Property Watch: Readers' Favorite Homes on the Market in 2023
Profiling real estate in Portland for the Property Watch column takes us inside a wide variety of homes, from small, turn-of-the-century bungalows to swanky midcentury pads in the burbs with their own peninsula. Read on to see which houses our readers liked most in 2023, how much they sold for—and which are still available.

10. Become an Urban Homesteader
St. Johns
Looks like the dream of becoming an urban farmer is alive and well, judging by the popularity of this North Portland listing. It included not just a 1914 Craftsman house, but chicken and alpaca enclosures, two Airstreams, an 813-square-foot shop, and a hidden 0.45-acre lot behind the house, empty and ready for small-scale agriculture.
Status: Sold for $886,320 on 11/1/23, after being listed for $799,900 on 10/6/23

9. This 1885 Victorian Is One of the Oldest Homes in Portland
Northwest District
This was the last home of Jerry Bosco and Ben Milligan, Portland’s pioneers in architectural preservation, whose work lives on in the Architectural Heritage Center. Located in Northwest’s Alphabet District, the house, now a sprightly 138-year-old, has a lovely ornate façade that contrasts with its more pared-back interiors.
Status: Sold for $1,130,000 on 5/5/23, after being listed for $1,125,000 on 3/31/23

8. Your Own $7 Million Peninsula with a Midcentury Remodel
Lake Oswego
Designed by architect Kenneth G. Walter, built in 1965, and extensively remodeled in the interim, this Lake Oswego pad retains its midcentury swagger with details like a sunken terrazzo soaking tub, but also embraces a modern sensibility via a new kitchen, updated bathrooms, and a Tesla power wall. With 213 feet of lake frontage, plus its own dock and boathouse, and a downstairs “party room,” it’s also a permanent vacation.
Status: Currently listed for $7,200,000, on market since 6/7/2023

Image: Courtesy Mark McHugh
7. The Only Red Brick Townhouses in Oregon
Northwest District
New York City and Philadelphia have more than their fair share of historic townhouses, whereas Portland, not so much. The ones we do have are typically constructed of wood, making this listing a veritable unicorn: according to historians, it may be the only example of a brick townhouse in the entire state of Oregon.
Status: Sold for $940,000 on 9/27/23, after being listed for $970,000 on 5/25/2023

6. A North Portland Bungalow with a Showstopping Kitchen
Arbor Lodge
This 1911 bungalow favors the past, present, and future. It has many of the earmarks of its historic type—think tall ceilings, wood floors, standard bungalow layout—spruced up with a lovely kitchen remodel. With such a big lot, it is ripe for development opportunities.
Status: Sold for $585,000 on 3/3/23, after being listed for $559,900 on 2/8/2023

5. One-of-a-Kind Home by an Iconic Oregon Architect
Forest Park
This is a spec house like no other: an entirely original, custom design from iconic local organic architect Robert Harvey Oshatz. It will be the first home in an exclusive collection of five, called Oshatz Wood, a development on 90,000 square feet in the Forest Park neighborhood where buyers can work one-on-one with the architect to personalize the interior.
Status: Currently listed for $2,695,000, down from $3,600,000, on the market since 9/18/2022

Image: Courtesy Mark McHugh
4. A Pretty and Pastoral Ranch on Sauvie Island
Sauvie Island
For-sale properties on this Willamette River isle just northwest of Portland aren’t common finds, and this one hit a sweet spot, thanks to a lot of space, both inside and out: a 4,048-square-foot refreshed ranch on two acres, complete with gardens, goats, outbuildings, horseshoe pit, zip line, hot tub, and fire ring.
Status: Sold for $1,600,000 on 6/15/23, after being listed for $1,695,000 on 3/9/2023

Image: Courtesy 360PDX
3. Tabor’s Most-Famed Midcentury Hits the Market
Mount Tabor
Built in 1958, this midcentury home underwent a 2016 remodel by a local dream team—including Risa Boyer Architecture, JDL Development, and Lilyvilla Gardens—and has garnered a lot of attention ever since. Its dramatic makeover, including vaulted living room ceilings and a new glass façade for appreciating the 180-degree views, are worth talking about.
Status: Sold for $2,544,470 on 11/7/23, after being listed for $3,000,000 on 4/29/2023

2. First-Ever Sale of the Geometric ‘Hippie House’
Gleneden Beach
The owner of this custom 1970 Oregon Coast house was once quoted as saying: “Who says that walls have to be straight?” Rhetorical questions aside, the free-form, geometric design by Portland architect Don Vallaster does indeed have angled walls galore, giving it an organic shape that’s meant to blend into the natural environment.
Status: Currently listed for $759,000, on market since 6/10/2023

Image: Courtesy AJ McGarry
1. Portland’s Only Castle Is for Sale
Southwest Hills
The local landmark known as “Piggott’s Castle” was inspired by a flip through a book called A Pictorial History of the World, in which Charles Piggott saw a picture of a castle on one of Rome’s Seven Hills and decided to copy it. Built in 1894, it has 11-foot-high ceilings, a crenellated parapet, and a tower room that’s since been converted into a sauna.
Status: Listed on 5/1/2023 for $1,500,000, and then taken off market
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].