The Cypress of Hilton Head

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Hilton Head Island, SC
The Cypress of Hilton Head

Hilton Head's Premier Life Plan Community offering resort style living in a glorious seaside setting.

Life is good in South Carolina’s Lowcountry, something you’ll quickly find out living at The Cypress. Located on beautiful Hilton Head Island, one of America’s most appealing leisure destinations, The Cypress offers resort-style living in a glorious seaside setting. With all the modern conveniences you’d expect from a premier Life Plan Community and access to everything Hilton Head has to offer, The Cypress is a dreamy place to enjoy the retirement life you’ve always imagined.

11/06/2025

Another year, another unforgettable Fall Fling! 🍂🎷🎶🎃 Members gathered for our annual Halloween celebration, enjoying hors d’oeuvres in the Bistro before dancing the night away with Target the Band and The Headliner Horns.

Cheers to fabulous festivities and great company! 🥰🥂 Until next year!

11/04/2025

When you’re a member at The Cypress, you get to select, furnish, and enjoy the home that best suits your needs — and get the equity benefits of being a property owner. Homeownership is just one of the many things that set The Cypress apart from other Life Plan Communities.

All residences, from waterfront homes to convenient apartments, include weekly housekeeping and linen service, as well as complimentary maintenance and repair.

We invite you to discover everything The Cypress of Hilton Head has to offer and to take advantage of the unique opportunity to enjoy an extraordinary lifestyle every single day. Schedule a tour and check it out for yourself by visiting www.cypressofhiltonhead.com

10/31/2025

There’s magic in the Lowcountry air tonight! Wishing you treats, laughter, and a touch of Halloween mischief from all of us at The Cypress of Hilton Head 👻🧡

10/29/2025

The Halloween spirit is alive and well at The Cypress, with pets leading the parade in full costume regalia! 🎃🐾 Our Halloween Pet Pawty has become a cherished annual tradition, where members, staff, and our beloved animal companions gather to celebrate the season in a way that’s equal parts festive and heartwarming.

Each year, this special gathering reminds us that friendship comes in all shapes, sizes, and wagging tails. It’s just one more example of the vibrant, connected lifestyle that makes The Cypress of Hilton Head feel like home—for every member of the family.

Thank you to everyone who joined us and helped make this event a true highlight of our fall season! 🦮🐩🐕‍🦺

10/24/2025

Saddle up! 🐎 We’re sharing even MORE moments from Western Night — double the photos, double the fun! With Justin Cruise keeping the music lively, everyone line danced, tapped along, and enjoyed delicious bites throughout the evening.

From the first note to the last beat, it was a night of music, dancing, and memories made to last. 🪕

10/22/2025

Nestled in the scenic surroundings of The Cypress of Hilton Head's captivating campus, The Preston Health Center offers an idyllic location for exceptional healthcare services. As a Medicare-certified establishment, we cater to the needs of both residents and non-residents of The Cypress community, providing comprehensive short-term, long-term, and memory care services.

We invite you to come experience The Preston difference firsthand. Please visit www.theprestonhealthcenter.com

10/21/2025

Our Golden Isles getaway took us from the sweeping views atop the St. Simons Lighthouse to the historic charm of the Hofwyl-Broadfield Plantation and the fascinating exhibits at the World War II Museum. Each stop offered something new to see, learn, and enjoy — from breathtaking panoramas to stories of the past that brought history to life.

Between exploring historic sites, taking in scenic views, and enjoying unexpected surprises around every corner, this trip was packed with experiences that will be remembered long after we returned home.

10/17/2025

Buon appetito! 🇮🇹 Recently at The Cypress, we celebrated Italian Night with delicious pasta, fine wine, and desserts that had everyone saying, “Mamma mia!”

From clinking glasses to stories shared around the table, Italian Night reminded us why life at The Cypress of Hilton Head is so special — a place where great food, warm friendships, and memorable moments come together in perfect harmony. 🍷✨

10/14/2025

Giddy up, Cypress Members! 🤠 Western Night was an evening full of laughter, great music, and Southern charm — the perfect way to celebrate community and good company. Members enjoyed line dancing, delicious bites, and toe-tapping tunes that had everyone smiling from ear to ear.

Nights like these remind us just how special life at The Cypress of Hilton Head truly is — where every gathering feels like a celebration among friends.

10/08/2025

Our recent visit to the Owens-Thomas House offered a fascinating glimpse into Savannah’s rich and layered history.

The guided tour took us through beautifully preserved rooms and thought-provoking exhibits, sharing stories of both privilege and perseverance. Afterward, we enjoyed exploring Historic Savannah, soaking in the sights, sounds, and charm of this iconic city.

We’re so grateful for the opportunity to learn, reflect, and share this experience as a community — what a meaningful day with such a wonderful group of members!

Telfair Museums

09/29/2025

Enjoy apartment-style living with amenities that include large master suites, high ceilings, large windows, and spacious living and dining rooms.

Ideally situated along The Cypress Golf Course and only a stone’s throw from The Clubhouse, The Cypress Villas offer members an outstanding blend of comfort and convenience.

To learn more about The Cypress, schedule a campus tour, or register to view our virtual tour, please visit www.cypressofhiltonhead.com

09/23/2025

We had a wonderful experience during our tour of Historic Mitchelville Freedom Park recently! Immersed in Mitchelville’s rich history, we were deeply moved by the resilience and unity that has defined this community.

We ended our trip with a beautiful dinner aboard one of our favorite exurcisions, dog tours, taking in the gorgeous skyline as we cruised the river. Another trip to remember!

Address

20 Ladyslipper Lane
Hilton Head Island, SC
29926

Website

http://www.cypressofhiltonhead.com/

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