoney Creek Road Unit 265, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

25 Shell Ring Road, Hilton Head Island
$880,000
3 Beds ⋅ 3 Baths ⋅ 2,045 SqFt. ⋅ HILTONHEAD-504192 MLS
Tucked within the serene enclave of Carolina Place, this beautifully appointed three-bedroom home blends comfort, convenience, and Lowcountry charm. A private elevator offers effortless access to all levels, making the home as functional as it is elegant. Wake up to peaceful lagoon views and enjoy the natural beauty that surrounds the property. Large windows and an open layout bring in abundant light, creating a warm, welcoming atmosphere throughout. Residents of Carolina Place enjoy an impressive suite of amenities just steps from the front door. Spend your days relaxing by the community pool, unwinding in the sauna, or staying active on the tennis and pickleball courts. The neighborhood's tranquil setting and lush landscaping make it one of Sea Pines' most desirable hideaways.Whether you're seeking a full-time residence, a vacation escape, or an investment opportunity, this home offers the perfect blend of luxury, leisure, and coastal living.

25 Shell Ring Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

13 Lawton Drive Unit 72, Hilton Head Island
$880,000
2 Beds ⋅ 2 Baths ⋅ 1,100 SqFt. ⋅ HILTONHEAD-502880 MLS
Experience true luxury at 72 Fairway Lane Villas, a beautifully renovated 2-bedroom, 2-bath Villa situated on one of Sea Pines Plantation's most expansive & serene Golf & lagoon views. This stunning Villa has been meticulously transformed, boasting a complete top-to-bottom renovation that includes brand-new kitchen, baths, flooring, ceiling changes, plus too many upgrades to include here. The open-concept living spaces are bright & airy, perfectly designed for entertaining or a quiet family retreat. The updated kitchen features high-end appliances & finishes, while the spacious bedrooms & elegant bathrooms offer comfort & sophistication. Step outside to the expansive paver patio & enjoy the tranquil Golf & Lagoon views creating your own personal oasis. Beyond the doors of this magnificent property, you are immersed in the unparalleled lifestyle of Sea Pines Plantation. This world-renowned gated community is a playground of amenities, from championship golf courses like the famous Harbour Town Golf Links & Atlantic Dunes to the top-tier Sea Pines Racquet Club. One of the most significant advantages of this location is the easy access to the Atlantic Ocean beach. A short walk or bike ride from 72 Fairway Lane Villas puts you at the Sea Pines beachfront via numerous direct beach access paths for a more secluded experience. A short distance to Sea Pines Beach Club, a world-class oceanfront destination with dining, restrooms, & a relaxed atmosphere. The community also offers additional amenities including the iconic Harbour Town with its famous lighthouse, diverse dining & shopping at South Beach Marina Village, & the serene Sea Pines Forest Preserve. In addition to its appeal as a primary residence or personal getaway, 72 Fairway Lane Villas presents an exceptional short-term rental investment opportunity. Sea Pines Plantation is one of the most desirable & high-demand rental markets on the East Coast and, with a consistent flow of visitors year-round. The comprehensive renovation means the property will likely command top-tier rental rates & attract five-star reviews from guests who appreciate modern amenities & a turn-key experience. The property's convenient location with easy access to the beach, bike paths, & all of Sea Pines' world-class attractions ensures strong occupancy & repeat bookings. Sea Pines is one of the few communities on the island where short-term rentals are a core part of the economy, & the demand for quality properties is robust.

13 Lawton Drive Unit 72, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: RE/MAX Island Realty.

125 Greenwood Drive Unit APT 3426, Hilton Head Island
$879,000
3 Beds ⋅ 2 Baths ⋅ 1,279 SqFt. ⋅ HILTONHEAD-506945 MLS
Completely renovated and ideally positioned as a desirable end unit, this beautifully updated villa in Sea Pines offers effortless coastal living with serene lagoon views. Thoughtfully redesigned from top to bottom, the home features a stunning kitchen with quartz countertops, top-of-the-line appliances including a Sub-Zero refrigerator, and an open, light-filled layout perfect for everyday living and entertaining. Brand new bathrooms reflect a clean, modern aesthetic, while all-new furnishings create a turnkey experience. Step outside to a spacious rear deck overlooking the water, ideal for relaxing or gathering with guests. Additional highlights include durable composite siding and a prime location within one of Hilton Head Island's most sought-after communities. Enjoy access to Sea Pines' renowned amenities, all set in a balance of privacy, convenience, and natural beauty.

