Callawassie Island Homes with Two Story Architectural Style

Welcome to Callawassie Island, a hidden gem nestled in the heart of Beaufort County, South Carolina. This picturesque subdivision, located in the charming city of Okatie, offers a unique blend of natural beauty and refined living, making it an ideal destination for those seeking a serene yet vibrant community.

Callawassie Island is renowned for its stunning landscapes, featuring lush greenery, serene waterways, and breathtaking views of the Lowcountry’s marshes. The community is designed to embrace the natural surroundings, with an array of outdoor activities, including kayaking, fishing, and nature trails, perfect for those who appreciate an active lifestyle.

Among the architectural styles found within Callawassie Island, the two-story homes stand out for their elegance and spaciousness. These homes are thoughtfully designed to maximize both comfort and style, offering ample living space for families or those looking to entertain. With soaring ceilings, open floor plans, and large windows that invite in natural light, these two-story residences create a warm and inviting atmosphere. Many homes also feature expansive decks or balconies, allowing residents to enjoy the stunning views and gentle breezes that the island offers.

The community fosters a strong sense of belonging, with an array of amenities including a clubhouse, golf course, and swimming pools, ensuring that residents have everything they need right at their fingertips. Whether you’re taking a leisurely stroll along the winding paths or enjoying a sunset on your porch, Callawassie Island is more than just a place to live; it’s a lifestyle waiting to be embraced. Discover the charm and tranquility of this exceptional community today!

Newest Callawassie Island Homes with Two Story Architectural Style

$1,395,000

4 Beds ⋅ 5 Baths ⋅ 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 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 firepit, 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.

$1,075,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511584 MLS

Among the Best Golf/Marsh views within Callawassie Island. This Club Cottage, at 2,965 sq. feet, has 4 bedrooms, 3 1/2 bath and terrific long views of the complete Dogwood 9th hole, bridge/lagoon and tidal marsh views. Primary Bedroom on 1st floor, with 2 bedrooms upstairs with an optional 4th bedroom or office. The Upstairs Bedroom private veranda provides even more elevated spectacular views. Callawassie Island Club Cottage Section is ideal for either a primary home, a 2nd home or a rental investment property. Callawassie Island Lifestyle offers, breathtaking natural beauty, endless activities, newly renovated Tom Fazio designed 27 holes of golf (optional) with total privacy and security.

24 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 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.

$1,150,000

3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-510205 MLS

An incredible opportunity and unbelievable value to have three wonderful views of marsh, lagoon, and golf. This charming recently renovated Lowcountry Club Cottage is move in ready and yours to enjoy morning sunrises over the marsh. Located on the finishing 9th hole of the Dogwood course, this open floor plan with high ceiling is perfect for entertaining. 3 bedrooms, 1st-floor master, 3.5 baths, 2nd floor Guest Suite with terrific three views. Large screened in porch and backyard offer a great outdoor living space. 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). 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.

14 River Marsh Lane, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$1,899,900

4 Beds ⋅ 5 Baths ⋅ 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.

$1,285,000

3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-508587 MLS

Nestled within one of the most scenic settings on Callawassie Island, this exceptional custom-built Lowcountry home captures miles of sweeping marsh, river, and golf views, all paired with incredible sunsets and refreshing summer breezes. Thoughtfully designed to embrace its stunning surroundings, the home offers expansive porches and decks that create a seamless indoor-outdoor living experience. Crafted with timeless quality and architectural character throughout, features include a lifetime metal roof, 10-foot ceilings, Pella windows and doors, reclaimed Southern pine flooring, 8-foot solid core doors, and extensive custom cabinetry and built-ins. The beautifully appointed designer kitchen showcases limestone and granite countertops, a gas cooktop, and refined finishes ideal for both everyday living and entertaining. Additional details such as crown molding throughout the first floor and oil enamel painted casework and doors further elevate the home's craftsmanship and warmth. The spacious second-floor bedroom retreat includes a private sitting room, while the detached garage offers a beautifully designed guest suite complete with its own kitchenette-ideal for visitors, multigenerational living, or private workspace flexibility. Residents enjoy the unmatched lifestyle of Callawassie Island-a private gated island community known for its remarkable natural beauty, welcoming atmosphere, deep-water access, top-tier golf and amenities (optional), endless outdoor recreation, and the peaceful charm of true Lowcountry living.

