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.

$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.

$1,379,000

3 Beds ⋅ 3 Baths ⋅ 2,462 SqFt. ⋅ HILTONHEAD-512149 MLS

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

90 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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.

$1,350,000

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.

$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.

$799,000

3 Beds ⋅ 3 Baths ⋅ 2,108 SqFt. ⋅ HILTONHEAD-510356 MLS

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

13 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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.

$1,899,900

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.

$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.

$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.

$975,000

3 Beds ⋅ 4 Baths ⋅ 2,826 SqFt. ⋅ HILTONHEAD-508314 MLS

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

14 Links Drive, Okatie

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

$865,000

3 Beds ⋅ 3 Baths ⋅ 2,303 SqFt. ⋅ HILTONHEAD-507814 MLS

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

5 Oyster Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$798,000

3 Beds ⋅ 3 Baths ⋅ 2,591 SqFt. ⋅ HILTONHEAD-507892 MLS

Located on desirable Osprey Circle, this beautifully maintained, single-level 3-bedroom home offers a move-in ready opportunity with thoughtful renovations throughout. Set among native hardwoods, magnolias, and palms, the property captures a true sense of serenity, enhanced by manicured gardens, natural surroundings, and great elevation-creating a setting that feels like a private retreat. The kitchen was fully renovated in 2025 and features new appliances, a custom-designed hood, large wine cooler, and an added coffee bar and pantry area, creating a functional and elevated space for both everyday living and entertaining. Interior updates include new paint, updated lighting fixtures throughout, new toilets, and new flooring in select areas. Additional improvements include a new vanity in the half bath (2024), a newly added second bathroom, an Aquasana water filtration system, and an LG washer/dryer tower.Outdoor living has been significantly enhanced with a new screened porch (2024), approximately 15.5 x 15.5, ideal for relaxing or entertaining. The exterior also features an enhanced front entry with added pavers, patio upgrades, expanded outdoor living space, and a newly designed backyard with all new plantings for increased privacy. A new driveway, refreshed landscaping, and irrigation updates complete the setting.This home offers a rare combination of quality updates, easy one-level living, and a prime location within Callawassie Island-perfect for those seeking both comfort and connection to the natural beauty of the Lowcountry.

15 Osprey Circle, Bluffton

Listing courtesy of Coastal Real Estate Solutions II.

$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.

$1,399,999

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.

$835,000

3 Beds ⋅ 4 Baths ⋅ 2,772 SqFt. ⋅ HILTONHEAD-506039 MLS

BRAND NEW ROOF on this completely renovated move-in ready, single-story Lowcountry home offering breathtaking marsh-to-Colleton River views. Thoughtfully designed for both comfort and versatility, the home is a true boater's retreat, situated just steps from the River Club, community boat docks while featuring an expansive, partially finished ground-level garage with space for up to four vehicles, a boat, abundant storage, and endless potential for your customization. Upon entering the foyer, the home's exceptional craftsmanship is immediately apparent. The upgraded kitchen, complete with stainless steel appliances, flows seamlessly into the inviting family room, highlighted by a beautiful fireplace and large windows that perfectly frame the stunning waterfront scenery. The thoughtfully designed split floor plan enhances privacy and livability, with refinished hardwood floors throughout and generously sized bedrooms, each with its own en suite bath. Situated on an oversized 0.9-acre lot adjacent to the CI Butterfly Garden, this property offers a rare combination of serenity, space, and scenic beauty-an ideal Lowcountry retreat. Callawassie Island is Considered by many as the best location in Beaufort County!

2 S Oak Forest Drive, Okatie

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

$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.

$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.

$699,900

3 Beds ⋅ 4 Baths ⋅ 2,867 SqFt. ⋅ HILTONHEAD-503347 MLS

This home now represents one of the finest values on Callawassie Island, granting a buyer flexibility to improve and elevate the property to their liking. Boasting phenomenal views of the newly renovated Tom Fazio Magnolia course Hole 3 green. An entertainers' dream home with an ample kitchen and luxurious wet bar with custom built-ins is the icing on the cake for this gem! Further detailed by a grand office, dining room, fireplace, and generously sized primary bedroom. An additional bedroom and full bedroom with bathroom over the garage complete the property. Natural light abounds with soaring cathedral and tray ceilings as well as oversized windows. Take pride in living in South Carolina's first certified Wildlife Habitat Community.

