Trailside
A rare opportunity on Bend's coveted west side, this charming cabin-style home has a current short-term rental permit. Many great options as an exceptional investment, second home, or full-time residence. Ideally located among the pines just minutes from the Cascade Highlands Trail system, The Grove, Sparrow Bakery, and endless west-side amenities. The main-level primary suite offers convenience and privacy, while the vaulted great room is filled with natural light and centered around a cozy fireplace. Wood-wrapped windows, rich wood trim, and updated wood flooring add warmth and character throughout. The kitchen features stainless steel appliances, an eating bar, and an open layout perfect for entertaining. Relax in the private hot tub after a day on the trails or slopes. Complete with a 2-car garage and EV charger, this is the ultimate Bend lifestyle property with proven investment potential.
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Loan amount $680,000 · $170,000 down · 30 year term
Monthly cash flow, cap rate, and cash-on-cash return at this price. Adjust the numbers to your own financing and rent.
Estimate $2,336 ($2,100–$2,675) · HUD Fair Market Rent (FY2025), Deschutes County, 3BR. Edit to your own number.
At $850,000 with 20% down, this property runs $3,207 per month negative. Adjust the price, down payment, or rent to find what works.
Estimates only, not investment advice or a guarantee of rent, value, or return. Figures depend on the numbers you enter and current market conditions. Verify with your lender, tax advisor, and a Ryan Realty broker before you rely on them.
Listing courtesy of The Agency Bend, agent Tab Howard, 541-508-7430
Data last updated August 13, 2026
Based on information from Oregon Data Share. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listing information is for consumers personal, non-commercial use only.
Source: Spark MLS. Active inventory.