Vacation Single Family Homes Real Estate | Vacation Single Family Homes for Sale

4 Beds ⋅ 4 Baths ⋅ 3,895 SqFt. ⋅ HILTONHEAD-511549 MLS

Filled with natural light and thoughtfully designed for comfortable living and entertaining, this exceptional home offers soaring ceilings, striking slate flooring, and an open, flowing floor plan. The spacious chef's kitchen seamlessly connects to the living room, dining area, family room, and breakfast nook, creating inviting spaces for gathering with family and friends. Offering four bedrooms and three-and-a-half baths, the home provides generous accommodations for both everyday living and hosting guests. Outside, enjoy a private fenced backyard complete with a sparkling pool, covered outdoor living area, and beautifully designed hardscape and mature landscaping-perfect for relaxing, grilling, and entertaining. Ideally located just moments from the iconic Harbour Town Golf Links, home of the annual RBC Heritage, this home places you in the heart of everything Sea Pines has to offer. Enjoy miles of leisure trails, pristine beaches, the Sea Pines Beach Club, Harbour Town Marina, South Beach Marina, Lawton Stables, world-class dining and shopping, and three championship golf courses. This is a rare opportunity to enjoy one of Hilton Head Island's most sought-after lifestyles.

75 Baynard Cove Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$879,000

3 Beds ⋅ 2 Baths ⋅ 1,882 SqFt. ⋅ HILTONHEAD-512297 MLS

Welcome to effortless Lowcountry living in the desirable Club Course neighborhood of world-famous Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home is light, bright, and move-in ready, offering the perfect combination of comfort, location, and island lifestyle. Thoughtful updates include new LVP flooring, fresh paint, updated primary bathroom, Trex decking, and a 2025 Trane HVAC system. The spacious back deck is ideal for outdoor dining, entertaining, or relaxing, while the large backyard offers space for a pool and for creating a private oasis. Located near the main gate of Sea Pines, this home provides quick and convenient access to everything Hilton Head Island has to offer while still enjoying the privacy and amenities of one of the island's most iconic communities. Sea Pines is home to three renowned public golf courses, miles of pristine beaches, numerous restaurants, Harbour Town, private owner and guest beach access at Tower Beach, and the exciting redevelopment of South Beach. From biking beneath moss-draped live oaks to golf, boating, dining, and days spent on the beach, the Sea Pines lifestyle is truly hard to beat. Hilton Head Island has also been recognized as the #1 Island in the U.S. for nine consecutive years, further reinforcing why so many people choose to call this special place home. Whether you're searching for a primary residence in Sea Pines, a Hilton Head Island second home, or a short-term rental investment / coastal getaway, this turnkey property is ready for its next owner. Move in, unpack, and start enjoying the Hilton Head Island lifestyle from day one. Schedule your in-person or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$25,000

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512232 MLS

Welcome to your coastal getaway! Own a deeded 2BR, 2BA quartershare at Brigantine Quarters in Shipyard. Enjoy 13 rotating weeks a year in this beautifully designed residence with vaulted ceilings and a large balcony with golf views. Prime weeks for 2027 include 4th of July and December 18th through New Year's Day 2028. This mini-resort includes tennis, pickleball, pools, a playground, and a private beach gate for BQ owners and guests. Maintenance fee covers appliances, furniture, maintenance upkeep, taxes, Shipyard fees, and more, ensuring a stress-free experience, ideal for personal use or rentals.

55 Barcelona Road Unit 242C, Hilton Head Island

Listing courtesy of The Homesfinder Realty Group.

$7,900,000

5 Beds ⋅ 6 Baths ⋅ 5,659 SqFt. ⋅ HILTONHEAD-511892 MLS

A rare offering for the discerning buyer seeking an exceptional property nestled within the prestigious May River Forest enclave of Palmetto Bluff. Privately situated on nearly two acres, the estate is surrounded by mature woodlands with tranquil views of protected wetlands and the renowned May River Golf Course. Designed as the personal residence of an award winning local architect, every element has been thoughtfully curated to deliver an unparalleled blend of innovation, craftsmanship, and timeless design. Encompassing over 5,600 heated square feet, the home is centered around effortless main-level living with an open-concept floor plan, soaring ceilings, expansive walls of glass, and seamless indoor-outdoor spaces designed for entertaining and everyday enjoyment. State-of-the-art systems and meticulously executed details define this one-of-a-kind retreat. Offering extraordinary privacy in one of Palmetto Bluff's most coveted neighborhoods, this is a truly rare opportunity to own a legacy home where every detail has been masterfully considered.

