Sell then buy or Buy then sell - which is best?

Question

Hello all,

My husband and I are going to put our little duplex on market in June 2026. We have looking to purchase another duplex to house hack as well and get out Eugene city laws that are not in favor of the landlord. Since starting our search we have only found 1 duplex that we wanted to move into in February 2025, but our realtor did not want to put in the offer while we were on vacation and it went pending.
I am not sure which is best, to sell our current duplex, rent, and then buy another one? Or Buy a new one then sell our current duplex? Has anyone been in this situation and what is your experience? What worked for you and what did not?

Theresa Harris · Answer

As you don't need to sell your current home to buy the next property and you've been actively looking for 8 months and only found one that could work, I'd suggest waiting until you find the right home and buy it.  You can then sell your current home.  Otherwise you are going to have to find a place to live between selling your current home and buying your next home and I know you say you don't mind moving twice, but reality can be different.

Crystal Smith · Answer

Before I comment on the topic of your post, I respecfully think you need to reconsider your realtor. That realtor should have submitted an offer and not waited until you got back from vacation.

Since you are owner occupants you should evaluate if you have enough equity to use a company like UpEquity.  The company has a program that will allow you to purchase your next home before selling your current home- The company will purchase your home giving about 80% of the equity up front so you can buy your next home.  When you sell the duplex you get the other 20%.  They naturally charge a fee for their services so you'll have to evaluate if it's worth it.  There are some other companies that will provide 6 to 12 months interest free bridge loans to faciliate the purchase of you next property before selling your current property as well.

Joseph Tadres · Answer

Hey Samantha! I would keep it if I had enough cash. You have to make sure you find some really good tenants since the city laws are not in favor of the landlord.

Samantha Chacon-Johnson · Answer

@Joseph Tadres I don't want to keep it.

Mike Grudzien · Answer

I agree with Chris.  And Chris Watkins is an outstanding lender to have on your side.I'll add this: look up Dan Gandee (here on BP).  He's a great "real estate strategist".  That is, he has the experience and savvy to "slice and dice" any deal ten different ways.  He's a broker and an investor.  And he has clients liquidating their portfolios: maybe has something already that meets your requirements.

Samantha Chacon-Johnson · Answer

@Chris Watkins yes I plan to put ours on the market in June.

Samantha Chacon-Johnson · Answer

@Theresa Harris I think I am more nervous of having two mortgage payments and trying to navigate that. Plus, I think ours is gonna take awhile to sell.

Chris Watkins · Answer

Hi Samantha!

Are you looking to buy a duplex in Springfield? Duplexes are a hot commodity around here these days, so finding a good option is going to be tough. Selling, then renting involves moving twice, which is a big pain. Depending on how much equity you have in your current place (and your other income/debts), you may a good candidate for either a HELOC or bridge loan that can tap some of that equity to purchase the new place (when you find it). Then you can sell after you buy and not have that time pressure or need to rent in the interim. Happy to dive into more details if you like.

It also sounds like your realtor wasn't really serving your interests. There are a lot of good, investor-friendly agents around. I'm happy to share a few I know who may be better able to help you out.

Chris

Chris Watkins · Answer

If you have the capital to buy it seems that you can be patient on both the new purchase and sale of existing duplex. It's not a great time to be a seller right now, with seasonal slowdown and more houses on market depressing prices, so selling right now doesn't seem advantageous if you can wait until Spring.

Samantha Chacon-Johnson · Answer

@Chris Watkins Springfield, Creswell, Harrisburg, Brownsville, Walterville, Pleasant hill, etc. I would like to purchase by October 2027.

I don't need the equity or profit to purchase another duplex. We have enough capital to purchase one now and I want to use the profits from the sale to pay off my student loans and then put the remaining in a high yield savings account. I am not interested in a bridge or HELOC, burnrd once with HELOC, not looking to go back.

Work does not bother me, moving twice is not a problem, but I am interested in hearing from people who have been in a similar situation. Pros/cons, what was excepted, what was frustrating, etc.

Sell then buy or Buy then sell - which is best?

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