Michaelfriesproperties.com Search Results

$1,080,000

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.

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

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.

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.

$1,399,000

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.

4 Beds ⋅ 4 Baths ⋅ 3,680 SqFt. ⋅ 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

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.

3 Beds ⋅ 4 Baths ⋅ 2,580 SqFt. ⋅ 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.

$689,900

A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.

3 Beds ⋅ 4 Baths ⋅ 2,867 SqFt. ⋅ HILTONHEAD-503347 MLS

A rare chance to live in one of South Carolina's most prestigious island communities at a fraction of current market values. Set on approximately half an acre overlooking the Magnolia course's 3rd green, this 2,867 square-foot ranch offers a generous primary suite, dedicated office, formal dining, fireplace, wet bar + private bonus suite above the garage. Cathedral and tray ceilings w/ oversized windows bring natural light throughout the living spaces, while the rear deck connects the home directly to its golf setting. For buyers who value room, privacy and the ability to personalize rather than pay a premium for another's renovation, 49 Winding Oak presents a compelling entry point into Callawassie's Lowcountry lifestyle. Seller to offer buyer $37,500 in closing costs w/acceptable offer.

49 Winding Oak Drive, Okatie

Listing courtesy of Charter One Realty.

$3,479,000

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.

4 Beds ⋅ 5 Baths ⋅ 4,910 SqFt. ⋅ 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.

$2,145,000

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.

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.

$6,500,000

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.

5 Beds ⋅ 9 Baths ⋅ 8,362 SqFt. ⋅ 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

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.

3 Beds ⋅ 3 Baths ⋅ 2,925 SqFt. ⋅ 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.

$3,095,000

Situated on 3.19 acres of Lowcountry charm, this Charleston style home includes 4 bedrooms, 3 full baths and 2 half baths with 4,515 sq. ft. of an open floor plan. The home offers privacy and breath-taking views of the marsh and river with high ceilings, exquisite millwork and a renovated gourmet kitchen. The master suite, with an en-suite bathroom, feeds into a well-placed laundry room. A stunning spiral staircase leads to an office and three additional bedrooms and two full baths. The home includes a finished bonus room above the garage with extra storage. A screened porch overlooks a water feature and a native plant butterfly garden. A three-car garage and a separate shed provide enough space for gardening or simply storage. The property is also equipped with a whole home generator. HOA Amenities: Guard Gated, Palmer designed golf course, Tennis/Pickleball/ Croquet, Sports Complex, Two pools, Two Restaurants, Community boat docks, Equestrian facility, Sporting Clay Range, 30 miles of Hiking Trails and a fully staffed Nature Center.

4 Beds ⋅ 5 Baths ⋅ 4,505 SqFt. ⋅ HILTONHEAD-447902 MLS

Situated on 3.19 acres of Lowcountry charm, this Charleston style home includes 4 bedrooms, 3 full baths and 2 half baths with 4,515 sq. ft. of an open floor plan. The home offers privacy and breath-taking views of the marsh and river with high ceilings, exquisite millwork and a renovated gourmet kitchen. The master suite, with an en-suite bathroom, feeds into a well-placed laundry room. A stunning spiral staircase leads to an office and three additional bedrooms and two full baths. The home includes a finished bonus room above the garage with extra storage. A screened porch overlooks a water feature and a native plant butterfly garden. A three-car garage and a separate shed provide enough space for gardening or simply storage. The property is also equipped with a whole home generator. HOA Amenities: Guard Gated, Palmer designed golf course, Tennis/Pickleball/ Croquet, Sports Complex, Two pools, Two Restaurants, Community boat docks, Equestrian facility, Sporting Clay Range, 30 miles of Hiking Trails and a fully staffed Nature Center.

224 Spring Island Drive, Okatie

Listing courtesy of Spring Island Realty LLC.

$2,750,000

Nestled in the privacy of Spring Island, this home offers luxurious living with beautiful views of Lower Goose Pond. This property features a meticulously crafted main house with 3 bedrooms, 3.5 baths, and exquisite pine wood flooring. Above the detached garage, guests will find comfortable quarters including a full bathroom and half bathroom, ensuring privacy and convenience. Step out to the screened porch to discover serene living spaces. Residents of Spring Island enjoy exclusive access to world-class amenities such as golf, equestrian facilities, tennis courts, boating, arts, and scenic trails. All info is deemed correct, buyer to verify.

4 Beds ⋅ 6 Baths ⋅ 4,895 SqFt. ⋅ HILTONHEAD-443882 MLS

Nestled in the privacy of Spring Island, this home offers luxurious living with beautiful views of Lower Goose Pond. This property features a meticulously crafted main house with 3 bedrooms, 3.5 baths, and exquisite pine wood flooring. Above the detached garage, guests will find comfortable quarters including a full bathroom and half bathroom, ensuring privacy and convenience. Step out to the screened porch to discover serene living spaces. Residents of Spring Island enjoy exclusive access to world-class amenities such as golf, equestrian facilities, tennis courts, boating, arts, and scenic trails. All info is deemed correct, buyer to verify.

181 Spring Island Drive, Okatie

Listing courtesy of Spring Island Realty LLC.