Jess Ann Kirby hiked to the top of Mount Tom during her visit to Woodstock, Vermont

We Bought Another Fixer Upper!

House in Vermont Fixer Upper

We bought a house in Vermont!

It feels a bit surreal to share this news, honestly up until now it hasn’t really hit me that we actually bought a house in Vermont. We’ve been talking about doing this for the last two years. And for the most part it felt like a pipe dream. I guess all of you know me really well or I’m super predictable or both, because nearly every single one of you guessed we bought a Vermont house (there were a few marriage and baby guesses sprinkled in, haha).

It’s not lost on me that I’m sharing this news at a time when people are struggling and the world is in a constant state of chaos. I think about how fortunate we are every single day and I truly do not take that for granted. I debated sharing this news at all, but that didn’t feel right. We will be likely moving in for fall and winter. And I wanted to be honest and also share the process with you. This is an exciting albeit slightly scary step for us. When we bought our first house, which three years later we are still working on (I guess with homes it never ends) we didn’t have a baby in tow as we ripped out bathrooms and renovated a kitchen. It should be interesting.

To rewind a bit, when I found out I was pregnant the search for a Vermont house basically came to a screeching halt.

I was super sick, our life has just completely changed and it just was not a priority at all. I put it in my goals at the beginning of this year but I don’t think I believed it would happen. It was more wishful thinking. Fast forward to this winter and about a month into lockdown during Covid. We couldn’t get Vermont out of our minds and the more we talked it through the more it made sense for us. As much as we’ve loved traveling these last few years, we are ready to stay closer to home.

Leaving the animals was always really hard for us. And long flights have become almost impossible for Craig with his back issues. Now with a baby, we wanted somewhere we could go that felt like our home away from home. And for us, that’s Vermont.

Similar to Aquidneck Island, the market in Woodstock is crazy. Our biggest hurdle was finding something we could actually afford. There’s not much. Buying a house in another state during Covid had its own set of challenges. We had to make offers sight unseen and most homes were getting multiple offers the day they came on the market. We didn’t have a specific style in mind. And we just knew we wanted to be in Woodstock or neighboring towns like Barnard, Pomfret or Bridgewater. Throughout the process we made two offers on houses we really loved. We were outbid with offers over asking price both times. We were a bit frustrated and feeling like we just couldn’t compete with buyers in that market. Houses don’t come on often in that area, and even less in our price range.

A house popped up two days after we had been outbid for the second time.

It was in a dream location and sure enough, it was a ranch. We decided to make an offer and agreed if we were outbid again we’d take a break and rethink the whole thing. After some negotiating, our offer was accepted. And we had never even stepped foot in the house.

I think I held my breath the entire drive up for the inspection because we were already so invested I knew we’d be crushed if something really bad popped up. Long story short, the inspection went well. We were on our way to being homeowners in Vermont. The house definitely needs work. It’s in similar condition to our house when we bought it. And it will need renovations throughout. But for the most part it’s all things we can do on our own.

The Vermont house is smaller than our island house but it has a much bigger yard and an amazing location (we are within walking distance to Woodstock Village). It needs an entire renovation, inside and outside. So we definitely have our work cut out for us. I was looking through a folder of images from our first trip to Woodstock and realized that it was exactly two years ago to the day that we biked around Woodstock Village for the first time, and by the end of it said to each other “we need to live here.” There’s been a lot of places we’ve traveled to that we love, but nothing has felt more like home than Vermont.

We haven’t quite decided how we plan to get started, but I’m so excited to share this process with you.

Of course we’ve been planning for months but it’s hard to know what makes sense until you’re actually living in the space. It will get cold much quicker here so we want to get going as soon as possible. More renovation content to come in the weeks ahead, and of course lots of foliage photos because Vermont in the fall is just magic. Thanks as always for your love and support, we are beyond excited to bring you along on this next chapter.

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32 responses

  1. Jen K.

    How exciting!! I’ve only every seen photos of Vermont on IG and it does seem pretty charming! Excited to see all the before/after photos of your house!

    1. Jess

      It is SO charming. Excited to share more!

  2. Katie Gill

    Congrats!! So, what will this ranch home be called?!

    1. Jess

      Well I think it’s The Cozy Ranch North. 🙂

  3. Melinda

    Congratulations!!! Sounds like a fun project and a wonderful place to live?

    1. Jess

      Thank you Melinda!

  4. Erin

    Woooo! We stayed in Woodstock four years ago and had the same thought- we need to move here! We bought a house last March in Addison, about 1h 45m NW of Woodstock.

    1. Jess

      Omg that’s so cool! I’ve never been to Addison but I am so looking forward to exploring more of Vermont.

  5. Hayley

    Congratulations! It is my absolute dream to one day buy a ‘project house’, but we still have so much we want to do to our current house as we convert it from our holiday home to our permanent home that I can’t see it happening for several years yet..so I’m grateful to be able to live vicariously and learn from your experience. ? Sounds like an awesome and brave decision!

