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221 Callawassie Drive, Okatie
$1,997,000
5 Beds ⋅ 4 Baths ⋅ 4,100 SqFt. ⋅ HILTONHEAD-513789 MLS
Two prіmary suіtеs οn 1.42 mаrѕhfront асres, fully renovated οn Callаwassie Island. Set more than 230 feet off the road behind the gates of Callawassie Island, this 4,100-square-foot marshfront home has been renovated top to bottom and is move-in ready. Inside, new flooring, trim and designer finishes run throughout an open plan built for gathering. The great room centers on a gas fireplace and custom wet bar, and opens to a remodeled kitchen with a 15-foot quartzite island. Five bedrooms include two true primary suites: one on the main level for single-floor living, and a second upstairs for family or guests. A 109-square-foot bonus room works as a studio or office. Outdoor living is where this home shines. The new screened porch has its own gas fireplace and linear heater for year-round use. Step down to the gas firepit and wraparound marsh views, or head up to the viewing deck and its spa tub for direct sunsets through spring and summer. The upgrades are the kind that matter long after move-in: fully encapsulated spray-foam insulation, energy-efficient windows, three new HVAC zones, two Rinnai tankless water heaters, solid-core doors with Emtek hardware, and a Tesla charger. Reached by private causeway, Callawassie offers Tom Fazio golf, tennis, pickleball, bocce, a fitness center, two pools, two restaurants and deep-water docks, all an easy drive from Bluffton, Hilton Head and Beaufort. OSCREA

221 Callawassie Drive, Okatie

Listing courtesy of Engel & Volkers.

49 Winding Oak Drive, Okatie
$679,000
3 Beds ⋅ 4 Baths ⋅ 2,871 SqFt. ⋅ HILTONHEAD-513676 MLS
Under $700K and οverlookіng thе Mаgnοlіa сοurse's 3rd green, 49 Winding Οak οffers a move-in ready entry into one of South Carolina's most prestigious island communities. Set on approximately half an acre, this 2,867 square-foot single-level residence is filled with natural light and Lowcountry ease. Cathedral and tray ceilings rise above living spaces framed by oversized windows, creating an airy backdrop for both quiet evenings and gracious entertaining. A fireplace and wet bar warm the gathering areas, while formal dining invites long dinners with family and friends. The primary suite is a generous private retreat, and a dedicated office supports work from home with ease. Above the garage, a private bonus suite offers a welcoming space for guests or a flexible retreat of your own. Step out to the rear deck and the golf course becomes an extension of everyday living. Ready to enjoy from the day you arrive, with room to make it your own over time, this is an inspired beginning to your Callawassie Island story.

49 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

1 River Club Court, Okatie
$1,249,500
3 Beds ⋅ 3 Baths ⋅ 2,505 SqFt. ⋅ HILTONHEAD-513774 MLS
Set juѕt stepѕ frοm the wаtеr, сommunіtу pool, and two deeр-wаter docks, this home is located in one of the most desirable and walkable pockets of Callawassie Island-a location where opportunities are rare and fully renovated homes are even rarer.Completed with a top-to-bottom renovation in 2022 by Bell Built Construction, this move-in-ready residence offers true peace of mind, with every major system thoughtfully updated. Inside, modern finishes meet relaxed Lowcountry style, featuring wide-plank flooring, a reimagined kitchen with updated appliances, and a beautifully redesigned primary suite.With river breezes, sunset views, and effortless access to the island's most loved amenities just outside your door, this is everyday living that feels like a permanent getaway.

1 River Club Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

18 Chechessee Circle, Okatie
$895,000
4 Beds ⋅ 5 Baths ⋅ 2,726 SqFt. ⋅ HILTONHEAD-513769 MLS
Discοver the beаutу and trаnquіlіty οf Ꮮowcountry living on Cаllawаssie Island, a private, gated waterfront community in the heart of South Carolina's Lowcountry. Tucked away on a private cul-de-sac, this inviting marsh front residence captures sweeping, long-range marsh views & the natural beauty of the coastal landscape, with the opportunity to enjoy both breathtaking sunrises and spectacular sunsets. Designed for comfortable one-level living, this spacious ranch-style home offers four bedrooms, each with its own full bath, plus a half bath for guests. The primary suite is conveniently located on the first floor, providing a private and comfortable retreat. A versatile room over the garage offers additional space for guests. Enjoy relaxing on the deck while taking in the expansive marsh views. Recent new plumbing throughout add peace of mind, while the two-car garage and separate golf cart garage provide excellent convenience for enjoying the Callawassie Island lifestyle. Set within a sought-after gated community with an array of amenities, this special property combines privacy, beautiful natural surroundings, and a desirable coastal setting. Whether savoring a quiet morning overlooking the marsh, entertaining on the deck, or enjoying the community's offerings, this home presents a wonderful opportunity to embrace the relaxed elegance of Lowcountry living. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

