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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.

$850,000

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.

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.

$1,350,000

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.

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.

$914,000

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, expansive windows fill the home with natural light while showcasing the stunning scenery from nearly every room. The spacious great room features cathedral ceilings, custom bookshelves with storage, and an updated fireplace, creating a warm and inviting gathering space. The great room flows seamlessly into the updated kitchen and four-season Carolina room, making the home ideal for both entertaining and quiet relaxation. Recent improvements include upfitted kitchen cabinets, new kitchen appliances, countertops, and a farmhouse sink, along with wide-plank engineered English oak floors and a new HVAC system (2026), bringing modern style and comfort throughout the home. The primary suite offers a serene escape with tranquil marsh views, a beautifully renovated bath, and generous his-and-her walk-in closets. Flexible living spaces provide options for a home office, formal dining room, or additional guest accommodations, allowing the home to adapt easily to a variety of lifestyles. Outdoor living is equally inviting, with a shaded deck that provides the perfect setting for morning coffee while taking in the peaceful marsh views and abundant Lowcountry wildlife. Located within the private, gated golf community of Callawassie Island, residents enjoy access to world-class amenities including 27 holes of Tom Fazio-designed golf, tennis, pickleball, fitness facilities, community docks, dining, pools, and miles of scenic marshfront beauty. Ideally positioned between Beaufort, Bluffton, Hilton Head, and Savannah, 8 Chechessee Circle offers the perfect balance of privacy, luxury, natural beauty, and convenience.

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, expansive windows fill the home with natural light while showcasing the stunning scenery from nearly every room. The spacious great room features cathedral ceilings, custom bookshelves with storage, and an updated fireplace, creating a warm and inviting gathering space. The great room flows seamlessly into the updated kitchen and four-season Carolina room, making the home ideal for both entertaining and quiet relaxation. Recent improvements include upfitted kitchen cabinets, new kitchen appliances, countertops, and a farmhouse sink, along with wide-plank engineered English oak floors and a new HVAC system (2026), bringing modern style and comfort throughout the home. The primary suite offers a serene escape with tranquil marsh views, a beautifully renovated bath, and generous his-and-her walk-in closets. Flexible living spaces provide options for a home office, formal dining room, or additional guest accommodations, allowing the home to adapt easily to a variety of lifestyles. Outdoor living is equally inviting, with a shaded deck that provides the perfect setting for morning coffee while taking in the peaceful marsh views and abundant Lowcountry wildlife. Located within the private, gated golf community of Callawassie Island, residents enjoy access to world-class amenities including 27 holes of Tom Fazio-designed golf, tennis, pickleball, fitness facilities, community docks, dining, pools, and miles of scenic marshfront beauty. Ideally positioned between Beaufort, Bluffton, Hilton Head, and Savannah, 8 Chechessee Circle offers the perfect balance of privacy, luxury, natural beauty, and convenience.

8 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,080,000

When you cross over the causeway into Callawassie Island, you are transported into a peaceful private world where moss-draped oaks, winding marsh views, and quiet coastal beauty instantly replace the pace of everyday life, creating a true sense of retreat the moment you arrive. Driving past beautifully manicured golf fairways woven seamlessly with natural wildlife habitat and serene lagoons, every turn offers a blend of refined landscape and untouched Lowcountry beauty. The charm continues right into this new construction home, where thoughtful design and setting feature 3 bedrooms in the main house and an in-law suite above the garage. It's perfect for guests, extended family, or flexible living arrangements that adapt easily to your lifestyle. Welcome home to 26 Longwood.

4 Beds ⋅ 4 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-503887 MLS

When you cross over the causeway into Callawassie Island, you are transported into a peaceful private world where moss-draped oaks, winding marsh views, and quiet coastal beauty instantly replace the pace of everyday life, creating a true sense of retreat the moment you arrive. Driving past beautifully manicured golf fairways woven seamlessly with natural wildlife habitat and serene lagoons, every turn offers a blend of refined landscape and untouched Lowcountry beauty. The charm continues right into this new construction home, where thoughtful design and setting feature 3 bedrooms in the main house and an in-law suite above the garage. It's perfect for guests, extended family, or flexible living arrangements that adapt easily to your lifestyle. Welcome home to 26 Longwood.

26 Longwood Drive, Okatie

Listing courtesy of Moul, REALTORS®.

$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.