A buyer watching Redmond's numbers this year sees a headline that looks like an opening: the median sale price is down 10.1% year over year, sitting at $470,000 over the three months ending in May 2026. That reads like room to negotiate. So the buyer waits, then comes in a little under asking on a well-priced three-bedroom near Redmond's core, expecting the seller to be grateful for any offer at all.
The house is already pending. It took 26 days, and it went for close to what was asked.
That contradiction, a falling median and a market still absorbing homes fast, is the thing worth understanding before you compare Redmond, Sisters, and Bend on price alone. The three towns are not experiencing the same slowdown. They're experiencing three different shifts in what's actually selling, and the region-wide "prices are down" story hides that.
The median is dropping because the mix is changing, not because homes are worth less
A May 2026 review of the Redmond market in the Bend Source found that homes priced above $750,000 were averaging 76 days on market this year, a real improvement from 110 days at the same point in 2025. Days on market overall in Redmond hit their lowest level since 2022. At the same time, the report noted a shift toward more lower-priced sales, which pushed price per square foot higher even as the overall median sale price trended downward.
That's the mechanism. When more mid-range and entry-level homes close relative to expensive ones, the median falls even if no individual home is selling for less than a comparable one would have a year ago. Redfin's own price-per-square-foot figure for Redmond backs this up only partially: it's down 1.5% year over year, essentially flat, while the headline median is down 10.1%. A flat price-per-square-foot next to a double-digit median drop is the signature of a market where the mix of what's selling changed, not one where values collapsed.
The same report found Redmond has "largely been insulated" from the below-asking-price selling that hit other parts of Central Oregon over the past two years, though it flagged the first small declines in percentage of original list price received as some sellers discover their homes aren't worth quite what they'd hoped.
| Market | Median sale price | Change vs. year prior | Days on market | Price per sq. ft. |
|---|---|---|---|---|
| Redmond (3 mo. ending May 2026) | $470,000 | down 10.1% | 26 days | $304, down 1.5% |
| Sisters (3 mo. ending May 2026) | $647,000 | down 10.4% | 45 days | $397, up 6.1% |
Both towns show a falling median. Only one shows a falling price per square foot. Sisters' rose 6.1% in the same window its median fell double digits, which is the more extreme version of the same story: the composition of what's selling is doing more work than the market itself.
What's actually happening in Redmond
By the end of August 2026, Resideline was tracking 34 active listings against 51 pending sales in Redmond's 97756 ZIP code, a pending-to-active ratio of 1.50. That ratio points toward a seller's market: buyers are absorbing available inventory faster than sellers are replacing it. The median closed sale over the trailing six months sat at $475,000, with the middle half of all sales landing between $410,000 and $624,000, a wide enough band that a single median tells a buyer very little about what a specific house in a specific price tier will actually cost.
Zoom out to the prior season and the tone was more measured. The Redmond Spokesman, citing the Redmond-based Beacon Report from November 2025, described a market where homes were taking 38 days to sell against an inventory of about a month and a half. One analyst called it "normal market conditions for Central Oregon's seasonal market," adding that a 50 to 60 day window is typical and that the region was simply settling back to its pre-pandemic rhythm.
Read against the summer 2026 numbers, that's a market that tightened again with the season, not one settling into a permanent buyer's advantage. For anyone reading Redmond's falling median as room to negotiate, the pending-to-active ratio is a helpful second number to check, since it shows how quickly homes are actually being claimed.
Sisters is two markets wearing one median
Sisters presents the sharpest version of this problem. The Nugget Newspaper's April 2026 look at the local market found 53 home sales in the first quarter totaling $45.9 million, up more than 10% from the 43 sales and $40.7 million recorded in the same quarter of 2024. Mortgage rates had eased slightly, from an average of 6.7% in 2025 to 6.41% in the first quarter of 2026, which the paper credited with drawing some buyers back in.
The more telling detail in that reporting is the gap between average and median. Going back to the first quarter of 2024 for comparison, the average sale price in Sisters was $946,902, while the median, described in the piece as the more accurate reflection of the actual market, was $750,000. A quarter of that gap comes from genuine luxury activity: cash purchases at the top end pull the average up without moving the median much, which is exactly why a citywide median in Sisters undersells what a buyer competing for a typical listing will actually face.
The Nugget also flagged something with longer legs than any single quarter's price: a five-year high in lots sold during the first quarter of 2026, which the paper read as an early signal of a coming construction boom. Some of that new supply is already visible in developments like Sisters Woodlands, built to Earth Advantage Platinum standards with fire-resistant exteriors and metal roofing, the kind of construction that's becoming less optional than practical given the town's wildfire exposure. Sisters has also adopted a 500-foot separation rule for short-term rentals, mirroring Bend's approach, which keeps residential blocks from converting into rental clusters.
For a buyer comparing Sisters to Redmond, the lesson isn't that one town is more expensive than the other. It's that Sisters' median is a weaker guide to what you'll actually pay, because the town's sales are split between a starter tier and a cash-heavy luxury tier in a way Redmond's more evenly distributed market isn't.
Bend still sets the ceiling
Bend doesn't have a directly comparable same-window figure to Redmond and Sisters in the data reviewed here, but regional forecasts published toward the end of 2025 pegged it as the region's priciest market, with a median near $775,000, competitive and premium-priced relative to its neighbors. That tracks with what both the Redmond and Sisters reporting describe: Bend as the anchor buyers measure against, Redmond as the value entry point roughly 20 to 30% below it, and Sisters as the smaller, more volatile market in between, prone to swinging with a handful of high-dollar closings in any given quarter.
What this means if you're comparing the three towns
- A falling median in Redmond or Sisters is not the same signal as falling prices. Check price per square foot before assuming there's room to negotiate.
- Redmond's pending-to-active ratio matters more than its year-over-year median change if you're trying to gauge how fast you'll need to move on a listing.
- Sisters' median price is the least reliable of the three for budgeting purposes. Look at the spread between recent sales, not just the midpoint, and factor in that a meaningful share of transactions close in cash.
- The lot sales reported in Sisters during the first quarter of 2026 are worth tracking if you're patient. New construction on that scale takes time to reach the market, but it's the clearest early signal of where inventory loosens first.
- None of these towns behaved the same way over the past year. Treating "Central Oregon" as a single market, the way a portal-level search often does, will cost you the specifics that actually decide whether you're negotiating from strength or guessing.
A couple of questions worth asking directly
If Redmond's median is down 10%, why aren't sellers negotiating? Because the drop is largely coming from a shift toward more lower-priced homes closing, not from existing homes losing value. Price per square foot in Redmond is nearly flat, and the pending-to-active ratio through August 2026 still favored sellers.
Is Sisters actually a buyer's market right now? The citywide median suggests softening, but the town's sales split between a starter tier and a cash-heavy luxury tier, which pulls the median down without necessarily making the mid-market home you want any easier to win.
If you're weighing Redmond against Sisters against Bend and want someone to walk through what a specific price point actually buys in each, not just what the median implies, Worthland Real Estate can pull the comparison together and help you price your search around the town that actually fits your budget and timeline.