49 Winding Oak Drive, Okatie

Listing courtesy of Charter One 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.

$750,000

3 Beds ⋅ 3 Baths ⋅ 2,104 SqFt. ⋅ HILTONHEAD-502751 MLS

Ideally located midway between Beaufort and Bluffton, this furnished, move-in ready Callawassie Island home was originally renovated in 2020 and thoughtfully improved again in 2025. Filled with natural light, it offers peaceful views of the Palmetto #4 green on the newly renovated Tom Fazio-designed course.The kitchen features VIKING stainless steel appliances, while a spacious screened porch creates an easy, inviting flow for everyday living and entertaining. A 2023 roof and Wi-Fi-enabled water heater add efficiency and peace of mind.Recent interior updates include solid wood closet shelving, new LED lighting, fresh interior paint, a whole-home audio system, four mounted TVs, and six Ring cameras. The foundation was reinforced with new footer supports in 2024 and passed follow-up inspection with no issues, with all prior inspection items addressed.Exterior improvements include freshly painted decks, stairs, and railings. Callawassie Island residents enjoy golf, deep-water docks, dining, fitness, pools, tennis, pickleball, bocce, and more.

3 Winding Oak Drive, Okatie

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

$995,000

3 Beds ⋅ 3 Baths ⋅ 2,435 SqFt. ⋅ HILTONHEAD-502431 MLS

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

61 Winding Oak Drive, Okatie

Listing courtesy of Coldwell Banker Access Realty.

$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.

$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.

$1,266,000

3 Beds ⋅ 4 Baths ⋅ 4,031 SqFt. ⋅ HILTONHEAD-500350 MLS

Situated on a beautiful lot with a peaceful golf/pond view, this classic Lowcountry style custom home built by Steve Tilton (Coastal Signature Homes) features soaring 12 ft. ceilings throughout the entire first floor, elaborate molding trim package, granite kitchen counters, kitchen island with prep sink, oversized walk in pantry, Pella windows, Baldwin hardware, and incredible storage throughout. Enjoy outdoor living at its finest, with covered porches at the front and rear of the home, a gorgeous screened porch w/gas fireplace, and a new paver patio. A large 2 car garage with golf cart bay and unfinished space above for future use completes this attractive residence. Impeccably maintained, recent upgrades include new roof, new HVAC units, freshly painted exterior and mahogany exterior doors. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, Bocce courts, Dog park, 27 hole Golf course & 24/7 gated‌‌‌‌‌‌‌‌‌‌‌‌ security.

18 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Compass Carolinas, LLC.

$1,249,000

3 Beds ⋅ 3 Baths ⋅ 2,500 SqFt. ⋅ HILTONHEAD-500380 MLS

Completed in 2024, this custom Allison Ramsey-designed home sits on a 1.14-acre marshfront lot, created by consolidating part of a neighboring parcel to enhance privacy, space, and views. Designed to embrace its surroundings, the elevated home offers sweeping marsh views and a blend of Lowcountry charm and casual luxury. Built by CMS with top-tier finishes, it features approx. 2,500 sq ft, French oak floors, Andersen windows and doors, 10-foot ceilings, and a new elevator. A rare opportunity for buyers seeking a brand-new home without the time and hassle of building. The kitchen features Thermador and Bosch appliances, custom cabinetry, and a large island. Outdoor living includes a wraparound porch, tabby fireplace, gas lanterns, irrigation, and a tankless water heater.

