Hilton Head Island Homes with Rain Gutters Exterior Features

Welcome to Hilton Head Island, South Carolina—a stunning coastal paradise nestled in Beaufort County. Renowned for its breathtaking beaches, world-class golf courses, and vibrant wildlife, Hilton Head Island is an enticing destination for both vacationers and those seeking a permanent slice of island life. With its rich history and an array of outdoor activities, this charming island community offers a unique blend of relaxation and adventure.

One of the appealing features of homes in Hilton Head Island is the thoughtful design that includes rain gutters. These exterior features not only enhance the aesthetic appeal of the properties but also provide practical benefits. Rain gutters effectively channel rainwater away from your home’s foundation, protecting it from potential water damage and erosion. This is especially important in a coastal environment like Hilton Head, where heavy rains can occur.

In addition to their functional benefits, homes equipped with rain gutters contribute to the overall durability and maintenance of your property. Whether you’re looking for a cozy beach cottage or a luxurious oceanfront estate, you’ll find that many homes in Hilton Head Island come with this essential feature.

Imagine waking up to the sound of waves crashing and knowing your home is equipped to handle the elements. With its picturesque landscapes, welcoming community, and homes designed for both beauty and resilience, Hilton Head Island is truly a place where you can live your best life. Explore the possibilities of homeownership in this idyllic location today!

Newest Hilton Head Island Homes with Rain Gutters Exterior Features

$649,900

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-511287 MLS

Moss Creek Lifestyle. Move-In Ready. Easy to Love. A rare opportunity to enjoy the Moss Creek lifestyle in a beautifully updated, move-in-ready home that is comfortable, manageable, and easy to love. Located in desirable Royal Pointe, this charming 3-bedroom, 2-bath home offers 1,822 sq. ft. with an open, inviting floor plan and numerous thoughtful improvements throughout. The remodeled kitchen features updated cabinetry, countertops, appliances and finishes and flows effortlessly into the dining and living areas-perfect for everyday living or entertaining. Updated flooring and fresh interior paint give the home a clean, current feel, while the spacious great room, vaulted ceiling and fireplace add warmth and character.The generous primary suite offers excellent closet space and an updated bath, while two additional bedrooms provide flexibility for guests, a home office or hobbies. Outside, enjoy a beautifully refreshed backyard, mature Lowcountry landscaping and private outdoor living space ideal for relaxing or entertaining. A spacious two-car garage provides additional storage and everyday convenience.For buyers looking to downsize, establish a Lowcountry second home or simply enjoy one of the area's most established private communities without taking on an oversized property, this one is especially compelling. Moss Creek offers two golf courses, clubhouse dining, marina and boating amenities, tennis and pickleball, fitness and swimming facilities, nature preserves and miles of leisure trails-all in an incredibly convenient location just before the Hilton Head Island bridge. Updated, well maintained and ready to enjoy from day one, 3 Royal Pointe Drive offers an exceptional combination of lifestyle, location and value.

3 Royal Pointe Drive, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$739,000

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-512194 MLS

One of the only semi-custom floor plans in Old Stoney Village! This 4 bedroom 4.5 bath is full of custom home features including: each bedroom having its own ensuite bath, luxury LED lighted vanity mirrors, dining room bay window, living room built ins, upgraded closet shelving, oversized kitchen island with custom cabinets, full hop up quartz kitchen backsplash, enlarged tile showers, a gas range, dual laundry hookups on both floors, and an additional office/den. This home also features dual primary bedrooms (one on both first and second floor), garage, a grilling deck with propane hook up, front porch and the option to fence in the back yard. Set on a wooded corner lot, located off a quiet cul de sac, making this one of the most private lots in the neighborhood. Old Stoney Village is a pet and golf cart friendly community with a low HOA and close proximity to community waterfront parks, some of the islands best waterfront dining, schools and the Island rec center. Located on the north end of Hilton Head creating easy access to all of Hilton Head and Bluffton.

40 Old Stoney Lane, Hilton Head Island

Listing courtesy of Condomaximum Concepts Inc.

$3,995,000

5 Beds ⋅ 7 Baths ⋅ HILTONHEAD-512060 MLS

Waterfront living in Wexford doesn't get much better than this and 20 Castlebridge Court offers the ONLY harborfront setting currently available in the community. Set directly on the harbor at the end of a private cul-de-sac, this five-bedroom residence combines exceptional outdoor living with one of the neighborhood's most desirable settings. A heated pool and spa, outdoor fire pit, built-in grilling station, and private dock make the most of life on the water. The spacious floor plan features a grand living room upon entry, adjacent dining room, a generous kitchen enhanced by Sub zero and Viking appliances, two stately gas fireplaces, bonus room, bunk room, three-car garage, and dedicated golf cart bay. The quality of construction does not go unnoticed with solid wood doors, plantation shutters, wide-planked hardwood floors, elevated lighting, and built-in features throughout. Then there is Wexford itself. Boasting a newly redesigned clubhouse with indoor/outdoor dining, community pool, exceptional Arnold Palmer Signature golf, active tennis community, pickle ball, a private marina, and the signature lock-controlled 37 acre inland harbour. The community truly is unlike anything else on Hilton Head Island and for someone looking for harborfront living within Wexford, there is only ONE.

