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$899,000

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.

4 Beds ⋅ 4 Baths ⋅ 3,587 SqFt. ⋅ HILTONHEAD-512387 MLS

This quintessential Lowcountry home offers easy one-story living amid exceptional private surroundings on Callawassie Island. Thoughtfully positioned in one of the most desirable settings, 1 S Oak Forest sits directly across from the picturesque butterfly garden and beside protected green space, creating a beautiful natural backdrop and an uncommon sense of privacy, while remaining just steps from the River Club, community pool, and boat docks. The spacious open floor plan is filled with natural light and flows into the gourmet kitchen and rear Carolina room overlooking a tranquil natural oasis. Meticulously maintained, the home features custom built-ins, plantation shutters, generously sized rooms, and a dedicated office. A charming guest suite above the garage includes a kitchenette and full bath, offering a comfortable space for guests or extended stays. Recent improvements provide added peace of mind, including a brand-new architectural roof with transferable warranty, freshly painted exterior, and two nearly new HVAC units. Callawassie Island is considered by many to be one of the best locations in Beaufort County, offering an exceptional Lowcountry lifestyle with world-class amenities, including Tom Fazio golf, waterfront clubhouses, a fitness facility, community pools, boat docks, and more. A rare combination of privacy, nature, convenience, and thoughtful updates, 1 S Oak Forest is a wonderful place to call home.

1 S Oak Forest Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,379,000

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.

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.

$1,075,000

Among the Best Golf/Marsh views within Callawassie Island. This Club Cottage, at 2,965 sq. feet, has 4 bedrooms, 3 1/2 bath and terrific long views of the complete Dogwood 9th hole, bridge/lagoon and tidal marsh views. Primary Bedroom on 1st floor, with 2 bedrooms upstairs with an optional 4th bedroom or office. The Upstairs Bedroom private veranda provides even more elevated spectacular views. Callawassie Island Club Cottage Section is ideal for either a primary home, a 2nd home or a rental investment property. Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

4 Beds ⋅ 4 Baths ⋅ 2,965 SqFt. ⋅ HILTONHEAD-511584 MLS

Among the Best Golf/Marsh views within Callawassie Island. This Club Cottage, at 2,965 sq. feet, has 4 bedrooms, 3 1/2 bath and terrific long views of the complete Dogwood 9th hole, bridge/lagoon and tidal marsh views. Primary Bedroom on 1st floor, with 2 bedrooms upstairs with an optional 4th bedroom or office. The Upstairs Bedroom private veranda provides even more elevated spectacular views. Callawassie Island Club Cottage Section is ideal for either a primary home, a 2nd home or a rental investment property. Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

24 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,050,000

Tucked at the end of a quiet cul-de-sac and shared by only four residences, this Classic Lowcountry-style home offers a rare combination of privacy, pedigree, and place. Originally built by Steve Tilton of Coastal Signature Homes, the residence reflects the craftsmanship and thoughtful detailing this builder is known for, from refined millwork to finishes selected with an eye for timeless quality.The setting is equally exceptional. Recently expanded to 1.09 acres, the property is canopied by mature Live Oaks and offers partial marsh views, creating a sense of seclusion that's increasingly rare to find. With only three neighboring homes on the entire street, this feels less like a residential lot and more like a private retreat, the kind of privacy that simply can't be recreated.This is Lowcountry living at its most authentic: classic architecture, masterful construction, and a setting defined by nature, quiet, and space to breathe.

3 Beds ⋅ 3 Baths ⋅ 3,103 SqFt. ⋅ HILTONHEAD-510836 MLS

Tucked at the end of a quiet cul-de-sac and shared by only four residences, this Classic Lowcountry-style home offers a rare combination of privacy, pedigree, and place. Originally built by Steve Tilton of Coastal Signature Homes, the residence reflects the craftsmanship and thoughtful detailing this builder is known for, from refined millwork to finishes selected with an eye for timeless quality.The setting is equally exceptional. Recently expanded to 1.09 acres, the property is canopied by mature Live Oaks and offers partial marsh views, creating a sense of seclusion that's increasingly rare to find. With only three neighboring homes on the entire street, this feels less like a residential lot and more like a private retreat, the kind of privacy that simply can't be recreated.This is Lowcountry living at its most authentic: classic architecture, masterful construction, and a setting defined by nature, quiet, and space to breathe.

