Our Top 5 Takeaways From Selling Our Chicago Condo

As you may have seen last week, we FINALLY sold and closed on our condo! Today we’re sharing the top 5 takeaways from the surprisingly long process, including what we wish we had known before it hit the market.

brass light | stools | solar shades

Whew! We’re so incredibly grateful to have the condo sale process behind us. It took waaaaay longer than we thought, and we learned a lot about the side of real estate we don’t normally deal with. Our amazing agent, Jen, was incredible throughout the process, and we couldn’t have done it without her! Below, I’m sharing the biggest things we took away from the experience.

If you’re new around here or simply catching up, the condo was the first Chicago home we purchased together. It’s also when we started this blog (in 2009)! These posts give you the backstory: why we’re selling the condo | our to-do list before we sell | q+a with a real estate pro | the condo kitchen makeover

1 | Our Expectations Were Slightly Unrealistic

It’s no secret that the real estate market has been absolutely through the roof over the course of the last 18 months or so. But what is the definition of ‘through the roof’? When we originally announced that we were selling the condo, we were inundated with comments from folks whose homes had ‘sold in less than 48 hours!‘ or ‘had received multiple offers in less than a week!’. These comments and the optimism of our agent after a hot spring and early summer market had us expecting a rush of folks beating down the door to buy this cozy little home. Instead, it was crickets.

The feedback from open houses and showings was fantastic. Everyone loved the layout, the improvements and the location. Unfortunately, the #1 bit of feedback that we received was that the unit (or more specifically the bedrooms) was too small. Those bedrooms, I tell you, were the biggest thorn in our side throughout the selling process. In an ironic twist, the things we loved the most about the condo when we purchased it (a cozy, cocoon-like bedroom!) were the things that seemed to drive 2021 buyers away. The efficient floor plan and snug bedrooms didn’t seem to align with what many folks were looking for – and that really took us by surprise.

2 | We Had to Work to Keep Our Emotions Out of the Transaction

After pouring our hearts into this little condo for eight years and all of the milestones that happened while we lived there – like getting married, starting this blog, adopting our first dog… the list goes on! – it was tough to separate the home from the sales process. Why aren’t people able to see the potential that we saw? Why aren’t the improvements we made resonating with potential buyers? Do we have bad taste? We questioned all of our choices, and we discussed at length until our (absolutely stellar!) realtor reminded us that the space didn’t need to resonate with every buyer, just the right buyer. We realized that the countless memories we made inside this space were ours and mattered exactly zero to anyone but us. Period, full stop. This was a business deal whether we liked it or not.

3 | The Upgrades We Made Weren’t the Deciding Factor For Our Buyer

Between having the unit professionally painted, the floors refinished, painting the cabinets ourselves, replacing every last light fixture and staging the home, it turned out that those improvements weren’t even the deciding factor for our buyer. They were more concerned with the floor plan and the fact that it seemed more well-maintained than a lot of the other units they had seen. That said, we were completely caught off guard when negotiating began, and the buying agent tried to compare our head-to-toe refreshed unit to fixer uppers. The fixer upper has an extra cabinet in the kitchen, they said. But the fixer doesn’t have refinished floors and a built-in in the home office!, we’d say. And this is where I refer you back to point 2, keeping our emotions out of the transaction.

The condo kitchen before it’s makeover:

While the upgrades were appreciated, they weren’t specifically what sealed the deal. We certainly don’t regret the improvements or the money we invested to make them, but we also can’t help to wonder if our buyer would have made the same offer on the condo if we had simply painted the walls and called it done. We’ll never know!

The condo kitchen after its makeover:

brass light | pendant light (similar) | faucet | stools

4 | The Hot Real Estate Market Demanded Single Family Homes

As we mentioned earlier, the real estate market of early 2021 was absolutely bonkers. To a degree, the seller’s market is still in play. Folks seemed to be looking for single family homes and larger, more recently constructed condos. People wanted to move out of the city, closer to their family. Many were willing to forgo location for space. The list goes on! That said, the vintage condo market, wasn’t quite as hot. For example, our close friends recently listed their single family home with our exact same real estate agent and had two competing full-price offers within a week of hitting the market!

