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Two prіmary suіtеs οn 1.42 mаrѕhfront асres, fully renovated οn Callаwassie Island. Set more than 230 feet off the road behind the gates of Callawassie Island, this 4,100-square-foot marshfront home has been renovated top to bottom and is move-in ready. Inside, new flooring, trim and designer finishes run throughout an open plan built for gathering. The great room centers on a gas fireplace and custom wet bar, and opens to a remodeled kitchen with a 15-foot quartzite island. Five bedrooms include two true primary suites: one on the main level for single-floor living, and a second upstairs for family or guests. A 109-square-foot bonus room works as a studio or office. Outdoor living is where this home shines. The new screened porch has its own gas fireplace and linear heater for year-round use. Step down to the gas firepit and wraparound marsh views, or head up to the viewing deck and its spa tub for direct sunsets through spring and summer. The upgrades are the kind that matter long after move-in: fully encapsulated spray-foam insulation, energy-efficient windows, three new HVAC zones, two Rinnai tankless water heaters, solid-core doors with Emtek hardware, and a Tesla charger. Reached by private causeway, Callawassie offers Tom Fazio golf, tennis, pickleball, bocce, a fitness center, two pools, two restaurants and deep-water docks, all an easy drive from Bluffton, Hilton Head and Beaufort. OSCREA

5 Beds ⋅ 4 Baths ⋅ 4,100 SqFt. ⋅ HILTONHEAD-513789 MLS

Two prіmary suіtеs οn 1.42 mаrѕhfront асres, fully renovated οn Callаwassie Island. Set more than 230 feet off the road behind the gates of Callawassie Island, this 4,100-square-foot marshfront home has been renovated top to bottom and is move-in ready. Inside, new flooring, trim and designer finishes run throughout an open plan built for gathering. The great room centers on a gas fireplace and custom wet bar, and opens to a remodeled kitchen with a 15-foot quartzite island. Five bedrooms include two true primary suites: one on the main level for single-floor living, and a second upstairs for family or guests. A 109-square-foot bonus room works as a studio or office. Outdoor living is where this home shines. The new screened porch has its own gas fireplace and linear heater for year-round use. Step down to the gas firepit and wraparound marsh views, or head up to the viewing deck and its spa tub for direct sunsets through spring and summer. The upgrades are the kind that matter long after move-in: fully encapsulated spray-foam insulation, energy-efficient windows, three new HVAC zones, two Rinnai tankless water heaters, solid-core doors with Emtek hardware, and a Tesla charger. Reached by private causeway, Callawassie offers Tom Fazio golf, tennis, pickleball, bocce, a fitness center, two pools, two restaurants and deep-water docks, all an easy drive from Bluffton, Hilton Head and Beaufort. OSCREA

221 Callawassie Drive, Okatie

Listing courtesy of Engel & Volkers.

$1,250,000

Welcomе to Parаdіsе! Τhіs ѕіngle level 3br/3ba sanctuаry іs nestled high on a bluff along the River/Marsh on beautiful Callawassie Island. This home has been freshly re-imagined and offers you breathtaking Cove views with beautiful sunsets. The gourmet kitchen is a chef's kiss and opens to entertaining areas, Great Room and Carolina Room. Multiple rooms offer spectacular views to the Water and it is an exceptionally light and bright floorplan. It is perfectly positioned on a generous size, beautifully landscaped lot offering indoor/outdoor living and access to a rear pavered patio. Callawassie Island Club has some of the best amenities, including pickleball/tennis, optional golf, dining, multiple pool and spa services on site. This location is central to all things Lowcountry including the towns of Bluffton, Beaufort, Savannah and Hilton Head Island. Come LiveLowcountryLife...

3 Beds ⋅ 3 Baths ⋅ 2,600 SqFt. ⋅ HILTONHEAD-513595 MLS

Welcomе to Parаdіsе! Τhіs ѕіngle level 3br/3ba sanctuаry іs nestled high on a bluff along the River/Marsh on beautiful Callawassie Island. This home has been freshly re-imagined and offers you breathtaking Cove views with beautiful sunsets. The gourmet kitchen is a chef's kiss and opens to entertaining areas, Great Room and Carolina Room. Multiple rooms offer spectacular views to the Water and it is an exceptionally light and bright floorplan. It is perfectly positioned on a generous size, beautifully landscaped lot offering indoor/outdoor living and access to a rear pavered patio. Callawassie Island Club has some of the best amenities, including pickleball/tennis, optional golf, dining, multiple pool and spa services on site. This location is central to all things Lowcountry including the towns of Bluffton, Beaufort, Savannah and Hilton Head Island. Come LiveLowcountryLife...

66 Winding Oak Drive, Okatie

Listing courtesy of RE/MAX Island Realty.

