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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.

$850,000
3 Beds ⋅ 4 Baths ⋅ 2,933 SqFt. ⋅ HILTONHEAD-512227 MLS
Welcome to this beautifully maintained 3-bedroom, 4-bath home with 2,933 square feet in the prestigious gated community of Callawassie Island. Lovingly cared for by its original owner, this inviting home offers timeless quality, generous living spaces, and a beautiful golf-course setting. Inside 12-foot ceilings and high-quality Pella windows and doors create a bright, open atmosphere. The updated kitchen provides a stylish and functional gathering space, while the first-floor primary suite offers privacy and convenience. The second floor features a comfortable guest suite, creating an ideal retreat for family and friends. A large dedicated sewing room provides exceptional space for quilting, crafting, hobbies, or creative pursuits. The home has been thoughtfully maintained, including a roof and new dormers in 2016. The oversized garage provides abundant storage and parking space, including room for a golf cart-perfect for enjoying the Callawassie Island lifestyle.

28 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$899,000
3 Beds ⋅ 3 Baths ⋅ 2,115 SqFt. ⋅ HILTONHEAD-512221 MLS
Better than new and truly one-of-a-kind, this artisan-crafted former model home offers an exceptional blend of luxury, privacy, and Lowcountry living. Located in the desirable Oyster Cay on Callawassie Island, tucked away on an oversized, serene wooded lot, the residence feels exceptionally peaceful and private while being just down the street from the River Club, Family pool and deep-water boat docks. Thoughtfully designed and meticulously maintained, the home showcases an impressive collection of custom upgrades and designer finishes, including multiple shiplap accent walls, an extensive custom trim package, Hunter Douglas shades, a tankless water heater, and spray foam insulation, along with countless other refined details. An indoor gas fireplace creates a warm and inviting gathering space, while the spacious screened porch, with its inviting outdoor gas fireplace provides a beautiful year-round setting for relaxing, dining, and enjoying the tranquil natural surroundings. Everyday comfort and convenience have been equally considered, with a whole-home generator and EV charger providing modern functionality and peace of mind. The spacious floor plan, elevated craftsmanship, and impeccable model-home presentation make this residence feel almost new-yet it already includes the custom upgrades and finishing touches that are typically added over time. Beyond the home, Callawassie Island offers an exceptional Lowcountry lifestyle, with Tom Fazio-designed golf, tennis, pickleball, pools, a fitness center, boating, and more, all set within a beautiful private island environment. Ideally located in Beaufort County, the community provides convenient access to Beaufort, Port Royal, Bluffton, Hilton Head Island, Charleston and Savannah, while preserving the privacy, natural beauty, and tranquility that make island living so special.

226 Callawassie 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.

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

89 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,395,000
3 Beds ⋅ 3 Baths ⋅ 3,549 SqFt. ⋅ HILTONHEAD-508583 MLS
Exceptional custom-built home showcasing unique golf and lagoon views across the entire Magnolia #5 hole on Callawassie Island's beautifully renovated Tom Fazio course. Thoughtfully designed to embrace its stunning setting, this move-in-ready residence offers the perfect opportunity to begin enjoying Lowcountry island living from day one.The open-concept floor plan is filled with natural light, highlighted by soaring ceilings, expansive windows, and generous crown molding throughout. Refinished and stained heart pine floors add warmth and character, while the Great Room features a fireplace and custom built-ins, creating an inviting space for everyday living and entertaining.The gourmet kitchen is beautifully appointed with all newer (2024) Thermador stainless steel appliances, a six-burner gas cooktop, granite countertops, and distinctive Italian glazed cabinetry. The primary suite serves as a private retreat with elegant marble and porcelain tile finishes and a custom-designed closet.Recent improvements provide exceptional value and peace of mind, including all three HVAC systems replaced in 2024, newer washer and dryer, refinished heart pine flooring, refinished mahogany front door, and three new garage door openers. Upper-level furnishings may convey with limited exclusions, creating a turnkey opportunity for the next owner.Outdoor living is equally impressive, with a spacious deck and screened porch perfectly positioned to capture panoramic golf and lagoon views, cooling marsh breezes, and unforgettable sunsets. Whether enjoying a quiet morning coffee or entertaining friends after a day on the course, these spaces embody the best of Lowcountry living.Beyond the home, Callawassie Island offers an unmatched private island lifestyle with 27 holes of championship golf, deep-water docks, two clubhouses, fitness and wellness facilities, tennis, pickleball, swimming pools, walking trails, and a vibrant social atmosphere-all within a gated island community surrounded by breathtaking natural beauty.This is more than a home; it's an opportunity to embrace one of the Lowcountry's most sought-after island lifestyles.

