Callawassie Island Homes with Pickleball Association Amenities

Welcome to Callawassie Island, a hidden gem nestled in the heart of Beaufort County, South Carolina. This picturesque subdivision in Okatie seamlessly blends natural beauty with a vibrant community spirit, making it the perfect place to call home. Surrounded by lush landscapes and serene waterways, Callawassie Island offers a tranquil retreat while remaining conveniently close to the charming amenities of the Lowcountry.

One of the standout features of this delightful community is its commitment to an active lifestyle, epitomized by the Pickleball Association amenities. Whether you're a seasoned player or new to the game, you'll find a warm and welcoming atmosphere here. The well-maintained pickleball courts provide an excellent opportunity for friendly competition and social interaction, fostering connections among neighbors of all ages. Imagine spending your afternoons engaged in spirited matches, followed by laughter and camaraderie with fellow residents.

In addition to pickleball, Callawassie Island boasts a host of other amenities designed to enhance your living experience. Residents can enjoy scenic walking trails, community gatherings, and access to pristine outdoor spaces that celebrate the natural beauty of the region. With a focus on wellness and community engagement, Callawassie Island truly offers a lifestyle that balances relaxation and recreation.

Explore the charming homes within this subdivision, where modern elegance meets Southern charm. Each residence is thoughtfully designed to maximize comfort and style, providing the perfect backdrop for creating lasting memories. Come discover the allure of Callawassie Island, where your dream home awaits amidst a vibrant community dedicated to an active and fulfilling lifestyle.

Newest Callawassie Island Homes with Pickleball Association Amenities

$899,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512221 MLS

Better than new and truly one-of-a-kind, this artisan-crafted former model home offers an exceptional blend of luxury, privacy, and Lowcountry living. Located in the desirable Oyster Cay on Callawassie Island, tucked away on an oversized, serene wooded lot, the residence feels exceptionally peaceful and private while being just down the street from the River Club, Family pool and deep-water boat docks. Thoughtfully designed and meticulously maintained, the home showcases an impressive collection of custom upgrades and designer finishes, including multiple shiplap accent walls, an extensive custom trim package, Hunter Douglas shades, a tankless water heater, and spray foam insulation, along with countless other refined details. An indoor gas fireplace creates a warm and inviting gathering space, while the spacious screened porch, with its inviting outdoor gas fireplace provides a beautiful year-round setting for relaxing, dining, and enjoying the tranquil natural surroundings. Everyday comfort and convenience have been equally considered, with a whole-home generator and EV charger providing modern functionality and peace of mind. The spacious floor plan, elevated craftsmanship, and impeccable model-home presentation make this residence feel almost new-yet it already includes the custom upgrades and finishing touches that are typically added over time. Beyond the home, Callawassie Island offers an exceptional Lowcountry lifestyle, with Tom Fazio-designed golf, tennis, pickleball, pools, a fitness center, boating, and more, all set within a beautiful private island environment. Ideally located in Beaufort County, the community provides convenient access to Beaufort, Port Royal, Bluffton, Hilton Head Island, Charleston and Savannah, while preserving the privacy, natural beauty, and tranquility that make island living so special.

226 Callawassie Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,395,000

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-512044 MLS

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 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 firepit, 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 dedicated golf cart bay and epoxy floors is topped by a 558-square-foot FROG with 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.

$1,379,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512149 MLS

Tucked beneath a canopy of trees on desirable Osprey Circle, mid-island in Magnolia #7, this home feels like a private retreat, completely redesigned and rebuilt from the studs by a premier contractor, with no expense spared and no detail overlooked. Eastern exposure fills the home with soft morning light, while shaded afternoons and a long, private view of the golf course create a quiet, elevated sense of place.Essentially reborn as a new home, the residence was reconstructed with all-new stucco and exterior painting, all-new electrical, and all-new plumbing throughout. The interior showcases gorgeous segmented arches throughout, offering beautiful architectural character alongside 8' solid-core doors and hardwood flooring laid with laser precision. A redesigned hallway flows through graceful new archways into the kitchen and dining room, where custom wainscoting lends a refined, tailored finish. The kitchen is anchored by Taj Mahal quartzite countertops, while the spa-inspired bathrooms are finished in quartz, with redesigned tile showers and a master suite featuring a freestanding pedestal tub and brass fixtures.The Carolina room has been thoughtfully redesigned to frame the wooded, golf-course backdrop, with new screening and a glass door that blurs the line between indoors and out. Additional refinements include a butler's pantry with dry-bar and wine cooler, hurricane-impact windows, a tankless water heater, blown-foam attic insulation, and a fully restuccoed, stone-accented exterior complemented by newly curated landscaping.For the buyer who values craftsmanship and quality above all, this is a rare offering: a true turnkey residence where every element has been considered. Move in with complete peace of mind and begin your Callawassie Island Lifestyle.

90 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,075,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511584 MLS

Among the Best Golf/Marsh views within Callawassie Island. This Club Cottage, at 2,965 sq. feet, has 4 bedrooms, 3 1/2 bath and terrific long views of the complete Dogwood 9th hole, bridge/lagoon and tidal marsh views. Primary Bedroom on 1st floor, with 2 bedrooms upstairs with an optional 4th bedroom or office. The Upstairs Bedroom private veranda provides even more elevated spectacular views. Callawassie Island Club Cottage Section is ideal for either a primary home, a 2nd home or a rental investment property. Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

24 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$715,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511821 MLS

