The Houses We Considered Before Buying Our Home

Kind of a fun post for you tonight. Now that things are calming down for us–house moved into, baby delivered and wallpaper (mostly) up 😉–I wanted to tell you a little bit more about our house hunt. Because it was definitely a confusing and complicated time in our lives!

To provide some background, Mitch and I really did think we might stay in our first home forever. It was a dream! The bottom two floors of an old house built in the 1880s with so much potential. Looking back, yes: it was on the smaller side. But coming from New York, it was HUGE to us, and we truly couldn’t imagine ever needing or wanting more. I mean, there were stairs! I was so happy that I cried on closing day, and we spent the next couple of years renovating it and making it our own. We loved that place.

Fast forward a few years and the situation had changed. We still loved our home, but we were now running two small businesses out of it and had a toddler in tow. No matter how many KonMari clean-outs we undertook, we couldn’t change the square footage… and the lack of necessary space was starting to affect our happiness, especially during the city’s soul-crushing winters during which we were cooped up inside the house all the time. (Oh, and I’d soon be pregnant with another baby!)

If it weren’t for our businesses, I think we could have stayed there for a long time. But very quickly, it became clear that something had to change. The first (and arguably the biggest) decision we needed to make was whether we wanted to try to hack it in the city or move to the suburbs somewhere, where things would likely be a bit easier. (I don’t know if you remember my “When Friends Move” blog post, but we were in the thick of it when I wrote that!) After tons of heart-to-hearts, a lot of visits to suburban neighborhoods and quite a few tears 😭, we decided that happy parents = happy kids, and realized that the prospect of leaving made us way too sad. Even though the search would be much more difficult, the Larkins were meant to live in the city.

But WHAT city? While we adored Chicago, it came with three big problems: its harsh winters, high taxes (though surprisingly not as bad as the suburbs!), and terrifyingly competitive housing market. We didn’t want to just stay because it was the path of least resistance, so we decided to explore the following three options:

Leaving, and moving to a city in the south.

  • Pros: We were struggling and wanted a “quick fix,” and moving someplace that was more affordable and WARMER felt like one. If you haven’t heard, Chicago is COLD. ;) Sure, New York gets cold, too. But this is a different cold. It lasts forever and the wind and frost seemingly reaches your bones. It’s bad, and even dangerous sometimes. And it wears on most people, especially by March or April or May when it’s still snowing and all you want to do is get out of your little condo. We recognized that we likely were experiencing the desire to flee because we were short on space… and we knew it would be incredibly difficult to leave behind our friends and everything we’d built in Chicago. But wow: the prospect of packing up and moving to a place with palm trees and where the kids could run around sure was alluring, and just talking about it made us so happy. Oh! I also need to note that the taxes in these cities were amazingly low compared to Chicago. The savings would be life-changing.
  • Cons: We didn’t know very many people, most of the southern cities we were interested in were coastal and had flooding issues, and the public schools weren’t good. Yes, we could take the savings from the low taxes and use that money to pay for private education. But having both taught in public schools for a long time, it was personally very important to us invest in, support and send our own children to them, too… and our hearts were a bit sad knowing that this wasn’t really an option. Finally, we worried that there might be a transient nature to these cities because of the lack of decent neighborhood schools, at least with young families like our own. Once children reached “school age,” would families leave in search of better options? Finally, if we moved to a totally different region of the country, we could possibly take a big financial hit because so much of my “business” comes from local Chicago companies and events.

Moving back to New York. (Probably to Brooklyn!)

  • Pros: While we had fallen in love with Chicago, let’s be serious: big chunks of our hearts would always be in New York. (So much “heart” talk! Clearly this was a very emotional time for us, haha.) There was something so comforting to me about going home, too. (Being close to family and friends again?! A dream!)
  • Cons: Of course, finding a good-sized place in New York would be even more challenging than finding one in Chicago, as the cost of living was so much higher there. (But we thought that maybe just being in NYC would make things better? I’m not even sure. 😂) The dream of owning a single-family home would likely never happen, either. Schools were also an issue. As was the business aspect. And as hard as this was to internalize, we wanted to be cognizant of the fact that going back to New York would likely be an adjustment! Most of our friends had left, and heck, my dad was planning on retiring soon. We had a huge network in Chicago, but not so much in New York anymore.

