Hilton Head Island Homes with Insurance Association amenities

Welcome to Hilton Head Island, a gem nestled in Beaufort County, South Carolina. Renowned for its stunning beaches, lush landscapes, and vibrant community, Hilton Head Island offers a unique blend of relaxation and adventure. With its temperate climate, this picturesque locale is perfect for year-round living or seasonal getaways.

Hilton Head is famous for its pristine shores, where soft sands meet the Atlantic Ocean, inviting residents and visitors alike to indulge in sun-soaked days and breathtaking sunsets. Beyond the beach, the island boasts an array of outdoor activities, including world-class golf courses, scenic biking trails, and water sports, ensuring there’s something for everyone to enjoy.

The real estate market here is as diverse as its landscape, featuring charming beach cottages, luxurious waterfront estates, and everything in between. For those looking to invest, homes in Hilton Head Island are often part of the Homes with Insurance Association, providing residents with peace of mind through comprehensive insurance options. This association not only enhances the value of your investment but also fosters a sense of community among neighbors who share the same commitment to maintaining their properties.

Living in Hilton Head Island means embracing a lifestyle filled with rich cultural experiences, from art galleries and live music to gourmet dining and seasonal festivals. Whether you’re strolling through the quaint shops or savoring fresh seafood at a local restaurant, the island’s charm is undeniable.

Discover the beauty and tranquility of Hilton Head Island, where your dream home awaits amidst the splendor of South Carolina’s coastal paradise.

Newest Hilton Head Island Homes with Insurance Association amenities

$299,900

2 Beds ⋅ 3 Baths ⋅ 1,389 SqFt. ⋅ HILTONHEAD-512130 MLS

Hilton Head living without the Hilton Head price tag! This inviting 2-bedroom, 2.5-bath villa in The Gatherings offers a rare opportunity to own on Hilton Head Island at an approachable price point, with the added benefit of a low-maintenance lifestyle. Ideally positioned near the foot of the Hilton Head bridge, this location provides quick access to everything the Island offers while keeping Bluffton, Bluffton Parkway, shopping, dining, and everyday conveniences just minutes away. Inside, an updated kitchen opens to a generous dining and living area, creating a comfortable, spacious feel for everyday living or entertaining. Step outside to the wooden deck overlooking a peaceful lagoon setting-an ideal spot for morning coffee, relaxing at the end of the day, or simply enjoying the Lowcountry surroundings. What truly sets The Gatherings apart is its unique ownership structure. Although legally classified as a condominium, the community includes a variety of home styles, and the regime handles many major exterior responsibilities, simplifying ownership. Regime services include building maintenance, landscaping, insurance components, common water and sewer, pest control, refuse, pool maintenance, and more. The community also offers a pool, assigned parking, and a convenient residential setting. Whether you're looking for a primary residence, lock-and-leave second home, downsizing opportunity, or an affordable way to establish your Hilton Head Island address, this property delivers an appealing combination of location, lifestyle, and value.

111 Sutherland Way Unit 111, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$278,000

3 Beds ⋅ 3 Baths ⋅ 1,250 SqFt. ⋅ HILTONHEAD-511388 MLS

Perfectly situated for easy access to Hilton Head Island or Bluffton! This well maintained 3 bed, 3 bath stand alone condo offers spacious living with a large outdoor deck and onsite amenities! Approximately 1,250 square feet, this property presents an outstanding opportunity as a full-time residence, vacation getaway, or investment property. This light and bright home features an eat-in kitchen that opens up to the large living room, enjoy wood floors, stainless steel appliances, granite countertops and plantation shutters throughout! The first floor offers two comfortable bedrooms, two full baths, and a conveniently located laundry closet. Upstairs, you'll find a spacious private suite complete with a large bedroom, full bath, and generous closet space, as well as storage -perfect as a primary retreat or private guest suite. The Gatherings is an established neighborhood with a welcoming atmosphere and longtime residents. Close to shopping and restaurants, this home is a must see!

38 Wee Drive Unit 38, Hilton Head Island

Listing courtesy of Engel & Volkers.

$284,000

3 Beds ⋅ 3 Baths ⋅ 1,254 SqFt. ⋅ HILTONHEAD-511188 MLS

Great Value You Don't Want to Miss! Finding a 3-bedroom, 3-bath home on Hilton Head Island at this price is becoming increasingly rare. Offering approximately 1,250 square feet, this free-standing condo in The Gatherings presents an outstanding opportunity as a full-time residence, vacation getaway, or investment property. Well-maintained and move-in-ready, featuring a bright, inviting living room and a cheerful eat-in kitchen that serves as the heart of the home. The first floor offers two comfortable bedrooms, two full baths, and a conveniently located laundry closet. Upstairs, you'll find a spacious private suite complete with a large bedroom, full bath, and generous walk-in closet-perfect as a primary retreat or private guest suite. Step outside to enjoy the private deck or take advantage of the community pool located directly across the street. The Gatherings is an established neighborhood with a welcoming atmosphere, longtime residents, and an exceptionally convenient location offering easy access to both Hilton Head Island and Bluffton. Select restaurants and shopping are within near distance, adding to the convenience of everyday island living.If you've been searching for an affordable Hilton Head address without sacrificing space, comfort, or convenience, this home deserves a place at the top of your list.

36 Wee Road Unit 36, Hilton Head Island

Listing courtesy of Charter One Realty.

