Chicago House Hunting: The One I Loved the Most

Of all the houses we’ve seen, this was the house I had the most immediate emotional response to. Originally listed at $525k, sold for $400k, in a lovely Chicago neighborhood called Peterson Woods. It caught me by surprise because I’m rarely sentimental. I’m also wary of kitsch – I like mid-century design because it’s practical and clean-lined – not because I want to live in a time capsule. This house, however, felt truly special.


It was owned by an elderly woman who had finally reached the point where she could no longer live alone. She bought the house from the architect when it was first built (in 1954) and had lived there ever since. The seller’s agent clearly loved her, and exclaimed “She’s 80-years-old and still drives at night!” Her home was beautiful. Alas, we decided it was too far from the CTA for it to be a serious contender.


I’m a sucker for cove ceilings and corner windows.


Such a kitchen!


Both of the bathrooms had amazing metallic wallpaper.


We called this one “Kimberly’s bathroom,” after our friend who most definitely has this decor in outfit form.


And the basement bar was the ultimate Golden Girls party room.



What got me the most, though, was when I opened the master bedroom closet and saw these shoeboxes:


This was exactly how my grandmother organized her shoes. I took some photos of her ranch house — which she lived in until the day she died in 2002, with her Keds on her feet and her head on her pillow. Even the multi-color plastic hangers are the same:

Polaroid Exif JPEG

No good way to end this post, so I’ll link to this Courtney Barnett song that is the perfect soundtrack for emotional house-hunting: Depreston.

Chicago House Hunting: The One that Got Away

This is the house I’m still kicking myself over: a mid-century split-level priced at $314,900.


For those of you who don’t live in Chicago: mid-century houses are really rare here, especially in our part of the city. This is a pre-1930s bungalow town. Per the Historic Chicago Bungalow Association: “With more than 80,000 bungalows still standing today, the housing style represents nearly one-third of the city’s single-family housing stock.” Bungalows are great, but I prefer a more modern floor plan. And vaulted ceilings? I would do unspeakable things for vaulted ceilings.


We saw this house at the beginning of our house hunt, back when we were young and naive and stupid. It needed a lot of work — the roof, windows, and electrical all needed to be replaced immediately — and it simply seemed like too much for us to bite off with the funds we had available. We hesitated a day too long and by the time we decided to make an offer, it was too late. I felt heartbroken.


Pristine hardwood floors under the terrible carpet!




Glorious closet space.


I later learned more about renovation loan options and determined that the house would have been within our means, which made me feel worse. The only consolation is that it ended up selling for $345,500. So, even if we had made an offer, we would have been scared off by the escalating bids.


At night when I can’t sleep I still think about how I’d decorate this bar…


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.

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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.

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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.

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

California via Des Moines Dreaming

An Open Letter to Matt & Jen Warship:

Do you think your realtor could get us a first-time homeowner two-fer-one deal?  If so, we’ll take this California ranch: 4607 Southwest 16th Street.California Ranch House Exterior

California Ranch House Fireplace

The real estate pictures are hilariously crummy (three of the shed and none of a bedroom or bathroom?) but I was sold on this one:

California Ranch House Basement

AN ALL-WHITE PROJECT ROOM. It will be my Dreamatorium.


P.S. Lest you think I’m self-centered, I picked out a house for you as well: 2801 Fleur Drive.

Tudor House Exterior

Tudor House Interior

Tudor House Interior


Internet Browsing

Guh!  I shouldn’t look at real estate listings for non-major-metropolitan areas.  It weakens my resolve to be Chicago For Life.

All I want is a sub-$200k, 3 bedroom, 1.5 or 2 bathroom ranch, built between 1955-1975 and preferably not updated since that time. I don’t want to pay $30k more because you installed cherry cabinets and stainless steel appliances.
Seriously.  A vaulted ceiling in the living room?  That’s #1 on my wish list.  Crushed red velvet carpet, you don’t scare me.  You’d get torn up as soon as all that stone got PAINTED WHITE.

That floor and that fireplace and that built-in bar?!  Ultimate ping-pong party room.

Come to me, 5648 S Madeline Ave, Milwaukee, WI.  I’ll treat you right.