On the other hand, our listing went live on July 1st, and we closed on November 11th. Our listing was within range – if not lower than – the average from the comps in our Chicago neighborhood. Over that same period of time, we reduced the listing price by $5,000 twice and $10,000 once for a total reduction of $20,000. The final offer that we accepted was also several thousand dollars less than our lowest listing price. While we were potentially overconfident in the value that our improvements would bring to the listing, the seasonality of the Chicago market also hit us hard. Our market cools down (literally and figuratively) over the winter, and the thought of 4 more months of carrying costs wasn’t something we could stomach.

The two examples obviously aren’t an apples to apples comparison, but they’re indicative of bigger trends in our area.

5 | We Learned About a Side of Real Estate We Weren’t Familiar With

We’ve purchased quite a few properties in our lives. However, with the exception of a small starter home that I purchased in Cincinnati prior to moving to Chicago, we had never been on the seller’s end of the transaction.

After touring hundreds of spaces and subsequently purchasing this condo, our primary home, Tree House and the Two Flat, we know what we like to look for in a property. We can generally walk into a space and see how it can be made to work best for us. This is a big part of what we do for a living; we optimize spaces through renovation, design and furnishings to make them, hopefully, better than we found them. That said, we admit that we missed the mark by assuming that every other person that walked through the doors of the condo would be able to envision things the way we could. We had to continually remind ourselves that our tastes and vision simply aren’t the same as everyone else’s. We made improvements to the condo that we loved, but might not be loved by others.

Final Thoughts

This process threw a lot of curveballs our way, but in the end, we’re better for having gone through it. We learned a ton about real estate that will help us navigate future transactions on both sides of the process. We overcame some of our own shortcomings and will handle the next sale (not for a looong time, we think) with more knowledge and understanding. We’ll also be far better prepared if we ever decide to sell it all, and move to the beach, a dream that can only be born after having survived 2020, haha.

Thank you to every single one of you that sent us helpful DMs and suggestions, alternate viewpoints and encouragement. It means the world.

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  • Martha11.15.21 - 9:38 AM

    One thing I learned from my father who acquired properties over the years…never over invest in improvements if it’s not your 4ever home. Improvements can get expensive and rarely do you recoup that investment when selling. Make it nice but within reason if you plan to sell. ReplyCancel

    • Kim11.15.21 - 9:56 AM

      This is good advice, thank you, Martha! That said, I do think it’s important to consider where you’re selling and what improvements are being made. Had we not refinished the floors (which were in rough shape) or paint the walls (which were multi-colored over the years!), I think there may have been a lot more push back on the final price we accepted. Chicago is also an attractive market, and the competition is high in this particular desirable neighborhood as well. Would we have put these same improvements into a property we were selling if we weren’t in Chicago – say, the suburban neighborhoods in Ohio we grew up in – I doubt it. But between your point and ours, there’s a lot of food for thought there. Thanks again!ReplyCancel

  • Veronica11.15.21 - 10:34 AM

    Man, I really feel this post! We have outgrown our condo in the West Loop and have put it on the market a couple of times with a few offers that have fallen through. We have been back and forth on the improvements we have made versus what else we can do to get this place sold, but we think we have had a lot of bad luck! We’re gonna try again next year and I’ll have to keep these points in mind.ReplyCancel

  • Tara C11.15.21 - 10:59 AM

    Congratulations!!! I so admire how positive you are able to be at the end of all of this. Learning from any experience is valuable and you guys embody that. Thank you for sharing the ups and downs of your process.ReplyCancel

  • Sarah11.15.21 - 11:06 AM

    “We had to continually remind ourselves that our tastes and vision simply aren’t the same as everyone else’s. We made improvements to the condo that we loved, but might not be loved by others.”I think a lot of sellers miss the mark on this one, so don’t feel bad! I bought my first home last January, and it was very frustrating to find what I wanted because it seemed like all the homes had been renovated to a very specific, top-to-bottom grey and minimalist aesthetic. I was looking for historical charm, so had to cross off a lot of properties that were otherwise perfect because the sellers were so hasty to appeal to what they perceived as popular. My partner, on the other hand, was more like your buyers- finishes and such didn’t matter at all, it just wasn’t a selling point.
    I’m glad it worked out for you in the end! Thanks for being so open about it from the seller’s side, especially when the process wasn’t perfect.ReplyCancel

    • Kim11.15.21 - 11:43 AM

      Finishes are rarely, if EVER, a selling point for us, but we were under the impression that it mattered to most. We know we can cosmetically change things up, but I think most people want it to be move in ready from the beginning. Maybe that was where we went wrong, but ALSO, I can’t imagine we would have sold it for what we did without any changes at all. It just takes the one right buyer!ReplyCancel

