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50 Spring Island Drive, Okatie
$995,000
ACTIVE Status ⋅ 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.

8 Chechessee Circle, Okatie
$914,000
ACTIVE Status ⋅ 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.

14 Links Drive, Okatie
$975,000
CLOSED Status ⋅ 3 Beds ⋅ 4 Baths ⋅ 2,826 SqFt. ⋅ HILTONHEAD-508314 MLS
Rare new construction opportunity on Callawassie Island, privately situated on a quiet cul-de-sac with beautiful long golf course views. Built as the builder's personal residence, 14 Links Drive showcases thoughtful design, quality craftsmanship, and a highly functional floor plan ideal for modern Lowcountry living. This light-filled home features an open-concept living, dining, and kitchen layout with clean coastal finishes, wide-plank flooring, abundant windows, and seamless indoor-outdoor flow. The designer kitchen offers white cabinetry, quartz-style countertops, stainless steel appliances, gas cooking, a large island with seating, and excellent workspace for everyday living or entertaining. The bedroom layout is exceptional, offering 3 bedrooms, each with its own ensuite bathroom, plus a private office/flex room adjacent to a 4th full bathroom - ideal as a home office, guest space, hobby room, or potential 4th bedroom. The screened porch is a true highlight, capturing peaceful, private views across the golf course and surrounding natural landscape. A major bonus is the oversized 3-bay garage, complete with a separate conditioned space currently used as an exercise room and ideal for a workshop, studio, gym, storage, or golf cart/lifestyle gear. With new construction, flexible living spaces, golf views, privacy, and a desirable Callawassie Island location, this home delivers the Lowcountry lifestyle buyers are searching for.

14 Links Drive, Okatie

Listing courtesy of Charter One Realty. Selling Office: Century 21 Integra.

50 Camp Saint Mary Road, Okatie
$955,000
CLOSED Status ⋅ 4 Beds ⋅ 4 Baths ⋅ 2,916 SqFt. ⋅ HILTONHEAD-508295 MLS
Welcome home to 50 Camp St. Mary's Rd.. If you're looking for space with no POA this is a fabulous opportunity to own a Lowcountry style home on a beautifully landscaped acre in a spectacular location near the banks of the Okatie River. This 4 Bedroom 3 and a half bath home has a mother in law suite above the garage for family use or rentals. There is also Boat/storage on site as well as a detached porch for entertaining. Enjoy the lowcountry wrap around porch at your pleasure. This home is just steps away from a riverfront county dock, with an equestrian boarding facility located nearly adjacent to the property, this ownership opportunity presents the best of both world's without the costs associated with home ownership in nearby gated communities. A short drive to both the towns of Bluffton and Beaufort, 50 Camp Saint Mary's Road is an opportunity not to be delayed further.

50 Camp Saint Mary Road, Okatie

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

4 Bent Tree Lane, Okatie
$900,000
ACTIVE UNDER CONTRACT Status ⋅ 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
ACTIVE Status ⋅ 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®.

4 Heron Point, Okatie
$975,000
CLOSED Status ⋅ 4 Beds ⋅ 3 Baths ⋅ 3,250 SqFt. ⋅ HILTONHEAD-504516 MLS
SELLER OFFERING TO CONTRIBUTE TO COMMUNITY ENHANCEMENT FEE WITH ACCEPTABLE OFFER. Encircled by lush maritime forests between the Dogwood course and the marshland stretching toward Spring Island, 4 Heron Point is a 4-bedroom cottage style home that speaks to the natural beauty and grandeur of Callawassie Island. The open living space at the heart of the home exults in airy cathedral ceilings above a great room boasting wide-plank pine flooring, carefully crafted custom built-ins and a wide fireplace surrounded by intricate woodwork. Open to the great room, the chef's kitchen masterfully blends form and function with alder wood cabinets, wide granite center island complementing the granite backsplash, updated stainless steel appliances and a massive pantry. This effortless flow, coupled with the whole-home sound system, sets the stage for unforgettable entertaining. Formal dining nearby surrounds you with refined shiplap walls and custom light fixtures, bathed in light from tall windows out to the Lowcountry porch. Through wide screens, this year-round outdoor living space soaks in panoramic views through the forest to the 6th hole on the Dogwood Course, with fans and heaters for comfort in every season. Along with these grand spaces, the home's layout allows for several more intimate spaces for solitude and quiet reflection. A stately office off of the main living space wraps you with gorgeous arched built-ins and views of the front entry, embodying old-world formality. A larger flex space above the two-car garage provides the opportunity to create a secluded office space, media room, home gym or guest suite with its full bath. Capped by a soaring geometric tray ceiling, the primary suite indulges with a sublime sense of space and luxe amenities from a massive walk-in closet to a spa-like en suite with tile-lined garden tub, wide granite-topped dual-basin vanity and corner walk-in shower. The ground floor also holds the home's three bedrooms, each with its own luxurious amenities. Along one wing of the home, a pair of bedrooms shares access to a full bath with tub and shower, each enjoying wide closets and elegant spaciousness. The rear bedroom even enjoys its own peaceful sunroom gazing out toward the golf views. With each space, this property offers a fresh interpretation of the sophisticated rusticism that sets Callawassie Apart. Elegant and refined in its appointments, but built in harmony with unspoiled nature.