113 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,100,000
3 Beds ⋅ 4 Baths ⋅ 3,148 SqFt. ⋅ HILTONHEAD-509010 MLS
Incredible riverfront opportunity with breathtaking long-range views of tidal marsh to the Colleton River. Enjoy generous outdoor entertaining areas and an incredible 180-degree panoramic view. The spacious 15' x 12' viewing deck provides the perfect place to gather with friends, watch the changing tides, and take in spectacular sunsets and coastal breezes. Nestled on a private 1.29-acre cul-de-sac lot, the property offers a desirable one-level floor plan with 3,292 square feet, 3 bedrooms, and 3.5 baths. Situated on high ground within an X-500 flood zone, this home awaits a new owner's vision to transform it into a truly exceptional waterfront retreat. Recent improvements include two new HVAC systems (2025) and a roof installed in 2016. Private dock potential exists, subject to current permitting requirements and approvals. A truly special setting offering privacy, deep-water views, and the opportunity to create your dream Lowcountry waterfront lifestyle. 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. Seller to provide buyer with a $75,000 Credit, at closing, towards repairs, re-piping or Contribution Fee, with an acceptable offer.

5 Shellfish Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$385,000
3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-509585 MLS
Nestled within the private gated community of Callawassie Island, 24 Heron Walk offers Lowcountry living at its finest. This beautifully maintained 3-bedroom, 2-bath townhome features stunning lagoon views from both the front and back, along with picturesque golf course views. The remodeled 2023 kitchen is a true showpiece, highlighted by a premium Hallman Cookers professional range imported from Italy. Enjoy cozy evenings by the wood-burning fireplace and the peaceful natural surroundings that make this home so special. Residents enjoy exceptional amenities including 3 upgraded golf courses with over $8 million in recent improvements, two clubhouses, two restaurants, two pools, new pickleball courts, croquet and bocce ball, massage and therapy rooms, a library, boat docks, and separate dog parks for large and small dogs. Seller offering $52,000 towards Callawassie Island buy-in.

24 Heron Walk, Okatie

Listing courtesy of ERA Southeast Coastal.

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

20 Heron Walk, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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.

$1,285,000
3 Beds ⋅ 4 Baths ⋅ 3,512 SqFt. ⋅ HILTONHEAD-508587 MLS
Nestled within one of the most scenic settings on Callawassie Island, this exceptional custom-built Lowcountry home captures miles of sweeping marsh, river, and golf views, all paired with incredible sunsets and refreshing summer breezes. Thoughtfully designed to embrace its stunning surroundings, the home offers expansive porches and decks that create a seamless indoor-outdoor living experience. Crafted with timeless quality and architectural character throughout, features include a lifetime metal roof, 10-foot ceilings, Pella windows and doors, reclaimed Southern pine flooring, 8-foot solid core doors, and extensive custom cabinetry and built-ins. The beautifully appointed designer kitchen showcases limestone and granite countertops, a gas cooktop, and refined finishes ideal for both everyday living and entertaining. Additional details such as crown molding throughout the first floor and oil enamel painted casework and doors further elevate the home's craftsmanship and warmth. The spacious second-floor bedroom retreat includes a private sitting room, while the detached garage offers a beautifully designed guest suite complete with its own kitchenette-ideal for visitors, multigenerational living, or private workspace flexibility. Residents enjoy the unmatched lifestyle of Callawassie Island-a private gated island community known for its remarkable natural beauty, welcoming atmosphere, deep-water access, top-tier golf and amenities (optional), endless outdoor recreation, and the peaceful charm of true Lowcountry living.