Beautifully updated one-level ranch overlooking the prestigious Magnolia #5, this exceptional home offers effortless slab-on-grade living in the heart of Callawassie Island. Meticulously maintained and move-in ready, it is perfectly suited as either a full-time residence or an idyllic Lowcountry retreat. Thoughtfully enhanced throughout, the home interior features a designer kitchen with new appliances, new ceiling fans and light fixtures, new Hunter Douglas plantation shutters, and fresh interior paint. The exterior offers new gutters with gutter guards, new exterior light fixtures, copper rain chains, elegant new front entry doors, decorative crosshead window moldings plus more, creating a timeless blend of style and functionality. The inviting Carolina Room serves as a peaceful year-round extension of the living space, overlooking a completely redesigned backyard with lush landscaping that provides a private setting for relaxing or entertaining. Beautifully landscaped from front to back, every detail reflects pride of ownership and exceptional care. Located within the private, gated community of Callawassie Island, residents enjoy an unparalleled lifestyle with 27 holes of Tom Fazio-designed championship golf, tennis, pickle ball, fitness facilities, community docks, swimming pools, dining, and miles of breathtaking marsh front scenery. Ideally situated between Beaufort, Bluffton, Hilton Head, and Savannah, this remarkable home offers the perfect combination of privacy, luxury, and convenience. Furnishings and Golfcart are negotiable.

89 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,100,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-510836 MLS

Tucked at the end of a quiet cul-de-sac and shared by only four residences, this Classic Lowcountry-style home offers a rare combination of privacy, pedigree, and place. Originally built by Steve Tilton of Coastal Signature Homes, the residence reflects the craftsmanship and thoughtful detailing this builder is known for, from refined millwork to finishes selected with an eye for timeless quality.The setting is equally exceptional. Recently expanded to 1.09 acres, the property is canopied by mature Live Oaks and offers partial marsh views, creating a sense of seclusion that's increasingly rare to find. With only three neighboring homes on the entire street, this feels less like a residential lot and more like a private retreat, the kind of privacy that simply can't be recreated.This is Lowcountry living at its most authentic: classic architecture, masterful construction, and a setting defined by nature, quiet, and space to breathe.

6 Winding Oak Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,350,000

4 Beds ⋅ 5 Baths ⋅ 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.

$1,475,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-510537 MLS

TAKING BACK UP OFFERS! Built in 2015 by renowned custom builder Steve Tilton, owner of Coastal Signature Home, this impeccably maintained coastal residence offers over 3,554 square feet of thoughtfully designed living space overlooking breathtaking panoramic views of Chechessee Creek and the surrounding marshlands. Indirect sunrise and sunset views create an incredible opportunity to enjoy Callawassie Island at its very best! With three spacious bedrooms on the main level, this beautiful home offers easy one-level living. Perfectly positioned on a private cul-de-sac with desirable northeastern exposure, this four-bedroom, three-and-a-half-bath home seamlessly blends timeless craftsmanship with modern comfort. Rich architectural details and exquisite millwork are showcased throughout, while random-width reclaimed pine flooring adds warmth and character to the home's elegant interiors. Designed to maximize its spectacular setting, the living room, kitchen, breakfast nook, family room, primary bedroom, and guest bedroom all enjoy direct water and marsh vistas. The home features both formal and casual living spaces, including inviting formal living and dining rooms, in addition to an expansive open-concept family room and kitchen. The soaring 16-foot vaulted ceiling creates a dramatic focal point, while the chef's kitchen is appointed with premium appliances, a gas cooktop, and a refrigerator replaced in 2025. Outdoor living is equally impressive. A 400-square-foot screened porch with a gas fireplace provides the perfect setting for year-round enjoyment, whether entertaining guests or simply taking in the tranquil waterfront scenery and wildlife activity. A significant enhancement completed in October 2024 added a spacious 536-square-foot bonus room with a full bath and beautifully finished ceramic tile shower, offering exceptional flexibility for guests, a home office, media room, or private retreat. Additional features include a tankless water heater, a spacious walk-up attic with spray foam insulation for energy efficiency and abundant storage, as well as an insulated crawl space. The exterior was freshly painted in May 2026, adding to the home's appeal and maintenance value. Offering exceptional craftsmanship, stunning natural views, and move-in-ready condition, this remarkable custom home presents a rare opportunity to enjoy refined Lowcountry living at its finest.

12 Dolphin Lane, Okatie

Listing courtesy of Charter One Realty.

$1,150,000

3 Beds ⋅ 4 Baths ⋅ 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.

$1,395,000

3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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.

$1,899,900

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-508950 MLS

Brand-new custom luxury Lowcountry retreat nestled near the end of the peninsula on a quiet, private wooded cul-de-sac in desirable Woodstork Watch on Callawassie Island, surrounded by similarly impressive high-end custom homes. This expansive newly constructed residence offers stunning high-tide marsh views and exceptional craftsmanship throughout, including energy-efficient 2x6 construction and spray foam insulation. Designed to embrace the Lowcountry lifestyle, the home features seamless indoor and outdoor living transitions on both the first and second levels, creating inviting spaces for entertaining and relaxation. Soaring cathedral ceilings enhance the open and airy feel of the main living spaces, while sophisticated custom black steel railings add striking architectural detail throughout the home. The gourmet JennAir kitchen is designed for entertaining with a massive center island, six-burner gas range, premium appliances, and an elegant scullery for added prep and storage space. An expansive upstairs loft with private balcony captures peaceful marsh views and offers additional living and gathering space. A full private living area above the garage with its own kitchenette provides ideal space for guests, extended family, or multigenerational living. Enjoy refined finishes, modern luxury, and the perfect blend of privacy and Lowcountry beauty in one of the island's most sought-after settings. Widely regarded as one of the premier locations in Beaufort County, Callawassie Island offers an exceptional Lowcountry lifestyle with convenient access to Beaufort, Bluffton, Hilton Head Island, and the historic cities of Charleston and Savannah.

7 Woodstork Watch, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

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