135 Mount Pelia Road, Bluffton

Listing courtesy of Corcoran HM Properties - Bluffton.

$799,000

6 Beds ⋅ 8 Baths ⋅ 4,407 SqFt. ⋅ HILTONHEAD-512129 MLS

Own one-eighth of this professionally managed, turnkey home by Pacaso. Bald Eagle sits on a quiet third-row lot on Hilton Head Island, just a short walk from the Atlantic through a private beachside community. The exterior has a covered front porch, classic columns and a shingled roofline that feels considered and unhurried against the island's natural landscape. Inside, the entry foyer has a custom curved staircase, ornate columns, coffered ceilings and light hardwood floors that run throughout the main level. The great room has box beam ceilings, a traditional fireplace with a modern tile surround and built-in storage, opening directly into the dining area with French doors to the backyard. The kitchen has dark stone countertops, a premium range hood, glass-front cabinetry, a quartz-topped island and a separate breakfast bar. The primary bedroom opens to the backyard patio and has a spa-caliber en suite bath with a freestanding soaking tub, tiled shower and dual vanities. Five additional bedrooms, each with private baths, and a bonus room with wet bar complete the layout across three floors connected by a four-stop elevator. The heated pool, overflowing hot tub and outdoor cooking area sit within mature landscaping that gives the backyard a private, enclosed quality. The beach is a short walk through the community's private beachside access. Harbour Town and its iconic lighthouse, the Quarterdeck's waterfront dining and the Sea Pines Resort's golf courses and trails are all within easy reach. Bald Eagle is professionally designed, appointed and managed by Pacaso. Owners arrive to find the home ready at every visit, with nothing left to coordinate before the stay begins.

8 Bald Eagle Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$7,050,000

5 Beds ⋅ 6 Baths ⋅ 5,278 SqFt. ⋅ HILTONHEAD-511871 MLS

Welcome to 34 Ruddy Turnstone - a classic custom-built oceanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$340,000

2 Beds ⋅ 2 Baths ⋅ 900 SqFt. ⋅ HILTONHEAD-512032 MLS

Investor friendly condo steps to the beach! Short term rental capable, completely renovated and new, fully furnished, with a lovely balcony outfitted with appealing deck chairs. HHBT Resort has it all! Walk or ride bikes to the beach, take a dip in the pools, fit in a gym workout, a match of Pickle ball or Tennis, play on the playground, eat at any of the restaurants within each, and so much more! Don't miss this beautiful opportunity that is priced to sell!

40 Folly Field Road Unit APT G21, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$1,795,000

3 Beds ⋅ 3 Baths ⋅ 2,590 SqFt. ⋅ HILTONHEAD-511308 MLS

Don't miss this beautifully maintained, newer-style 3-bedroom, 3-bath home in a highly desirable Sea Pines location. Tucked away on a quiet cul-de-sac and private street just minutes from Harbour Town, this home offers the perfect combination of comfort, updates, and Lowcountry charm. Step inside to find beautiful new hardwood floors, smooth painted ceilings, and a spacious great room with soaring ceilings, a fireplace, and peaceful lagoon views. The updated kitchen features stainless steel appliances, granite countertops, a stylish backsplash, and opens seamlessly to the main living spaces. Additional features include a separate dining room and a wine bar, making this home ideal for entertaining. The first-floor primary suite offers a relaxing retreat with a spacious walk-in closet, double vanity, and walk-in shower. With two HVAC systems, a two-car garage, and abundant extra storage, this home is as functional as it is beautiful. Located in the heart of Sea Pines, enjoy convenient access to Harbour Town, beaches, leisure trails, golf, tennis, pickleball, dining, shopping, and all the incredible amenities Sea Pines has to offer.