10 Island Creek Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$879,000
3 Beds ⋅ 4 Baths ⋅ 2,722 SqFt. ⋅ HILTONHEAD-508619 MLS
Beautifully renovated Lowcountry home located in a private gated community of Callawassie Island, offering the perfect blend of timeless Southern charm and modern updates. This 3-bedroom, 3 1/2 bath residence has been thoughtfully updated over the last 4 years with attention to both style and functionality. Inside, you'll find spacious living areas, updated finishes, and a flowing floor plan designed for comfortable everyday living and entertaining alike. Each bedroom offers its own en suite bath, while the additional half bath adds convenience for guests. Enjoy the character and warmth of classic Lowcountry architecture paired with the peace of mind that comes from recent renovations. Plantation shutters, 6 burner gas stove with double ovens. Nestled within a gated community, this home provides privacy, security, and a relaxed coastal lifestyle close to everything the Lowcountry has to offer. Callawassie Island is a private gated Island Community that offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

83 Osprey Circle, Okatie

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

$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.

$395,000
HILTONHEAD-505366 MLS
Discover the perfect canvas for your coastal retreat on this exceptional .93-acre homesite with views of the Colleton River. Nestled in the serene enclave of Callawassie Island, this property offers a rare opportunity to design and build your dream custom home in a private island community. Ideally positioned between Beaufort, Bluffton and Hilton Head, Callawassie Island seamlessly blends privacy, natural beauty, and convenient access to the Lowcountry's finest offerings. Immerse yourself in a lifestyle of recreation and leisure with the island's 27-hole Tom Fazio golf course, elegant Clubhouse, and the scenic River House overlooking tidal waters. Residents enjoy exclusive amenities including community docks, two resort-style swimming pools, a fully equipped fitness center, and abundant opportunities for kayaking, tennis, and pickleball. The property features an existing dock that requires repairs. Once restored, you will have access to water to explore the tidal creeks and waterways. With nearly an acre of privacy, towering oaks, and tranquil surroundings, this homesite is the ideal setting to create a residence that captures the essence of Lowcountry elegance. Experience the coastal lifestyle you have always dreamed of, where nature, recreation, and refined living converge in perfect harmony. Build your vision and make Callawassie Island home.

21 River Bend Drive, Okatie

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$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.

$725,000
3 Beds ⋅ 4 Baths ⋅ 2,580 SqFt. ⋅ HILTONHEAD-504968 MLS
Experience the romance of Lowcountry living on Callawassie Island. Tucked beneath towering pines on a quiet, private homesite, this 2,580 sq ft home offers 3BR/3BA plus a dedicated office and captivating lagoon-to-golf views. A classic brick stairway leads to an expansive, columned front porch-rocking-chair ready and cooled by ceiling fans-setting the tone for slow mornings, sweet tea afternoons, and sunset conversations. Inside, enjoy light-filled living spaces and a gourmet kitchen built for gathering, featuring custom cabinetry, stainless appliances, a professional-style gas range with statement hood, and an oversized granite island with sink and abundant storage. The spacious primary suite is a true retreat with tranquil views and a spa-inspired bath with dual vanity, soaking tub, and separate shower. Two additional bedrooms and baths provide comfort and flexibility for guests. Out back, the screened porch and patio deliver the quintessential Lowcountry backdrop-breezes through the trees, birdsong overhead, and front-row vistas across the lagoon to the fairway beyond. Callawassie Island's gated community elevates the lifestyle with an exceptional club experience, including golf, tennis, fitness, pool, dining, and miles of protected marsh and waterways.

64 Osprey Circle, Okatie

Listing courtesy of Charter One Realty.

$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.

$459,000
HILTONHEAD-503416 MLS
Rarely does an opportunity arise to own one of the most significant waterfront parcels in the Lowcountry. This exceptional 1.15-acre homesite on Callawassie Island represents one of the largest available properties in this award-winning 880-acre private community. Situated with wide-open northeastern exposure, the site captures breathtaking sunrises across shimmering tidal creeks and vibrant salt marshes. Surrounded by centuries-old live oaks and Spanish moss, the landscape provides a timeless backdrop for a legacy estate. Callawassie Island offers a premier Lowcountry lifestyle centered on 27 holes of Tom Fazio-designed golf, professional-grade racquet facilities, and dual clubhouses that provide deepwater access and luxury wellness amenities within South Carolina's first certified Community Wildlife Habitat. Strategically situated in the heart of Beaufort County, Callawassie Island is almost equidistant from the historic charm of Beaufort and the bustling center of Bluffton, placing residents within a 35-minute drive of Hilton Head Island, Savannah, Georgia, and the Savannah/Hilton Head International Airport.

