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$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.

$2,250,000
4 Beds 5 Baths 4,717 SqFt. HILTONHEAD-502394 MLS
A Refined 13+ Acre Lowcountry Equestrian Retreat on Spring Island - A long, oak-lined drive leads to this extraordinary 13.2-acre equestrian estate - an intimate compound within the private, gated community of Spring Island. The property features a main house, guest cottage, 2+ car garage with golf cart bay and potting shed, the Orvis retreat, an equestrian viewing gazebo, three-stall barn, and two large, fenced pastures plus one paddock around the stalls. The main residence offers a welcoming front porch with sweeping views of pastures and the barn. French doors open to a vaulted great room filled with natural light and fine craftsmanship. The chef's kitchen with dual islands and premium appliances flows into a keeping room anchored by a Savannah brick fireplace. A screened porch opens to gardens for year-round Lowcountry living. The primary suite includes a sitting area, spa-style bath, and private porch. Guest suite, laundry, and bright studio or "woman cave" complete the main living areas. A breezeway connects the main house to the garage and potting shed, ideal for gardeners and nature enthusiasts. The guest cottage offers front and back porches, a sitting area with kitchenette, and two ensuite bedrooms, providing privacy and comfort for family or friends. Across a wooden bridge, the Orvis Room "man cave" features a wraparound porch with outdoor fireplace overlooking a tranquil water feature. Inside, a great room, office, or bourbon room, and full bath create an ideal gathering place. The gazebo overlooks pastures, perfect for entertaining or watching dressage. The three-stall barn includes a tack room, bath, utility area, and space for future living quarters. Two large, fenced pastures and one paddock provide ample room for horses. Life on Spring Island is unlike anywhere else, offering 3,000 acres of preserved natural beauty and premier amenities: Arnold Palmer-designed golf, equestrian center, tennis and pickleball, fitness complex with heated and chilled saltwater pools, scenic trails for walking or riding, a 7.5-acre community garden, and an inspiring art barn. (Note - 5 photos with furniture in them have been virtually staged to show the home's potential)

21 Straight Road, Okatie

Listing courtesy of Charter One Realty. Selling Office: Spring Island Realty LLC.

$732,000
3 Beds 3 Baths 3,115 SqFt. HILTONHEAD-501953 MLS
Nestled at the end of a quiet cul-de-sac in Sun City North, this 3 bedroom, 3 bath Martin Ray with loft offers serene water views in a tranquil setting. The gourmet kitchen is custom-designed for both function and elegance, with a five-burner gas range, granite countertops, under-cabinet lighting, spacious pantry, and oversized island. Inside, you'll find warm wood flooring, a gas fireplace, a Carolina room, a den with French doors, laundry room w/extra cabinets, countertop & sink, and a primary suite that includes a tray ceiling and custom walk in closet. The second floor includes a versatile loft, storage closet & a guest suite/bathroom making it ideal for overnight visitors. The extended garage includes a dedicated golf cart bay and walk-up attic storage. The outdoors impresses with a covered front porch, a four-seasons room with tile flooring, and an extended paver patio overlooking the lagoon perfect for entertaining or quiet relaxation.

906 Knollwood Court, Okatie

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Howard Hanna Allen Tate Lowcountry.

$680,000
3 Beds 3 Baths 2,522 SqFt. HILTONHEAD-501854 MLS
Welcome to 188 Valleybrooke Ct S. - your new home in amenity-rich Sun City. As soon as you enter this striking 3/3 residence, you will know that you have found your Lowcountry oasis. Sought-after Castle Rock plan, you will appreciate the trend-setting upgrades and finishes the owners have put in when building the home. The main level is open and is a perfect floor plan designed for entertaining. The front office works well for a remote workspace, and the kitchen is a gathering spot for family and friends. Designer touches will delight chefs of all levels, from the oversized island to the gas cooktop. In the light-filled great room, the sellers have added a wonderful entertainment area complete with extra storage and plantation shutters throughout. When it is time to relax, you won't find a better spot than the tranquil sunroom. Shiplap walls and captivating views to the vast lagoon will bring a nice end to a long day. The primary suite on the main level has a tray ceiling and a spa-like bathroom w/ an enormous walk-in closet, updated shower, and fixtures. The upper floor is a perfect getaway for guests. A full bed and bath, as well as a living area and flex room ( flex room could be a playroom, nursery, or craft room). You can't beat enjoying your morning coffee on the front porch- total privacy to the front and side along with watching all the nature our lagoons bring. This home has been meticulously cared for and is ready for you to begin your new life.

