Hilton Head Island Homes with Guard Amenities

Welcome to Hilton Head Island, South Carolina, a picturesque paradise nestled in Beaufort County, renowned for its stunning coastal beauty and vibrant lifestyle. This enchanting island is not just a destination; it’s a way of life. With its pristine beaches, world-class golf courses, and lush, natural landscapes, Hilton Head Island offers a unique blend of relaxation and adventure that attracts residents and visitors alike.

One of the standout features of this charming locale is its array of homes equipped with guard amenities, ensuring that residents enjoy a secure and tranquil living environment. These exclusive communities provide a sense of safety and peace of mind, allowing you to fully embrace the island’s laid-back lifestyle. Imagine waking up to the sound of waves and knowing that your home is nestled within a community that prioritizes your comfort and security.

Beyond the gates of these guarded neighborhoods, Hilton Head Island boasts a wealth of recreational opportunities. Explore the miles of bike paths that wind through the island, indulge in fresh seafood at local eateries, or take a leisurely stroll along the sandy shores. The island is also home to a vibrant arts scene, with galleries and live performances that showcase local talent.

Whether you’re looking for a permanent residence or a vacation getaway, Hilton Head Island offers homes that cater to every lifestyle and preference. Experience the perfect blend of luxury, comfort, and security in this coastal gem. Your dream home awaits in Hilton Head Island, where every day feels like a vacation!

Newest Hilton Head Island Homes with Guard Amenities

$779,000

4 Beds ⋅ 3 Baths ⋅ 2,000 SqFt. ⋅ HILTONHEAD-511026 MLS

Updated 4 BR, 3 BA home overlooking scenic Henri's Pond in the gated community of Moss Creek. July 2026 - freshly painted throughout with popcorn ceiling removed and LVP installed in first floor halls, dining room, kitchen, living room and primary bedroom. A highlight of the home is the new large screened-in back porch overlooking Henri's Pond, creating the perfect setting for morning coffee, outdoor dining, or relaxing while enjoying the ever-changing views of the water and surrounding wildlife. The current owner further enhanced the property with a spacious 1-car garage and attached carport, providing exceptional convenience and additional storage. Owner had paver driveway and walkway installed from the street to the front door as well as outdoor decking area facing Henri's Pond. Conveniently located near Bostwick Park, featuring 2 pools, fitness center, and deep-water marina. Moss Creek amenities include 2 private 18-hole golf courses, tennis and pickleball courts, dog park, and nature trails. Move-in ready and ideally suited for enjoying the Lowcountry lifestyle. All major home items - roof, new HVAC and ductwork, PEX piping - recently updated.

283 Moss Creek Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$250,000

2 Beds ⋅ 2 Baths ⋅ 950 SqFt. ⋅ HILTONHEAD-511784 MLS

Step inside this bright and welcoming coastal condo, where one of Hilton Head Resort's LARGER FLOOR PLANS creates a noticeable sense of openness, comfort, and flexibility... The spacious living room, dining area, and kitchen flow together naturally, making the condo feel inviting from the moment you enter and providing plenty of room to unwind after a day at the beach, gather for meals, or entertain family and friends... Warm wood-look flooring, crown molding, soft neutral finishes, and comfortable furnishings give the main living space a relaxed coastal feel, while the kitchen features crisp white cabinetry, GRANITE counters, a double-basin sink, generous prep space, and a convenient pass-through that keeps the kitchen connected to the living area... Both bedrooms are comfortably sized, including a versatile guest room thoughtfully arranged with space for a full-size bed and bunk beds, allowing the condo to accommodate additional guests without sacrificing comfort... The bathrooms have been nicely updated with modern vanities, contemporary fixtures, marble-look tile flooring, and a beautifully tiled walk-in shower with sliding glass doors... One of the most valuable features of this larger layout is the WASHER AND DRYER INSIDE THE CONDO, offering a level of convenience that is especially appealing for full-time living, extended vacations, and short-term rental guests... Additional storage makes it easy to keep beach chairs, luggage, and everyday essentials neatly organized... Offered FULLY FURNISHED and ready to enjoy, this well-maintained villa is located in the preferred Tennis Building #4 with convenient ELEVATOR ACCESS... Hilton Head Resort offers the kind of amenities that make every visit feel like a true coastal escape, including direct beach access by private boardwalk or seasonal shuttle, indoor and outdoor pools, a heated indoor pool, kiddie pool, hot tub, sauna, fitness center, indoor jogging track, lighted tennis and pickleball courts, volleyball, bike rentals and storage, grilling stations, sun decks, garden areas, a deli, and the iconic Coco's on the Beach... Centrally located mid-island near Palmetto Dunes, Shelter Cove Marina and Towne Centre, golf, bike paths, shopping, dining, and entertainment, this condo is an excellent choice as a primary residence, beach getaway, or RENTAL-READY investment property.

