When it comes to fantasizing about living in a swanky midcentury, Portland has a lot to offer. As of a few days ago, we can add this updated 1960 home to the list. Located in Hessler Heights in the Hillsdale neighborhood, it has the expected vintage character, like a low-slung roof, deep eaves, and big picture windows. That's all combined with interior updates that read both era-appropriate and casually cool. Plus, there's a pool.

The recent upgrades include much needed items like windows, skylights, sewer line, gas generator, water heater, and new garage door, but we're more dazzled by the understated glam that's apparent as soon as you walk inside the dimpled glass entry. There, find the foyer encased in silver metallic embossed wallpaper with a bird and floral motif.

This gives way to the main living areas, including the living room and its wood-paneled accent wall and fireplace with a chunky stone surround. In true Mad Men fashion, it has inset doors that swing open to reveal a chic little wet bar, with open shelves staggered for different styles of glassware and good lighting for mixing drinks.

The nearby kitchen reveals terrazzo floors and Hermes-orange cabinetry with circular brass pulls (all more recent additions than their throwback vibes would suggest). But this room isn't only about looks—there's plenty of storage, counter space, and a convenient butler's pantry. A cased doorway leads to a nearby family room covered in tongue-and-groove wood from walls to beamed ceiling, more tall windows, and glass doors to the backyard.

There's a powder bathroom on this level, also with a fun metallic wallpaper that goes with the preserved midcentury vanity, as well as two bedrooms, including the primary suite. The latter has a walk-in closet, as well as an updated bathroom with a soaking tub under a skylight and a generous vanity. While the lower level, with two more bedrooms, a full bathroom, and the laundry, is a little more bare bones when it comes to style, it has the same high ceilings, wood floors, big windows, and abundant storage as is found upstairs.

The midcentury lifestyle prioritized the outdoors as much as the interior, and this property is no exception, although here it takes the form of a veritable spa in the backyard. With a half-acre, south-facing lot, it has an in-ground heated pool, a sauna, and Ipe decks galore for general lounging and taking in the sunset. If you need a little more sweat, enjoy the private neighborhood pickleball/tennis court a short walk away.

Listing Fast Facts 

• Address: 1550 SW Mitchell St, Portland, OR 97239
• Size: 4,024 square feet/4 bedroom/4 bath 
• List Date: 6/5/2026 
• List Price: $1,775,000
• Listing Agent: Marisa Swenson, Modern Homes Collective

Melissa Dalton is a freelance writer who has focused on Pacific Northwest design and lifestyle since 2008. Contact Dalton here. 

Editor’s Note: Portland Monthly’s “Property Watch” column takes a weekly look at an interesting home in Portland’s real estate market (with periodic ventures to the burbs and points beyond, for good measure). Got a home you think would work for this column? Get in touch at [email protected].