Plenty of Retirees Buy a Second Home for the Winters and Sell It Within Five Years. One Reason Comes Up Every Time
Buying a second home for winter warmth sounds like a clean retirement win, but the costs that stack up while nobody is living there have a way of turning that logic upside down.
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Many retired couples spend winters in a warmer state, often a couple of days’ drive south of their primary home. Some retired couples buy a second home to make that arrangement permanent, and some later sell it. This piece follows the reason that affects every one of those owners: what it costs, in money and work, to keep two houses running when one sits empty half the year.
What an Empty House Quietly Costs Each Year
Insurance is where it usually starts. Most homeowners policies cover an empty home for only 30 to 60 days, and only if the insurer knows. Some vacancy clauses limit or void coverage after 30 consecutive days. So a summer-empty winter home often needs seasonal or vacant-home coverage, and many owners also pay someone to walk through it, run the water, and check for leaks or storm damage.
Property taxes also work differently. In Florida, the homestead exemption can cut taxable value by up to $50,000, but only for a home that’s the owner’s permanent residence. That exemption qualifies a home for the Save Our Homes cap, which limits assessed value growth to 3% per year. A second home qualifies for neither benefit, which is important to consider.
Its assessment increases are capped at 10%, and that cap would drop to 5% beginning January 1, 2027 under a ballot measure going before voters on November 3, 2026. The measure needs 60% approval, and second homes would still be fully taxable. Then there are HOA fees, utilities that run year-round, and repairs that show up whether anyone’s there or not.
Turning That Cost Into a Portfolio Number
The average aged couple with both spouses collecting gets $3,208 a month after the 2027 COLA, or about $38,500 a year. Medicare Part B costs $202.90 a month per person, about $4,870 a year for two. The primary household already accounts for most of that income. The second house usually has to come out of the portfolio.
At 4%, each $10,000 in annual carrying costs requires about $250,000 in invested savings. A couple retiring early who want a safer 3.5% rate would need closer to $286,000. Large withdrawals can also push joint income past $218,000, where Part B surcharges begin.
Medicare, Residency and the Tax Bill at Sale
Any provider that takes Medicare accepts Original Medicare nationwide. Medicare Advantage plans are tied to a network. Some PPO plans pay out-of-network at a higher cost, and HMO plans may cover nothing outside emergencies away from home.
We dug into exactly this split-residency Medicare puzzle in a free guide on snowbird coverage, which you can grab here: Six Months in Florida, Six Months in Ohio.
State taxes can get complicated too. New York treats someone as a resident if they keep a permanent home there and spend more than 183 days in the state, regardless of where their legal residence is (N.Y. Tax Law § 605(b)(1)(B)). People changing legal residence often point to a Florida driver’s license, voter registration, and a recorded Declaration of Domicile.
Selling brings its own bill, as the home-sale exclusion of $250,000, or $500,000 for joint filers, only applies to a home owned and used as the principal residence for 2 of the 5 years before the sale. Gains on a second home are generally taxable, and agent commissions and closing costs come out of the proceeds too. Resales are running at 3.99 million a year, which sits in the “soft” range. Cape Coral-Fort Myers prices are down 0.9% over the past year, even after a 27.83% gain over five years.
Other factors can matter too, such as distance from family and friends back home, or one spouse liking the place more than the other. Upkeep on the second house also adds ongoing work.
Renting First and Picking a Home State
Renting in the same area for a few winters before buying is one way to test the neighborhood, the drive, and time away from family without a mortgage. Another step is adding up the full annual cost of owning both homes, including insurance on a house nobody’s living in. Which state is home also matters, because that one choice drives the homestead exemption, income tax residency, and which Medicare setup makes sense.
One relevant figure is what the second house costs in a year when nobody’s living in it. That means taxes without a homestead break, seasonal insurance, HOA dues, utilities, someone to check on the place, and a repair reserve. At 4%, that total is about 25 times the savings, or about 29 times at 3.5%. The result is extra portfolio capital on top of whatever already pays for the primary home. Renting for the winter avoids carrying costs during the empty months.
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David Beren has been a Flywheel Publishing contributor since 2022. Writing for 24/7 Wall St. since 2023, David loves to write about topics of all shapes and sizes. As a technology expert, David focuses heavily on consumer electronics brands, automobiles, and general technology. He has previously written for LifeWire, formerly About.com. As a part-time freelance writer, David’s “day job” has been working on and leading social media for multiple Fortune 100 brands. David loves the flexibility of this field and its ability to reach customers exactly where they like to spend their time. Additionally, David previously published his own blog, TmoNews.com, which reached 3 million readers in its first year. In addition to freelance and social media work, David loves to spend time with his family and children and relive the glory days of video game consoles by playing any retro game console he can get his hands on.