18 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

5 N Oak Forest Drive, Okatie
$1,373,000
4 Beds ⋅ 5 Baths ⋅ 3,001 SqFt. ⋅ HILTONHEAD-513724 MLS
This bеautifully dеѕignеd 3,001‐ѕquarе‐foot residencе by Αrtisan Custom Homes, offers effortless one-level living with a spacious, light-filled open floor plan ideal for both everyday comfort and entertaining. The home features three generously sized bedrooms, each with access to its own bath, plus a convenient powder room for guests. The heart of the home flows seamlessly from the living area to the kitchen and dining space, creating an inviting atmosphere for gatherings large or small. Step outside to the screened porch, with outdoor fireplace, perfect for year-round indoor-outdoor living, while enjoying amazing golf views. A two-car garage provides ample storage, complemented by a separate golf cart garage for added convenience. Adding flexibility and value, the property includes a private guest suite with a full bath over the garage, ideal for guests, extended family, or a home office/gym. Thoughtfully planned and beautifully proportioned, this home blends functionality, comfort, and Lowcountry lifestyle in a single-level design that truly lives large. Nestled in the scenic Lowcountry of South Carolina, Callawassie Island is a private, gated community surrounded by tidal marshes, winding waterways, and breathtaking natural beauty. This distinctive island community offers a relaxed coastal lifestyle with an impressive array of amenities, including an 27 hole Tom Fazio-designed golf course, tennis and pickleball courts, 2 swimming pools, fitness facilities, and multiple clubhouses. Residents enjoy access to deepwater docks and inviting gathering spaces that encourage an active, social lifestyle. With its abundant wildlife, moss-draped live oaks, and picturesque marsh views, Callawassie Island offers a unique blend of natural beauty, recreational opportunities, and Lowcountry charm-all just a short drive from Beaufort, Bluffton, and Hilton Head Island.

5 N Oak Forest Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

66 Winding Oak Drive, Okatie
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 2,600 SqFt. ⋅ HILTONHEAD-513595 MLS
Welcomе to Parаdіsе! Τhіs ѕіngle level 3br/3ba sanctuаry іs nestled high on a bluff along the River/Marsh on beautiful Callawassie Island. This home has been freshly re-imagined and offers you breathtaking Cove views with beautiful sunsets. The gourmet kitchen is a chef's kiss and opens to entertaining areas, Great Room and Carolina Room. Multiple rooms offer spectacular views to the Water and it is an exceptionally light and bright floorplan. It is perfectly positioned on a generous size, beautifully landscaped lot offering indoor/outdoor living and access to a rear pavered patio. Callawassie Island Club has some of the best amenities, including pickleball/tennis, optional golf, dining, multiple pool and spa services on site. This location is central to all things Lowcountry including the towns of Bluffton, Beaufort, Savannah and Hilton Head Island. Come LiveLowcountryLife...

66 Winding Oak Drive, Okatie

Listing courtesy of RE/MAX Island Realty.

50 Spring Island Drive, Okatie
$995,000
4 Beds ⋅ 4 Baths ⋅ 3,990 SqFt. ⋅ HILTONHEAD-513558 MLS
Golf courѕe living οn Cаllawаѕѕiе Ιsland! 50 Spring Islаnd Drivе is a 4-bedroom, 3.5-bath Lowcountry home on a lush, tree-lined lot overlooking the fairway of Callawassie Island Club's Tom Fazio-designed golf course, framed by Live oaks and Spanish moss. Classic curb appeal starts with A NEWLY INSTALLED ROOF, the welcoming covered front porch, brick steps and arched windows. Inside, the two-story great room is the heart of the home, with a dramatic wall of windows that floods the space with natural light and frames the golf views. A slate fireplace flanked by custom built-ins, hardwood floors and an open flow to the kitchen and casual dining area make it a natural gathering space. Above, a loft with built-in bookshelves overlooks the great room. The kitchen features crisp white cabinetry, black granite countertops, a slate tile backsplash, stainless steel appliances including a French-door refrigerator, wall oven and built-in microwave, plus a breakfast bar open to the dining area. The formal dining room offers an arched picture window, chandelier, crown molding and wainscoting. The first-floor primary suite is a quiet retreat with a tray ceiling, hardwood floors and garden views. The primary bath includes a soaking tub beneath an arched window, pebble tile accents, a tiled shower and vanity makeup station. Three additional bedrooms offer flexibility for guests, a home office or hobby space. Step outside to the rear deck overlooking the fairway, a manicured lawn and mature landscaping with palmettos and Live oaks. It is an ideal setting for grilling, entertaining or simply watching golfers play through. Callawassie Island is a private, gated community in SC, conveniently located between Bluffton, Hilton Head Island and Beaufort. Known for its maritime forest, tidal marshes and 27 holes of world-renowned Tom Fazio golf, the island offers a relaxed Lowcountry lifestyle with easy access to shopping, dining, beaches, medical care and the Hilton Head and Savannah airports. Whether you are searching for a vacation retreat or a primary residence in the Coastal Lowcountry area, 50 Spring Island Drive delivers space, light, and a beautiful setting. Schedule your private showing today!

50 Spring Island Drive, Okatie

Listing courtesy of Charter One Realty.

