Real Estate // 4 min Read

Tour This 24-Acre Private Estate in Palmetto Bluff’s Most Exclusive Enclave

Written by Palmetto Bluff

Tucked deep in the maritime forest and bordered by the headwaters of the May River, 11 Headwaters Road is one of the most private and secluded properties in Palmetto Bluff. Set on 24 acres within a gated enclave of just ten legacy estates, this seven-bedroom, eight-and-a-half-bath compound offers rare seclusion, exceptional craftsmanship, and generous spaces designed for gathering across generations.

Built for Generational Living

Designed by Wayne Windham and built by Johnson-Dulaney, the main house pairs scale with detail – reclaimed pine floors, a soaring great room with tabby fireplace, and a chef’s kitchen anchored by a quartz island and wine cellar. The first-floor primary suite features dual en suite baths, two walk-in closets, and private porch access. Upstairs, a guest suite and additional bedroom flank a quiet sitting room.

With a full apartment above the carriage house and a three-bedroom guest house nearby, the estate easily accommodates family holidays, summer weekends, and spontaneous gatherings. Each structure is surrounded by layered landscaping, native trees, and garden paths that lead to quiet pockets of stillness.

Outdoor Living That Flows Naturally

The outdoor experience at 11 Headwaters Road is designed for year-round use and complete immersion in the landscape. Three separate fire pits anchor gathering areas across the property, creating distinct zones for entertaining, relaxing, or retreating into nature. 

Wide screened porches extend the living space, while wooded trails and native landscaping lead to tucked-away seating areas throughout the property. A private owner’s dock on Lake Haynes invites morning paddles, afternoon fishing, or coffee at sunrise. Every detail was considered to create a home that lives as comfortably outside as it does in.

Club Life
Wilson Village Welcomes The Chandlery

Tucked along picturesque Boat House Row in Palmetto Bluff’s iconic Wilson Village, The Chandlery offers a shopping experience inspired by the art of living well. This thoughtfully curated boutique brings together a unique collection of elegantly chic home furn...

Oct 2026

Club Life
Sit & Stay Awhile with the Latest Issue of the bluff Magazine

Fall is in the air as we welcome a new season at Palmetto Bluff. After a year marked by new beginnings and long-awaited plans coming to life, it feels only fitting to celebrate the final months of 2026 with the latest edition of the bluff magazine. The Fall...

Oct 2026

Real Estate
A West Wilson Home Built for Privacy and Scale

32 Gilded Street: A West Wilson Estate Defined by Craftsmanship and Courtyard Living  In West Wilson, one of Palmetto Bluff’s most sought-after neighborhoods, 32 Gilded Street pairs timeless Lowcountry architecture with rare privacy. Designed by Ludtke & ...

Sep 2026

Food & Wine
Where to Eat Oysters This Season in the Lowcountry

Oyster Season in Palmetto Bluff: A Lowcountry Tradition As the air cools, the light softens, and the landscape begins to shift, a familiar feeling returns to the Lowcountry: oyster season. From October through March, friends and neighbors gather around steami...

Sep 2026

Real Estate
Why Fall Is the Perfect Season to Invest in a Second Home at Palmetto Bluff

The Case for Buying a Home in the Fall at Palmetto Bluff Buying a home in the height of a Lowcountry summer can test even the most enthusiastic house hunter. Fall brings a welcome change of pace, with milder weather and more comfortable days for exploring own...

Sep 2026

Club Life
The Cottage Arrives at Anson Point

After opening its doors in August, The Cottage at Anson Point, has quickly become a favorite among Golf Members looking to linger before (or after) hitting the fairway. Tucked into the trees near Anson Point’s 18th hole, The Cottage feels both refined a...

Sep 2026

Conservation
Beyond the Bluff: A Costa Rica Nature Adventure

Photos courtesy of Carlos Chacón and Patrick O’Brien The Palmetto Bluff Conservancy creates opportunities for Members and Conservancy supporters to deepen their connection to the natural world, both within the Bluff and beyond. In October 2027, that spirit ...

Sep 2026

Club Life
Fall at The Farm: New Plantings and New Plans

A new season is taking shape at The Farm, where fall planting is underway and plans are progressing for expanded growing space in the months ahead. Farm Manager Shane Rahn and his team began planting for the fall season in September, starting with 320 squas...

Sep 2026

Culture
See the Bluff Through an Artist’s Eyes: Raven Roxanne at Palmetto Bluff

This October, Charleston-based abstract impressionist painter Raven Roxanne comes to Palmetto Bluff for two days of art, nature, and creative exploration inspired by the Lowcountry landscape.Known for her expressive use of color, texture, and movement, Raven f...

Sep 2026

Artist in Residence
Material Memory

Photographs & Story by Hailey Wist As the November Artist in Residence with The Arts Initiative at Palmetto Bluff, Arun Drummond showcased a practice that balances form and cultural memory, emphasizing how portraiture can both honor and illuminate. ...

Sep 2026

CURIOUS ABOUT LIFE AT THE BLUFF?

Sign up for our newsletter

LIVE
Community Villages
Experience
Palmetto Bluff Club
On The Water
The Arts Initiative
Events
Conserve
About Us