What to Know About Owning Multiple Properties in Retirement

Written by Allison Goodhart

For a lot of people, retirement isn’t about choosing one place to live anymore. It’s about figuring out how to spend more time in the places they love.

Maybe that means winters in Florida, summers at the beach, and enough time back in Alexandria to see the grandkids, catch up with friends, and enjoy the community they’ve called home for decades.

Sounds pretty great, right?

Years ago, when I interned for Barbara Corcoran, she was working on her book Nextville, which explored finding the right place for the next chapter of your life. I even ended up on the back cover! It’s funny how relevant that concept still is today.

After years of helping clients navigate moves, downsizing, and major life transitions, one thing I’ve learned is that there isn’t a single right answer. For some people, it’s one perfect home. For others, it’s having a few different places to call home.

But before planning winters in Florida and summers in Delaware, there are some important questions worth considering.

1. Where Do You Actually Want Your Home Base to Be?

This is where I’d encourage people to start, before getting too caught up in taxes or real estate prices.

Think about where you want to spend your time, not just where you want to own property.

Where are your family and closest friends?
Where do you want to spend holidays and special occasions?
Which location offers the lifestyle you enjoy most?
Where are your doctors and healthcare providers?
How much time do you realistically want to spend traveling between homes?

For many of our clients, Alexandria and the greater DC area remain an important part of their lives, even if they want to escape the winter weather.

Maybe you no longer need five bedrooms and a large yard, but you’d love a two-bedroom condo within walking distance of restaurants and shops. Or perhaps a smaller townhouse gives you enough space to host family while allowing you to travel more freely.

We’ve also written about buying a condo in DC to be closer to your adult children, which can be a wonderful option for parents who want to remain involved in family life without maintaining a large full-time residence.

You don’t necessarily have to choose between staying connected to your community and enjoying retirement somewhere else.

2. Should You Keep Your Current Home, Downsize, or Buy Something Else?

Let’s say you own a larger home in Alexandria but are thinking about spending four or five months a year in Florida.

Do you keep the house you’ve lived in for decades? Sell it and purchase a smaller condo or townhouse? Or maintain your current home while you figure out exactly what retirement looks like?

There are good reasons for each approach.

Keeping your current home may make sense if you still spend significant time here, enjoy the space when family visits, and are comfortable with the upkeep.

Downsizing locally can help you maintain your connections while reducing maintenance and potentially freeing up equity for a second property.

Selling and relocating entirely may be right if you’re ready for a new lifestyle and don’t anticipate spending much time back in the area.

Renting before buying is another option I often encourage people to consider. Spending a few weeks somewhere on vacation is very different from living there for several months. Try spending an entire season in your prospective new community before committing.

And remember, downsizing isn’t always just a financial decision. Selling the home where you raised your family can be emotional, even when you know it’s the right move.

If you’re considering that transition, our Downsizing Guide is a great place to start.

You can also read these posts next for more downsizing answers:

3. Where Should Your Legal Residence Be?

Now for the less exciting, but very important, part.

If you’re planning to own homes in multiple states, you’ll need to think carefully about your legal domicile, or the place you consider your permanent home.

This decision can have significant tax and estate-planning implications.

Florida, for example, has no individual state income tax, which can make it attractive for retirees splitting their time between Florida and the DMV.

But simply purchasing a Florida property doesn’t automatically make you a Florida resident for tax purposes.

States have different rules for establishing domicile and determining tax residency. Factors can include where you spend your time, where you’re registered to vote, your driver’s license, and other evidence of where you consider your permanent home.

You may have heard of the 183-day rule, but it isn’t a universal requirement for establishing domicile. Some states also have separate rules that can trigger tax residency even if you consider another state your permanent home.

Primary residences may qualify for property tax exemptions or benefits that aren’t available to second homes. And owning property in multiple states can create additional estate-planning considerations.

My advice? Talk to your CPA and estate-planning attorney before making decisions about changing residency or purchasing property in another state. It’s much easier to plan properly from the beginning.

4. Don’t Underestimate the Cost of Maintaining Multiple Homes

Owning two or three homes sounds wonderful until you’re managing two or three sets of bills, maintenance schedules, and unexpected repairs!

Beyond mortgage payments and property taxes, consider:

Insurance: Coastal properties in Florida and Delaware may require costly flood or wind coverage.
HOA and condo fees: These can simplify maintenance, but review reserves, planned projects, and potential special assessments.
Utilities and upkeep: Homes require maintenance even when you’re not there.
Property management: Who checks on the property or handles emergencies while you’re away?
Travel expenses: Frequent flights, driving, and maintaining vehicles in multiple locations can add up.

I’m a big believer in making life easier wherever possible, especially when the goal is to enjoy retirement.

Smart thermostats, water-leak detectors, and trusted local service providers can help. For some people, a well-managed condo is worth the monthly fee if it means being able to lock the door and leave without worrying about maintenance.

Just be sure you’re comparing the total cost of ownership, not simply the purchase prices.

5. Think About How Your Needs Might Change

One consideration that sometimes gets overlooked is how well each home will work for you five, ten, or even twenty years from now.

A three-story beach house might be perfect today, but will you still want all those stairs later? Is there a first-floor bedroom? Are healthcare providers nearby?

It’s also worth considering whether maintaining several properties will continue to feel exciting or eventually become more work than you want.

You don’t need to have every detail of retirement figured out today. But thinking ahead can help you make choices that give you more flexibility down the road.

6. Build a Team That Can Help You in Every Market

One of the benefits of working with our team is that our relationships extend well beyond the DC area.

Through Compass and our broader national and international network, we’ve built relationships with excellent agents in markets across the country and beyond.

Whether you’re considering a winter home in Florida, a beach house in Delaware, or somewhere completely different, we’d be happy to help you find the right person.

And you don’t have to be selling your home here to take advantage of those connections!

Looking for a great agent in another market? Let us connect you with someone we trust.

Of course, your CPA, financial advisor, and estate-planning attorney should also be part of the conversation so that your real estate decisions support your broader retirement plans.

The Goal Isn’t Necessarily More Homes. It’s a Better Lifestyle.

Ultimately, I think the most important question is this:

What do you want your retirement to look like?

Maybe it’s waking up near the ocean every morning. Maybe it’s having the flexibility to spend time with your grandchildren while escaping to warmer weather for a few months. Or maybe it’s finally living in that walkable neighborhood you’ve always loved.

Once you know what you’re working toward, it’s much easier to make thoughtful decisions about which properties to keep, sell, or buy.

If you’re starting to think about retirement, downsizing, or owning homes in multiple markets, I’d love to help you talk through the possibilities.

Sometimes the best first step isn’t looking at houses. It’s figuring out what you want your next chapter to look like. Get in touch with us today to learn more. Call us directly or send an email to allison@thegoodhartgroup.com to connect!