188 Valleybrooke S Court, Okatie

Listing courtesy of Charter One Realty. Selling Office: EXP Realty LLC.

$2,800,000
4 Beds 5 Baths 3,435 SqFt. HILTONHEAD-500613 MLS
Where contemporary elegance meets timeless Lowcountry beauty. This 4-bedroom, 4 1/2-bath, 3,435-sq-ft Spring Island masterpiece is a seamless fusion of modern design and the soulful charm of the Lowcountry, perfectly positioned among centuries-old Live Oaks. Built in 2021, this home was honored with the coveted Lighthouse Award in all four categories - Best Kitchen, Best Bathroom, Best Exterior, and Best Overall - a true testament to its exceptional craftsmanship and design. Inside, light pours into open, inviting spaces. The chef's kitchen with premium appliances and an entertainer's layout flows into a great room anchored by a striking tabby fireplace. Walls of windows invite the outdoors in, while an expansive, heated screened porch, complete with outdoor grill, kitchen pass-through, and TV, creates the ultimate gathering space for any season. The first-floor primary suite is a serene retreat, featuring a spa-inspired bath with the rare luxury of both indoor and outdoor showers. Upstairs, each guest suite enjoys its own private bath, offering comfort and privacy. An elevator connects every level, ensuring effortless living. The grounds are a work of art - front and rear water gardens shimmer in the sunlight, while a tranquil backyard water feature sets the stage for evenings around the fire pit under a canopy of stars. Conveniently located to both the River House and Golf House, you'll enjoy Spring Island's unmatched amenities with over 3,000 acres of preserved beauty, an Arnold Palmer golf course, equestrian facilities, tennis and pickleball, deep-water docks, and miles of scenic trails. More than a home, this is an experience - crafted for those who value beauty, nature, and the art of living well.

303 Spring Island Drive, Okatie

Listing courtesy of Charter One Realty. Selling Office: The Homesfinder Realty Group.

$688,000
3 Beds 3 Baths 2,723 SqFt. HILTONHEAD-500980 MLS
Enjoy stunning water-to-golf course views in this elegant 3 Bedroom, 2.5 Bathroom Cumberland Hall home, set in the highly desirable Herons Point neighborhood of Sun City. The gourmet kitchen is outfitted with a gas range, stainless steel appliances, granite countertops, under-cabinet lighting, ample cabinetry, and a generous island. The outdoor living space is designed for entertaining includes a covered front porch, custom four-seasons room, and pavered back patio. Additional upgrades include wood floors, a large primary suite, den w/French doors, an oversized garage with dedicated golf cart parking and professionally landscaped grounds. Living in Sun City Hilton Head offers a true resort-style experience with access to golf courses, indoor and outdoor pools, fitness centers, walking trails, a wide variety of clubs, and a lively social calendar. Conveniently located near shopping, dining, medical facilities, and just a short drive to the beaches of Hilton Head Island, this move-in-ready home with incredible ever changing sunset views is a must see!

416 Freshwater Lane, Okatie

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Keller Williams Realty.

$420,000
3 Beds 2 Baths 1,714 SqFt. HILTONHEAD-501098 MLS
Come home to this charming 3 bdrm, 2 bath home in the popular Cypress Ridge Reserve near the community pool complex. This home features a spacious GR w/oversized quartz kitchen bar, 42" soft close white cabinets, new pendant lights, SS appliances to include new upgraded refrigerator, LVT flooring in living area and abundant light. Comfortably accommodates guests w/2 bedrooms in front and MBR suite with walk in closet is in back overlooking the spacious, wooded backyard. Home has been infrequently used as a 2nd home since built in 2020 and in "like new" condition. The Reserve section of Cypress Ridge offers stress free living. HOA fee covers landscaping, twice annual house washing, and pest control. Relax in the cozy screened in porch and enjoy the tranquility it brings. Fence can be installed. Ready for immediate occupancy.

506 Rye Creek Circle, Okatie

Listing courtesy of Howard Hanna Allen Tate Hilton Head. Selling Office: Greco Group Brokered by eXp Realty.

