Callawassie Island Homes with Trees/Woods View

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Newest Callawassie Island Homes with Trees/Woods View

$899,000

4 Beds ⋅ 4 Baths ⋅ 3,587 SqFt. ⋅ HILTONHEAD-512387 MLS

This quintessential Lowcountry home offers easy one-story living amid exceptional private surroundings on Callawassie Island. Thoughtfully positioned in one of the most desirable settings, 1 S Oak Forest sits directly across from the picturesque butterfly garden and beside protected green space, creating a beautiful natural backdrop and an uncommon sense of privacy, while remaining just steps from the River Club, community pool, and boat docks. The spacious open floor plan is filled with natural light and flows into the gourmet kitchen and rear Carolina room overlooking a tranquil natural oasis. Meticulously maintained, the home features custom built-ins, plantation shutters, generously sized rooms, and a dedicated office. A charming guest suite above the garage includes a kitchenette and full bath, offering a comfortable space for guests or extended stays. Recent improvements provide added peace of mind, including a brand-new architectural roof with transferable warranty, freshly painted exterior, and two nearly new HVAC units. Callawassie Island is considered by many to be one of the best locations in Beaufort County, offering an exceptional Lowcountry lifestyle with world-class amenities, including Tom Fazio golf, waterfront clubhouses, a fitness facility, community pools, boat docks, and more. A rare combination of privacy, nature, convenience, and thoughtful updates, 1 S Oak Forest is a wonderful place to call home.

1 S Oak Forest Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,360,000

4 Beds ⋅ 5 Baths ⋅ 3,030 SqFt. ⋅ HILTONHEAD-512044 MLS

Southern Living, brought to life on Callawassie Island. Built in 2025 from a featured Southern Living floor plan, the River Place Cottage is better than new, with more than $100K in thoughtful owner upgrades. Tucked on a quiet Heron Point cul-de-sac with no through traffic, a wide front porch welcomes you into a light-filled home where warm hardwood floors, exposed beams, and elevated finishes create an immediate sense of relaxed elegance. The open kitchen, dining, and living areas flow effortlessly for everyday living and entertaining, anchored by a custom fireplace surround with gas insert and complemented by designer lighting. Just off the dining area, sliders open to a spacious screened porch, extending the living space and creating the seamless indoor/outdoor connection Lowcountry living is known for. The private main-level primary suite features a spa-like bath with a soaking tub, while a dedicated study offers a quiet place to work or unwind. Out back, a covered porch leads to an expansive custom paver patio and fire pit, with generous green space, enhanced landscaping, and beautiful views of Dogwood #6 beyond-an idyllic setting for morning coffee, evenings around the fire, or entertaining friends. Upstairs, hardwood floors continue through two spacious ensuite bedrooms with abundant storage. A detached 2-car garage with dedicated golf cart bay and epoxy floors is topped by a 558-square-foot FROG with full bath and closet-ideal as a private guest suite, gym, or flex space. Fresh interior paint, exterior shutters, and numerous additional improvements mean the work has already been done. And beyond your front door, enjoy the lifestyle that makes Callawassie Island so special-27 holes of golf, boating and river access, racquet sports, pools, fitness, dining, and a welcoming social community, all surrounded by the natural beauty of the Lowcountry. Beautifully finished, thoughtfully upgraded, and completely move-in ready-this is a home designed to be enjoyed from day one.

14 Heron Point, Okatie

Listing courtesy of The Agency Hilton Head.

$1,379,000

3 Beds ⋅ 3 Baths ⋅ 2,462 SqFt. ⋅ HILTONHEAD-512149 MLS

Tucked beneath a canopy of trees on desirable Osprey Circle, mid-island in Magnolia #7, this home feels like a private retreat, completely redesigned and rebuilt from the studs by a premier contractor, with no expense spared and no detail overlooked. Eastern exposure fills the home with soft morning light, while shaded afternoons and a long, private view of the golf course create a quiet, elevated sense of place.Essentially reborn as a new home, the residence was reconstructed with all-new stucco and exterior painting, all-new electrical, and all-new plumbing throughout. The interior showcases gorgeous segmented arches throughout, offering beautiful architectural character alongside 8' solid-core doors and hardwood flooring laid with laser precision. A redesigned hallway flows through graceful new archways into the kitchen and dining room, where custom wainscoting lends a refined, tailored finish. The kitchen is anchored by Taj Mahal quartzite countertops, while the spa-inspired bathrooms are finished in quartz, with redesigned tile showers and a master suite featuring a freestanding pedestal tub and brass fixtures.The Carolina room has been thoughtfully redesigned to frame the wooded, golf-course backdrop, with new screening and a glass door that blurs the line between indoors and out. Additional refinements include a butler's pantry with dry-bar and wine cooler, hurricane-impact windows, a tankless water heater, blown-foam attic insulation, and a fully restuccoed, stone-accented exterior complemented by newly curated landscaping.For the buyer who values craftsmanship and quality above all, this is a rare offering: a true turnkey residence where every element has been considered. Move in with complete peace of mind and begin your Callawassie Island Lifestyle.