10 Island Creek Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$2,995,000

5 Beds ⋅ 5 Baths ⋅ HILTONHEAD-508380 MLS

A different rhythm takes hold at Callawassie Island, a canopy of live oaks, tidal marsh, and quiet surroundings create a setting that feels worlds away. At the end of a cul-de-sac, on Dolphin Landing, this newly constructed custom home emerges with quiet confidence. From the moment you step inside, the experience is immediate. The great room opens to long, unobstructed views, anchored by a dramatic sleek fireplace with Old World tabby surround. Soaring ceilings, rich wood floors, and custom detailing create a sense of volume while allowing light and landscape to take center stage. The kitchen is defined by striking architectural detail, including a coffered ceiling, an oversized island, and is equipped with Sub-Zero refrigeration and a Wolf six-burner range with double ovens. A private prep space, walk-in pantry, and adjoining laundry/mudroom provide function and flow, with direct access to the outdoor summer kitchen. Privately positioned, the primary suite captures serene views with a wood feature wall, dual dressing areas, and a bath of notable scale and sophistication. Each additional bedroom offers an ensuite with double vanities and walk-in closets. The distinctive private carriage house above the three-car garage includes a separate entrance, kitchenette, bedroom, full bath, and walk-in closet-ideal for extended stays and finished with the same level of craftsmanship carried throughout the residence. Outdoor living is equally compelling, with a screened porch overlooking the marsh where wildlife and shifting tides create a dynamic backdrop. Positioned for uninterrupted views and golden hour exposure, the setting offers a rare sense of privacy. Every detail has been intentionally designed from the climate controlled wine room and tabby accents to the layered textures, custom finishes, and thoughtfully crafted elements reflected throughout the home. A rare opportunity to own a newly built home of this caliber within one of the Lowcountrys most private and naturally beautiful communities. Enjoy an exclusive buyer benefit: with an accepted offer, the Seller will pay the one-time Club Initiation Contribution Fee, allowing you to begin enjoying all that Callawassie Island has to offer from day one.

6 Dolphin Landing, Okatie

Listing courtesy of Charter One Realty.

$899,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-506792 MLS

Completely renovated and thoughtfully improved, this Lowcountry cottage offers a rare opportunity to enjoy privacy, natural beauty, and move in ready living on Callawassie Island. Set on a 1.41 acre wooded homesite, the property welcomes you with three sets of mahogany French doors across the front, filling the home with natural light and creating a seamless connection to the outdoors. Ideally positioned across from the marsh, the home is a short walk to a community dock with access to tidal waterways and sunset views. Interior updates include new flooring and carpeting, energy efficient lighting, and dimmers throughout. The living room and primary suite feature bricked fireplaces, and a custom built bar with a beverage refrigerator is perfectly located between the living room and dining room, enhancing both flow and functionality. The dining room is highlighted by a designer chandelier by Frederick Raymond. The kitchen has been updated with refreshed finishes. The powder room has been opened and improved with quality fixtures. Additional upgrades include new windows, updated hardware, and improved lighting throughout. Exterior improvements include updated railings, new outdoor lighting, paver driveway accents, a landscaped walkway, irrigation system, and all new exterior doors throughout. This property offers a unique combination of charm, privacy, and proximity to the water in one of Callawassie Island's most desirable settings.

25 Chechessee Circle, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$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.

$1,399,999

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.

$1,025,000

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.

$329,000

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®.

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