I’m bullish on real estate. Yet I recently sold another rental property. This type of incongruence between thought and action can feel unsettling and even counterproductive to wealth creation. But it doesn’t have to be.
Because while maximizing returns is a big goal on your road to financial independence, it’s not the only goal. Sometimes, selling a property, despite being optimistic about the market, is the right move for your life overall.
In my case, letting go of a rental simplified things. I’ve always felt managing three rental properties in one city was my limit. But when I bought a new home in 2023 and decided to rent out the old one, I crossed that threshold. It was like buying a large stock position on margin and surviving.
When the tenants gave notice a year later, I saw it as a window to reset.
Why Selling Is OK Even If You Think Prices Will Still Go Up
Here are eight reasons why it’s OK to sell your property, even if you believe real estate prices will continue to rise.
1) It’s Better to Sell in a Bull Market Than a Bear Market
Selling real estate is stressful. Even if you get into contract, any number of issues can delay or derail the closing. But when you’re selling into strength, the odds of a smooth transaction go up. A buyer in a hot market knows there are others waiting in line. Hence, they try to follow through.
In a bull market, bidding wars are common and tend to reset prices higher through a step-up function. In contrast, a bear market can feel like a liquidity trap—no buyers, falling comps, and painful price cuts. Prices don’t always fall gradually; oftentimes, they gap down. If they do, your home equity could get wiped out if you are forced to sell.
On the west side of San Francisco, it’s a bull market now. Local economic catalysts are drawing in jobs and families, creating stronger demand. So I chose to sell into strength rather than risk being forced to sell later when the market might be weaker.
2) You May Already Have Too Much Real Estate Exposure
In general, I don’t recommend having more than 50% of your net worth in one asset class. Concentration risk is real. Please see my recommended net worth asset allocation for financial freedom. After purchasing another home in 2023, my real estate exposure temporarily ballooned to around 55%.
At one point, I had a primary residence and five rental properties—four of which were in San Francisco. When devastating fires swept through Los Angeles County and wiped out entire neighborhoods, I was reminded how quickly real estate wealth can be destroyed.
When my tenants gave notice, I saw a chance to reduce exposure and rebalance during the strongest selling season of the year: spring.
3) You’ve Tried Being a Landlord and Didn’t Like It
Holding real estate long-term is one of the best ways to build wealth. Renting out your property helps you ride the inflation wave, while hopefully generate positive cash flow.
But being a landlord isn’t for everyone, and that’s OK. If owning a rental property lowers your quality of life or consumes mental bandwidth you’d rather invest elsewhere, selling is a reasonable choice.
I gave it a year. The tenants were fine, aside from a yanked faucet nozzle that caused it to leak and a neglected front yard. But even small issues feel magnified when you’ve mentally moved on.
I felt like I was fortunate the home faced no major problems for the year, like a leak. So I chose not to press my luck further once they gave notice. Although, if they hadn’t given their notice, I would have happily kept renting out the home to them.
4) You Can Potentially Earn a Greater Return Elsewhere
With the 10-year Treasury yield above 4%, I could earn almost as much risk-free as I did from the rental. The hassle and risk of being a landlord didn’t justify the modest yield premium.
For me to hold the property, I needed confidence in achieving at least an 8% return—roughly a 4% premium above the risk-free rate. Given a 43% loan-to-value ratio, it was certainly possible. But I wasn’t more than 80% confident it would happen.
If you can redeploy the equity into similar or better-performing assets—or simply diversify your risk—it’s worth considering. And even if you can’t match the return, freeing up time and energy for other priorities has real value too.
In addition to Treasury bonds, I find residential commercial real estate and private AI companies appealing, giving me at least three compelling options for reinvesting the proceeds. I hadn’t anticipated a 20% correction in the S&P 500 soon after the house sale, which created a fourth attractive investment opportunity.
Real estate can tie up a significant amount of equity, especially in high-cost markets. If you identify a better use of funds, it may make sense to unlock that capital and put it to more productive use.
5) You Qualify for the Tax-Free Home Sale Exclusion
If you’ve lived in your home for at least 2 of the past 5 years before selling, you can exclude up to $500,000 in capital gains if married, or $250,000 if single. This is the Section 121 capital gains exclusion rule. Renting the property for one year before selling still met the 2-out-of-5-year use test, so we qualified for the full exclusion—minus depreciation recapture.
Not having to pay capital gains tax on up to $500,000 is a huge benefit, especially if you’re in a high-income bracket. If you’re approaching the end of the 5-year window or tax-free appreciation limit, it may make sense to sell and lock in this tax advantage.
6) You’ve Found a Better Home and Moved On Emotionally
Some homes serve their purpose for a period of your life—and that’s enough. We bought the property we sold as our “forever home” during the pandemic. It was a sanctuary that dramatically improved our lives for three years.
But deep down it was always a rung on the property ladder. After moving out and renting it for a year, we were no longer emotionally attached. We were making new memories in our new home and no longer missed the old one. That emotional detachment made selling easier.
7) You Want to Reduce Liability and Headaches
Owning rental property exposes you to potential legal, financial, and safety risks. These can include tenant injuries, discrimination claims, habitability lawsuits, or city ordinance violations. Even with good insurance and property managers, the liability and stress can wear on you.
After years of being a landlord, you might decide the peace of mind that comes from reducing liability is worth more than the extra cash flow. A clean exit now could prevent a future legal or financial mess.
In my 22 years as a landlord, I’ve never had an issue with a tenant—a record I attribute to thorough screening and a solid lease agreement. That said, I recognize that each new tenant brings a new set of risks. In this case, the house we sold was rented to multiple roommates rather than a single household, which added another layer of complexity.
8) You’re Preparing for a Lifestyle or Career Change
If you’re planning a major shift—such as retiring early, relocating to a new city, downsizing, traveling more, or changing careers—you may want to simplify your finances and reduce asset management responsibilities. Having our first baby in 2017 was the primary reason why we sold a property back then.
In considering this latest sale, I prioritized time freedom and location flexibility. Selling two or three rental properties before relocating to Honolulu in 2032 will be a challenge, especially if the market turns. By selling one now, I reduce the pressure to sell multiple properties later.
This step has already lightened my mental load and improved my overall happiness and lifestyle.
It’s OK To Not Always Optimize For Maximum Returns
Selling a property even while bullish on real estate doesn’t make you irrational. It makes you a realist who understands that personal finance is personal. Sometimes the right decision is about simplifying life, rebalancing risk, or just reclaiming peace of mind.
We don’t always need to squeeze every last dollar out of every asset, especially if we’ve achieved enough wealth to be satisfied. Sometimes, locking in a win is the smartest move you can make.
Readers, have you ever sold a property even though you believed prices would continue rising? If so, what motivated your decision? And are there any other reasons for selling that I haven’t covered in this post?
If you’re looking to invest in real estate passively, check out Fundrise—my preferred private real estate platform. Fundrise focuses on high-quality residential and industrial properties in the Sunbelt, where valuations are lower and yields are higher.
Some commercial real estate valuations have dropped to levels near the 2008 financial crisis lows, despite today’s stronger economy and healthier household balance sheets. Seeing this as an opportunity, I’m dollar-cost averaging into the sector with my home-sale proceeds while prices remain attractive.
Fundrise is a long-time sponsor of Financial Samurai and I’ve invested $300,000+ with them so far. About half of my invest in Fundrise is in their venture capital product as I want to build a decent amount of exposure to private AI companies.
“Why Sell When You’re Bullish on Real Estate Prices” is a Financial Samurai original. All rights reserved.
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