58 Planters Wood Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$3,895,000

4 Beds ⋅ 5 Baths ⋅ 4,479 SqFt. ⋅ HILTONHEAD-511923 MLS

Nestled within the prestigious May River Forest neighborhood, 18 High Hope Way is a timeless Lowcountry retreat where classic architecture, thoughtful craftsmanship, and sweeping golf course views come together in perfect harmony. Recently remodeled and freshly painted, this exceptional residence offers 4,479 square feet of beautifully appointed living space overlooking the 9th fairway, complete with the rare inclusion of a coveted Tier 1 Golf Membership. Designed by Dawson & Wissmach and built by Clark Custom Builders, the home's enduring appeal begins with welcoming wraparound porches, mature native landscaping, and a handsome blend of brick, tabby, wood siding, and metal roofing. Inside, rich textures and abundant natural light create warm, inviting spaces throughout. A brick-accented foyer leads to soaring cathedral ceilings, exposed brick accents, a gas fireplace, and expansive French doors that seamlessly connect the indoors with multiple outdoor living spaces. The thoughtfully designed kitchen is both elegant and functional, featuring a farmhouse sink, six-burner gas range with custom hood, paneled refrigerator and dishwasher, generous center island, and a convenient pass-through to the dining room. A wet bar with an ice maker and beverage refrigerator, along with a temperature-controlled wine cellar, creates the perfect setting for effortless entertaining. The private primary suite serves as a peaceful retreat with its own office or sitting area, French doors opening to the covered porch, dual walk-in closets, and a spacious spa-inspired bath. Upstairs, a loft lined with custom bookshelves connects two ensuite guest bedrooms, while the carriage residence above the garage offers a kitchenette, living area, bedroom, and full bath-ideal for hosting family and friends. Outdoors, a screened porch with a fireplace overlooks the rolling fairways, providing an inviting space to relax in every season. Blending timeless Lowcountry architecture with modern updates and exceptional indoor-outdoor living, 18 High Hope Way offers an extraordinary opportunity to experience the beauty, comfort, and lifestyle of May River Forest.

18 High Hope Way, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$1,895,000

3 Beds ⋅ 4 Baths ⋅ 1,770 SqFt. ⋅ HILTONHEAD-511715 MLS

A refined expression of Lowcountry luxury, this exceptional Moreland cottage embodies the effortless elegance and timeless appeal that define life in Palmetto Bluff. Eligible for short-term rentals, the residence presents a rare opportunity to enjoy an extraordinary lifestyle while offering exceptional investment potential. Designed with impeccable attention to detail, the home's light-filled interior unfolds through an inviting open floor plan where sophisticated finishes and thoughtful craftsmanship create an atmosphere of understated luxury. The gourmet kitchen serves as the centerpiece of the home, appointed with premier Wolf and Sub-Zero appliances, custom cabinetry, and beautifully curated spaces for both intimate gatherings and grand entertaining.Seamlessly extending the living experience outdoors, the private patio is anchored by an Isokern fireplace, offering a warm and inviting retreat for evening cocktails, al fresco dining, and year-round enjoyment beneath the Lowcountry sky.Three beautifully appointed en-suite bedrooms, along with a stylish powder room, provide exceptional comfort and privacy for family and guests alike. Perfectly positioned just moments from Moreland's celebrated amenities, including acclaimed dining, resort-style recreation, and miles of scenic trails, this remarkable cottage captures the essence of luxury living in one of Palmetto Bluff's most sought-after neighborhoods.

752 Old Moreland Road, Bluffton

Listing courtesy of Charter One Realty.

$1,500,000

5 Beds ⋅ 5 Baths ⋅ 3,032 SqFt. ⋅ HILTONHEAD-510354 MLS

OPEN HOUSE this Saturday, 9/12 from 3PM-5PM. Welcome to 64 Sandcastle Court. Built in 2017, this is the newest home on Hilton Head Island within a short walk or bike ride to the beach currently priced below $1,600,000. In a market as competitive as this one, that distinction matters. Five bedrooms, four and a half baths, and four levels of living space comfortably accommodate 10 to 12 guests. There are two king primary suites, an open-concept main level with covered deck access and lagoon views, a middle level with its own covered deck and loft lounge, and a top-floor bunk room. Both rear decks can be screened, a meaningful upgrade for year-round enjoyment. The ground level is an experience unto itself: a large two-car garage, a covered outdoor living area beneath a beautiful wood-planked ceiling, a private heated pool, and a gas fire table with lava rock, its flames burning poolside. The rear and side yard can be fully fenced, providing additional flexibility for outdoor use. Folly Field Beach, one of Hilton Head Island's most beautiful beaches, is five minutes by bike and three minutes by golf cart. Shelter Cove is equally accessible by bike, with exceptional dining, shopping, and fireworks every Tuesday evening all summer long. Hilton Head Island has been named the Top Island in the United States by Condé Nast Traveler for nine consecutive years, most recently in 2025. Southern Living named it the South's Best Beach Town. Travel + Leisure included it in its World's Best Awards. With the Island's generational track record, guest demand is certainly not a trend. Even with professional management in place, the owners live nearby and keep a close and consistent watch on the property and everything in it. There are no surprises here for the new owner, and all existing guest reservations convey with the purchase. This home is offered fully furnished and turnkey, with rental projections of up to $129,000 annually. 64 Sandcastle Court may be the Investment with Benefits you've been searching for.

