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$899,000
4 Beds ⋅ 4 Baths ⋅ 3,587 SqFt. ⋅ HILTONHEAD-512387 MLS
This quintessential Lowcountry home offers easy one-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.

$1,395,000
4 Beds ⋅ 5 Baths ⋅ 3,030 SqFt. ⋅ HILTONHEAD-512044 MLS
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 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 firepit, 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 dedicated golf cart bay and epoxy floors is topped by a 558-square-foot FROG with 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.

$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.

$1,350,000
4 Beds ⋅ 5 Baths ⋅ 2,891 SqFt. ⋅ HILTONHEAD-508194 MLS
The Palmetto's thoughtfully designed single-level floor plan offers views of a lagoon and the 8th hole of the Magnolia Golf Course. Featuring more than 2,800 square feet of beautifully appointed living space, the open-concept layout features a spacious primary suite, a welcoming dining room and great room, and guest bedrooms-each with its own bathroom. Above the attached garage, you will find a private studio with a full bath that provides flexible space for guests, extended family, or a home studio. If indoor-outdoor living is a priority, this home truly shines. The vaulted kitchen and dining area create a dramatic focal point, and when the doors open to the screened porch, the space transforms into an entertainer's dream-seamlessly blending comfort and style. With a total of four bedrooms, four-and-a-half baths, and a dedicated office, the Palmetto has everything you need and more. Summer 2026 completion.

32 Longwood Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,475,000
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.

$946,900
4 Beds ⋅ 3 Baths ⋅ 2,801 SqFt. ⋅ HILTONHEAD-509015 MLS
Nestled on a private circle within the prestigious Callawassie 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, the residence features expansive windows that flood the home with natural light while showcasing the stunning scenery from nearly every room. The spacious great room with cathedral ceilings and a cozy fireplace flows seamlessly into the Carolina room and updated kitchen, making the home ideal for entertaining or quiet relaxation. Recent improvements include new wide plank engineered oak floor coverings and a new HVAC system installed this year, adding both style and modern comfort throughout the home. The primary suite offers a serene escape with tranquil water views, beautifully renovated baths, and generous walk-in closets. Flexible living spaces provide options for a home office, formal dining room, or additional guest accommodations. Outdoor living is equally inviting, with a large deck perfect for enjoying morning coffee, evening sunsets, 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, pickle ball, fitness facilities, community docks, dining, pools, and miles of scenic marsh front beauty. Ideally positioned between Beaufort, Bluffton, Hilton Head, and Savannah, this home offers the perfect balance of privacy, luxury, and convenience.

8 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,899,900
4 Beds ⋅ 5 Baths ⋅ 4,470 SqFt. ⋅ HILTONHEAD-508950 MLS
Brand-new custom luxury Lowcountry retreat nestled near the end of the peninsula on a quiet, private wooded cul-de-sac in desirable Woodstork Watch on Callawassie Island, surrounded by similarly impressive high-end custom homes. This expansive newly constructed residence offers stunning high-tide marsh views and exceptional craftsmanship throughout, including energy-efficient 2x6 construction and spray foam insulation. Designed to embrace the Lowcountry lifestyle, the home features seamless indoor and outdoor living transitions on both the first and second levels, creating inviting spaces for entertaining and relaxation. Soaring cathedral ceilings enhance the open and airy feel of the main living spaces, while sophisticated custom black steel railings add striking architectural detail throughout the home. The gourmet JennAir kitchen is designed for entertaining with a massive center island, six-burner gas range, premium appliances, and an elegant scullery for added prep and storage space. An expansive upstairs loft with private balcony captures peaceful marsh views and offers additional living and gathering space. A full private living area above the garage with its own kitchenette provides ideal space for guests, extended family, or multigenerational living. Enjoy refined finishes, modern luxury, and the perfect blend of privacy and Lowcountry beauty in one of the island's most sought-after settings. Widely regarded as one of the premier locations in Beaufort County, Callawassie Island offers an exceptional Lowcountry lifestyle with convenient access to Beaufort, Bluffton, Hilton Head Island, and the historic cities of Charleston and Savannah.