4 Heron Point, Okatie

Listing courtesy of Maxey Blackstream Christie's International Real Estate. Selling Office: Coastal Real Estate Solutions II.

6 Winding Oak Drive, Okatie
$940,000
CLOSED Status ⋅ 4 Beds ⋅ 5 Baths ⋅ 3,095 SqFt. ⋅ HILTONHEAD-504320 MLS
Over 3,000 sq ft of refined living space-including a complete 916-sq-ft second-story addition-sets this marshfront masterpiece apart, offering a level of fit and finish rarely found under $1M on Callawassie Island. This classic Lowcountry home has been fully reimagined with a top-to-bottom, high-end renovation blending timeless architecture with modern elegance. Highlights include a chef's kitchen, premium flooring and millwork, energy-efficient spray-foam insulation, and major structural upgrades, creating a 4-bedroom, 4.5-bath residence designed for comfort and style.Thoughtfully nestled among mature native hardwoods, the home offers serene views of Sugar Mill Creek from the back decks and nearly every room. Callawassie Island delivers a premier Lowcountry lifestyle with 27 holes of Tom Fazio-designed golf, professional racquet facilities, two clubhouses with deepwater access, and luxury wellness amenities-all within South Carolina's first certified Community Wildlife Habitat. Ideally located between Beaufort and Bluffton, residents are within 35 minutes of Hilton Head Island, Savannah, and the Savannah/Hilton Head International Airport. See why 6 Winding Oak Drive truly stands alone in today's market.

6 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Coastal Real Estate Solutions II.

2 Chechessee Circle, Okatie
$875,000
CLOSED Status ⋅ 4 Beds ⋅ 3 Baths ⋅ 2,833 SqFt. ⋅ HILTONHEAD-503950 MLS
Privately positioned on a secluded corner lot with sweeping marsh views, this Callawassie Island home offers 4 bedrooms and 3 bathrooms with the added peace of mind of a brand new roof. The open floor plan captures expansive marsh views while maximizing natural light throughout. The first-floor primary suite overlooks the marsh and features a beautifully appointed bathroom. A bonus room with a full bath adds flexibility for guests or entertaining. Outdoor living shines with a private deck and hot tub where you can unwind and enjoy peaceful marsh views and exceptional privacy. Life on Callawassie Island is defined by world-class amenities, natural beauty, and a strong sense of community, offering an active and refined lifestyle.

2 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Charter One Realty.

61 Winding Oak Drive, Okatie
$865,000
CLOSED Status ⋅ 3 Beds ⋅ 3 Baths ⋅ 2,435 SqFt. ⋅ HILTONHEAD-502431 MLS
Newer construction, refined Lowcountry design, and future expansion potential come together at 61 Winding Oak Drive, a 2024 custom-built home on prestigious Callawassie Island. Positioned on an elevated homesite along the newly renovated Magnolia Golf Course, this bright one-level residence offers privacy, quality, and an unusually versatile layout for buyers who want ease of living today with room to grow tomorrow.A tabby driveway with brick apron sets the tone, while the front porch captures a glimpse of the river just across the street. Inside, natural light highlights French oak floors, cottage-style trim, custom window treatments, and a crisp, timeless palette. The open-concept living area features vaulted ceilings, a gas fireplace, and seamless flow into the kitchen and dining spaces.The kitchen was designed to both impress and perform, with abundant cabinetry, and a butler's pantry that adds charm, storage, and everyday function. The main level includes 3 bedrooms, 2.5 baths, a dedicated home office, and a heated/cooled storage room that could serve as a second office, hobby room, fitness space, or additional flex area.One of the most compelling features is the expansive walk-up attic space. Already offering substantial storage, lighting, this area presents a valuable opportunity for future finished living space, a bonus room, guest suite, studio, media room, or potential 4th bedroom configuration, subject to permitting. In a market where many buyers want newer construction but hesitate over limited bedroom count, this home offers a rare path to added functionality without sacrificing the convenience of one-level living.The primary suite is a true retreat with two closets featuring custom solid wood built-ins and a well-appointed bath. Outdoor living is equally inviting with a screened porch, large patio with pergola, and a spacious backyard ideal for relaxing, entertaining, or enjoying the peaceful golf-course setting.Additional highlights include an oversized 2 car garage with golf cart bay and a tankless Rinnai water heater. Beyond the home, Callawassie Island offers an exceptional private island lifestyle with golf, tennis, pickleball, fitness, deepwater access, dining, and a vibrant social scene surrounded by the natural beauty of the Lowcountry.

61 Winding Oak Drive, Okatie

Listing courtesy of Coldwell Banker Access Realty. Selling Office: Peirce Group Brokered by EXP Realty LLC.

