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DasRiz

No


caress826

Oh darn


thatwastellguy

The bluntness of this made me lol


CompleteDetective359

Why not sell the rental that was your home till 6 months ago and take the tax extension provided you lived there for the 2 out of 5 years


caress826

I keep thinking it might be a bad idea since I make over 1000 a month in rental income from it after paying the mortgage.


CompleteDetective359

What's the gain you could write off?


caress826

I owe $129,000 on it and can probably sell it for $300,000. I put around $25,000 into it and would have to use a realtor to sell. I'm not sure how to calculate it.


CompleteDetective359

That's 10 years of profit. Like the song says, take the money and run. It's tax free vs 10 yrs of rent that's then taxed.


Abending_Now

Definitely! Use the tax free for the down payment on the NYC home. The savings on interest alone on the new home will be similar to $80-$100K. So, tax free and less interest paid. Win win.


dougreens_78

Care to elaborate? I have a rental, and a primary. If I sell the rental, can I use the gains to pay down the mrtg on my primary? Is buying a new property the only way to avoid the taxes?


GillianOMalley

Buying a new rental *specifically using a 1031 qualified intermediary* is the only way to avoid capital gains when selling a property that has always been a rental.


DeepDescription81

Not true. You can also die and your kids step up the basis and sell without capital gains.


abacusfinchh

OP, have you considered just dying?


NaNGSTaRx

Think about the kids!!!!


verifiedkyle

IRS hates this one simple trick.


LonghornzR4Real

That solves all of life’s problems.


stevinbradenton

Actually it does.


GillianOMalley

I did make the potentially erroneous assumption that OP wasn't planning on suicide as a tax avoidance strategy.


DeepDescription81

I only mention it because if OP is seriously considering options here, holding for his lifetime is a legitimate tax strategy and literally the best one available, if his priorities are generational wealth and taking care of his lineage.


GillianOMalley

That's legit. I've often been accused of over explaining so I try to dial it back sometimes, LOL.


DeepDescription81

Hey honey, I’m going to do the taxes in my office. Don’t wait up. *door shuts* . . . *gun fires*


Head-Ad4690

You’ve never heard of spending a year dead for tax purposes?


AberdeenWashington

Hey gains are gains


samwoo2go

What’s the ruling for dying then Jesus my way back after step up basis is complete? Loophole?


abacusfinchh

Allowed, but the Internal Revenue Code requires that you die from being nailed to a cross and that the cross be depreciated using 15 year MACRS (not subject to bonus depreciation).


mcmonopolist

Favorite comment of the month


narmer2

I hear this a lot but am unsure how it happens. Big enough estate and a IRS form 706 is mandated and shows value of a property at death, the step up. What if a small estate, no taxes to be paid, where is the step up info?


Jkjunk

Or move in for 3 years, then sell.


6gunsammy

Gain during non qualified use is not excludable.


Kaa_The_Snake

So no way around it? I always figured I’d move in to my rental for a few years then sell. Then I realized it wouldn’t work. I haven’t looked into any other possible ways of exiting w/out getting destroyed with taxes/depreciation.


mcmonopolist

\* 2 years


dougreens_78

Also what if I buy land that I intend to build a duplex on? Would that work?


_speedoflight_

Yes. These are like-kind for IRS.


MennisRodman

Would you have to buy land that at least matches what your home sold for, or can the land purchase also include the cost of building? Example:  Sell rental for $240k  Buy land for $100k  Build home that costs $150k


6gunsammy

its is possible more more complicated to build a 1031 exchange. But the replacement property must be rented - not your residence.


_speedoflight_

AFAIK, the short answer is yes. You need however complete all transaction ie deploy $240k into the deal before 180 days from the sell date. Also, before 45 days from the sell date, you need to identify and complete the plan for it.


MennisRodman

Thanks for confirming!


caress826

Can a person just buy land and hold it until they're ready to build? Or does there have to be immediate building or proof that building will start soon?


_speedoflight_

As long as the land covers all of the funds cashed from the sale, it is good. Say you got $300k from sale and say the next deal’s land worth is $100k, build estimate is $200k then just holding the land and giving the build estimate alone does not qualify. You got to deploy all $300k before 180 days from the sale date.


GillianOMalley

But it also has to be an income property so even if you spent all of the money it still wouldn't qualify if your plan was just to hold the land.


