The Cypress of Hilton Head: A Retirement Community on Calibogue Sound

What The Cypress offers and who lives there

The Cypress of Hilton Head is a continuing care retirement community (CCRC) located on Calibogue Sound in Hilton Head Island, South Carolina. The community serves older adults who want to remain in one place as their care needs change—moving from independent living to assisted living to skilled nursing without leaving the property. Residents live in private apartments, cottages, and villas across a waterfront campus.

The community is operated by Brookdale Senior Living, a national operator of senior housing. The Cypress draws residents from across the country, though many come from the Lowcountry and the Southeast. The setting emphasizes water views, walking trails, and access to Hilton Head's recreational and cultural life.

Key Takeaways

• The Cypress is a continuing care retirement community where residents can age in place, moving between independent living, assisted living, and skilled nursing care on the same campus.
• Housing options include private apartments, cottages, and villas, each with different floor plans and price points.
• Residents pay an entrance fee (which varies by unit type) plus monthly service fees that cover utilities, maintenance, activities, and dining options.
• The community includes on-site amenities such as a fitness center, library, restaurant-style dining, and organized social and recreational programs.
• Prospective residents and their families should tour the community, review the Resident Agreement, and understand the financial structure before making a decision.

Housing types and what each includes

The Cypress offers three main housing categories. Independent living apartments range from studios to two-bedroom floor plans and are designed for residents who do not yet need daily assistance. Assisted living residences provide private rooms or suites with support for activities of daily living—bathing, dressing, medication management, and meals. Skilled nursing care is available on-site for residents who need medical oversight, rehabilitation after hospitalization, or round-the-clock care.

Each housing type sits in a different building or section of the campus, though residents can move between levels without leaving The Cypress. Independent living units typically feature full kitchens, washer-dryer hookups, and patios or balconies. Assisted living and skilled nursing rooms are smaller and designed for safety and accessibility, with grab bars, emergency call systems, and proximity to staff.

The community also offers respite care—short-term stays for people recovering from surgery or illness—and adult day programs for residents who live off-campus but want daytime activities and supervision.

Entrance fees and monthly costs

The Cypress operates on a fee-for-service model, which means residents pay both an upfront entrance fee and ongoing monthly charges. The entrance fee varies significantly based on the unit type, size, and current market conditions. A studio independent living apartment costs less than a two-bedroom cottage; assisted living and skilled nursing entrance fees differ as well. The community does not publicly post these figures online, so you will need to contact them directly or schedule a tour to receive current pricing.

Monthly service fees cover utilities (except phone and cable), maintenance and grounds keeping, one meal per day in the dining room, activities and entertainment, use of common areas, and basic housekeeping. Additional meals, transportation, personal care services beyond what is included, and other services cost extra. Long-term care insurance, Medicare, and Medicaid may cover portions of assisted living or skilled nursing costs, depending on the policy and the resident's situation, but independent living is typically paid out of pocket.

Some residents finance their stay through a combination of savings, investments, and downsizing proceeds from selling a previous home. Others use long-term care insurance or Medicaid planning. The community's financial counselors can discuss payment options during the tour and application process.

Amenities and daily life at The Cypress

The Cypress campus includes a fitness center with equipment and classes, a library, a salon and spa, multiple dining venues, and outdoor spaces with walking paths and water views. The community organizes social events, educational lectures, fitness classes, arts and crafts, card games, and outings to local attractions. Residents can participate as much or as little as they choose.

The waterfront location means many residents enjoy the sound views, bird watching, and access to Hilton Head's beaches, golf courses, and restaurants. The community provides transportation to medical appointments, shopping, and cultural events. Residents can bring pets to independent living units, subject to the community's pet policy.

Dining is a central part of community life. Most residents eat at least some meals in the main dining room, where menus change regularly and dietary restrictions are accommodated. Independent living residents typically have one meal per day included; additional meals and in-unit dining services are available for an extra fee.

