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$900,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-507539 MLS
Set against a breathtaking Lowcountry backdrop, this stately custom home offers timeless character, generous living spaces, and an extraordinary setting that captures the very essence of coastal living. Perfectly positioned on a homesite with a deep, wide western exposure, the sweeping marsh views stretch endlessly to the Colleton River, delivering unforgettable sunsets that paint the sky each evening. Spanning approximately 3,925 square feet, this classic residence features 4 bedrooms and 3.5 baths, thoughtfully designed for both comfort and functionality. Expansive living room and gorgeous foyer define this home and are anchored by the beauty of moss-draped live oaks and marsh views. For a more informal, relaxed living space, the large family room, complete with an office nook and bar sink, ideal for entertaining or relaxed everyday living, is only a few steps away from the kitchen area. The second-floor loft offers an oversized retreat for the additional 2 guest bedrooms overlooking the marsh, creating a serene vantage point for soaking in the natural beauty that surrounds you. The home's inviting outdoor spaces are equally impressive. A full front porch welcomes you with classic Southern charm, while the rear deck flows seamlessly into a screened gazebo-perfect for al fresco dining, quiet afternoons, or simply enjoying the coastal breeze. Beneath the elevated back porch, ample storage provides practical convenience. Inside, elegant details abound. Custom built-ins enhance the living room, while the dining area features beautifully crafted cabinetry. Hardwood floors run throughout the main living areas, complemented by comfortable carpeting in the bedrooms. The primary suite offers a private retreat with dual vanities, spacious closets, a jetted tub, and a separate shower. An additional guest bedroom on the main level provides flexibility for visitors. Surrounded by mature landscaping and framed by majestic live oaks, the property exudes natural beauty and privacy. With its rare combination of location, views, and classic Lowcountry design, this home presents an exceptional opportunity to create your own coastal sanctuary.

4 Bent Tree Lane, Okatie

Listing courtesy of Charter One Realty.

$1,099,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-503887 MLS
When you cross over the causeway into Callawassie Island, you are transported into a peaceful private world where moss-draped oaks, winding marsh views, and quiet coastal beauty instantly replace the pace of everyday life, creating a true sense of retreat the moment you arrive. Driving past beautifully manicured golf fairways woven seamlessly with natural wildlife habitat and serene lagoons, every turn offers a blend of refined landscape and untouched Lowcountry beauty. The charm continues right into this new construction home, where thoughtful design and setting feature 3 bedrooms in the main house and an in-law suite above the garage. It's perfect for guests, extended family, or flexible living arrangements that adapt easily to your lifestyle. Welcome home to 26 Longwood.

26 Longwood Drive, Okatie

Listing courtesy of Moul, REALTORS®.

$824,900
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-507264 MLS
Tucked away on Oyster Cay, this private .82-acre homesite offers pool, space, and location. Positioned on a corner wooded lot, the property presents a unique opportunity just a brief stroll to the River Club amenities and deep-water docks, while tucked along a quiet, private street.The property features a large pool and hot tub surrounded by an expansive pool patio and a rare fenced area, offering a valuable benefit to new buyers given current fencing restrictions. The setting provides both privacy and functionality, with ample space to enjoy outdoor living. A new roof (2022) and new windows (2023) further enhance the home.This home offers buyers the opportunity to come in at an attractive price point and make it their own, whether through updates over time or a more immediate vision.The lifestyle on Callawassie Island is hard to beat, offering a private golf experience with 27 holes, four deep-water docks, and a true sense of privacy behind the gates. Private island living here is something you truly have to experience firsthand.

2 Shellfish Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,399,999
4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-506875 MLS
Looking for timeless luxury in a quiet, serene neighborhood that offers world-class amenities within a gated and secure island community? Then you must see and make this meticulously designed custom home built by Sunset-Life Properties your new sanctuary! Located on the green of Tom Fazio's Magnolia #4 golf hole, par 4, this home has far more elegant features than can be listed here. No expense was spared to have the finer things in life! GE Monogram appliances including 42" side by side refrigerator, 36" gas range with 6 burners and pot filler in backsplash above, Double Oven in addition to oven in range, 24" Dishwasher, Microwave, and 2 sets of Double Drawer Refrigerators both in the Kitchen and Bonus Bar above on the Second Floor. Both areas also have Scotsman 30 lb Gourmet Ice Makers, and the home is even furnished with Electrolux stacked front loading 4.5 cft Washer and 8 cft Dryer. The cabinets are 3/4" plywood Wood-Mode and Brookhaven luxury brands with walnut interior, dovetail construction, and soft close. An Isokern propane fireplace is in the Family Room and 3CM custom granite countertops are installed throughout the home. PLAY Custom Home Technology is installed in this home with predefined engraved labeled switches making it easy to push the right one. This home even features areas prepped for an outdoor kitchen on a separate Grill Porch and a bar area on the Screened Porch. Spray foam insulation thoughout this home with 3 zones for AC and jamb switches for closet lights. This home is a MUST SEE along with the Callawassie Island Community!!!

