The Chicago Homes We Considered Buying But Didn’t

We have toured roughly 30 different Chicago homes over the last two years in search of our dream Chicago cottage.  Over that time, we’ve toured fixer uppers, turnkey properties and everything in between.  I’m sharing the five Chicago homes we were closest to buying and why we didn’t as the #HerrmannitoHouse hunt continues!

A Family Home for 90 Years

What I loved about it

I LOVED this home because there was so much history to it.  The woman who lived here was born in the house.  She lived there her entire life buying it from her parents and raising her family there.  At the time, she had recently passed and her husband was still living there.  I wanted to save this home so badly because I knew it was a candidate to be torn down.  It also seemed like a Chicago home we could make our own.  I especially loved starting with the attic from scratch.

What we would change

Um, everything.  This home was a full gut rehab with the exception of the basement oddly enough.  The home was short so we would have to blow it back.  So many Chicago homes are dormered and this house taught us all about the concept of dormering where you essentially raise the roof.

Why it didn’t work out

Aside from the cost of a full gut rehab (which you can technically build into your loan by the way), what scared us the most was the timeline.  We walked the property with our contractor who flips homes in Chicago and he estimated the process would take 8-12 months.  The thought of a project that massive and double rent for a year scared us away.  Sadly, this home was just torn down in the last two weeks – breaks my heart.  In the world of Chicago homes, I would have loved for this to be ours if only we had more time.

The details

The Wallpapered Beauty with a Sandy Basement

What I loved about it

I loved the first-floor layout of this home.  You could almost picture the family living there.  It also had a decent backyard and was actually the first home we’d seen with a backyard.  My favorite part of the home though was the foyer.  It was classic Chicago.  So stately and the vintage wallpaper was dreamy.  I knew we most likely wouldn’t be able to keep it, but I would have replaced it with something similar.  When I think of Chicago homes, I think of a house similar to this one.

What we would change

This home also needed to be gutted.  Other than the foyer staircase, we would take everything down to the studs.  The plumbing and electric needed to be updated.  The floor plan upstairs needed to be completely reworked.  We would need to pull permits and work with an architect to determine the proper layout.

Why it didn’t work out

One of our key criteria is to have a home with space in the basement.  Ideally, we want a basement we can finish and add value.  However, as long as it can act as a play area for Emmie, we’re OK with it.  This home had super short ceilings in the creepy basement and towards the front of the house, there was a pile of sand.  Yes, you read that right, an actual pile of sand.  Why?  Well, we determined the home’s foundation was indeed sand and this part of the house wasn’t quite finished.  Strange, right?  It was enough to scare us away so we didn’t move forward.  I was pregnant at the time and actually cried when we decided not to move forward because I knew it’d be torn down.  It was my hormones for sure, but I also (oddly) care a lot about these old homes! It was indeed torn down and is now a huge, modern single-family home.

The details

The Cute Cottage Chicago Home

What I loved about it

That door!  I loved the porch here.  So much potential for us to make it adorable.  Also, I found the front yard to be super cute.  It looks awkward now because of all of the mulch, but that could easily be taken out and you could lay down sod.  The inside of the house was updated and they did a lot of the work that we’d like to avoid (like updating the electric and plumbing).  Of all of the Chicago homes we toured, this had the cutest front door.

What we would change

This home didn’t have a garage, so we would build one.  The guest room was teeny and backed up to the small living room so we would take out the guest room and make a proper sized living room, which means we’d be down a bedroom.  To make up for a missing guest room, we discussed finishing the basement, which had 7 foot ceilings.  While not perfect, it was doable.

One of the things I didn’t like was the number of bathrooms.  There were too many!  Weird, right?  It was a 3 bed, 4 bath home that couldn’t fit my dining room table.  I kept joking that I could invite all of my friends over to use the facilities at the same time, but couldn’t serve them a meal at one table. Ha!  As someone who loves to entertain, that really bugged me.  Also, because the bathrooms upstairs were so large, there wasn’t a third bedroom, which we felt was a big miss.

Why it didn’t work out

This was the home we actually put an offer on, but backed out.  I wrote about the experience sharing how grateful I was that our realtor, Brooke Vanderbok, talked us out of it!  We put in an offer that expired at midnight.  The sellers decided they wanted to see what other offers came in the next morning and asked us for our best and final the next day.  Since our offer expired, we were off the hook and politely declined to share a best and final offer.  Thank goodness because that home was ultimately too small, and I think the street was too busy for easy parent parking.

The Details

The Most Magical Block

What I loved about it

I loved the idea of this home.  It is located on literally the most magical block in North Center.  It’s the yellow brick road of North Center.  The home also had a lot of potential.  It had a great layout with all mechanicals, plumbing and electric updated – big win!  Plus, the backyard was literally an oasis. [Side note: If you’re touring Chicago homes, check out North Center.  It’s such an adorable, underrated area].

What we would change

This home also needed a garage.  While the block was wide open, we’d still want to build one.  The upstairs had a massive bathroom that could be split into two, which we would have also explored.  One of the things I hated about this house was that the wall connected to the staircase was open so there was a lofted feel to all three levels. I’m not a fan of that because I don’t want to tiptoe around the house once Emmie is in bed.  With a lofted feel, sound carries and could wake the baby.  The kitchen layout was also pretty funky and my office space would be dingy.  Since I work from home a few days a week, having a solid (and sunny!) office space is a must-have for me.

Why it didn’t work out

I wrote all about the experience here, but this home had a strange pole in the middle of the backyard.  Moving it would cause us to work with The City of Chicago, ComEd, and all internet providers to move wiring and re-hookup everything.  That sounds like a nightmare to me.  I’m the logistics manager for the Herrmannitos, and it felt like a task too hairy for me to take on. [Matt agreed for the record].

The details

The ‘Could Be’ Dream Home

What I loved about it

Not a whole lot to be honest.  The first time we toured this home, I hated it.  I didn’t get a good vibe from the home.  The woman who owned it had rehabbed it about 12 years earlier and she designed it very differently than I would have.  However, when we toured it again, it grew on me.  I loved that the kitchen opened up to a great family room.  This home was also in our ideal neighborhood walking distance to the school with great street parking.  I’d loved the pieces surrounding the home, but not the actual house.

What we would change

This home was at the higher end of our budget, so we would need to be crafty with how we spent our renovation budget.  Initially, we would finish the basement (which we knew had water damage – you would think we would have gone running after our Lincoln Park breakup!)  However, we would waterproof the basement and then finish it creating a guest room, updated bathroom, and playspace.  The dormering on the upper level felt incomplete and we would update it eventually, which is a big project with a hefty price tag.  This home was missing the charm that I see in many other Chicago homes.

Why it didn’t work out

Well, you actually know about this one already.  We did put an offer on this home but lost it in a bidding war.  I’m actually really proud of Matt and me on this house.  While we lost it in a bidding war, it’s because we had a personal price ceiling not because we couldn’t afford it.  When we added up the work of finishing the basement and redorming the upstairs, we determined how much we would pay for the house based on what we could ultimately sell it for.  We offered that and someone offered more.  I’m glad they did because I didn’t love that house – I just felt desperate and was ready to settle.  That’s never a good way to enter into a relationship.

The details

We’ve toured so many Chicago homes that this is truly just a snippet.  We do have some updates to share because we’ve made a few decisions, but I’m not ready to share it quite yet.  We changed our strategy and things might have fallen into place.  Stay tuned…

Meet Jen

I’ve always had a love affair with creation. Since I was a child, I handmade my gifts or combined toys to design something new. Fast forward twenty years, and I’m still making my gifts every holiday and designing new ways to do things.

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