663 William Hilton Parkway Unit 4135, Hilton Head Island

Listing courtesy of Real Broker, LLC.

$1,995,000

2 Beds ⋅ 2 Baths ⋅ 1,883 SqFt. ⋅ HILTONHEAD-511684 MLS

Selling a dream located 4th row on Whistling Swan to build your new custom home! Steps away from SP Beach Club restaurants, beach bar and the sandy white beach and Plantation Golf Club. Lot dimensions are 107 X 133 X 103 X 150 = .34/acre. Selling "As- Is"; "Where-Is" with seller making no repairs. No inspections. Possible lease back needed.

1 Whistling Swan Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC.

$650,000

4 Beds ⋅ 3 Baths ⋅ 1,840 SqFt. ⋅ HILTONHEAD-511832 MLS

Welcome to this charming Charleston-style 4-bedroom, 2.5-bath home situated on a large corner lot in the desirable gated community of Victoria Square on Hilton Head Island. Designed for relaxed coastal living, this home offers an abundance of outdoor living spaces, including a cozy front porch, a screened patio on the first floor, an oversized screened porch off the living room, and a spacious open balcony off the primary suite on the top floor-perfect for soaking up the sunshine or enjoying peaceful evenings. The beautifully renovated kitchen features new appliances, full-height cabinetry, granite countertops with a matching backsplash, and tile flooring. The spacious living room is highlighted by a cozy fireplace, creating a warm and inviting gathering space. Upstairs, you'll find new luxury vinyl plank flooring throughout all bedrooms. Enjoy peace of mind with numerous recent upgrades, including a newer roof, gutters, French drain, ductwork, HVAC systems, and water heater. The private backyard has been enhanced with new landscaping, creating a tranquil outdoor retreat. Additional features include a two-car garage and an extended driveway for ample parking. Ideally located in the heart of Hilton Head Island, this home is just a short bike ride to the beach, parks, shopping, and restaurants. Victoria Square offers low HOA dues and outstanding amenities, including a community pool, playground, leisure trails, 2 acre lagoon, a security gate, and boat and RV storage, making it the perfect place to enjoy the Lowcountry lifestyle.

10 Victoria Square Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$1,500,000

5 Beds ⋅ 5 Baths ⋅ 3,032 SqFt. ⋅ HILTONHEAD-510354 MLS

Built in 2017 and expertly maintained, this 5-bed, 4.5-bath, lagoon-front home in gated Sandcastles by the Sea is one of Folly Field's most compelling turnkey investment opportunities. Offered fully furnished, with future bookings transferring at closing, this home is ready to perform from day one. Four levels of well-appointed living space accommodate up to 14 guests, anchored by two king primary suites, an open-concept main level, a loft lounge, and a top-floor suite designed for maximum occupancy. Every level opens to covered deck space with serene lagoon views, a consistent driver of repeat bookings. The private heated pool and gated community setting complete a package that guests and owners alike return to season after season. Folly Field Beach is just steps away, accessible by foot, bike, or golf cart in minutes. This level of beach access continues to drive strong guest demand and supports premium rental rates year after year. As a newer home with a well-documented history of expert care, this property offers something increasingly rare in the short-term rental market: true confidence in condition. Minimal maintenance and years of reliable operation ahead mean a buyer can close and focus on the return, not the upkeep.