$505,000
3 Beds 3 Baths 2,258 SqFt. HILTONHEAD-500618 MLS
This 3 bedroom (+ flex room) 2.5 bathroom model home is a showstopper-it is truly one of kind and checks all the boxes! You can't beat the view, the layout or location. With brand new glass on several windows (2025), a new roof with transferable warranty (2023), hot water tank (2021), HVAC (2018) and other big ticket item improvements you can have peace of mind! The open concept floor plan flows seamlessly from the foyer, optional formal dining area into the living room with vaulted ceiling and generous kitchen space. Spacious 2 car garage with floored attic and a massive work bench that enters the residence through mud room/ laundry room with storage and large utility sink. The Hawthorn model home in a former life means it comes with all the options/extra bells and whistles! An additional bay window flex room with lovely glass French doors, wood burning fireplace, bump out kitchen and illuminating sunroom. The sunroom gives a panoramic view of the garden, zoysia sod and glistening lake waters. Step out onto impressively large front porch and enjoy the swing and outdoors without leaving the property! This section of Cypress Ridge has no through traffic because it consists of only one street. Great investment potential or primary residence in a highly coveted part of town! Don't miss out on this rare opportunity to live in The Overlook at Cypress Ridge as well as enjoy their resort style amenities!

204 Argo Circle, Okatie

Listing courtesy of Keller Williams Realty. Selling Office: RE/MAX Island Realty.

$575,000
2 Beds 2 Baths 1,961 SqFt. HILTONHEAD-500597 MLS
Immaculate Martin Ray Model with Lagoon View. Beautifully updated and meticulously maintained, this 2-bedroom plus den, 2-bath offers elegant living in the desirable Sun City North community. The open-concept design features a gourmet kitchen with modern finishes, a spacious great room, and a separate den ideal for an office or guest space. Enjoy tranquil lagoon views from the screened porch, perfect for relaxing or entertaining. - Wood floors throughout, upgraded 5-inch base & crown molding (the builder only included 2-inch) - Upgraded KitchenAid appliances, including the dishwasher, oven, and range. - Custom shutters in the front room and over the kitchen window- French doors were an add-on off the front room/office into the entryway - The garage includes a storage staircase, space for two cars plus a golf cart, and a small hanging-clothes unit. - The living room curtains were custom-made, and both bedrooms have high-quality custom shades. All gutters were added as upgrades. Additional highlights include updated flooring, designer touches throughout, and excellent bedroom separation for privacy. Move-in ready and located near all of Sun City's exceptional amenities. This home combines style, comfort, and convenience.

1250 Northlake Boulevard, Okatie

Listing courtesy of RE/MAX Island Realty. Selling Office: Keller Williams Realty.

$365,000
3 Beds 2 Baths 1,482 SqFt. HILTONHEAD-500594 MLS
Thinking about buying new construction? Before you grab that shiny brochure, just remember: you'll also be buying your own window sills (yes... window sills), a vent so your hamburger grease actually leaves the house, ceiling fans, a refrigerator that isn't from the appliance graveyard (plus the extended warranty), washer, dryer, upgraded dishwasher, under-cabinet lighting, trim upgrades, and-if you're really lucky-PAYING EXTRA for a corner lot. Surprise! OR... you could buy this home, where all of those things are already done, installed, upgraded, and gorgeous and the home looks like a model. Your wallet can finally unclench. In addition, you'll find craftsman baseboards and windowsills, cottage-style trim, beadboard accents, wainscoting, and statement lighting throughout. The kitchen is a focal point, exuding luxury with quartz countertops, 42" cabinets, under-cabinet lighting, custom backsplash, and premium hardware. Wake up to serene sunrise views over the lagoon from your front porch, then stroll the neighborhood's sidewalks winding past peaceful lagoons and majestic Live Oaks. River Oaks sits quietly at the end of a street that meets the scenic Okatie River, offering Beaufort County living with access to Bluffton Schools. Here, small neighborhood charm meets the best of Lowcountry convenience.

74 Whispering Oaks Circle, Okatie

Listing courtesy of Dunes Real Estate. Selling Office: REsides, Inc..