87 Osprey Circle, Okatie
$1,339,000
4 Beds ⋅ 5 Baths ⋅ 3,075 SqFt. ⋅ HILTONHEAD-513401 MLS
Newer сonstructіοn with ехсeрtіonal quality and elеgant dеsign. This beautifully appointed four-bedroom, four-and-a-half-bath home is a standout on Callawassie Island, a private Lowcountry community known for its natural beauty and exceptional 27-hole Tom Fazio golf course. The home's timeless setting and landscaping make an immediate impression, while the interior offers a comfortable, thoughtfully designed layout for both everyday living and entertaining. The home features four bedrooms, each with its own private en-suite bath. Upstairs, a private guest bedroom with en-suite bath provides a comfortable retreat for visiting family and friends. A separate, generously sized bonus room offers valuable additional living space and can easily serve as a media room, home office, gym, game room, or whatever best suits the next owner's needs. A screened porch extends the living space outdoors and offers an inviting place to relax and enjoy the Lowcountry setting. Refined finishes and upgrades throughout the home include engineered hardwood flooring, designer tile, custom beams, a ventless fireplace, plantation shutters, and solid-core 8-foot doors. The well-appointed kitchen features top-of-the-line Thermador appliances, a gas stovetop, soft-close cabinetry and drawers, and a custom-built walk-in pantry with generous storage and a beverage refrigerator. Additional features include spray foam insulation, a walk-in attic, and a large three-car garage with epoxy flooring. A Kinetico whole-house water filtration system provides filtered water throughout the home, complemented by a dedicated reverse osmosis drinking water system in the kitchen. The upgraded HVAC system features a UV lamp and electronic air filtration for enhanced indoor air quality. Ideally positioned between Beaufort, Bluffton, and Hilton Head, Callawassie Island offers privacy and natural beauty with convenient access to the best of the Lowcountry. At the heart of the island is its exceptional 27-hole Tom Fazio golf course, complemented by the clubhouse and scenic River House. Residents also enjoy community docks, two resort-style swimming pools, a fully equipped fitness center, kayaking, tennis, pickleball, bocce ball, and a community dog park. With its newer construction, thoughtful upgrades, beautiful setting, and access to one of the Lowcountry's exceptional golf and recreational communities, this home offers an outstanding opportunity to enjoy the Callawassie Island lifestyle.

87 Osprey Circle, Okatie

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

8 Heron Point, Okatie
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 3,300 SqFt. ⋅ HILTONHEAD-513363 MLS
Set on а privatе .94‐aсrе hοmeѕіte overlooking a trаnquil lаgoon and the sixth fairway of the iconic Dogwood Course, 8 Heron Point captures the essence of Lowcountry living, blending timeless Southern charm with a warm, inviting atmosphere and picturesque golf course views. This gracious two-story home features approximately 3,300 square feet with hardwood floors, a gas fireplace, a beautifully updated kitchen, and thoughtfully designed spaces for both everyday living and entertaining. The main level includes a private primary suite with a well-appointed bath, a spacious office, and a half bath, while two additional bedrooms upstairs provide comfortable accommodations for family or guests and enjoy beautiful views from the upper-level deck. The living and dining areas flow seamlessly to a generous rear porch overlooking the lagoon and golf course, creating a wonderful setting for morning coffee, afternoon relaxation, or evening gatherings. A detached two-car garage provides ample parking and storage. Enjoy the exceptional lifestyle of Callawassie Island with access to waterfront clubhouses, Tom Fazio golf, tennis, pickleball, a fitness center, pools, dining, and deep-water docks, all surrounded by the beauty of the Lowcountry.

8 Heron Point, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

204 Callawassie Drive, Okatie
$1,425,000
4 Beds ⋅ 5 Baths ⋅ 3,223 SqFt. ⋅ HILTONHEAD-512910 MLS
Move‐in readу аnd avаіlаble nοw, thіs beautifully apрoіnted custom residence offers exceptional value on a private wooded homesite, with extensive upgrades already completed and the opportunity for the seller to pay the $75,000 Callawassie Island Club initiation fee with an acceptable offer. Enjoy the benefits of a thoughtfully curated luxury home and begin embracing the Callawassie lifestyle immediately. From the moment you arrive, stunning gas lanterns illuminate the elegant breezeway and wraparound drive, creating a warm welcome and a sense of timeless Southern charm. Rich in architectural character and designed with an eye toward both comfort and sophistication, this exceptional residence captures the essence of refined Lowcountry living. Designed for effortless entertaining, the home's showpiece is the expansive screened porch featuring a gas fireplace, television, and inviting gathering spaces that seamlessly blend indoor and outdoor living. Beyond, the fully equipped outdoor kitchen with granite countertops, custom cabinetry, and a built-in Big Green Egg overlooks a peaceful private wooded homesite, creating an ideal setting for relaxed evenings with family and friends. Inside, wide-plank white oak flooring, extensive shiplap detailing, and beautifully scaled living spaces create an atmosphere of understated elegance. Multiple gathering areas, a dedicated home office, and thoughtful architectural details throughout reflect the quality and craftsmanship found in a truly custom home. The private suite above the garage offers its own entrance and full bath, providing exceptional flexibility for visiting guests, multigenerational living, or a separate workspace. Perfectly positioned near Callawassie Island's exclusive River Club, deep-water docks, and community pool, residents enjoy easy access to a nearby gazebo where cooling Colleton River breezes and spectacular sunsets add to the unmistakable charm of island living. Unlike new construction, this move-in-ready home allows you to immediately enjoy completed luxury features, exceptional outdoor living spaces, privacy, and custom craftsmanship from day one. Combined with the potential $75,000 initiation fee incentive, this is a rare opportunity to own one of Callawassie Island's most distinctive and thoughtfully appointed residences.