Staying in Chicago and finding a larger home.

  • Pros: We LOVED our neighborhood and the network we had there. Most of our friends lived in Lincoln Park, the (fantastic) public school we wanted to send Emma to was in Lincoln Park, and our gym (more of a social club, haha) was located in Lincoln Park. Mitch also spent half of his childhood here, which made it special for him but also for me! Being so far away from my family was hard, but Lincoln Park felt like home. :) And, as I mentioned before, a good amount of my “jobs” resulted from being in Chicago.
  • Cons: Because of everything above, we both desperately (and perhaps understandably?) wanted to live in the Lincoln Park neighborhood, where we’d made a life for ourselves. But we weren’t sure we could find something that would work for us there, especially within the boundaries of a particular school district we wanted to be in. (Please know that there are SO many other awesome neighborhoods in Chicago; LP was simply home for us, and if we were staying in Chicago, we didn’t want to leave.) Lincoln Park’s housing market was (and is) tough. While we hadn’t worked with a realtor at that point, we’d scoured listings and attended a bunch of open houses… and we’d come up with zilch. Were we being unrealistic? Would we simply be treading water by continuing to search? Not only that, city taxes were (and remain) astronomical. No, not as bad as surrounding suburban towns, but bad. And I feel like I don’t need to say this again, but the cold was another big con. VERY BIG!

The amount of pressure to make the “right” decision was overwhelming. We had the extraordinarily awesome freedom to work anywhere, and we felt unbelievably lucky for that. But with that came stress. It wasn’t like we were getting transferred for a traditional job and we had no other choice. If we made the wrong decision–and, for example, we were unhappy in the South–it would be our fault. And that was a lot on our shoulders!

But we kept coming back to the warmth factor. And so we booked flights. This was the spring of 2018, about a year after we started our home search in Lincoln Park, and we were serious about making a big change.

Charleston house
Charleston house


Which leads us here: to Charleston, South Carolina. Obviously much smaller than Chicago, but a great option for us. Super walkable, access to beaches, tons of charm, and low taxes. I also had a friend who, with her husband, decided to leave behind the fast pace of New York and raise their family there… and they had nothing but wonderful things to say about the location and lifestyle change. And while doing the same certainly felt a little rash, Mitch and I felt that picking up and moving someplace new wasn’t the craziest thing we’d ever heard of.

We both came from families that had moved around a lot, and had GREAT childhoods because of it. And, I mean, how many people do you meet on vacation who are like, “Oh, I used to be in your shoes. But then I fell in love with [x, y or z location] and just up and moved here! I’ve never looked back!” I don’t know about you guys, but we’d met a LOT of people with that story. And we were lucky enough to have the job flexibility to do it… so why not do it? “Northerners” were heading for Charleston in droves; we weren’t alone in our thinking that this little seaside city could be everything we were looking for!

We initially looked at homes in the “South of Broad” neighborhood of Charleston, and then those in the neighboring town of Mount Pleasant because we’d heard how lovely it was. I fell totally in love with South of Broad, but the prospect of flooding was terrifying to us, and it was a real concern. And Mount Pleasant? Absolutely beautiful. But definitely suburban, and it just didn’t feel like the right fit for us.

The above house, though, was located in a more northern neighborhood of the city, and there wasn’t much danger of flooding. It also had everything we were looking for: extra bedrooms, office space, a full-sized kitchen, a backyard, and a whole lot of charm. A place we could see ourselves raising our children in. The drawback was that we wouldn’t be able to go public, but we found a lot of great nearby private pre-k and elementary schools, and were okay with that.

At the end of the trip, we decided to go for it. We scrambled to get our paperwork in order and ducks in a row so that we could put an offer in, but another offer came in during the process, and we ended up losing the house. I was kind of heartbroken. In the end, I do think I realized that it wasn’t the house I was upset about; it was the fact that we almost had a “solution” to our problems and then it was gone.

