Downsizing and 55+ moves
DOWNSIZING OR
MOVING TO A COMMUNITY
Selling the house in Venice or Englewood and moving to a villa, a 55+ community, or closer to family up north. The hard part is rarely the price — it is the order of operations.
Short answer
The goal is to never own two homes and never be homeless in between. In practice that means selling with a closing date you choose and a leaseback if you need weeks, not a rushed move.
A cash offer is useful here even if you end up listing: it gives you a guaranteed floor and a date, which is exactly what makes an offer on the next place credible.
The sequencing problem, solved three ways
- Sell first, rent back. Close, take the money, and stay in the home for an agreed period while you move. Cleanest option for most downsizers.
- Buy first with a contingency. Works when the next purchase is not competitive, and when your equity supports it.
- Cash offer with a chosen closing date. Pick the date, keep the certainty, skip the showings.
Two Florida numbers worth knowing
Homestead portability. Florida lets homesteaded owners transfer up to $500,000 of accumulated Save Our Homes assessment benefit to a new Florida homestead, which can cut the tax bill on the next house substantially. There is a filing deadline, and it applies within Florida only.
The capital gains exclusion. The old "over 55, one time" rule no longer exists. Today's rule generally excludes up to $250,000 of gain (single) or $500,000 (married filing jointly) on a primary residence owned and lived in for two of the last five years, with no age requirement. Confirm the details with your CPA.
Selling a home you have owned for twenty years
Long-held homes almost always show dated finishes and deferred maintenance, and almost always have far more equity than the owner expects. Do not spend $40,000 renovating on the way out until you have seen both numbers: what it brings updated, and what it brings as-is. Frequently the gap is smaller than the renovation.
We will value it both ways and be straightforward about which projects this market actually pays for.
Questions sellers actually ask
Can I stay in the house after closing?
Often yes. A post-closing occupancy agreement or leaseback of a few days to a few weeks is common, especially on a cash purchase.
Should I renovate before selling?
Usually not fully. Paint, landscaping and a clean roof and AC report earn their money back here; kitchen remodels typically do not.
Do I lose my low property taxes when I move?
Not entirely within Florida. Homestead portability can carry a large share of your Save Our Homes benefit to your next Florida homestead if you file on time.
What do I do with the furniture?
On a cash sale, leave what you do not want. On a listed sale we stage what helps and coordinate a haul-off for the rest.
Tell us the situation, we will tell you the options
One conversation, two numbers: what a cash offer looks like and what the open market should bring. No obligation either way.