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  • Capital Gains Tax When Selling Your Key West Vacation Home,Jimmy Lane

    Capital Gains Tax When Selling Your Key West Vacation Home

    Do you owe capital gains tax when selling a Key West vacation home? Yes. If you're selling a Key West home you've used as a vacation property or second home — not your primary residence — you owe federal capital gains tax on your full profit. The $250,000 exclusion ($500,000 for married couples) onl

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  • Should you sell your Key West home now or wait?,Jimmy Lane

    Should you sell your Key West home now or wait?

    Should you sell your Key West home now or wait? Whether to sell now depends on your timeline, your equity position, and your price expectations. The Key West market has shifted meaningfully in 2026 — inventory is at 12 months, homes are averaging over 100 days on market, and sellers are accepting ab

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  • How Much Does It Cost to Sell a House in Key West, Florida?,Jimmy Lane

    How Much Does It Cost to Sell a House in Key West, Florida?

    This is the question I get more than almost any other from sellers who are seriously thinking about listing. The honest answer is: more than you might expect — especially in Key West, where the transaction costs carry some line items you won't see on a mainland Florida net sheet. Let me walk you thr

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