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$500,000
3 Beds 3 Baths 2,398 SqFt. HILTONHEAD-502567 MLS
Welcome to Callawassie Island, a private gated island sanctuary community with numerous amenities. With a new roof, this spacious 3 bedroom, 2.5 bath one level is perfectly framed by sweeping views of Spanish moss-draped oaks and the Tom Fazio "Palmetto" course. Sunlight filters through generous windows, illuminating architectural details. With vaulted ceilings and a wall of windows, the inviting great room is anchored by the fireplace. Entertaining is easy with the spacious dining area open to the kitchen. The kitchen showcases custom wooden cabinetry and a walk-in pantry. The tranquil primary suite overlooks the wide views and offers a jetted spa tub, walk-in shower and dual vanities. A large two car garage with a dedicated golf cart bay, this home is priced for you to add your personal touches.

9 Winding Oak Drive, Okatie

Listing courtesy of Keller Williams Realty. Selling Office: William Raveis - Carolina LLC.

$750,000
3 Beds 3 Baths 2,104 SqFt. HILTONHEAD-502751 MLS
Ideally located midway between Beaufort and Bluffton, this furnished, move-in ready Callawassie Island home was originally renovated in 2020 and thoughtfully improved again in 2025. Filled with natural light, it offers peaceful views of the Palmetto #4 green on the newly renovated Tom Fazio-designed course.The kitchen features VIKING stainless steel appliances, while a spacious screened porch creates an easy, inviting flow for everyday living and entertaining. A 2023 roof and Wi-Fi-enabled water heater add efficiency and peace of mind.Recent interior updates include solid wood closet shelving, new LED lighting, fresh interior paint, a whole-home audio system, four mounted TVs, and six Ring cameras. The foundation was reinforced with new footer supports in 2024 and passed follow-up inspection with no issues, with all prior inspection items addressed.Exterior improvements include freshly painted decks, stairs, and railings. Callawassie Island residents enjoy golf, deep-water docks, dining, fitness, pools, tennis, pickleball, bocce, and more.

3 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Coastal Real Estate Solutions II.

$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.

$1,415,000
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.

$1,075,000
4 Beds 5 Baths 3,460 SqFt. HILTONHEAD-500696 MLS
Situated with a panoramic view of the golf course, this Lowcountry style custom home is surrounded by majestic oaks & blooming magnolias. Home has a large primary suite and two bedrooms on the first floor. A finished suite over the garage offers privacy and comfort for guests. A charming screened porch provides an escape to relax or for entertaining. Home is detailed with Andersen windows, reclaimed pine floors, and custom cabinetry. Freshly painted throughout. Renovated kitchen with adjacent breakfast area and family room. New paver patio and built in grill. Two tankless hot water heaters. HVAC 2017 main house. Private gated Island Community offers Clubhouse, River Club, fitness center, 2 pools, kayak dock. 6 tennis courts, pickleball courts, Bocce courts, dog park, 27 hole Golf course & 24/7 gated security.

56 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Keller Williams Realty.

$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.

$1,249,000
3 Beds 3 Baths 2,500 SqFt. 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.

$657,500
3 Beds 3 Baths 2,961 SqFt. HILTONHEAD-453990 MLS
Beautiful one-level living with an open, vaulted floor plan perfect for entertaining and enjoys gorgeous private views! This 2,961SF, 3BD, 3BA home features a spacious flex room ideal for a workshop, game room, or golf simulator. Looking to avoid steps? Don't miss the best value on Callawassie Island at $225/sf! Recent upgrades include interior/exterior paint, HVAC, flooring, kitchen appliances, and more. The outdoor living can't be beat with a vaulted screened porch, paved patio, fire pit, and grilling area. Callawassie's top-tier amenities include 24/7 security, tennis, pickleball, fitness, deep-water docks, dining, and recently renovated 27 holes of Tom Fazio golf. Come check out the Callawassie magic; it's worth the trip!

3 Longwood Court, Okatie

Listing courtesy of Charter One Realty. Selling Office: Coastal Real Estate Solutions II.