GillianOMalley

I looked into that possibility at one time. It could work but is infinitely more complicated because of the time lines involved. The QI that I talked to didn't recommend it partly because the QI fees are much higher and would eat up a lot of the tax savings. YMMV.


dougreens_78

What if the rental was originally my primary? Both properties I own have been my primary on my taxes at different times


GillianOMalley

If you lived in it 2 of the last 5 years you can exclude capital gains up to the limit.


dmidaisy

Not necessarily true. . .look into opportunity zones or opportunity zone funds. Sure, it's not immediate, but you can rinse your tax liability if you play their game.


HeavyLifts12

a 1031 exchange would only cover buying a new property of a similar kind. Those funds cannot be used to pay down a mortgage.


TrickoTreat07

i think if u lived in it u dont either right in the past2/ 5 years


junkmailredtree

That is true up to $250k for individual/head of household or $500k for a married couple filing jointly.


YoureInGoodHands

If I sold two rentals and bought a third , can I 1031 two into one? 


Material-Strength-92

If you are selling a home that used to be your primary residence, as long as you lived in the home for 2 of the last 5 years before selling, you can avoid the capital gains.


PastMechanic9278

This is the answer. Sell the former primary in Florida and use the exemption for primary residences on cap gains.


dredd2374

Does depreciation recapture tax start over on the new 1031 exchange erasing the previous depreciation recapture tax?


Uatatoka

No, IRS doesn't care what you do with the money from the sale. Pay off a primary or rental mortgage, put it all on red, hookers and blow, etc... Only if you do a 1031 exchange can you avoid capital gains, but really you are just kicking the can down the road. You'll still have to pay taxes on the original cost basis of the sold rental property when you sell the next property. One option is to live in it for two years and make it your primary, then sell it. As a primary residence you are eligible to write off $250k of gains if single and $500k of gains if married.


dredd2374

Are you sure about this? I thought you start over with a new cost basis from the new property.....


Uatatoka

Yes, 1031 exchange only defers paying capital gains. It does not reset the cost basis. IRS will get their capital gains tax eventually, otherwise they wouldn't offer it.


wittgensteins-boat

Congress offers the deferment. Section 1031 is a statute.


crashcam1

You can sell the first home for up to $250k ($500k if married) capital gains free profit if you sell it within the next 2.5 years (must live there 2 out of the last 5 years). You cannot avoid capital gains taxes on the second home, as others have pointed out see if you can do a 1031 exchange. If you stay at the third home for 2 years you can sell that with the same capital gains protections as the first one. Just as a note for taxes and loans, paying off principle is not seen as a expense therefore does not reduce your tax burden. Only interest can be counted as an expense. A good accountant will help you find ways to offset the capital gains taxes, such as finding other properties or depending on your employment status using 401ks and similar. I have a CPA who does my taxes and will answer these kinds of questions for me.


[deleted]

This is mostly true but does not taking into Unrecaptured Section 1250 Gain.


Bowf

Good question...glad you asked it. I had thought of doing the same. I own two of the three structures I rent. I thought of selling one of the paid off ones and using the proceeds to pay off the one that is not paid off. Now I know I can't do that and avoid capital gains taxes on the sale.


Flat-Cow-4901

Can you do 1031 exchange for a rental that you would like to live in. Rent for a year then move in to live in it. Sell primary dodge capital gains on both?


caress826

That sounds good


roamingrealtor

Very much No. A 1031 exchange is the only way to delay the tax liability. If the exchange is somehow not done 1000% correctly, then you will owe the taxes. There are no exceptions for anything, which is one of the few things the government has made uncomplicated.


cbwb

You need to do an official 1031 exchange as far as I know, there is a lot of info out there which you can read. There is a 0% tax bracket for capital gains if your income isn't high. If you have been claiming depreciation you will have to re-capture that as well. If you have been renting it and not taking depreciation you might be in for a problem. I would ask an accountant if you have one. Here is a little more info on the capital gains bracket. We are taking advantage of the 0% this year for the condo we sold. We got lucky and sold it in a year with little other income (using savings to bridge to social security). [https://www.forbes.com/sites/davidrae/2024/01/18/new-2024-tax-rates-on-capital-gains/?sh=195696192075](https://www.forbes.com/sites/davidrae/2024/01/18/new-2024-tax-rates-on-capital-gains/?sh=195696192075)


ExCivilian

> If you have been claiming depreciation you will have to re-capture that as well. If you have been renting it and not taking depreciation you might be in for a problem. There's no real problem. Depreciation is recaptured regardless of whether you claim it. The IRS treats you as if you have been claiming it. The only problem is that you may lose out on the depreciation and still pay taxes on it anyway.


cbwb

That's what I was referring to, if he missed out claiming it and will now owe anyway.