6 Winding Oak Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,150,000

An incredible opportunity and unbelievable value to have three wonderful views of marsh, lagoon, and golf. This charming recently renovated Lowcountry Club Cottage is move in ready and yours to enjoy morning sunrises over the marsh. Located on the finishing 9th hole of the Dogwood course, this open floor plan with high ceiling is perfect for entertaining. 3 bedrooms, 1st-floor master, 3.5 baths, 2nd floor Guest Suite with terrific three views. Large screened in porch and backyard offer a great outdoor living space. The Club Cottage Section offers a unique opportunity, within Callawassie Island, for a Primary Home or Investment Rental Property (overnight stay to long term rental flexibility). The Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

3 Beds ⋅ 4 Baths ⋅ 2,734 SqFt. ⋅ HILTONHEAD-510205 MLS

An incredible opportunity and unbelievable value to have three wonderful views of marsh, lagoon, and golf. This charming recently renovated Lowcountry Club Cottage is move in ready and yours to enjoy morning sunrises over the marsh. Located on the finishing 9th hole of the Dogwood course, this open floor plan with high ceiling is perfect for entertaining. 3 bedrooms, 1st-floor master, 3.5 baths, 2nd floor Guest Suite with terrific three views. Large screened in porch and backyard offer a great outdoor living space. The Club Cottage Section offers a unique opportunity, within Callawassie Island, for a Primary Home or Investment Rental Property (overnight stay to long term rental flexibility). The Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

14 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$385,000

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.

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

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.

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.

$1,195,000

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.

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.

$2,895,000

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.

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.

6 Dolphin Landing, Okatie

Listing courtesy of Charter One Realty.

$695,000

This Lowcountry home, ideally situated within the Club Cottage section of Callawassie Island, offers a unique blend of flexibility and lifestyle, perfect as a primary residence, second home, or an investment opportunity with rental income potential as you begin your transition south.Featuring 3 bedrooms and 3 baths, the home is thoughtfully positioned to capture sweeping golf and marsh views overlooking Dogwood #9. A spacious rear porch with cable railings enhances the setting, allowing for uninterrupted, expansive views and seamless outdoor living. The Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

3 Beds ⋅ 3 Baths ⋅ 2,276 SqFt. ⋅ HILTONHEAD-507603 MLS

This Lowcountry home, ideally situated within the Club Cottage section of Callawassie Island, offers a unique blend of flexibility and lifestyle, perfect as a primary residence, second home, or an investment opportunity with rental income potential as you begin your transition south.Featuring 3 bedrooms and 3 baths, the home is thoughtfully positioned to capture sweeping golf and marsh views overlooking Dogwood #9. A spacious rear porch with cable railings enhances the setting, allowing for uninterrupted, expansive views and seamless outdoor living. The Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

8 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$900,000

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 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.

$1,025,000

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. Recent updates include a brand-new roof (2026) and new HVAC system (2025), adding value and move-in-ready confidence. 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 and 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.

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. Recent updates include a brand-new roof (2026) and new HVAC system (2025), adding value and move-in-ready confidence. 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 and 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.

$329,000

Welcome to 49 Heron Walk on Callawassie Island. Perfectly positioned on the fairway of the 1st hole of the Dogwood Course, this classic golf cottage delivers a true front-row seat to opening drives and glowing morning sunrises over the fairway. Lovingly maintained in remarkable original condition (with updated mechanicals), the home features warm woodwork, comfortable living spaces, and authentic 80s character throughout. Enjoy it just as it is, or modernize to your taste--either way, you're starting with an unbeatable golf course setting and timeless island appeal. Live here full time, use as a 2nd home or create income as a sought-after retreat for visiting golfers. This is island living with timeless style. Optional Golf Membership.

3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-505169 MLS

Welcome to 49 Heron Walk on Callawassie Island. Perfectly positioned on the fairway of the 1st hole of the Dogwood Course, this classic golf cottage delivers a true front-row seat to opening drives and glowing morning sunrises over the fairway. Lovingly maintained in remarkable original condition (with updated mechanicals), the home features warm woodwork, comfortable living spaces, and authentic 80s character throughout. Enjoy it just as it is, or modernize to your taste--either way, you're starting with an unbeatable golf course setting and timeless island appeal. Live here full time, use as a 2nd home or create income as a sought-after retreat for visiting golfers. This is island living with timeless style. Optional Golf Membership.

49 Heron Walk, Okatie

Listing courtesy of Moul, REALTORS®.

$689,900

A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.

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

A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.

49 Winding Oak Drive, Okatie

Listing courtesy of Charter One Realty.

$599,000

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.

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.