20 Castlebridge Court, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$899,000

4 Beds ⋅ 4 Baths ⋅ HILTONHEAD-512036 MLS

This stunning four-bedroom home located on a cul-de-sac street sits on a great lot with views of the Oyster Reef Golf Course. Even better, it's just around the corner from the access point for the Dolphin Head Bluff Path. This home boasts an incredible floor plan with two primary bedroom suites, one downstairs and one upstairs. You will enjoy the renovated kitchen with stainless steel appliances, custom cabinets, all open to the main living areas. There is so much natural light throughout and tons of storage space. This home has beautiful crown moldings and great ceiling height throughout.Living in the Low Country means outdoor living space is a must, and this has an incredible back yard/patio with exceptional golf views of #8 of the Oyster Reef Course. Updated bathrooms recently painted and the roof was replaced a year ago, you can move in worry free. Hilton Head Plantation has low fees and incredible amenities: Golfers have four championship 18-hole courses within the community (Bear Creek, Dolphin Head, Oyster Reef and the Country Club of Hilton Head). Private beach lovers enjoy a private shoreline along the Port Royal Sound in Dolphin Head Park. HHP has a resort-style zero-entry pool with lazy river and splash pad anchors Spring Lake Recreation Area. There's even a Marina just inside the community and for garden lovers, Seabrook Farms is a place where residents can rent beds to grow vegetables, fruits, and flowers.

16 Yellow Rail Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$7,399,500

5 Beds ⋅ 6 Baths ⋅ HILTONHEAD-511871 MLS

Welcome to 34 Ruddy Turnstone - a classic custom-built oceanfront home in Sea Pines designed by renowned Hilton Head architect Jakie Lee. Perfectly positioned on a large private homesite, this timeless residence showcases the charm, craftsmanship, and thoughtful design that define the finest Sea Pines properties. Exceptional quality is evident throughout with wide stairways, custom woodworking, soaring ceilings, and solid-core doors, all blending to create an atmosphere of relaxed yet refined coastal living. Designed for both comfort and entertainment, the home offers generous indoor and outdoor living spaces, including a heated pool and spa surrounded by lush privacy. The second level features the private Primary Suite with a sitting area, a spacious Great Room, Dining Room, and Eat-In Kitchen - all opening to an expansive IPE wood deck with elevated views overlooking the pool and the Atlantic Ocean. The entry level welcomes guests through a covered entrance into a dramatic foyer with high ceilings and access to the large Family Room complete with built-in beverage coolers and bar area. From here, enjoy seamless access to the covered porch, pool/spa and private beach path. Three Guest Bedrooms, each with their own Ensuite Bath, are also located on this level, along with an additional full bath and Laundry Room for added convenience. A fourth Guest Bedroom and full-size private Office with balcony occupy the mid-level, providing additional flexibility for family and guests. A newly installed elevator with service to all four levels, ensuring effortless enjoyment throughout the home. Thoughtfully designed and meticulously maintained by its original owners as a cherished second home, this exceptional oceanfront retreat offers the rare opportunity to enjoy a classic Sea Pines residence exactly as it is today - or reimagine and personalize it over time to create your own coastal legacy.

34 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$850,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512111 MLS

Tucked away on a private cul-de-sac in Hilton Head Plantation, this bright and spacious3BR/3BA home offers single-level living, excellent bedroom separation and a gated courtyard entry. Enjoy views of the 10th hole of Oyster Reef Golf Club from your backyard stone patio, with no homes directly across the street, and walk to Oyster Reef Golf Club and Loggerhead Tavern. The light-filled living room features vaulted ceilings, while the updated eat-in kitchen offers top-of-the-line appliances, stone countertops, bamboo cabinetry, imported tile floors and greenhouse windows for a contemporary feel. A 2+ car garage, updated plumbing and roof less than 10 years old add to the appeal. Hilton Head Plantation amenities include four 18-hole golf courses, a chilled Lazy River and pool, tennis, pickleball, miles of leisure trails and the beautiful recently renourished Dolphin Head Beach. Priced to reflect the opportunity for updates and personalization, this home is ready for you to make it your own and enjoy all Hilton Head has to offer!

