Three Reasons Buyers Are Moving to Bend and Redmond — and One Rule That Ends the Airbnb Plan
Reason one: the lifestyle, which is not a marketing line
Central Oregon buyers are not really buying a house. They're buying the weekend.
Mount Bachelor in winter. Smith Rock in spring, fifteen minutes from Redmond. The Deschutes running through the middle of everything. Roughly three hundred days of high-desert sun, which is a shock to anyone arriving from the west side of the Cascades. Trail networks that start where the subdivisions end.
This has been the most durable driver of the Central Oregon market for a decade, and it hasn't softened. Migration from higher-cost West Coast cities has continued as remote-work flexibility lets buyers prioritize lifestyle and outdoor access over commute distance. Even with remote work growth slowing nationally, professionals keep relocating out of expensive metros, and the region — Bend, Redmond, Sisters, Sunriver, La Pine — keeps attracting both retirees and working households.
What that means for you as a buyer: demand here is not speculative. It's structural. That cuts both ways. It supports your resale value, and it means you should not expect to find a bargain simply by waiting.
Reason two: the math still works — especially sixteen miles north
This is where most people's assumptions are out of date.
Bend's median sale price has been running comfortably above $700,000, bouncing between roughly $700K and $731K through late 2025 and into January 2026. Redmond's median, as of early 2026, sits in the high $480s.
That is roughly a $200,000 gap between two cities sixteen miles apart, and it is the single biggest force shaping where new arrivals actually land. Redmond has quietly become Deschutes County's fastest-growing city. It draws first-time buyers and move-up households who want more house and more yard for the money, and it has more developable land than Bend, which has supported new-construction communities — useful if you'd rather buy something with a warranty than inherit somebody's 1978 roof.
The tradeoffs are real and worth saying out loud. Redmond is flatter and less scenic than Bend's westside. The restaurant scene is thinner. You are trading some amenity density for a materially lower entry price and a shorter path to homeownership.
Two other numbers that surprise people:
Property taxes. Oregon's Measures 5 and 50 cap assessed value growth, so your effective rate is applied to assessed value, not market value. A $500,000 Redmond home often carries an annual bill in the $3,500–$4,200 range — lower than comparable homes in Washington or Idaho.
No statewide sales tax. It shows up repeatedly in surveys of why people relocate to Oregon, and it compounds over the years you own.
Reason three: this is a calmer market than the one you've heard about
The frenzy is over, and that's good news for a buyer.
Bend's year-over-year price growth has been running somewhere between flat and about 1.6%. Forecasts for 2026 range from roughly 1% to 4% appreciation, with some analysts expecting prices to stay essentially flat as inventory and demand find balance. This is stabilization, not decline.
The more useful signal is behavioral. A few years ago homes were closing at 105% of list. Today sellers negotiate. Buyers are taking time to compare neighborhoods and understand value instead of writing out of fear. Demand hasn't dropped — it's become selective.
Practically: you can ask for repairs. You can include an inspection contingency and keep it. You can look at a house twice. In 2021 none of that was true here.
Now the alert: Bend's short-term rental rules will surprise you
Here is the part that costs people money.
A large share of out-of-state buyers arrive with some version of the same plan — buy the house, rent it out short-term when we're not using it, let the bookings carry part of the payment. In Bend, that plan works far less often than people assume, and the reason is structural, not bureaucratic.
Bend regulates short-term rentals through Development Code section 3.6.500 and Bend Code Chapter 7.16. The rules split into two categories, and which one you fall into determines everything.
Type I — the accessible category
Type I covers owner-occupied rentals where two or fewer bedrooms are rented and the owner occupies the home during the stay; infrequent whole-home rentals available fewer than 30 days per calendar year, or up to four rental periods; and whole homes in commercial and mixed-use zones. Type I is not subject to the concentration limits.
Type II — the one investors actually want
Type II covers whole-home, non-owner-occupied rentals in residential zones — including ADUs used as short-term rentals. This is what most people picture when they say "we'll Airbnb it."
And Type II is subject to Bend's signature rule.
The 500-foot separation rule
Bend requires at least 500 feet of separation between properties with a valid Type II short-term rental permit or application, measured radially from the property boundary. If a neighboring property inside that radius already holds one, your property is ineligible — regardless of how well-suited the house is or how much you're willing to pay.
The city's own estimate is that this single rule makes more than half of Bend's residential properties ineligible for a whole-home short-term rental permit. In neighborhoods already saturated with permits, no new ones are being issued at all.
The detail that catches buyers: the permit follows the owner
This is the one I want you to remember.
Any short-term rental application submitted after April 15, 2015 is specific to the owner of the dwelling unit for which it was issued. Permits are not freely transferable.
So when a listing says "turnkey short-term rental, established booking history" — that's a description of the seller's business, not a description of what you're buying. You may have to apply fresh, and a fresh application is judged under today's rules, buffer included. If the surrounding blocks filled up between 2015 and now, the door may already be shut.
What to do about it: make short-term rental eligibility an explicit contingency in your offer, and verify it directly with the City of Bend before you remove that contingency. Not from the listing remarks. Not from the seller's assurance. In writing, from the city.
Two permits, and both have to stay alive
Operating legally in Bend requires a land use permit — the zoning approval attached to the property — and an annual operating license. If you fail to secure the operating license within the required timeframe, the land use permit is voided, and you reapply under whatever rules are current at that moment, including the 500-foot buffer. Room tax reports and payments are filed monthly or quarterly depending on your revenue.
Enforcement is not theoretical. Bend's code enforcement team compares live Airbnb and VRBO listings against the city's licensed-rental database specifically to identify unpermitted operators.
Redmond has its own rulebook
Do not assume the Bend rules travel. Redmond regulates short-term rentals under City Code Chapter 7.132 and following, and treats anything under 30 consecutive days as a short-term rental. Requirements include:
A city business license obtained before any rental of the property, with renewals due each January
One off-street parking space provided for the rental, in addition to normal onsite parking requirements
Occupancy capped at three people per bedroom, counting anyone over the age of three
A named local responsible party who lives in the vicinity of Redmond and serves as the contact for issues
Maximum occupancy and the city's Good Neighbor Guidelines posted inside the rental
Compliance with noise, litter, odor and solid waste rules, including weekly waste pickup year-round
If the business license fee or transient room tax payments run 30 days past due, the permit can be revoked.
Sunriver, Sisters, and unincorporated Deschutes County each operate under separate frameworks again. Sisters has also moved toward density-based limits. The rule that applies is the rule of the jurisdiction the parcel sits in — not the county, not the region, not what your neighbor in a different city told you.
What I'd actually do in your position
Decide whether short-term rental income is a requirement or a bonus. If it's a requirement, that constraint drives your search from day one and eliminates most of the map. Better to know that in week one than week nine.
Run the Bend-versus-Redmond comparison honestly. The $200,000 gap buys a lot of forgiveness for a slightly less charming main street.
Tour before you fly. There's no reason to spend a weekend and a plane ticket narrowing a list you could narrow on video.
Get permit answers in writing from the city, not the listing. Every time.
Ichi Halvorson, REALTOR® | Golden Gate Realty & Finance | DRE #01973163 ichihalvorson@goldengate365.com · goldengate365.com · @ichi.sf.realtor Born in Korea. Built in SF.
This article is educational and is not legal, tax, or investment advice. Short-term rental codes change; verify current requirements directly with the City of Bend, the City of Redmond, or Deschutes County before relying on any of it. Licensed in California, DRE #01973163. Oregon transactions are handled in partnership with a licensed Oregon broker.