But sheesh. It was rough. (Can you relate? Almost everyone I talked to about disappointment during a home search can. Isn’t it crazy how emotional it can be?!)

The decision to stay in Chicago

As we started to begin the search in Charleston again (and actually in Savannah, too!), we both found ourselves feeling sad about leaving Chicago and starting over again. Maybe we we were being a bit hasty, for all of the reasons I listed under “Cons” in the “Leaving, and moving to a city in the south” section of this post. We had this absolutely amazing life in Chicago; was starting over (AGAIN) the right move?!

In the end, we decided to stay in Lincoln Park, but to get even MORE serious ;) and commit to finding a single-family home that worked for our family–what we really wanted!–within the year. So we enlisted the best of the best–Conor Scanlon of Sotheby’s Realty–to help us. (Danielle’s husband!) Conor was amazing. I’ve said this before, but he took so much care in figuring out what we truly wanted in our home, and not only guided us to properties that were right for us but also steered us away from buying potential disasters. He’s the reason we found our forever home, and we’re eternally grateful for all the happiness that’s between these walls. :) (Btw: If you’re looking for a great realtor, get in touch with Conor at Can’t recommend him more!)

Our priorities/non-negotiables

Right off the bat, Conor explained the importance of coming up with a list of priorities and “non-negotiables.” He also noted that my list might be different than Mitch’s, and that this was okay! But having this down on paper would be extremely helpful during our search. I actually think that this warrants an entire blog post on its own, but the condensed version is as follows:


  • Budget (Determined with our financial planner. I talk more about this here.)
  • Location (A particular school district in Lincoln Park, though somewhat willing to explore neighboring areas if the schools were good and it meant significant savings. Also very focused on resale value.)
  • Size (Something we could grow into; a “forever” house. He didn’t want to have to move again in five years. He was more up for a project if it meant more square footage.)
  • Layout (Four bedrooms so our parents, who all live far, could come and stay comfortably; a living room, dining room, kitchen and family room on the first floor; a playroom; office space; and a backyard/outdoor space.)
  • Newer vintage (Because of the upkeep.)
  • Traditional style


  • Budget
  • Location (A particular school district in Lincoln Park. Less willing to explore neighboring areas but not completely opposed to the idea. Resale value important.)
  • Traditional style (Less focused on size. I was good with small/weird layouts if it meant the house was charming!)
  • Move-in readiness (We’d have two young children and I worried that renovations would kill us.)
  • Older vintage (But realized that newer construction might make more financial sense.)
  • Ability to comfortably house our parents, who all live far.

How it went

In an effort to be as honest as possible here, it was tough, despite the list. Mitch and I have a wonderfully solid relationship and rarely fight, and a lot of our “priorities/non-negotiables”–the big ones, at least–matched. But throughout the search, we didn’t always see eye to eye. I’m exaggerating here, but we’d often joke that I loved everything and Mitch hated everything. Kidding.

There were lots of properties we both hated. 😂 But I would say that this was our biggest struggle: I wanted to be done, and therefore was fine with a quirky home with some flaws… and Mitch was more of a realist and didn’t want to get stuck with a property that we’d outgrow or that would end up being a headache and drain on the old wallet. Looking back, Mitch was right to be picky. One-hundred percent. But I was super pregnant and emotional, and would often end up frustrated, in tears. “Let’s just be done” was my hormonal motto, and Mitch’s was “let’s find a good home that works for us.” ;)

What we learned

For us, talking (when not in tears 😉) was SO important. As was taking breaks. There were a few months in there where we paused the search all together because we were losing our minds and needed some time off!

It was also incredibly helpful to see boatloads of properties to truly understand the market, what properties were worth, and what we could realistically expect to get with our budget. Talking to designers and contractors and figuring out how much renovations would cost was also imperative because the cost was almost always significantly higher than we anticipated… and only in a few circumstances did it turn out to (maybe) be worth it.