$1,266,000
3 Beds 4 Baths 4,031 SqFt. HILTONHEAD-500350 MLS
Situated on a beautiful lot with a peaceful golf/pond view, this classic Lowcountry style custom home built by Steve Tilton (Coastal Signature Homes) features soaring 12 ft. ceilings throughout the entire first floor, elaborate molding trim package, granite kitchen counters, kitchen island with prep sink, oversized walk in pantry, Pella windows, Baldwin hardware, and incredible storage throughout. Enjoy outdoor living at its finest, with covered porches at the front and rear of the home, a gorgeous screened porch w/gas fireplace, and a new paver patio. A large 2 car garage with golf cart bay and unfinished space above for future use completes this attractive residence. Impeccably maintained, recent upgrades include new roof, new HVAC units, freshly painted exterior and mahogany exterior doors. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, Bocce courts, Dog park, 27 hole Golf course & 24/7 gated​​‌​​​​‌​‌​​​​‌‌​​‌‌​‌‌​​‌​​​‌​‌ security.

18 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Compass Carolinas, LLC.

$890,000
3 Beds 4 Baths 3,469 SqFt. HILTONHEAD-500165 MLS
Enjoy stunning golf course views from this 3BD/3.5BA Sonoma Cove with loft model nestled on a private homesite offering exceptional outdoor living. The home features two inviting living areas; a great room & a hearth room with a cozy fireplace, wet bar, wine rack and wine refrigerator. The gourmet kitchen is a chefs dream complete with a five-burner gas range, abundant cabinetry, granite countertops, raised dishwasher, large island & a spacious pantry. The second floor provides a private retreat perfect for guests featuring a bedroom, full bathroom & an additional living space. The primary bedroom/bathroom features a tray ceiling, raised double vanity with framed mirrors, large walk-in closet & a shower with an adjustable shower head, bench seat & frameless shower door. The fabulous outdoor living space includes a four seasons room w/mini-split & tile flooring, a covered patio w/tile flooring and a covered front porch. The extended garage includes golf cart parking, epoxy floors, utility sink and walk up attic storage. New roof 2023! Too many upgrades to list, this home is a must see!

461 Fernleaf Lane, Okatie

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: Keller Williams Realty.

$700,000
3 Beds 4 Baths 2,878 SqFt. HILTONHEAD-454883 MLS
Beautiful Morningside Lane model in Sun Citys 55+ resort-style community. Tiled walkway and front porch. Stained glass entry door. 3BR/3.5BA plus den/office. Crown molding throughout living spaces. Each bedroom has an en-suite bath. Wood floors in common areas, carpet in bedrooms. Gourmet kitchen with granite counters, breakfast bar, large island with pendant lights for food preperation, backsplash and accent-lit cabinetry. Formal dining room and dry bar. Fireplace and built-ins in family room. Updated primary suite with walk-in shower. Carolina Room adds additional living space and natural lighting from the large windows. Door from Carolina Room leads to exteded lanai with built-in grill and connects to the paver patio overlooking wooded, private backdrop. Extended garage with room for cars and golf cart. Pull down stairs in garage lead to storage space over the garage. Full-size laundry with generous cabinetry, sink and counter space. Located for easy access to all of Sun City Hilton Head's oustanding amenities.

405 Rivergrass Lane, Okatie

Listing courtesy of Howard Hanna Allen Tate Lowcountry. Selling Office: The Cox Team Brokered by EXP.

$515,000
3 Beds 2 Baths 2,174 SqFt. HILTONHEAD-455063 MLS
Popular Delaware Model – Golf & Nature Views! This spacious 2,174 sq ft one-level home features 3 bedrooms, 2 full baths, an expansive living room with built-in bookshelves and an electric fireplace, plus a Carolina Room and screened porch—perfect for indoor/outdoor living. The oversized 2-car garage includes an additional 4 feet for storage or workshop space. Ideally positioned on a quiet horseshoe road with park like views and golf course views in front and a private wooded backdrop, offering a serene setting. Community highlights include a clubhouse, pavilion, pool, tennis, pickleball, bocce, fitness center, and a scenic 7.5-acre lake with a ¾-mile walking path. Golf cart friendly and not age-restricted—all are welcome!

11 Eagle Pointe Circle, Okatie

Listing courtesy of EXP Realty LLC. Selling Office: Keller Williams Realty.