32 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$700,000
3 Beds ⋅ 3 Baths ⋅ 3,250 SqFt. ⋅ HILTONHEAD-503938 MLS
Enjoy the stunning views of Magnolia 5 fairway and ponds. Huge vaulted screened porch with fireplace. Primary bedroom on first floor with den adjacent.. Large great room with cathedral ceilings with fireplace. Upstairs is a sitting room with two bedrooms that have a jack and jill bath as well as a finished room over garage. Newer roof & HVAC. 2 tankless propane hot water heaters. New plumbing and many new windows. Private gated Island community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock, 6 tennis courts, Pickleball courts, 27 hole golf course, dog park, bocce courts & 24/7 gated security

91 Winding Oak Drive, Okatie

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

$639,000
3 Beds ⋅ 3 Baths ⋅ 2,124 SqFt. ⋅ HILTONHEAD-502292 MLS
Enjoy the Callawassie Island Lifestyle, within the popular Club Cottage Section, as a Primary Home or 2nd Home with rental/investment potential. Ideally located within a short walk to Tennis, Tennis Pro-Shop & Pickleball Courts, Fitness Facility, Pool, Main Clubhouse, Golf Pro Shop and Golf Practice Facility. This well-conditioned home, with an open floor plan, exudes comfort and functionality. Tranquil pond and private Golf views of the Dogwood #1 hole. All piping replaced 2025. Callawassie Island offers an amazing community of kind people, breathtaking natural beauty, endless activities, top notch golf with total privacy and security. Furnishings are negotiable.

50 Callawassie Club Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$690,000
3 Beds ⋅ 3 Baths ⋅ 2,230 SqFt. ⋅ HILTONHEAD-503102 MLS
Discover this spacious 3-bedroom, 3-bath, 2,230 sq. ft., Club Cottage on Callawassie Island, offering single-story living with an open floor plan, a 2-car garage, and serene views along the first fairway of the Dogwood Course. Being sold fully furnished-including all kitchenware and appliances-except for artwork. Perfect as a primary home, getaway, or short-term rental. The heart of the community is the Tom Fazio-designed 27-hole golf course, complemented by tennis courts, pickleball, fitness facilities, two swimming pools, and a clubhouse for dining and social gatherings. The River Club also offers fantastic river views, a swimming pool, and additional dining options. Residents enjoy deep-water access from the community docks, making Callawassie Island an ideal destination for boating, kayaking, and fishing. Callawassie Island, South Carolina, is a private, gated island community located between Bluffton and Beaufort, and just about 30 minutes from Hilton Head Island and Savannah. It offers the perfect balance of quiet, natural living with convenient access to culture, dining, and shopping. The island is known for its natural beauty, with more than 880 acres of maritime forest, salt marshes, tidal creeks, and deep-water access to the Colleton and Okatie Rivers. Designated as a Certified Community Wildlife Habitat, Callawassie Island emphasizes conservation and harmonious coexistence with nature.

45 Callawassie Club Drive, Okatie

Listing courtesy of EXP Realty LLC. Selling Office: Greco Group Brokered by eXp Realty.

$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.