And I’m not sure I really learned this until our home search was over, but my dad said, “a great house is not the last great house.” I couldn’t see that at the time, but he was so right. I experienced heartache again and again, but lo! There was always another one that came along–albeit sometimes a few months later–that I loved.

And the house we ended up with? The best of all. :)

The most significant and meaningful thing we learned, though, was the importance of understanding and respecting our differences. I, for example, was more emotional and far more likely to fall in love with a property immediately. (And then become devastated when it didn’t work out.) Mitch, though, needed more time to process things. He was totally capable of falling in love with a property, but it would usually take him a few weeks to get there. This took us a while to grasp, but when we did, the journey became easier!

Lastly, we learned what we actually wanted in a home. (Which was the house that we ended up buying!) But let’s go through the process and talk about the houses that led us to where we are now. :)

Note: We saw WAY more properties in Lincoln Park than just these, but most we were able to write off right away for one reason or another. These are the ones that we considered!

Oh! And we learned that we never, ever want to go through this again. We’re staying here forever. 😂

The Houses We Considered Before Buying Our Home by Kelly in the City

The gut rehab

This is a rowhouse that went on the market before we became serious and starting working with Conor. It sold for a ridiculously low price, and while we never actually went to see it, it constantly came up in discussion during our search. “Why aren’t we finding anything?! We missed out on the row house. That place was the answer to all our problems.”

What we liked about it:

The size, the price and the school district. I also personally loved how old it was.

Why it didn’t work:

SO many reasons! First, we weren’t ready to buy when we found it. Second, WE NEVER ACTUALLY WENT INSIDE OR EVEN SAW PHOTOS OF THE INTERIOR, haha. Which means that it was likely a gut rehab–something we couldn’t have tackled considering I was about to get pregnant with our second child. Third, the cost of the house + the cost of gutting it would have likely taken us significantly over budget. Fourth, its facade was on a super busy street and that worried us with young children. Fifth, no parking.

But isn’t it perfect?! 😉

The Houses We Considered Before Buying Our Home by Kelly in the City

The sentimental house

My in-laws’ best friends were selling their house in LP and their timeline just so happened to coincide with ours.

What we liked about it:

It was located across the street from Mitch’s childhood home, on our dream street, in our dream school district. So many memories tied to the house, as the Larkins were over there nearly every day. It was special! And BIG. It also had the Mitch’s perfect layout. Finally, going with this home would take a lot of the stress out of the process. (Reminder: I was pregnant!) No competing offers; no haggling. It would just be done!

Why it didn’t work:

It wasn’t exactly our style, and it needed some updating. In the end, once we ran the numbers, it came in well over budget. That said, we came so close to doing it, and are still a little sad that it didn’t work out! Luckily, the friends are the best and completely understood. :)

“Dream House”

Oh man. I can’t even tell you how hard I fell for this house. It was one street up from the previous house, and it was EVERYTHING I wanted. Mitch, on the other hand, hated it the moment he stepped into it, haha!

What we liked about it:

Again, Mitch did not like it. 😂 But I loved it. The charm factor was off the charts, and the kitchen was re-done and perfect. The ceilings were super high; the crown molding was exquisite; and to the best of my recollection, the bathrooms were done, too. It was old, but I loved that. It was also in the best location, and within the boundaries of our #1 public elementary school choice.

Why it didn’t work:

It only had three bedrooms (not ideal for our parents visiting) and the basement wasn’t finished. Technically, there was an office space on the first floor, but it was very open. There also wasn’t a playroom area. We could dig out the basement, but since there wasn’t any access for big machines, it would have to be dug out by hand, and that would be very expensive. The backyard was also very small, and the garage needed to be rebuilt. Typing all of this out, I now realize that Mitch was totally right in passing on this one, but MAN. I was heartbroken, haha. It ended up selling for quite the discount, though, and we recently saw that the new owners are in the process of building a new garage and doing some other stuff to the property! Oh, “Dream House.” I LOVED YOU.

The sideways house
The sideways house

The sideways house

This looked so much like our old house, but was a WHOLE house!