64 Sandcastle Court, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$1,749,500

3 Beds ⋅ 3 Baths ⋅ 2,440 SqFt. ⋅ HILTONHEAD-511596 MLS

OPEN HOUSE this Sunday, 9/13 from 1PM-3PM. Some things on Hilton Head Island are simply finite. A nearly .8-acre corner estate parcel in a gated oceanfront community is one of them. At 37 Kingston Road in Shipyard Plantation, that parcel is the foundation of something genuinely rare, and what sits on it makes the opportunity even more compelling. Those who know Hilton Head Island well know Shipyard. Tucked between Sea Pines and Palmetto Dunes, it is one of those communities that rewards the buyer who takes the time to know it. Direct beach access, Van Der Meer Tennis, three 9-hole golf courses, and the Sonesta Resort are all resident amenities within 800 acres of gated, security-patrolled Island living. And the location is exceptional: The Village at Wexford, Coligny Plaza, Coligny Beach, and some of the Island's most highly regarded restaurants, parks, and recreational offerings are all within minutes, by car or by bike. Among 1,655 total dwellings, only 255 are stand-alone homes. This is one of those homes, set on one of the largest private residential lots in any oceanfront gated community on the Island. This 3-bedroom, 2.5-bath home has been completely and beautifully reimagined. A top-to-bottom renovation includes all-new HVAC systems with new ductwork, a stunning new pool with a Pennsylvania flagstone deck that creates a private outdoor retreat worthy of the parcel it sits on, vaulted ceilings, skylights, thoughtful millwork, and designer finishes throughout. The kitchen features white shaker cabinetry, stone countertops, stainless-steel appliances, and a center island. The split floor plan provides ideal separation between the primary suite and guest rooms. The primary suite opens directly to the pool and features a marble walk-in shower and double vanity. A flexible bonus room serves equally well as a formal dining room, media room, study, sunroom, or hobby space. THE PARCEL ACCOMMODATES A FUTURE GUEST COTTAGE OR CASITA, A HOME EXPANSION, OR TWO ADDITIONAL GARAGE BAYS TO CREATE A FOUR-CAR GARAGE. For buyers thinking generationally, this is a rare canvas. 5 MINUTES BY BIKE TO THE SHIPYARD BEACH CLUB and one of the most beautiful beaches on the Island, where owners enjoy access to 420 private beach lockers, making every trip to the beach completely hassle-free. Offered furnished and available for immediate enjoyment. STR projections available upon request. *Owner is SCREA.

37 Kingston Road, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$925,000

2 Beds ⋅ 3 Baths ⋅ 2,032 SqFt. ⋅ HILTONHEAD-511564 MLS

Beautifully renovated 2BR/2.5BA home in the heart of Sea Pines offering exceptional privacy on a corner lot backing to protected open space and an adjacent unbuildable lot. From the charming courtyard entry with privacy gate to the expansive outdoor living space, every detail has been designed for comfortable everyday living and effortless entertaining. Open kitchen, dining and living areas, separate den with fireplace and built-ins, smooth ceilings, parquet floors, renovated kitchen and owner's bath, spacious guest suite, expansive deck with covered pergola, 2016 roof and 2023 Lennox HVAC, and parking for 3 cars. Located in one of Sea Pines' most welcoming neighborhoods where neighbors truly know one another. Located within the world-renowned Sea Pines Resort, owners enjoy easy access to miles of leisure trails, championship golf, beaches, tennis, pickleball, Harbour Town, South Beach Marina, restaurants, shopping, and countless outdoor activities. Whether you're searching for a primary residence, second home, or Lowcountry getaway, 33 Oak Court delivers privacy, comfort, and timeless appeal in one of Hilton Head Island's most sought-after communities.

