Your Retirement Checklist: Steps to Join the Founders Club with Confidence

Retirement is here – a time of freedom, fulfillment, and new possibilities. But enjoying it to the fullest still requires thoughtful planning.
Even after you’ve stepped away from work, questions about healthcare, home upkeep, and long-term security can weigh on your mind.

That’s why having a clear retirement checklist matters. Below are practical steps to help you protect your lifestyle and enjoy the retirement you’ve earned – plus how The Winsberg at Green Cay, a Life Plan Community opening in Boynton Beach in late 2027, can help you thrive with peace of mind.

Take Inventory of All Your Assets

Your retirement checklist starts with a complete review of your financial picture. Look at bank accounts, retirement accounts, pensions, investment portfolios, life insurance policies, and Social Security benefits. A trusted financial advisor can help assess where you stand and ensure your plan supports both short- and long-term goals.

Knowing the value of your assets also helps you anticipate unexpected costs and make better decisions about preparing for healthcare expenses, potential home maintenance costs or even downsizing. Clarity today means fewer surprises tomorrow.

Review and Update Estate Plans

No retirement checklist is complete without reviewing your estate planning documents. Update your will, trusts, and powers of attorney to reflect your current wishes. This step ensures your assets are protected and gives your loved ones clarity and peace of mind.

Estate planning isn’t just about managing wealth – it’s about providing stability and avoiding stress for family members in the future.

Plan for Future Healthcare Costs

Healthcare is one of the biggest retirement expenses, and it’s important to plan for it early. Understand what Medicare covers, account for deductibles, and explore supplemental health insurance or long-term care coverage.

At The Winsberg, healthcare planning is built in. As a Life Plan Community, residents benefit from access to health services at discounted rates, including assisted living, memory care, and skilled nursing – removing the stress of unexpected health care expenses and giving you peace of mind for the future. 

Consider Rightsizing for Simplicity and Savings

For many retirees, rightsizing is a powerful way to simplify life and reduce costs. Moving from a large home to a smaller residence can free up equity, lower utility bills, and eliminate the burden of upkeep.

At The Winsberg, this transition is more than financial – it’s about gaining freedom and a lifestyle. Our community provides modern residences, engaging programs, social opportunities, and maintenance-free living so you can focus on what matters most. And, in a community of your peers, friendships will come easily. In fact, many of our Founders Club members are already forming friendships, attending exclusive social events, and participating in book and card clubs.

Join the Founders Club for Peace of Mind and Connection

Beyond finances, retirement is about community, purpose, and connection. Joining the Founders Club at The Winsberg at Green Cay gives you early access to all these benefits, well before the community opens in 2027.

• Priority residence selection to secure your ideal home.
• Invitations to exclusive Founders Club events—from card clubs and breakfast meetings to holiday celebrations.
• A private Facebook group where you can build friendships before move-in.
• Confidence knowing your future includes maintenance-free living, lifestyle amenities, and healthcare support.

It’s one more way to “check off” your retirement planning goals with confidence.