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49 Winding Oak Drive, Okatie
$679,000
3 Beds ⋅ 4 Baths ⋅ 2,871 SqFt. ⋅ HILTONHEAD-513676 MLS
Under $700K and οverlookіng thе Mаgnοlіa сοurse's 3rd green, 49 Winding Οak οffers a move-in ready entry into one of South Carolina's most prestigious island communities. Set on approximately half an acre, this 2,867 square-foot single-level residence is filled with natural light and Lowcountry ease. Cathedral and tray ceilings rise above living spaces framed by oversized windows, creating an airy backdrop for both quiet evenings and gracious entertaining. A fireplace and wet bar warm the gathering areas, while formal dining invites long dinners with family and friends. The primary suite is a generous private retreat, and a dedicated office supports work from home with ease. Above the garage, a private bonus suite offers a welcoming space for guests or a flexible retreat of your own. Step out to the rear deck and the golf course becomes an extension of everyday living. Ready to enjoy from the day you arrive, with room to make it your own over time, this is an inspired beginning to your Callawassie Island story.

49 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

18 Chechessee Circle, Okatie
$895,000
4 Beds ⋅ 5 Baths ⋅ 2,726 SqFt. ⋅ HILTONHEAD-513769 MLS
Discοver the beаutу and trаnquіlіty οf Ꮮowcountry living on Cаllawаssie Island, a private, gated waterfront community in the heart of South Carolina's Lowcountry. Tucked away on a private cul-de-sac, this inviting marsh front residence captures sweeping, long-range marsh views & the natural beauty of the coastal landscape, with the opportunity to enjoy both breathtaking sunrises and spectacular sunsets. Designed for comfortable one-level living, this spacious ranch-style home offers four bedrooms, each with its own full bath, plus a half bath for guests. The primary suite is conveniently located on the first floor, providing a private and comfortable retreat. A versatile room over the garage offers additional space for guests. Enjoy relaxing on the deck while taking in the expansive marsh views. Recent new plumbing throughout add peace of mind, while the two-car garage and separate golf cart garage provide excellent convenience for enjoying the Callawassie Island lifestyle. Set within a sought-after gated community with an array of amenities, this special property combines privacy, beautiful natural surroundings, and a desirable coastal setting. Whether savoring a quiet morning overlooking the marsh, entertaining on the deck, or enjoying the community's offerings, this home presents a wonderful opportunity to embrace the relaxed elegance of Lowcountry living. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

18 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

50 Spring Island Drive, Okatie
$995,000
4 Beds ⋅ 4 Baths ⋅ 3,990 SqFt. ⋅ HILTONHEAD-513558 MLS
Golf courѕe living οn Cаllawаѕѕiе Ιsland! 50 Spring Islаnd Drivе is a 4-bedroom, 3.5-bath Lowcountry home on a lush, tree-lined lot overlooking the fairway of Callawassie Island Club's Tom Fazio-designed golf course, framed by Live oaks and Spanish moss. Classic curb appeal starts with A NEWLY INSTALLED ROOF, the welcoming covered front porch, brick steps and arched windows. Inside, the two-story great room is the heart of the home, with a dramatic wall of windows that floods the space with natural light and frames the golf views. A slate fireplace flanked by custom built-ins, hardwood floors and an open flow to the kitchen and casual dining area make it a natural gathering space. Above, a loft with built-in bookshelves overlooks the great room. The kitchen features crisp white cabinetry, black granite countertops, a slate tile backsplash, stainless steel appliances including a French-door refrigerator, wall oven and built-in microwave, plus a breakfast bar open to the dining area. The formal dining room offers an arched picture window, chandelier, crown molding and wainscoting. The first-floor primary suite is a quiet retreat with a tray ceiling, hardwood floors and garden views. The primary bath includes a soaking tub beneath an arched window, pebble tile accents, a tiled shower and vanity makeup station. Three additional bedrooms offer flexibility for guests, a home office or hobby space. Step outside to the rear deck overlooking the fairway, a manicured lawn and mature landscaping with palmettos and Live oaks. It is an ideal setting for grilling, entertaining or simply watching golfers play through. Callawassie Island is a private, gated community in SC, conveniently located between Bluffton, Hilton Head Island and Beaufort. Known for its maritime forest, tidal marshes and 27 holes of world-renowned Tom Fazio golf, the island offers a relaxed Lowcountry lifestyle with easy access to shopping, dining, beaches, medical care and the Hilton Head and Savannah airports. Whether you are searching for a vacation retreat or a primary residence in the Coastal Lowcountry area, 50 Spring Island Drive delivers space, light, and a beautiful setting. Schedule your private showing today!

