Three towns within forty minutes of each other and three different places to live. What you are choosing, what each town gives up, and the live market page for each.
Most people who move to Central Oregon start by searching Bend. A lot of them end up in Redmond or Sisters, and most of those are happy about it. The three towns sit within forty minutes of each other and share the same mountains, but they are different places to live. This is the decision page.
What you are really choosing
You are choosing between three things: how much house your money buys, how close you are to the things that made you look at Central Oregon, and how much town you want around you. Bend has the most of everything and costs the most. Redmond has the airport, a working downtown, and more house per dollar. Sisters is small, walkable, and quiet, with the Cascades right there. The live prices for each are on the market pages linked in each section.
Bend
Bend is the largest city in the region and the center of it. It has the hospital, the university branch, the breweries, the Old Mill District, and the trail network along the Deschutes. Mt. Bachelor is about 21 miles west of downtown by road. Housing runs from mill-era cottages on the west side to new subdivisions on the east and southeast, and the price gap between those two sides is real. Bend is where you buy if you want to walk or bike to things, if your work is here, or if you want the widest choice of homes. It is also where you pay the most for the same square footage. Bend homes and districts. Bend market page. Moving to Bend guide.
Redmond
Redmond is about 17 miles north of downtown Bend on Highway 97. It has the regional airport, the fairgrounds, a downtown that has filled in over the last decade, and most of the region's newer entry-level subdivisions. The same money buys more house and more lot in Redmond than in Bend, and the drive to downtown Bend is about 25 minutes without traffic. Smith Rock and the Crooked River are closer from Redmond than from Bend. Redmond is where you buy if you want a newer home, a real yard, and a Bend commute you can live with. Redmond homes. Redmond market page. Moving to Redmond guide.
Sisters
Sisters is about 22 miles northwest of downtown Bend at the base of the Three Sisters. It is a small town with a western-themed main street, a rodeo, a folk festival, and a quilt show that fills the town every July. Housing is a mix of in-town lots, acreage on the edges, and Black Butte Ranch a few miles west. Inventory is thin because the town is small, so buyers often wait for the right house rather than choosing among many. Sisters is where you buy if you want quiet, a walkable center, and mountain access, and you do not need to be in Bend every day. Sisters homes. Sisters market page. Moving to Sisters guide.
Quick comparison
- Most choice of homes and the most to do: Bend.
- Most house for the money with a short commute: Redmond.
- Smallest and quietest, closest to the mountains: Sisters.
- Airport: Redmond. Hospital: Bend. Ski hill: closest from Bend.
- Inventory: deepest in Bend, growing in Redmond, thin in Sisters.
Questions
Is Redmond cheaper than Bend?
Is Sisters a cheaper alternative to Bend?
Not reliably. Sisters has a small housing stock and a lot of acreage and custom homes, so its median can sit near or above Bend's depending on what closed that month. Buyers choose Sisters for the town and the setting, not for a discount. Check the Sisters market page for the current number.
How long is the commute between these towns?
Downtown Bend to downtown Redmond is about 17 miles on Highway 97, about 25 minutes without traffic. Bend to Sisters is about 22 miles on Highway 20, about 35 minutes. Both run longer on summer weekends and on snow days.
Which town is better for remote workers?
All three have fiber or cable service in town, and rural parcels need to be checked address by address. Bend has the most coworking space and coffee shops. Redmond has the airport if you fly for work. Sisters has the least noise. We check the provider at the specific address before you offer.
Should I rent first before choosing a town?
If you have never spent a winter here, renting for a few months is a reasonable way to test the drive, the snow, and the town before you buy. If you have visited in more than one season and know your commute, buying directly is common. Either way, set up listing alerts so you see the market move while you decide.
Next step
Open the three market pages side by side, then set an alert for the towns you have not ruled out. When you are ready to tour, book a call and we will plan a day that covers all three.
Matt RyanOwner & Principal Broker at Ryan Realty.