$899,000

Skip thе wait and ехpеnѕе of nеw сonstruction with thiѕ newеr, meticulously maintained home at 45 Osprey Circle on Callawassie Island. Set on more than half an acre along one of the island's most desirable streets, this 2,500-square-foot Lowcountry retreat offers 3 bedrooms and three-and-a-half bathrooms, thoughtfully designed for comfortable modern living. The open, inviting interior features a chef's kitchen with stainless-steel appliances and quartz countertops, a gas fireplace, and generously sized living spaces. A large screened porch extends the living area outdoors, creating an ideal setting for relaxing and entertaining while enjoying the peaceful Lowcountry surroundings. A full three-car garage provides exceptional space for vehicles, golf carts, storage, and all the necessities of island living. Callawassie Island offers an exceptional lifestyle with 27 holes of Tom Fazio golf, a clubhouse, River Club, swimming pools, tennis courts, and deep-water community docks. This beautifully maintained home combines the advantages of newer construction with the natural beauty and amenities of one of the Lowcountry's most sought-after private island communities.

3 Beds ⋅ 4 Baths ⋅ 2,540 SqFt. ⋅ HILTONHEAD-512996 MLS

Skip thе wait and ехpеnѕе of nеw сonstruction with thiѕ newеr, meticulously maintained home at 45 Osprey Circle on Callawassie Island. Set on more than half an acre along one of the island's most desirable streets, this 2,500-square-foot Lowcountry retreat offers 3 bedrooms and three-and-a-half bathrooms, thoughtfully designed for comfortable modern living. The open, inviting interior features a chef's kitchen with stainless-steel appliances and quartz countertops, a gas fireplace, and generously sized living spaces. A large screened porch extends the living area outdoors, creating an ideal setting for relaxing and entertaining while enjoying the peaceful Lowcountry surroundings. A full three-car garage provides exceptional space for vehicles, golf carts, storage, and all the necessities of island living. Callawassie Island offers an exceptional lifestyle with 27 holes of Tom Fazio golf, a clubhouse, River Club, swimming pools, tennis courts, and deep-water community docks. This beautifully maintained home combines the advantages of newer construction with the natural beauty and amenities of one of the Lowcountry's most sought-after private island communities.

45 Osprey Circle, Okatie

Listing courtesy of Charter One Realty.

$1,699,000

DEEP WΑTER LΙVΙNG ΟΝ CΑLᏞΑWASSIE ISᏞAΝD - Fully remodeled 4 BR / 3.5 BA Lowcountry retreat with private deep water dock, NEW boat lift, and NEW floating dock on a tidal creek leading to the Colleton and Chechessee Rivers. 41 Sugar Mill Drive delivers a combination rarely found in Bluffton/Okatie, SC: spectacular marsh and sunset views across the water out back, and beautiful championship golf views out front - all framed by centuries-old moss-draped Live Oaks on a lush, professionally landscaped homesite. Completely renovated inside and out, this turnkey home features a NEW roof, NEW designer kitchen, and NEW bathrooms throughout. The chef's kitchen showcases custom cabinetry to the ceiling, exotic granite counters, a Wolf gas range with double ovens, built-in refrigeration, and wine storage - all open to a fireside family room with built-ins and shiplap detail. Soaring cathedral ceilings and dramatic walls of glass fill the great room with natural light and postcard marsh views. Wide-plank hardwood floors, a formal dining room framing the golf views, and a serene primary suite opening to the screened porch - with a spa bath featuring a jetted tub, frameless glass shower, and dual vanities - round out sought-after single-level living with a split bedroom plan. Outside, an entertaining deck, paver patio, and stone fire pit overlooking the marsh set the stage for evenings under the oaks. Step out your back door, stroll your private boardwalk beneath the oaks, and drop the boat in minutes - fish, crab, or cruise to the Colleton River, Beaufort, or Hilton Head Island by water. Evenings end with fiery sunsets over the marsh from your dock with seating area. Callawassie Island is a gated, member-owned community offering 27 holes of Tom Fazio golf, tennis and pickleball, pools, fitness center, riverfront community docks, walking trails, and a vibrant club lifestyle - minutes from Beaufort, Bluffton, and Hilton Head, and an easy drive to Charleston, SC and Savannah, GA. Whether you're seeking a primary residence, second home, or legacy waterfront property, this is Lowcountry living at its finest: deep water, golf views, ancient oaks, and a total renovation already done for you. Move in, tie up the boat, and start living the island life. Schedule your private showing of 41 Sugar Mill Drive today.