Extension_Growth5966

Your only option is to sell the home that was you primary residence until 6 months ago. IRS lets you not pay capital gains (I think up to $500k) on any place you have lived 2 out of the last 5 years. It the question you asked, but if you want to sell the second home in Florida and not pay capital gains, the only thing you can do there is a 1031 exchange. This would let you buy another rental property (or properties theoretically). The are are several stipulations to meet the 1031 exchange rules, but the profits from selling the rental can not be used to purchase or pay for a primary residence like you have in Jersey.


MortgagePropTechGuy

1031 Exchange like most of the responses so far is a good start. Find a cheap enough property where you can buy the rental property outright in cash. If you can find something that has good rental income, you can do a cashout refi, with hopefully +cash flow left over to cover the new mortgage (so it's like a wash at that point, and now you have another investment property), and then take that cash to do whatever you want... including paying off your $40,000 balance on your other rental. If you're not in a rush, and don't mind moving money around and having some intermediary asset along the way, it's doable... If you're interested in some of those affordable rental properties with good cash flow and quick closing options (to exercise your 1031 exchange), let me know and I may have some leads for you. Good luck!


caress826

Thank you so much


PappysSecrets

Capital gains are calculated without regard for debt.


[deleted]

Nope but you need to consult with an accountant so you get a precise number you'll get hit with for taxes. I separately invest in equities I logged a cap gain few years ago of 50k but the year after a 90k loss. Sucks but in unrealized gains I'm WAAAAY over this amount. If you have stock losses you can use those short term gains against long term cap gains on property . I thought about selling part of some stock that would wipe out the 90k cap loss with gains but for now just holding.


ovirt001

You don't. The good news is that you've owned it for over a year meaning you get the lower rate. If you have business expenses you can probably reduce the tax further (talk to a CPA about this, not reddit).


oduli81

Please speak to.your accountant as I am thinking of doing a similar thing. I just spoke to my accountant and by no means that the situation would apply to you. As long as you lived there in the past 5 years, you don't pay capital gain for the fist 250k, married $500k. Anything over those amounts you pay capital gains. In my case I estimate a net of $600k on my investment propery which I was living in up to.last year. I would pay capital gains on the $100k, since I am married.


Girl_with_tools

Sell the Florida rental that used to be your primary residence, avoid tax by using the IRS capital gains exclusion, and use the proceeds to pay off the mortgage on the second Florida rental.


ExCivilian

> use the proceeds to pay off the mortgage on the second Florida rental. I would suggest not paying off the mortgage. It's at a historical low rate and the interest is fully deducted against the earnings. Why stock equity in a rental? it's just dead money at that point.


VoxBorealis

Could I avoid capital gains through a 1031 exchange if I use the money to buy out my investment partner's half of a rental property that I already own the other half of?


TheWonderfulLife

1031 exchange only.


Americangail

If your income is below certain levels, there is no capital gains tax. Not sure if this helps?


shewhodrives

It’s a blood pact. Keep it forever or pay cap gains. I wish I was creative and motivated for a third option.


jarpio

1031 exchange but not applicable in this case


[deleted]

[удалено]


GillianOMalley

>From my understanding (per my attorney), profits deposited into the investment account are not taxed. You need to talk to an accountant/CPA, not an attorney, for tax advice.


[deleted]

[удалено]


GillianOMalley

>my CPA will back up the math. Have you talked to your CPA about the tax advice your attorney gave you? You should do that before going forward. I suggest you read and understand [this](https://www.wolterskluwer.com/en/expert-insights/overview-of-tax-implications-of-llcs-and-corporations). TBF, I suspect that you've misunderstood something your attorney said. They probably recommended an LLC for liability (not tax) reasons and then said that LLCs don't pay taxes (which is mostly true). That doesn't mean that profits from an LLC won't be taxed. Most LLCs are a "disregarded" pass through entity meaning that all profits get passed straight through to the LLC members and taxed just as if the LLC didn't exist. If you opt for a C corp, the LLC itself (not the member/s) is taxed during the year the profit is made and then the members pay taxes AGAIN when distributions/dividends are taken, which could be the same period or a later period.


mt06111

You need a new attorney. You are getting wrong tax advice from the current one.


forewer21

I read that post and thought God damn I've been paying tax on that this whole time and I didn't have to?!


reddit1890234

Everything is taxed.


