Callawassie Island Homes with Pickleball Amenities

Welcome to Callawassie Island, a hidden gem nestled in the heart of Beaufort County, South Carolina. This picturesque island community, located in the charming city of Okatie, offers a harmonious blend of natural beauty and refined living. Surrounded by lush landscapes and serene waterways, Callawassie Island is not just a place to live; it's a lifestyle.

For those who enjoy an active lifestyle, Callawassie Island is a haven for pickleball enthusiasts. The community boasts homes equipped with pickleball amenities, ensuring that residents can engage in this popular sport right at their doorstep. Whether you're a seasoned player or a newcomer eager to learn, the vibrant pickleball scene fosters camaraderie and friendly competition among neighbors.

The homes in Callawassie Island reflect a commitment to quality and elegance, with many properties featuring stunning views, spacious layouts, and modern finishes. Residents enjoy access to a wealth of community amenities, including walking trails, golf courses, and social clubs, all designed to enhance the living experience.

Living in Callawassie Island means embracing the tranquility of coastal living while being just a short drive from the cultural and culinary delights of Beaufort and Hilton Head Island. Experience the perfect blend of leisure and luxury as you explore the beautiful homes with pickleball amenities that await you in this enchanting community. Discover your dream home in Callawassie Island, where every day feels like a vacation!

Newest Callawassie Island Homes with Pickleball Amenities

$715,000

3 Beds ⋅ 3 Baths ⋅ 2,175 SqFt. ⋅ 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 ⋅ 3,103 SqFt. ⋅ 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.

$1,475,000

4 Beds ⋅ 4 Baths ⋅ 3,554 SqFt. ⋅ 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 ⋅ 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.

$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.

$1,100,000

3 Beds ⋅ 4 Baths ⋅ 3,148 SqFt. ⋅ HILTONHEAD-509010 MLS

Incredible riverfront opportunity with breathtaking long-range views of tidal marsh to the Colleton River. Enjoy generous outdoor entertaining areas and an incredible 180-degree panoramic view. The spacious 15' x 12' viewing deck provides the perfect place to gather with friends, watch the changing tides, and take in spectacular sunsets and coastal breezes. Nestled on a private 1.29-acre cul-de-sac lot, the property offers a desirable one-level floor plan with 3,292 square feet, 3 bedrooms, and 3.5 baths. Situated on high ground within an X-500 flood zone, this home awaits a new owner's vision to transform it into a truly exceptional waterfront retreat. Recent improvements include two new HVAC systems (2025) and a roof installed in 2016. Private dock potential exists, subject to current permitting requirements and approvals. A truly special setting offering privacy, deep-water views, and the opportunity to create your dream Lowcountry waterfront lifestyle. Residents enjoy the unmatched lifestyle of Callawassie Island-an engaging community, remarkable natural beauty, top-tier golf and amenities, endless outdoor activities, and the peace of mind that comes with gated security and true Lowcountry privacy. Seller to provide buyer with a $75,000 Credit, at closing, towards repairs, re-piping or Contribution Fee, with an acceptable offer.

5 Shellfish Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$385,000

3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-509585 MLS

Nestled within the private gated community of Callawassie Island, 24 Heron Walk offers Lowcountry living at its finest. This beautifully maintained 3-bedroom, 2-bath townhome features stunning lagoon views from both the front and back, along with picturesque golf course views. The remodeled 2023 kitchen is a true showpiece, highlighted by a premium Hallman Cookers professional range imported from Italy. Enjoy cozy evenings by the wood-burning fireplace and the peaceful natural surroundings that make this home so special. Residents enjoy exceptional amenities including 3 upgraded golf courses with over $8 million in recent improvements, two clubhouses, two restaurants, two pools, new pickleball courts, croquet and bocce ball, massage and therapy rooms, a library, boat docks, and separate dog parks for large and small dogs. Seller offering $52,000 towards Callawassie Island buy-in.

24 Heron Walk, Okatie

Listing courtesy of ERA Southeast Coastal.

$399,000

3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-509257 MLS

Enjoy island living in this beautifully updated 3 bedroom with primary on the first floor 2 bath villa in the gated Callawassie Island community. Recent improvements include a 2020 roof, 2022 HVAC, updated kitchen with new granite countertops & backsplash, induction stove & microwave (2023), plus new windows, flooring and new upstairs bath. Exterior painted in 2024 & decks painted in 2026. Screened porch. Golf cart garage included for easy community access & coastal lifestyle convenience. Callawassie Island is a 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.

20 Heron Walk, 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.

$1,899,900

4 Beds ⋅ 5 Baths ⋅ 4,470 SqFt. ⋅ 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.

$1,285,000

3 Beds ⋅ 4 Baths ⋅ 3,512 SqFt. ⋅ HILTONHEAD-508587 MLS

Nestled within one of the most scenic settings on Callawassie Island, this exceptional custom-built Lowcountry home captures miles of sweeping marsh, river, and golf views, all paired with incredible sunsets and refreshing summer breezes. Thoughtfully designed to embrace its stunning surroundings, the home offers expansive porches and decks that create a seamless indoor-outdoor living experience. Crafted with timeless quality and architectural character throughout, features include a lifetime metal roof, 10-foot ceilings, Pella windows and doors, reclaimed Southern pine flooring, 8-foot solid core doors, and extensive custom cabinetry and built-ins. The beautifully appointed designer kitchen showcases limestone and granite countertops, a gas cooktop, and refined finishes ideal for both everyday living and entertaining. Additional details such as crown molding throughout the first floor and oil enamel painted casework and doors further elevate the home's craftsmanship and warmth. The spacious second-floor bedroom retreat includes a private sitting room, while the detached garage offers a beautifully designed guest suite complete with its own kitchenette-ideal for visitors, multigenerational living, or private workspace flexibility. Residents enjoy the unmatched lifestyle of Callawassie Island-a private gated island community known for its remarkable natural beauty, welcoming atmosphere, deep-water access, top-tier golf and amenities (optional), endless outdoor recreation, and the peaceful charm of true Lowcountry living.

10 Island Creek Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$2,995,000

5 Beds ⋅ 5 Baths ⋅ 3,906 SqFt. ⋅ HILTONHEAD-508380 MLS

A different rhythm takes hold at Callawassie Island, a canopy 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.

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