33 Oak Court, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,350,000

5 Beds ⋅ 6 Baths ⋅ 4,702 SqFt. ⋅ HILTONHEAD-511693 MLS

Set on a beautifully positioned half-acre homesite, 24 Butterweed Road is a 4,702-square-foot home offering five bedrooms, five full baths, and one half bath across a thoughtfully designed main residence and private carriage house. Designed by acclaimed architect Court Atkins, built by CS Thomas Construction, and thoughtfully landscaped by Witmer Jones Keefer, this home embodies the timeless character and effortless livability that define Palmetto Bluff. Warm, welcoming, and exceptionally functional, the home is centered around expansive gathering spaces with hand crafted plaster walls where the kitchen, dining area, and great room flow seamlessly to a screened porch designed for effortless entertaining. Anchored by a fully equipped outdoor kitchen featuring both a built-in grill and an open fire Argentinian grill, this inviting space overlooks a private courtyard where a natural wood pizza oven and central fire pit creates a natural gathering place for evenings spent with family and friends beneath the Lowcountry sky. Just beyond the beautifully appointed kitchen, a well-equipped back kitchen enhances everyday living while concealing meal preparation from the main entertaining spaces. Adjacent to this service area, a temperature-controlled wine cellar offers the perfect setting to curate and display a treasured collection, bringing both function and sophistication to the heart of the home. The first-floor primary suite serves as a peaceful retreat, complemented by an additional guest suite on the main level. Upstairs, a spacious guest bedroom, comfortable lounge, and charming bunk room create an inviting haven for family and visitors, offering flexible accommodations that encourage extended stays and memorable gatherings. Above the detached two-car garage, a private office serves as a dedicated workspace, offering exceptional flexibility for remote work, creative pursuits, or future adaptation to suit a variety of lifestyle needs. Every detail reflects a thoughtful balance of refined craftsmanship and relaxed comfort, where generous porches, curated outdoor spaces, and seamless indoor-outdoor connections invite a lifestyle centered on gathering, entertaining, and enjoying the natural beauty that surrounds the home.

24 Butterweed Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$3,399,000

5 Beds ⋅ 6 Baths ⋅ 3,970 SqFt. ⋅ HILTONHEAD-511631 MLS

Tucked within Moreland Forest, Bramble Park is Palmetto Bluff's newest collection of just twelve homes, thoughtfully positioned along a peaceful greenspace and nature trail. Currently under construction and spanning 3,970 heated square feet, the Briar includes five bedrooms and five-and-a-half baths across the main home and carriage house. Dramatic gabled rooflines and clean lines give the home a distinctive presence, while vaulted ceilings and exposed beams bring a sense of scale and texture to the interiors. At the center of the home, the gathering room opens naturally to the screened porch and optional pool terrace beyond, creating a seamless relationship between indoor and outdoor living. Anchored by a substantial island, the kitchen offers plenty of room for everyday life and entertaining, with expansive windows bringing in natural light throughout the day. Covered porches and thoughtfully arranged living spaces encourage an easy flow from one room to the next, giving the home an openness that feels welcoming rather than oversized. The first-floor primary suite enjoys privacy from the rest of the home, while an additional bedroom on the main level offers flexibility for guests or everyday convenience. Upstairs, two bedrooms are connected by a loft that creates a comfortable space for reading, relaxing, or gathering. Above the two car garage, a carriage house with a fifth bedroom and separate loft provide a quiet setting for guests, creative pursuits, or a dedicated workspace removed from the main living areas. Confident in its architecture and generous in its proportions, The Briar balances contemporary influences with timeless materials and comfortable spaces. It is a home designed to age gracefully, with rooms that invite conversation, porches that naturally become gathering places, and a floor plan that feels as effortless as it is enduring.

130 Amaranth Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$2,599,000

4 Beds ⋅ 5 Baths ⋅ 3,295 SqFt. ⋅ HILTONHEAD-511621 MLS

Nestled within Bramble Park, Palmetto Bluff's newest collection of twelve homes tucked among the pines of Moreland Forest, The Dogwood takes its cues from the classic Lowcountry cottage. Currently under construction with 3,295 heated square feet, four bedrooms, four full baths, and one half bath, the home pairs timeless coastal architecture with a floor plan that feels welcoming from the moment you step onto the front porch. A detached two-car garage and carriage house complete the property, adding flexibility and a sense of privacy that is increasingly hard to find. At the center of the home, the gathering room and dining room are arranged around a spacious kitchen anchored by a substantial island and complemented by a separate back kitchen tucked discreetly out of view. Expansive windows and large openings allow natural light to move easily throughout the day, while the screened porch creates a natural extension of the living spaces and offers a quiet place to enjoy the changing seasons. With the option for a private pool, the backyard becomes its own retreat, equally suited for entertaining or slower afternoons spent at home. The primary suite occupies its own wing and enjoys separation from two guest bedrooms located on the opposite side of the home. Above the detached garage, a private fourth bedroom offers comfortable accommodations for guests while maintaining a sense of independence from the main residence. The result is a floor plan that feels both intimate and accommodating, with spaces that are thoughtfully arranged and easy to live in. Warm and familiar in all the right ways, The Dogwood embraces the enduring qualities that have always defined Southern homes: welcoming porches, rooms filled with light, and spaces that encourage people to gather and stay awhile. Rooted in tradition yet designed for modern life, it is a home that feels comfortable from the very beginning and timeless for years to come.

