For old time’s sake — and because I have a genuine addiction to pretty houses — I went on a little drive-by while I was in Portland last week. It had been far too long. I started in First Addition in Lake Oswego, a neighborhood I used to visit years ago. I found a couple of houses that made me stop and stare, so here are the highlights.
I had to circle back by the charming house above twice because impatient drivers kept pulling up behind me. I muttered under my breath that I had Very Serious Business admiring homes (I need a bumper sticker that says “I brake for charming houses”), but the honking continued. So I drove around the block and tried again.
I adore the small details that give this house personality — the scalloped siding, the arched porch cover with dark wood trim, the pretty windows and the picket fence. It’s one of those homes where every element feels deliberately sweet.
Even the sign on the picket fence is delightful. Lately I’m completely smitten with white houses dressed with American flags; they feel both classic and welcoming. The porch chairs add to the inviting scene.
This house captivated me with its sunroom. Look at those windows — they’re the kind that make you want to sit inside with a book and a cup of tea.
I drove around the side to admire the porch from another angle, and it was just as lovely. A closer look reveals even more charming details. It’s the kind of picturesque home that makes you sigh in appreciation.
Next I headed to my old neighborhood, Eastmoreland, for a mini drive-by. I had to split this visit into two sessions because of tricky light: too sunny and shadowed the first time, then too dark later. In the end the photos weren’t perfect, but the visit was still enjoyable. Some of these houses have appeared in my past posts, and it’s always fun to revisit them.
We’ve looked at one of these homes before — the entryway is really striking and worth admiring again.
I also drove by my old house — not the most recent one, but the one before that. It was our second small-house experiment, where we managed life with three kids and often another in tow. The main living area was around 1,600 square feet, and like many older homes it felt chopped up. With two little ones and two nearly-teenagers, it could be a bit chaotic, but it generated so many good memories and forced me to get super creative with organization.
There’s a little house I’ve shown before that I just can’t resist. Even my new photo didn’t capture it as well as I’d hoped, so I’m sharing a previous shot. The combination of tiny white lights, wreaths, climbing vines, shutters and window boxes makes it irresistible.
I’m always partial to rock and leaded glass details too. That day the sky was dreary, which muted the photos — one disappointment of not living in Portland anymore is that I can’t easily go back for a better light-filled shot.
Another house caught my eye with its black window trim; the contrast is crisp and elegant. Nearby, a home with double doors and thoughtful landscaping felt so welcoming I almost invited myself in.
For my final stop I drove into a neighborhood marked PRIVATE, MEMBERS ONLY (Waverly Country Club). Normally I follow rules, but when it comes to admiring houses from my car, I admit I’m more daring. Luckily the gate was open so I could peek a little.
Through the trees and behind a picket fence I spotted a dreamy fairytale cottage that made my heart leap. I circled slowly, trying to find a better angle. I nearly went through the gate in my excitement and joked that I might have run over three kitties — they were fine, of course, and no animals were harmed. I debated getting out to scale the fence for a better photo, but wearing a dress and spotting a security camera made me think twice. This view felt tantalizingly close yet just out of reach — the kind of glimpse that’s equal parts torture and delight.
Trust me when I say it was magical.
Thanks for coming along on another drive-by!
If you enjoyed this, look back through past drive-bys to relive more neighborhood discoveries and charming homes.