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$6,500,000
5 Beds 9 Baths 8,362 SqFt. HILTONHEAD-502660 MLS
Experience the soul of Lowcountry living in this enchanting deep-water estate, where timeless Southern charm meets exceptional craftsmanship. A sweeping wraparound porch captures gentle river breezes and sets the stage for unforgettable sunrises and slow, breezy afternoons. Inside, soaring vaulted ceilings, abundant natural light, and warm, inviting finishes create an atmosphere of effortless elegance. The gourmet kitchen is perfect for gatherings, offering refined style and functionality. A spacious mother-in-law and beautifully appointed detached carriage house provide unmatched flexibility for guests or extended family. The oversized 4+ garage and generous walk out storage-with bathrooms-ensure space for every hobby, project, and coastal toy. A rare 4-stop elevator adds ease to daily living. On the river, a private deep-water dock awaits with an impressive 18,000 lb lift and a covered perch above the water-an idyllic spot to relax, unwind, and savor the beauty of the Lowcountry. Thoughtfully wired for a whole home generator, this estate blends comfort, luxury, and Southern grace in every detail.

107 Okatie Highway, Okatie

Listing courtesy of Collins Group Realty.

$1,100,000
2 Beds 3 Baths 1,585 SqFt. HILTONHEAD-503117 MLS
Surrounded by majestic Live Oaks and overlooking the 12th fairway of Old Tabby Links, this property offers a beautifully finished guest cottage and an elegant retreat. Take advantage of the cottages in place or expand and build your dream home on this expansive 1.96 acre lot. Both structures in place feature brick exteriors, custom mahogany doors, concrete tile roofs, and premium oak flooring. Recent enhancements include a fenced dog run and a screened porch. The two bedroom guest cottage offers baths finished in cream marfil and travertine, charming bedroom alcoves, a well equipped living area with under counter refrigerator and freezer, a brick accent wall, and a full size washer and dryer. The Retreat provides a refined escape with the flexibility to be an additional sleeping area with a full bathroom featuring exquisite paneling and trim, a wet bar, and views of the golf course. With a flat screen TV above the fireplace, it is an ideal place to relax and unwind.

30 Bee Tree Drive, Okatie

Listing courtesy of Spring Island Realty LLC.

$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.

$50,000
HILTONHEAD-502298 MLS
This large high and dry .505 acre homesite offers incredible views of multiple holes on the newly renovated Magnolia Course, and is situated on one of the highest elevated properties on Callawassie Island. 51 Winding Oak benefits from a direct view of the 3 Magnolia Green, as well as long views down the 4th fairway. Sale of this lot is contingent on the purchaser contracting for the construction of a home with Artisan Custom Homes and a one time $75,000 club initiation, which can be paid for at closing or added to the price of the home. During home construction the Purchaser will benefit and enjoy the full use of Callawassie Island's World Class Amenities, to include 27 Holes of Newly Renovated Tom Fazio Golf, Two Waterfront Clubhouses & Pools, Racquet sports, Four Community Docks & more with club dues waived throughout construction until home completion and a Certificate of Occupancy is established. Several plans to choose from within the Builder's Expansive Portfolio.

51 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,395,000
4 Beds 4 Baths 2,860 SqFt. HILTONHEAD-501726 MLS
Newly completed 4 Bedroom/3.5 Bath, Callawassie Island Club Cottage, 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.

$1,390,000
5 Beds 6 Baths 4,193 SqFt. HILTONHEAD-501620 MLS
Welcome to Callawassie Island, a private gated wildlife sanctuary 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.

$25,000
HILTONHEAD-454628 MLS
Imagine crossing the causeway each day and coming home to your own Lowcountry island retreat. Set on approximately .66 wooded acres and just one lot back from the river, 3 Shellfish Lane offers a rare opportunity to build in the serene, gated community of Callawassie Island. Mature trees, natural beauty, and the peaceful rhythm of island life create a setting that feels tucked away from the world-while still offering an exceptional lifestyle. Recognized as an Audubon Certified community, Callawassie Island offers a rare blend of refined amenities and laid-back Lowcountry charm. This is an opportunity for the buyer ready to build a meaningful home in one of the area's most distinctive private island settings. A beautiful home rendering is available to inspire what could be built on this special homesite by H2 Builders of Bluffton, one of the Lowcountry's premier luxury custom builders. The rendering is conceptual only, and the home is not included in the sale, but it offers a glimpse of the possibilities for creating a custom island retreat. Life on Callawassie Island is centered around luxury, nature, and connection. Residents enjoy 27 holes of Tom Fazio golf, tennis, pickleball, fitness facilities, pools, dining, boating, kayaking, fishing, and an active social calendar-all surrounded by tidal waters, moss-draped oaks, and abundant wildlife. Learn more about the Callawassie Island lifestyle , then contact Beth Ann Dickie to explore the possibilities at 3 Shellfish Lane.