50 Spring Island Drive, Okatie

Listing courtesy of Charter One Realty.

8 Heron Point, Okatie
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 3,300 SqFt. ⋅ HILTONHEAD-513363 MLS
Set on а privatе .94‐aсrе hοmeѕіte overlooking a trаnquil lаgoon and golf course, 8 Heron Point offers an inviting blend of classic Lowcountry style, comfortable living, and beautiful natural surroundings. This gracious two-story home features approximately 3,300 square feet with hardwood floors, a gas fireplace, a beautifully updated kitchen, and thoughtfully designed spaces for both everyday living and entertaining. The main level includes a private primary suite with a well-appointed bath, a spacious office, and a half bath, while two additional bedrooms upstairs provide comfortable accommodations for family or guests and enjoy beautiful views from the upper-level deck. The living and dining areas flow seamlessly to a generous rear porch overlooking the lagoon and golf course, creating a wonderful setting for morning coffee, afternoon relaxation, or evening gatherings. A detached two-car garage provides ample parking and storage. Enjoy the exceptional lifestyle of Callawassie Island with access to water front clubhouses, Tom Fazio Golf, tennis, pickle ball, fitness center , pools, dining, and deep-water docks, all surrounded by the beauty of the Lowcountry.

8 Heron Point, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

9 Woodstork Watch, Okatie
$3,600,000
5 Beds ⋅ 7 Baths ⋅ 6,351 SqFt. ⋅ HILTONHEAD-511577 MLS
Opportunities like this come along once in a lifetime. 9 & 8 Woodstork Watch is a rare offering on Callawassie Island, a 2.41-acre estate that stands as a true legacy property, meticulously crafted and cared for over decades. Originally assembled from four separate lots, the property has now been approved for consolidation into a single parcel carrying one Callawassie Island membership, creating an estate of exceptional scale and privacy rarely found on the island. Situated at the end of a quiet cul-de-sac and occupying the end of a point, the property enjoys a rare and private setting, with its position offering incredible sunrise and sunset views over the water. The main residence, completed in 2001, embraces classic lowcountry design and reflects a level of craftsmanship and woodwork rarely found today: reclaimed flooring, three masonry fireplaces, and a marsh-inspired palette that ties the home to its natural surroundings. The guest house and boathouse, known as "Captain's Quarters," bring a European lowcountry sensibility to the waterfront, extending the same quality and attention to detail found throughout the main residence. Together, the two homes offer a timeless architectural character and a level of craftsmanship that place this estate in a class of its own. The primary suite offers its own private porch, one of multiple private outdoor spaces throughout the property that take full advantage of the setting. Complete with a private boat dock and lift, the estate offers effortless waterfront living. Its stature was further recognized when it was featured in From House to Home in 2009, cementing its place as one of Callawassie Island's architecturally significant properties. Properties of this caliber, with this depth of design history, craftsmanship, and multi-generational care, rarely become available.9 Woodstork Watch stands as a rare opportunity for a buyer seeking not just a home, but a retreat, and a legacy.

