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    “The Cypress is my home now; I own it, and I love it!”
The Cypress of Hilton Head Island An Award-winning Continuing Care Retirement Community





Equity Ownership

The Cypress allows our members to enjoy the financial advantages of home ownership without the headaches of owning and maintaining a property. From apartments to condos to cottages 800-4,000 square feet, you’re sure to find something perfect for your lifestyle.


The Cypress Club

The Cypress Club, owned by our members, is debt-free and operates as a not-for-profit; therefore, the monthly fees and health center costs are affordable and predictable and are often times much lower than other retirement communities.


Extraordinary, dining experiences

Our members can choose from several dining attractions located in The Clubhouse. Excellent service and a wide variety of delicious menu options for dine-in or delivery.


Preston Health Center

The Preston Health Center is a Medicare-licensed facility offering progressive rehabilitative care, assisted living, dementia and long-term, skilled nursing care. It’s conveniently located on our campus if there is ever a need.


Beautiful 100-acre campus

If you love the outdoors, you will love exploring our walking trails and fishing in our lakes. There is even a private 3-hole Cypress Club Golf Course, and a pier and dock on the Intracoastal Waterway.


True sense of security

Our members enjoy the security and peace of mind of a fenced and gated community inside Hilton Head Plantation with round-the-clock security on their 100 acre campus.


A wide variety of organized activities and outings

Whether it’s a day trip, an art or fitness class, a guest speaker or a concert, the Cypress always has something going on for those who want to attend.


Luxurious amenities

We provide our members with everything they could possibly need. Our clubhouse is home to our fitness and wellness center, heated pool, salon, game room, art studio, library and more! Utilize them as often as you wish!


World Class Service

We offer country club style, hospitality-based services by quality-trained employees. Our employees will know your name, your favorite drink and how you like your home cleaned. They will exceed your expectations and are proud of it!


The People

But, if you ask a member “Why the Cypress?” they will say “It’s the people… the members, the staff, my neighbors and friends.” That is what sets us apart from other communities. Because our members don’t just rent or pay a fee to move in, they invest in their community and their friendships here.

The Cypress of Hilton Head | 20 Ladyslipper Lane, Hilton Head Island, SC 29926

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Summertime is in full swing at the Cypress and Becky is providing us the latest update on the Senior Network! ☀️🏖️🌻Learn more about what's happening at the Cypress this summer: #RetirementCommunity #SeniorLiving #HiltonHead #IndependentLiving #CCRC #HHI #SeniorNetwork


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The Cypress of Hilton Head Island is located at 20 Ladyslipper Lane, Hilton Head Island, SC 29926, within Hilton Head Plantation.

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