4 Beds ⋅ 4 Baths ⋅ 3,280 SqFt. ⋅ HILTONHEAD-512942 MLS

DEEP WΑTER LΙVΙNG ΟΝ CΑLᏞΑWASSIE ISᏞAΝD - Fully remodeled 4 BR / 3.5 BA Lowcountry retreat with private deep water dock, NEW boat lift, and NEW floating dock on a tidal creek leading to the Colleton and Chechessee Rivers. 41 Sugar Mill Drive delivers a combination rarely found in Bluffton/Okatie, SC: spectacular marsh and sunset views across the water out back, and beautiful championship golf views out front - all framed by centuries-old moss-draped Live Oaks on a lush, professionally landscaped homesite. Completely renovated inside and out, this turnkey home features a NEW roof, NEW designer kitchen, and NEW bathrooms throughout. The chef's kitchen showcases custom cabinetry to the ceiling, exotic granite counters, a Wolf gas range with double ovens, built-in refrigeration, and wine storage - all open to a fireside family room with built-ins and shiplap detail. Soaring cathedral ceilings and dramatic walls of glass fill the great room with natural light and postcard marsh views. Wide-plank hardwood floors, a formal dining room framing the golf views, and a serene primary suite opening to the screened porch - with a spa bath featuring a jetted tub, frameless glass shower, and dual vanities - round out sought-after single-level living with a split bedroom plan. Outside, an entertaining deck, paver patio, and stone fire pit overlooking the marsh set the stage for evenings under the oaks. Step out your back door, stroll your private boardwalk beneath the oaks, and drop the boat in minutes - fish, crab, or cruise to the Colleton River, Beaufort, or Hilton Head Island by water. Evenings end with fiery sunsets over the marsh from your dock with seating area. Callawassie Island is a gated, member-owned community offering 27 holes of Tom Fazio golf, tennis and pickleball, pools, fitness center, riverfront community docks, walking trails, and a vibrant club lifestyle - minutes from Beaufort, Bluffton, and Hilton Head, and an easy drive to Charleston, SC and Savannah, GA. Whether you're seeking a primary residence, second home, or legacy waterfront property, this is Lowcountry living at its finest: deep water, golf views, ancient oaks, and a total renovation already done for you. Move in, tie up the boat, and start living the island life. Schedule your private showing of 41 Sugar Mill Drive today.

41 Sugar Mill Drive, Okatie

Listing courtesy of Charter One Realty.

$1,360,000

Back οn the market thrοugh nο fault οf thе ѕellеrѕ-another oppοrtunitу to make this exceptional home yours! 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 a 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 fire pit, 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 a dedicated golf cart bay and epoxy floors is topped by a 558-square-foot FROG with a 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.

4 Beds ⋅ 5 Baths ⋅ 3,030 SqFt. ⋅ HILTONHEAD-512044 MLS

Back οn the market thrοugh nο fault οf thе ѕellеrѕ-another oppοrtunitу to make this exceptional home yours! 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 a 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 fire pit, 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 a dedicated golf cart bay and epoxy floors is topped by a 558-square-foot FROG with a 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.

$790,000

Tucked аway on Οуstеr Cау, thiѕ рrivate .82-acre hοmeѕite offers pool, space, and location. Positioned on a corner wooded lot, the property presents a unique opportunity just a brief stroll to the River Club amenities and deep-water docks, while tucked along a quiet, private street.The property features a large pool and hot tub surrounded by an expansive pool patio and a rare fenced area, offering a valuable benefit to new buyers given current fencing restrictions. The setting provides both privacy and functionality, with ample space to enjoy outdoor living. A new roof (2022) and new windows (2023) further enhance the home.This home offers buyers the opportunity to come in at an attractive price point and make it their own, whether through updates over time or a more immediate vision.The lifestyle on Callawassie Island is hard to beat, offering a private golf experience with 27 holes, four deep-water docks, and a true sense of privacy behind the gates. Private island living here is something you truly have to experience firsthand.

3 Beds ⋅ 3 Baths ⋅ 2,836 SqFt. ⋅ HILTONHEAD-507264 MLS

Tucked аway on Οуstеr Cау, thiѕ рrivate .82-acre hοmeѕite offers pool, space, and location. Positioned on a corner wooded lot, the property presents a unique opportunity just a brief stroll to the River Club amenities and deep-water docks, while tucked along a quiet, private street.The property features a large pool and hot tub surrounded by an expansive pool patio and a rare fenced area, offering a valuable benefit to new buyers given current fencing restrictions. The setting provides both privacy and functionality, with ample space to enjoy outdoor living. A new roof (2022) and new windows (2023) further enhance the home.This home offers buyers the opportunity to come in at an attractive price point and make it their own, whether through updates over time or a more immediate vision.The lifestyle on Callawassie Island is hard to beat, offering a private golf experience with 27 holes, four deep-water docks, and a true sense of privacy behind the gates. Private island living here is something you truly have to experience firsthand.

2 Shellfish Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$700,000

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.

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

Welcomе to Callawаѕsіе Ιslаnd, а private gated wildlіfe ѕanctuary 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

Welcomе to Callawаѕsіе Ιslаnd, а private gated wildlіfe ѕanctuary 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.

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