64 Sandcastle Court, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$1,849,500

3 Beds ⋅ 3 Baths ⋅ 2,440 SqFt. ⋅ HILTONHEAD-511596 MLS

Classic Hilton Head Island architecture, perfectly preserved and completely reimagined. Set on a rare corner estate lot of more than three-quarters of an acre in Shipyard Plantation, 37 Kingston Road offers a level of finish and scale rarely found at this price point among the Island's premier gated communities. A complete renovation from top to bottom includes brand new HVAC systems with all new ductwork, a stunning new pool with a Pennsylvania flagstone deck, and designer finishes throughout. Vaulted ceilings, skylights, and thoughtful millwork bring warmth, character, and natural light to every room. The kitchen has been completely updated with white shaker cabinetry, stone countertops, stainless steel appliances, and a center island. The split floor plan offers ideal separation between the primary suite and guest bedrooms, while the generous lot provides the opportunity to add a guest house or casita. The primary suite is spacious and serene, with direct access to the pool and a beautifully renovated bath featuring a marble walk-in shower and double vanity. Every bathroom reflects the same level of craftsmanship and attention to detail found throughout the home. Outside, the new pool and Pennsylvania flagstone deck create a private outdoor retreat surrounded by mature live oaks and classic Lowcountry landscaping. The bonus Carolina room extends the living space, creating a seamless connection between the home's interior and outdoor living areas. Offered furnished and available for immediate enjoyment, the home is just a five-minute bike ride to the Shipyard Beach Club and the Sonesta Resort, and only minutes from some of the Island's best dining, shopping, golf, and recreation. Short-term rental projections are available upon request. Whether the goal is a primary residence, a multigenerational retreat, a second home, or an income-producing investment property, 37 Kingston Road is uniquely positioned to deliver. A rare corner estate, completely renovated, furnished, and ready, at a price that rewards the discerning buyer who knows this market. *Owner is SCREA.

37 Kingston Road, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty.

$550,000

2 Beds ⋅ 3 Baths ⋅ 1,440 SqFt. ⋅ HILTONHEAD-511566 MLS

Well-appointed 2-bedroom, 2.5-bath townhome offering two private bedroom suites, a spacious great room, dining area, and updated kitchen w/ breakfast area. The main floor has a flex room which can be used as an extra bedroom, den, or office. On the upper level, you have the same flex room off the primary bedroom - a great nursery, office, or den area. You will love the outside areas- a quaint space off the breakfast room for morning coffee and a very large deck off the back for weekend barbeques. Upgraded features include an updated KT, LVP flooring, smooth ceilings, fresh paint inside, a new shower in the primary bathroom, and it comes fully furnished. Lives like a home as you have no one above or below you. This is a pet-friendly villa (for owners) that is nestled within the gated Shipyard community; residents and guests enjoy beach access, championship golf, walking and biking trails, and a prime mid-island location. The new Shipyard Beach House has extra storage for all your beach gear. The front entrance is convenient to shopping and dining, while the back gate is close to Coligny and Celebration Park. You can't beat the location. Come and take a look today- you will not be disappointed.

90 Gloucester Road Unit 203, Hilton Head Island

Listing courtesy of Charter One Realty.

$595,000

2 Beds ⋅ 2 Baths ⋅ 1,513 SqFt. ⋅ HILTONHEAD-511622 MLS

ATTENTION: The most desirable plan in The Preserve...the Palmetto! Complete with TWO PRIVATE GARAGES, both offering direct access to the villa. Single-story living with NO STAIRS and convenient access through the rear gate! This highly sought-after floor plan offers spacious, comfortable living with stylish, low-maintenance flooring (tile and LVP). The kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and a convenient pantry. Smooth ceilings, generously sized rooms, and awesome closet space add to the overall appeal. Both garage floors have been newly finished with a high-performance epoxy finish that carries a lifetime warranty. The HVAC system features a newly installed UV system designed to help reduce mold, pollen, and other airborne contaminants within the system and ductwork. Enjoy tranquil wooded views from the private screened porch. Immaculate condition, exceptional storage, two garages, and impressive amenities-including a pool, fitness center, pickleball and tennis courts, garden-style grounds, and gated entry-make this villa a rare find!

4 Indigo Run Drive Unit 4121, Hilton Head Island

Listing courtesy of Collins Group Realty.

$1,150,000

3 Beds ⋅ 5 Baths ⋅ 3,250 SqFt. ⋅ HILTONHEAD-511807 MLS

Excellent value on updated, superbly maintained lifestyle home with private pool/spa and panoramic lagoon views on quiet cul de sac street in popular Hilton Head Plantation. Features include soaring, smooth vaulted & tray ceilings, wood & tile flooring, granite & composite counters, high end appliances (Forno 8 burner gas range & double Ovens, etc.), custom cabinetry/vanities/built-ins, plantation shutters, skylights, recessed lighting, ceiling fans, walls of windows to pool & lagoon views, 17 SEER high efficiency HVAC system, newer roof (2022) & mechanicals, etc. Very livable floor plan offers Chef's dream kitchen (large island, coffee/wet bar, butlers pantry, max cabinet & counter space), open to casual and formal dining, expansive great room, bonus/media room, much desired screened porch, 3 BR suites including well-appointed primary suite w/private courtyard, 2 ample guest BR's with updated baths (glass & tile surround showers, new vanities, counters, lighting), secluded den/study, 2 powder rooms, 2nd floor loft, walk-in attic space, 2 car garage and ample closet/storage space. All with charming curb appeal, circular drive, specimen live oaks, palms, azaleas, etc. and proximity to Crooked Pond Pool/Tennis, front gate & shopping/dining/entertainment + HHP's Spring Lake Pool Complex, Dolphin Head Recreational Area and newly refurbished Pine Island Beach Park!

