Plan to Sell Your Primary Residence? STOP… And Consider This First.

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As a real estate agent for close to 30 years, I realized early on that many people make their biggest mistakes with real estate between the ages of 25 to 35 years old. Our working years really take place between 25 and 65 years old, and I believe the decisions we make in the beginning towards home ownership often dictate our future financial outcome as we sprint forward towards retirement.

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What Happened to My Down Payment & Closing Costs?

If you think about it, most young people first try to rent as much property as possible, and then they try to buy as much property as possible. Is it the overachiever in each of us, or are we just trying to impress our family and friends? Maybe we simply feel we deserve it.

Next, we often listen to our real estate agent when it comes time to moving up to our next home. They may encourage you to sell the first home, saying that you can’t afford two mortgages, but they may be squeezing you into as much home as possible on the next purchase. After all, we all have to keep up with the Joneses. Keep in mind, most real estate agents aren’t accountants or financial advisors.

Related: How to Create a Diversified (Yet Still Manageable) Real Estate Portfolio

If things are going well for a nice couple, after they’re in their second or third home, their accountant might tell them it’s time for a rental property or a beach home. The accountant might say that they could use more write-offs; they’re making too much earned income, and they could use more deductions.

But what’s really wrong with this picture? Do you see where the real estate mistakes were made early on?

Against the Herd – A Different Approach

Let’s say you took a different approach, like I did when I was young. I didn’t even realize what I was doing until much later, and I majored in accounting in school. I took a more conservative approach after graduation.

First, I lived at home for two years to save up some money. Then I rented the most affordable apartment I could so I can save more money for my first house. I didn’t really care what my friends or family thought; I was on a mission, and time was of the essence.

Then I bought my first duplex, owner-occupied, and it needed fixing up. But here’s the real difference: When it was time to move to the next property, I kept it. There were no stressful moving days for me. And guess what I did when I moved the next two times? I kept them as rentals, too. Now, let’s look at the real impact of doing that.

Advantages of Keeping Your Primary Residences

First of all, I had lower down payments and more favorable interest rates because I purchased these homes owner-occupied. I also purchased properties, which I could rent out for more than my mortgage payment. So now, I never really lost my down payment and closing costs because I kept them all. Most people forget about this real money that they spent to acquire a home. Seems like they just look at the monthly payment, much like they do when buying a car.

Another thing that’s overlooked is the time spent in the property, paying towards a 30 year mortgage before it becomes a rental. My first property I lived in for five years, my second property was two years, and my third property was 13 years. That was 13 years of payments towards my 30 year loan. Today, my mortgage payments are mostly principal, and my tenants are buying them for me.

Related: 3 Negatively Cashflowing “Assets” That Devastate 20-Somethings’ Finances

Sure, it took a little more time to save money between moving up with my primary residences, but it was well worth the wait. My properties enabled me to build additional wealth, and they’re almost paid off now. They not only give me depreciation and write-offs to offset earned income, but they can pay for things like college and weddings, and they provide a nice, passive cash flow in retirement.

As you can see, this has been one of the best investing strategies that I’ve taken in my entire life. It makes you wonder why this strategy is not taught more or is not more popular with young people starting out.

So, let me ask you, “Was selling your primary residence a mistake?”

Let me know your thoughts with a comment!

About Author

Dave Van Horn

Dave Van Horn is President at PPR The Note Co. - an operating entity that manages several funds that buy/sell/hold residential mortgages, both performing and delinquent. Dave has been in the Real Estate business for over 25 years, starting out as a Realtor and contractor and moving onto everything from fix and flips to Raising Private Money.


  1. Scott Trench

    I love this. This is exactly my plan. I purchased my duplex back in November of 2014, and after a year is up I’ll be able to do the exact same thing as you, as soon as a great deal is available. I’m hoping to repeat this strategy every 12-18 months and keep acquiring great passive rentals.

    I’m already experiencing the benefits of living this way in the form of appreciation, passive cash flow, no monthly rent or mortgage payment, and I’m just now opening my eyes to the incredible tax savings available to those who live in this manner.

    • Nathan Richmond

      Here’s my concern that I’m already having trouble with. What happens when the underwriters of these loans start to question why you are buying similar sized owner occupied homes in the same general area. They don’t seem to like to lend to those of us trying to do the rinse and repeat house hacking method. Has anyone found good ways around such underwriters?

