Hilton Head Island Homes with Private Pool

Welcome to Hilton Head Island, South Carolina – a stunning coastal paradise known for its pristine beaches, lush landscapes, and vibrant community. Nestled in Beaufort County, this charming island offers an idyllic blend of relaxation and adventure, making it a sought-after destination for both vacationers and homeowners alike.

Hilton Head Island boasts a rich tapestry of activities, from world-class golf courses and tennis facilities to scenic biking trails and water sports. The island’s natural beauty is complemented by its commitment to preserving the environment, ensuring that residents and visitors can enjoy the breathtaking coastal scenery for generations to come. With a mild climate year-round, outdoor enthusiasts can bask in the sun or explore the island's diverse wildlife at any time of the year.

For those seeking the ultimate in luxury and comfort, homes with private pools are a perfect choice. Imagine unwinding in your own oasis after a day spent soaking up the sun on the beach or exploring the island’s many attractions. These exquisite properties offer not only a refreshing retreat but also the perfect space for entertaining family and friends.

Whether you’re looking for a spacious family home or a cozy getaway, Hilton Head Island’s real estate market features a variety of options to suit your needs. With private pools as a standout feature, these homes provide a unique opportunity to embrace the island lifestyle fully. Discover your dream home on Hilton Head Island, where every day feels like a vacation!

Newest Hilton Head Island Homes with Private Pool

$1,800,000

3 Beds ⋅ 3 Baths ⋅ 2,178 SqFt. ⋅ HILTONHEAD-513103 MLS

Just 300 steps to the beach in North Forest Beach! Welcome to this beautifully rebuilt beach cottage in the highly sought-after North Forest Beach area, just steps from the beach and withing easy walking distance of Coligny Plaza's restaurants, shops and entertainment. The home features 3 bedrooms and 2.5 baths along with a 2 car garage, one half of which has been thoughtfully converted into a comfortable, air-conditioned office. Outside, enjoy a large private swimming pool, surrounded by a fenced backyard and beautiful, easy-care landscaping. Completely rebuilt in 2017, the home offers two inviting outdoor living spaces, one screened porch and a spacious screened lanai - perfect for relaxing after a day at the beach. There is also abundant storage beneath the enclosed areas. The property features a convenient semicircular driveway, plus additional parking along the side of the home, making it idea for family, friends, and guests. For years, the owners successfully rented the home for approximately 10 peak-season weeks, and it consistently attracted repeated visitors and stayed booked. Location on popular Jacana Street, this home offers an exceptional combination of beach access, privacy, outdoor living, and convenience. Whether you're looking for a personal beach retreat, an investment property, or both, this North Forest Beach cottage is ready to enjoy.

145 Jacana Street, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$4,395,000

3 Beds ⋅ 4 Baths ⋅ 3,591 SqFt. ⋅ HILTONHEAD-512983 MLS

A rare deep-water offering in Spanish Wells, set on an extraordinary 1.21-acre homesite with a private dock, heated pool, oversized two car garage, sweeping water views and spectacular sunrises. Designed for predominantly one-level living, this open floor plan home features a fully updated kitchen with water views, 3 bedrooms, 3.5 gorgeous baths, a private den and light-filled living spaces that embrace the waterfront setting. An exceptional feature is the 2,500+ sq. ft. full basement-a true rarity on Hilton Head Island-offering tremendous flexibility for recreation, workshop, fitness, hobbies or future customization. Outside, enjoy the expansive porch with retractable screens along the rear of the main home, relax on the private porch off the master bedroom, lounge by the pool or step onto your private dock and experience the Lowcountry from the water. Deep-water frontage, substantial acreage, a private dock with 24/7 water access, heated pool, gorgeous sunrise views and an extraordinary amount of additional space combine to create one of Spanish Wells' most distinctive waterfront offerings.

10 Widewater Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$1,475,000

3 Beds ⋅ 4 Baths ⋅ 2,584 SqFt. ⋅ HILTONHEAD-513048 MLS

Walk to the Beach in Palmetto Dunes! Located in the highly desirable, gated Palmetto Dunes oceanfront community, this single-level coastal home is priced for you to add your cosmetic touches. With 3 bedrooms and 3.5 baths, the home features separate living areas, a large kitchen, a fireplace, and vaulted ceilings that create an open feel throughout. Enjoy outdoor living in the beautiful backyard with serene water views and a private pool, perfect for relaxing after a day at the beach. Outdoor shower and 1/2 bath outside. The home is fully furnished and offers you a rare chance to customize a home in one of Hilton Head Island's most sought-after beachfront communities. Just a short walk to the Atlantic Ocean, golf, tennis, and all Palmetto Dunes amenities.