$465,000
3 Beds 2 Baths 1,598 SqFt. HILTONHEAD-500052 MLS
Discover the perfect blend of privacy, charm, and convenience in this beautifully maintained 3 bed, 2 bath home nestled on a lush, tropical-third of an acre lot. Located in the desirable and quiet community of Chechessee Bluff, this Lowcountry gem offers gorgeous curb appeal with a welcoming covered front porch and fresh exterior paint. Step inside to enjoy easy one-level living with a vaulted-ceiling living room featuring a cozy fireplace and an open, airy feel. The kitchen is a standout with modern white cabinetry, granite countertops, stainless steel appliances, and stylish finishes. The split floor plan ensures privacy, with the spacious owners suite tucked away from the secondary bedrooms.Need flexible space? The Flex room includes a Murphy bed, perfect for guests or a home office. Step out back into your screened lanai ideal spot for morning coffee or evening relaxation, overlooking the serene, fully fenced backyard with a firepit and tropical landscaping. Additional highlights include: Brand NEW 2025 Roof, NO Carpets, Upgraded lighting fixtures, Beautiful wainscoting and detailed craftsmanship throughout, Driveway basketball court for added fun! This move-in ready home offers timeless Southern charm with modern comfort style without the restrictions of an HOA. Come see why this hidden gem is the perfect place to call your Lowcountry home! Steps from Callawassie Island! Easy commute to Beaufort, Old Town Bluffton, and Hilton Head Island beaches!

34 Chechessee Bluff Circle, Okatie

Listing courtesy of Keller Williams Realty. Selling Office: Charter One Realty.

$383,000
4 Beds 3 Baths 1,750 SqFt. HILTONHEAD-454898 MLS
CHARMING LAGOON-VIEW, OPEN FLOOR-PLAN HOME! Pristine condition. Remodeled in 2024 with quartz countertops, S/S kitchen appliances, roof, the list goes on & on. Spacious master on main level with updated en suite bath, 3 additional bedrooms upstairs with updated bath & huge walk-in floored attic. Great room with fireplace & plenty of natural light. Private screened porch overlooks large backyard & forest preserve. And from inviting front porch enjoy the lagoon view w/ fountain & gazebo. Oversized 2 car garage—room for workshop, toys, cars, etc. Community pool one-block away. Shopping & restaurants close by. So many reasons to love living here!

121 Southside Parkway, Okatie

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Daniel Ravenel Sotheby's International Realty.

$830,000
4 Beds 4 Baths 3,188 SqFt. HILTONHEAD-453956 MLS
This coastal-chic golf cottage is one of the most requested rental cottages located in the private, gated golf community of Berkeley Hall! With well over $50,000 in rental bookings from May '25 to August '26, this well-appointed cottage is conveniently located within close proximity to the Clubhouse, has its own driveway and offers private wooded and marsh views. The cottage lives "like a home" and was tastefully updated over the last three years, including but not limited to a newer kitchen with an island, newer appliances, quartz countertops, updated cabinets and a porcelain sink; white oak flooring added to two of the first floor "lockouts"; built-ins/floating shelving with a beverage refrigerator installed around the fireplace in the living room; interior painting; and updated lighting throughout. In addition, the roof was replaced in 2023, two of the four HVAC systems were replaced in the last three years and new hot water heaters were installed in 2024. The home has two "lockout" units with a living room and kitchen on the first floor, plus a loft and two oversized ensuites on the second floor. This unique layout configuration allows for multiple rental options. But if renting isn't for you, enjoy this cozy cottage as your full-time or part-time residence! It's entirely up to you as there is no obligation to be part of the rental program. Expansive front porch and back patio provide outdoor space to relax after a busy day of golf, pickleball, tennis, etc.

113 Good Hope Road, Okatie

Listing courtesy of Engel & Volkers. Selling Office: Charter One Realty.

$615,000
3 Beds 2 Baths 2,093 SqFt. HILTONHEAD-454100 MLS
Enjoy captivating water-to-golf views from this stunning 3BR/2BA Martin Ray home in the coveted Mariners Cove neighborhood. The chef’s kitchen is designed for style & function, featuring a 5-burner gas range, expansive island, granite counters, roll-out shelving, a roomy pantry & soft-close cabinetry. Upgrades: tray ceiling in PB, butler’s pantry, wood floors, screened lanai & covered front porch. Storage is exceptional w/vast walk-in closet in the PB, an oversized storage closet & convenient walk-up stairs to attic storage. Settle into the relaxed elegance and sweeping water & golf views of this exquisite Sun City home—truly a must-see!

509 Nautical Lane, Okatie

Listing courtesy of Weichert Realtors Coastal Properties. Selling Office: Weichert Realtors Coastal Properties.

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