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$2,100,000
1 Beds 2 Baths HILTONHEAD-503981 MLS
1 Straight Road is a meticulously designed 10 acre equestrian estate showcasing exceptional quality throughout. The property features four irrigated Bahia grass paddocks, each equipped with automatic waterers connected to city water. One paddock, conveniently located near the barn, includes a 60 foot round pen. At the heart of the property is an award winning four stall center isle barn with spacious living quarters above. The barn offers two full size 12x14 stalls on each side, all with direct access to outside turnout. The ground level includes equipment and carriage storage, a conditioned office, full bath, tack room, feed room, and a covered wash stall, providing both functionality and comfort. Upstairs, the 1,120 square foot apartment features a living room, dining area, bedroom, bathroom, and a generous screened porch, creating a private and inviting residence overlooking the grounds. Near the entrance to the property is a separate storage barn with two bays and covered horse trailer parking. Attached is a conditioned greenhouse, and nearby sits a well organized garden with fifteen raised beds, all enclosed by an eight foot fence for protection. A tour of 1 Straight Road makes it clear that no detail was overlooked. This is a thoughtfully planned equestrian complex where quality craftsmanship and careful design come together seamlessly.

1 Straight Road, Okatie

$689,900
3 Beds 4 Baths HILTONHEAD-503347 MLS
A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.

49 Winding Oak Drive, Okatie

$689,900
3 Beds 4 Baths 193784 MLS
A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.

49 Winding Oak Drive, Okatie

$3,479,000
4 Beds 5 Baths HILTONHEAD-503381 MLS
Currently under construction by award-winning May Residential Builders, this Palmetto Cove model showcases the builder's reputation for uncompromising quality, superior craftsmanship, and enduring durability. Built with top-of-the-line materials and engineered to withstand up to 180 mph hurricane-rated standards, this home delivers both peace of mind and timeless design. May Residential Builders is a recent Lighthouse Award winner, earning Best Exterior and Best Kitchen, along with Second Place for Interior Design - a testament to their elevated attention to detail. Spanning approximately 4,900 square feet, this thoughtfully designed residence offers four bedrooms, five baths, and an open, elegant floor plan ideal for both everyday living and refined entertaining. The home will be sold fully furnished and turnkey, allowing for a seamless move-in experience with completion anticipated by February 2027. Luxury features abound, including a Thermador appliance package, high-end finishes throughout, a private pool, outdoor fireplace, whole-house generator, and water softener system. Enjoy sweeping golf course views from your outdoor living spaces, creating a serene backdrop for Lowcountry living at its finest. The Berkeley Hall transfer fee is included, further enhancing the exceptional value of this offering. This is a rare opportunity to own a brand-new, custom-built, turnkey luxury home - without the stress or delays of building - in one of the most desirable communities in the Southeast. Located within the prestigious, private gates of Berkeley Hall, this exceptional new construction residence represents the pinnacle of Lowcountry luxury living. Renowned for its world-class amenities, championship golf, and unparalleled lifestyle, Berkeley Hall is widely regarded as one of the most exclusive communities in the region - and this home is a flawless complement to its setting. Seller is offer $125,000 towards community enhancement fee.

44 Lancaster Boulevard, Okatie

$6,500,000
5 Beds 9 Baths 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

$1,100,000
2 Beds 3 Baths 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

$395,000
4 Beds 3 Baths 193412 MLS
New quartz kitchen countertops Just installed! Welcome to this immaculate 4-bedroom, 2.5-bath home in desirable University Place, built in 2021 and thoughtfully maintained for easy, move-in-ready living. Freshly painted interiors, durable LVP flooring, and a bright kitchen featuring stainless-steel appliances and a gas range/oven create a clean, modern feel throughout. The spacious kitchen also offers an oversized pantry, while an additional storage closet provides even more room to keep everything organized. All four bedrooms are generously sized, offering flexibility for family, guests, a home office, or hobbies. Plus a Loft for extra living space. Outside, enjoy a partially fenced backyard and the convenience of a 2-car garage. The location is a standout: close to the USCB Bluffton campus, shopping, dining, and medical facilities, with easy access to Savannah and Beaufort. And when it's time to relax, the beautiful beaches of Hilton Head Island are only about 20 minutes away. Whether you're looking for a comfortable primary residence, a second home, or an investment opportunity, this property offers modern features, convenient access, and excellent Lowcountry lifestyle appeal. Come see why 111 Auditorium Rd could be the perfect place to call home!

111 Auditorium Road, Okatie

$1,395,000
4 Beds 4 Baths 192706 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

$1,395,000
4 Beds 4 Baths 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

$1,390,000
5 Beds 6 Baths 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

$1,390,000
5 Beds 6 Baths 192640 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 Dues 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

$799,000
4 Beds 4 Baths 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

$3,095,000
4 Beds 5 Baths 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

$625,000
4 Beds 3 Baths 186591 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). 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 f d 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

$625,000
4 Beds 3 Baths 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

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