$299,999

2 Beds ⋅ 2 Baths ⋅ 1,254 SqFt. ⋅ HILTONHEAD-510727 MLS

4BR/3BA stand-alone condo in The Gatherings community, Hilton Head Island. 1,950 sq ft. Two primary suites on the first floor for easy one-level living. Bright, open layout with abundant natural light. Enjoy the private deck overlooking serene lagoon views and wildlife.Community amenities: pool, tennis, basketball courts, and playground. Excellent location at the foot of the bridge with easy access to beaches, shops, restaurants, and Bluffton. Great investment opportunity for primary residence, vacation home, or rental income.

42 Wee Road Unit 42, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$325,000

4 Beds ⋅ 3 Baths ⋅ 1,950 SqFt. ⋅ HILTONHEAD-510643 MLS

Beautifully remodeled & meticulously maintained 4-bed 3-bath home located in the lovely community of The Gatherings. Conveniently located at the mouth of the Hilton Head bridge, the home boasts a HHI address while being located in Bluffton; the location doesn't get much better. Newer cabinets, subway tile backsplash, and granite countertops invite you into the fresh kitchen space. 52 Salt Marsh offers a first-floor primary w/ a fully renovated bathroom and custom tiled shower, w/ laundry room and second bed/bath across the hall. Upstairs includes its own two-bedroom retreat and bath with a centrally located kitchenette separating the two spaces. A large back deck offers tranquil lagoon views. Technically classified as a condo, you get all the pros of villa living, yet with the space and privacy of a single-family home w/ a true lock and leave opportunity. The Gatherings easily offers the best bang for your buck in the area. Home was fully repainted in July 2026. HVAC replaced in 2022. The home has been fully replumbed w/ PEX and spray foamed with all new flooring. New tubs in both auxiliary bathrooms were added in July 2026. Home receives two assigned parking spots. This is truly a turn key opportuniy for a primary, secondary, or proven investment property.

52 Salt Marsh Drive Unit 52, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$310,000

4 Beds ⋅ 3 Baths ⋅ 1,250 SqFt. ⋅ HILTONHEAD-510380 MLS

Motivated Seller. Nestled among mature trees in the desirable Gatherings community, this spacious 4bedroom, 3bath, 1741sq ft home offers the perfect blend of privacy, comfort and convenience. Soaring vaulted ceilings, abundance natural light, and an inviting fireplace create a warm and welcoming atmosphere. The open concept features hardwood flooring, a spacious kitchen and is a seamless flow between living, dining and entertaining areas. Large windows and sliding doors bring the outdoors in, showcasing peaceful wooded and lagoon views from nearly every room.The primary suite offers a relaxing retreat with generous closet space and an en-suite bath. Step outside to an expansive private deck overlooking a serene natural setting with lagoon.Steps away residents enjoy access to a community swimming pool, tennis courts and playground.Experience Lowcountry living at it's best in this charming home.The house has just been painted on the outside. The landscaping is well maintained by the regime. Security patrol on site. New washer, dryer, dishwasher, and new blinds and ceiling fans throughout the home. Two assigned parking spots, up to four vehicles. Zoned for Hilton Head Island schools. Convenient to Tanger Outlets, Bluffton and Savannah. HOA includes flood insurance.

58 Pine Burr Road Unit 58, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$330,000

4 Beds ⋅ 3 Baths ⋅ 1,950 SqFt. ⋅ HILTONHEAD-510211 MLS

Perfectly positioned at the gateway to Hilton Head Island yet firmly rooted in the heart of beautiful and historic Bluffton, this precious 4-bedroom, 3-bath property offers more than just a place to live - it offers a way of life. Unlike a traditional condo or townhome, this home has no shared walls, no neighbors above or below, and lives just like a private single-family residence. You get the privacy, space, and independence of your own home, while enjoying the convenience and lower-maintenance lifestyle that comes with condominium ownership. Imagine mornings spent sipping coffee on your back deck as the birds and wildlife awaken around you. Inside, the home welcomes you with warm coastal charm, inviting spaces, and room for everyone you love. What truly sets this property apart is its place within the newly imagined community of The Gatherings. Designed around connection, friendship, and the simple joys of everyday life, this is a neighborhood where front porches matter, conversations happen naturally, and neighbors become lifelong friends. This isn't just another home for sale. It's a front-row seat to the beauty of the Lowcountry. A launching point for Island adventures. A place where memories will be made for years to come. A coastal cottage that captures everything people dream about when they imagine living where the marsh meets the ocean. Your Regime fee covers insurance, roof, security, exterior maintenance and trash collection - truly carefree living. Incredible opportunity for an investment property, second home or primary coastal escape. Some homes are viewed. Others are experienced. And this one simply must be seen to be fully appreciated. Come discover what life can look like when charm, location, community, and the beauty of the South Carolina coast come together in one unforgettable place.

48 Salt Marsh Drive Unit 48, Hilton Head Island

Listing courtesy of Charter One Realty.

$279,900

3 Beds ⋅ 3 Baths ⋅ 1,250 SqFt. ⋅ HILTONHEAD-510207 MLS

Seller motivated with fantastic new deal. Ideally located with a Hilton Head Island address while offering convenient access to Bluffton, this unique property combines value, space, and lifestyle. Classified as a villa, yet truly living like a detached single-family home, this spacious 3-bedroom, 3-bath residence offers privacy and comfort rarely found at this price point.Filled with natural light, the open and airy floor plan creates an inviting atmosphere perfect for both everyday living and entertaining. Enjoy relaxing on the charming front porch overlooking expansive common green space, adding to the home's peaceful setting and sense of openness.Offering exceptional square footage, functionality, and location, this property presents a fantastic opportunity for full-time living, a second home, or investment on Hilton Head Island.

66 Black Watch Drive Unit 66, Hilton Head Island

Listing courtesy of Palmetto Coastal Realty.

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