  • Lisa11.15.21 - 11:29 AM

    Your post really resonates with me. A few years ago (before the real estate boom), I sold a beautiful condo in a vintage building in Lakeview, while still living in it. My first comeuppance was when I asked the realtor for staging feedback, expecting him to say, “It’s perfect! You have such good taste!”, as my friends had. Instead, he had a long list of tweaks to make! It then took longer than I expected to sell the condo, and I became discouraged. Finally, however, the right buyer came along. And to your point, I now live in a single family home in the City, with a dedicated office and a yard for my dogs!
    Anyway, congratulations on your sale!ReplyCancel

    • Kim11.15.21 - 11:42 AM

      It is so helpful to get feedback from people not in your own circle. In a way, we had that with the feedback we got on Instagram! Although that felt overwhelming at times, we pushed through and found our buyer. Thank you!ReplyCancel

  • Sara11.15.21 - 11:36 AM

    So happy you guys closed. I struggled BIG time with #2 selling our first home, which my husband bought at the peak of the last recession. It had navy blue carpet in the bathroom and a drop ceiling in every room. We refinished the floors, took out all the drops, new windows, doors, redid the bathroom ourselves, painted kitchen cabs, new counters. The works. All knowing that we wouldn’t sell for much more than he bought it for, but we had a 15-year-mortgage, it was our home for a decade and it felt worthwhile. We thought it would sell quickly. Instead it languished for months until we finally rented it six months later (we were living there for some of it was we renoed the new house). Fast forward to a hotter real estate market in 2019 and it still didn’t go as quickly as we hoped. We got list price minus a seller assist and sold to a young woman who loved the house so much it helped. But man it is hard to not take it personal. (That house is now worth $28K more than we sold it for and $38K more than we bought it for!) I am happy I wasn’t a pandemic landlord, but that hurts a bit. I’ve tried to focus on the good memories we made there and fun we had making our first home our own. I just wish Zillow would realize I don’t own it anymore lolReplyCancel

  • Julie11.15.21 - 11:40 AM

    I love hearing the real estate side of things, thanks for the honestly. We are landlords, so we never sell anything (except a couple of flips), so I’m on Team Keep a Rental (but obviously you do what works best for your life.) I honestly can’t believe the improvements didn’t help the sale. They are beautiful, bright and neutral, not taste specific, and look similar to how we would finish a flip. But I think the biggest thing about this “hot” market is the single family homes with more space. On to the next project!ReplyCancel

    • Kim11.15.21 - 11:45 AM

      You’re right – small city condo after living through a pandemic? Apparently most people thought, no thanks. Ha! Anyway, one reason we wanted to sell the condo is because we knew it had potentially reached its limit in value. We also didn’t want to be tied down to an HOA anymore. The Two Flat, Tree House and our home are part of our long term plans (at least as far as we can see now), but the condo didn’t fit into that vision. Thank you, Julie!ReplyCancel

  • Jasmine11.15.21 - 1:18 PM

    We’ve also been through the struggle of putting our *we think it’s awesome* house on the market and then hearing crickets.  We got lowball offers because of our high cost per square foot (but we had a 4th bedroom and a big corner lot – real estate agents really latch on to whatever metric benefits their client – an extra kitchen cabinet!  Really?)  It’s so frustrating to put your well cared-for and cute home up for sale and have your work downplayed at every turn.  I’m glad you’ve finally finished this chapter – thank you for sharing the ups and downs!ReplyCancel

    • Kim11.15.21 - 2:01 PM

      The ‘extra cabinet’ thing really became a sore spot in our everyday conversation. It seemed so silly, but you’re right, the agent steps up for their client in any way they can, so kudos to them?! Thanks, Jasmine!ReplyCancel

  • Kelsey11.15.21 - 1:18 PM

    Thank you for sharing this! I felt emotional about the sale of YOUR condo so I am sure taking the emotions out was so hard.  Congratulations for the sale but also for making it through the sale! ReplyCancel

  • Vickie11.15.21 - 2:32 PM

    Big congrats. 
    So interesting to hear about your experience. I think you were right that if you wanted it sold, drop the price and be done. 
    Our neighborhood HOA is about like your condo HOA, a lot of bother. But does make sure  everything is kept nice, very tight rules and approval required for everything external. 
    (I thought your condo would sell immediately to a single person who worked from home and had at least one dog.)ReplyCancel