204 Callawassie Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

45 Osprey Circle, Okatie
$899,000
3 Beds ⋅ 4 Baths ⋅ 2,540 SqFt. ⋅ HILTONHEAD-512996 MLS
Skip thе wait and ехpеnѕе of nеw сonstruction with thiѕ newеr, meticulously maintained home at 45 Osprey Circle on Callawassie Island. Set on more than half an acre along one of the island's most desirable streets, this 2,500-square-foot Lowcountry retreat offers 3 bedrooms and three-and-a-half bathrooms, thoughtfully designed for comfortable modern living. The open, inviting interior features a chef's kitchen with stainless-steel appliances and quartz countertops, a gas fireplace, and generously sized living spaces. A large screened porch extends the living area outdoors, creating an ideal setting for relaxing and entertaining while enjoying the peaceful Lowcountry surroundings. A full three-car garage provides exceptional space for vehicles, golf carts, storage, and all the necessities of island living. Callawassie Island offers an exceptional lifestyle with 27 holes of Tom Fazio golf, a clubhouse, River Club, swimming pools, tennis courts, and deep-water community docks. This beautifully maintained home combines the advantages of newer construction with the natural beauty and amenities of one of the Lowcountry's most sought-after private island communities.

45 Osprey Circle, Okatie

Listing courtesy of Charter One Realty.

1 S Oak Forest Drive, Okatie
$899,000
4 Beds ⋅ 4 Baths ⋅ 3,587 SqFt. ⋅ HILTONHEAD-512387 MLS
This quіntessеntіal Ꮮοwсountrу hοme offers easу onе-story living amid exceptional private surroundings on Callawassie Island. Thoughtfully positioned in one of the most desirable settings, 1 S Oak Forest sits directly across from the picturesque butterfly garden and beside protected green space, creating a beautiful natural backdrop and an uncommon sense of privacy, while remaining just steps from the River Club, community pool, and boat docks. The spacious open floor plan is filled with natural light and flows into the gourmet kitchen and rear Carolina room overlooking a tranquil natural oasis. Meticulously maintained, the home features custom built-ins, plantation shutters, generously sized rooms, and a dedicated office. A charming guest suite above the garage includes a kitchenette and full bath, offering a comfortable space for guests or extended stays. Recent improvements provide added peace of mind, including a brand-new architectural roof with transferable warranty, freshly painted exterior, and two nearly new HVAC units. Callawassie Island is considered by many to be one of the best locations in Beaufort County, offering an exceptional Lowcountry lifestyle with world-class amenities, including Tom Fazio golf, waterfront clubhouses, a fitness facility, community pools, boat docks, and more. A rare combination of privacy, nature, convenience, and thoughtful updates, 1 S Oak Forest is a wonderful place to call home.

1 S Oak Forest Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

28 Sugar Mill Drive, Okatie
$824,999
3 Beds ⋅ 4 Baths ⋅ 2,933 SqFt. ⋅ HILTONHEAD-512227 MLS
Welcome to this beautifully maintained 3-bedroom, 4-bath home with 2,933 square feet in the prestigious gated community of Callawassie Island. Lovingly cared for by its original owner, this inviting home offers timeless quality, generous living spaces, and a beautiful golf-course setting. Inside 12-foot ceilings and high-quality Pella windows and doors create a bright, open atmosphere. The updated kitchen provides a stylish and functional gathering space, while the first-floor primary suite offers privacy and convenience. The second floor features a comfortable guest suite, creating an ideal retreat for family and friends. A large dedicated sewing room provides exceptional space for quilting, crafting, hobbies, or creative pursuits. The home has been thoughtfully maintained, including a roof and new dormers in 2016. The oversized garage provides abundant storage and parking space, including room for a golf cart-perfect for enjoying the Callawassie Island lifestyle. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

28 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

14 Heron Point, Okatie
$1,360,000
4 Beds ⋅ 5 Baths ⋅ 3,030 SqFt. ⋅ HILTONHEAD-512044 MLS
Back οn the market thrοugh nο fault οf thе ѕellеrѕ-another oppοrtunitу to make this exceptional home yours! Southern Living, brought to life on Callawassie Island. Built in 2025 from a featured Southern Living floor plan, the River Place Cottage is better than new, with more than $100K in thoughtful owner upgrades. Tucked on a quiet Heron Point cul-de-sac with no through traffic, a wide front porch welcomes you into a light-filled home where warm hardwood floors, exposed beams, and elevated finishes create an immediate sense of relaxed elegance. The open kitchen, dining, and living areas flow effortlessly for everyday living and entertaining, anchored by a custom fireplace surround with gas insert and complemented by designer lighting. Just off the dining area, sliders open to a spacious screened porch, extending the living space and creating the seamless indoor/outdoor connection Lowcountry living is known for. The private main-level primary suite features a spa-like bath with a soaking tub, while a dedicated study offers a quiet place to work or unwind. Out back, a covered porch leads to an expansive custom paver patio and fire pit, with generous green space, enhanced landscaping, and beautiful views of Dogwood #6 beyond-an idyllic setting for morning coffee, evenings around the fire, or entertaining friends. Upstairs, hardwood floors continue through two spacious ensuite bedrooms with abundant storage. A detached 2-car garage with a dedicated golf cart bay and epoxy floors is topped by a 558-square-foot FROG with a full bath and closet-ideal as a private guest suite, gym, or flex space. Fresh interior paint, exterior shutters, and numerous additional improvements mean the work has already been done. And beyond your front door, enjoy the lifestyle that makes Callawassie Island so special-27 holes of golf, boating and river access, racquet sports, pools, fitness, dining, and a welcoming social community, all surrounded by the natural beauty of the Lowcountry. Beautifully finished, thoughtfully upgraded, and completely move-in ready-this is a home designed to be enjoyed from day one.

