View All Callawassie Island SC Renovated Homes Listings

$1,395,000
3 Beds 3 Baths 3,549 SqFt. HILTONHEAD-508583 MLS
Exceptional custom-built home showcasing unique golf and lagoon views across the entire Magnolia #5 hole on Callawassie Island's beautifully renovated Tom Fazio course. Thoughtfully designed to embrace its stunning setting, this move-in-ready residence offers the perfect opportunity to begin enjoying Lowcountry island living from day one.The open-concept floor plan is filled with natural light, highlighted by soaring ceilings, expansive windows, and generous crown molding throughout. Refinished and stained heart pine floors add warmth and character, while the Great Room features a fireplace and custom built-ins, creating an inviting space for everyday living and entertaining.The gourmet kitchen is beautifully appointed with all newer (2024) Thermador stainless steel appliances, a six-burner gas cooktop, granite countertops, and distinctive Italian glazed cabinetry. The primary suite serves as a private retreat with elegant marble and porcelain tile finishes and a custom-designed closet.Recent improvements provide exceptional value and peace of mind, including all three HVAC systems replaced in 2024, newer washer and dryer, refinished heart pine flooring, refinished mahogany front door, and three new garage door openers. Upper-level furnishings may convey with limited exclusions, creating a turnkey opportunity for the next owner.Outdoor living is equally impressive, with a spacious deck and screened porch perfectly positioned to capture panoramic golf and lagoon views, cooling marsh breezes, and unforgettable sunsets. Whether enjoying a quiet morning coffee or entertaining friends after a day on the course, these spaces embody the best of Lowcountry living.Beyond the home, Callawassie Island offers an unmatched private island lifestyle with 27 holes of championship golf, deep-water docks, two clubhouses, fitness and wellness facilities, tennis, pickleball, swimming pools, walking trails, and a vibrant social atmosphere-all within a gated island community surrounded by breathtaking natural beauty.This is more than a home; it's an opportunity to embrace one of the Lowcountry's most sought-after island lifestyles.

113 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$946,900
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, the residence features expansive windows that flood the home with natural light while showcasing the stunning scenery from nearly every room. The spacious great room with cathedral ceilings and a cozy fireplace flows seamlessly into the Carolina room and updated kitchen, making the home ideal for entertaining or quiet relaxation. Recent improvements include new wide plank engineered oak floor coverings and a new HVAC system installed this year, adding both style and modern comfort throughout the home. The primary suite offers a serene escape with tranquil water views, beautifully renovated baths, and generous walk-in closets. Flexible living spaces provide options for a home office, formal dining room, or additional guest accommodations. Outdoor living is equally inviting, with a large deck perfect for enjoying morning coffee, evening sunsets, 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, pickle ball, fitness facilities, community docks, dining, pools, and miles of scenic marsh front beauty. Ideally positioned between Beaufort, Bluffton, Hilton Head, and Savannah, this home offers the perfect balance of privacy, luxury, and convenience.

8 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$865,000
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.

$798,000
3 Beds 3 Baths 2,591 SqFt. HILTONHEAD-507892 MLS
Located on desirable Osprey Circle, this beautifully maintained, single-level 3-bedroom home offers a move-in ready opportunity with thoughtful renovations throughout. Set among native hardwoods, magnolias, and palms, the property captures a true sense of serenity, enhanced by manicured gardens, natural surroundings, and great elevation-creating a setting that feels like a private retreat. The kitchen was fully renovated in 2025 and features new appliances, a custom-designed hood, large wine cooler, and an added coffee bar and pantry area, creating a functional and elevated space for both everyday living and entertaining. Interior updates include new paint, updated lighting fixtures throughout, new toilets, and new flooring in select areas. Additional improvements include a new vanity in the half bath (2024), a newly added second bathroom, an Aquasana water filtration system, and an LG washer/dryer tower.Outdoor living has been significantly enhanced with a new screened porch (2024), approximately 15.5 x 15.5, ideal for relaxing or entertaining. The exterior also features an enhanced front entry with added pavers, patio upgrades, expanded outdoor living space, and a newly designed backyard with all new plantings for increased privacy. A new driveway, refreshed landscaping, and irrigation updates complete the setting.This home offers a rare combination of quality updates, easy one-level living, and a prime location within Callawassie Island-perfect for those seeking both comfort and connection to the natural beauty of the Lowcountry.

15 Osprey Circle, Bluffton

Listing courtesy of Coastal Real Estate Solutions II.

$995,000
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.

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Callawassie Island, SC · Curated MLS Search

Renovated Homes in Callawassie Island, SC

An editorially curated view of every active renovated homes listing in Callawassie Island, SC. Updated in real time from the local MLS, presented without the noise.

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