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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. (Interior photos are of a similar unit.)
A rough estimate, not a quote. Loan amount $767,200 · $191,800 down · 30 year term.
Insurance starts at $1,000 per $300K of price each year. Type your quote to replace it.
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Neighborhood
Tetherow began in 2004 as a plan called Cascade Highlands. A year later, the developers renamed it Tetherow, after Solomon Tetherow, the wagon party captain who led a pioneer group through this stretch of Central Oregon in the mid-1800s. The golf course and clubhouse opened in 2008, and the resort built out in stages after that: the Tetherow Grill in 2009, a golf academy in 2012, The Row in 2013, the 50-room Tetherow Lodges hotel in 2014, an event pavilion and the first vacation rental homes in 2016, and Tetherow Sport in 2017. What exists today across the 700-acre master plan is roughly 400 custom homesites split into nine named sub-neighborhoods, from the golf-course estates in Heath and Crescent to the attached townhomes at The Rim and Triple Knot.
The course is a David McLay Kidd design, and Kidd is not a name Tetherow borrows for marketing. He designed Bandon Dunes on the Oregon coast in 1999, the course that proved a Scottish-links layout could work on American ground, and he has lived in Bend ever since, running his design firm, DMK Golf Design, from here. Tetherow was his attempt at a High Desert version of the same idea: firm turf, fescue fairways, and a course that plays on the ground as much as through the air. It has since climbed 25 spots on Golf Digest's public-course rankings and held the top Pacific Northwest resort spot in Conde Nast Traveler's reader poll for eight straight years.
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| Date | Event | Price |
|---|---|---|
| Jun 23, 2026 | Listed | $959,000 |
$916 per sq ft
61 days on market. Tetherow median to pending is 51 days.
HOA $664 per month. Tax $470 per year.
The full analysis names every comparable sale and shows the adjustment we made for each one.
Listing fields from Spark. Place median from the live pulse. This is an estimate, not an appraisal. It is not a guarantee of price. See our terms.
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Monthly cash flow, cap rate, and cash-on-cash return at this price. Adjust the numbers 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 20% down, this property runs $4,640 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 Cascade Hasson SIR, agent Brian Ladd, 541-383-7600
Data last updated September 1, 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.
Charted at Bend (city) scope
Aug 2024 to Jul 2026 (24 months) · Market Truth leftover, Bend city, monthly median close. Completed months only.
This home is listed at $959,000, 59.6% below the Tetherow median list price. See full Tetherow market →