Real Estate Dreams: Why It’s Good When They Shatter

In December of 2013, a real estate dream of mine was shattered. We were one document away from owning the perfect home in Portland, Maine when the deal fell through. I was crushed. I had fallen in love with the city after a single visit (just like with NYC). But it just wasn’t to be.

Dream home built in 1778

I’ve thought about that house (the one that got away) almost every single day since. However, since I’ve been sidelined with some back pain and have pending hip surgery on the horizon, I’ve put that dream on the back burner for the last 5 years.

During this time, I did a lot of thinking and planning, using more of my head instead of my heart. Of course, I want to love where I live. But that can be accomplished in more places than just Portland, which is, unfortunately, too pricey for my budget. To expand my search strategically, I needed to examine my motivations for buying the second home in the first place.

Getting Clear on My Why

It’s so easy to become enamored with the vibe of a city or the curb appeal of a house. Sometimes, people end up compromising on things that are normally very important to them, like budget, when they are smitten. To make sure I didn’t look at other properties with rose colored glasses, I got clear on why I wanted a vacation home.

There are a number of reasons why I’d like to own a second home:

  • Global warming and a desire to escape the heat in warmer months
  • Rental income (renting out and managing property remotely has never been easier)
  • Commuting options have improved and should continue to do so

Opening Up the Search

Now that I was focused more on what I needed in general, rather than on a specific location, it was easier to broaden my search.  I started considering other towns within a 30-minute driving radius. Then, I increased that to 2 hours.

I couldn’t believe that I overlooked doing this for so long, ignoring everything that wasn’t my first choice. That was short-sighted of me. The more I searched, the more I found places like Torrington, CT and Cold Spring, NY that are both scenic and relatively close.

Leveraging Tools

Now that my search radius is considerably larger, I decided to employ tools to help me refine my options. Doing this is going to save a ton of hassle as I don’t need to personally visit every location to rule it in or out. Instead, I can create a short list of towns to explore further as time permits.


As a long time user, I leverage the program to research the number of restaurants, bars, and other attractions in an area. I actually did this with our first trip to New Haven, CT (read more about that trip here). When you create a small overlay of business with property listings, you can get a pretty good picture of what your life might look like in that location.

Real Estate Search Sites

We’ve all used sites like Zillow or Trulia for casual research, but to get the full benefit of the site, you really need to go deeper. Take the time to understand how to “power search” with these tools and create lists of potential investments. Since I started better utilizing these sites, I’ve discovered properties that I might never have found when limiting my search. Email updates and programmed searches can save you time, money, and headaches on your quest to find a property that you’ll love.

Saved searched provide great overview

Things to Consider

Since I’ve had some time to cool my heels, I’ve realized a couple of things that I will keep in mind when I resume my search after recovering from surgery.

I don’t want to spend all day doing DIY stuff

I can handle some home improvement projects. In fact, I did the bulk of my IKEA kitchen install (in our home) by myself about 3 years ago. I also love watching some HGTV home remodels with a “big reveal” at the end. But I don’t really include a big budget for improvements in my bid. That means, I need to get a home that is at least “acceptable” and in “move in condition”, with the potential for slower improvements, over time. Keep it real. No matter how nice you envision that shack that needs extensive roof repairs and a new heating system, you’re probably biting off more than you can chew.

Older Generations Are Starting to Pass

My Mother passed away 8+ years ago now. Due to the condition of her home, it wasn’t really worth what she expected. When it sold, all 10 of her heirs got a small (10k) windfall.

My point here is this: we are on the beginning edge of millions of these types of settlements. So many elderly will be passing in the next 5 to 10 years, which translates to a burgeoning field of opportunity as those estates are liquidated. With families more likely to be in a different location, they’re probably not going to want to fix the property themselves. If you plan to be in the market for real estate, don’t overlook this.

Timing the Market is Pointless

One thing that I always lamented about losing the deal on my “dream home” was that the timing was PERFECT. However, I’m now realizing that there will always be a stock of housing that is available. It really depends on location, features, and the value you will extract from a property.

If you’re buying a property simply for investment purposes, then yes, the numbers need to work and your research should be REALISTICALLY focused around that. However, if a good portion of your return will be realized in actually USING the property, then your criteria need to shift to some softer metrics and include the value of your time.

Final Thoughts

As much as losing the Portland home still stings, the experience made me take the time to reflect and really consider my options. Because of this, I ultimately expect to find a vacation home that’s still perfect for me that costs less money. So really, that loss 5 years ago will be chalked up as a future win when I close on my second home.

This chapter also taught me things about real estate and life that I’m now sharing with others. I hope my story and musings can help you in some way as you plan your next real estate move.

Tell me: Have you ever lost a dream home? How did you move past it?

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