90 Osprey Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 3,103 SqFt. ⋅ HILTONHEAD-510836 MLS

Tucked at the end of a quiet cul-de-sac and shared by only four residences, this Classic Lowcountry-style home offers a rare combination of privacy, pedigree, and place. Originally built by Steve Tilton of Coastal Signature Homes, the residence reflects the craftsmanship and thoughtful detailing this builder is known for, from refined millwork to finishes selected with an eye for timeless quality.The setting is equally exceptional. Recently expanded to 1.09 acres, the property is canopied by mature Live Oaks and offers partial marsh views, creating a sense of seclusion that's increasingly rare to find. With only three neighboring homes on the entire street, this feels less like a residential lot and more like a private retreat, the kind of privacy that simply can't be recreated.This is Lowcountry living at its most authentic: classic architecture, masterful construction, and a setting defined by nature, quiet, and space to breathe.

6 Winding Oak Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$799,000

3 Beds ⋅ 3 Baths ⋅ 2,108 SqFt. ⋅ HILTONHEAD-510356 MLS

Welcome to 13 River Marsh Lane, a charming Lowcountry cottage nestled within the desirable Cottage Section of Callawassie Island-one of the few areas where short-term rentals are permitted, offering exceptional flexibility for homeowners and investors alike. Sold fully furnished, this turnkey property is ready for immediate enjoyment or income-producing potential. This beautifully maintained 3-bedroom, 2.5-bath home blends timeless Southern charm with modern comfort. Hardwood floors, abundant natural light, and inviting living spaces create a warm and welcoming atmosphere. The thoughtfully updated kitchen and baths complement the home's classic coastal character, while front and rear porches provide the perfect setting to enjoy the island's peaceful surroundings. Located just moments from Callawassie Island's world-class amenities, including 27 holes Tom Fazio golf, tennis, pickle ball, bocce, fitness, dining, and waterfront recreation, this property offers an exceptional opportunity to embrace the Lowcountry lifestyle. Whether you're seeking a primary residence, vacation retreat, or investment property, 13 River Marsh Lane delivers the best of island living.

13 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$914,000

4 Beds ⋅ 3 Baths ⋅ 2,801 SqFt. ⋅ HILTONHEAD-509015 MLS

Nestled on a private circle within the prestigious Callawassie Island community, 8 Chechessee Circle is a beautifully renovated Lowcountry retreat where timeless elegance meets breathtaking natural beauty. Surrounded by majestic live oaks draped in Spanish moss, this thoughtfully updated home offers sweeping marsh and tidal creek views, creating a peaceful sanctuary for nature lovers and those seeking refined coastal living. Designed with both comfort and sophistication in mind, expansive windows fill the home with natural light while showcasing the stunning scenery from nearly every room. The spacious great room features cathedral ceilings, custom bookshelves with storage, and an updated fireplace, creating a warm and inviting gathering space. The great room flows seamlessly into the updated kitchen and four-season Carolina room, making the home ideal for both entertaining and quiet relaxation. Recent improvements include upfitted kitchen cabinets, new kitchen appliances, countertops, and a farmhouse sink, along with wide-plank engineered English oak floors and a new HVAC system (2026), bringing modern style and comfort throughout the home. The primary suite offers a serene escape with tranquil marsh views, a beautifully renovated bath, and generous his-and-her walk-in closets. Flexible living spaces provide options for a home office, formal dining room, or additional guest accommodations, allowing the home to adapt easily to a variety of lifestyles. Outdoor living is equally inviting, with a shaded deck that provides the perfect setting for morning coffee while taking in the peaceful marsh views and abundant Lowcountry wildlife. Located within the private, gated golf community of Callawassie Island, residents enjoy access to world-class amenities including 27 holes of Tom Fazio-designed golf, tennis, pickleball, fitness facilities, community docks, dining, pools, and miles of scenic marshfront beauty. Ideally positioned between Beaufort, Bluffton, Hilton Head, and Savannah, 8 Chechessee Circle offers the perfect balance of privacy, luxury, natural beauty, and convenience.