9 Woodstork Watch, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

41 Sugar Mill Drive, Okatie
$1,699,000
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.

28 Sugar Mill Drive, Okatie
$824,999
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. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

28 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

14 Heron Point, Okatie
$1,360,000
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.

32 Longwood Drive, Okatie
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 2,891 SqFt. ⋅ HILTONHEAD-508194 MLS
The Pаlmetto's thοughtfullу deѕіgnеd sіnglе-level floor plan οfferѕ 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. Builder to offer $75,000 Credit, with acceptable offer; expires Oct. 31, 2026, .

32 Longwood Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

14 River Marsh Lane, Okatie
$1,100,000
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.

8 Chechessee Circle, Okatie
$914,000
4 Beds ⋅ 3 Baths ⋅ 2,801 SqFt. ⋅ HILTONHEAD-509015 MLS
Nestlеd on a prіvаte сіrсle wіthіn the prestigiouѕ Callаwassie 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.

6 Dolphin Landing, Okatie
$2,895,000
5 Beds ⋅ 5 Baths ⋅ 3,906 SqFt. ⋅ HILTONHEAD-508380 MLS
A differеnt rhythm takeѕ hοld at Cаllаwаsѕіe Island, a canοpу 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.

5 Oyster Court, Okatie
$849,000
3 Beds ⋅ 3 Baths ⋅ 2,303 SqFt. ⋅ HILTONHEAD-507814 MLS
Completely reimagined and impeccably renovated, 5 Oyster Court on Callawassie Island is a true Lowcountry gem that blends timeless charm with modern sophistication. Every detail has been thoughtfully curated in this top-to-bottom transformation, showcasing high-end finishes, designer touches, and quality craftsmanship throughout. The well-designed floor plan offers comfortable, easy living and effortless flow for entertaining, while the stunning updated kitchen serves as the heart of the home with premium appliances, custom cabinetry, and elegant surfaces. The spacious primary suite provides a serene retreat, complemented by beautifully renovated baths that evoke a spa-like experience. Additional guest rooms offer comfort and privacy, and the third bedroom offers flexibility as an ideal home office or study. Extending across the entire back of the home, an oversized screened porch creates the perfect setting for relaxing or entertaining while enjoying the peaceful Lowcountry surroundings. Significant upgrades provide added value and peace of mind, including all new windows, new HVAC system, and new hot water heaters. Nestled on a quiet cul-de-sac, the property offers a tranquil setting with inviting outdoor spaces to enjoy the natural beauty of Callawassie Island. Ideally located just moments from the River Club, deep water docks, and family pool, this home provides easy access to some of the community's most sought-after amenities. This move-in-ready home presents a rare opportunity to own a fully renovated residence in one of the Lowcountry's most desirable private communities, known for its championship golf, deepwater access, and exceptional amenities.

5 Oyster Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

4 Bent Tree Lane, Okatie
$900,000
4 Beds ⋅ 4 Baths ⋅ 3,925 SqFt. ⋅ HILTONHEAD-507539 MLS
Set agаinst a brеаthtakіng Ꮮοwcοuntrу backdrop, this stаtelу 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.

64 Osprey Circle, Okatie
$700,000
3 Beds ⋅ 4 Baths ⋅ 2,580 SqFt. ⋅ HILTONHEAD-504968 MLS
Experience the romance of Lowcountry living on Callawassie Island. Tucked beneath towering pines on a quiet, private homesite, this 2,580 sq ft home offers 3BR/3BA plus a dedicated office and captivating lagoon-to-golf views. A classic brick stairway leads to an expansive, columned front porch-rocking-chair ready and cooled by ceiling fans-setting the tone for slow mornings, sweet tea afternoons, and sunset conversations. Inside, enjoy light-filled living spaces and a gourmet kitchen built for gathering, featuring custom cabinetry, stainless appliances, a professional-style gas range with statement hood, and an oversized granite island with sink and abundant storage. The spacious primary suite is a true retreat with tranquil views and a spa-inspired bath with dual vanity, soaking tub, and separate shower. Two additional bedrooms and baths provide comfort and flexibility for guests. Out back, the screened porch and patio deliver the quintessential Lowcountry backdrop-breezes through the trees, birdsong overhead, and front-row vistas across the lagoon to the fairway beyond. Callawassie Island's gated community elevates the lifestyle with an exceptional club experience, including golf, tennis, fitness, pool, dining, and miles of protected marsh and waterways.

