Five Oak Building Sold: What $125 Million in Downtown Portland Investment Signals for the Market
The Five Oak Building at 421 SW Oak St. has a new owner — and the deal says a lot about where downtown Portland is heading.
Jeff Swickard, who already owns the U.S. Bancorp Tower (Big Pink), purchased the 266,664-square-foot office building through a competitive bidding process, as reported by the Portland Business Journal. The eight-story building had been foreclosed on by Nuveen in 2024 over a delinquent loan with an outstanding balance of $44.2 million. It was originally built in 1944, renovated in 2005, and currently houses several Multnomah County offices.
With this acquisition, Swickard’s downtown Portland investments now total roughly $125 million in under a year — 25% more than originally announced. That kind of capital moving into a single submarket, from a single investor, in that short a window is a strong signal.
What This Means
For tenants and occupiers: When well-capitalized ownership takes over distressed properties, buildings improve. Expect upgraded common areas, better property management, and a more competitive tenant experience at Five Oak — especially given Swickard's hospitality-driven vision for the neighboring U.S. Bancorp Tower. Tenants in the market should be watching how repositioned assets like this change the landscape of options downtown. There may be opportunities to negotiate favorable terms in a building that's actively trying to attract and retain tenants.
For landlords and investors: This is the clearest buy signal downtown Portland has seen in years. A foreclosed asset moving through a competitive bidding process — not a quiet off-market deal — tells you there's real demand for well-located office product, even in a market still working through elevated vacancy. It also reinforces a trend: experienced operators are stepping in where institutional capital pulled back. If you're holding downtown assets, this is validation. If you're considering a disposition, the buyer pool may be deeper than you think.
The Bigger Picture
Downtown Portland's office vacancy remains elevated (15.1% as of Q4 2025), and challenges around public safety and livability haven't disappeared. But $125 million in investment from a single source — backed by public support from Mayor Keith Wilson — signals that the recovery narrative is gaining real traction. The gap between distressed pricing and long-term value is where smart capital moves, and that's exactly what's happening here.
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