For the love of it — and because I can’t resist — I went on a short neighborhood drive-by while I was in Portland last week. It had been far too long. I began with a quick loop through First Addition in Lake Oswego, where I used to live several houses back. I discovered a few charming homes worth sharing, so come take a look.
I had to circle back to the house above because impatient drivers kept closing in behind me. I quietly told them I had important business — admiring houses — but the honking continued, so I went around the block and tried again.
I adore the details on this home: scalloped siding, an arched porch cover with rich dark wood trim beneath, pretty windows, and a tidy picket fence. Everything about it is delightfully quaint.
The little sign on that picket fence is just perfect.
I’ve been especially taken with white houses lately, especially when paired with American flags. It feels patriotic and classic. The porch chairs add to the welcoming, relaxed vibe.
This place won me over with its sunroom — those windows are incredible.
I drove around to the side to get another angle, and the porch looked just as lovely from there.
Zooming in reveals even more charm.
It’s a picturesque scene that makes you sigh with appreciation.
After that, I headed to Eastmoreland for a mini-drive-by. I had to split that visit into two attempts because lighting was tricky: the first pass was too sunny with heavy shadows from the trees, and when I returned it was getting too dark for good photos. Still, a drive-by is always enjoyable, and many of these houses are familiar from past outings.
We looked at this one on a previous drive-by — such a striking entryway.
This next house is one of my former homes — not my most recent, but the one before that. It was our second small-house experiment, and for a time we were living there with three kids and often an extra child. The main living area (excluding the basement) was around 1,600 square feet. It wasn’t tiny, but like many older houses it was compartmentalized, which made life with babies and teens quite lively.
I have so many fond memories of figuring out how to make that space work. It pushed me to get creative with organization.
I love this little house and have shared it before. My newer photo didn’t do it justice, so I’m reusing a better shot — it’s just too cute to skip.
Little white lights, wreaths, vines, shutters, and window boxes — all together on one house — make my heart melt.
There’s something timeless about rock and leaded glass. The overcast sky made the scene a bit dreary, which is the one downside to not living in Portland anymore: I can’t just pop back for a perfect sunny shot.
I’m also fond of the black window trim on this home; it adds crisp contrast.
The double doors and thoughtful landscaping make another house feel very inviting. I almost invited myself in.
For my final stop I drove into a neighborhood with a “Private, Members Only” sign — Waverly Country Club. Normally I follow the rules, but I confess I ignore private signs when house-spotting. Luckily the gate was open enough to peek through.
Through the trees and beyond the fence I spotted a fairytale-like cottage that made me do a double take. I circled slowly, hoping for a better view. I nearly edged too close in my excitement, fearful I might accidentally run over some resident cats from how transfixed I was — don’t worry, the cats were safe. I did not, in fact, run over any kitties.
There wasn’t a good way to get a closer photo without leaving the car or getting too close to the gate, and I was in a dress, so I left it be. I also steered clear of any security cameras to avoid trouble. The glimpse I got was tantalizing but not enough to fully appreciate the cottage’s charm, which was mildly frustrating.
Trust me when I say it truly felt magical.
Thanks for coming along on another drive-by!
Want to revisit some favorites from past outings? Find the drive-bys in the site’s archive.