What we liked about it:

It was so pretty inside. The owners did the most fantastic job renovating and decorating it, and it seriously looked like something you’d see on the Cape or on Nantucket or something. ;) While we were walking through, Mitch kept poking me and asking, “Are you in heaven?” It was pretty funny.

Why it didn’t work:

It was built UP, and kind of felt like a ski house. The kids’ bedrooms were on the ground level floor, the kitchen and living room were on the second floor, the family room was on the third floor (I think?), and the master was on the fourth. With a toddler and a baby on the way, the stairs stressed me out. I also didn’t love that the facade wasn’t on the street. So despite the perfection of everything else, it was a hard no for me. (Mitch, interestingly enough, was more open to it!)

The 1990s giant

The 1990s giant

Okay, I know that this isn’t much to look at from the exterior, but it was really big! Square footage-wise, it had everything we needed and more.

What we liked about it:

Again, the square footage. There were so many rooms, and nothing was in terrible shape. No, it didn’t have much charm, but we could really spread out, and slowly make it our own. We’d never have to move again! It was also just barely within the boundaries of the elementary school zone we wanted. A+ from Mitch.

Why it didn’t work:

Split-face construction. Not the end of the world, but Conor explained that years ago, a lot of Chicago homes were built with split-face block, which doesn’t do well in places that get a lot of moisture. Maintaining the block is tough, and simply not something we wanted to sign ourselves up for. It also makes resale difficult. We were bummed about having to pass on such a big home, but neither of us were heartbroken.

The house next door

The house next door

It took us a while to get into this property, but when we found it, we ASSUMED it was the one. It wasn’t actually next door to our old house, but it was around the corner from our gym and the elementary school. So easy!

What we liked about it:

It wasn’t anything gorgeous, but it was cute, and from the online listing, it looked big. And like I said, it was also right around the corner from our gym and a quick walk to the elementary school. We were like, “Boom! Done!”

Why it didn’t work:

It only had one bathroom on the top floor, which meant the four of us would be sharing. NOPE. It was also on a short lot. The property was later knocked down and there’s a three-flat being built in its place. Oh well. 😂

The house next door

The secluded house

Gorgeous. #omg

What we liked about it:

It was perfect, aesthetics-wise. Nothing I would have changed about it. TOO PERFECT, maybe?! Ha!

Why it didn’t work:

It was in the wrong school district on the other side of a very busy highway that cut it off from the rest of the neighborhood. It was beautiful, and definitely tempting, but we knew that it wasn’t the right decision for us. We learned from it, though! We kept wondering about homes in this area because they were a lot bigger, nicer and more affordable… but after seeing “the most perfect house ever” there, and getting a bad feeling about it, we realized that we should stop looking in that region.

The quaint rowhouse in the best location

The quaint rowhouse in the best location

Oh, boy. This screamed “Kelly” and *made* Mitch scream.

What we liked about it:

The location. It was in an arguably BETTER school district than we had our hearts set on… and it was charming.

Why it didn’t work:

Even I could see that it was too small for us. Would have been great for Kelly and Mitch in their 50s and 60s! Or maybe with kids in college. But for this current life phase, it would have been tough. Doesn’t it look big from the outside, though?!

I should note that after we saw this house, there was a lull in “housing stock.” It was disappointing, discouraging and worrisome; what if we’d missed our chance and would have to wait another year?! But Conor promised us that more would come on the market soon!

The quaint rowhouse in the best location

The house we put an offer in on

The house that almost was!

What we liked about it:

Yes, it was overgrown and needed some gardening work, and it was on the outer edge of Lincoln Park and not in the school district we wanted. But it was newer construction, VERY big, on the right side of the busy highway, and in a district that was fine. It had zero real problems, too. (So rare!) We kept coming back to it and imaging how much easier life would be there, so we put in a lowball offer. (A+ from Mitch as long as the sellers accepted.)

Why it didn’t work:

Well, the sellers rejected the offer, haha. So that was that! But we were both kind of happy that it didn’t work out. There was almost a sense of relief when we got word of the rejection, and it helped us realize how important the school district was to us.

The house we put an offer in on

The designer’s house

Literally owned by a designer, this house was GORGEOUS.