7 Woodstork Watch, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$2,995,000
5 Beds ⋅ 5 Baths ⋅ 3,906 SqFt. ⋅ HILTONHEAD-508380 MLS
A different rhythm takes hold at Callawassie Island, a canopy 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. Enjoy an exclusive buyer benefit: with an accepted offer, the Seller will pay the one-time Club Initiation Contribution Fee, allowing you to begin enjoying all that Callawassie Island has to offer from day one.

6 Dolphin Landing, Okatie

Listing courtesy of Charter One Realty.

$900,000
4 Beds ⋅ 4 Baths ⋅ 3,925 SqFt. ⋅ HILTONHEAD-507539 MLS
Set against a breathtaking Lowcountry backdrop, this stately 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.

$1,080,000
4 Beds ⋅ 4 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-503887 MLS
When you cross over the causeway into Callawassie Island, 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®.

$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.

$1,025,000
4 Beds ⋅ 4 Baths ⋅ 3,990 SqFt. ⋅ HILTONHEAD-505127 MLS
Classic Lowcountry charm meets privacy and sweeping golf views in this beautifully maintained home set on over one acre on Callawassie Island. Positioned more than 300 feet from the road along a tree-lined, landscaped drive, the home offers exceptional curb appeal and a peaceful setting overlooking the recently renovated Dogwood golf course. The thoughtfully designed floor plan features 4 bedrooms and 3.5 baths, including a spacious first-floor primary suite and a dedicated office. Upstairs guest bedrooms and a versatile bonus room provide comfortable space for family or visitors. Hardwood floors, custom built-ins, detailed millwork, and numerous walk-in closets enhance the home's character and functionality. Floor-to-ceiling windows along the rear of the home fill the living spaces with natural light and showcase the beautiful golf course views, while the screened porch offers the perfect place to relax and enjoy the professionally landscaped yard. A wonderful opportunity to enjoy classic Lowcountry living in the sought-after community of Callawassie Island.

50 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,795,000
4 Beds ⋅ 4 Baths ⋅ 3,300 SqFt. ⋅ HILTONHEAD-504585 MLS
Enjoy exceptional waterfront living on Callawassie Island with rare western exposure and unforgettable sunset views over the tidal marshes of Chechessee Creek, complemented by peaceful water and golf views from the front of the home. Privately positioned, this pristine custom-built residence offers a true Lowcountry lifestyle with a private short dock, floating dock, and new boat lift providing direct water access for boating, kayaking, and sunset cruises. Designed for both everyday comfort and effortless entertaining, the open floor plan is centered around a chef's kitchen featuring Wolf and Sub-Zero appliances, a 10-foot island, beverage bar, wine cooler, and ice maker. Wide plank hardwood floors flow throughout the main living areas, while two first-floor guest suites offer beautifully remodeled en suite baths for privacy and convenience. Thoughtful improvements enhance both form and function, including a newer roof, new deck and shutters, a custom-built fireplace with new insert, replaced interior doors, all new water piping, spray foam insulation in the crawl space, new crawl space screening, updated lighting, refreshed landscaping, and a full exterior repaint in 2025.Expansive outdoor living spaces capture sweeping marsh views and glowing sunsets, creating a serene and private backdrop that changes with the tides and seasons. Residents enjoy the unmatched lifestyle of Callawassie Island-an engaging community, remarkable natural beauty, top-tier golf and amenities, endless outdoor activities, and the peace of mind that comes with gated security and true Lowcountry privacy.