$6,500,000

Experience the soul of Lowcountry living in this enchanting deep-water estate, where timeless Southern charm meets exceptional craftsmanship. A sweeping wraparound porch captures gentle river breezes and sets the stage for unforgettable sunrises and slow, breezy afternoons. Inside, soaring vaulted ceilings, abundant natural light, and warm, inviting finishes create an atmosphere of effortless elegance. The gourmet kitchen is perfect for gatherings, offering refined style and functionality. A spacious mother-in-law and beautifully appointed detached carriage house provide unmatched flexibility for guests or extended family. The oversized 4+ garage and generous walk out storage-with bathrooms-ensure space for every hobby, project, and coastal toy. A rare 4-stop elevator adds ease to daily living. On the river, a private deep-water dock awaits with an impressive 18,000 lb lift and a covered perch above the water-an idyllic spot to relax, unwind, and savor the beauty of the Lowcountry. Thoughtfully wired for a whole home generator, this estate blends comfort, luxury, and Southern grace in every detail.

5 Beds ⋅ 9 Baths ⋅ 8,362 SqFt. ⋅ HILTONHEAD-502660 MLS

Experience the soul of Lowcountry living in this enchanting deep-water estate, where timeless Southern charm meets exceptional craftsmanship. A sweeping wraparound porch captures gentle river breezes and sets the stage for unforgettable sunrises and slow, breezy afternoons. Inside, soaring vaulted ceilings, abundant natural light, and warm, inviting finishes create an atmosphere of effortless elegance. The gourmet kitchen is perfect for gatherings, offering refined style and functionality. A spacious mother-in-law and beautifully appointed detached carriage house provide unmatched flexibility for guests or extended family. The oversized 4+ garage and generous walk out storage-with bathrooms-ensure space for every hobby, project, and coastal toy. A rare 4-stop elevator adds ease to daily living. On the river, a private deep-water dock awaits with an impressive 18,000 lb lift and a covered perch above the water-an idyllic spot to relax, unwind, and savor the beauty of the Lowcountry. Thoughtfully wired for a whole home generator, this estate blends comfort, luxury, and Southern grace in every detail.

107 Okatie Highway, Okatie

Listing courtesy of Collins Group Realty.

$1,395,000

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

4 Beds ⋅ 4 Baths ⋅ 2,860 SqFt. ⋅ HILTONHEAD-501726 MLS

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

27 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,390,000

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.

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.

$625,000

Accessible Lowcountry Living on beautiful Callawassie Island! Located on quiet, desirable Osprey Circle, this well-established home is surrounded by towering pines, palms and classic island charm. This quality constructed home, built by the Tilton Group, offers over 2,700 finished square feet, the flexible layout includes wide-plank flooring, attic foam insulation, crawlspace encapsulation, and remodeled kitchen (2019). New roof 8/2026! The living room with fireplace flows to the dining area, breakfast nook, and screened porch with tranquil lagoon views. Designed for easy, single-level living, the primary suite is privately situated opposite two guest bedrooms. A spacious bonus room with en-suite bath over the garage provides ideal flexspace for guests, office or den. Thoughtfully laid out and ready for personal touches, this home offers space, privacy, and opportunity in one of Callawassie's most sought-after locations. Enjoy renowned Island amenities including golf, tennis, pickleball, fitness center, docks, clubhouse dining, 24-hour gated security, and a vibrant social community, all conveniently located between Hilton Head, Bluffton and Beaufort.

4 Beds ⋅ 3 Baths ⋅ 2,720 SqFt. ⋅ HILTONHEAD-446580 MLS

Accessible Lowcountry Living on beautiful Callawassie Island! Located on quiet, desirable Osprey Circle, this well-established home is surrounded by towering pines, palms and classic island charm. This quality constructed home, built by the Tilton Group, offers over 2,700 finished square feet, the flexible layout includes wide-plank flooring, attic foam insulation, crawlspace encapsulation, and remodeled kitchen (2019). New roof 8/2026! The living room with fireplace flows to the dining area, breakfast nook, and screened porch with tranquil lagoon views. Designed for easy, single-level living, the primary suite is privately situated opposite two guest bedrooms. A spacious bonus room with en-suite bath over the garage provides ideal flexspace for guests, office or den. Thoughtfully laid out and ready for personal touches, this home offers space, privacy, and opportunity in one of Callawassie's most sought-after locations. Enjoy renowned Island amenities including golf, tennis, pickleball, fitness center, docks, clubhouse dining, 24-hour gated security, and a vibrant social community, all conveniently located between Hilton Head, Bluffton and Beaufort.

63 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.