15 Inkberry Street, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$2,699,000

4 Beds ⋅ 5 Baths ⋅ 3,018 SqFt. ⋅ HILTONHEAD-511620 MLS

Tucked within Moreland Forest, Bramble Park is Palmetto Bluff's newest collection of just twelve homes, thoughtfully positioned along a peaceful greenspace and nature trail. Currently under construction, the Berryhill introduces a gracious take on Lowcountry living, with 3,018 heated square feet, four bedrooms, and four-and-a-half baths arranged around a private motor court framed by a detached garage and an optional golf cart barn. From the front porch to the screened porch stretching across the rear of the home, the floor plan is designed to invite people in. The central gathering room serves as the heart of the residence, with soaring ceilings and expansive windows bringing warmth and natural light to the interiors. Large openings connect the living spaces to the porch and backyard beyond, where an optional pool creates an ideal setting for afternoons with grandchildren, impromptu dinners with neighbors, or weekends spent with old friends. The kitchen is anchored by a substantial island made for conversation, while a separate back kitchen and walk-in pantry provide space for prep, storage, and the practical side of entertaining. Tucked away from the main living areas, the primary suite offers dual walk-in closets and a spacious bath, creating a quiet retreat within the home. Three additional guest suites are thoughtfully positioned to provide comfort and privacy for family and visitors alike. Balanced in its proportions and generous without feeling oversized, The Berryhill captures the qualities that never go out of style: rooms filled with light, porches that are meant to be lived on, and spaces that bring people together naturally. It's a home that feels established from the start and one that will only grow more meaningful with time.

23 Inkberry Street, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$5,900,000

7 Beds ⋅ 8 Baths ⋅ 5,203 SqFt. ⋅ HILTONHEAD-511606 MLS

Properties of this caliber are increasingly difficult to find in Sea Pines. 7 Bedroom/6.5 Baths PLUS Pool Bath, 2022 construction, designer furnished and just a 3-minute walk to the beach. Set on an oversized nearly 1/3-acre 3rd row homesite, this is the rare combination discerning buyers wait years to find. Custom construction and incredibly designed for effortless coastal living, the home showcases sophisticated finishes, soaring ceilings, a gourmet kitchen with a separate prep kitchen, and seamless indoor-outdoor living centered around a covered porch with an outdoor fireplace, summer kitchen, heated pool, and spa. Seven beautifully appointed bedrooms-including a first-floor primary suite and four ensuite guest suites-provide exceptional comfort and privacy, while multiple gathering spaces make the home ideal for entertaining family and friends. Combining exceptional quality, an oversized homesite, beach proximity, and one of Sea Pines' most desirable locations, this is a true legacy property offering the very best of coastal living. Current rental projections of approximately $349,000 annually.

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$3,199,000

5 Beds ⋅ 6 Baths ⋅ 4,170 SqFt. ⋅ HILTONHEAD-511598 MLS

Nestled within Bramble Park, Palmetto Bluff's newest collection of twelve homes tucked among the pines of Moreland Forest, The Larkspur draws inspiration from the classic Southern farmhouse. Currently under construction with 4,170 heated square feet, four bedrooms, five full baths, and one half bath, the home combines timeless architecture with spaces designed to accommodate both everyday living and a full house of family and friends. A detached garage and carriage house add privacy and flexibility, creating a property that lives with both comfort and ease. From the front porch to the screened porch stretching across the rear of the home, The Larkspur is centered around gathering. The spacious gathering room opens naturally to the porch beyond, creating a connection to the outdoors that feels effortless and inviting. Anchored by a generous island, the kitchen is designed to be the backdrop for everything from morning coffee to long dinners that linger late into the evening. An optional pool and garden courtyard further extend the living spaces, offering a setting that feels tucked away and quietly private. The first-floor primary suite occupies its own wing of the home, creating welcome separation from the guest accommodations above. Upstairs, three bedrooms are joined by a loft that offers additional living space, while the detached carriage house provides a fifth bedroom and a separate loft, making it equally suited for guests, a studio, or a quiet place to work. There is something familiar about The Larkspur. Its proportions are generous, its rooms are filled with light, and its architecture recalls the kind of Southern homes that never go out of style. Designed to evolve naturally over time, it is a home that feels established from the very beginning and one that only grows more meaningful with each passing season.

