Downsizing, or moving to assisted living

Should I sell before or after I move?

Selling first gives you certainty and a known number, but means moving twice or negotiating a rent-back. Selling after gives you one move but means carrying both properties for a median 46 days if priced correctly, and potentially 117 or more if not. Which is right depends on whether you can comfortably carry both.

The version that goes wrong most often is moving first without being honest about the carrying cost. A month of two mortgages, two insurance policies, two sets of utilities, plus the amenity fee and the bond on the old place, is survivable. Five months of it changes how you negotiate, and buyers can tell.

How long should I plan for?

Homes that sold in 2026 took a median 46 days from listing. Villas moved in a median 46 days and single family homes in 44. Build the timeline from those figures plus roughly 30 to 45 days from contract to closing, and add margin, because 22 percent of listings did not sell at all.

So a realistic plan for a correctly priced home is roughly three months from listing to keys, not six weeks. If your assisted living move has a fixed date, work backward from it with that in mind and start the preparation earlier than feels necessary.

Source: Stellar MLS residential listings inside The Villages, compiled by Cristian Gonzalez, eXp Realty, pulled September 21, 2026. Current-market figures cover the trailing window from May 4, 2026; listing-outcome figures cover January 1 to September 21 and exclude ZIP 32162, whose sold data starts in May. Information deemed reliable but not guaranteed. Updated September 2026.

Is downsizing to a villa worth it?

Financially the gap is smaller than people expect. In 2026 villas sold at a median $243 per square foot against $241 for single family homes. A villa costs less in total because it is smaller, not because the square footage is worth less. The real saving is in maintenance, yard work, and carrying cost.

The median gap between the two is about $95,000. Whether that plus lower upkeep is worth the space you give up is a personal question, but at least it is now a question with a number attached. More on how the types compare.

Do not forget the bond on the way out

If you are selling one Villages home and buying another, you are dealing with the bond on both sides. The home you are selling has a balance that affects what buyers will pay, and the home you are buying has one that affects what you should offer. Villages-to-Villages moves are the transactions where this gets overlooked most, because people assume it washes out. It usually does not, especially moving from an older section to a newer one where the bond is larger. The bond and your sale covers the selling side; the main bond page covers the buying side.

If the move is to assisted living

A few things worth knowing, none of which are advice:

• Timing may not be yours to control. If a placement comes available, it comes available. Having the comparables and carrying cost already in hand means you can decide in a day instead of a month.
• Who signs matters. If a power of attorney is involved, confirm with an attorney that it is adequate for a real estate transaction. Some are not, and finding out at title is a bad time.
• Medicaid planning has rules about asset transfers that an elder law attorney should address before you sell, not after. This genuinely matters and it is genuinely not something a real estate agent should be talking about.
• The house does not need renovating. Clear, clean, repair the obvious, photograph properly. That is the return-on-effort work. A kitchen remodel at this stage rarely pays back.

Nothing on this page is legal, tax, or financial advice, and I am not a lawyer, a CPA, or a financial advisor. Probate procedure, title, homestead status, and tax treatment are questions for a Florida attorney and your CPA. What I can do is the real estate work and tell you which questions to put in front of them.