[villages07]

CT...

You can't claim a loss on sale of your CT home (as far as I know, and I'm not an accountant). Best the Feds let you do is not pay taxes on the gain.

While waiting for your CT home to sell....if you switch to FL residents.... you will be eligible for FL property tax homestead exemption which will lower your property taxes. This might only benefit you if it takes a long time to sell in CT. More importantly, by becoming a FL resident, you will not have any state income taxes that you would normally pay to CT. Again, talk to your accountant...different states have different tax laws on people with multiple homes.

One potential disadvantage.... if you have something akin to a homestead property tax exemption in CT, once you declare FL as primary...you may lose this exemption and now be taxed on the full value of your CT house.

As others have noted, it's very expensive to continue to maintain 2 houses....price CT to sell and be done with it sooner than later. Then, you reap the more intangible benefit of being able to live in TV in a much lower stress, happier environment.

Best advice is to talk to your accountant.