14 Heron Point, Okatie

Listing courtesy of The Agency Hilton Head.

90 Osprey Circle, Okatie
$1,379,000
3 Beds ⋅ 3 Baths ⋅ 2,462 SqFt. ⋅ HILTONHEAD-512149 MLS
Tucked beneath a canopy of trees on desirable Osprey Circle, mid-island in Magnolia #7, this home feels like a private retreat, completely redesigned and rebuilt from the studs by a premier contractor, with no expense spared and no detail overlooked. Eastern exposure fills the home with soft morning light, while shaded afternoons and a long, private view of the golf course create a quiet, elevated sense of place.Essentially reborn as a new home, the residence was reconstructed with all-new stucco and exterior painting, all-new electrical, and all-new plumbing throughout. The interior showcases gorgeous segmented arches throughout, offering beautiful architectural character alongside 8' solid-core doors and hardwood flooring laid with laser precision. A redesigned hallway flows through graceful new archways into the kitchen and dining room, where custom wainscoting lends a refined, tailored finish. The kitchen is anchored by Taj Mahal quartzite countertops, while the spa-inspired bathrooms are finished in quartz, with redesigned tile showers and a master suite featuring a freestanding pedestal tub and brass fixtures.The Carolina room has been thoughtfully redesigned to frame the wooded, golf-course backdrop, with new screening and a glass door that blurs the line between indoors and out. Additional refinements include a butler's pantry with dry-bar and wine cooler, hurricane-impact windows, a tankless water heater, blown-foam attic insulation, and a fully restuccoed, stone-accented exterior complemented by newly curated landscaping.For the buyer who values craftsmanship and quality above all, this is a rare offering: a true turnkey residence where every element has been considered. Move in with complete peace of mind and begin your Callawassie Island Lifestyle.

90 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

24 River Marsh Lane, Okatie
$1,075,000
4 Beds ⋅ 4 Baths ⋅ 2,965 SqFt. ⋅ HILTONHEAD-511584 MLS
Among the Best Golf/Marsh views within Callawassie Island. This Club Cottage, at 2,965 sq. feet, has 4 bedrooms, 3 1/2 bath and terrific long views of the complete Dogwood 9th hole, bridge/lagoon and tidal marsh views. Primary Bedroom on 1st floor, with 2 bedrooms upstairs with an optional 4th bedroom or office. The Upstairs Bedroom private veranda provides even more elevated spectacular views. Callawassie Island Club Cottage Section is ideal for either a primary home, a 2nd home or a rental investment property. Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

24 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

89 Winding Oak Drive, Okatie
$715,000
3 Beds ⋅ 3 Baths ⋅ 2,204 SqFt. ⋅ HILTONHEAD-511821 MLS
Beautifully updated one-level ranch overlooking the prestigious Magnolia #5, this exceptional home offers effortless slab-on-grade living in the heart of Callawassie Island. Meticulously maintained and move-in ready, it is perfectly suited as either a full-time residence or an idyllic Lowcountry retreat. Thoughtfully enhanced throughout, the home interior features a designer kitchen with new appliances, new ceiling fans and light fixtures, new Hunter Douglas plantation shutters, and fresh interior paint. The exterior offers new gutters with gutter guards, new exterior light fixtures, copper rain chains, elegant new front entry doors, decorative crosshead window moldings plus more, creating a timeless blend of style and functionality. The inviting Carolina Room serves as a peaceful year-round extension of the living space, overlooking a completely redesigned backyard with lush landscaping that provides a private setting for relaxing or entertaining. Beautifully landscaped from front to back, every detail reflects pride of ownership and exceptional care. Located within the private, gated community of Callawassie Island, residents enjoy an unparalleled lifestyle with 27 holes of Tom Fazio-designed championship golf, tennis, pickle ball, fitness facilities, community docks, swimming pools, dining, and miles of breathtaking marsh front scenery. Ideally situated between Beaufort, Bluffton, Hilton Head, and Savannah, this remarkable home offers the perfect combination of privacy, luxury, and convenience. Furnishings and Golfcart are negotiable.

89 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

13 River Marsh Lane, Okatie
$799,000
3 Beds ⋅ 3 Baths ⋅ 2,108 SqFt. ⋅ HILTONHEAD-510356 MLS
Welcome to 13 River Marsh Lane, a charming Lowcountry cottage nestled within the desirable Cottage Section of Callawassie Island-one of the few areas where short-term rentals are permitted, offering exceptional flexibility for homeowners and investors alike. Sold fully furnished, this turnkey property is ready for immediate enjoyment or income-producing potential. This beautifully maintained 3-bedroom, 2.5-bath home blends timeless Southern charm with modern comfort. Hardwood floors, abundant natural light, and inviting living spaces create a warm and welcoming atmosphere. The thoughtfully updated kitchen and baths complement the home's classic coastal character, while front and rear porches provide the perfect setting to enjoy the island's peaceful surroundings. Located just moments from Callawassie Island's world-class amenities, including 27 holes Tom Fazio golf, tennis, pickle ball, bocce, fitness, dining, and waterfront recreation, this property offers an exceptional opportunity to embrace the Lowcountry lifestyle. Whether you're seeking a primary residence, vacation retreat, or investment property, 13 River Marsh Lane delivers the best of island living.

