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Updated 9 months ago,

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3
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1
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David Ashworth
1
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3
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1031 exchanges / Tax deferment

David Ashworth
Posted

I hold land personally with my wife that I am selling and at the same time I am purchasing my first str. The str will close before the land sells and then I would like to recast the loan to pay off a portion with the land proceeds.  We are taking a cash out loan on my primary residence since the rate is over 1.25% lower. We will use proceeds from the str to pay the note but may be missing some tax benefits with this structure. 


- The land was homesteaded under the same parcel ID as our primary residence as it was next door and will be carved out at sale.
- We have lived in the house more than two years.  
- We will sell the land for about 2.5-3x what we paid.  
- The str will be purchased in an LLC

QUESTION: Is there a way to defer/avoid paying taxes on the gain since it's held personally as part of my primary residence and we have lived there greater than two years and the gain will be less than $500k or as a 1031 exchange investing into the STR LLC?

Thanks 

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