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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.

$1,425,000

Welcome to secluded Low Country living with 5 acres of privacy, yet close to daily conveniences. The private gated entry flanks the meandering drive through the wooded entrance to the manicured grounds surrounding the home with a pool in the rear and a pond in the distance. This four-bedroom home with study and 3 car garage includes upper tier custom features with 8' interior doors, wood floors, ensuite baths for each bedroom, a butler's pantry, laundry/storage room, and walk in attic. The primary ensuite bath offers double vanities, jetted soaking tub and two-sided Roman shower with multiple shower heads. The customized primary closet is the size of many bedrooms! The Great room leads out to the screened porch overlooking the pool flanked with pavers for lounge chairs and pool side gatherings. The large outbuilding offers many possibilities from RV/horse barn to boat storage/workshop. Under roof of the outbuilding is one of the nicest custom built chicken coops you will ever find! A truly exceptional property and a rare opportunity. Be sure to click link for virtual tour and drone footage!

4 Beds ⋅ 5 Baths ⋅ 3,413 SqFt. ⋅ HILTONHEAD-511901 MLS

Welcome to secluded Low Country living with 5 acres of privacy, yet close to daily conveniences. The private gated entry flanks the meandering drive through the wooded entrance to the manicured grounds surrounding the home with a pool in the rear and a pond in the distance. This four-bedroom home with study and 3 car garage includes upper tier custom features with 8' interior doors, wood floors, ensuite baths for each bedroom, a butler's pantry, laundry/storage room, and walk in attic. The primary ensuite bath offers double vanities, jetted soaking tub and two-sided Roman shower with multiple shower heads. The customized primary closet is the size of many bedrooms! The Great room leads out to the screened porch overlooking the pool flanked with pavers for lounge chairs and pool side gatherings. The large outbuilding offers many possibilities from RV/horse barn to boat storage/workshop. Under roof of the outbuilding is one of the nicest custom built chicken coops you will ever find! A truly exceptional property and a rare opportunity. Be sure to click link for virtual tour and drone footage!

124 Chechessee Road, Okatie

Listing courtesy of Charter One Realty.

$469,900

Located in the sought-after Sun City Hilton Head 55+ active adult community, this meticulously cared-for Taft Street Model offers the feel of a larger home with the convenience of a more manageable size. Featuring 2 bedrooms, 2 bathrooms and a versatile flex/office/hobby room, this home is ideal for retirees, those relocating to the Lowcountry, or anyone working from home.The welcoming entry opens to an inviting open-concept floor plan with views through the living room and dining area into one of the home's standout features-the spacious gourmet kitchen. Designed for everyday living and entertaining, the kitchen offers abundant cabinetry, a large center island and quality appliances, providing plenty of space for everything from casual meals to gatherings with family and friends.Just beyond the kitchen, the Carolina Room adds valuable living space and flexibility. Use it as a comfortable sitting room, additional dining area, reading space or entertaining room while enjoying peaceful views of the landscaped backyard and mature berm that provides added privacy. The oversized patio offers plenty of room for outdoor dining and entertaining, with potential to add additional outdoor living space.The primary bedroom features an en-suite bathroom with an extended vanity, step-in shower and walk-in closet with additional storage. The flex room is currently being used as an artist's studio, with front-facing windows that provide wonderful natural light.This home is located in a Managed Neighborhood, where basic lawn care is included with the HOA-an added convenience for a low-maintenance lifestyle. This move in ready home should not be missed! Ideally positioned between Argent Lakes Amenity Center & Golf Course and the newly opened Westside Amenity & Fitness Center, residents enjoy easy access to resort-style amenities including one of the largest outdoor pool in the area. Sun City Hilton Head offers multiple golf courses, pools, tennis, pickleball, fitness centers, restaurants and more than 125 clubs and groups.Enjoy the Lowcountry lifestyle with easy access to Bluffton, Hilton Head Island, Beaufort and Savannah, with Charleston also within reach for day trips and weekend adventures.

2 Beds ⋅ 2 Baths ⋅ 1,548 SqFt. ⋅ HILTONHEAD-512092 MLS

Located in the sought-after Sun City Hilton Head 55+ active adult community, this meticulously cared-for Taft Street Model offers the feel of a larger home with the convenience of a more manageable size. Featuring 2 bedrooms, 2 bathrooms and a versatile flex/office/hobby room, this home is ideal for retirees, those relocating to the Lowcountry, or anyone working from home.The welcoming entry opens to an inviting open-concept floor plan with views through the living room and dining area into one of the home's standout features-the spacious gourmet kitchen. Designed for everyday living and entertaining, the kitchen offers abundant cabinetry, a large center island and quality appliances, providing plenty of space for everything from casual meals to gatherings with family and friends.Just beyond the kitchen, the Carolina Room adds valuable living space and flexibility. Use it as a comfortable sitting room, additional dining area, reading space or entertaining room while enjoying peaceful views of the landscaped backyard and mature berm that provides added privacy. The oversized patio offers plenty of room for outdoor dining and entertaining, with potential to add additional outdoor living space.The primary bedroom features an en-suite bathroom with an extended vanity, step-in shower and walk-in closet with additional storage. The flex room is currently being used as an artist's studio, with front-facing windows that provide wonderful natural light.This home is located in a Managed Neighborhood, where basic lawn care is included with the HOA-an added convenience for a low-maintenance lifestyle. This move in ready home should not be missed! Ideally positioned between Argent Lakes Amenity Center & Golf Course and the newly opened Westside Amenity & Fitness Center, residents enjoy easy access to resort-style amenities including one of the largest outdoor pool in the area. Sun City Hilton Head offers multiple golf courses, pools, tennis, pickleball, fitness centers, restaurants and more than 125 clubs and groups.Enjoy the Lowcountry lifestyle with easy access to Bluffton, Hilton Head Island, Beaufort and Savannah, with Charleston also within reach for day trips and weekend adventures.

