
If you know us, you know that if we’re traveling, it’s probably to Florida. We’re used to the eye rolls and smirks that are accompanied with the phrase, “Going to Disney again, huh?”
More than once, okay, probably more than I can count, I’ve been asked, “So when are you just going to move to Florida?” And my answer has always been the same. I’ve said it so frequently, it just rolls off the tongue.
“If my parents would come with us, we’d leave tomorrow.”
And that’s the truth. I’d be lying if I said raising these girls doesn’t take a village and that is one of the main reasons we built our house five minutes away from theirs. That being said, we’ve also been contemplating and researching a move to Florida for the past 5 years. Jon and I are diligent researchers and we have combed every piece of information, every blog post, every article, every statistic of nearly every neighborhood in Central Florida. We even sat down with my parents at one point and told them we had a realtor look at our house and were honestly thinking of moving. Can you guess how that conversation went?
Not well.
Not at all.
Most of it centered around some version of “You can’t take the kids away from us.” And truthfully, that would never be my intention. My parents and my MIL are the most helpful and important people in my kid’s lives. Growing up with the influence and teachings of grandparents made me who I am and who Jon is today. Which circles back to the “If my parents would come with us, we’d leave tomorrow.”
And then, my sister took a leap of faith that would change everything. Backstory- You see, my youngest sister moved 6 hours away a few years ago. We all adjusted, my parents didn’t love it, but they accepted it. The reins then tightened on myself and my other sister and we felt like we needed to stay. But then she made waves and decided that her and my BIL were going to move from MA…to South Carolina. And while yes, part of me is sad, I’m overwhelmingly proud of them.

That’s a big one. And so the fissures in the foundation of our life here in Massachusetts began. I’d be lying if I said my parents took it well, another child was really and truly leaving the nest. She was no longer a stone’s throw away and my BIL, who is like a son to my parents and is also my husband’s best friend would be gone too. I like to joke and say they were so sad because they realized then that they were actually stuck with just us and that’s enough to give anyone a headache and maybe start crying.
I kid, I kid. But these children are no joke, as any parents or grandparents of small children know.
But we saw our window. A favorable housing market, remote working capabilities (for Jon), and kids who aren’t in school full-time yet. This was our chance. If we were going to make moves, this timing makes the most sense.
And guess what? Over the course of about a month, suddenly my parents were ON BOARD. They were ready to say goodbye to my childhood home, which they’ve lived in for close to 40 years and they were ready to say goodbye to the snow!
So we dusted off the research folders on Google Drive and dove in head first. We reconnected with a realtor in Orlando who we had spoken with a few years ago and we were off to the races. And what a race it has been.
After we built our house in 2013, I said that I’d never build again. We were 26, with no clue what we were doing. We had next to no money. We paid for our wedding in October and then closed on our new build in November. We maximized every dollar to our name. It was a stressful and exciting time to say the least.

Fast forward seven and a half years and I find myself eating my words. After much consideration in regards to the booming seller’s market, we knew we weren’t keen on getting into bidding wars and bidding far over the asking price just for a chance to probably get our hearts broken when inevitably we lost out to someone else. I’m just too emotionally fragile for that.
Hence, we started to look, once again, at new construction. We had Docs and Sheets full of information on each and every builder and floor plan and town that we were looking at and one by one we narrowed our search. And when I said “what a race it’s been,” I wasn’t joking. The new construction market is just as brutal, so it seems. Trickling lot releases, waiting lists, extended build times. Some builders are even turning to highest and best offers. We knew if we were going to act, a leap of faith would be required and it would have to be probably a little faster than we had anticipated.
I have to put in a disclaimer here that none of this would have come to fruition without our AMAZING realtor, Jose. Honest to God, this man is a saint and he is the sole reason that we felt comfortable enough to make a decision before we could get on a plane to Florida and see the location in person.
Jose sent us video after video of each and every community. He sent videos of the drive into the communities, of the amenities in each of the neighborhoods, walkthroughs of the floor plans. He met with builders and forged those crucial in-person relationships that we just weren’t able to do from MA. He was patient and optimistic and gave us his honest opinion on everything. He never “told us what we wanted to hear.” He would point things out that he could have easily glossed over just to push us closer to making a decision.
If you know my parents, you know they can be old school, and truly, Jose’s videos and his thorough information was the reason why they were on board as well.

At the end of March, we secured our lot and floor plan in a new community in Winter Garden, FL and on April 1st, Jon and I arrived in Orlando to check things out.
We had booked the flights in February, with the timing working out so that we were both vaccinated by the time we left. We didn’t give any regard to Disney or going to the parks and I almost think that it was a sign from the universe because we were actually blocked out of our DVC Gold Annual Pass because of Easter. Even if we were tempted to go to the parks, we didn’t have that option. And honestly, I’m so glad that was the case.
We spent 2 days driving around Winter Garden and the surrounding communities. We drove by every single community and location we had looked at, and (because of Jose) it all felt very familiar. We visited two different Targets and went to Starbucks, obviously. We looked at where the grocery stores, pharmacies, churches, and Trader Joe’s were and checked out the school locations as well.
We also spent an afternoon in downtown Winter Garden which was honestly, amazing. (I’ll have to do a separate post on this.)

If you’ve ever been to Cape Cod, downtown Winter Garden reminded me a lot of walking around downtown Chatham or Hyannis. So many shops and cafes and a bookstore and restaurants. Very quaint and cool. We ate lunch at the Plant Street Marketplace, which reminded me a lot of the Worcester Public Market, which opened recently near our house. There was not a lack of good food, I’ll just say that.

I don’t know how to frame it other than to say, it just felt like we fit there. It felt familiar and like somewhere I could envision my life and my family. It didn’t feel touristy, it didn’t feel like I was in Disney’s backyard, it was just beautiful.
So, here we are.
We’re on our way to Disney World, the girls first trip in a year and a half, Jon’s first actual vacation in longer than that and our first home is going on the market. It’s been a wild past month, cleaning out our house, painting walls, fixing random things, getting it ready to go to market. Keeping things in order with two small tornadoes in your wake is no easy feat. As I write this, I’m still unsure of if I will even hit Publish on this post because part of me is so nervous no one will love our house and want to buy it.
I’ve wanted to tell the world and talk freely about our plans, but I didn’t want to jinx them. I’ve wanted to take my internet friends along on the journey so far, but I’ve been afraid of judgment and those wary eyes and blunt, rude questions. In my heart of hearts, I know that this is our life, our choices and only we know what will make us truly happy. And in this moment, we feel that pull South.
We’ll be further from one sister (for now), still a drive, but manageable distance from the other and my girls will get to wake up and see Nana and Papa every day. Don’t get me wrong, every time the girls get excited about seeing Nana and Papa all the time, in the same breath, they’re so sad that they’re moving further away from Grandma (and great-grandmothers) and their aunts/uncles and cousin. But if I know anything, I know that we will cherish and make more quality time for visits and new memories with each other.
I guess, no one really needs to understand our reasons other than us. But, I’ve always had a hard time with that. People pleaser to my core.
I hope you’ll follow along on our moving journey. I’m looking forward to documenting this transition period for our family, if for no other reason than when the stress and chaos taking up my brain settles down eventually, I’ll be able to look back and appreciate everything we did to get there.

Congratulations!! So excited for you. 😊
(Also, no state income tax in FL, so, bonus! #taxgeek lol)
Best of luck on this next leg of your journey!!!
(PS. Your Auburn house is absolutely gorgeous and I’d snatch it up in a heartbeat if I could! Perfect time for you to sell and move to FL, though, with the way the market is right now!)
LikeLike