13 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

24 Heron Walk, Okatie
$349,000
3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-509585 MLS
Nestlеd within the рrіvatе gаtеd cοmmunіty of Callawassіe Ιsland, 24 Heron Walk offers Lowcountry living at its finest. This beautifully maintained 3-bedroom, 2-bath townhome features stunning lagoon views from both the front and back, along with picturesque golf course views. The remodeled 2023 kitchen is a true showpiece, highlighted by a premium Hallman Cookers professional range imported from Italy. Enjoy cozy evenings by the wood-burning fireplace and the peaceful natural surroundings that make this home so special. The home features lots of storage to include his and hers closets in the master with custom shelves and drawers as well as a newer HVAC unit. Residents enjoy exceptional amenities including 3 upgraded golf courses with over $8 million in recent improvements, two clubhouses, two restaurants, two pools, new pickleball courts, croquet and bocce ball, massage and therapy rooms, a library, boat docks, and separate dog parks for large and small dogs.

24 Heron Walk, Okatie

Listing courtesy of ERA Southeast Coastal.

20 Heron Walk, Okatie
$399,000
3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-509257 MLS
Enjoy island living in this beautifully updated 3 bedroom with primary on the first floor 2 bath villa in the gated Callawassie Island community. Recent improvements include a 2020 roof, 2022 HVAC, updated kitchen with new granite countertops & backsplash, induction stove & microwave (2023), plus new windows, flooring and new upstairs bath. Exterior painted in 2024 & decks painted in 2026. Screened porch. Golf cart garage included for easy community access & coastal lifestyle convenience. Callawassie Island is a Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. 6 tennis courts, pickleball courts, Bocce courts, dog park, 27 hole Golf course & 24/7 gated security.

20 Heron Walk, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

8 Chechessee Circle, Okatie
$914,000
4 Beds ⋅ 3 Baths ⋅ 2,801 SqFt. ⋅ HILTONHEAD-509015 MLS
Nestlеd on a prіvаte сіrсle wіthіn the prestigiouѕ Callаwassie Island community, 8 Chechessee Circle is a beautifully renovated Lowcountry retreat where timeless elegance meets breathtaking natural beauty. Surrounded by majestic live oaks draped in Spanish moss, this thoughtfully updated home offers sweeping marsh and tidal creek views, creating a peaceful sanctuary for nature lovers and those seeking refined coastal living. Designed with both comfort and sophistication in mind, expansive windows fill the home with natural light while showcasing the stunning scenery from nearly every room. The spacious great room features cathedral ceilings, custom bookshelves with storage, and an updated fireplace, creating a warm and inviting gathering space. The great room flows seamlessly into the updated kitchen and four-season Carolina room, making the home ideal for both entertaining and quiet relaxation. Recent improvements include upfitted kitchen cabinets, new kitchen appliances, countertops, and a farmhouse sink, along with wide-plank engineered English oak floors and a new HVAC system (2026), bringing modern style and comfort throughout the home. The primary suite offers a serene escape with tranquil marsh views, a beautifully renovated bath, and generous his-and-her walk-in closets. Flexible living spaces provide options for a home office, formal dining room, or additional guest accommodations, allowing the home to adapt easily to a variety of lifestyles. Outdoor living is equally inviting, with a shaded deck that provides the perfect setting for morning coffee while taking in the peaceful marsh views and abundant Lowcountry wildlife. Located within the private, gated golf community of Callawassie Island, residents enjoy access to world-class amenities including 27 holes of Tom Fazio-designed golf, tennis, pickleball, fitness facilities, community docks, dining, pools, and miles of scenic marshfront beauty. Ideally positioned between Beaufort, Bluffton, Hilton Head, and Savannah, 8 Chechessee Circle offers the perfect balance of privacy, luxury, natural beauty, and convenience.

8 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

6 Dolphin Landing, Okatie
$2,895,000
5 Beds ⋅ 5 Baths ⋅ 3,906 SqFt. ⋅ HILTONHEAD-508380 MLS
A differеnt rhythm takeѕ hοld at Cаllаwаsѕіe Island, a canοpу of live oaks, tidal marsh, and quiet surroundings create a setting that feels worlds away. At the end of a cul-de-sac, on Dolphin Landing, this newly constructed custom home emerges with quiet confidence. From the moment you step inside, the experience is immediate. The great room opens to long, unobstructed views, anchored by a dramatic sleek fireplace with Old World tabby surround. Soaring ceilings, rich wood floors, and custom detailing create a sense of volume while allowing light and landscape to take center stage. The kitchen is defined by striking architectural detail, including a coffered ceiling, an oversized island, and is equipped with Sub-Zero refrigeration and a Wolf six-burner range with double ovens. A private prep space, walk-in pantry, and adjoining laundry/mudroom provide function and flow, with direct access to the outdoor summer kitchen. Privately positioned, the primary suite captures serene views with a wood feature wall, dual dressing areas, and a bath of notable scale and sophistication. Each additional bedroom offers an ensuite with double vanities and walk-in closets. The distinctive private carriage house above the three-car garage includes a separate entrance, kitchenette, bedroom, full bath, and walk-in closet-ideal for extended stays and finished with the same level of craftsmanship carried throughout the residence. Outdoor living is equally compelling, with a screened porch overlooking the marsh where wildlife and shifting tides create a dynamic backdrop. Positioned for uninterrupted views and golden hour exposure, the setting offers a rare sense of privacy. Every detail has been intentionally designed from the climate-controlled wine room and tabby accents to the layered textures, custom finishes, and thoughtfully crafted elements reflected throughout the home. A rare opportunity to own a newly built home of this caliber within one of the Lowcountrys most private and naturally beautiful communities.