134 Amaranth Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$14,000,000

7 Beds ⋅ 11 Baths ⋅ 9,128 SqFt. ⋅ HILTONHEAD-511586 MLS

8 Anson Park Road East is an estate that simply leaves an impression. Set on nearly an acre in Palmetto Bluff's highly sought-after May River Forest, this extraordinary property was created by assembling two premier homesites, capturing sweeping views across the 10th fairway to the May River with spectacular sunrise vistas beyond. The result is over 7,500 square feet in the main residence complemented by a beautifully positioned 1,400 square-foot guest house that provides exceptional privacy for family and friends. In total, more than 9,000 square feet of refined living space unfolds across the property, where seven beautifully appointed bedrooms transform this remarkable estate into a true home. The estate was designed for both grand entertaining and intimate everyday living, a balance that is exceedingly evident throughout. Every inch of this property reflects the collaboration of exceptional craftsmen, an elite architectural and design team, and owners whose uncompromising vision ensured every detail was thoughtfully executed. All seven bedrooms feature bespoke en suite baths, while the kitchen transcends what is typically considered custom. A curated butler's pantry, lacquered wet bar with a full-height Sub-Zero wine cabinet, custom electronic draperies, four powder rooms, a wrapping room, three laundry facilities, oversized three car garage, his and her studies, soaring ceilings precisely where they belong, and dressing rooms that rival the finest luxury boutiques are just a glimpse of what awaits. Outside, a heated pool and spa anchor the home's outdoor living spaces, offering a natural extension of the interiors. Covered screened porches and open-air gathering areas are positioned to take full advantage of the views and setting, creating an easy flow for both quiet mornings and evenings meant for entertaining. 8 Anson Park Road East is located nearly adjacent to the May River Golf Club, tucked just inside the private security gate to the highly sought-after May River Forest enclave within Palmetto Bluff. The location is an extremely short golf cart ride to Wilson Village, Palmetto Bluff's original and storied village with world-class dining, boat excursions and dockage options, as well as the historic Wilson hunting lodge ruins; one of the most picturesque and beloved areas of the community. The location is idyllic, the home is of the finest quality, the views are beyond exceptional, and the lifestyle is unparalleled.

8 Anson Park E Road, Bluffton

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$1,645,000

5 Beds ⋅ 6 Baths ⋅ 4,165 SqFt. ⋅ HILTONHEAD-511552 MLS

Welcome to 90 Sandcastle Court, a spacious, beautifully appointed beach home in the gated Sandcastles by the Sea community. One of the larger homes in the neighborhood, this fully furnished, turnkey property offers five bedrooms, four full baths, two half baths, and elevator access to every level. The open-concept main living area is designed for gathering and entertaining, with a gourmet kitchen featuring granite countertops, GE Monogram appliances, a gas range, generous dining space, and an inviting living area. The lower level provides flexible recreation and additional living space with direct access to the private pool, hot tub, patio, and outdoor entertaining areas. Additional highlights include a large deck, low-maintenance artificial turf lawn, EV charging outlet, and multiple indoor and outdoor spaces for relaxing with family and guests. Ideally located just a short walk from the beach and close to Hilton Head Island's restaurants, shopping, golf, and attractions. Offered fully furnished with approximately $112,000 in gross rental revenue already booked for 2026, this exceptional property is ready to enjoy as a primary residence, vacation home, or income-producing short-term rental.

90 Sandcastle Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$815,000

3 Beds ⋅ 2 Baths ⋅ 928 SqFt. ⋅ HILTONHEAD-511473 MLS

Experience the charm of coastal living at 45 Night Heron, a beautifully positioned Sea Pines beach cottage just a five-minute stroll to Hilton Head Island's renowned beaches. This light-filled 3-bedroom, 2-bath retreat offers an open floor plan with soaring vaulted ceilings, creating an inviting space for gathering and relaxing. Ample enclosed storage beneath the home provides room for beach gear, bicycles, and more. Night Heron has its own private community pool. Harbour Town, South Beach, Sea Pines Beach Club, & the Plantation Golf Club are just moments away by way of 17 miles of picturesque leisure trails. Located near the Ocean Gate for easy island access and only minutes from the shopping, dining, and entertainment of Coligny Plaza, this property is perfectly suited as a primary residence, vacation home, or high-performing rental investment.