64 Osprey Circle, Okatie

Listing courtesy of Charter One Realty.

4 Chechessee Circle, Okatie
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 2,791 SqFt. ⋅ HILTONHEAD-502916 MLS
Discover the pinnacle of Lowcountry living in this brand-new, 4-bed, 3.5-bath marsh front home by Sumerall Custom Construction. Sited on a quiet street and framed by 10 majestic live oaks, this 2,800-sq-ft heated home (4,139 total under roof) is a masterpiece of design and efficiency.The interior impresses with soaring ceilings, 8-foot solid core doors, custom crown molding, and engineered wood floors. The open living area, anchored by a gas fireplace, flows seamlessly to a screened porch overlooking the tranquil marsh.The gourmet kitchen is an entertainer's dream, featuring stunning quartzite countertops, Thermadore panel-ready appliances, and an island ice maker. A separate scullery with a beverage fridge and drawer microwave adds ultimate convenience.Retreat to the main-floor primary suite, offering a spa-like bath and an extraordinary 146-sq-ft custom walk-in closet with pocket door access to the large laundry room. Every bedroom includes a custom walk-in closet. A massive finished room over the oversized 2-car garage serves as a private fourth bedroom or guest suite, complete with a full bath.Built for resilience, the home is fortified with impact windows, full encapsulated spray foam, and a high-efficiency Trane 17 Seer HVAC system.This property is your invitation to the exclusive Callawassie Island lifestyle. As SC's first "Community Wildlife Habitat," residents enjoy world-class amenities, including 27-hole Tom Fazio championship golf course, two clubhouses and six har-tru tennis courts, pools, a fitness center, and pickleball courts, water docks for boating, fishing, and kayaking.All this is just minutes from Beaufort, Bluffton, and Hilton Head. Experience meticulous craftsmanship in a serene setting. Currently under construction with an expected finish in January 2026, offering the opportunity to enjoy a brand new Lowcountry home in the new year. OSCREA

4 Chechessee Circle, Okatie

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

4 Heron Point, Okatie
$975,000
4 Beds ⋅ 3 Baths ⋅ 3,250 SqFt. ⋅ HILTONHEAD-504516 MLS
SELLER OFFERING TO CONTRIBUTE TO COMMUNITY ENHANCEMENT FEE WITH ACCEPTABLE OFFER. Encircled by lush maritime forests between the Dogwood course and the marshland stretching toward Spring Island, 4 Heron Point is a 4-bedroom cottage style home that speaks to the natural beauty and grandeur of Callawassie Island. The open living space at the heart of the home exults in airy cathedral ceilings above a great room boasting wide-plank pine flooring, carefully crafted custom built-ins and a wide fireplace surrounded by intricate woodwork. Open to the great room, the chef's kitchen masterfully blends form and function with alder wood cabinets, wide granite center island complementing the granite backsplash, updated stainless steel appliances and a massive pantry. This effortless flow, coupled with the whole-home sound system, sets the stage for unforgettable entertaining. Formal dining nearby surrounds you with refined shiplap walls and custom light fixtures, bathed in light from tall windows out to the Lowcountry porch. Through wide screens, this year-round outdoor living space soaks in panoramic views through the forest to the 6th hole on the Dogwood Course, with fans and heaters for comfort in every season. Along with these grand spaces, the home's layout allows for several more intimate spaces for solitude and quiet reflection. A stately office off of the main living space wraps you with gorgeous arched built-ins and views of the front entry, embodying old-world formality. A larger flex space above the two-car garage provides the opportunity to create a secluded office space, media room, home gym or guest suite with its full bath. Capped by a soaring geometric tray ceiling, the primary suite indulges with a sublime sense of space and luxe amenities from a massive walk-in closet to a spa-like en suite with tile-lined garden tub, wide granite-topped dual-basin vanity and corner walk-in shower. The ground floor also holds the home's three bedrooms, each with its own luxurious amenities. Along one wing of the home, a pair of bedrooms shares access to a full bath with tub and shower, each enjoying wide closets and elegant spaciousness. The rear bedroom even enjoys its own peaceful sunroom gazing out toward the golf views. With each space, this property offers a fresh interpretation of the sophisticated rusticism that sets Callawassie Apart. Elegant and refined in its appointments, but built in harmony with unspoiled nature.

