Headlands Real Estate

Welcome to Headlands, an enchanting subdivision nestled in the heart of Hilton Head Island, South Carolina. This picturesque community captures the essence of coastal living, offering residents a serene escape surrounded by lush landscapes and stunning natural beauty. Headlands is renowned for its prime location, providing easy access to the island's pristine beaches, vibrant shopping districts, and a plethora of outdoor activities.

As you stroll through the charming streets of Headlands, you'll discover a delightful mix of architectural styles that reflect the region's rich heritage. The homes here are thoughtfully designed, featuring spacious layouts and modern amenities that cater to both relaxation and entertainment. Many properties boast breathtaking views of the Lowcountry's marshlands, making every sunset a memorable experience.

Living in Headlands means embracing an active lifestyle. The community is just a stone's throw away from world-class golf courses, scenic bike trails, and tranquil parks, ensuring that residents can enjoy the great outdoors year-round. For those who appreciate fine dining and shopping, Hilton Head Island offers an array of local boutiques and gourmet restaurants, making it easy to indulge in the island's vibrant culture.

Whether you’re looking for a permanent residence, a vacation home, or a rental investment, Headlands presents an incredible opportunity to immerse yourself in the laid-back luxury of Hilton Head Island living. Come discover the charm and elegance of this exceptional community—your dream home awaits in Headlands!

Newest Listings in Headlands

$749,000

3 Beds ⋅ 2 Baths ⋅ HILTONHEAD-512909 MLS

Beautiful golf course views and easy one-level living await at 62 Cypress Marsh Drive in Hilton Head Plantation. This inviting 3-bedroom, 2-bath home is filled with natural light and features a spacious kitchen with newer cabinetry, LVP flooring throughout, vaulted ceilings in the living room, and a comfortable, functional floor plan. Enjoy peaceful views of Bear Creek Golf Course from the screened porch or paved patio, perfect for morning coffee, outdoor dining, or simply relaxing. Additional highlights include an oversized 2-car garage and a newer HVAC system. Well maintained and move-in ready, this home also offers access to Hilton Head Plantation's exceptional amenities, including community pool, a lazy river, miles of leisure trails, beach access, golf, and more.

62 Cypress Marsh Drive, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$1,110,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-512235 MLS

Beat the rate hike and seize this HUGE opportunity to own a renovated home in the prestigious Hilton Head Plantation. This beautifully remodeled 3-bedroom, 2.5-bath home blends Lowcountry charm with modern sophistication. Enjoy serene lagoon views from your living spaces, an open-concept layout designed for effortless coastal living, and a thoughtfully updated interior featuring elevated finishes throughout, including show-stopping engineered hardwood flooring throughout the entire house. With spacious bedrooms, a light-filled kitchen, and inviting outdoor areas perfect for morning coffee or evening sunsets, this home delivers the ideal balance of comfort, style, and natural beauty. Unique newly added private office with its own private entrance adds 170 sf, giving you approx 3008 sf! Expansive windows allow in tons of natural light, custom painting, smooth ceilings throughout & so much more! The spacious 2-car garage with its private access to the fully FENCED yard only adds to the possibilities! This home is a must -see! Signature Amenities in Hilton Head Plantation include SpringLake Pool - A large resort-style pool complex with lap lanes, a splash area, and seasonal events; Dolphin Head Recreation Area - a waterfront park on Port Royal Sound with walking paths, picnic areas, and stunning sunset views; miles of leisure trails- over 12 miles of walking and biking trails winding through lagoons, marshes, and wooded preserves. Four Golf Courses can be found within the community: Country Club of Hilton Head, Bear Creek Golf Club, Dolphin Head Golf Club, and Oyster Reef. Multiple Tennis & Pickleball courts, clinics, and social play options for all skill levels. Community Gardens - Plots available for residents who enjoy gardening and seasonal planting. Skate Park - A unique amenity for families and active residents.Fishing & Lagoon Access - Dozens of stocked lagoons for catch-and-release fishing, plus scenic wildlife viewing. Seabrook Recreation Area - Open fields, playgrounds, and space for community gatherings. Security & Gated Access - 24-hour security, controlled gates, and private roads for peace of mind. Fitness classes, social clubs, volunteer groups, and year-round community programming.

9 Shadewood Lane, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

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