21 Osprey Circle, Okatie
$900,000
CLOSED Status ⋅ 4 Beds ⋅ 5 Baths ⋅ 3,543 SqFt. ⋅ HILTONHEAD-450920 MLS
Welcome to Southern elegance at its finest! Nestled on a private and serene 0.80-acre lot, this stately custom Lowcountry home is the perfect blend of charm, comfort, and sophistication. The main residence offers 3 bedrooms and 3.5 bathrooms, while a beautifully appointed guest cottage provides an additional 1 bedroom and 1 bathroom ideal for visitors or multi-generational living. Designed with entertaining in mind, the open and airy layout features a chefs kitchen, formal dining room, and a spacious family room with a dual-sided gas fireplace that flows seamlessly into the great room. The first-floor primary suite is a true retreat, complete with a luxurious en-suite bath and a generous walk-in closet. Step outside to a covered porch perfect for morning coffee or evening gatherings, all surrounded by lush landscaping and upscale custom finishes throughout. Experience the best of island living and take advantage of the premier amenities this sought-after community has to offer. Schedule your private tour today this is Lowcountry living at its finest! *Seller will pay half of HOA initiation with accepted offer*

21 Osprey Circle, Okatie

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

46 Spring Island Drive, Okatie
$870,000
CLOSED Status ⋅ 3 Beds ⋅ 4 Baths ⋅ 2,780 SqFt. ⋅ HILTONHEAD-443821 MLS
Hidden from the street, beyond dense woods of moss-draped oaks and mature hardwoods, the landscape opens to reveal a custom-built southern cottage. In keeping with the lowcountry tradition, the expansive front and rear porches invite you to enjoy the simple pleasures of life, like sipping sweet tea in the morning and observing golfers in the afternoon. Crown molding, built-in cabinetry, tray ceiling, roll-out pantry, pocket doors and spray foam insulation display functionality and quality craftsmanship. Located between Bluffton and Beaufort, you will find plenty of ways to engage and unwind in this amenity-rich and socially-active club!

46 Spring Island Drive, Okatie

Listing courtesy of Weichert Realtors Coastal Properties. Selling Office: Coastal Real Estate Solutions II.

3 Raintree Lane, Okatie
$885,000
CLOSED Status ⋅ 3 Beds ⋅ 4 Baths ⋅ 2,916 SqFt. ⋅ HILTONHEAD-441046 MLS
Stunning Riverbend home offering 3 bedrooms with an expansive bonus room lending flexibility for extra guests, home office or live-in assistance. The HW flooring flows seamlessly throughout the main living areas. The kitchen provides a timeless aesthetic, featuring white cabinets complemented by a subway tile backsplash. Stainless appl's, including a 5-burner gas range, elevating the cooking experience. Enjoy meals in the formal dining room, where plantation shutters add a touch of southern charm. Retreat to the primary suite, featuring a tray ceiling w/crown molding & accent lighting. Enjoy the 2 car garage + golf cart bay w/epoxy flooring.

3 Raintree Lane, Okatie

Listing courtesy of Keller Williams Realty. Selling Office: Southern Lifestyle Properties of SC LLC.

14 Sequoia Court, Okatie
$970,000
CLOSED Status ⋅ 3 Beds ⋅ 3 Baths ⋅ 2,549 SqFt. ⋅ HILTONHEAD-438676 MLS
Tucked away at the end of a cul de sac in a spectacular park like setting of moss-draped oaks & picturesque views of the marsh, the stunning residence has been totally renovated w designer finishes. This beautiful home is sited on nearly an acre of private land, features 2 en suite primary bedrms, chefs kitchen w honed quartz & new appliances, Carolina Room w sweeping views and very large outdoor deck. Minutes from world-class amenities of Callawassie Island, including a riverfront dock, dining, pools, fitness, golf, tennis & more. The ultimate retreat is for anyone seeking solitude. This island-like sanctuary is Lowcountry perfection. OSCREA

14 Sequoia Court, Okatie

Listing courtesy of Engel & Volkers. Selling Office: Coastal Real Estate Solutions II.

22 Longwood Drive, Okatie
$925,000
CLOSED Status ⋅ 3 Beds ⋅ 2 Baths ⋅ 2,181 SqFt. ⋅ HILTONHEAD-428712 MLS
New Custom-Built home by Artisan Custom Homes, recent winner of 3 Hilton Head Area Homebuilders Association LightHouse Award's- Best Overall Award, Best Exterior and Best Bath. The Bayberry is the epitome of Southern Living, boasting desirable open floor, large great room, and complimented by an inviting screened porch, and formal dining room and office. The property is roughly .67 acres, w 10-12 foot elevation throughout, and importantly located on a short cul-de-sac, just steps from the Amenities. Experience the unparalleled island lifestyle from this central, yet private oasis amongst the Mossy-draped Live Oaks, and true serenity!

22 Longwood Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Coastal Real Estate Solutions II.

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