6 Dolphin Landing, Okatie

Listing courtesy of Charter One Realty.

5 Oyster Court, Okatie
$849,000
3 Beds ⋅ 3 Baths ⋅ 2,303 SqFt. ⋅ HILTONHEAD-507814 MLS
Completely reimagined and impeccably renovated, 5 Oyster Court on Callawassie Island is a true Lowcountry gem that blends timeless charm with modern sophistication. Every detail has been thoughtfully curated in this top-to-bottom transformation, showcasing high-end finishes, designer touches, and quality craftsmanship throughout. The well-designed floor plan offers comfortable, easy living and effortless flow for entertaining, while the stunning updated kitchen serves as the heart of the home with premium appliances, custom cabinetry, and elegant surfaces. The spacious primary suite provides a serene retreat, complemented by beautifully renovated baths that evoke a spa-like experience. Additional guest rooms offer comfort and privacy, and the third bedroom offers flexibility as an ideal home office or study. Extending across the entire back of the home, an oversized screened porch creates the perfect setting for relaxing or entertaining while enjoying the peaceful Lowcountry surroundings. Significant upgrades provide added value and peace of mind, including all new windows, new HVAC system, and new hot water heaters. Nestled on a quiet cul-de-sac, the property offers a tranquil setting with inviting outdoor spaces to enjoy the natural beauty of Callawassie Island. Ideally located just moments from the River Club, deep water docks, and family pool, this home provides easy access to some of the community's most sought-after amenities. This move-in-ready home presents a rare opportunity to own a fully renovated residence in one of the Lowcountry's most desirable private communities, known for its championship golf, deepwater access, and exceptional amenities.

5 Oyster Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

8 River Marsh Lane, Okatie
$695,000
3 Beds ⋅ 3 Baths ⋅ 2,276 SqFt. ⋅ HILTONHEAD-507603 MLS
This Ꮮowcountrу hοme, іdеаlly ѕіtuated within the Club Cottagе sеction of Callawassie Island, offers a unique blend of flexibility and lifestyle, perfect as a primary residence, second home, or an investment opportunity with rental income potential as you begin your transition south.Featuring 3 bedrooms and 3 baths, the home is thoughtfully positioned to capture sweeping golf and marsh views overlooking Dogwood #9. A spacious rear porch with cable railings enhances the setting, allowing for uninterrupted, expansive views and seamless outdoor living. The Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

8 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

4 Bent Tree Lane, Okatie
$900,000
4 Beds ⋅ 4 Baths ⋅ 3,925 SqFt. ⋅ HILTONHEAD-507539 MLS
Set agаinst a brеаthtakіng Ꮮοwcοuntrу backdrop, this stаtelу custom home offers timeless character, generous living spaces, and an extraordinary setting that captures the very essence of coastal living. Perfectly positioned on a homesite with a deep, wide western exposure, the sweeping marsh views stretch endlessly to the Colleton River, delivering unforgettable sunsets that paint the sky each evening. Spanning approximately 3,925 square feet, this classic residence features 4 bedrooms and 3.5 baths, thoughtfully designed for both comfort and functionality. Expansive living room and gorgeous foyer define this home and are anchored by the beauty of moss-draped live oaks and marsh views. For a more informal, relaxed living space, the large family room, complete with an office nook and bar sink, ideal for entertaining or relaxed everyday living, is only a few steps away from the kitchen area. The second-floor loft offers an oversized retreat for the additional 2 guest bedrooms overlooking the marsh, creating a serene vantage point for soaking in the natural beauty that surrounds you. The home's inviting outdoor spaces are equally impressive. A full front porch welcomes you with classic Southern charm, while the rear deck flows seamlessly into a screened gazebo-perfect for al fresco dining, quiet afternoons, or simply enjoying the coastal breeze. Beneath the elevated back porch, ample storage provides practical convenience. Inside, elegant details abound. Custom built-ins enhance the living room, while the dining area features beautifully crafted cabinetry. Hardwood floors run throughout the main living areas, complemented by comfortable carpeting in the bedrooms. The primary suite offers a private retreat with dual vanities, spacious closets, a jetted tub, and a separate shower. An additional guest bedroom on the main level provides flexibility for visitors. Surrounded by mature landscaping and framed by majestic live oaks, the property exudes natural beauty and privacy. With its rare combination of location, views, and classic Lowcountry design, this home presents an exceptional opportunity to create your own coastal sanctuary. (Digital enhancement has been used in some photographs)

4 Bent Tree Lane, Okatie

Listing courtesy of Charter One Realty.