125 Greenwood Drive Unit APT 3426, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Collins Group Realty.

18 Lighthouse Lane Unit 1033, Hilton Head Island
$878,000
3 Beds ⋅ 3 Baths ⋅ 1,532 SqFt. ⋅ HILTONHEAD-501140 MLS
Elevate your Heritage experience this year in one of Hilton Head Island's most iconic waterfront settings! This 3-bedroom, 3-bathroom Harbour Town villa offers 1,532 square feet of furnished, turnkey living with unforgettable Harbour Town and lighthouse views. A rare opportunity for immediate enjoyment or a blank canvas for your own design vision within a newly updated building, this quiet and serene villa combines comfort with unmatched access to Hilton Head's most celebrated attractions. Relax on your private balcony overlooking the harbour, or explore the waterfront dining at the Quarterdeck, boutique shopping, leisure trails through the Sea Pines Forest Preserve, championship golf at Harbour Town Golf Links, and the Sea Pines Beach Club - all just moments away. A premier opportunity in one of the island's most desirable destinations.

18 Lighthouse Lane Unit 1033, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: Collins Group Realty.

101 Lighthouse Road Unit 2245, Hilton Head Island
$875,000
3 Beds ⋅ 3 Baths ⋅ 1,750 SqFt. ⋅ HILTONHEAD-502186 MLS
You'll love this terrific 2 story townhouse villa offering best 3 bedroom floor plan in Sea Pines. As an end unit, this villa affords supreme privacy to primary suite while the extra windows on the first and second floors creates light filled rooms. The floor plan provides great bedroom separation with one bedroom and one full bathroom downstairs and 2 bedrooms with 2 full bathrooms upstairs. The upstairs bedrooms are separated by a loft seating area that's perfect for reading or desk space. The living room has a tall vaulted ceiling with windows soaring to the top that enhances the open airiness of this villa. Stone floors are found throughout the living room, kitchen and dining area. Upgrade kitchen cabinets, stainless steel appliances. Smooth ceilings throughout. HVAC new in 2023 and both sliding glass doors replaced in 2021. Wonderful outdoor living space situated on a large and private patio that's surround by lush vegetation. You'll find the grill, table and chairs ready for entertaining and dining alfresco. Loads of storage space for your beach gear and personal items. Close to the swimming pool and only a short stroll to all of the world class amenities at Harbour Town. Presently on the Sea Pines Resort rental program with lots of owner usage.

101 Lighthouse Road Unit 2245, Hilton Head Island

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

6 Possum Lane, Hilton Head Island
$870,000
3 Beds ⋅ 2 Baths ⋅ 1,440 SqFt. ⋅ HILTONHEAD-502625 MLS
Coastal inspired updates and over $35,000 in recent enhancements have taken this ultra-charming home in Sea Pines to a new level! Situated on a peaceful residential street with no through traffic, this is truly a gorgeous home that lives large without all the extra fluff! Featuring a show-stopping primary bathroom remodel, high ceilings, remarkably spacious bedroom suites, and a nautical themed bunk room that should be featured in a magazine! Enjoy a seamless connection between all the living spaces, and you will love spending time in the updated kitchen which offers quartz counters, a herringbone backsplash, and premium stainless-steel appliances. Tall ceilings, shiplap, and a wood-burning fireplace add abundant character, while additional highlights such as a new paver driveway (2024), new HVAC (2024), smart thermostat, and a private backyard lawn come together to make this a rare find in Sea Pines! The current owners invested thoughtfully to make this house a home; however, life plans simply shifted sooner than expected, creating a wonderful opportunity that does not come around all that often at this price point. Kitchen will be left fully equipped, furnishings negotiable.

6 Possum Lane, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

2545 Gleneagle Lane Unit 2545, Hilton Head Island
$869,000
2 Beds ⋅ 3 Baths ⋅ 1,600 SqFt. ⋅ HILTONHEAD-508068 MLS
A rare find! A two bedroom Gleneagle Green Villa overlooking the 2nd hole with views of the 3rd and 6th fairways of famed Harbour Town Links Golf Course! With only 20 villas, opportunities to purchase in this exclusive community are exceptionally rare. Privately located, with easy access to The Shoppes and Restaurants of Sea Pines Center and trolley stop. Pride of ownership is evident throughout this turn key townhome style condo. The Great Room and spacious Primary En-Suite have sweeping views of the golf course. Eat- in kitchen has access to a deck for morning coffee and the Great Room rear deck for drinks and view the golfing action. A must see for enjoying a front row seat to the Heritage Golf Tournament and year around pleasure. Make 2545 Gleneagle Green your Island home, or the flexibility of rental guests.

