Headlands Homes with Trail(s) Association amenities

Welcome to Headlands, a picturesque subdivision nestled on the enchanting Hilton Head Island in Beaufort County, South Carolina. This charming community is a hidden gem, offering a perfect blend of coastal living and serene suburban comfort. Residents of Headlands enjoy a tranquil lifestyle, surrounded by lush landscapes, natural beauty, and the soothing sounds of the nearby ocean.

The homes in Headlands are designed with both elegance and functionality in mind, featuring spacious layouts, modern finishes, and ample outdoor spaces that invite you to bask in the island's warm sunshine. Whether you’re looking for a cozy retreat or a family-friendly abode, Headlands offers diverse options to suit every lifestyle.

One of the standout features of the Headlands community is its Homes with Trail(s) Association amenities. Residents can take advantage of beautifully maintained walking and biking trails that wind through the neighborhood, providing a perfect setting for morning jogs, leisurely strolls, or family outings. The association fosters a strong sense of community, organizing events and activities that bring neighbors together, ensuring a vibrant and engaging atmosphere.

Living in Headlands means you’re just moments away from the stunning beaches, world-class golf courses, and a variety of dining and shopping experiences that Hilton Head Island has to offer. With its idyllic location and exceptional amenities, Headlands is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the charm of Headlands, where your dream home awaits!

Newest Headlands Homes with Trail(s) Association amenities

$749,000

3 Beds ⋅ 2 Baths ⋅ 1,635 SqFt. ⋅ 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 ⋅ 2,832 SqFt. ⋅ 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.

Start Your Search

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.