3 Twisted Cay Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 2,205 SqFt. ⋅ HILTONHEAD-511804 MLS

Experience the very best of Sea Pines from this beautifully updated Fairway Oaks villa. Privately situated at the end of a quiet cul-de-sac, this 2,200-square-foot home offers a rare combination of privacy, natural beauty, and convenience-with an attached two-car garage, an uncommon and highly sought-after feature in Sea Pines villas. The home features 3 bedrooms and 2 full and 1 half bath including a spacious first-floor primary suite featuring soaring ceilings, an oversized custom walk-in closet, a luxurious steam shower, heated towel rack, and spa-inspired finishes. Upstairs, two generously sized guest bedrooms and a full bath create an inviting retreat for family and friends.The beautifully renovated kitchen showcases granite and quartz countertops, custom floor-to-ceiling cabinetry, new appliances, and a beverage center with wine cooler and kegerator. Walls of windows fill the living areas with natural light and frame peaceful lagoon views. Step onto the expansive rear decks, where a charming water feature creates a serene setting beneath the towering evergreens..Fairway Oaks is one of Sea Pines' most desirable villa communities, uniquely surrounded by tranquil lagoons and the scenic fairways of Heron Point Golf Course. Residents enjoy a private swimming pool, tennis and pickleball courts, and the peace of mind that comes with no short-term rentals allowed. Just a short walk or bike ride from Harbour Town's iconic lighthouse, marina, waterfront dining, boutique shopping, and miles of scenic trails, this exceptional villa offers the very best of the Lowcountry lifestyle. Whether you are searching for a full-time residence or an elegant coastal getaway, this is more than a home--- It is the lifestyle you have been waiting for. OSCREA

40 Planters Wood Drive Unit 2516, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$900

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511802 MLS

Own Your Spring Escape at Swallowtail in Sea Pines - Week 13! Seize the opportunity to own deeded Week 13 in the heart of Hilton Head Island's premier Sea Pines community. This stunning Swallowtail property, situated along the 12th fairway of the Heron Point Golf Course, offers the perfect blend of golf course tranquility and coastal adventure. Positioned between Harbour Town's iconic lighthouse and the Beach Club's sun-kissed shores, Swallowtail offers easy access to championship golf, pristine beaches, waterfront dining, and luxury boutiques. Whether you're spending your mornings on the green, afternoons lounging on the beach, or evenings exploring the charming Harbour Town, Swallowtail offers the low-maintenance luxury lifestyle you've been dreaming of. Don't miss the chance to make this slice of paradise yours - secure your Week 13 getaway today!

70 Lighthouse Road Unit 2890, Hilton Head Island

Listing courtesy of Lighthouse Realty.

$1,500

2 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511798 MLS

Owner is also selling Week 18 (Unit 2875) and is open to offering a discounted price if both weeks are purchased together-an excellent opportunity to enjoy two consecutive weeks in paradise! Enjoy the relaxed sophistication of Hilton Head Island during deeded Week 17, ideally positioned in the first week of May when the island is at its springtime best. Swallowtail at Sea Pines offers a refined, low-maintenance vacation experience in one of the island's most sought-after settings. This desirable villa overlooks a lush lagoon, providing peaceful views and a tranquil backdrop throughout your stay. Ideally situated between Harbour Town Lighthouse and the sun-soaked Beach Club, you're just a short stroll from championship golf courses, pristine beaches, waterfront dining, and a vibrant coastal arts and culture scene. Imagine beginning your mornings with refreshing ocean breezes and serene golf course vistas, then setting out to bike beneath towering live oaks along miles of shaded pathways. Spend your afternoons on award-winning fairways, relaxing on the beach, or exploring the island's natural beauty before unwinding with spectacular waterfront sunsets. May's comfortable temperatures and blooming landscapes create the perfect setting for beach walks, outdoor dining, dolphin cruises, and all that Sea Pines has to offer-without the crowds of peak summer. Whether you prefer championship golf, coastal adventures, or simply relaxing on your private balcony overlooking the greens, everything you need is right at your doorstep. With the option to purchase the adjoining Week 18 at a discounted package price, this is a rare opportunity to enjoy two consecutive weeks in one of Hilton Head Island's premier vacation destinations.

70 Lighthouse Road Unit 2874, Hilton Head Island

Listing courtesy of Lighthouse Realty.

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