10 Off Shore, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$5,250,000

5 Beds ⋅ 6 Baths ⋅ 4,698 SqFt. ⋅ HILTONHEAD-513037 MLS

The perfect amalgam of luxury and privacy, 124 South Shore Drive represents a truly rare oceanfront offering on Hilton Head Island. This four bedroom, four bathroom townhome property showcases exceptional craftsmanship and construction quality throughout. The living area's two-story ceilings capture natural lighting as it shines off the Atlantic Ocean, while the chef's kitchen features the culinary offerings of Sub-Zero and Wolf appliances. Awaken to your beach landscape from the first floor owner's suite, complete with spa bathroom and substantial oceanfront terrace. Family and visitors will delight in the ample en-suite guest rooms and large second floor media room space. A bonus third floor office, flex room offers additional convenience to both owners and guests. A private residential elevator services the entirety of the space. The home's whole bottom floor has been re-imagined by the current owner to create an oasis of private recreation and leisure. A collector's garage showcases a hardwood ceiling and led lighting, leading to a professional grade gym capable of multiple fitness stations. The climate controlled workshop and storage room showcase a commercial grade dehumidifier, custom shelving and access to the property's telecommunications hub. Begin your beach days from the owner's private oceanfront pathway and eventually unwind by the home's pool and spa, complete with cabana-style bathroom. Exceptional upgrades such as twenty-year warranty exterior paint, geothermal HVACs and dual 85 gallon heat pumps ensure lasting quality and comfort. This exceptional real estate offering is located within the private gates of Leamington, restricting any short-term vacation rentals. Additional offerings include an owners only beach pavilion, community pool, day dock on the 11 mile lagoon system and multiple golf courses, all nestled on the southern shores of Hilton Head Island.

124 S Shore Drive Unit 124, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

$2,875,000

5 Beds ⋅ 5 Baths ⋅ 3,376 SqFt. ⋅ HILTONHEAD-512720 MLS

Welcome to 11 Gunnery Lane, a beautifully updated and exceptionally spacious 5-bedroom, 4.5-bath Sea Pines residence offering style, comfort, and versatility in a peaceful lagoon setting. Ideal for use as a primary or second home, or as a top tier vacation rental with with established history. Filled with natural light, the home features multiple living and gathering spaces and an easy floor plan equally suited to a primary residence, second home, or vacation property. The main level centers around a bright, open kitchen and living area, complemented by a fabulous bar with wine refrigerator and ice maker-perfect for entertaining. A generous primary suite (with steam shower) plus an additional ensuite guest bedroom provide desirable first-floor accommodations. Upstairs, a second primary suite and flexible family and guest spaces offer exceptional privacy and room for family and friends. Outside, enjoy a private pool and spacious deck overlooking the tranquil lagoon and mature Lowcountry landscape. Direct access to the Sea Pines leisure trail makes exploring the resort by bike or on foot effortless, while the beach is approximately a 10-minute walk away. Additional features include multiple living areas, dedicated office/work space with lagoon views, game and media spaces, full laundry room, two-car garage, abundant storage, and generous parking. Beautifully maintained, thoughtfully updated, and ideally located, 11 Gunnery Lane offers a wonderful combination of space, privacy, proximity to the beach, and effortless Sea Pines living.

11 Gunnery Lane, Hilton Head Island

Listing courtesy of BESTNEST By Beverly Serral.