14 Oyster Reef Cove, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

$7,800,000

6 Beds ⋅ 8 Baths ⋅ HILTONHEAD-510819 MLS

Experience unparalleled oceanfront luxury in the exclusive, private community of Port Royal on Hilton Head Island. This 6,208-square-foot, two-story coastal home features six bedrooms, five full baths, and three half baths, offering an exceptional blend of timeless architecture. Meticulously enhanced with extensive modern updates, the home welcomes you with a grand foyer, soaring ceilings, and open, light-filled living spaces. Stunning 2-story glass frames sweeping panoramic Atlantic vistas and the maritime landscape from nearly every room. The newly remodeled chef's kitchen is complete with leather-stamped quartz countertops, a premium Sub-Zero refrigerator, a gas Bertazzoni Range, 2 stainless steel sinks, a farmer sink and a customized bar area. A generous island designed for effortless entertaining seats six. Throughout the interior, earth toned tile, stone and wood flooring complement the home's design. The primary suite serves as a serene sanctuary with stunning ocean views and a spa-inspired bathroom while each guest suite ensures ultimate comfort with private en-suites. Notably, three of the six bedrooms boast breathtaking direct ocean views.The luxury extends outdoors to a private beachfront oasis designed for relaxation and entertainment. Expansive patios, second-story veranda balcony, and an oceanside salt water pool offer front-row seats to legendary sunrises, cool sea breezes, and the tranquil lapping of the waves. Enjoy direct, private access to Hilton Head's pristine shoreline right from your backyard. Thoughtfully updated, the property features a durable metal roof, a classic stucco exterior, a spacious three-car garage, newly paved driveway plus paver pathways and refreshed landscaping. Situated on one of Port Royal's private, winding, oak-tree-lined cul-de-sac streets, this gated-community oceanfront residence offers a rare combination of luxury, privacy, and coastal living at its best.

10 Drayton Place, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$739,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511979 MLS

Overlooking the 6th hole of Moss Creek's South Course, this move-in ready 3-bedroom, 2.5-bath home offers the perfect blend of Lowcountry charm, thoughtful design, and effortless living in one of the area's most sought-after communities.Step inside to discover beautiful pine floors, soaring ceilings, and timeless architectural details throughout. Designed for both everyday living and entertaining, the open floor plan features a spacious kitchen that flows seamlessly into the vaulted great room, complete with a cozy fireplace and custom built-ins. A separate dining room with an elegant tray ceiling provides the perfect setting for family dinners and holiday gatherings.The main-level primary suite offers a private retreat with dual walk-in closets and a spacious bath featuring dual vanities, a soaking tub, a beautifully tiled walk-in shower, and a private water closet. Upstairs, two generously sized guest bedrooms, a full bath, and an oversized storage closet provide excellent separation and privacy for family and visitors.Step outside to the private deck and enjoy peaceful golf course views framed by mature landscaping. Additional highlights include a new roof (2026), new carpet (2026), oversized two-car garage, paver driveway and front walkway, laundry room, powder room, and a low-maintenance homesite designed for easy living. Residents of Moss Creek enjoy an exceptional lifestyle with two championship 18-hole golf courses, a deep-water marina, tennis and pickleball courts, fitness center, clubhouse, waterfront pool complex, nature trails, and Mackay's Grill. Offering the convenience of primarily one-level living, quality finishes, and a highly functional floor plan, this home is ideal as a full-time residence or a lock-and-leave Lowcountry retreat.

21 Wax Myrtle Court, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$2,500,000

4 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511633 MLS

Beautiful Ocean Views from Multiple Rooms. This exceptional 3rd-row Port Royal home offers an inviting blend of coastal elegance, spacious living, and an unbeatable location. Soaring ceilings and a thoughtfully designed floor plan create an open, airy atmosphere with excellent separation of living spaces. Features include an eat-in kitchen, spacious family room, formal living and dining rooms, and a conditioned Carolina room for year-round enjoyment.Just steps from the Port Royal Beach Club, oceanfront pool, and beach access, this home offers the convenience of premier community amenities without the maintenance of a private pool. Port Royal is one of Hilton Head Island's most sought-after private oceanfront communities, featuring gated security, beach access, pickleball and tennis courts, and scenic leisure trails and more. Optional membership to the Port Royal Golf Club provides access to championship golf, tennis & dining. To preserve the community's peaceful residential character, short-term rentals are not permitted.

14 Salt Spray Lane, Hilton Head Island

Listing courtesy of Charter One Realty.