3 Shellfish Lane, Okatie

Listing courtesy of EXP Realty LLC.

$799,000
4 Beds 4 Baths 2,841 SqFt. HILTONHEAD-453887 MLS
This Berkeley Hall home has been thoughtfully refreshed and is truly move-in ready, with furnishings removed, fresh interior paint, and a professional deep cleaning creating a light, bright, and welcoming atmosphere. Blending timeless Lowcountry architecture with an open, flowing floor plan, the home is designed for effortless everyday living and entertaining.A sun-filled foyer opens to the spacious great room, where custom built-ins and a gas fireplace create a warm focal point. The adjoining kitchen features granite countertops, stainless steel appliances, abundant workspace, and seamless access to the main living areas.Outdoor living is equally inviting with an expansive screened lanai offering a covered dining area, outdoor kitchen, and relaxing spa-perfect for entertaining or unwinding in privacy.The primary suite is a peaceful retreat with dual walk-in closets, a soaking tub, and direct access to the patio. A private office with a full bath and closet provides exceptional flexibility and can easily serve as a fourth bedroom. Two additional guest bedrooms share a well-appointed ensuite bath.Additional features include a spacious laundry room and a two-car garage with a dedicated golf cart bay.Ideal as either a full-time residence or a lock-and-leave getaway, this home offers a carefree lifestyle with landscaping and select exterior maintenance included in the POA fees. Enjoy all that Berkeley Hall has to offer from one of the community's most desirable neighborhoods.Some photographs have been virtually staged.

86 Hopsewee Drive, Okatie

Listing courtesy of Charter One Realty.

$3,095,000
4 Beds 5 Baths 4,505 SqFt. HILTONHEAD-447902 MLS
Situated on 3.19 acres of Lowcountry charm, this Charleston style home includes 4 bedrooms, 3 full baths and 2 half baths with 4,515 sq. ft. of an open floor plan. The home offers privacy and breath-taking views of the marsh and river with high ceilings, exquisite millwork and a renovated gourmet kitchen. The master suite, with an en-suite bathroom, feeds into a well-placed laundry room. A stunning spiral staircase leads to an office and three additional bedrooms and two full baths. The home includes a finished bonus room above the garage with extra storage. A screened porch overlooks a water feature and a native plant butterfly garden. A three-car garage and a separate shed provide enough space for gardening or simply storage. The property is also equipped with a whole home generator. HOA Amenities: Guard Gated, Palmer designed golf course, Tennis/Pickleball/ Croquet, Sports Complex, Two pools, Two Restaurants, Community boat docks, Equestrian facility, Sporting Clay Range, 30 miles of Hiking Trails and a fully staffed Nature Center.

224 Spring Island Drive, Okatie

Listing courtesy of Spring Island Realty LLC.

$625,000
4 Beds 3 Baths 2,720 SqFt. HILTONHEAD-446580 MLS
Accessible Lowcountry Living on beautiful Callawassie Island! Located on quiet, desirable Osprey Circle, this well-established home is surrounded by towering pines, palms and classic island charm. This quality constructed home, built by the Tilton Group, offers over 2,700 finished square feet, the flexible layout includes wide-plank flooring, attic foam insulation, crawlspace encapsulation, and remodeled kitchen (2019). New roof 8/2026! The living room with fireplace flows to the dining area, breakfast nook, and screened porch with tranquil lagoon views. Designed for easy, single-level living, the primary suite is privately situated opposite two guest bedrooms. A spacious bonus room with en-suite bath over the garage provides ideal flexspace for guests, office or den. Thoughtfully laid out and ready for personal touches, this home offers space, privacy, and opportunity in one of Callawassie's most sought-after locations. Enjoy renowned Island amenities including golf, tennis, pickleball, fitness center, docks, clubhouse dining, 24-hour gated security, and a vibrant social community, all conveniently located between Hilton Head, Bluffton and Beaufort.

63 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

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