41 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,399,000
4 Beds ⋅ 4 Baths ⋅ 3,680 SqFt. ⋅ HILTONHEAD-505052 MLS
Lowcountry waterfront living on Callawassie Island in Okatie, SC. Built by award-winning builder Steve Tilton, 47 Sugar Mill is tucked away at the end of a quiet cul-de-sac and surrounded by ancient live oaks draped in Spanish moss for a truly private, coastal setting, and boasts a brand new roof in June 2026. This 4BR + office home is designed for relaxed island living with oversized front, back, and screened porches-perfect for morning coffee, afternoon breezes, and evening gatherings. Inside, soaring cathedral ceilings, a welcoming fireplace, and abundant natural light create an inviting main living space that seamlessly connects to the outdoors. The rare showstopper is the backyard on a tidal creek with a floating dock and boatlift-opening the door to a lifestyle of kayaking, paddleboarding, boating, fishing, and crabbing right from home. A 2.5-car garage includes a dedicated golf cart bay for easy island exploring. If you've been searching for a Callawassie Island waterfront home with a dock and lift, 47 Sugar Mill is a standout opportunity.

47 Sugar Mill Drive, Okatie

Listing courtesy of Charter One Realty.

$1,350,000
4 Beds ⋅ 4 Baths ⋅ 2,791 SqFt. ⋅ HILTONHEAD-502916 MLS
Discover the pinnacle of Lowcountry living in this brand-new, 4-bed, 3.5-bath marsh front home by Sumerall Custom Construction. Sited on a quiet street and framed by 10 majestic live oaks, this 2,800-sq-ft heated home (4,139 total under roof) is a masterpiece of design and efficiency.The interior impresses with soaring ceilings, 8-foot solid core doors, custom crown molding, and engineered wood floors. The open living area, anchored by a gas fireplace, flows seamlessly to a screened porch overlooking the tranquil marsh.The gourmet kitchen is an entertainer's dream, featuring stunning quartzite countertops, Thermadore panel-ready appliances, and an island ice maker. A separate scullery with a beverage fridge and drawer microwave adds ultimate convenience.Retreat to the main-floor primary suite, offering a spa-like bath and an extraordinary 146-sq-ft custom walk-in closet with pocket door access to the large laundry room. Every bedroom includes a custom walk-in closet. A massive finished room over the oversized 2-car garage serves as a private fourth bedroom or guest suite, complete with a full bath.Built for resilience, the home is fortified with impact windows, full encapsulated spray foam, and a high-efficiency Trane 17 Seer HVAC system.This property is your invitation to the exclusive Callawassie Island lifestyle. As SC's first "Community Wildlife Habitat," residents enjoy world-class amenities, including 27-hole Tom Fazio championship golf course, two clubhouses and six har-tru tennis courts, pools, a fitness center, and pickleball courts, water docks for boating, fishing, and kayaking.All this is just minutes from Beaufort, Bluffton, and Hilton Head. Experience meticulous craftsmanship in a serene setting. Currently under construction with an expected finish in January 2026, offering the opportunity to enjoy a brand new Lowcountry home in the new year. OSCREA

4 Chechessee Circle, Okatie

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

$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.

$940,000
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.

$875,000
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.

$1,575,000
4 Beds ⋅ 5 Baths ⋅ 3,570 SqFt. ⋅ HILTONHEAD-504079 MLS
Designed for elevated coastal living and effortless entertaining, this custom residence is a masterclass in craftsmanship, scale, and thoughtful design. At its heart, a spectacular 21' x 41' Great Room seamlessly unites the living, dining, and kitchen spaces beneath a vaulted, beamed ceiling anchored by a gas fireplace. A dramatic 16-foot fully openable Andersen folding glass door dissolves the boundary between indoors and out, opening to a screened porch perfectly level with the main living space to create a true indoor-outdoor great room experience.The professional-caliber kitchen is both stunning and functional, centered around an expansive 9' island and outfitted with a full suite of Thermador appliances, including a refrigerator/freezer, double wall ovens, gas cooktop, drawer microwave, and dishwasher. Quartz countertops, a custom-built hood, designer tile backsplash, and a walk-in pantry elevate the space, while a dedicated wine refrigerator and sliding pass-through window provide seamless service to the outdoor grilling area.The screened porch itself is a showpiece, featuring retractable Phantom screens for unobstructed views, a vaulted ceiling, and a gas fireplace with a 200-year-old reclaimed barn mantel. Just beyond, the outdoor grill area includes a gas connection and stone counters for effortless entertaining.A private study sits behind frosted glass pocket doors, highlighted by a tray ceiling and shiplap red oak accent wall. The primary suite is a serene retreat, offering a tray ceiling, private terrace with sweeping sunrise views over the golf course, dual walk-in closets with custom built-ins, and a spa-inspired bath with soaking tub, dual vanities, and an oversized tiled shower.Two spacious first-floor guest suites, each accommodating king beds and featuring ensuite baths and shiplap accents, are thoughtfully separated for privacy. A well-appointed laundry room, owners' entrance, and oversized three-car garage with EV charging complete the main level. Upstairs, a large bonus room with private bath offers flexible living space, while an exceptional 500-square-foot conditioned storage room provides rare, full-height versatility. Additional features include, spray foam insulation, premium Andersen windows, wide-plank French oak floors, whole-house water filtration, and multi-zone HVAC, this home delivers luxury without compromise-designed for how people truly live.