$1,050,000
3 Beds ⋅ 3 Baths ⋅ 2,406 SqFt. ⋅ HILTONHEAD-502817 MLS
Welcome to luxurious Lowcountry living in this stunning brand-new construction home by Artisan Custom Homes located on the serene and sought-after Callawassie Island. Thoughtfully designed to blend modern comfort with timeless coastal charm, this residence offers an exceptional lifestyle surrounded by natural beauty, world-class amenities, and the relaxed elegance of island living. Set on the quiet, picturesque Osprey Circle, the home welcomes you with sweeping views of mature live oaks, palmettos, and the island's protected natural landscape. Step inside to an open and airy floor plan featuring high ceilings, abundant natural light, and refined architectural details throughout. Expansive living and dining spaces flow effortlessly into a chef-inspired kitchen-ideal for both everyday enjoyment and effortless entertaining. The primary suite provides a peaceful retreat with spa-style comforts and tranquil views, while additional guest rooms offer privacy and flexibility for family or visitors. Outdoor living shines with a spacious screened porch with fireplace, perfect for morning coffee, evening breezes, or simply enjoying the island's abundant wildlife. Callawassie Island is renowned for its unmatched lifestyle-27 holes of Tom Fazio golf, top-tier tennis and pickleball facilities, two resort-style pools, deep-water docks, a state-of-the-art fitness center, and vibrant community events. With 24-hour security and breathtaking riverfront scenery, it's a place where nature, community, and luxury come together. This exceptional new home at 67 Osprey Circle offers the rare opportunity to experience the best of coastal South Carolina in a brand-new, move-in-ready residence.

67 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Peirce Group Brokered by EXP Realty LLC.

$849,000
3 Beds ⋅ 3 Baths ⋅ 2,925 SqFt. ⋅ HILTONHEAD-502830 MLS
Enjoy amazing sunsets from almost every room of this marsh front home. One level home with primary bedroom on one side and 2 bedrooms on the opposite side with a jack and jill bathroom. Double sided fireplace in family room and screen porch. This home offers living room, dining room, eatin kitchen, family room and Office/library for your enjoyment. 2 car garage and golf cart garage. This private gated Island Community offers Clubhouse, River Club , fitness center, 2 pools, kayak dock. Six Har-Tru Tennis courts, bocce courts, pickleball courts, dog park, 27 holes of Tom Fazio designed Golf courses and 24/7 gated security.

25 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$500,000
3 Beds ⋅ 3 Baths ⋅ 2,398 SqFt. ⋅ HILTONHEAD-502567 MLS
Welcome to Callawassie Island, a private gated island sanctuary community with numerous amenities. With a new roof, this spacious 3 bedroom, 2.5 bath one level is perfectly framed by sweeping views of Spanish moss-draped oaks and the Tom Fazio "Palmetto" course. Sunlight filters through generous windows, illuminating architectural details. With vaulted ceilings and a wall of windows, the inviting great room is anchored by the fireplace. Entertaining is easy with the spacious dining area open to the kitchen. The kitchen showcases custom wooden cabinetry and a walk-in pantry. The tranquil primary suite overlooks the wide views and offers a jetted spa tub, walk-in shower and dual vanities. A large two car garage with a dedicated golf cart bay, this home is priced for you to add your personal touches.

9 Winding Oak Drive, Okatie

Listing courtesy of Keller Williams Realty. Selling Office: William Raveis - Carolina LLC.

$450,000
3 Beds ⋅ 2 Baths ⋅ 1,861 SqFt. ⋅ HILTONHEAD-502715 MLS
26 Heron Walk stands out as one of the largest villas in the Village section, offering 1,861 sq ft of thoughtfully designed living space. This inviting home features a large Carolina Room and a detached full garage with golf-cart bay. Designed for comfort and flexibility, it offers open living areas and exceptional privacy with serene lagoon and golf-course views. Upstairs, the beautifully updated second-story bath has been used as a primary suite during current ownership, enhancing the home's versatility and livability. New Roof-2026. Located within the private, gated community of Callawassie Island, residents enjoy access to newly renovated Tom Fazio-designed golf courses, deep-water access, club dining, fitness facilities, pools, tennis, pickleball, bocce, and more. Life on Callawassie Island offers an unmatched blend of natural beauty, community connection, and the timeless charm of Lowcountry living.

26 Heron Walk, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,195,000
3 Beds ⋅ 4 Baths ⋅ 2,943 SqFt. ⋅ HILTONHEAD-502086 MLS
No need to wait to build your dream home. Move right into this better than new custom low country style marsh front home. Primary bedroom on first floor. Upstairs has media room and Two bedrooms with private baths as well as an outside veranda. Large screened porch. Unfinished area over two car garage and golf cart garage for future space. Outdoor grill and hot tub. Thermador appliances. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

4 Mayon Point, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

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