54 Osprey Circle, Okatie

Listing courtesy of Realty One Group - Lowcountry.

$1,850,000
4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-506851 MLS
Tucked away on nearly three wooded acres, this gracious Southern estate offers timeless charm, exceptional privacy, and inviting spaces designed for relaxed Lowcountry living made even more desirable by the rare combination of a generous homesite and low HOA fees. The expansive acreage provides a sense of seclusion and freedom seldom found, allowing room to breathe, enjoy nature, and live without the constraints of tightly spaced neighborhoods. From the moment you arrive, the expansive front porch sets the tone, perfect for rocking chairs and morning coffee. Inside the main home, beautiful oak floors flow throughout warm, traditionally styled interiors that feel both comfortable and refined. The kitchen is the heart of the home, featuring a large central island ideal for gathering, meal prep, and entertaining, along with a double oven and gas range-perfect for the home chef. Thoughtful details and abundant natural light enhance every room, resulting in a home that is welcoming, well-balanced, and timeless in character. The home's porches truly steal the show. In addition to the generous front porch, the large screened back porch overlooks the peaceful, wooded setting, an ideal spot for outdoor dining, evening breezes, or simply enjoying the quiet surroundings year-round, with the privacy that only a larger lot can provide. The main residence offers three large bedrooms, a den/office, a formal dining room, family room, large pantry, and laundry room. The detached three-car garage includes private living quarters complete with a full kitchen, dining and sitting area, and an additional bedroom-ideal for guests, extended family, or a personal retreat. The adjacent workshop adds excellent functionality for hobbies, storage, projects, or a cart garage. Outdoors, the estate property continues to impress with Live Oaks, mature trees, a shed, and abundant space to garden, expand outdoor living, or simply enjoy the natural setting. A pool plan has already been approved by the ARB, further enhancing the flexibility of the expansive lot. This is a rare opportunity to own a classic Southern home that blends comfort, character, and space in a serene Lowcountry setting.

66 Heyward Point Road, Okatie

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$1,899,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-505898 MLS
Experience the pinnacle of Lowcountry luxury living in Berkeley Hall with this brand-new, under-construction residence by renowned builder, AR Homes with completion slated for October 2026. The sought-after St. George model offers an exceptional single-story design featuring 3 bedrooms, a spacious bonus room, den/office and a 3-car garage, thoughtfully crafted for both everyday living and elevated entertaining. Designed with a refined, modern aesthetic, the home showcases wide-plank white oak flooring, curated designer finishes, and a seamless open-concept layout. The chef's kitchen is anchored by GE Monogram appliances, custom cabinetry with soft-close features, and premium Cambria quartz countertops, creating a space that is both functional and visually striking . Elevated details continue throughout with matte black and champagne bronze hardware, designer tile selections, and layered textures that bring a sophisticated, organic warmth to the interiors. The primary suite is envisioned as a private retreat, complete with a spa-inspired bath featuring luxury tile work, frameless glass shower, and upscale fixtures. Secondary bedrooms offer comfort and privacy for guests, while the bonus room provides flexibility for a media lounge, office, or additional guest suite. Outdoor living is at the forefront, with a spacious 510 SF lanai designed for year-round enjoyment, including a gas fireplace, built-in outdoor kitchen, grill, and vent hood, ideal for entertaining in true Lowcountry style . Thoughtful enhancements such as a tankless water heater, smart home features, energy-efficient construction, and impact-resistant windows ensure modern convenience meets timeless design. Room for an outdoor pool. Located within the gates of Berkeley Hall, residents enjoy access to world-class amenities including two Tom Fazio golf courses, a state-of-the-art learning center, river park, and an unmatched private club lifestyle. Note: Pictures of a similar model.

2 Woodside Circle, Okatie

Listing courtesy of The Agency Hilton Head.