29 Island Creek Drive, Okatie

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

$2,245,000
4 Beds ⋅ 4 Baths ⋅ 3,826 SqFt. ⋅ HILTONHEAD-503140 MLS
Located at the end of coveted Tabby Point on Callawassie Island, this riverfront gem is 3,826 sqft, 4 BD/4 BA with a 2nd story flex space. A boater's paradise, this home's private dock has both a stationary pier head dock with a floating dock + a boat lift added in 2019; adjacent to the Colleton River. The sunsets from this southwest facing property are truly something to behold. 2025 remodeled and added additional sq. ft. to the Family Room, including a new fireplace. New 2nd floor full bath. (3) HVAC's- ages 2025, 2023 & 2018. By all accounts this home maybe the highest elevation on CI and located at the confluence of the Colleton, Okatie and Chechessee Rivers.

24 Tabby Point Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,622,500
5 Beds ⋅ 5 Baths ⋅ 3,812 SqFt. ⋅ HILTONHEAD-503120 MLS
Discover Lowcountry living at its finest on highly sought-after Tabby Point. Perfectly positioned on one of Callawassie Island's larger marshfront lots, this home captures sweeping views stretching from the tranquil marsh straight to the river. Set back from the street for added privacy, it also features a very large backyard, offering space rarely found in marshfront living. Whether you're savoring a quiet morning coffee or hosting at sunset, the vistas here are truly unmatched.The heart of the home is a chef's kitchen, offering extensive counterspace, abundant storage, and cabinetry that extends to the ceiling-ideal for cooking, entertaining, and everyday use. A large porch off the main living area invites you to relax outdoors while taking in the coastal scenery. Inside, a stunning custom oyster shell fireplace with a reclaimed mantle and matching shelves serves as a true focal point, adding warmth and Lowcountry character. The home also features a unique in-wall aquarium that can be enjoyed from two rooms, creating a beautiful and calming visual connection throughout the living space.The main level includes a spacious guest suite featuring a jacuzzi tub and walk-in closet, providing privacy and comfort for visitors. Upstairs, the primary suite becomes a private retreat with its own screened-in balcony overlooking the marsh-a peaceful place to unwind and enjoy the breezes. A convenient kitchenette is also located on the second floor, offering added comfort and functionality for the primary suite and upper-level living.This home offers exceptional flexibility with laundry rooms on both levels; the downstairs laundry space can also serve as a wine room or back kitchen depending on your needs. Ample storage runs throughout the property.Outside, enjoy a firepit area and a floating dock perfect for launching kayaks or paddleboards, allowing effortless access to the surrounding waterways right from your backyard. A 2-car garage plus an oversized golf cart garage ensures plenty of room for vehicles, recreational gear, and workshop space.With its rare lot size, elevated views, and thoughtful layout, this home delivers an exceptional island lifestyle paired with the comforts of country club living. Callawassie Island amenities include 2 pools, 2 deep-water docks, 2 community kayak/crabbing docks, pickleball, tennis, bocce, 27 holes of championship golf, multiple dining options, and a fully equipped fitness center.Owner is a SCREA.