277 Turnberry Woods Drive, Okatie

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$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.

$419,900

This 3 bedroom, 2.5 bath Ashwood model offers an open-concept floor plan with loads of natural light and a 20' great room ceiling with many windows. The layout is designed for first-floor living, with additional space upstairs to spread out. The kitchen includes a large island, quartz countertops, elongated cabinets, farmhouse sink, contrasting cabinet color. All appliances incl! LVP flooring on entire first floor. Smart thermostat and a $3,000 Vivint security system with doorbell camera, keypad, control panel, and indoor/outdoor cameras. The home includes a fenced backyard with a wooded view, a large front porch, a two-car garage, and a driveway with ample parking. Located in a boutique neighborhood wrapped in Lowcountry charm, just past Okatie Elementary. Beaufort, Bluffton, HHI and Savannah all within 20-30 mins.

3 Beds ⋅ 3 Baths ⋅ 1,660 SqFt. ⋅ HILTONHEAD-508347 MLS

This 3 bedroom, 2.5 bath Ashwood model offers an open-concept floor plan with loads of natural light and a 20' great room ceiling with many windows. The layout is designed for first-floor living, with additional space upstairs to spread out. The kitchen includes a large island, quartz countertops, elongated cabinets, farmhouse sink, contrasting cabinet color. All appliances incl! LVP flooring on entire first floor. Smart thermostat and a $3,000 Vivint security system with doorbell camera, keypad, control panel, and indoor/outdoor cameras. The home includes a fenced backyard with a wooded view, a large front porch, a two-car garage, and a driveway with ample parking. Located in a boutique neighborhood wrapped in Lowcountry charm, just past Okatie Elementary. Beaufort, Bluffton, HHI and Savannah all within 20-30 mins.

61 Whispering Oaks Circle, Okatie

Listing courtesy of Dunes Real Estate.

$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®.

$715,000

Extensively upgraded with over $100K in custom interior and exterior enhancements, this premium corner-lot home combines designer finishes, a dedicated home office, and thoughtfully engineered outdoor living rarely found in new construction at this price point. At the heart of the home is a designer kitchen featuring a full-height backsplash, custom hardwood vent hood, premium appliances, and curated lighting, complemented by a custom walk-in pantry with floor-to-ceiling built-in storage. The open-concept living areas are enhanced with extensive millwork and architectural detailing throughout, creating a refined, high-end feel rarely found at this price point. A dedicated home office with upgraded French doors provides an ideal work-from-home space, while the primary suite features a fully customized closet system offering exceptional organization and everyday ease. Outdoor living has been intentionally upgraded to deliver both beauty and long-term durability. The expansive Lowcountry paver patio provides the perfect space for entertaining and is already equipped with a gas stub for a grill or future outdoor kitchen. Professionally designed landscaping surrounds the home with layered privacy and curated plantings, while significant investments in drainage and irrigation-including French drains, underground gutter drainage, and a WiFi-enabled irrigation system-help keep the property functional and low-maintenance year-round. Unlike new construction, this home offers substantial post-build upgrades already completed, saving the next owner significant time, cost, and effort. Additional features include an enclosed service yard for organized exterior storage, smart home integrations, and consistent maintenance with termite protection and HVAC servicing. Located in the desirable Malind Bluff community, residents enjoy access to a resort-style pool, dock, pickleball courts, playground, and scenic Lowcountry surroundings. This is a rare opportunity to own a thoughtfully upgraded home where design, infrastructure, and lifestyle come together seamlessly.

4 Beds ⋅ 3 Baths ⋅ 3,090 SqFt. ⋅ HILTONHEAD-506561 MLS

Extensively upgraded with over $100K in custom interior and exterior enhancements, this premium corner-lot home combines designer finishes, a dedicated home office, and thoughtfully engineered outdoor living rarely found in new construction at this price point. At the heart of the home is a designer kitchen featuring a full-height backsplash, custom hardwood vent hood, premium appliances, and curated lighting, complemented by a custom walk-in pantry with floor-to-ceiling built-in storage. The open-concept living areas are enhanced with extensive millwork and architectural detailing throughout, creating a refined, high-end feel rarely found at this price point. A dedicated home office with upgraded French doors provides an ideal work-from-home space, while the primary suite features a fully customized closet system offering exceptional organization and everyday ease. Outdoor living has been intentionally upgraded to deliver both beauty and long-term durability. The expansive Lowcountry paver patio provides the perfect space for entertaining and is already equipped with a gas stub for a grill or future outdoor kitchen. Professionally designed landscaping surrounds the home with layered privacy and curated plantings, while significant investments in drainage and irrigation-including French drains, underground gutter drainage, and a WiFi-enabled irrigation system-help keep the property functional and low-maintenance year-round. Unlike new construction, this home offers substantial post-build upgrades already completed, saving the next owner significant time, cost, and effort. Additional features include an enclosed service yard for organized exterior storage, smart home integrations, and consistent maintenance with termite protection and HVAC servicing. Located in the desirable Malind Bluff community, residents enjoy access to a resort-style pool, dock, pickleball courts, playground, and scenic Lowcountry surroundings. This is a rare opportunity to own a thoughtfully upgraded home where design, infrastructure, and lifestyle come together seamlessly.

823 Danner Drive, Okatie

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$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.