Hillsdale's Housing Boom

[December 17, 2025]

From stand-alone homes to town houses to apartments, Hillsdale is experiencing a building boom that, over the next few years, stands to bring at least 247 new units and anywhere from 500-900 new residents.

New residents could bring a broader base of economic support for Hillsdale’s business district, boost enrollment at public schools at a time of expected shrinkage, as well as add to traffic congestion and parking scarcity.

Project/Location	No. of Units	Parking	Bedrooms
Gooseberry Trails (Habitat for Humanity project) Capitol Hill Rd.	52 attached town-homes	1.1 spaces per unit	Two-five bedrooms
The 1919* 1911 SW Nebraska St.	40 market-rate apartments	None	Studios and one-bedrooms
Vermont* 2423-2429 SW Vermont St.	40 market-rate apartments	Approximately 13	Studios, one- and two-bedroom units
Hillsdale Terrace 6010 – 6028 SW 18th Dr.	9 new stand-alone homes	One two-car garage and driveway per home	4
Hillsdale Highline 5920 SW 18th Drive	7 buildable lots (one completed)	Each home can have a two-car garage	5
Barbur Apartments* 8205 SW Barbur/8050 SW Capitol Hill Rd	149 affordable apartments	45 spaces	1-4
New townhomes on SW 18th at Dewitt	4 townhomes	Unknown	Unknown

Names listed above are based on planning documents and are subject to change. While the name of the future building on Nebraska Street may appear to be a typo, it appears to reference both the address (1911) and its location at Nebraska Street and 19th Avenue; however, clarification was not available at the time of publication.

Business district impact

Brian Carrick, owner of Please Louise restaurant in Hillsdale, said more customers means a more vibrant business district, especially during the evening hours. He is excited at the prospect of more patrons, especially ones who can walk to his Hillsdale restaurant.

Others, like Mike Roach, co-owner of Paloma Clothing, see the increase in building as a welcome ray of optimism on the viability of the local economy, and SW Portland in particular. “It's an unexpected bonus for our area at a time when it doesn't seem like there's that much housing being built around the city, especially at a time of high interest rates,” he said.

Dan Walkowski, president of the Hillsdale Business and Professional Association agreed. “A younger generation is moving in. If we can continue to keep that evolution going, it’s good for Hillsdale.”

Parking concerns

Roach has one caveat: As long as the units come with adequate parking, he sees the new construction as an overall benefit to Hillsdale. While most of the new developments include some amount of parking, at least one 40-unit apartment building has none.

Portland building codes do not require developers to include off-street parking in many mixed-use zone designations. In some situations, building codes limit how much parking a developer is allowed to build. The idea is that new residential developments in areas with nearby amenities and near bus lines with frequent service don’t need as much parking.

Without adequate resident parking, Roach worries that there will be “overflow” to the lots in the business district, which could make it difficult for customers to reach businesses.

As Trimet ridership and bus service decline, the reality in Hillsdale may collide with the best laid plans.

Bike and pedestrian development stalled

Hillsdale is fortunate to host several walking routes developed by the volunteer non-profit SW Trails PDX, however, here also reality may not line up with the desire to provide alternatives to reliance on personal automobiles.

Southwest in Motion, also knows as SWIM, is a plan adopted by Portland City Council in 2019 to improve walking and biking in Southwest Portland. While our population continues to grow, presumably including more people who want to walk and bike, SWIM has not delivered, according to SW Trails’ founder Don Baack. In fact, SW Trails has started their own effort to identify priorities and move projects ahead. They have dubbed this initiative “SWIM & More.”

Two of Hillsdale’s new housing developments are on Capitol Hill Rd, joining a 51-unit apartment complex that was completed in 2024. As Baack notes, sidewalk build-out on at least one side of the street will become more important with higher density in that area.

Plans have been mostly completed for the addition of a few segments of sidewalk on SW Capitol Hill Rd, but none are completely funded. As PBOT officials recently told the  Hillsdale Neighborhood Association, a short segment is slated to be built next year if funding is found.

Impact on Hillsdale schools

Districtwide, Portland Public Schools enrollment is predicted to continue to decline over the next 15 years. It could start to recover after 2040, according to the forecasts. Given this scenario, Hillsdale's three public schools not only can accommodate more students, but will rely on them to maintain robust programing.

Principals at Rieke Elementary and Gray Middle both say they welcome the prospect of more students at their schools—higher enrollment means more funding.

At Robert Gray, falling enrollment has led to the elimination of French and Chinese classes, leaving Spanish as the only language elective option. Said Principal Lisa Newlyn, “The more kids we have at RGMS, the more staff we can have, which means more enrichment options."

“Class size matters,” said Rieke principal Jennie Knapp, “and I want teachers to be able to pay really close attention to meeting the needs of every student in their classrooms.” But, she added, the current class of size of 21 is not too large and "more students per classroom would be fine."

Rieke’s enrollment has fluctuated over the years since opening in 1961 as Wilson Park Elementary School. It was closed as a regular school for ten years in the 80’s and 90’s, then re-opened in 1992 as schools in SW Portland became overcrowded. By the early 2000’s, numbers were falling once more and proposals to close Rieke surfaced in 2003 and again in 2006. From 2003 to 2006, enrollment was around 266.

Community advocacy kept the school open, and enrollment subsequently grew, supported in part by neighborhood efforts to highlight Rieke and its strengths as a community-based school. (For a review of Rieke’s history and advocacy, see the unofficial record at riekeschool.blogspot.com.)

Predicted enrollment of Hillsdale public schools over the next 15 years

	2025-26 Enrollment	Projected Low	Projected High	Historic Capacity
Rieke Elementary	275	262	245	approx. 465
Robert Gray Middle	434	332	430 (2027-28)	approx. 622
Ida B. Wells High	1517	1,284	1,568 (2026-27)	The Wells rebuild is planned for a capacity of 1700

Gray and Wells each have a larger attendance boundary than Rieke. Their enrollments will be further bolstered by any additional housing growth outside of Hillsdale, including at the former Alpenrose Dairy, which is currently being developed for 263 new stand-alone houses and townhomes.

On SW 18th Dr., new sidewalks are interrupted by a barrier at the border of the two lots; new townhomes across the street on the corner of 18th and Dewitt; the construction scene next to Sasquatch Brewing Co.; a rendering of the new building coming to Vermont St.

—Valeurie Friedman

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