1 Tabby Point Lane, Okatie

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

$1,395,000
4 Beds ⋅ 4 Baths ⋅ 2,860 SqFt. ⋅ HILTONHEAD-501726 MLS
Newly completed 4 Bedroom/3.5 Bath, Callawassie Island Club Cottage, located on the Dogwood 4th hole. 1st Floor 4th Bedroom could be a Study as an option. 2nd floor with a large Media Room, Bedroom/Full Bath and covered porch/veranda to enjoy the elevated golf views. Additional unfinished FROG space is ideal for expansion or Private Suite. The Club Cottage Section offers a unique opportunity, within Callawassie Island, for a Primary Home or Investment Rental Property (overnight stay to long term rental flexibility). Discover the natural beauty of South Carolina's 1st Certified Wildlife Habitat Community- Callawassie Island. All 27 Holes of Tom Fazio Designed golf were completely renovated.( Golf is optional).

27 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,415,000
5 Beds ⋅ 6 Baths ⋅ 4,193 SqFt. ⋅ HILTONHEAD-501620 MLS
Welcome to Callawassie Island, a private gated wildlife sanctuary community. Drive across the causeway and enjoy the tidal marsh with Spartina grass, exquisite waterfowl, and occasionally playful dolphins. Enter the island with Spanish moss draped trees and world class golf views. Arrive at 3 Woodstork Watch, an estate-style home situated on one of the most beautiful and private homesites in the Lowcountry. This one-of-a-kind location with two lots combined for a 1+ acre site (POA Fees Assessed on only one lot) has 372' of road frontage and 347' on the pond with added privacy from adjacent open space area. Step outside to the beautiful porch featuring views of the pond and saltmarsh and from many vantage points throughout the property ideal for morning coffee and evening sunsets. Enjoy entertaining in your gracious great room with fireplace, large wet bar, chef's delight kitchen with 2 ovens, large island, and new appliances. Choose dining inside surrounded by tall windows or on the large porch where you'll eat outside, both with awesome views. Relax in your primary suite on the main floor with tall windows for observing wildlife. Upstairs the large balcony captures a stunning 270-degree panoramic view of the pond, marsh, fountain, winding path and treetops of magnolias, pines, oaks, and palm trees. Your family and guests will appreciate the view from the gathering/entertainment room and en-suite bedrooms with bay windows. One of the greatest advantages of this estate is its flexibility for multigenerational living, offering the ability for family and guests to enjoy privacy without sacrificing togetherness. The carriage house with separate living space over the garage creates an ideal setup for extended family, long-term guests, live-in caretakers, or a private retreat for children and grandchildren, a sought-after feature in luxury Lowcountry living. Downstairs walk through a breezeway covered stairs or on a fern and flower basket lined ramp to your carriage house. Plenty of space on your double lot to expand the main structure or add additional guest house. 372 feet of street frontage. Callawassie Island lifestyle includes for your pleasure 27 holes of golf, 2 pools, 2 clubhouses, tennis, pickle ball, fitness center, docks on the river, butterfly garden, dog park and vibrant community. Above all, what makes this home truly special is its estate setting - the rare, one-of-a-kind property on the island and unmatched privacy and views that come with it.

3 Woodstork Watch, Okatie

Listing courtesy of William Raveis - Carolina LLC.

$699,000
4 Beds ⋅ 4 Baths ⋅ 2,864 SqFt. ⋅ HILTONHEAD-500795 MLS
Opportunity awaits, offering superior value in one of the most well thought out homes available now, offering impeccable functionality, multiple upgrades, long views & pride in ownership throughout! Just a few of the upgrades: hardwood floor coverings, custom built plantation shutters with window tint for your privacy, open floor plan & 3 bedrooms. The bonus room with kitchenette & full bath further offer flexibility and/or ample room for guests. 15 Longwood also offers great peace of mind with newer architectural roof & HVAC Unit bluetooth enabled with Dehumidifier. In addition, 15LD is conveniently located on a quiet cul-de-sac only steps from the new Amenity Center, MainClubhouse, Fitness Center, Pickleball/Tennis Courts & Golf Practice Facility & situated on Magnolia #One Fairway! Callawassie Island is considered by many as the best location in Beaufort County.

