Should You Retire in Place or Move?
- Nov 11
- 4 min read
Retirement is one of life’s biggest transitions and one of the most exciting. It’s the moment you can finally shape your days around your priorities instead of your job’s demands. But there’s one big question you’ll have to answer before you get too comfortable in your rocking chair: Do you stay where you are, or do you move somewhere new?
For many people, this decision is more complicated than it seems. Staying put offers familiarity and stability, while moving can open the door to new experiences, climates, and tax advantages. Naples, Florida, often tops the list of dream destinations for retirees, both full-time and part-time. Let’s walk through the key considerations so you can weigh your options
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The Case for Retiring in Place
Staying in your current home and community has some strong advantages:
Familiarity - You know the neighborhood, your local stores, and your go-to service providers. There’s comfort in the known.
Established Social Circles - Your friends, neighbors, and social connections are already in place, making it easy to maintain your support network. Interestingly enough we tend to sometimes see retired new comers come in pods... one couple comes first and are then followed by others in their social circle or town.
Lower Upfront Costs - If your home is paid off or nearly so, staying may be more affordable in the short term.
No Moving Stress - Avoiding the logistical and emotional toll of selling, packing, and relocating.
However, staying put may also mean missing out on potential lifestyle upgrades like warmer weather, more activities, or lower taxes that could make your retirement years even more fulfilling.
The Case for Relocating in Retirement
If you’ve been dreaming of a change, relocation can be a fresh start. Benefits include:
Lifestyle Fit - You can choose a location that matches your retirement goals: beach life, golf, arts and culture, or a quiet rural escape.
Better Climate - Many retirees trade harsh winters for sunny, temperate climates that allow year-round outdoor living.
Lower Taxes - Certain states, like Florida, offer significant tax advantages for retirees.
Proximity to Family - Moving closer to children or grandchildren can be a big motivator.
Why Naples, Florida Is a Top Pick for Retirees
Naples has earned a reputation as one of the most desirable retirement destinations in the U.S. and it’s easy to see why:
Year-Round Sunshine - Say goodbye to shoveling snow and hello to golf, boating, and beach walks any month of the year.
Vibrant Lifestyle - From world-class dining and shopping to theater, art galleries, and outdoor festivals, Naples offers activities for every interest.
Strong Retirement Community - Whether you want an active adult neighborhood, a luxury high-rise, or a quiet gated community, there’s a fit for every lifestyle.
No State Income Tax - Florida’s tax-friendly environment is a big draw. Many retirees also take advantage of Collier County's low property tax rate of 1.25% and Florida’s Homestead Exemption, which can help reduce property taxes for permanent residents.
Strong Specialty Healthcare - Naples is home to excellent medical facilities and specialists, an important consideration in retirement.
Considerations Before Making the Move
While Naples has plenty of appeal, relocating anywhere requires careful planning. Here’s what to think about:
1. Cost of Living
Naples offers a high-quality lifestyle, but certain expenses, especially housing, can be higher than the national average. Factor in property taxes, HOA fees, insurance, and day-to-day living costs.
2. Housing Needs
Do you want to downsize? Upsize to have space for family visits? Opt for a condo with less maintenance or a single-family home with a yard?
3. Healthcare Access
If you have specific medical needs, research local providers and hospital systems to ensure they meet your requirements.
4. Seasonal vs. Full-Time Living
Naples has a significant seasonal population. Some retirees keep a home up north for summer and spend winters in Florida. This can give you the best of both worlds, but requires managing two properties.
5. Legal & Tax Planning
While Florida’s lack of a state income tax is appealing, you should talk with your CPA and attorney to understand all the implications especially if you’re selling assets, changing residency, or have estate planning considerations.
6. Lifestyle Fit
Visit Naples (or any potential destination) during both peak season and the slower summer months to make sure the pace and atmosphere match your preferences year-round.
The Trade-Offs
Relocating can mean leaving behind a familiar home, friends, and community, but it can also mean gaining better weather, new experiences, and potential financial benefits. Staying put can preserve stability but may also keep you tied to a climate, cost structure, or lifestyle that no longer serves your needs.
There’s no one-size-fits-all answer to the “retire in place or move” question. It comes down to balancing lifestyle goals, financial realities, and personal priorities.
If you’re considering a move to Naples, I can help you explore neighborhoods, understand the housing market, and connect you with trusted local professionals. And remember—before making any big decisions about residency or taxes, consult your CPA and attorney to make sure it’s the right move for you legally and financially.
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