2545 Gleneagle Lane Unit 2545, Hilton Head Island

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

15 Lighthouse Road Unit 32, Hilton Head Island
$865,000
3 Beds ⋅ 2 Baths ⋅ 1,750 SqFt. ⋅ HILTONHEAD-500194 MLS
This 3-bedroom, 2.5-bath villa in close proximity to the beach has stunning views of the 11th fairway of the acclaimed Atlantic Dunes Golf Course. The current owners opened the kitchen by removing a wall, complete renovation of the kitchen with silestone countertops and premium appliances, and converted the screened porch area to what is now the Great room. This property features August 2025 HVAC, all tile/hardwood flooring, open floor plan, and the upper level houses 2 guest suites and 1 bath. This villa offers comfort, style, views, and incredible income potential with a gross rental projection of $54,900. Sea Pines offers world class amenities to include 2 beach clubs, restaurants, shopping, golf, tennis, pickleball, and 2 marinas.

15 Lighthouse Road Unit 32, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate - Beach Club.

23 Bateau Road, Hilton Head Island
$860,000
3 Beds ⋅ 3 Baths ⋅ 2,281 SqFt. ⋅ HILTONHEAD-501829 MLS
Excellent INVESTMENT/FIXER UPPER opportunity in Hilton Head Island's finest resort community, Sea Pines, nestled in a cul-de-sac on one of the nicest streets. Featuring 3 bedrooms and 2.5 baths, the thoughtful Lowcountry style floor plan places the spacious primary suite on the main level for convenience and privacy. Inside, you'll find a formal dining room, and an eat-in kitchen with a laundry room just adjacent. The living room/great room is ready for your vision and updates. Upstairs, two additional bedrooms and a full bath provide plenty of space for family or guests. The exterior showcases classic Lowcountry style, featuring an inviting front porch with a front porch swing, a large rear screened porch, mature trees, and coastal landscaping. The cul-de-sac location offers peace and privacy while still being just minutes from Sea Pines world-class amenities: Harbour Town, the Beach Club, championship golf, and miles of leisure trails. An excellent opportunity to create your dream home in one of Hilton Head Island's most desirable communities. This is priced for your imagination to live the life you have been dreaming about.... Being sold "As Is" Seller to make no repairs including CL-100.

23 Bateau Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners. Selling Office: Sea Pines Real Estate - Beach Club.

75 Lawton Road, Hilton Head Island
$856,000
3 Beds ⋅ 2 Baths ⋅ 1,652 SqFt. ⋅ HILTONHEAD-510682 MLS
Here's your chance to own a slice of paradise in the world-famous Sea Pines Resort on Hilton Head Island, recently voted the #1 Island in the U.S. by Condé Nast Traveler readers. This 3BR/2BA coastal retreat offers the perfect blend of lifestyle, location, and short-term rental potential in one of Hilton Head's most sought-after resort communities. Tucked inside Sea Pines, this home features a comfortable floor plan, inviting living spaces, and a wonderful screened-in porch where you can relax after a day at the beach, on the golf course, or exploring the island by bike. You'll love being within near distance to Hilton Head's beautiful white-sand beaches and the Sea Pines Forest Preserve, with Harbour Town, South Beach Marina Village, The Salty Dog Cafe, dining, shopping, tennis, golf, bike trails, and world-class resort amenities just a short bike ride away. For buyers looking for rental income potential, this is an exciting opportunity. Be sure to review the conceptual pool plan-similar-sized updated homes in this area with pools are grossing $95K+ annually on the short-term rental market. Whether you're searching for a vacation home, investment property, or your own Lowcountry island getaway, this Sea Pines home offers the chance to create something truly special. Take the first step toward your Hilton Head Island lifestyle. Schedule your in-person or live video walkthrough today.