$1,300,000

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511956 MLS

First time on the market! Come see this bright, elegant home with high smooth ceilings, skylights, and glass on nearly every wall. This 4 bedroom (or 3-bed + bonus), 3-bath home includes a large bonus room with full bath over the garage that could be the 4th bedroom, or a studio, office, den, lounge, or workout space, along with a 2-car garage & under-house storage. The living room was designed for cozy movie nights & entertaining, with built-ins flanking the never-used wood fireplace. Bull-nosed corners soften the space. Out back is private & protected, with lagoon & Forest Preserve views that mean your morning coffee comes with egrets, herons, and turtles. An easy bike or walk to the restaurants & shops outside the main gate, or ride through the Forest Preserve to the beach, garden, or Harbour Town. Enjoy all the amenities Sea Pines and Carolina Place have to offer. Carolina Place fees include pool, pickleball, tennis, steam room, sauna, lawn & landscape maintenance, pest control, and trash. The owner had this home built & has never rented it, which is easy to see once you walk through the front door. It is spotlessly clean & updated. New roof in 2018. Replaced subflooring in 2020 through much of the main level, topped with 5-inch ebonized oak plank hardwood & a UV sealer coat to protect it. KitchenAid appliances. The primary bath was redone with new flooring, a new shower, and Kohler fixtures & hardware throughout, and the other two baths have new toilets. Both front bedrooms have hurricane-resistant pop-out windows. Gutters & gutter guards in 2020, skylights re-tightened, the entire exterior painted, and about 70 percent of the interior. New garage door system & front door hardware in 2026, along with new upstairs shower fixtures & paint. The HVAC compressor & furnace fan motor were replaced in 2025 on one of the two maintained 2016 systems, and the kitchen faucet & disposal are new as well. Underneath, a vapor barrier & foam insulation were added in 2020, and the perimeter is fenced with secured access gates. Outside, six large trees were cleared to open up the lot, with new sod, fresh landscaping, and a 2021 Rainbird irrigation system. Termite bond has been in place since 2020 with annual inspections & no issues. If you're looking for a home that's ready to move into, this is it. Some photos are virtually staged to show what the space can do. This home would be excellent as a primary, secondary, or rental home. Homes like this do not come up often.

64 Shell Ring Road, Hilton Head Island

Listing courtesy of Southern Lifestyle Properties of SC LLC.

$1,985,000

3 Beds ⋅ 4 Baths ⋅ HILTONHEAD-511813 MLS

An absolute standout in Sea Pines. This exceptional home was worth the wait... but is not expected to last long! Relaxed and comfortable meets modern and sophisticated. Prepare to be captivated by this exceptionally cool, single-level stunner! A private (gated) front courtyard enhances the arrival experience, while the private backyard setting is unmatched. Inside you will find an open-concept interior that is complimented by numerous design enhancements. The design-forward, chef-style kitchen will reignite your love of both cooking and entertaining, boasting quartz counters, impressive cabinetry, designer lighting, updated appliances, gas cooking, beverage refrigerator, pantry, and an expansive flat-top island. The home naturally flows out to an inviting screened porch, extending comfortable living space outdoors. The spacious owner's suite enjoys tranquil water views and a spa-like bath, while the two private guest rooms offer beautifully remodeled en-suite baths as well. Embrace a year-round outside lifestyle with a refreshing (heated) saltwater pool, firepit area, peaceful lagoon and private backyard lawn. The property features a durable TPO roofing system, valued for its energy efficiency, longevity, and low-maintenance performance. Set on nearly a half-acre with open space on two sides, this high-elevation property stands apart! Ideally positioned in Sea Pines on a quiet street almost directly between the Sea Pines Beach Club and the Harbourtown Yacht Basin! Tastefully furnished for immediate gratification!

41 Willow Oak W Road, Hilton Head Island

Listing courtesy of Collins Group Realty.

$1,299,000

4 Beds ⋅ 3 Baths ⋅ HILTONHEAD-511471 MLS

22 Doubloon Dr is nestled beneath majestic live oaks on a nearly 0.6-acre homesite in the sought-after oceanfront community of Port Royal. This beautiful home offers exceptional privacy, picturesque golf views, and a prime Hilton Head Island lifestyle. A long driveway and oversized 3-car garage provide abundant parking and storage. Inside, you'll find 4 bedrooms, 3 full baths, smooth ceilings, wood flooring, a welcoming fireplace, and a large laundry room. The updated kitchen features new appliances, while the updated guest baths, fresh interior paint, BRAND NEW HVAC AUGUST 2026, and new windows make this home truly move-in ready. Enjoy year-round natural light from the sunroom or relax and entertain on the expansive wraparound patio overlooking the tranquil golf course. Located outside the flood zone, this home combines peace of mind with timeless Lowcountry charm. Residents of Port Royal enjoy private beach access, tennis, pickleball, leisure trails, and a private oceanfront beach club with pool in one of Hilton Head Island's most desirable gated communities. Some furniture is negotiable.

22 Doubloon Drive, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc - Bluffton.

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