What we liked about it:

So much character! So much attention to detail! And everything was done! It was also priced to sell. While it wasn’t in our favorite part of Lincoln Park, it was in a solid location and zoned for/within walking distance of the elementary school we wanted. Also, the LANDSCAPING! I mean, sure… it would be buried in snow for most of the year, haha, but so pretty!

Why it didn’t work:

The size. It was actually a good size, but we’d probably need to move by the time the kids reached middle school. Mitch was a hard no on this one, and while I was bummed because I wanted our search to be over and weighed approximately 7 million pounds, I did agree with him.

Our forever home

Our forever home

A dream come true! See the tour here.

When we first walked through our now home, Emma was having a TOUGH day. I’m not sure what was going on, but she was crying so much and incredibly clingy, which made touring the house very difficult. Not surprisingly, I loved it. (Oh, Kelly.) I couldn’t believe how much space there was, how traditional the style was, and the fact that the bathrooms and kitchen were WHITE. And the outside?! It looked like something out of New England. A dream come true. But yeah, the experience had been less than magical with a crying toddler.

A couple of days after we saw the house, we left for Rhode Island for our babymoon. And every night, at dinner, we’d talk about the house. It was amazing. It was in the right school district and also in a location we’d never dreamed of being in. But it admittedly didn’t have the ideal layout we were looking for, with both the living and family rooms on the first floor. (Its family room was in the basement.) It was also at the top of our budget, and we weren’t sure we we could get the price down enough to a point that would make us comfortable.

We agreed that after we got back, Mitch would go and look at it with Conor under much different circumstances. Calm and quiet so they could really talk about things! And I, obviously, would stay with Emma. When the showing was over, Mitch called me. I was in Barnes & Noble with Emma reading “Pinkalicious” books. I remember picking up the phone, expecting to hear, “Sorry, Love. Didn’t like it.” Instead, though, he said, “I think we should put an offer in. I love it.”


Of course, we took some time to discuss at length. And discuss we DID. ;) I obviously wanted Mitch to truly love it and not just want to make his hormonal wife happy. (I was also relying on him to be rational, haha.) But in the end, we decided that it had almost everything we were looking for, and that was enough.

  • Within budget if we could negotiate
  • Location (Better than we’d ever imagined! Also within the school district we were looking for.)
  • Size (Something we could grow into; a “forever” house. Four bedrooms, a playroom, tons of outdoor space, office space, and enough living space–even though some of it was in the basement.)
  • Newer vintage (It was built in the 1880s but renovated and just about taken down to the studs about 15 years earlier so ZERO issues.)
  • Traditional style (The sellers had maintained that original charm!)
  • Move-in readiness (No kitchen or bathroom renovations!)

After a little bit of back and forth and a lot of sweating and worrying on my part, we came to an agreement with the sellers–and the good news came in via phone while we were in HomeGoods, of all places. 😂 (Barnes & Noble and then HomeGoods. Ironically enough, I almost never go shopping in-store. Too funny.) And just like I did with our first home in Chicago, I cried.

It felt so right!

The journey from “offer accepted” to closing wasn’t as easy, though, and I definitely want to write a followup post about the mortgage process and how we navigated it. But it sure does feel wonderful to be on the other side of the home search, and we’ve never been happier!

Without a doubt, this was the home that we were meant for. It’s only been a few months, and we’ve already made so many incredible memories within these walls. (Namely having Lucy on the same day we moved in, but hey, at least it makes for a great story to tell at her high school/graduation parties!) We’re so unbelievably grateful, and can’t wait for everything that’s to come.

Thanks for reading, and please let me know if you have any questions/ideas for my followup posts!

Past home posts:

We’re Moving!

New Home Tour

Mini Master + Master Bath Tour

10 Recent Home Purchases

Preppy Deck in Progress

Plans for + Progress on Emma’s Room

How We Moved + Had a Baby on the Same Day

Designing Our Master Bedroom with Serena & Lily

Eight Deck Updates

Rugs for Little Girls’ Rooms

Master Bedroom Progress