75 Lawton Road, Hilton Head Island

Listing courtesy of EXP Realty LLC. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

2 Woodbine Place Unit 56, Hilton Head Island
$855,000
2 Beds ⋅ 2 Baths ⋅ 1,088 SqFt. ⋅ HILTONHEAD-507385 MLS
Rare opportunity to own a beautifully upgraded end unit in the desirable Woodbine Villas within Sea Pines Resort. Meticulously maintained and in pristine condition, this villa offers a bright, open floor plan with excellent bedroom separation, ideal for both personal enjoyment and guests. Enjoy serene lagoon and phenomenal golf course views overlooking Heron Point by Pete Dye from the spacious indoor-outdoor patio and Carolina Room. Perfectly positioned just a short stroll to Sea Pines Beach Club, Fraser's Tavern, and miles of leisure trails beneath iconic Live Oaks. This villa is not only a peaceful retreat but also a strong investment opportunity, this is a rare chance to own a standout property in one of Hilton Head's most sought-after communities.

2 Woodbine Place Unit 56, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate. Selling Office: Greenplate Group Brokered by eXp Realty.

2041 Deer Island Road, Hilton Head Island
$852,500
2 Beds ⋅ 2 Baths ⋅ 960 SqFt. ⋅ HILTONHEAD-508229 MLS
Completely remodeled in 2022! This marshfront Deer Island perfectly blends the beauty of the Lowcountry with modern coastal living. Quality work throughout with no surface untouched, mini splits, tankless water heater, well designed kitchen, updated bathrooms and spacious bedrooms along with an additional loft bed and ample closet space. Flex space below that's currently used as additional sleeping quarters. Catch sunrise with coffee or the day's end with a cocktail from the TREX deck overlooking the marsh and take in everything Hilton Head and the Lowcountry are about! Currently on the short-term rental market but would make a great second or primary home with its supreme functionality. No two Deer Islands are the same and this one stands out!

2041 Deer Island Road, Hilton Head Island

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

2 Woodbine Place Unit 47, Hilton Head Island
$850,000
2 Beds ⋅ 2 Baths ⋅ 1,088 SqFt. ⋅ HILTONHEAD-507799 MLS
Beautifully remodeled with modern coastal finishes, this 2BR/2BA Woodbine Villa combines an unbeatable walk-to-the-beach location with serene golf views! Both Sea Pines Beach Club and Plantation Golf Club are just a quick stroll down the bike path, while #47 Woodbine still provides a peaceful, private, cul de sac location in Sea Pines. Flanked by ancient live oaks and giant magnolia trees, this corner unit overlooking the 12th green on Atlantic Dunes golf course and has been completely refreshed with wide plank engineered wood floors, white quartz kitchen counters, stainless appliances, smooth ceilings with recessed lighting and subway tile accents in the kitchen and baths. Nothing was left untouched! Unwind on the brick paver back patio watching golf, or relax in a stunning, light-filled sunroom wrapped in walls of windows. A light bright, single level, pet-friendly community in Sea Pines. Absolutely perfect as your 2nd home beach retreat, vacation rental investment or primary bungalow. This property is a WOW and won't last!

2 Woodbine Place Unit 47, Hilton Head Island

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

74 Otter Road, Hilton Head Island
$850,000
4 Beds ⋅ 3 Baths ⋅ 2,191 SqFt. ⋅ HILTONHEAD-504096 MLS
Brand new price at $874,900 - Located within the prestigious Sea Pines community on Hilton Head Island, Club Course is a sought-after neighborhood known for its tranquil setting and proximity to world-class amenities. This 4BD/3BA 2,191sqft home is the perfect place to make your own island getaway. With two of the bedrooms located on the first floor, and the other two upstairs, this layout is perfect for any family. Open floor plan with remodeled kitchen including new appliances, quartz counter tops, LVP flooring throughout, elegant hard coat stucco on the exterior. Kitchen opens up into a cozy living room with a wood fireplace. Step out from the master suite OR the dining room onto one of two inviting decks that span the back of the home. These outdoor retreats seamlessly blend indoor comfort with open-air living, perfect for relaxing or entertaining year-round. There IS room for a pool and another perk is that the lot is located next to a non-buildable lot owned by Sea Pines - green space! Sea Pines is home to championship golf, several private dining options, pristine beaches, and a rich Lowcountry legacy. Don't miss your only opportunity to own a 4BD home in Sea Pines under $875,000!

