After working with homeowners in Bend for over 20 years, I've noticed something consistent:
Most people don't wake up one day and decide to downsize.
It usually builds over time.
At first, it's just a thought in the back of your mind.
Then it turns into a conversation.
Eventually, it becomes a decision.
The challenge is knowing when that moment actually makes sense—financially and practically.
Here are a few of the signs I see that tell me it might be time.
This is usually the first shift.
After more than 20 years working in Bend real estate, one thing has become very clear:
The market changes constantly — but the fundamentals don't.
Every cycle brings new headlines, new predictions, and new emotions. Some years the market moves fast and competitive. Other times it slows down and buyers regain leverage.
But the biggest lessons usually stay the same.
Here are a few things two decades in Bend real estate has taught me.
If you spend enough time in real estate, you realize the market is never static.
I've watched Bend go through periods where homes sold within hours, a...