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

$1,049,000

4 Beds ⋅ 4 Baths ⋅ 3,095 SqFt. ⋅ HILTONHEAD-511560 MLS

Wonderfully set along a quiet, residential cul-de-sac, nicely buffered for privacy, and featuring distant golf views. Palmetto Hall is one of Hilton Head Island's most established and inviting residential communities, and this is the first time this beautiful (3,095sqft) home has ever been made available for sale. It is perfectly situated on a full-size homesite with additional outdoor living areas and open space to the South and West. And while this is a predominantly single-story home, a versatile upstairs bonus suite offers added flexibility, as a home office or a 4th bedroom suite. The spacious kitchen includes stainless steel appliances, a pantry, and an open connection to the family room! Plus, tall (smooth-finished) ceilings and a fireplace help create a comfortable and relaxing feel. Additional highlights include plantation shutters and an elegant living room with a double-tray ceiling. The screened porch, constructed in 2011, has been a well-enjoyed feature of this home for years, and truly extends the living space outdoors (and we all know the weather here is awesome nearly year-round!) Additionally, the backyard patio creates an ideal place outside to embrace the quiet backyard setting and/or entertain friends and neighbors! All this plus a multi-zone HVAC, a new roof in 2023, and a new water heater (to be installed in 2026) come together nicely to add valuable peace of mind.

7 Lenox Lane, Hilton Head Island

Listing courtesy of Collins Group Realty.

$950,000

3 Beds ⋅ 2 Baths ⋅ 2,629 SqFt. ⋅ HILTONHEAD-511543 MLS

Tucked away on a quiet cul-de-sac in the desirable Big Woods neighborhood of Hilton Head Plantation, this beautifully renovated 3 BR, 2 BA home offers spacious, single-level living with a flexible floor plan designed for everyday comfort and entertaining.The home underwent a comprehensive, top-to-bottom renovation in 2016, with finishes, fixtures, & major components replaced or updated throughout. The formal living room features a striking brick fireplace, impressive tall ceilings & a beautiful wood beam that adds warmth & architectural character. The open kitchen includes an eat-in area with a bay window and opens to a spacious family room featuring a second fireplace & elegant tray ceilings. Smooth ceilings throughout contribute to the home's clean, updated appearance.A large formal dining room with a bay window & a bright Carolina room provide additional spaces for entertaining, relaxing, working from home, or enjoying a quiet morning with a cup of coffee. The generously sized primary suite features its own bay window, a spacious walk-in closet, and master bath with a soaking tub plus large separate shower.Additional highlights include impact windows throughout, a 2-car garage, abundant living space & a large, private backyard with plenty of room to create an outdoor entertaining area or add a swimming pool.Hilton Head Plantation offers an exceptional Lowcountry lifestyle and an impressive collection of recreational amenities. At Spring Lake, residents enjoy a resort-style pool with zero-entry access, a lazy river, splash areas, and lap lanes, along with nearby tennis & pickleball facilities. Dolphin Head Recreation Park provides a beautiful waterfront setting along Port Royal Sound, while the restored Pine Island shoreline offers an expansive beach area that is perfect for walking the dog, watching the sunset, or settling in with a good book.Hilton Head Plantation can enjoy access to Sea Pines Resort with their property owner decal making it easy to visit Harbour Town and its popular shops, restaurants, & public attractions.The home is conveniently located near Hilton Head Plantation's front gate, providing easy access to grocery stores, shopping, dining, & everyday conveniences.This special home combines a peaceful cul-de-sac setting, extensive renovations, distinctive architectural details, flexible living spaces, outstanding community amenities, & a convenient north end location with easy beach access to the Islander or Coligny Beaches.

6 Horseman Lane, Hilton Head Island

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

$999,000

4 Beds ⋅ 4 Baths ⋅ 3,567 SqFt. ⋅ HILTONHEAD-511502 MLS

This wonderful family home offers an abundance of space tailored to meet every modern need. Featuring 4 bedrooms, 3.5 baths, a private office, a sun-drenched Carolina room, and a versatile loft, this property is designed for both comfort and functionality. As you enter, you are greeted by a beautiful grand staircase and an open concept with vaulted and tray ceilings throughout the main living areas. Other features include a large eat-in kitchen with stainless appliances, solid surface flooring, wainscoting panels, gas fireplace, 2-car garage and golf-cart bay, covered front porch, back deck, firepit, and views of the 11th hole of the Hills course. This property provides the perfect framework for a vibrant family lifestyle, combining an exceptional design with highly functional living spaces. Residents of Palmetto Hall enjoy 2 championship golf courses, tennis/pickleball courts, a swimming pool, and a beautiful southern styled clubhouse offering dining and social events. Seller is offering a $15,000 painting credit at closing. Seller is a SC licensed Real Estate Agent.

6 Tucker Ridge Court, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$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 blends timeless design with thoughtful updates, featuring white shaker cabinetry, stone countertops, stainless steel appliances, updated hardware and fixtures, 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.

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