Mini house figurine on wood floor with moving boxes in background, symbolizing Gainesville FL real estate transitions. Anna Olcese Gainesville Florida Realtor

Buying and Selling at the Same Time? Here’s How to Avoid 8 Costly Mistakes

If you’ve ever thought about buying and selling a home at the same time, you probably already know: it can feel like a high-stakes balancing act. One wrong move and the whole thing gets shaky.

I’ve walked clients through this process many times here in Gainesville, FL and the truth is—yes, it’s stressful. But with the right strategy and some expert guidance, you can sidestep the biggest pitfalls and move through the transition without losing sleep.

Here are the eight mistakes I see most often (and how you can avoid them).

1. Waiting Until the Last Minute to Prep Your Home

I can’t tell you how many times I’ve seen sellers wait until they’ve already found their next home before they start touching up paint, fixing little things, or decluttering. By then, you’re rushed, stressed, and sometimes listing in the slow season. My advice? Start now. Even if you’re just thinking of selling, take care of those little projects.

2. Not Having a Backup Plan

I always remind my clients: buying and selling at the same time means double the moving parts. And when one domino tips, it can send the rest tumbling. Having an emergency fund, short-term rental options, or even a plan for a week in a hotel gives you peace of mind if things don’t line up perfectly.

3. Falling in Love With a Home Before Pre-Approval

Here’s a tough one—I’ve seen buyers fall in love with a house, only to realize after the fact that their budget doesn’t stretch that far. Getting pre-approved upfront keeps you grounded and saves you from heartbreak later. It’s especially important right now in the competitive Gainesville FL real estate market, where strong offers stand out.

4. Relying on Every Penny From Your Sale

Let’s be real: markets shift. If you’re counting on your home selling for top dollar to fund the next one, you could end up short if offers come in lower than expected. Build in a cushion so you aren’t scrambling if the numbers shift by $10K–$20K.

5. Refusing to Compromise

It’s easy to forget that everyone in the transaction is under pressure—buyers, sellers, and even the other agents. Sometimes giving a little grace (like allowing an extra week before closing or handling a small repair) can be the difference between a smooth deal and a deal that falls apart.

6. Juggling Two Different Agents

Buying and selling at the same time is complicated enough—you don’t want to add more chaos by having two agents pulling in different directions. When possible, stick with one trusted Gainesville FL realtor who can manage both sides. It makes coordination so much smoother.

7. Scheduling Your Closing on a Friday

This one catches people off guard: closing on a Friday sounds great—until you realize the bank won’t transfer funds until Monday. Instead, aim for earlier in the week so money hits your account without delay.

8. Closing Late in the Day

Just like Fridays, late-afternoon closings can backfire. Wire transfers often stop around 3 p.m., and if your deal wraps up too late, your funds won’t clear until the next day. Morning closings give you breathing room.

Let’s Make Your Move Smoother

Buying and selling at once isn’t for the faint of heart—but it’s absolutely doable with the right plan. Whether you’re eyeing homes for sale in Gainesville FL, exploring condos for sale in Gainesville FL, or just starting to wonder what the cost of living in Gainesville FL really looks like, the best first step is to talk through your options with someone who’s been there before.

I’d love to help you line things up so you’re not left juggling chaos. And while you’re searching for your next home, don’t forget—living in Gainesville also means access to some of the best restaurants in Gainesville FL and plenty of fun Gainesville FL things to do once you’re settled in.

📩 Ready to start planning? Let’s connect and map out your next move.

 

 

 

 

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Testimonials

Powell W.

Powell W.

Anna Olcese was great to work with. She made buying my first house an easy experience. She answered questions about neighborhoods and taught me a lot of what I should be looking for as we toured the house along with being extre...
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Mat & Cora

Mat & Cora

Anna is extremely attentive, responsive, and very easy to work with. She is extremely knowledgeable in her field and knows everything about the Gainesville Area and we would highly recommend her to anyone who wants to buy or se...
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Marjell

Marjell

We were recommended to Anna by our daughter and son-in-law who Anna helped sell their home a few years ago. She was very knowledgeable and accommodating when showing us homes. She was always on top of anything that came up, wit...
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