Property Watch: Readers’ Favorite Homes on the Market in 2024

The SE Belmont Victorian that was long home to the Pied Cow sold a week into 2024, but the story about its availability was still one of the most read Property Watch columns of the year.
While it’s always interesting when Portland real estate gets national press coverage—ahem, the recent headlines that the city will become a million-dollar housing market in 10 years—here at Property Watch, we are more interested in appreciating the local variety, whether we’re touring fanciful mansions, midcentury “treehouses,” or penthouses in old candy factories. These are the 2024 listings that grabbed our readers the most, how much they sold for, and if any are still available.

10. First-Ever Sale of Midcentury ‘Treehouse’
Hillsdale
It’s true that calling this a “treehouse” was not technically correct, but how else to describe the feel of the living room in this 1966 home cantilevered over a sloping lot above Hillsdale, with its big picture windows framing the trees and cedar tongue-and-groove on the walls. Buyers liked it, too, seeing as how it went for $135K over asking.
Status: Sold for $985,000 on 3/13/2024, after being listed for $850,000 on 2/15/2024.

9. An Adorable Ranchelow in Portland’s ‘City Within a City’
Maywood Park
This was our first foray into Maywood Park, the Northeast neighborhood that became a city in its own right, in a 1967 vote to fight the state’s intent to put the Interstate 205 through it. This 1942 “ranchelow” had lots of space (3,465 square feet on 0.28-acre); great amenities, including a ’70s-era sauna, quintessential basement rec room, and detached art studio; and some pretty bungalow detailing, like coved ceilings and mahogany millwork.
Status: Sold for $725,000 on 8/26/2024, after being listed for $749,000 on 7/11/2024.

8. Portland’s Most Fanciful Historic Mansion for Sale
Dunthorpe
This 1922 mansion on 2.99 acres in Dunthorpe has always been a little hard to describe, probably because it was designed by the original owner, Percy A. Smith, to be a fanciful combo of children’s adventure tales and European manor. From the weird to the wonderful, it seemed to have a little of everything, like Latin inscriptions carved into the woodwork and chiseled grotesque faces in the Hogwartsesque speakeasy.
Status: Sold for $3,350,000 on 4/5/2024, after being listed for $3,500,000 on 10/27/2023.

7. Classic Midcentury from a ‘Big Deal’ Architect
Dunthorpe
This was our introduction to Van Evera Bailey, who was a much-loved and lauded midcentury architect working in the Northwest Regional style. We admired this house’s wood ceilings, park-like grounds with pool, and nautical elements, such as the way the carport’s beefy stilts made it feel like the living room above it was floating in the trees.
Status: Still listed as of 12/23/2024 for $2,495,000, after being listed for $3,195,000 on 7/31/2024.

6. A Luxe Penthouse in an Old Candy Factory
Pearl District
Erected in 1904 for a candy manufacturer and converted to condos in 1999, this is one of the earliest buildings in the 13th Avenue Historic District—and still has the faded signage on the brick exterior to show for it. This top-floor penthouse had 1,881 square feet over two floors, main rooms with far-reaching views, and an excellent 480-square-foot outdoor terrace.
Status: Sold for $1,100,000 on 3/15/2024, after being listed for $1,100,000 on 2/2/2024.

5. Pied Cow’s Famed Victorian Goes on the Market
Sunnyside
This 1893 Queen Anne Victorian has been an institution in the Sunnyside neighborhood for decades. Located at the edge of the commercial district between 33rd and 35th on SE Belmont Street, it was saved from teardown by Jerry Bosco and Ben Milligan in the ’60s, later becoming the Pied Cow Coffeehouse in 1991, and now, is home to tapas bar and café Foxtrot.
Status: Sold for 1,370,000 on 1/8/2024, after being listed for $1,500,000 on 8/25/2023.

4. A Rare Art Deco in Southeast
Eastmoreland
This is a spec house built in the Eastmoreland neighborhood in 1937. Designed in the modernistic style by well-known architect Roscoe Hemenway, the builder had plans to fill the area with similar-looking houses—think rounded corners and Deco details—until World War II brought construction to a halt, making this one of two instead.
Status: Sold for $833,000 on 7/3/2024, after listing for $885,000 on 2/29/2024.

3. A Speakeasy, plus an Enormous Ranch on an Enormous Lot
Argay Terrace
Just a nicely updated ranch house in Northeast Portland, complete with double-size lot, 500-square-foot garage, swanky finishes (terrazzo, quartz, and brushed brass), and a basement speakeasy.
Status: Sold for $785,000 on 4/1/2024, after listing for $785,000 on 2/22/2024.

2. The Longtime Residence of a Visionary Portland Architect
Raleigh Hills
The Jorgensen House was built in 1939 but everything about it feels ahead of its time. That’s because it was designed by John Yeon, renowned, self-taught architectural designer and conservationist, who is considered one of the founders of the Northwest Regional style of modernism. His innovation is everywhere here, from the color palette (‘Yeon Blue’) to the built-ins and lighting. Although Yeon originally designed the home for a photographer, he loved it so much that he bought it for himself and lived there for decades.
Status: Sold for $1,679,000 on 7/10/2024, after listing for $1,679,000 on 4/29/2024.

1. Is This the Oldest House in Portland?
Bridlemile
This listing comes with a little mystery. It has 2.86-acres in the Bridlemile neighborhood marketed for development. But also: a little red house on the corner of SW Shattuck Road and Hamilton Street called the Tigard/Rogers House, which architectural historians believe could be the oldest house in Portland. There’s been no buyer yet, so the future remains unclear.
Status: Still listed as of 12/23/2024 for $1,020,000, after being listed for $2,693,670 on 2/13/2024.
Melissa Dalton is a freelance writer who has focused on Pacific Northwest design and lifestyle since 2008. She is based in Portland, Oregon. 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].
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