5 Coolest And Quirkiest Houses In Portland, OR.

Portland Oregon has long been a city of quirky dive bars, unconventional personalities, and for just being flat out “weird.”

Many of the people have adopted this city’s cultural norm, as they pride themselves in being open minded and non-judgmental.

Some of those people have even decided to showcase the best of the cities weird personality by sprucing up their homes to match the character of the surrounding environment.

Being born and raised in Portland, OR by an unconventional family spending years going through back roads and side alleys, east side and west sides whether personally or professionally, these are some of the coolest homes I have ever come across.

There was no poll taken for this piece, this is simply one person’s opinion after years of home scouting and searching. Here are MY top five coolest and quirkiest houses that Portland has to offer.


This house is one of my favorite houses of all time. Tucked away in one of the most beautiful neighborhoods you will ever see.

The Pink House has old Scottish architecture combined with 70’s flavor. I never thought you could make a pink house look tactful, but my hat’s off to these owners as they have done a fabulous job.



This house seems to stick out like a sore thumb from it’s surrounding neighborhood. Such as incredibly modern design with such personality.

If you look closely, you can see the “cow family” on the balcony rails that provide this house with that much more personality.



This house exemplifies the creative talents Portland has to offer. Modern yet industrial, the castle house is the perfect example of one family’s willingness to say “why not.”



This house is one of the more artsy and earthy houses that I have seen in the Portland Metro. With such grassroots designs, this house is the epitome of Portland’s organic culture.



Possibly the most iconic, and most well-known house in Portland for being “quirky.”


While there are many homes that were not mentioned on this posting that could have made the list, these were simply some of my favorites that I have seen over my long-time career as a real estate agent in the Portland market.

To say that these houses are “cool and quirky” could not be more of a compliment to the design and features of the home, as they perfectly exemplify the unconventional mindset that Portland has become so notorious for.

We all that one person in the friend group that is a little weird, and I think we can all agree that we find that one house in the neighborhood that is a little weird to be pretty cool.

We like to do things differently here in Portland, and that is exactly what these houses represent, a willingness to bring your original idea to life, to pursue your goals, and to not worry about what others will think of your decisions.

I hope you find this blog fun and entertaining and remember that “It’s A GOOD LIFE!”

Five Star award Winner 2011- 2018 honoring the top 7% of real estate professionals in Oregon.


Rachel Sheller, Principal Broker, Realtor, CRS, ABR, GRI, SRES, Diversity Specialist-HOWNW, Earth Advantage Broker, MASTERS CIRCLE, CSA-Certified Staging Agent, Oregon First, Washington First

Direct 503.380.9634, Email- rachel@rachelsheller.com

View ALL available Houses on the market on my website

Licensed in the State of Oregon and Washington

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