$1,025,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-505127 MLS
Classic Lowcountry charm meets privacy and sweeping golf views in this beautifully maintained home set on over one acre on Callawassie Island. Positioned more than 300 feet from the road along a tree-lined, landscaped drive, the home offers exceptional curb appeal and a peaceful setting overlooking the recently renovated Dogwood golf course. The thoughtfully designed floor plan features 4 bedrooms and 3.5 baths, including a spacious first-floor primary suite and a dedicated office. Upstairs guest bedrooms and a versatile bonus room provide comfortable space for family or visitors. Hardwood floors, custom built-ins, detailed millwork, and numerous walk-in closets enhance the home's character and functionality. Floor-to-ceiling windows along the rear of the home fill the living spaces with natural light and showcase the beautiful golf course views, while the screened porch offers the perfect place to relax and enjoy the professionally landscaped yard. A wonderful opportunity to enjoy classic Lowcountry living in the sought-after community of Callawassie Island.

50 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$3,800,000
5 Beds ⋅ 7 Baths ⋅ HILTONHEAD-505471 MLS
Designed to blend contemporary architecture with classic Lowcountry elements, this remarkable compound was envisioned by architect Chris Schmitt as a collection of five distinct structures including the main residence, guest house, workshop, studio, and a three bay garage. The guest house was completed in 1998, with the remaining buildings added over time, culminating in the completion of the main residence in 2004.The AIA award winning main residence is extraordinary not only for its innovative design but also for the exceptional quality of materials and craftsmanship throughout. Perfectly proportioned details, balance, and scale create a home of striking visual appeal, enhanced by exposed beams, vaulted ceilings, and antique heart pine flooring milled in Savannah in the 19th century. A custom wall mural by artist Jordi Pedrola further distinguishes the interior. At the heart of the home, the great room features soaring ceilings, exposed trusses, and tall windows that flood the space with natural light. The gourmet kitchen flows seamlessly into the dining room and sunroom, all of which overlook Rice Gate Pond and open easily to the home's extensive outdoor living spaces including a screened porch and approximately 1,000 square feet of outdoor living area designed for relaxing and entertaining. The spacious ground floor primary suite offers a private retreat with direct access to an outdoor spa and shower. The luxurious primary bath features a steam shower. Two beautifully appointed bedrooms are located on the second floor. The guest house echoes the distinctive inverted roofline of the main home's sunroom, with a dramatic living room featuring floor to ceiling glass and peaceful views of the surrounding forest. Complete with a small kitchen, dining area, and two bedrooms with baths, it offers visitors both comfort and privacy. Raised walkways connect the buildings and enhance the sense of a thoughtfully designed compound. Additional structures include a versatile entertainment building with a chef kitchen and a large garage door that opens for indoor outdoor gatherings, as well as a separate studio with its own bathroom ideal for creative work or a private office. The property also includes a wine cellar, custom lighting system throughout, and a spacious three car garage. The landscape plan was created by highly regarded landscape architect Thomas Angell, who artfully blends formal landscaping with the natural beauty of Spring Island.

9 Rice Gate Circle, Okatie

Listing courtesy of Spring Island Realty LLC.

$1,890,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-504585 MLS
Enjoy exceptional waterfront living on Callawassie Island with rare western exposure and unforgettable sunset views over the tidal marshes of Chechessee Creek, complemented by peaceful water and golf views from the front of the home. Privately positioned, this pristine custom-built residence offers a true Lowcountry lifestyle with a private short dock, floating dock, and new boat lift providing direct water access for boating, kayaking, and sunset cruises. Designed for both everyday comfort and effortless entertaining, the open floor plan is centered around a chef's kitchen featuring Wolf and Sub-Zero appliances, a 10-foot island, beverage bar, wine cooler, and ice maker. Wide plank hardwood floors flow throughout the main living areas, while two first-floor guest suites offer beautifully remodeled en suite baths for privacy and convenience. Thoughtful improvements enhance both form and function, including a newer roof, new deck and shutters, a custom-built fireplace with new insert, replaced interior doors, all new water piping, spray foam insulation in the crawl space, new crawl space screening, updated lighting, refreshed landscaping, and a full exterior repaint in 2025.Expansive outdoor living spaces capture sweeping marsh views and glowing sunsets, creating a serene and private backdrop that changes with the tides and seasons. 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.