  2. Sometimes it is just dumb luck. We purchased our primary residence n 1967. In the mid 1970s I wanted to move up, with our increase in value. Spouse did not agree…OK 1000sf was easy to clean and pay for. Long story short when we retired in 2001 , we didnt sell, but gifted it to our eldest daughter. This kept the original tax base (Calif Prop 13) and now it is her primary residence. We moved 1 hour away where the homes are affordable, and new. Real Estate is a good thing, Dave.

  3. Cory Binsfield

    This article was so good I’m sending it to all my milli ISO clients.

    When I first started out as a financial advisor in San Francisco, I was cold calling V.P.s and stumbled upon a guy who owned 10 houses across the country.

    I asked him how on earth did he end up with 10 houses? He told me every time he got relocated by his company he would keep his home and convert it to a rental.

    Bottom line, his motto was never sell and let the magic of rents pay off his mortgages.

    Oh…he was for classic millionaire next door due to this strategy.

    I took this advice to heart and tried it myself.

    Today, I still own 4 outta 5 of my original residences (I lost one to a divorce).

    This coupled with always recycling my earnings into equity has allowed me to build a nice real estate portfolio.

  4. Justin Baker

    Great ideas and I agree a ton, but feel like more information is needed. Such as looking at spreads on the payment vs. rental amount, additional risk on thin margins if purchased as an owner occ vs. income property (me!), etc. As a whole I totally agree, but would be curious to hear thoughts on thin margins….

    • Dave Van Horn

      Hi Justin,

      My advice would be to try and avoid buying a property with a thin margin between the mortgage payment and the rental price.

      As far as risk goes, It depends on how long you live in the property. A thin margin is not as much of a risk on an owner occupied deal because if you were to live there for 3 to 5 years, you’re mortgage payment would most likely stay the same but rent for the same property would probably go up.


  5. Brandon Hall

    Hey Dave,

    I like the strategy as it’s a great way to acquire property on the cheap. However I’m surprised you didn’t caution folks out there who are in the appreciation markets and warn them about what happens when you live in a property for two years, rent it out, then don’t sell it within three years.

    When you convert your property to a rental, your basis is the lesser of: (1) original cost plus improvements; or (2) fair market value. So if you convert a primary residence to a rental, and that property has appreciated significantly, you don’t get to write off a higher amount of depreciation *unless* you sell the property and cover $250k ($500 if MFJ) in capital gains and then roll the proceeds into a new property (not a 1031, just a straight purchase). Now you have a higher basis and likely a better property (or two or three).

    The key here is protecting your gains. If you hold the properties for an extended period of time, your cap gains exclusion dissolves. In a non-appreciative market, this won’t really matter. However in places like San Fran, NYC, DC, etc., covering your capital gains will make a HUGE difference in the long run.

    For the record, I plan to utilize your strategy to the fullest. But if I buy a primary in DC that appreciates significantly over my hold period, I’d be hard pressed to hold it and not shelter my capital gains.

    Good article!

    • Nate T.

      I wish I had sold my primary residence in 2005 to take advantage of the 250k exemption. Instead I kept it as a rental. I still have it. And the value still hasn’t recovered back to what it was in 2005.

      BUT, I couldn’t have sold it in 2005 and bought a “better” property. Because the whole market was appreciating. I would have had to either hold onto the cash, or invest in a non appreciating market out off state, which I definitely wasn’t ready for at that time. So it’s not quite as easy as it might sound.

    • Gautam Venkatesan

      Hi Brandon,

      Could you please clarify something for me? If you live in your primary residence for 2 yrs, then convert it to a rental for 3 yrs but still end up selling the property within the 5 yr time frame for less than $250K single/$500K married in capital gains would the gains (I understand cost basis would be different) be tax free and you also got to deduct depreciation for the 3 yrs the property was a rental or would there be depreciation recapture at 25%?

      • Jessie Huffey

        Hi Guatam,
        Great question – I dealt with this issue when we sold our home a few years ago. The tax law has been modified so that the IRS may collect capital gains on rentals for a portion of time that were also primary residences for over two years. Here is what happened in my case: We bought the home as a primary residence in 2008 for 350k. We lived in the home for 4 years. We then rented it out for 1 year. I lived in it again for a couple of months while fixing it up and preparing it to put on the market in 2014. It sold for 500k. Because we had rented the property for 1 of the 6 years we owned it, 1/6th of the gain (150k) was taxable so we had to pay 24k in capital gains tax.

    • Dan Clark

      This is a great point to bring up, but there is a counter to this. Don’t sell the property.