74 Otter Road, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

20 Governors Road Unit APT 2825, Hilton Head Island
$850,000
2 Beds ⋅ 2 Baths ⋅ 1,477 SqFt. ⋅ HILTONHEAD-501582 MLS
2 Bdr/2 Ba all on one floor in the highly coveted Residents Club. with a 1 car carport and driveway with a large, secured storage closet. It was renovated in 2024 and move in ready! New Paint. New Flooring, New stainless-steel appliances and tile backsplash, 2 New Skylights in Breakfast area, no fogged Windows in Living Room. New Roof is 2020. New Lighting, New Sink & Toilet in Hallway Bathroom. Smooth ceilings, New solid interior doors and Sunroom exterior door. Back deck and stairs have been improved. Front Paver Courtyard with a private wall adds to your own outdoor living area and a very welcoming front entrance. Gutters were added in back in 2024. No short-term rentals. There is a Private Residents Club Pool and close to the Sea Pines Country Club if you wish to join. Back deck has golf views of the 10th hole. Residents Club rarely come on the market...don't miss this one. Close proximity to Sea Pines front security gate. An easy drive to your new home and all the truly amazing amenities and beach access that Sea Pines has to offer.

20 Governors Road Unit APT 2825, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty. Selling Office: Home By The Sea Realty, LLC.

4 Braddock Bluff Drive Unit 1692, Hilton Head Island
$835,000
2 Beds ⋅ 2 Baths ⋅ 1,186 SqFt. ⋅ HILTONHEAD-512379 MLS
Locаted in world‐fаmouѕ Ѕеa Ρіnes Resort in the іcοnic South Beach community, 1692 Bluff Villa is just steps across the street from the Atlantic Ocean beaches and an easy stroll to the legendary Salty Dog and South Beach Marina Village. This 2BR/2BA beautifully appointed penthouse villa puts dining, shopping, boating and coastal fun right at your doorstep. Interior features include 10 ft-plus smooth ceilings in the main living areas - only available to top floor properties - stone tile floors, remodeled baths with granite counters and a walk-in shower, custom trim and an open floor plan. Both bedrooms are generous in size and feature many windows, tray ceilings with cove lighting and 8" baseboards, creating a light, luxury feel with plenty of room to relax. The completely renovated kitchen features custom, coastal cottage-style cabinets, granite countertops and stainless appliances and flows seamlessly into the living, dining and outdoor covered balcony areas. Catch a Lowcountry breeze on the private terrace, take a dip in the neighborhood pool or enjoy the 5-star amenities of Sea Pines including championship golf and tennis, miles of leisure trails, renowned Harbour Town and the scenic yacht basin and exceptional dining and shopping. A proven rental producer, a popular vacation destination and one-of-a-kind location next to the beach, 1692 Bluff Villa represents the ideal vacation getaway, investment property and Sea Pines second home retreat!

4 Braddock Bluff Drive Unit 1692, Hilton Head Island

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

10 Hollyberry Lane, Hilton Head Island
$835,000
2 Beds ⋅ 2 Baths ⋅ 1,516 SqFt. ⋅ HILTONHEAD-507616 MLS
This charming two-bedroom, two-bathroom home is nestled in the desirable Greenwood Forest community, right in the heart of Sea Pines. Surrounded by mature landscapingi, the property offers a private backyard retreat-perfect for enjoying a quiet, relaxed Lowcountry setting. Whether as a primary residence, second home, or investment opportunity, this home presents a wonderful chance to own in one of Hilton Head Island's most sought-after communities. Sweet jasmine and azaleas bloom on the property during the Heritage Golf Tournament each spring, adding to the Lowcountry charm of this special setting. Just steps from the shared Greenwood Forest amenities, a wooded trail leads directly behind The Shops at Sea Pines Center. Grab a morning coffee, pick up a pizza, enjoy breakfast at Lowcountry Produce, or settle in for a fine-dining dinner at Truffles-all just about a three-minute walk from the property. The beach is approximately 0.8 miles away, with Harbour Town approximately 1.5 miles from the property. Not all locations inside the gates of Sea Pines are the same, and this is truly one of its best central locations. Sit on your back patio beneath the Lowcountry's umbrella of protected live oaks and hear the distant sound of the ocean through the trees. Experience the lifestyle that makes Sea Pines so special-and make your move today! THE REGIME FEE IS 334/yr not per month it reads monthly but it is yearly. One of the lowest regime fees in all of Sea Pines.