41 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$331,000
3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-505169 MLS
Step out of your DeLorean and back to 1987 at 49 Heron Walk on Callawassie Island. Perfectly positioned on the tee box of the first hole of the Dogwood Course, this classic golf cottage delivers a true front-row seat to opening drives and glowing morning sunrises over the fairway. Lovingly maintained in remarkable original condition (with updated mechanicals), the home features warm woodwork, comfortable living spaces, and authentic 80s character throughout. Enjoy it just as it is, or modernize to your taste-either way, you're starting with an unbeatable golf course setting and timeless island appeal. Live here full time or create income as a sought-after retreat for visiting golfers-no flux capacitor required. Great Scott, this is island living with timeless style. Optional Golf.

49 Heron Walk, Okatie

Listing courtesy of Moul, REALTORS®.

$1,399,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-505052 MLS
Lowcountry waterfront living on Callawassie Island in Okatie, SC. Built by award-winning builder Steve Tilton, 47 Sugar Mill is tucked away at the end of a quiet cul-de-sac and surrounded by ancient live oaks draped in Spanish moss for a truly private, coastal setting, and boasts a brand new roof in June 2026. This 4BR + office home is designed for relaxed island living with oversized front, back, and screened porches-perfect for morning coffee, afternoon breezes, and evening gatherings. Inside, soaring cathedral ceilings, a welcoming fireplace, and abundant natural light create an inviting main living space that seamlessly connects to the outdoors. The rare showstopper is the backyard on a tidal creek with a floating dock and boatlift-opening the door to a lifestyle of kayaking, paddleboarding, boating, fishing, and crabbing right from home. A 2.5-car garage includes a dedicated golf cart bay for easy island exploring. If you've been searching for a Callawassie Island waterfront home with a dock and lift, 47 Sugar Mill is a standout opportunity.

47 Sugar Mill Drive, Okatie

Listing courtesy of Charter One Realty.

$725,000
3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-504968 MLS
Experience the romance of Lowcountry living on Callawassie Island. Tucked beneath towering pines on a quiet, private homesite, this 2,580 sq ft home offers 3BR/3BA plus a dedicated office and captivating lagoon-to-golf views. A classic brick stairway leads to an expansive, columned front porch-rocking-chair ready and cooled by ceiling fans-setting the tone for slow mornings, sweet tea afternoons, and sunset conversations. Inside, enjoy light-filled living spaces and a gourmet kitchen built for gathering, featuring custom cabinetry, stainless appliances, a professional-style gas range with statement hood, and an oversized granite island with sink and abundant storage. The spacious primary suite is a true retreat with tranquil views and a spa-inspired bath with dual vanity, soaking tub, and separate shower. Two additional bedrooms and baths provide comfort and flexibility for guests. Out back, the screened porch and patio deliver the quintessential Lowcountry backdrop-breezes through the trees, birdsong overhead, and front-row vistas across the lagoon to the fairway beyond. Callawassie Island's gated community elevates the lifestyle with an exceptional club experience, including golf, tennis, fitness, pool, dining, and miles of protected marsh and waterways.

64 Osprey Circle, Okatie

Listing courtesy of Charter One Realty.

$1,000,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-504976 MLS
This beautiful custom home features one of the very best panoramic lagoon/lake views in the community of Riverbend. It exudes serenity and will add peace and hopeful longevity to your retirement years. A possible 2878 htd sq feet if upstairs is finished. This beauty provides 3 bedrooms plus den/office, wonderful kitchen with a lot of counter space & cabinets plus a large work island. What a delight for the Chef of the home! In addition, there is a spacious breakfast area close by & a formal dining area also close by, providing ease for serving meals. Also, just a note that there is easy access to and from the garage offering ease for carrying in groceries and purchases. The gas fireplace is situated in the corner of the Great Room making the room attractive and welcoming. Many windows highlight the gorgeous lagoon view enticing you to walk out to the screened and roofed lanai where you can relax with your morning coffee or evening aperitif and watch the ducks & loons following their mommy as they swim. Nature at it's best! Another 325 sq feet upstairs that can be finished if one wishes to, in addition to a walk-in entrance to a large attic with foam insulation. There is still a warranty available on the new windows (20-yr original warranty). Several appliances are new in the last 2 years. The new brick paver driveway enhances the outdoor beauty of this house & also includes a brick paver walk-way around to the back utility yard. Come see this beautiful custom home that provides so many features including a whole house generator and much more! A whole list will be at the house, so come see this beauty!.