45 Night Heron Lane, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$2,499,000

4 Beds ⋅ 4 Baths ⋅ 2,982 SqFt. ⋅ HILTONHEAD-510784 MLS

Welcome to this 4 bedroom Sea Pines getaway! Lagoon and majestic live oaks in the backyard with private pool, gazebo and beautiful guest cottage. This updated single-level home offers the relaxed coastal lifestyle that makes Sea Pines one of Hilton Head Island's most sought-after destinations. Thoughtfully renovated and offered beautifully furnished, the home blends timeless Lowcountry charm with modern updates, making it ready to enjoy from day one.Inside, the open-concept floor plan is designed for gathering. The updated kitchen flows seamlessly into a bright and inviting family room with custom built-ins and a convenient desk nook for remote work or vacation planning. New flooring, updated lighting, and stylish finishes create a fresh, welcoming atmosphere throughout.The main house features three spacious bedrooms, while a separate guest cottage provides additional space for extended family, friends, or vacation guests. The flexible layout is ideal for second-home owners looking to maximize both enjoyment and rental potential.Step outside and discover the true magic of this property. A private Savannah brick courtyard surrounds the sparkling pool, creating an intimate outdoor retreat perfect for entertaining, relaxing, and making memories. Beyond the pool, a picturesque lagoon meanders through the backyard beneath a canopy of live oaks, providing a beautiful natural backdrop filled with Lowcountry wildlife and year-round scenery. A charming waterside gazebo offers the perfect spot for morning coffee, afternoon reading, or evening cocktails as the sun filters through the trees.Located in the heart of Sea Pines, owners and guests enjoy easy access to beaches, championship golf, miles of leisure trails, Harbour Town, South Beach Marina, shopping, dining, and all the amenities that have made Hilton Head Island a premier vacation destination for generations.Whether you're searching for a family retreat, a second home, or an investment property with proven vacation rental appeal, this exceptional Sea Pines residence delivers the best of island living.

37 Woodbine Place, Hilton Head Island

Listing courtesy of Hilton Head Properties.

$4,195,000

5 Beds ⋅ 6 Baths ⋅ 3,828 SqFt. ⋅ HILTONHEAD-511419 MLS

Gracefully positioned on a half-acre homesite overlooking one of River Road's picturesque neighborhood parks, 159 Red Ochre Road is a timeless Lowcountry retreat where thoughtful architecture, exceptional craftsmanship, and an unparalleled setting come together. Designed by Residential Concepts Design Group, built by JParker Homes in 2023, and complemented by the landscape architecture of Lowcountry Tide Design, the residence embraces the beauty of its surroundings with inviting porches, generous living spaces, and a seamless connection to the outdoors. Offering 3,828 heated square feet, the home features five bedrooms, four full baths, and one half bath thoughtfully arranged to provide both privacy and flexibility. The main residence centers around an expansive great room and chef's kitchen that flow effortlessly to a screened porch, creating ideal spaces for entertaining or relaxed everyday living. A private first-floor primary suite offers a peaceful retreat, while two guest bedrooms, an upper-level loft and study, and a spacious bonus bunk room above the garage provide comfortable accommodations for family and guests alike. A detached guest cottage with its own living room, loft, and private entrance creates an inviting space for extended family, visiting friends, or multigenerational living, ensuring every guest enjoys both independence and connection. Just beyond the front door, the home's exceptional location enhances the Palmetto Bluff lifestyle. The adjacent neighborhood park serves as an extension of the property, while a scenic walking path winds through the greenspace to a shared community dock, inviting mornings on the water, afternoon kayak excursions, or quiet evenings taking in the beauty of the surrounding Lowcountry landscape. Located within River Road, one of Palmetto Bluff's most sought-after neighborhoods, residents enjoy immediate access to miles of nature trails, parks, inland waterways, and the community's celebrated collection of dining, golf, recreation, and wellness amenities. Blending timeless design with modern comfort in an extraordinary setting, 159 Red Ochre Road presents a rare opportunity to experience the very best of life at Palmetto Bluff.

159 Red Ochre Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$2,100,000

4 Beds ⋅ 4 Baths ⋅ 3,531 SqFt. ⋅ HILTONHEAD-511413 MLS

Located in the heart of Harbour Town within Sea Pines, this beautifully appointed home offers the perfect blend of luxury, comfort and coastal charm. Enjoy easy access to iconic Harbour Town Yacht Basin, Lighthouse, shops, waterfront dining, renowned golf, miles of leisure trails and a short drive or shuttle to magnificent Hilton Head beaches. The home features 4 bedrooms and 4 bathrooms with expansive deck and pool. Ideal for entertaining, unwinding from a day at the beach or golf course. Whether you're seeking a full-time residence, vacation retreat or an investment property, this exceptional home captures the very best of the Sea Pines lifestyle.

8 Windjammer Court, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.