Capital Gains - Best ways to reduce

Capital Gains - Best ways to reduce

Member since 2024 · 3 posts · 4 votes

Hi There,

This is my first post so thank you to anyone that can provide feedback!

I recently bought my first residential property (a condo) in the burbs just north of Chicago. I bought it off market at a great deal with a conventional mortgage as a primary residence with the plans to rent it after the 12 month period has passed so I can legally rent it. I purchased the unit for 250K and I put about 25K into the place.

The rents in the area for these type of units go for around 3K, maybe a bit more, leaving me about $400+ a month in profit after the mortgage and HOA. This isn't including other expenses I know but I was planning to self manage the property and hope rates continue to go down so I could refi in the future and gain more margin in rental income.

After further analysis and speaking with a friend thats a real estate agent I may want to shift my original plan and sell it. They shared I could easily sell this unit for 400K+ leaving a sizable gain in the short term.

That being said I would face some significant capital gains and I was wondering if I had any options to avoid these. So I had a few questions to see if any of you had a similar experience and what you all have done/learned.

First, besides what I put into the unit (25K) is there anything else I can write off?

Is there a way to put this into a 1031 if its considered my Primary residence? Even if I 1031into an actual investment property?

Would you still hold if you had such a sizable opportunity? I feel the value of this condo is at its peak considering the market.

Are there any legal exceptions for the 121 home sales exclusion if I buy another primary residence shortly after the sale to avoid tax? I'ved owned this property for 6 months.

Am I missing anything here?

Thanks!

Dan

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Dave FosterBusiness Member
Qualified Intermediary for 1031 Exchanges · St. Petersburg, FL · Member since 2013 · 9k+ posts · 9k+ votes
2y

@Dan Stelmach, You can't 1031 your primary residence.  You could convert it into an investment property and then use it for investment for a year and then sell and 1031.  That would work.

But, if you've already invested a year in that as a primary residence then why not stay there one more year and take the gain tax free under sec 121 the primary residence exclusion.  Yes it takes another year.  But tax free is a pretty strong motivator.

Tax free if your primary.  Indefinitely tax deferred if you decide to use it as an investment.  Either way works pretty well.

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  • Real Estate Broker · Denver/Castle Pines/Colorado Springs, CO · Member since 2021 · 248 posts · 136 votes
    2y

    DId the agent show you comps showing 400k sales for similar units?

    I would consider a HELOC if you walked into that much equity. Live the two years there, then sell.

  • Member since 2024 · 3 posts · 4 votes
    2y

    They did provide a CMA.

    Thanks for sharing. I did consider a HELOC but felt it may stretch me to an uncomfortable financial position, all things considered. Then I'd be using borrowed money to pay down debt I could not afford with no cashflow from a rental.

  • Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
    2y
  • Real Estate Broker · 3412 S. Harlem Avenue Riverside, IL 60546 · Member since 2015 · 6k+ posts · 5k+ votes
    2y

    @Dan Stelmach first of all congratulations on your excellent investment. I would think carefully about selling versus doing a cash out refinance. The reason folks prefer not selling, is you avoid all the transaction costs..... why burn 6-8% of your profits if you can avoid it by holding onto the asset? 

    As an agent, I always want my clients to know what their properties are worth because (of course) I want to sell the properties, but I also like people to know the best tax strategies. 9 times out of 10, you are better off holding the property for a while to get increased appreciation, cash flow, better debt, more cash flow, etc. 

  • Dave FosterBusiness Member
    Qualified Intermediary for 1031 Exchanges · St. Petersburg, FL · Member since 2013 · 9k+ posts · 9k+ votes
    2y

    @Dan Stelmach, You can't 1031 your primary residence.  You could convert it into an investment property and then use it for investment for a year and then sell and 1031.  That would work.

    But, if you've already invested a year in that as a primary residence then why not stay there one more year and take the gain tax free under sec 121 the primary residence exclusion.  Yes it takes another year.  But tax free is a pretty strong motivator.

    Tax free if your primary.  Indefinitely tax deferred if you decide to use it as an investment.  Either way works pretty well.

    The 1031 Investor5137 Reviews
  • Investor · Las Vegas, NV · Member since 2013 · 8k+ posts · 10k+ votes
    2y

    As Dave “the expert” foster said. The ideal plan is live the one more year and sell tax free. (Assuming your realtor isn’t “blowing smoke”.). 

    This means saving at least $22k in federal income tax plus probably $10-$15k in state income tax. Being paid $30k to live in a house is a pretty good deal. Plus you can list it at 22 months and close in 24 months and a day. 

    Obviously this probably means the end of your real estate investing in that area if you don’t feel comfortable with the higher loan. The returns on a property that’s 50% more expensive isn’t going to worth it. 

  • Member since 2024 · 3 posts · 4 votes
    2y

    Thanks for the feedback and guidance @Dave Foster and @Bill B.. I will need to explore the 1031 route and weight it against my opinion on the market. The area I purchased in is great but I know condos valuations fluctuate more then other residential properties. 

    I also got a second relators opinion with and they provided a similar market value.

  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    2y

    @Dan Stelmach You can reduce your capital gains by writing off expenses like the $25K in improvements, closing costs, legal fees, and real estate commissions. However, since this is your primary residence, it doesn’t qualify for a 1031 exchange unless you convert it into a rental and hold it for a period before selling.

    To avoid capital gains taxes using the Section 121 exclusion, you’d need to have lived in the property for at least 2 years, which you haven’t met yet. If you sell because of health, work, job, or unforeseen circumstance you can get the section 121 even if you sell before 2 years. like you are selling for profit reasons. It looks

    Selling now would subject you to short-term capital gains, taxed at your ordinary income rate. If you can hold the property for over a year, it will qualify for long-term capital gains, which are taxed at a lower rate.

    Consider holding the property to qualify for either the long-term gains rate or the 121 exclusion. Look into REPS or STR to avoid paying taxes on the new gain if possible.

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  • Jonathan KlemmBusiness Member
    Moderator
    Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
    2y

    Hey @Dan Stelmach - Welcome to the Chicago BiggerPockets community and congrats on the condo purchase!  Sounds like you got a killer deal and added some instant equity...WELL DONE!

    If you are going to sell, I'd suggest waiting until after your first year to avoid the short-term capital gains tax.  

    Another great option would be to live there for 2 out of the next 5 years and pay NO CAPITAL GAINS. In the meantime, get a Home Equity Line of Credit (HELOC) with @Michael Barbari , who can do up to a 90% loan-to-value.  Use that money to invest before you sell the condo.

    The Chicago market isn't dropping anytime soon...inventory is still DRASTICALLY LOW and rates are still high.  If rates go down it's a win win win for you the value of your house will go up with more demand, you can refi, and it's better for your future investments.

  • Dave FosterBusiness Member
    Qualified Intermediary for 1031 Exchanges · St. Petersburg, FL · Member since 2013 · 9k+ posts · 9k+ votes
    2y

    @Dan Stelmach, glad it was helpful.  I just shot a colleague request to you if you have follow up questions.

    The 1031 Investor5137 Reviews
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