40 Catamaran Lane, Okatie

Listing courtesy of RE/MAX Island Realty.

$1,149,500
2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-504451 MLS
This beautiful 1,570 square foot cottage is set on 2.52 picturesque acres with sweeping golf and pond views, centrally located near Spring Island's golf facility. Built in 2010 and awarded LEED Platinum Certification, the highest distinction from the U.S. Green Building Council. This home reflects an uncompromising commitment to sustainability, energy efficiency, and quality construction. Features include autoclaved aerated concrete construction, closed-cell insulation, a tankless water heater, Energy Star appliances, and LED lighting throughout. Warmth and character define the interiors, where reclaimed wood floors, antique ceiling beams, and traditional tabby walls showcase exceptional craftsmanship and timeless materials. Each room feels distinct through the thoughtful use of textures and finishes while maintaining an open, inviting flow that is both comfortable and intimate. The living room is anchored by a charming brick fireplace with custom built-in bookcases and accented by subtle, well-placed lighting. A step-down kitchen and dining area welcomes natural light from a wall of windows and features stained concrete flooring, wood paneling, and a striking reclaimed beam. The kitchen is beautifully appointed with custom cabinetry, granite countertops, stainless steel appliances, and a nearby utility room that serves as both pantry and laundry space. The first-floor bedroom is accessed through a private hallway with custom built-ins, a bench, and closet storage, offering a quiet retreat, with full bath is conveniently located just off the hall. Upstairs, an additional bedroom suite features its own bath along with built-ins and generous closets, creating a comfortable and private space for guests or family. Outdoors, a brick patio with fire pit sits beneath a canopy of mature live oak tree providing serene setting to enjoy the natural beauty and lifestyle that embraces Spring Island's charm.

15 Bird Patch Trail, Okatie

Listing courtesy of Spring Island Realty LLC.

$3,495,000
5 Beds ⋅ 5 Baths ⋅ HILTONHEAD-504128 MLS
Located along the edge of Spring Island, where marsh meets the Colleton River, 248 Spring Island Drive offers refined Lowcountry living on 2.68 acres with expansive marsh-to-river views extending toward Port Royal and Parris Island. This 5,629-square-foot residence includes 5 bedrooms and 4.5 baths and is thoughtfully designed to maximize natural light, privacy, and seamless indoor-outdoor living. A defining feature of the home's design is the way river views are intentionally drawn through the center of the residence. The great room showcases reclaimed wood flooring, a soapstone fireplace with custom built-ins, and large windows that frame the surrounding landscape. This space opens directly to a four-season screened porch, perfectly positioned to capture sweeping marsh and river views. The dining room flows into an open den and the kitchen, creating an ideal layout for entertaining. The kitchen features leathered granite countertops, a wood-topped center island with induction cooktop, custom cabinetry with a paneled refrigerator, a wet bar, and a concealed 500-bottle temperature-controlled wine cellar. A secondary back kitchen and laundry area, hidden behind a sliding barn door, lead to a grilling patio for added convenience. An expansive artist's studio with separate HVAC and French doors opening to the gardens and river is located on the main level, offering flexible space for creative work, a home office, or additional living area. This wing also provides access to the two-car garage with golf cart bay. Upstairs guest accommodations include two ensuite bedrooms, one with a private balcony overlooking the water, along with a granite-topped kitchenette serving this level. An additional guest bedroom and a bunk room, accessed via the home's turret staircase, share a full bath-ideal for hosting family and guests. The primary suite is privately positioned to capture sunrise views over the river and features a spacious bedroom, dual walk-in closets with custom built-ins, a soaking tub, a walk-in shower, and a private office overlooking the front gardens. This exceptional property offers convenient access to Spring Island's golf, dining, equestrian facilities, deep-water access, and miles of nature trails, all while maintaining a tranquil and private riverfront setting.

248 Spring Island Drive, Okatie

Listing courtesy of Charter One Realty.

$699,900
3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-503347 MLS
This home now represents one of the finest values on Callawassie Island, granting a buyer flexibility to improve and elevate the property to their liking. Boasting phenomenal views of the newly renovated Tom Fazio Magnolia course Hole 3 green. An entertainers' dream home with an ample kitchen and luxurious wet bar with custom built-ins is the icing on the cake for this gem! Further detailed by a grand office, dining room, fireplace, and generously sized primary bedroom. An additional bedroom and full bedroom with bathroom over the garage complete the property. Natural light abounds with soaring cathedral and tray ceilings as well as oversized windows. Take pride in living in South Carolina's first certified Wildlife Habitat Community.