$900,000
4 Beds 5 Baths 3,543 SqFt. HILTONHEAD-450920 MLS
Welcome to Southern elegance at its finest! Nestled on a private and serene 0.80-acre lot, this stately custom Lowcountry home is the perfect blend of charm, comfort, and sophistication. The main residence offers 3 bedrooms and 3.5 bathrooms, while a beautifully appointed guest cottage provides an additional 1 bedroom and 1 bathroom ideal for visitors or multi-generational living. Designed with entertaining in mind, the open and airy layout features a chefs kitchen, formal dining room, and a spacious family room with a dual-sided gas fireplace that flows seamlessly into the great room. The first-floor primary suite is a true retreat, complete with a luxurious en-suite bath and a generous walk-in closet. Step outside to a covered porch perfect for morning coffee or evening gatherings, all surrounded by lush landscaping and upscale custom finishes throughout. Experience the best of island living and take advantage of the premier amenities this sought-after community has to offer. Schedule your private tour today this is Lowcountry living at its finest! *Seller will pay half of HOA initiation with accepted offer*

21 Osprey Circle, Okatie

Listing courtesy of Redfin Corporation. Selling Office: Charter One Realty.

$750,000
3 Beds 3 Baths 2,249 SqFt. HILTONHEAD-449131 MLS
A Classic Southern Living Cottage, with functional design and craftsman quality built, set in a private wooded setting on .74 acre. Enjoy expansive golf course views from the curved, wraparound heated rear screened porch. An open chef's kitchen is the heart of this 3 bedroom, 2.5 bath cottage. High ceilings, wide plank hardwood floors throughout, featuring a Savannah brick fireplace. The private office/den,1st floor master suite, & two 2nd floor guest rooms w/spacious guest bath. Detached 2 car garage w/connecting breezeway. Spray foamed attic & crawl space. New roof 2024, both new HVAC's 2024, gas tankless water heater & generator conveys!

58 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: William Raveis - Carolina LLC.

$2,100,000
5 Beds 7 Baths 5,259 SqFt. HILTONHEAD-447631 MLS
New construction on very private lot overlooking the Colleton River with gorgeous southern exposure. Tons of space including 1st floor primary suite, light-drenched kitchen that opens to living room and breakfast nook, formal dining room and office. Second floor features 3 bedrooms with bath en suites, plus den. Huge top floor with separate bath offers great flex space with tons of creative options. Don't miss the carriage apartment located above the spacious 3-car garage. Callawassie Island is a private Sea Island gem offering extraordinary golf, deep water dock access, fitness center, racquet facilities, club house, river club and 2 pools.

7 Winding Oak Court, Okatie

Listing courtesy of William Raveis - Carolina LLC. Selling Office: Daniel Ravenel Sotheby's International Realty.

$1,100,000
4 Beds 6 Baths 4,797 SqFt. HILTONHEAD-446975 MLS
Privacy awaits at your outdoor oasis with heated saltwater pool and outdoor kitchen. Enjoy views of Magnolia #5 green/lagoon from your elevated main living spaces, screened porch & patio. Craftsmanship can be felt the moment you walk thru the Mahogany Front doors into 14-16' ceilings with custom moldings & trim. Every bedroom has its own full bathroom, as does the large bonus/5th bedroom over the 2.5 car garage. Upgrades include new White Oak Flooring & paint throughout main floor('24), New Roof('24), Whole House Generac('23), 2 new HVACs('22), 2 new Rinnai tankless hwhs('22), new GE Cafe appliances('22), plus much more. Golf Cart Included.

109 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

$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.

$1,079,975
3 Beds 3 Baths 2,435 SqFt. HILTONHEAD-446412 MLS
Fantastic New Artisan Custom Home Move-in Ready near year's end thoughtfully situated on the New Magnolia Course w/Great Elevation! The Bayberry is one of Artisan Custom Homes’ most efficient floor plans. Featuring 2,435sqft of One Level Living, three bedrooms, two baths, vaulted kitchen and great room, dining room, office, generous pantry and laundry room. In addition there is an attached two and a half car garage w/ bonus room. The Large screen porch compliments the rear of home and offers the ultimate location to enjoy Lowcountry Outdoor Living at its Finest! Callawassie Island is Considered by many as the best location in Beaufort County!

61 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II. Selling Office: Coastal Real Estate Solutions II.

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