View All Callawassie Island, Okatie, SC Homes with Home Office Listings

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.

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.

204 Callawassie Drive, Okatie
$1,425,000
4 Beds ⋅ 5 Baths ⋅ 3,223 SqFt. ⋅ HILTONHEAD-512910 MLS
An Exquisite Custom Craftsman Retreat in Oyster Cay's Most Coveted Enclave. From the moment you arrive, a graceful wraparound driveway and elegant breezeway announce the timeless craftsmanship of this extraordinary custom-built residence. Gas-lit lanterns cast a warm glow over meticulously curated landscaping, setting a tone of refined Southern elegance from the very first glimpse.Step inside to wide-plank white oak flooring and artisan shiplap detailing flowing throughout a thoughtfully designed floorplan, where multiple living spaces are scaled just right, offering ample room, easy flow, and endless possibilities for entertaining. Sound insulation around the interior walls of bathrooms and the laundry room ensures peace in every corner, while a dedicated home office in the main house offers a quiet space to work from home. This residence is a private sanctuary devoted to wellness. A whole-house water filtration system delivers pure, spa-quality water throughout, while a 4-person infrared sauna with red light therapy invites daily detoxification and restoration. An all-in cold plunge completes the experience, offering enhanced recovery, elevated metabolism, and unmatched mental clarity, spa-level wellness now at home.Outdoor living takes center stage with an oversized 15x18 screened porch, anchored by a gas fireplace and flat-screen television, creating a natural gathering space in every season. Beyond it, the 26x20 covered outdoor kitchen, complete with a built-in Big Green Egg, flattop grill, granite countertops, and abundant custom cabinetry, overlooks a wooded homesite of exceptional privacy. A whole-property Mosquito Nix system keeps outdoor spaces bite-free, while electrical is already run for a future hot tub. Above the garage, a well-appointed suite offers its own bath and private separate entrance, ideal for guests, multigenerational living, or a home office. Perfectly positioned just moments from the community pool, two deep-water docks, and the exclusive River Club, this home offers the rare balance of privacy and quiet sophistication, tucked away yet close to everything Callawassie Island has to offer.

204 Callawassie Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

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.

12 Dolphin Lane, Okatie
$1,467,500
4 Beds ⋅ 4 Baths ⋅ 3,554 SqFt. ⋅ HILTONHEAD-510537 MLS
Built in 2015 by renowned custom builder Steve Tilton, owner of Coastal Signature Home, this impeccably maintained coastal residence offers over 3,554 square feet of thoughtfully designed living space overlooking breathtaking panoramic views of Chechessee Creek and the surrounding marshlands. Indirect sunrise and sunset views create an incredible opportunity to enjoy Callawassie Island at its very best! With three spacious bedrooms on the main level, this beautiful home offers easy one-level living. Perfectly positioned on a private cul-de-sac with desirable northeastern exposure, this four-bedroom, three-and-a-half-bath home seamlessly blends timeless craftsmanship with modern comfort. Rich architectural details and exquisite millwork are showcased throughout, while random-width reclaimed pine flooring adds warmth and character to the home's elegant interiors. Designed to maximize its spectacular setting, the living room, kitchen, breakfast nook, family room, primary bedroom, and guest bedroom all enjoy direct water and marsh vistas. The home features both formal and casual living spaces, including inviting formal living and dining rooms, in addition to an expansive open-concept family room and kitchen. The soaring 16-foot vaulted ceiling creates a dramatic focal point, while the chef's kitchen is appointed with premium appliances, a gas cooktop, and a refrigerator replaced in 2025. Outdoor living is equally impressive. A 400-square-foot screened porch with a gas fireplace provides the perfect setting for year-round enjoyment, whether entertaining guests or simply taking in the tranquil waterfront scenery and wildlife activity. A significant enhancement completed in October 2024 added a spacious 536-square-foot bonus room with a full bath and beautifully finished ceramic tile shower, offering exceptional flexibility for guests, a home office, media room, or private retreat. Additional features include a tankless water heater, a spacious walk-up attic with spray foam insulation for energy efficiency and abundant storage, as well as an insulated crawl space. The exterior was freshly painted in May 2026, adding to the home's appeal and maintenance value. Offering exceptional craftsmanship, stunning natural views, and move-in-ready condition, this remarkable custom home presents a rare opportunity to enjoy refined Lowcountry living at its finest.

12 Dolphin Lane, Okatie

Listing courtesy of Charter One Realty. Selling Office: 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.

14 Links Drive, Okatie
$975,000
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.

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.

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.

4 Heron Point, Okatie
$975,000
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.

61 Winding Oak Drive, Okatie
$865,000
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.

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Callawassie Island, Okatie, SC · Curated MLS Search

Homes with Home Office in Callawassie Island, Okatie, SC

An editorially curated view of every active homes with home office listing in Callawassie Island, Okatie, SC. Updated in real time from the local MLS, presented without the noise.

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