15 Longwood Drive, Okatie

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

$1,075,000
4 Beds ⋅ 5 Baths ⋅ 3,460 SqFt. ⋅ HILTONHEAD-500696 MLS
Situated with a panoramic view of the golf course, this Lowcountry style custom home is surrounded by majestic oaks & blooming magnolias. Home has a large primary suite and two bedrooms on the first floor. A finished suite over the garage offers privacy and comfort for guests. A charming screened porch provides an escape to relax or for entertaining. Home is detailed with Andersen windows, reclaimed pine floors, and custom cabinetry. Freshly painted throughout. Renovated kitchen with adjacent breakfast area and family room. New paver patio and built in grill. Two tankless hot water heaters. HVAC 2017 main house. 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.

56 Spring Island Drive, Okatie

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

$1,100,000
4 Beds ⋅ 4 Baths ⋅ 2,988 SqFt. ⋅ HILTONHEAD-453932 MLS
This exquisitely renovated Lowcountry home embodies the essence of Southern charm, offering breathtaking views at every turn.  Inside a thoughtfully reimagined kitchen opens to the main living space, complimented by three spacious bedrooms, three baths and office.  Step onto your wraparound porch and relax in the shade of a majestic live oak while soaking in endless golf course vistas.  A highly sought after private suite above the garage includes its own lanai and is the perfect getaway for friends.  Callawassie Island’s clubhouse and premier amenities are just steps from your front door.

13 Longwood Drive, Okatie

Listing courtesy of William Raveis - Carolina LLC. Selling Office: Charter One Realty.

$1,450,000
5 Beds ⋅ 4 Baths ⋅ 4,712 SqFt. ⋅ HILTONHEAD-452567 MLS
Experience Lowcountry living at its finest in this beautifully updated waterfront home on Callawassie Island. With 4+ bedrooms and a 3+ car garage, there’s room for everyone and everything. Fresh new stucco adds timeless appeal, while panoramic views of the Colleton River and its marshes set a stunning scene. Enjoy the ever-changing tides and wildlife - including dolphins playing just beyond your backyard. This is more than a home - it’s a front-row seat to nature’s splendor in one of Bluffton’s most treasured communities.

15 Tabby Point Lane, Okatie

Listing courtesy of Charter One Realty.

$905,000
4 Beds ⋅ 4 Baths ⋅ 2,850 SqFt. ⋅ HILTONHEAD-451610 MLS
Single level living with Coquina stucco siding has amazing unobstructed view of Lagoon, golf as well as the marsh at a distance, beautiful live oaks. 3 bedrooms, all with private baths (renovated in 2014). 2 car garage, golf cart garage with finished room upstairs with full bath. Large Carolina room that has hurricane windows. Trex deck. New roof & newer HVAC. Paver patio & built in fire pit. Circular paver driveway. Spray foam insulation in attic. Private gated Island Community - Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated security.

9 Longwood Court, Okatie

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

$900,000
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.

$650,000
4 Beds ⋅ 3 Baths ⋅ 3,300 SqFt. ⋅ HILTONHEAD-451662 MLS
This beautifully maintained home is the ideal retreat with stunning views of the recently renovated golf course. The open and spacious layout is perfect for both everyday living and entertaining, with plenty of natural light and a thoughtful design.The expansive bonus room is a standout feature, offering endless possibilities- a home theater, game room, or extra living space. The home also includes a dedicated home management space, perfect for working from home or staying organized.Brand new roof and new HVAC.This home is ready to move in and start enjoying.

67 Winding Oak Drive, Okatie

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

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