49 Winding Oak Drive, Okatie

Listing courtesy of Charter One Realty.

$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

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$639,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-502292 MLS
Enjoy the Callawassie Island Lifestyle, within the popular Club Cottage Section, as a Primary Home or 2nd Home with rental/investment potential. Ideally located within a short walk to Tennis, Tennis Pro-Shop & Pickleball Courts, Fitness Facility, Pool, Main Clubhouse, Golf Pro Shop and Golf Practice Facility. This well-conditioned home, with an open floor plan, exudes comfort and functionality. Tranquil pond and private Golf views of the Dogwood #1 hole. All piping replaced 2025. Callawassie Island offers an amazing community of kind people, breathtaking natural beauty, endless activities, top notch golf with total privacy and security. Furnishings are negotiable.

50 Callawassie Club Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$2,245,000
4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-503140 MLS
Located at the end of coveted Tabby Point on Callawassie Island, this riverfront gem is 3,826 sqft, 4 BD/4 BA with a 2nd story flex space. A boater's paradise, this home's private dock has both a stationary pier head dock with a floating dock + a boat lift added in 2019; adjacent to the Colleton River. The sunsets from this southwest facing property are truly something to behold. 2025 remodeled and added additional sq. ft. to the Family Room, including a new fireplace. New 2nd floor full bath. (3) HVAC's- ages 2025, 2023 & 2018. By all accounts this home maybe the highest elevation on CI and located at the confluence of the Colleton, Okatie and Chechessee Rivers.

24 Tabby Point Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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

Listing courtesy of Collins Group Realty.

$849,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-502830 MLS
Enjoy amazing sunsets from almost every room of this marsh front home. One level home with primary bedroom on one side and 2 bedrooms on the opposite side with a jack and jill bathroom. Double sided fireplace in family room and screen porch. This home offers living room, dining room, eatin kitchen, family room and Office/library for your enjoyment. 2 car garage and golf cart garage. This private gated Island Community offers Clubhouse, River Club , fitness center, 2 pools, kayak dock. Six Har-Tru Tennis courts, bocce courts, pickleball courts, dog park, 27 holes of Tom Fazio designed Golf courses and 24/7 gated security.

25 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$450,000
3 Beds ⋅ 2 Baths ⋅ 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.

$1,195,000
3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-502086 MLS
No need to wait to build your dream home. Move right into this better than new custom low country style marsh front home. Primary bedroom on first floor. Upstairs has media room and Two bedrooms with private baths as well as an outside veranda. Large screened porch. Unfinished area over two car garage and golf cart garage for future space. Outdoor grill and hot tub. Thermador appliances. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. Six Tennis courts, pickleball courts, 27 hole Golf course & 24/7 gated

4 Mayon Point, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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

Listing courtesy of Coastal Real Estate Solutions II.

$1,445,000
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

Listing courtesy of William Raveis - Carolina LLC.

$1,249,000
3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-500380 MLS
Completed in 2024, this custom Allison Ramsey-designed home sits on a 1.14-acre marshfront lot, created by consolidating part of a neighboring parcel to enhance privacy, space, and views. Designed to embrace its surroundings, the elevated home offers sweeping marsh views and a blend of Lowcountry charm and casual luxury. Built by CMS with top-tier finishes, it features approx. 2,500 sq ft, French oak floors, Andersen windows and doors, 10-foot ceilings, and a new elevator. A rare opportunity for buyers seeking a brand-new home without the time and hassle of building. The kitchen features Thermador and Bosch appliances, custom cabinetry, and a large island. Outdoor living includes a wraparound porch, tabby fireplace, gas lanterns, irrigation, and a tankless water heater.

108 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$430,000
3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-454716 MLS
Seller offering a closing credit of $75,000 with acceptable contract. All options open for either a primary home, 2nd home or investment property. This private setting Heron Walk Villa, set within beautiful mature landscaping, has views of Golf( rear) and Lagoon(front)! Golf Cart Garage and long driveway. Roof- 2023, recent bathroom renovations to both Primary Bath and Guest Bath. All plumbing water piping recently replaced. Screen porch and a separate Carolina Room/Sun Room( approx. 115 sq. ft.-unheated).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.

45 Heron Walk, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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

Listing courtesy of Charter One Realty.

$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

Listing courtesy of Coastal Real Estate Solutions II.

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