10 Hollyberry Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: EXIT Hilton Head Realty.

5 Braddock Bluff Drive Unit 1760, Hilton Head Island
$835,000
2 Beds ⋅ 2 Baths ⋅ 1,186 SqFt. ⋅ HILTONHEAD-506724 MLS
Stunning top-to-bottom renovated 2-bedroom, 2-bath Bluff Villa with high-end finishes and breathtaking water views. This exceptional end unit is truly one of the most beautiful Bluff Villas you will ever see. Located in the highly desirable South Beach area of Sea Pines, next to the world famous Salty Dog, and just across the street from the beach, the setting is unmatched. Designed with style and quality in mind, it features an open kitchen with white quartz countertops, soft-close white cabinetry, stainless GE appliances, and a quartz wine bar with a wine cooler. Additional upgrades include smooth ceilings, crown molding, engineered hardwood flooring, plantation shutters throughout, beautifully updated baths, and custom built-ins in both bedrooms. Enjoy waterfront views from your private balcony. Ideal as a primary residence, second home, or investment property.

5 Braddock Bluff Drive Unit 1760, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Charter One Realty.

108 Sea Pines Drive Unit APT 548, Hilton Head Island
$835,000
2 Beds ⋅ 2 Baths ⋅ 1,415 SqFt. ⋅ HILTONHEAD-503553 MLS
Just across the street from the Sea Pines Beach Club and Plantation Club, this desirable ocean course villa offers a newly remodeled interior with all-new flooring, new kitchen cabinets, updated plumbing and more! The sought-after layout features two spacious bedrooms plus a den currently used as a third bedroom, providing excellent flexibility for owners and guests. High ceilings and generous natural light create an airy, inviting feel, while the screened porch offers serene, panoramic views of the Atlantic Dunes golf course and tranquil lagoon. Perfectly positioned near the beach and golf-this is a rare opportunity to own a move-in-ready villa in one of Sea Pines' most desirable locations. Enjoy in its current use as a popular short-term rental or keep it just for yourself. Sold AS IS

108 Sea Pines Drive Unit APT 548, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

55 Night Heron Lane, Hilton Head Island
$830,000
3 Beds ⋅ 2 Baths ⋅ 928 SqFt. ⋅ HILTONHEAD-503315 MLS
Welcome home to easy, breezy Sea Pines living. Night Heron homes are the ideal mix of great value and easy beach access, with onsite pool: a winning combination! This home features open plan living with loads of natural light and a wide lagoon view. The primary bedroom/bath and guest bedroom plus full bath are located on the main level, with a sleeping loft above. Outdoor amenities include a lovely deck overlooking the water, new outdoor shower space, and great storage for beach and other items (part or all can be locked). Easy parking and pool located directly across from the house are also fabulous features-- but best of all is the quick less than 5 minutes walk to beach! Do not delay!

55 Night Heron Lane, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral. Selling Office: Hilton Head Real Estate Partners.

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.

108 Lighthouse Road Unit 2372, Hilton Head Island
$820,000
3 Beds ⋅ 3 Baths ⋅ 1,805 SqFt. ⋅ HILTONHEAD-501505 MLS
Stunning Updated 3BR/3BA Sea Pines Golf Condo - Walk to Harbour Town! Welcome to 2372 Racquet Club, an impeccably updated Sea Pines golf-side condo offering the perfect blend of comfort, convenience, and Lowcountry charm. Overlooking gorgeous fairway views and just a short stroll to iconic Harbour Town, this beautifully furnished 3-bedroom, 3-bath villa is the ideal Hilton Head getaway. Interior Highlights Fully updated kitchen with granite countertops and new cabinets Modernized bathrooms with new tile showers Stylish, comfortable furnishings throughout Sleeps up to 9 - King bedroom downstairs - King bedroom upstairs with brand-new furniture - Guest room with queen + twin- Fold-out couch in the living room Resort-Style Amenities Tennis courts just steps behind the condo Sparkling community pool nearby Bike paths at your doorstep Sea Pines Trolley stop right next to the complex-easy access to the Sea Pines Beach Club Vacation rental includes complimentary bike rentals and beach gear Unbeatable Location. Enjoy serene golf-course views from your back patio and walk to Harbour Town to admire the yachts, dine at Crazy Crab or Quarterdeck, and take in the island's best sunsets. Hop on your bike or the trolley to experience miles of Hilton Head's pristine beaches. Whether you're seeking a luxury vacation rental or the perfect island retreat, this Sea Pines gem delivers luxury, location, and lifestyle. Make 2372 Racquet Club your next Hilton Head escape or vacation home!Beach Club.

108 Lighthouse Road Unit 2372, Hilton Head Island

Listing courtesy of Hilton Head Luxury Homes, Inc. Selling Office: EXP Realty LLC.

board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.