108 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$657,500

3 Beds ⋅ 3 Baths ⋅ 2,961 SqFt. ⋅ HILTONHEAD-453990 MLS

Beautiful one-level living with an open, vaulted floor plan perfect for entertaining and enjoys gorgeous private views! This 2,961SF, 3BD, 3BA home features a spacious flex room ideal for a workshop, game room, or golf simulator. Looking to avoid steps? Don't miss the best value on Callawassie Island at $225/sf! Recent upgrades include interior/exterior paint, HVAC, flooring, kitchen appliances, and more. The outdoor living can't be beat with a vaulted screened porch, paved patio, fire pit, and grilling area. Callawassie's top-tier amenities include 24/7 security, tennis, pickleball, fitness, deep-water docks, dining, and recently renovated 27 holes of Tom Fazio golf. Come check out the Callawassie magic; it's worth the trip!

3 Longwood Court, Okatie

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

$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.

$1,930,000

3 Beds ⋅ 4 Baths ⋅ 3,789 SqFt. ⋅ HILTONHEAD-453415 MLS

No need to wait to build your dream home. Move right into this fabulous 3 year old Steve Tilton - Coastal Signature Homes home. This low country style home is on the marsh with amazing views. This home has it all. Custom Shiplap in foyer and great room. Coffer ceilings in great room and primary bedroom. Office with custom built ins. 12 foot ceilings on first floor. Large screen porch with fireplace & outdoor custom grill. large back kitchen. Huge attic space. 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 security.

62 Winding Oak Drive, Okatie

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

$950,000

3 Beds ⋅ 3 Baths ⋅ 2,882 SqFt. ⋅ HILTONHEAD-453454 MLS

One Story Living at Its Finest in one of Callawassie Island's Most Desirable Locations, thoughtfully situated on an Oversized wooded corner lot of private cul-de-sac! The New Owner will enjoy the benefit of moving right in to a Completely Updated Home Repainted Inside & Out, w Triple Crown Moldings & Transom Windows throughout w an Oversized Carolina Room. Professionally Designed New Kitchen, Bedrooms, Bathrooms & Much More! Enjoy the Serenity of Nature from Enclosed Porch, Patio & Breezeway, w front circle drive for guests & large back drive to full 3 car garage & steps from Wild Magnolia Park. PROPERTY SOLD FULLY FURNISHED!

1 Wild Magnolia Court, Okatie

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

$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.

$1,295,000

4 Beds ⋅ 5 Baths ⋅ 3,030 SqFt. ⋅ HILTONHEAD-450400 MLS

Move In Ready NEW CONSTRUCTION home by Artisan Custom Homes! Situated on a private cul-de-sac w/ views of Dogwood #6. River Place Cottage is filled with upgrades! White oak floors, beams, shiplap & more. Discover the wildlife Callawassie is known for on your screened porch w/ beautiful brick fireplace. Primary Bedroom, Study & Open Concept Kitchen/Living/Dining on the main. Plus 2 bedrooms w/ private on-suites on the 2nd & a studio w/ on-suite over the detached 2.5 car garage. Experience the unparalleled island lifestyle w/ 24/7 Security, 2 Heated/Cooled Pools, 4 Docks, 2 Clubhouses, Fitness, Tennis, Pickleball & 27 Tom Fazio golf holes.

14 Heron Point, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: The Agency Hilton Head.

$750,000

3 Beds ⋅ 3 Baths ⋅ 2,249 SqFt. ⋅ HILTONHEAD-449131 MLS

A Classic Southern Living Cottage, with functional design and craftsman quality built, set in a private wooded setting on .74 acre. Enjoy expansive golf course views from the curved, wraparound heated rear screened porch. An open chef's kitchen is the heart of this 3 bedroom, 2.5 bath cottage. High ceilings, wide plank hardwood floors throughout, featuring a Savannah brick fireplace. The private office/den,1st floor master suite, & two 2nd floor guest rooms w/spacious guest bath. Detached 2 car garage w/connecting breezeway. Spray foamed attic & crawl space. New roof 2024, both new HVAC's 2024, gas tankless water heater & generator conveys!

58 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: William Raveis - Carolina LLC.