The application and move-in process

Prospective residents and their families begin with a tour of the campus, meeting with a sales counselor who explains the community's structure, services, and costs. The next step is to request a Resident Agreement—a legal document that outlines the terms of residency, fees, services, and what happens if a resident needs to leave or move to a higher level of care.

Most communities require a health screening and financial review before acceptance. The health screening ensures the community can meet the person's current care needs; if someone requires 24-hour skilled nursing care immediately, they may not be a fit for independent living. The financial review confirms the resident can pay the entrance fee and monthly charges, either through personal funds or insurance.

Once accepted, residents typically move in within a few weeks to a few months, depending on unit availability. The community helps coordinate the move and provides orientation to the campus, staff, and programs. Many residents bring furniture and personal items to make their apartment feel like home.

Understanding the continuing care model

The defining feature of a CCRC is that residents can stay on campus as their needs change. If an independent living resident develops arthritis or mobility issues and needs help with bathing or medication, they can move to assisted living without leaving their community, their friends, or their familiar surroundings. If they later need skilled nursing care, that is available on-site as well.

This model appeals to people who want to plan ahead and avoid multiple moves in their later years. It also means the community has a financial incentive to keep residents healthy and engaged—activities, fitness programs, and preventive care are part of the culture. However, it also means entrance fees are higher than in independent-living-only communities, because the community is committing to provide care across multiple levels.

Residents should understand that moving to a higher level of care may involve additional monthly fees beyond what they paid for independent living. The Resident Agreement spells out these costs, so it is important to read it carefully or have an attorney review it before signing.

Questions to ask before deciding

Before committing to The Cypress, prospective residents and their families should visit multiple times—once during the day, once in the evening, and once on a weekend if possible. Talk to current residents about their experience. Ask staff about staffing ratios, training, and turnover. Request references from residents who have moved to assisted living or skilled nursing, so you can hear about the transition experience.

Review the Resident Agreement line by line, paying attention to entrance fee refund policies, what happens if you need to leave, how monthly fees can increase, and what services are included versus what costs extra. Ask about the community's financial stability and whether it has ever had to close or merge with another operator. Understand the community's policies on end-of-life care, hospice, and what happens if a resident runs out of money.

Talk with your family, your financial advisor, and your doctor about whether a CCRC is the right choice for you. Some people thrive in a community setting with built-in social life and on-site care; others prefer to age in their own home or in a smaller, less structured environment.

Frequently Asked Questions

Can I visit The Cypress before deciding to move in?

Yes. The community welcomes tours and encourages prospective residents to visit multiple times and at different times of day. You can also request to have lunch in the dining room or attend an activity to get a feel for daily life. Current residents are often willing to talk about their experience.

What happens to my entrance fee if I move out or pass away?

Refund policies vary by community and by the type of contract you sign. Some communities offer a declining refund—you get back a percentage of your entrance fee if you leave within the first few years, but the percentage decreases over time. Others offer no refund. The Resident Agreement will specify the policy, so read it carefully before signing.

Does Medicare or Medicaid pay for The Cypress?

Medicare does not cover independent living or assisted living at a retirement community. Medicaid may cover assisted living or skilled nursing care in some states, depending on the resident's income and assets, but policies vary. Long-term care insurance may also cover portions of care. Discuss payment options with the community's financial counselors and with your own financial advisor.

What if I need more care than The Cypress can provide?

The Cypress provides independent living, assisted living, and skilled nursing care on-site. If a resident needs specialized care—such as memory care for advanced dementia or hospice—the community can discuss options, which may include transfer to a specialized facility or bringing in outside services. This is an important question to ask during your tour.

How much does it cost to move to The Cypress?

Entrance fees and monthly costs vary based on the unit type, size, and current market conditions. Contact the community directly or schedule a tour to receive current pricing and a detailed breakdown of what is included in monthly fees versus what costs extra.