House Hunting: How We Got Started

Jarrod and I started the house hunting process this past summer by biking to open houses on the weekends. The biking was great because I became more comfortable riding in the city and it gave us the opportunity to explore new streets. (The neighborhoods in which we’ll be able to afford a house aren’t neighborhoods we had previously spent much time in.) The open houses were great because we weren’t actually serious about buying at the time. It was a no-stakes way to familiarize ourselves with the market, learn about the types of houses available and — let’s be honest — creep on other people’s homes. If you don’t have a realtor already in mind, open houses are also a good way to casually meet and vet agents.

At that stage, we thought a lot about what we didn’t want in a home. Time for bullet points!

Why not a condo?

Most young(ish) buyers in the city purchase a condo, and they make a lot of sense for a lot of buyers, but we’ve ruled them out because:

  • Group decision making. After a decade of being a renter, when it’s time for us to own a property, I want to be able to choose what happens to every aspect of the interior and exterior. We toured one condo building, for example, that had a lovely antique rug runner on the communal stairs. The seller’s agent said “Don’t worry, the condo association will be replacing that soon.” Guh! Things like that, big or small, would be a drawback of a group of condo owners deciding how our homeowners association fees are spent.
  • Similarly, we want our home to feel like it’s ours. We just wouldn’t get the sense of privacy and total ownership with a condo. I’d like a yard to garden in, Jarrod would like a basement area for bike repair, and we’d both like to be loud and drop things on the floor without worrying about being jerks to our neighbors.
  • In the real estate market, condos are the first to depreciate and the last to recover. So many of the condos we saw had been purchased at the peak of the recent bubble. The condo shown below sold for $356k in 2006 and is now lingering on the market for $284k.

4428 N Malden – $284,000

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Why not a two-flat?

Another good option for first-time city real estate owners is an owner-occupied multi-unit building. You live in one of the apartments and rent the other(s) to help pay your mortgage. Many of the expenses related to the rental unit and communal areas are deductible, which helps with taxes. We have a few friends who do this and they recommend it highly. We went back and forth on the possibility of buying a two-flat, but ultimately ruled it out because:

  • Sharing our building with a renter would have the same communal feel as a condo. Even with owning the entire property, we’re afraid it wouldn’t feel fully ours.
  • We’ve lived in a really great two-flat for the past several years. We have unlimited storage in the basement, garage parking, a yard, landlords who let me decorate and improve the property, awesome downstairs neighbors, etc. So, we’ve already experienced a lot of the immediate perks of a two-flat, and the properties we’d be able to afford would likely be less appealing than our current situation.

Sorry, no pictures are available of the multi-unit property we saw, but if you’re curious, this is a good representative: 4214 N Sawyer – $345,000

So, single family occupancy or bust!

For those of you who just want to see some Chicago real estate, here’s a round-up of nearly all of the homes we’ve toured via open houses. I’ve included a few pictures and the Redfin link in case you want to see more (although these homes have sold now, so the Redfin photos won’t be available forever).

A quick word about Redfin: It’s amazing. I had been using Trulia, but Redfin is where it’s at. It’s updated with MLS listings in real-time, and their app is so great.


2223 W Greenleaf – $345,000

This house was a perfect mix of modern and vintage, and it had the best kitchen renovation we’ve seen. Middle of nowhere location, unfortunately.

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4244 N Bernard – $359,000

A month after seeing this one, we learned via Facebook that some friends bought it!

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4827 N St Louis – $325,000

This house was unremarkable but we liked the yard – it was all native plants, which we hope to do with our future yard.

4827stlouis 4827stlouis2 4827stlouis3


5505 N St Louis – $245,000

This house confirmed that there is a fixer-upper line we don’t want to cross. Ideally, we’ll find something that is dated but functional – something we can make clean and livable as we tackle projects over the coming years.

5505stlouis 5505stlouis2 5505stlouis3 5505stlouis4


5849 N Whipple – $480,000

Upstairs laundry! These people were livin’ the dream.

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6235 N Rockwell – $355,000

Very nice but much too far from a train.

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6133 N Christiana – $319,000

I’ll leave you with a really interesting one. Mid-century properties likes this are very uncommon in our part of the city – most single family homes are built before 1940. The location isn’t great (hence the low price) but we toured it out of curiosity. It’s probably the only house in Chicago where I would want fewer windows. The second floor is nearly entirely glass and every single window needed to be replaced.

6133christiana 6133christiana2 6133christiana3 6133christiana4 6133christiana5 6133christiana6

That’s all for now! Next up: details on mortgage pre-approval and working with an agent.

14 thoughts on “House Hunting: How We Got Started”

  1. Daily Redfin user here. The market is so slow right now and my addiction is so strong that I have taken to looking up past sales in desirable spots just so I have new houses to look at.

    AND THAT LAST HOUSE. I wish I could pick it up via crane and drop it off in Minnesota. Those windows would be put to much better use overlooking a nice wooded lot as opposed to the neighbor’s house.

    1. I partnered up before the rise of dating apps but I imagine I use Redfin like singles use Tinder. I get a rush every time the notification badge indicates there’s a new listing. “ARE YOU GOING TO BE MY HOUSE?!”

      Yep, that Christiana house was so beautiful and so ill-suited for the lot. The neighbor’s house was the BEST view it had going for it – the back of the house overlooked a Mexican restaurant’s dumpsters.

    1. I really did love Greenleaf. I should clarify: “middle of nowhere” still means it’s in the city, just not in a neighborhood that offers easy access to public transit. We do drive, but prefer to use the CTA for going out in the city.

    1. ERIN: MIND MELD. I originally wrote something about that in my post but deleted it for fear I sounded (even more) like an asshole. The agent kept going on about how the seller had it custom built and I was thinking “ANACHRONISTIC.”

  2. Just found your blog and you’ve made my day! I’ve only made it through half a dozen or so of your posts and I’ve laughed out loud several times. Love your clever storytelling style! Can’t wait to see how your house hunt is progressing. It’s exciting, depressing and exhausting all at the same time (the house hunt, not your blog). And by the way, I’m with you on not meeting your end in an ice cave collapse. So not what you want to be remembered for!

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