8 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,899,900

4 Beds ⋅ 5 Baths ⋅ 4,470 SqFt. ⋅ HILTONHEAD-508950 MLS

Brand-new custom luxury Lowcountry retreat nestled near the end of the peninsula on a quiet, private wooded cul-de-sac in desirable Woodstork Watch on Callawassie Island, surrounded by similarly impressive high-end custom homes. This expansive newly constructed residence offers stunning high-tide marsh views and exceptional craftsmanship throughout, including energy-efficient 2x6 construction and spray foam insulation. Designed to embrace the Lowcountry lifestyle, the home features seamless indoor and outdoor living transitions on both the first and second levels, creating inviting spaces for entertaining and relaxation. Soaring cathedral ceilings enhance the open and airy feel of the main living spaces, while sophisticated custom black steel railings add striking architectural detail throughout the home. The gourmet JennAir kitchen is designed for entertaining with a massive center island, six-burner gas range, premium appliances, and an elegant scullery for added prep and storage space. An expansive upstairs loft with private balcony captures peaceful marsh views and offers additional living and gathering space. A full private living area above the garage with its own kitchenette provides ideal space for guests, extended family, or multigenerational living. Enjoy refined finishes, modern luxury, and the perfect blend of privacy and Lowcountry beauty in one of the island's most sought-after settings. Widely regarded as one of the premier locations in Beaufort County, Callawassie Island offers an exceptional Lowcountry lifestyle with convenient access to Beaufort, Bluffton, Hilton Head Island, and the historic cities of Charleston and Savannah.

7 Woodstork Watch, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$849,000

3 Beds ⋅ 3 Baths ⋅ 2,303 SqFt. ⋅ HILTONHEAD-507814 MLS

Completely reimagined and impeccably renovated, 5 Oyster Court on Callawassie Island is a true Lowcountry gem that blends timeless charm with modern sophistication. Every detail has been thoughtfully curated in this top-to-bottom transformation, showcasing high-end finishes, designer touches, and quality craftsmanship throughout. The well-designed floor plan offers comfortable, easy living and effortless flow for entertaining, while the stunning updated kitchen serves as the heart of the home with premium appliances, custom cabinetry, and elegant surfaces. The spacious primary suite provides a serene retreat, complemented by beautifully renovated baths that evoke a spa-like experience. Additional guest rooms offer comfort and privacy, and the third bedroom offers flexibility as an ideal home office or study. Extending across the entire back of the home, an oversized screened porch creates the perfect setting for relaxing or entertaining while enjoying the peaceful Lowcountry surroundings. Significant upgrades provide added value and peace of mind, including all new windows, new HVAC system, and new hot water heaters. Nestled on a quiet cul-de-sac, the property offers a tranquil setting with inviting outdoor spaces to enjoy the natural beauty of Callawassie Island. Ideally located just moments from the River Club, deep water docks, and family pool, this home provides easy access to some of the community's most sought-after amenities. This move-in-ready home presents a rare opportunity to own a fully renovated residence in one of the Lowcountry's most desirable private communities, known for its championship golf, deepwater access, and exceptional amenities.

5 Oyster Court, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,080,000

4 Beds ⋅ 4 Baths ⋅ 3,000 SqFt. ⋅ 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®.

$1,025,000

4 Beds ⋅ 4 Baths ⋅ 3,990 SqFt. ⋅ 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. Recent updates include a brand-new roof (2026) and new HVAC system (2025), adding value and move-in-ready confidence. 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 and 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.

$459,000

HILTONHEAD-503416 MLS

Rarely does an opportunity arise to own one of the most significant waterfront parcels in the Lowcountry. This exceptional 1.15-acre homesite on Callawassie Island represents one of the largest available properties in this award-winning 880-acre private community. Situated with wide-open northeastern exposure, the site captures breathtaking sunrises across shimmering tidal creeks and vibrant salt marshes. Surrounded by centuries-old live oaks and Spanish moss, the landscape provides a timeless backdrop for a legacy estate. Callawassie Island offers a premier Lowcountry lifestyle centered on 27 holes of Tom Fazio-designed golf, professional-grade racquet facilities, and dual clubhouses that provide deepwater access and luxury wellness amenities within South Carolina's first certified Community Wildlife Habitat. Strategically situated in the heart of Beaufort County, Callawassie Island is almost equidistant from the historic charm of Beaufort and the bustling center of Bluffton, placing residents within a 35-minute drive of Hilton Head Island, Savannah, Georgia, and the Savannah/Hilton Head International Airport.

32 Winding Oak Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$450,000

3 Beds ⋅ 2 Baths ⋅ 1,861 SqFt. ⋅ HILTONHEAD-502715 MLS

26 Heron Walk stands out as one of the largest villas in the Village section, offering 1,861 sq ft of thoughtfully designed living space. This inviting home features a large Carolina Room and a detached full garage with golf-cart bay. Designed for comfort and flexibility, it offers open living areas and exceptional privacy with serene lagoon and golf-course views. Upstairs, the beautifully updated second-story bath has been used as a primary suite during current ownership, enhancing the home's versatility and livability. New Roof-2026. Located within the private, gated community of Callawassie Island, residents enjoy access to newly renovated Tom Fazio-designed golf courses, deep-water access, club dining, fitness facilities, pools, tennis, pickleball, bocce, and more. Life on Callawassie Island offers an unmatched blend of natural beauty, community connection, and the timeless charm of Lowcountry living.

26 Heron Walk, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

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