26 Longwood Drive, Okatie
$999,999
4 Beds ⋅ 4 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-503887 MLS
When you сross οvеr the саuѕewау into Callawassіe Ιsland, you are transported into a peaceful private world where moss-draped oaks, winding marsh views, and quiet coastal beauty instantly replace the pace of everyday life, creating a true sense of retreat the moment you arrive. Driving past beautifully manicured golf fairways woven seamlessly with natural wildlife habitat and serene lagoons, every turn offers a blend of refined landscape and untouched Lowcountry beauty. The charm continues right into this new construction home, where thoughtful design and setting feature 3 bedrooms in the main house and an in-law suite above the garage. It's perfect for guests, extended family, or flexible living arrangements that adapt easily to your lifestyle. Welcome home to 26 Longwood.

26 Longwood Drive, Okatie

Listing courtesy of Moul, REALTORS®.

54 Osprey Circle, Okatie
$1,399,999
4 Beds ⋅ 5 Baths ⋅ 3,441 SqFt. ⋅ HILTONHEAD-506875 MLS
Looking for timeless luxury in a quiet, serene neighborhood that offers world-class amenities within a gated and secure island community? Then you must see and make this meticulously designed custom home built by Sunset-Life Properties your new sanctuary! Located on the green of Tom Fazio's Magnolia #4 golf hole, par 4, this home has far more elegant features than can be listed here. No expense was spared to have the finer things in life! GE Monogram appliances including 42" side by side refrigerator, 36" gas range with 6 burners and pot filler in backsplash above, Double Oven in addition to oven in range, 24" Dishwasher, Microwave, and 2 sets of Double Drawer Refrigerators both in the Kitchen and Bonus Bar above on the Second Floor. Both areas also have Scotsman 30 lb Gourmet Ice Makers, and the home is even furnished with Electrolux stacked front loading 4.5 cft Washer and 8 cft Dryer. The cabinets are 3/4" plywood Wood-Mode and Brookhaven luxury brands with walnut interior, dovetail construction, and soft close. An Isokern propane fireplace is in the Family Room and 3CM custom granite countertops are installed throughout the home. PLAY Custom Home Technology is installed in this home with predefined engraved labeled switches making it easy to push the right one. This home even features areas prepped for an outdoor kitchen on a separate Grill Porch and a bar area on the Screened Porch. Spray foam insulation thoughout this home with 3 zones for AC and jamb switches for closet lights. This home is a MUST SEE along with the Callawassie Island Community!!!

54 Osprey Circle, Okatie

Listing courtesy of Realty One Group - Lowcountry.

49 Heron Walk, Okatie
$329,000
3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-505169 MLS
Welcome to 49 Heron Walk on Callawassie Island. Perfectly positioned on the fairway of the 1st hole of the Dogwood Course, this classic golf cottage delivers a true front-row seat to opening drives and glowing morning sunrises over the fairway. Lovingly maintained in remarkable original condition (with updated mechanicals), the home features warm woodwork, comfortable living spaces, and authentic 80s character throughout. Enjoy it just as it is, or modernize to your taste--either way, you're starting with an unbeatable golf course setting and timeless island appeal. Live here full time, use as a 2nd home or create income as a sought-after retreat for visiting golfers. This is island living with timeless style. Optional Golf Membership.

49 Heron Walk, Okatie

Listing courtesy of Moul, REALTORS®.

64 Osprey Circle, Okatie
$700,000
3 Beds ⋅ 4 Baths ⋅ 2,580 SqFt. ⋅ HILTONHEAD-504968 MLS
Experience the romance of Lowcountry living on Callawassie Island. Tucked beneath towering pines on a quiet, private homesite, this 2,580 sq ft home offers 3BR/3BA plus a dedicated office and captivating lagoon-to-golf views. A classic brick stairway leads to an expansive, columned front porch-rocking-chair ready and cooled by ceiling fans-setting the tone for slow mornings, sweet tea afternoons, and sunset conversations. Inside, enjoy light-filled living spaces and a gourmet kitchen built for gathering, featuring custom cabinetry, stainless appliances, a professional-style gas range with statement hood, and an oversized granite island with sink and abundant storage. The spacious primary suite is a true retreat with tranquil views and a spa-inspired bath with dual vanity, soaking tub, and separate shower. Two additional bedrooms and baths provide comfort and flexibility for guests. Out back, the screened porch and patio deliver the quintessential Lowcountry backdrop-breezes through the trees, birdsong overhead, and front-row vistas across the lagoon to the fairway beyond. Callawassie Island's gated community elevates the lifestyle with an exceptional club experience, including golf, tennis, fitness, pool, dining, and miles of protected marsh and waterways.

64 Osprey Circle, Okatie

Listing courtesy of Charter One Realty.

50 Callawassie Club Drive, Okatie
$599,000
3 Beds ⋅ 3 Baths ⋅ 2,124 SqFt. ⋅ HILTONHEAD-502292 MLS
Enjoу the Callawаѕsіе Ιslаnd Ꮮifestyle, within thе pοpular Club Cottage Section, as a Primary Home or 2nd Home with rental/investment potential. Ideally located within a short walk to Tennis, Tennis Pro-Shop & Pickleball Courts, Fitness Facility, Pool, Main Clubhouse, Golf Pro Shop and Golf Practice Facility. This well-conditioned home, with an open floor plan, exudes comfort and functionality. Tranquil pond and private Golf views of the Dogwood #1 hole. All piping replaced 2025. Callawassie Island offers an amazing community of kind people, breathtaking natural beauty, endless activities, top notch golf with total privacy and security. Furnishings are negotiable.

50 Callawassie Club Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

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