$2,975,000

4 Beds ⋅ 6 Baths ⋅ 4,800 SqFt. ⋅ HILTONHEAD-512978 MLS

Refined elegance intersects with meticulous craftsmanship in this custom residence designed by renowned Hilton Head Island architect Neil Gordon. Completed in 2024, this 4,800+ sq.ft. home is located in the exclusive and luxurious Spanish Wells community. Upon entering, a grand foyer with 20-foot ceilings transitions into a sprawling, 65-foot open-concept living area. Engineered hardwood floors, shiplap walls, and vaulted shiplap ceilings with exposed beams carry throughout the main floor. The living room anchors the space with a striking black porcelain-tiled fireplace wall and expansive Marvin impact-rated windows and doors. The large dining hall flows seamlessly into the oversized gourmet kitchen. Culinary enthusiasts will appreciate the quartzite perimeters, large center island with black granite, and premium Sub-Zero and Wolf appliances, all illuminated by a cupola skylight. An adjacent wet bar includes a Sub-Zero wine fridge, ice maker, and Miele coffee maker. The primary suite offers a private retreat on the main level, featuring a vaulted ceiling, direct terrace access, and a spa-grade en-suite bathroom equipped with floor warming, dual vanities, a doorless walk-in shower, and a deep Victoria & Albert soaking tub. The main level also hosts a guest suite, a dedicated home office with bespoke cabinetry, a powder room, and an art gallery/hall with specialized lighting. Upstairs, you will find a bunk room with four twin berths, a fourth bedroom/library with a Murphy bed plus private bathroom, and a spacious bonus room located above the three-car garage. Outdoor living is equally inviting and elegant, with a screened porch that transitions to a vast shell stone deck. The fully landscaped 1-acre lot centers around a sleek rectangular pool with a waterfall feature, accompanied by a covered outdoor kitchen pavilion and dining island and pool bathroom. We invite you to schedule a private showing to experience this truly exceptional property firsthand.

69 Widewater Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$1,378,000

3 Beds ⋅ 4 Baths ⋅ 2,544 SqFt. ⋅ HILTONHEAD-512828 MLS

Welcome to luxury coastal living in the gated Oakview community off Spanish Wells Road. Featuring spectacular, unobstructed views of the tidal marsh and Intracoastal Waterway, this custom-built 3-bedroom, 3.5-bath home showcases over $225,000 in recent indoor and outdoor upgrades. Main Living & Chef's Kitchen Upgraded Interiors: Newly installed luxury plank flooring throughout the main level and an open-concept living room centered around a cozy gas-log marble fireplace. Gourmet Kitchen: Features sleek new shaker cabinets, premium quartz countertops, a dedicated wine bar, and high-end appliances-including a Wolf induction cooktop, wall oven, and microwave, paired with a Thermador refrigerator. Flex Space: A versatile main-floor room with deck access and an adjoining full bath, ideal as an office or additional guest suite. Owner's Sanctuary & Upper-Level Primary Suite: A massive retreat featuring large picture windows, a private Trex deck with sweeping marsh views, two expansive walk-in closets, and an oversized adjacent laundry room. En-Suite Spa Bath: Includes a double vanity, deep soaking tub, custom-tiled walk-in shower, and refined finishes. Guest Suite: Spacious secondary bedroom complete with its own walk-in closet and breathtaking marsh views. Resort-Style Outdoor Oasis Upper Deck: Features a weatherproofed Trex balcony designed to keep the lower living space completely dry. Brand-New Lower Level Patio & Pool: A custom-built Ramon pool, a fully fenced yard, and an expansive stone patio complete with a firepit, outdoor shower, half bath, and outdoor kitchen featuring a gas grill. Lower-Level Storage & Bonus Room: Includes a 2-car garage alongside a climate-controlled flex room perfect for a gym, workshop, or additional storage. This property seamlessly blends high-end modern updates with tranquil, picture-perfect island scenery. The tidal marsh is perfect for kayaking or paddle boarding. Membership available at Spanish Wells Club for golf, tennis, and pickleball.

35 Silver Oak Drive, Hilton Head Island

Listing courtesy of Beechee Coastal Properties, LLC.

$1,499,900

3 Beds ⋅ 3 Baths ⋅ 2,431 SqFt. ⋅ HILTONHEAD-512571 MLS

Located within the coveted Heritage Woods neighborhood of Sea Pines Resort, this classic three bedroom, three bath home represents a dynamic real estate opportunity. This single floor property boasts dual living areas, large bedrooms and peaceful reading and relaxation nooks. A flexible room on the home's opposite side offers a rare fourth sleeping space or quiet office - complete with a full bath. The home's private swimming pool is framed by Brazilian hardwood decking and wrap-around rear fencing ensures upmost privacy for family and guests. The spacious floor plan offers modern functionality while enduring touches such as the brick fireplace and built in bookshelves lend a timeless charm. Hilton Head Island's award wining beaches are within near distance via Sea Pines' convenient beach paths while the leisurely pursuits of Harbour Town and South Beach are within a short biking distance. This fully furnished home is currently on the short term rental market and represents a turnkey opportunity for a buyer seeking an immediate investment or a ready canvas to create their own island escape.

