Callawassie Island Homes with Two Story Style

Welcome to Callawassie Island, a hidden gem nestled in the heart of South Carolina's Beaufort County. This serene island community, located just outside the charming city of Okatie, offers a unique blend of natural beauty, southern charm, and a vibrant lifestyle. With its picturesque landscapes, lush marshes, and stunning views of the Colleton River, Callawassie Island is a paradise for those seeking tranquility and a connection with nature.

One of the standout features of this enchanting community is its exquisite collection of two-story homes. These residences not only provide ample living space but also offer a perfect vantage point to soak in the breathtaking surroundings. Imagine waking up to the gentle sounds of nature, sipping your morning coffee on a spacious balcony, or hosting family gatherings in an inviting, open-concept living area that flows seamlessly from room to room.

The two-story homes on Callawassie Island are designed with both elegance and functionality in mind. Many feature modern amenities, gourmet kitchens, and luxurious master suites, all while maintaining a classic lowcountry aesthetic. With a variety of architectural styles, you’re sure to find a home that resonates with your personal taste.

Beyond the beautiful homes, Callawassie Island fosters a strong sense of community, with numerous amenities such as golf courses, walking trails, and social clubs. Whether you’re an outdoor enthusiast or someone who appreciates a vibrant social life, this island offers the perfect backdrop for creating lasting memories. Discover your dream home on Callawassie Island and let the beauty of South Carolina embrace you!

Newest Callawassie Island Homes with Two Story Style

$3,600,000

5 Beds ⋅ 7 Baths ⋅ 6,351 SqFt. ⋅ HILTONHEAD-511577 MLS

Opportunities like this come along once in a lifetime. 9 & 8 Woodstork Watch is a rare offering on Callawassie Island, a 2.41-acre estate that stands as a true legacy property, meticulously crafted and cared for over decades. Originally assembled from four separate lots, the property has now been approved for consolidation into a single parcel carrying one Callawassie Island membership, creating an estate of exceptional scale and privacy rarely found on the island. Situated at the end of a quiet cul-de-sac and occupying the end of a point, the property enjoys a rare and private setting, with its position offering incredible sunrise and sunset views over the water. The main residence, completed in 2001, embraces classic lowcountry design and reflects a level of craftsmanship and woodwork rarely found today: reclaimed flooring, three masonry fireplaces, and a marsh-inspired palette that ties the home to its natural surroundings. The guest house and boathouse, known as "Captain's Quarters," bring a European lowcountry sensibility to the waterfront, extending the same quality and attention to detail found throughout the main residence. Together, the two homes offer a timeless architectural character and a level of craftsmanship that place this estate in a class of its own. The primary suite offers its own private porch, one of multiple private outdoor spaces throughout the property that take full advantage of the setting. Complete with a private boat dock and lift, the estate offers effortless waterfront living. Its stature was further recognized when it was featured in From House to Home in 2009, cementing its place as one of Callawassie Island's architecturally significant properties. Properties of this caliber, with this depth of design history, craftsmanship, and multi-generational care, rarely become available.9 Woodstork Watch stands as a rare opportunity for a buyer seeking not just a home, but a retreat, and a legacy.

9 Woodstork Watch, 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.

$1,075,000

4 Beds ⋅ 4 Baths ⋅ 2,965 SqFt. ⋅ 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.

$1,050,000

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.

$1,100,000

3 Beds ⋅ 4 Baths ⋅ 2,734 SqFt. ⋅ 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.

$1,195,000

3 Beds ⋅ 4 Baths ⋅ 3,512 SqFt. ⋅ 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.

$2,895,000

5 Beds ⋅ 5 Baths ⋅ 3,906 SqFt. ⋅ 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.

6 Dolphin Landing, Okatie

Listing courtesy of Charter One Realty.

$900,000

4 Beds ⋅ 4 Baths ⋅ 3,925 SqFt. ⋅ 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. (Digital enhancement has been used in some photographs)

4 Bent Tree Lane, Okatie

Listing courtesy of Charter One Realty.

$1,399,999

4 Beds ⋅ 5 Baths ⋅ 3,441 SqFt. ⋅ 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 ⋅ 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.

$329,000

3 Beds ⋅ 2 Baths ⋅ 1,636 SqFt. ⋅ HILTONHEAD-505169 MLS

Welcome to 49 Heron Walk on Callawassie Island. Perfectly positioned on the fairway of the 1st 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, use as a 2nd home or create income as a sought-after retreat for visiting golfers. This is island living with timeless style. Optional Golf Membership.

49 Heron Walk, Okatie

Listing courtesy of Moul, REALTORS®.

$2,145,000

4 Beds ⋅ 4 Baths ⋅ 3,826 SqFt. ⋅ 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.

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