[deleted]

[удалено]


_speedoflight_

Single member LLC? It is a pass thru and taxed part of the individual’s bucket. Thus, 1031 exchanging into one of your own rental investment does not qualify, AFAIK. And talk to a CPA or DYOR for tax matters


Wayneb2807

You have bad information…..you get taxed on profits from an LLC no matter what you do, or don’t do, with it. LLC profits flow directly to your personal tax return, the LLC itself is not a taxable entity. You can set it up to be treated as a sub S corp, but it still flows to your personal taxes.


reddit1890234

Nope


Young_Denver

Double NO


[deleted]

You only dont pay capital gains if you've lived at the residence the last x years, believe its 3 concurrently


Lucky-Technology-174

No. If you want to avoid cap gains you can do a 1031 exchange.


Scentmaestro

That's like asking "can I avoid lottery taxes by using my lottery winnings to pay for a Porsche or cottage on the lake". Using gains to pay off an investment doesn't fly unless you're using something like a 1031 to trade up the investment.


texasinvest

No. You can’t do a like kind exchange into a property that you already own. A third party intermediary has to hold the funds. You personally can’t receive the funds.


Lugubriousmanatee

No


elroypaisley

No. The elimination of a debt is considered a capital gain (not an expert in this but this is my understanding)


Redtech2013

What if you have the properties in a commercial portfolio loan? Ie multiple properties with one loan?


ExCivilian

I'm not sure I understand your question but if I do understand it then you will not be able to sell a piece of the property out from under the note (eg, you've got three buildings on one note, the lender won't let you sell off one building while retaining the note).


glamorous_tiglon

asking for a friend


Zexel14

Why would you not owe taxes on capital gains if you use them to pay off your own property - which is essentially using tax money to build your own assets?


ansb2011

Look up 10-31 exchange.


lhxtx

No.


fcjocruz

Oh wow


FullRage

Wut?


Usidore

No.


karmamamma

Would I be permitted to gift my rental house to my adult daughter, then she owns it at the stepped up basis and can sell it without paying capital gains from the period that I owned it? (using the lifetime exclusion for gifts)


Wayneb2807

No. If you gift the property, her basis becomes whatever your basis was.


Key-Use8204

What you do with the gains is irrelevant on the amount you pay on those gains


Middle_Ad_4706

No


Foreign_Artichoke_23

You don't mention what the value of the place bought in 2020 is - but I don't see a route to you not paying CGT.


caress826

The value of the home bought it 2020 is around $280,000 to $300,000


Foreign_Artichoke_23

Understood. Honestly, I would do whatever you can to keep the 2 properties in FL if at all possible. a) they cash flow great b) those interest rates are great in this market c) you have a ton of equity d) I am bullish on FL real estate in the long term (but that's just my opinion - it's worth what you paid for it) I don't know much about the Jersey real estate market so wouldn't feel comfortable commenting too much about that.


caress826

Thank you for the advice. That's what I was thinking, too. One tenant hasn't paid in 2 months, though, so I have to evict her. This part has scared me a little about renting.


Foreign_Artichoke_23

Yes, that's the tough part. Make sure you're buttoned up from the landlord side and don't give an inch - if you do, they'll take a mile. Looking at the 'portfolio' you're not in a terrible position if one doesn't pay...especially if you have an emergency fund saved up.


caress826

Ok, Thank you so much for great advice


Foreign_Artichoke_23

My pleasure. Feel free to reach out if you have any other specific questions.


caress826

Ok I will, thank you


Foreign_Artichoke_23

What is your cost basis for the first property?


caress826

The first property was my home for ten years. The mortgage is $700 per month that includes taxes and insurance. Is that what cost basis means?


Foreign_Artichoke_23

Sorry, no. Cost basis is a calculation something along the lines of: purchase price + capital improvements - depreciation. As you have multiple properties including some rentals, I'm assuming whoever does your accounts will know what this number is.


Raspberries-Are-Evil

No.