4 Heron Point, Okatie

Listing courtesy of Maxey Blackstream Christie's International Real Estate. Selling Office: Coastal Real Estate Solutions II.

2 Chechessee Circle, Okatie
$875,000
4 Beds ⋅ 3 Baths ⋅ 2,833 SqFt. ⋅ HILTONHEAD-503950 MLS
Privately positioned on a secluded corner lot with sweeping marsh views, this Callawassie Island home offers 4 bedrooms and 3 bathrooms with the added peace of mind of a brand new roof. The open floor plan captures expansive marsh views while maximizing natural light throughout. The first-floor primary suite overlooks the marsh and features a beautifully appointed bathroom. A bonus room with a full bath adds flexibility for guests or entertaining. Outdoor living shines with a private deck and hot tub where you can unwind and enjoy peaceful marsh views and exceptional privacy. Life on Callawassie Island is defined by world-class amenities, natural beauty, and a strong sense of community, offering an active and refined lifestyle.

2 Chechessee Circle, Okatie

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

29 Island Creek Drive, Okatie
$1,575,000
4 Beds ⋅ 5 Baths ⋅ 3,570 SqFt. ⋅ HILTONHEAD-504079 MLS
Designed for elevated coastal living and effortless entertaining, this custom residence is a masterclass in craftsmanship, scale, and thoughtful design. At its heart, a spectacular 21' x 41' Great Room seamlessly unites the living, dining, and kitchen spaces beneath a vaulted, beamed ceiling anchored by a gas fireplace. A dramatic 16-foot fully openable Andersen folding glass door dissolves the boundary between indoors and out, opening to a screened porch perfectly level with the main living space to create a true indoor-outdoor great room experience.The professional-caliber kitchen is both stunning and functional, centered around an expansive 9' island and outfitted with a full suite of Thermador appliances, including a refrigerator/freezer, double wall ovens, gas cooktop, drawer microwave, and dishwasher. Quartz countertops, a custom-built hood, designer tile backsplash, and a walk-in pantry elevate the space, while a dedicated wine refrigerator and sliding pass-through window provide seamless service to the outdoor grilling area.The screened porch itself is a showpiece, featuring retractable Phantom screens for unobstructed views, a vaulted ceiling, and a gas fireplace with a 200-year-old reclaimed barn mantel. Just beyond, the outdoor grill area includes a gas connection and stone counters for effortless entertaining.A private study sits behind frosted glass pocket doors, highlighted by a tray ceiling and shiplap red oak accent wall. The primary suite is a serene retreat, offering a tray ceiling, private terrace with sweeping sunrise views over the golf course, dual walk-in closets with custom built-ins, and a spa-inspired bath with soaking tub, dual vanities, and an oversized tiled shower.Two spacious first-floor guest suites, each accommodating king beds and featuring ensuite baths and shiplap accents, are thoughtfully separated for privacy. A well-appointed laundry room, owners' entrance, and oversized three-car garage with EV charging complete the main level. Upstairs, a large bonus room with private bath offers flexible living space, while an exceptional 500-square-foot conditioned storage room provides rare, full-height versatility. Additional features include, spray foam insulation, premium Andersen windows, wide-plank French oak floors, whole-house water filtration, and multi-zone HVAC, this home delivers luxury without compromise-designed for how people truly live.

