Drive-By Tour of Lake Oswego: Top Sights Along the Way

Gray Shingled Coastal Style Home
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Most of my life has been spent in Lake Oswego, Oregon. It’s the place that has always felt most like home. I grew up there, my husband and I lived there when we were first married, and it’s where we raised our daughters for many years before moving to Eastmoreland, where our son was born.

My parents still live in Lake Oswego, so we often return to visit. Although the houses have changed over time, the neighborhoods still bring back a flood of memories.

I wanted to share a few of the houses we passed while driving through those old neighborhoods last week.

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This one has always been one of my favorite lake houses — charming and timeless.

Lake Oswego

So quaint, isn’t it? It’s just around the corner from a house we lived in when I was in high school, so I used to pass it often — whether by car or by boat.

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Across the lake you can barely make out the home I grew up in. It was such a beautiful place and seeing it across the water always felt special.

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So many memories tied to this lake — afternoons spent on the water, neighborhood strolls, and summer celebrations.

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Red barn doors on garage
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We drove through a neighborhood where we lived with our girls years ago and noticed a house that was for sale. It brought back a lot of memories of life when our children were little.

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The garage on that property looked like a charming guest house from the side — a detail that made the whole place feel especially inviting.

Charming white fence in hedge. Striped awnings.

One former neighbor’s home has appeared on this blog before. I’ve always loved it — it remains as charming today as it was years ago.

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Vines on garage
white modern farmhouse
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The scent of jasmine was everywhere on our drive — I absolutely love that fragrance. Small sensory details like that make familiar neighborhoods feel even more alive.

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Flags with Gate - The Inspired Room

Many homes still flew flags — the Fourth of July is a particularly festive time around the lake, and patriotic displays always add extra warmth to the streets.

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I enjoy these drive-bys, though they often leave me feeling a little homesick for the neighborhoods that shaped my life. Even so, I’m grateful for the many happy memories tied to this place.

Do you ever feel homesick for neighborhoods you think of as “home”?

PS…today is the last day to get my free June Bundle when you grab my favorite essential oils + diffuser set!

More Drive Bys on The Inspired Room:

Highland Park – Dallas Drive By

Magnolia – Seattle Drive By

Queen Anne – Seattle Drive By

Queen Anne + Magnolia Drive By

Summer Drive By in Portland, Oregon

Cannon Beach Cottages Drive By

Or browse more past drive-bys in the blog’s archive.