For old times’ sake — and because I admit to a small obsession — I took a short drive-by while I was in Portland last week. It had been far too long. I began in First Addition in Lake Oswego, a neighborhood where I lived several houses back. I spotted a few homes that made me stop and stare, so here are the highlights.
I had to circle back to the charming home pictured above because impatient drivers kept tailing and honking at me while I tried to take photos. I muttered under my breath that I had important business — clearly I need a bumper sticker that says I brake for charming houses — but the honking continued. I went around the block and tried again.
I love the little details that make this house special: scalloped siding, the arched porch cover with dark wood trim, pretty windows and a picket fence. It’s pure cuteness.
The sign on that picket fence was the sweetest touch.
Lately I’m completely smitten with white houses paired with American flags. It looks so classic and patriotic. The porch chairs add to the welcoming look.
This house won me over with its sunroom — the windows are irresistible. From the side, the porch and composition are just as lovely. I took a closer shot to capture the details; it’s the kind of picture-perfect place that makes you sigh.
Next I drove through my even older neighborhood in Eastmoreland for a mini tour. I had to split that visit in two because the lighting was tricky — too sunny the first time with harsh shadows, and too dark the second time. Good photos were elusive, but a drive-by is always fun regardless. Some of these homes have made appearances in earlier drive-bys.
We featured one of these houses before; it still has a terrific entryway that catches the eye.
This next house is the one I lived in a few homes ago. It was our second “small house” experiment and we squeezed three kids — and often a fourth — into roughly 1,600 square feet (not counting the basement). The rooms were chopped up in that charming old-house way, and with toddlers and preteens under one roof, it felt busy and cozy all at once. I made some creative organizational choices to make it work, and the house is full of good memories.
I adore the little cottage-style homes — the ones with white lights, wreaths, climbing vines, shutters and window boxes. Combine all those elements and I’m practically swooning.
Lead glass and rock details always catch my eye too. The overcast sky made shooting difficult, but that’s part of living in Portland — you can’t always return for the perfect shot.
I also admired a house with stark black window trim that looks so modern against traditional architecture. Another house had double doors and lush landscaping that felt wonderfully inviting; I almost walked right in.
For my final stop, I wandered into a neighborhood marked PRIVATE, MEMBERS ONLY (Waverly Country Club). Normally I’m law-abiding, but when it comes to neighborhood drive-bys I tend to bend the rules a bit. The gate was open, which allowed a quick peek.
Through the trees and beyond a fence I spotted a dreamy, fairytale-like cottage and nearly lost myself. I circled the area trying to get a closer view, momentarily tempted to drive straight through the gate. There were a few cats nearby — perfectly safe and unharmed — and I resisted any rash moves. Getting a better photo would have meant leaving the car and scaling the fence, and since I was in a dress I decided against it. I also hesitated because of a visible security camera; I’d rather not be famous for trespassing. The angle I managed is a tease — charming but just out of reach. Still, believe me when I say it felt magical.
Thanks for coming along on another drive-by!
Enjoy revisiting some past favorites in the drive-by series.