    1. Jess

      Thank you so much Hayley. Really looking forward to sharing more of the process.

  6. CC

    Never feel guilty for being happy!
    Life’s short, life’s not fair, so when you find happiness, grab it with both hands and don’t apologize.

    1. Jess

      You’re right. Thank you!

  7. Erin

    SO excited for you guys! Woodstock is one of our all-time favorite places as well; we try to take day trips up there whenever we can (especially this time of year!). Can’t wait to see the place, and all of your dreams and plans for it!

    1. Jess

      Thank you Erin. It really is such a magical place especially in the fall. I’m so excited to spend more time there and of course share it with all of you.

  8. Susan

    Congratulations and wish you all the very best in this new adventure! Looking forward to all your house renovation updates.

    1. Jess

      Thank you so much Susan. I really appreciate it!

  9. Ann K.

    Congratulations Jess! I share your dream of owning a vacation home in beautiful Vermont and mine would certainly be a fixer upper as well. I will be eagerly following along. It’s been great to glimpse the growth and evolution of your journey from when you first started your blog. I’m happy for you and your family.

    1. Jess

      Thank you so much Ann that’s so kind. Really appreciate it.

  10. Elizabeth

    Congratulations!!! I love reading about people who are living their dreams, especially during this trying Covid time when everything seems so bleak most days.

    I am looking forward to following along on your adventure and wish you all the luck in the world.

    1. Jess

      That’s so kind of you. Thank you so much Elizabeth. Looking forward to sharing more of the process.

  11. Lynn

    Well, we kinda knew your surprise lol. And since I completely restored and decorated a 200 year old extended cape farmhouse with a barn and 50 acres on the border and of 1/8 of a mile from the sign “entering Vermont” ( so close) I do know the feeling. We did lay eideboard floors. We knocked out ceilings and exposed old beams and hung herbs . We did really thick butcher block kitchen counters and painted pine cabinets wedge wood blue with black hardware. We did White upper rough putty and lower half paint in a real Williamsburg Red on our walls and had a wood stove in our kitchen and our den. It had a fireplace and 2 bedrooms and an attic upstairs to house our kids. I loved that little house. We were not far from Woodstock and 2 major Ski areas. I loved the seasons and our first snow was on Thanksgiving. We spent 8 great years there raising animals and canning and freezing from our garden. I was never sorry. Good luck on this new adventure. I’m sure it will be beautiful and bring you joy ! Wow ! So happy for you!! I wish that I had a do over !xoxo

  12. Nicole Anne

    Congratulations, Jess!
    Wishing you and your family the absolute best on this new adventure!
    Hugs,
    Nicole Anne xx

    1. Jess

      Thank you so much I really appreciate it.

  13. Sheryll

    So crazy. We had the exact same experience while looking for our vacation cabin in West Virginia this summer. Things were flying as fast as we could see them, we got outbid on one perfect place, and had to walk away from two other places after the inspections revealed big problems (apparently, building codes are very flexible in West Virginia and there are no inspectors in the county we were looking in). We finally found our place right before we were going to give up and wait. So excited and happy for your journey (and my sorta parallel one)!

    1. Jess

      Wow congratulations that’s so exciting!

  14. MT

    I’m looking to buy out of state and there are logistical challenge of not being able to walk the property. Will you be sharing more about the buying process? Sounds like you were already quite familiar with the area beforehand? Did you work with an agent? Did you place a inspection clause with your bid since you bought site unseen?

    1. Jess

      I can do a Q&A about this. We worked with a local realtor who I actually found through a follower that connected us. In my experience all Purchase and Sale agreements have an inspection clause that state if something comes up you have a way out of the contract (depending on different scenarios, circumstances). But I am happy to answer more questions in depth!

  15. Kayla

    Congrats on the new house! Can’t wait to follow along as you renovate the place!

    xx,
    Kayla
    http://www.eatplaydress.com

  16. Jules

    Wow, do I ever identify with this right now! We just bought a home in another province sight unseen (in person) until the inspection as well…which went less well than yours, but thankfully we were able to negotiate a lower price since the fix is $$$.

    But same kind of market, same over asking price/multiple offer situations and similar compromises with size and dated interiors – but amazing location and yard! It felt like I could have written this post myself 😉 Looking forward to following along on your journey while we are on ours!

    1. Jess

      Omg how exciting! Congratulations. Definitely a wild experience buying a fixer upper right now but I am excited for all of the potential.

  17. Lisa Hoffman

    Omg, we stayed in Woodstock for the second time this fall and just loved it! Love the Woodstock Inn and the town is wonderful. So jealous your adventure! We have loved Vermont since taking a VBT bike tour 25 years ago during the fall, and spending a week touring the state,

  18. Amy

    Congratulations! I can’t wait to see what you do with it. We bought a fixer upper as well and I could definitely use some tips 🙂

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