29 Island Creek Drive, Okatie

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

1 Tabby Point Lane, Okatie
$1,622,500
5 Beds ⋅ 5 Baths ⋅ 3,812 SqFt. ⋅ HILTONHEAD-503120 MLS
Discover Lowcountry living at its finest on highly sought-after Tabby Point. Perfectly positioned on one of Callawassie Island's larger marshfront lots, this home captures sweeping views stretching from the tranquil marsh straight to the river. Set back from the street for added privacy, it also features a very large backyard, offering space rarely found in marshfront living. Whether you're savoring a quiet morning coffee or hosting at sunset, the vistas here are truly unmatched.The heart of the home is a chef's kitchen, offering extensive counterspace, abundant storage, and cabinetry that extends to the ceiling-ideal for cooking, entertaining, and everyday use. A large porch off the main living area invites you to relax outdoors while taking in the coastal scenery. Inside, a stunning custom oyster shell fireplace with a reclaimed mantle and matching shelves serves as a true focal point, adding warmth and Lowcountry character. The home also features a unique in-wall aquarium that can be enjoyed from two rooms, creating a beautiful and calming visual connection throughout the living space.The main level includes a spacious guest suite featuring a jacuzzi tub and walk-in closet, providing privacy and comfort for visitors. Upstairs, the primary suite becomes a private retreat with its own screened-in balcony overlooking the marsh-a peaceful place to unwind and enjoy the breezes. A convenient kitchenette is also located on the second floor, offering added comfort and functionality for the primary suite and upper-level living.This home offers exceptional flexibility with laundry rooms on both levels; the downstairs laundry space can also serve as a wine room or back kitchen depending on your needs. Ample storage runs throughout the property.Outside, enjoy a firepit area and a floating dock perfect for launching kayaks or paddleboards, allowing effortless access to the surrounding waterways right from your backyard. A 2-car garage plus an oversized golf cart garage ensures plenty of room for vehicles, recreational gear, and workshop space.With its rare lot size, elevated views, and thoughtful layout, this home delivers an exceptional island lifestyle paired with the comforts of country club living. Callawassie Island amenities include 2 pools, 2 deep-water docks, 2 community kayak/crabbing docks, pickleball, tennis, bocce, 27 holes of championship golf, multiple dining options, and a fully equipped fitness center.Owner is a SCREA.

1 Tabby Point Lane, Okatie

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

67 Osprey Circle, Okatie
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 2,406 SqFt. ⋅ HILTONHEAD-502817 MLS
Welcome to luxurious Lowcountry living in this stunning brand-new construction home by Artisan Custom Homes located on the serene and sought-after Callawassie Island. Thoughtfully designed to blend modern comfort with timeless coastal charm, this residence offers an exceptional lifestyle surrounded by natural beauty, world-class amenities, and the relaxed elegance of island living. Set on the quiet, picturesque Osprey Circle, the home welcomes you with sweeping views of mature live oaks, palmettos, and the island's protected natural landscape. Step inside to an open and airy floor plan featuring high ceilings, abundant natural light, and refined architectural details throughout. Expansive living and dining spaces flow effortlessly into a chef-inspired kitchen-ideal for both everyday enjoyment and effortless entertaining. The primary suite provides a peaceful retreat with spa-style comforts and tranquil views, while additional guest rooms offer privacy and flexibility for family or visitors. Outdoor living shines with a spacious screened porch with fireplace, perfect for morning coffee, evening breezes, or simply enjoying the island's abundant wildlife. Callawassie Island is renowned for its unmatched lifestyle-27 holes of Tom Fazio golf, top-tier tennis and pickleball facilities, two resort-style pools, deep-water docks, a state-of-the-art fitness center, and vibrant community events. With 24-hour security and breathtaking riverfront scenery, it's a place where nature, community, and luxury come together. This exceptional new home at 67 Osprey Circle offers the rare opportunity to experience the best of coastal South Carolina in a brand-new, move-in-ready residence.

