
Shortstack Belmont: The developers behind Shortstack and their collaboration with OHCS
In the heart of Southeast Portland’s Buckman neighborhood, something more than just housing is taking root. Shortstack Belmont — a thoughtfully designed, 35-unit multifamily development — is helping fill Oregon’s critical “missing middle” housing gap and telling a larger story about what’s possible when vision, values, and partnership align.
Shortstack Belmont is a collaboration between Jessy Ledesma of HomeWork Development and Anna Mackay of Sister City. Both launched their firms during the pandemic after working for other Oregon-based developers. Sharing a commitment to inclusive and missing middle housing, they teamed up to form Shortstack, a replicable, mass timber housing platform designed to provide moderately priced homes for households earning too much to qualify for traditional subsidies but too little to afford market rents.
The Belmont project is the third to emerge from the Shortstack team and delivers what so many communities say they need but don’t always get at affordable prices: family-sized, energy-efficient apartments located within walking distance of schools, parks, grocery stores, and transit. Think two- and three-bedroom units priced for households earning 60-80% of the area median income, a true sweet spot for essential workers and families being squeezed out of Portland’s core.
The project’s success hinges in part on a $6 million award from Oregon Housing and Community Services (OHCS) through the LIFT program which is funding accessed through the agency’s newly launched Oregon Centralized Application (ORCA) process. For Mackay and Ledesma, the ORCA process marked a welcome evolution in how state funding can be accessed.
“As a developer who has worked through years of OHCS funding cycles, I really appreciate the updated ORCA process,” Ledesma shared. “It’s clear, flexible, and helped our team to stay on track. The Procorem system let us ask questions directly in the portal and staff were supportive at every stage.”
It’s a small but meaningful shift in how government supports housing developers— not just as funders but as true partners in a process designed to get good projects over the finish line.
“We know the funds are limited, and the need is great,” Mackay added. “It’s not an easy job to stretch resources fairly, and we appreciate the effort of OHCS to establish the ORCA process.”
From construction methods to community engagement, Shortstack Belmont reflects a different kind of development ethos. The project uses mass timber, a sustainable and locally sourced material, and is built on a panelized system designed for replication. More than 30% of contractors and 70% of consultants are COBID-certified (state-recognized minority-, women-, and veteran-owned small businesses). Additionally, the team partnered with NAMC-Oregon to help educate minority contractors about bidding opportunities in this emerging construction type.
Yet even with the innovation, the path wasn’t without hurdles. As with any urban infill development, navigating Portland’s layered permitting process and dealing with site-specific conditions presented challenges. Rising operational costs, especially acute for small and mid-sized developers, also pose a challenge.
That’s where the Shortstack model offers a potential blueprint: by designing replicable systems and spreading costs across multiple sites.
By the time Shortstack Belmont is completed in mid-2026, the team’s replicable model will be responsible for delivering 108 new units of moderate-income housing to Portland. But the real story may be what’s being built beneath the surface: a framework for more inclusive development, supported by policies like ORCA and powered by development teams dedicated to thoughtful housing production. As Oregon continues to address its housing crisis, Shortstack Belmont offers a grounded, hopeful glimpse of what can happen when smart policy meets values-driven action.

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