
Listing courtesy of Cascade Hasson SIR, agent Brian Ladd
Data last updated June 23, 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.
Avoid the uncertainty of Bend's changing short-term rental regulations. Trailhead Cottages offer a rare solution with deeded short-term rental rights that transfer with the property. Located directly across from Tetherow's pool, fitness center, golf course and dining, these homes provide immediate access to miles of mountain biking and hiking trails as well as the most direct route to Mt. Bachelor and the Cascade Lakes. This home is designed for efficiency and maximizes every inch, offering two king suites, a comfortably sized kitchen, and plenty of gathering space. The rear deck is equipped with a hot tub and fire pit and has long ranging views to the south. Plus since it is being sold fully furnished with all the necessary housewares, it is ready for immediate use. This is a turnkey opportunity to own a high-performing asset in one of Bend's premier resort destinations. They are move-in ready and built for the Central Oregon lifestyle.
A rough estimate, not a quote. A real number comes from a lender.
Loan amount $767,000 · $192,000 down · 30 year term
Monthly cash flow, cap rate, and cash-on-cash return at this price. Every number is an estimate you can adjust to your own financing and rent.
Estimate $1,667 ($1,500–$1,925) · HUD Fair Market Rent (FY2025), Deschutes County, 2BR. Edit to your own number.
At $959,000 with 25% down, this property runs $3,901 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.
We pull climate risk data from FEMA flood maps, the Deschutes County wildland-urban interface map, and NOAA heat trends. Detailed scoring for this property is on request.
Get the climate reportWe compute vacation rental projections from comparable short-term rentals in the same community, weighted by bed count, view, and amenities. A custom projection for this property is on request.
Get the rental projectionBrowse current listings with a full video tour. See the flow, the light, and the lot before you book a showing.