67 Osprey Circle, Okatie

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

9 Winding Oak Drive, Okatie
$500,000
3 Beds ⋅ 3 Baths ⋅ 2,398 SqFt. ⋅ HILTONHEAD-502567 MLS
Welcome to Callawassie Island, a private gated island sanctuary community with numerous amenities. With a new roof, this spacious 3 bedroom, 2.5 bath one level is perfectly framed by sweeping views of Spanish moss-draped oaks and the Tom Fazio "Palmetto" course. Sunlight filters through generous windows, illuminating architectural details. With vaulted ceilings and a wall of windows, the inviting great room is anchored by the fireplace. Entertaining is easy with the spacious dining area open to the kitchen. The kitchen showcases custom wooden cabinetry and a walk-in pantry. The tranquil primary suite overlooks the wide views and offers a jetted spa tub, walk-in shower and dual vanities. A large two car garage with a dedicated golf cart bay, this home is priced for you to add your personal touches.

9 Winding Oak Drive, Okatie

Listing courtesy of Keller Williams Realty. Selling Office: William Raveis - Carolina LLC.

26 Heron Walk, Okatie
$450,000
3 Beds ⋅ 2 Baths ⋅ 1,861 SqFt. ⋅ HILTONHEAD-502715 MLS
26 Heron Walk stands out as one of the largest villas in the Village section, offering 1,861 sq ft of thoughtfully designed living space. This inviting home features a large Carolina Room and a detached full garage with golf-cart bay. Designed for comfort and flexibility, it offers open living areas and exceptional privacy with serene lagoon and golf-course views. Upstairs, the beautifully updated second-story bath has been used as a primary suite during current ownership, enhancing the home's versatility and livability. New Roof-2026. Located within the private, gated community of Callawassie Island, residents enjoy access to newly renovated Tom Fazio-designed golf courses, deep-water access, club dining, fitness facilities, pools, tennis, pickleball, bocce, and more. Life on Callawassie Island offers an unmatched blend of natural beauty, community connection, and the timeless charm of Lowcountry living.

26 Heron Walk, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

61 Winding Oak Drive, Okatie
$865,000
3 Beds ⋅ 3 Baths ⋅ 2,435 SqFt. ⋅ HILTONHEAD-502431 MLS
Newer construction, refined Lowcountry design, and future expansion potential come together at 61 Winding Oak Drive, a 2024 custom-built home on prestigious Callawassie Island. Positioned on an elevated homesite along the newly renovated Magnolia Golf Course, this bright one-level residence offers privacy, quality, and an unusually versatile layout for buyers who want ease of living today with room to grow tomorrow.A tabby driveway with brick apron sets the tone, while the front porch captures a glimpse of the river just across the street. Inside, natural light highlights French oak floors, cottage-style trim, custom window treatments, and a crisp, timeless palette. The open-concept living area features vaulted ceilings, a gas fireplace, and seamless flow into the kitchen and dining spaces.The kitchen was designed to both impress and perform, with abundant cabinetry, and a butler's pantry that adds charm, storage, and everyday function. The main level includes 3 bedrooms, 2.5 baths, a dedicated home office, and a heated/cooled storage room that could serve as a second office, hobby room, fitness space, or additional flex area.One of the most compelling features is the expansive walk-up attic space. Already offering substantial storage, lighting, this area presents a valuable opportunity for future finished living space, a bonus room, guest suite, studio, media room, or potential 4th bedroom configuration, subject to permitting. In a market where many buyers want newer construction but hesitate over limited bedroom count, this home offers a rare path to added functionality without sacrificing the convenience of one-level living.The primary suite is a true retreat with two closets featuring custom solid wood built-ins and a well-appointed bath. Outdoor living is equally inviting with a screened porch, large patio with pergola, and a spacious backyard ideal for relaxing, entertaining, or enjoying the peaceful golf-course setting.Additional highlights include an oversized 2 car garage with golf cart bay and a tankless Rinnai water heater. Beyond the home, Callawassie Island offers an exceptional private island lifestyle with golf, tennis, pickleball, fitness, deepwater access, dining, and a vibrant social scene surrounded by the natural beauty of the Lowcountry.