      Keep it, enjoy the appreciation, rental income, and depreciation for tax purposes, and then pass it on to your heirs. They will get a stepped-up basis in the property, wiping out the gains (for tax purposes). This is, and always has been my stategy. Whatever you buy, keep it forever! If you eventually want cash out of the property you can always do a cash-out refi.

      • Katie Rogers

        It seems because a cash-out refi puts the property back under a mortgage, you end up reducing your cash flow on the property along with everything else a mortgage entails. (Of course, I suppose you could do what a number of people in my town did. They did cash-out refis or helocs, then abandoned the property, having effectively sold it to the bank for top dollar. Seven years later, they are looking to buy again).

  6. George Smith

    That’s exactly what I’m in the middle of right now. It’s amazing how much money you’re throwing away after buying your first property and then selling it in the first 7-8 years. That is assuming you’re not in a highly appreciating cycle.

  7. Fallon Pollard

    I think this is an excellent strategy, we have encouraged one of our sons who is an entrepreneur at 17, to do this; he still lives at home, of course, and is saving to buy his first house. My husband and I are a little late to the game of turning our primary residence to a rental. We are actually in the middle of it now. We had our house on the market for sale, but it got a ton of attention from potential tenants; it is unique in our area, with a lot of features most rentals don’t have. Which helps in another area- we priced ourselves out of the neighborhood, over doing upgrades, simply because we never planned on moving. Our house will rent for more than enough to cover this mortgage and our new house, I can’t believe we didn’t consider it before.

    • Dave Van Horn

      Hi Fallon,
      I’m glad to hear that your property will cash flow and help to cover your expenses. Also, I think it’s really great that you and your husband are teaching this strategy to your kids.
      Best of luck to your son!

  8. Dean Suzuki

    Great post. This is how we got started unknowingly in real estate investing back in 2008.

    Hi Dave,
    Do you think that this applies to rental properties as well? I am thinking of either selling one of my rentals to raise capital for another investment which has a higher return OR doing a cash out refinance to pull cash out and invest to a lesser extent in the other investment. I’m wondering if its best to keep acquiring rental properties and never sell if the properties are cash flow positive.

  9. David Faulkner

    I did the same thing … it takes awhile, but it really works! A few additional benefits not mentioned:
    1)Minimal real estate transaction costs. It is relatively inexpensive to buy real estate, but transaction costs are very high on the sell side …if you want to sell you will be hit with 6% agent fees, capital gains, title insurance, etc. That is all lost equity to the seller, and it can be 10s of thousands of dollars or more.
    2)If you sell, you normally need to buy into the same market. So, if you sell high, you have to buy high … if you buy low, you usually had to sell low first. On the other hand, if you don’t sell, then you can take maximum advantage of the market by being patient and buying if and only when the market gives you great deals.

    The 2 benefits above, plus the ones already mentioned, repeated a few times adds up to a lot of $!

  10. Shailesh L.

    I got into this strategy unknowing last year when I relocated to take up new job. I didn’t get reasonable offers when I put my SFR on market so I ended up converting it into rental. It turned out to be much better than I thought. I also bought SFR at new place (Coral Springs, FL) which has appreciated about 5% now.

    I would like to convert this SFR into rental in 1 more year abd move out but family says “NO’ to moving again 🙁

  11. Xiaolei Hu

    Closing cost may be lost, but how could you lose your down payment as well?

    Assume you sell for the same price as purchasing price. You pay off the mortgage, what’s left should include your down payment, correct? unless you took a big cut in selling price?

    Am I missing something here?

  12. Jerry Agbon

    Excellent advice, simple, precise and effective if done with patience. My wife and I are doing this, by renting out our first condo after buying and moving into a single family unit, while at the same time we’re investing into multi-family houses on the side. Our major problem now is getting financing to purchase a second multi family unit after buying the first multi family unit last year.

    • Dave Van Horn

      You are correct – the more doorways you own, the more difficult it may become to acquire traditional financing. Also, they may count each unit in a multi-family as a ‘doorway.’ Utilizing hard or private money may be an alternative.
      All the best,

  13. Hi Dave- I am a little confused here, because these days, we have a “Due on Sale” clause in primary homeowner mortgages. I know one can choose to ignore that, and simply not notify the bank that this is now a rental and you have personally moved on. However, with multiple investor mortgages disguised as “home owner” mortgages, what happens if mortgage interest goes up and the banks start becoming more vigilant about who is taking advantage of those historically low mortgage rates? You might find many banks calling in their cash at one time! I’m thinking 1982-era here.