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 3,437 SqFt. ⋅ HILTONHEAD-449580 MLS

Gorgeous views of Magnolia 2 fairway & green! First time on market! Hardwood floors throughout. Current owners finished 4th bedroom/flex room upstairs w/builtins overlooking golf course. Wrap around front porch greets friends. Main level offers study w/built ins, separate dining room, butlers pantry w/wine fridge, walk-in pantry, chef's kitchen w/induction cooktop, large island w/2nd sink, stainless appliances. 2 suites on main w/travertine floors in baths. Upstairs are 2 large bedrooms w/jack & jill bath. Detached garage offers more storage. FINISH YOUR FROG above garage! Vinyl windows installed on back porch! Much more! Agent/owner

22 Osprey Circle, Okatie

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

$2,100,000

5 Beds ⋅ 7 Baths ⋅ 5,259 SqFt. ⋅ HILTONHEAD-447631 MLS

New construction on very private lot overlooking the Colleton River with gorgeous southern exposure. Tons of space including 1st floor primary suite, light-drenched kitchen that opens to living room and breakfast nook, formal dining room and office. Second floor features 3 bedrooms with bath en suites, plus den. Huge top floor with separate bath offers great flex space with tons of creative options. Don't miss the carriage apartment located above the spacious 3-car garage. Callawassie Island is a private Sea Island gem offering extraordinary golf, deep water dock access, fitness center, racquet facilities, club house, river club and 2 pools.

7 Winding Oak Court, Okatie

Listing courtesy of William Raveis - Carolina LLC. Selling Office: Daniel Ravenel Sotheby's International Realty.

$1,500,000

4 Beds ⋅ 5 Baths ⋅ 3,600 SqFt. ⋅ HILTONHEAD-448729 MLS

Marsh-view living and dining welcome you home! The heart of this lovely home is the Thermador kitchen with custom cabinetry, walk-in pantry, oyster shell quartz island, and farm/prep sinks—perfect for any chef or entertainer. The primary suite offers marsh vistas, dual baths, walk-in closets, and a flex room perfect for private office or 5th bedroom. A split floor plan adds privacy with two 1st-floor guest bedrooms connected by a Jack-and-Jill bath. Endless options for the oversized ensuite bonus room! This is a must see home!

14 Dolphin Lane, Okatie

Listing courtesy of Charter One Realty. Selling Office: Peirce Group Brokered by EXP Realty LLC.

$1,100,000

4 Beds ⋅ 6 Baths ⋅ 4,797 SqFt. ⋅ HILTONHEAD-446975 MLS

Privacy awaits at your outdoor oasis with heated saltwater pool and outdoor kitchen. Enjoy views of Magnolia #5 green/lagoon from your elevated main living spaces, screened porch & patio. Craftsmanship can be felt the moment you walk thru the Mahogany Front doors into 14-16' ceilings with custom moldings & trim. Every bedroom has its own full bathroom, as does the large bonus/5th bedroom over the 2.5 car garage. Upgrades include new White Oak Flooring & paint throughout main floor('24), New Roof('24), Whole House Generac('23), 2 new HVACs('22), 2 new Rinnai tankless hwhs('22), new GE Cafe appliances('22), plus much more. Golf Cart Included.

109 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

$2,200,000

4 Beds ⋅ 5 Baths ⋅ 4,502 SqFt. ⋅ HILTONHEAD-447713 MLS

Capturing the essence of Lowcountry living, this extraordinary waterfront home boasts 2 pier heads, dock, float, 13,000 lb. boat lift, and desirable westerly views. Taken down to the studs in 2012, craftsmanship abounds. You'll find finishes like red oak hardwood and Savannah gray brick floors, custom millwork and cabinetry, and paneled walls and wainscoting. Keeping room, chef's kitchen, sunroom, living room, primary bedroom suite and upstairs den with porch all afford breathtaking vistas over the water and tidal marshes. All set on a lushly landscaped 1.4-acre home site, this is Callawassie Island's finest offering.

48 Sugar Mill Drive, Okatie

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

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