61 Winding Oak Drive, Okatie

Listing courtesy of Coldwell Banker Access Realty. Selling Office: Peirce Group Brokered by EXP Realty LLC.

27 River Marsh Lane, Okatie
$1,345,000
4 Beds ⋅ 4 Baths ⋅ 2,860 SqFt. ⋅ HILTONHEAD-501726 MLS
Newly сompletеd 4 Βedrοοm/3.5 Βath, Cаllаwassie Islаnd Club Cottаge, 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.

3 Woodstork Watch, Okatie
$1,350,000
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.

56 Spring Island Drive, Okatie
$1,075,000
4 Beds ⋅ 5 Baths ⋅ 3,460 SqFt. ⋅ HILTONHEAD-500696 MLS
Situated with a panoramic view of the golf course, this Lowcountry style custom home is surrounded by majestic oaks & blooming magnolias. Home has a large primary suite and two bedrooms on the first floor. A finished suite over the garage offers privacy and comfort for guests. A charming screened porch provides an escape to relax or for entertaining. Home is detailed with Andersen windows, reclaimed pine floors, and custom cabinetry. Freshly painted throughout. Renovated kitchen with adjacent breakfast area and family room. New paver patio and built in grill. Two tankless hot water heaters. HVAC 2017 main house. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. 6 tennis courts, pickleball courts, Bocce courts, dog park, 27 hole Golf course & 24/7 gated security.

56 Spring Island Drive, Okatie

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

21 Osprey Circle, Okatie
$900,000
4 Beds ⋅ 5 Baths ⋅ 3,543 SqFt. ⋅ HILTONHEAD-450920 MLS
Welcome to Southern elegance at its finest! Nestled on a private and serene 0.80-acre lot, this stately custom Lowcountry home is the perfect blend of charm, comfort, and sophistication. The main residence offers 3 bedrooms and 3.5 bathrooms, while a beautifully appointed guest cottage provides an additional 1 bedroom and 1 bathroom ideal for visitors or multi-generational living. Designed with entertaining in mind, the open and airy layout features a chefs kitchen, formal dining room, and a spacious family room with a dual-sided gas fireplace that flows seamlessly into the great room. The first-floor primary suite is a true retreat, complete with a luxurious en-suite bath and a generous walk-in closet. Step outside to a covered porch perfect for morning coffee or evening gatherings, all surrounded by lush landscaping and upscale custom finishes throughout. Experience the best of island living and take advantage of the premier amenities this sought-after community has to offer. Schedule your private tour today this is Lowcountry living at its finest! *Seller will pay half of HOA initiation with accepted offer*

21 Osprey Circle, Okatie

Listing courtesy of Redfin Corporation. Selling Office: Charter One Realty.

7 Winding Oak Court, Okatie
$2,100,000
5 Beds ⋅ 7 Baths ⋅ 5,259 SqFt. ⋅ HILTONHEAD-447631 MLS
New construction on very private lot overlooking the Colleton River with gorgeous southern exposure. Tons of space including 1st floor primary suite, light-drenched kitchen that opens to living room and breakfast nook, formal dining room and office. Second floor features 3 bedrooms with bath en suites, plus den. Huge top floor with separate bath offers great flex space with tons of creative options. Don't miss the carriage apartment located above the spacious 3-car garage. Callawassie Island is a private Sea Island gem offering extraordinary golf, deep water dock access, fitness center, racquet facilities, club house, river club and 2 pools.

7 Winding Oak Court, Okatie

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

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