    Also, how do you get the right insurance for these rentals? Mortgages require proof of insurance. I am thinking, if you had a fire or flood, you would not be able to make a claim as an owner occupant, and if the bank saw your switch from h.o. to the now appropriate commercial (rental) policy, they would bust you. Either way, I think your insurance would be a dud with any claim. We think about insurance a lot in Florida!

    • Dave Van Horn

      Hi Maggie,
      Thanks for your comment!
      Due on Sale is associated with a transfer of ownership, not a change in use. Many mortgage companies expect you to live in a property that you purchased owner-occupied for a certain amount of time. Although I can’t give legal advice and this could vary, I think the rule of thumb is at least a year. I knew I didn’t want to stay in each property forever, but it wasn’t my intent to move out of them right away either – I moved my family into them and stayed at each one for a while.
      Regarding insurance, in my state (PA), it’s illegal to insure your tenant’s contents, so a homeowner’s policy wouldn’t cover that. That being said, it may be best to discuss it with your insurance carrier.
      All the best,

  14. My situation is that I am relocating due to work but I have only owned my home for 8 months, since I have not lived there for at least 2 years, would this still work form me? My relocation is going to be to a new state so my new home won’t be in the same area.

    • Dave Van Horn

      Hi Tony,
      Your best bet is probably to check with your loan officer or real estate attorney. Your loan officer should be familiar with the terms of your agreement. Oftentimes, though, it’s based on a borrower’s initial intent when purchasing. I seriously doubt that the bank would be concerned as long as your loan with them is current.

  15. “… we often listen to our real estate agent when it comes time to moving up to our next home.” Of course, buyers listen to their buyer’s agent. Buyer’s agents tell their buyers to trust the agent’s expertise and experience for what is usually the biggest purchase of a person’s life. “They may encourage you to sell the first home, saying that you can’t afford two mortgages, but they may be squeezing you into as much home as possible on the next purchase” because the more house the buyer’s agent can persuade you to buy, the greater the buyer’s agent’s commission. ” Keep in mind, most real estate agents aren’t accountants or financial advisors.” That is just an excuse. Buyer’s agents have a fiduciary responsibility to advise their client according to the client’s best interest. Buyer’s agents very often fail to fulfill this duty.

  16. Colin Reid

    I didn’t sell my first home. I’m in the military, and once I rented that first home out, I decided I wouldn’t sell any more homes, just collect them as I moved. Then I got impatient and bought a house I never intend to live in. Hopefully that will be the first of many. Now my fiancee and I have 4 properties, 3 of which are cash flowing and one is my home, and we’re shopping for our first small multi-family.

  17. Amy Dan

    Hi, Dave. I am a newbie to real estate investment. I like this article. That is also what I plan to do. I feel it will be a more stable and safe plan for newbies. Thanks. I feel more encouraged after reading it.

  18. Howard Sklar on

    As my first rental was a 17 unit apt building, I never looked back. The fixing up, raising rents & refinance process was more than enough to grow the position at an accelorated rate…..never had to live in it and then change the use. Many ways to “skin a cat” in R.E. as they say. I love the strategy though. Conventional thinking is in place to make the banks rich…give them the lion’s share & the homeowner is left with the “fuzzy end of the loliipop”, that is, the front end of the amortization achedule.
    Love this saying by Charles Givens:
    “Money doesn’t come with an instruction booklet”
    That goes for R.E. as well!!

  19. Thirty years ago I did the same. My first house was a house with a mother in law. When I was promoted, I bought a condo in the new city and kept my house but now it became a duplex rental. Next move I bought again, but kept the condo as a rental.
    I didn’t sacrifice, but I did live in a financially responsible way.
    Happy to say now at 57, I own two homes, mortgage free, 2 rentals mortgage free and am semi-retired.

  20. Jessie Huffey

    This was a great article and I agree that this strategy is a wonderful option for many. If we were unable to get the price we wanted for our last primary residence we would have rented it out. The reasons we didn’t were as follows: we were moving out of state and were reluctant to manage a California rental (not landlord friendly) from across state lines due to the risk, the profit from our sale was mostly tax free and enabled us to not have a mortgage on our current home giving me the opportunity to “retire” early, the profit from the sale enabled us to buy land that we plan to build spec houses on (husband is a building contractor). All that being said, I would definitely consider this strategy in the future.

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