8 Old Military Road, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 2,672 SqFt. ⋅ HILTONHEAD-512804 MLS

Discover the outdoor lifestyle that draws so many to Hilton Head at 56 Sussex Lane, where privacy, tranquility, and resort-style living come together. Enjoy your own private pool and spa, along with a spacious screened-in porch overlooking a beautiful long lagoon view--the perfect setting for relaxing, entertaining, and enjoying the Lowcountry lifestyle. Tucked away on a quiet cul-de-sac in Indigo Run, one of Hilton Head Island's most sought-after communities, this meticulously maintained home offers a wonderful combination of privacy and convenience. The spacious four-bedroom, three-and-a-half-bath home has a dedicated office and features high ceilings and an inviting great room that opens directly to the screened-in porch. The well-appointed kitchen flows seamlessly into a comfortable family room, with easy access to the new, high-end heated pool and spa and outdoor living areas. Used as a second home by its owners, 56 Sussex is truly move-in ready and a "must-see." With shopping just five minutes away and the beach approximately ten minutes from your door, this home makes it easy to enjoy everything Hilton Head has to offer.

56 Sussex Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,200,000

4 Beds ⋅ 3 Baths ⋅ 2,484 SqFt. ⋅ HILTONHEAD-512850 MLS

Beautifully renovated and fully updated 4 bed/3 bath home just minutes from the beach! This stunning property has been thoughtfully transformed from top to bottom, offering stylish finishes, modern upgrades, and all new furnishings inside and out. The freshly painted interior features new doors & hardware, ceiling fans, lighting, and fixtures throughout. The completely renovated kitchen showcases new cabinetry and appliances, while all three bathrooms have been beautifully updated, including a reconfigured primary bath designed for improved functionality and style. Major improvements include new plumbing, ductwork, roof, and gutter systems, providing peace of mind for years to come. Outside, enjoy a serene private pool area overlooking a lagoon, with updated landscaping and pool surrounds creating the perfect setting for relaxing or entertaining. With its exceptional location near the beach and extensive renovations inside and out, this turnkey home is ready to be enjoyed!

15 Wagon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$2,100,000

4 Beds ⋅ 5 Baths ⋅ 2,256 SqFt. ⋅ HILTONHEAD-512797 MLS

This fully furnished third-row ocean home is ideally located a short distance from the beach via a dedicated path through a winding grove of trees. Situated in the highly sought-after Forest Beach area and conveniently close to the Ocean Gate of Sea Pines Resort. It is perfectly suited for vacation getaways, a second home, or investment rental. With 4 bedrooms and 4.5 baths, this home features welcoming front porches on both the first and second floors, plus two side porches, including a screened porch for relaxing outdoors. You enter the home into a separate first floor living space with a sitting room, TV, a wet bar and refrigerator. This provides a unique area for the guests to separate from the main kitchen, dining and living room, making it easy for all to enjoy their own space. You then enter into the open concept main living area. You have a modern kitchen, counter barstools, a large dining room table, and a big living room with TV plus a small game table. The laundry room and half bath are also located on the main level. All four bedrooms are on the second level, offering access to wide porches-perfect for enjoying the coastal breeze and lush surroundings. After a day at the beach, retreat to the private, fenced side yard featuring a pool, spa, and spacious patio area, ideal for afternoon swims and cookouts. This Forest Beach gem captures the best of the Hilton Head Island lifestyle with exceptional flexibility and appeal.

6 Cassina Lane, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$4,795,000

4 Beds ⋅ 5 Baths ⋅ 4,386 SqFt. ⋅ HILTONHEAD-512195 MLS

Oceanfront Living, Elevated. Set directly along the Atlantic Ocean within Leamington, Palmetto Dunes, 136 South Shore Drive offers an exceptional combination of oceanfront living, privacy, and refined coastal comfort. Tasteful interiors and a spacious floor plan create an inviting setting for both everyday living and entertaining. Just beyond the residence, owners can enjoy the beach, pool, and the natural beauty of Hilton Head Island's coastline. South Shore's intimate setting provides a distinctive advantage. With no short-term rentals, the community maintains a quieter, more private residential atmosphere while remaining conveniently close to the golf, tennis, pickleball, dining, biking, and recreational amenities of Palmetto Dunes.136 South Shore Drive is a rare opportunity to enjoy a beautiful oceanfront residence in one of Hilton Head Island's most desirable and private coastal settings.

136 S Shore Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

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