    • Scott11.15.21 - 3:51 PM

      Thank you! We thought the the same, but all’s well that ends well, right?ReplyCancel

  • Nicolette11.15.21 - 3:04 PM

    Congratulations on closing on the condo!!  We (Americans as a whole) are so obsessed with space it really drives me nuts. My dad was an architect and every house he built, the kitchen was the largest room of the house because we all know that is where everyone gathers. In the home he designed for our family, people were shocked how small the primary bedroom was for being such a large home on 20 acres of land. But the bathroom has tons of storage, same with the custom walk in closet, so you didn’t need anything in the bedroom besides a bed, two nightstands and maybe a bench at the end of the bed. I am remodeling my current house which I know isn’t my forever home and put a double vanity in the primary bathroom simply because I know people are obsessed with the idea of having two sinks and I didn’t want it to be a deal breaker one day. ReplyCancel

  • Darcie11.15.21 - 9:44 PM

    Congratulations! That’s a long haul. Give yourselves plenty of time to celebrate and grieve. My husband and I recently sold my first home, a townhome, after I’d lived there 15 years and had many of those same milestones in the space. I’m still struggling with letting go. I took good care of the space, “meticulous” is the word my friends used, and it had good bones. I wrote the buyer a long letter sharing about my memories in the space and giving my info if she wanted to connect. Crickets. Meanwhile the house we bought is only 2 years old but the sellers were rough on it. We paid top dollar to get it in the crazy Nashville market but will have to put thousands more into it to just get it back up to a like-new state. Some stuff is not fixable because it was just built that way, and we didn’t see this stuff until we’d closed and moved in. It’s hard to complain when home ownership is SUCH an incredible gift, but the whole process can be heart wrenching and make you want to live in a van at the beach!ReplyCancel

    • Kim11.16.21 - 10:59 AM

      YES, you said it! Thank you for helping to sum up the same emotions I’m feeling. Serious about the beach thing.ReplyCancel

  • Cici Haus11.16.21 - 10:40 AM

    I feel this. We are just now under contract on our house that’s been on the market for three months. It’s a five-bedroom, fully renovated (and high end – we did not intend to leave my dream kitchen so soon!), open-concept kitchen/living/dining/sunroom, brick ranch with a fully renovated income-producing apartment in the basement on almost an acre IN THE CITY! I could not understand why it wasn’t selling. I had two open houses and only three people showed up, total. But, we were the highest priced house in the (very small in-town) city, there were no comps because a) we were the first ever renovated house in our neighborhood to list and b) no one else had the income property, and it’s a niche area most aren’t familiar with in my city. 
    I cried a lot, but in the end it does only take one person – the right person – and we found them. Oh and I’m so proud of this – inspection was completed yesterday and they found only TWO things to address. TWO in the entire house! ReplyCancel

    • Kim11.16.21 - 11:00 AM

      Awesome!! So happy you found your perfect buyer who will love your home. Congrats, Cici!ReplyCancel

  • Laura11.17.21 - 3:22 PM

    In the current post-COVID work from home environment, I wonder if it makes more sense to style a very small bedroom as a home office. It’s true that small bedrooms are less appealing than ever with more people staying home more often than not, so a home office might be more valuable to a childless couple than a small second bedroom would be to a couple with one child.  I think we all have to rethink our real estate perceptions in this new world we live in.ReplyCancel

    • Scott11.17.21 - 3:42 PM

      Yup! That’s exactly where we landed. Once we re-staged the small second bedroom as an office, it seemed that people saw more potential and we got our offer shortly after that.ReplyCancel

  • Vanessa11.29.21 - 9:15 PM

    I recently heard the comment, “no one wants to buy your castle, they just want to buy your house” and thought it summed up a lot of the emotional approach we all seem to take when we are selling an art project rather than a product.  I guess it’s human nature, but I take those things personally too.  I never cease to cry over roof replacements and home sales for some goofy reason.  ReplyCancel

  • Amanda Grace1.2.22 - 2:06 PM

    Loved this post. And even though the buyers said the improvements didn’t matter, my guess is that it mattered more than they think it did. The improvements you made made the home feel co-hesive, bigger, brighter and clean (which is one thing they said they were looking for!). Congratulations on your sale!

    Ps: I couldn’t help but notice your last comment to move to the beach. Are Sherry & John going to be getting new neighbours in their future. ;)ReplyCancel

    • Scott1.3.22 - 3:25 PM

      Thanks! Haha! We’re not moving any time soon.ReplyCancel


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