Get new listings emailed daily! JOIN SIGN IN
Denny Osborn, Broker
REALTOR®, ABR, e-PRO, RSPS
(541) 771-1578
Facebook Icon LinkedIn Icon Instagram Icon 
Denny's Blog

Subscribe and receive email notifications of new blog posts.




rss logo RSS Feed
October
20

One of the questions I hear from homeowners is, "Is now a good time to sell?"

It's a reasonable question. But after 20 years in Bend real estate, I've found that the better question is usually:

"Is now the right time for me to sell?"

Those are two very different questions.

Real estate markets change. Interest rates move. Inventory rises and falls. Buyer demand can look different from one season to the next. Trying to wait for the perfect combination of high prices, low rates, strong demand, and plenty of good replacement homes can leave homeowners waiting for conditions that may never line up perfectly.

Instead, I think the decision to sell should start with your life, your finances, and what you want to accomplish after the sale.

Start With Why You're Considering Selling

Most homeowners don't wake up one morning and randomly decide to put their house on the market. Usually something has changed.

Maybe the house feels too large now that the kids are gone. Maybe you're relocating for work or family. You may want to be closer to children or grandchildren. Perhaps you're tired of maintaining a large yard, acreage, or an older home.

Or maybe you're simply ready for something different.

Those reasons matter because selling a home isn't the goal by itself. The goal is what selling the home allows you to do next.

Before worrying about whether the Bend market is at its absolute peak, I would spend some time thinking about what you want your life to look like after the sale.

How Much Equity Do You Have?

For many Bend homeowners, equity can be an important part of the decision.

If you've owned your home for a number of years, the combination of appreciation and paying down your mortgage may have created substantial equity.

But don't base your plans on an online home-value estimate.

Before making a decision, you want a realistic idea of what your home could sell for in the current Bend market, what your approximate selling expenses would be, whether there are any mortgages or other liens to pay off, and roughly how much you could walk away with after closing.

That net number is much more useful than simply knowing your home's estimated value.

Once you understand your potential proceeds, you can start looking at what those dollars could accomplish.

What Will You Buy — or Do — Next?

This is one of the most important parts of the conversation, and it's sometimes overlooked.

You can get a great price for your Bend home and still make a poor overall move if you haven't thought through your replacement housing.

Where will you go?

Will you purchase another home in Bend? Move somewhere else in Central Oregon? Relocate out of state? Downsize? Rent for a while? Move closer to family?

If you're purchasing another home, we also need to look at what homes in your target market cost and what financing might look like.

Sometimes homeowners discover that selling makes a lot of sense. Other times, after looking at their next step, staying where they are for another year or two makes more sense.

Either answer is okay.

The purpose of doing the homework is to know before the For Sale sign goes up.

Has Your Home Become More Work Than You Want?

This can be a major factor, especially for longtime homeowners.

A larger home, big yard, acreage property, shop, landscaping, snow removal, irrigation systems, and ongoing repairs may have been exactly what you wanted 10 or 15 years ago.

That doesn't mean it still fits your life today.

I've talked with homeowners who could comfortably afford their homes but were simply tired of maintaining them.

There's a real cost to homeownership beyond the mortgage payment. There's also the time and energy involved.

If you're spending weekends maintaining a property you'd rather be enjoying, it may be worth asking whether the home still fits the way you want to live.

Downsizing Doesn't Always Mean Going Small

When people hear "downsizing," they often picture moving into a tiny house or condo.

That's not necessarily what it means.

For some Bend homeowners, downsizing simply means moving from a two-story home to a single-level property. It could mean less yard maintenance, fewer unused bedrooms, a newer home with fewer repairs, or moving closer to shopping, trails, medical services, family, or other things you use regularly.

The goal isn't necessarily to own less.

It's to own a home that works better for your next stage of life.

Consider Your Financial Goals

Selling can also be part of a larger financial plan.

Maybe you'd like to reduce or eliminate a mortgage before retirement. You might want to free up equity for investments, travel, or other goals. Or you may want to reduce property taxes, insurance, utilities, and maintenance expenses.

This is where it helps to look beyond the sales price.

Suppose you sell your current home for a strong price but use nearly all of the proceeds to purchase another expensive home. Your financial position may not change very much.

On the other hand, selling and purchasing a less expensive property could free up equity and lower your monthly expenses.

The right answer depends on what you're trying to accomplish.

For significant tax, investment, or retirement decisions, I also recommend talking with the appropriate tax or financial professional before making the move.

Don't Ignore the Cost of Waiting

There's plenty of discussion about whether homeowners should wait for prices to rise or mortgage rates to fall.

But waiting has costs too.

Your home may need a roof, HVAC system, exterior paint, landscaping, or other major maintenance in the next few years. Your property taxes, insurance, utilities, and upkeep continue while you own the home.

And sometimes the biggest cost isn't financial.

If you'd rather be living closer to family, traveling more, spending less time maintaining a property, or beginning the next chapter of your life, waiting several years to perfectly time the market may not actually improve your situation.

That's something only you can decide.

The Bend Market Still Matters — Just Not in Isolation

None of this means market conditions should be ignored.

Before selling a house in Bend, I want homeowners to understand what's happening with comparable sales, active competition, buyer demand, days on market, price reductions, and inventory in their specific part of town and price range.

Those conditions help us determine a realistic pricing and marketing strategy.

But I wouldn't let a headline about the Bend Oregon real estate market make the decision for you.

Your neighborhood and price range may behave differently from Bend as a whole. More importantly, your reasons for moving may matter much more than a small change in the median sales price.

Ask Yourself These Questions

If you're wondering when to sell a home in Bend, Oregon, start here:

  • Why am I thinking about selling?

  • What would I like to change about my current living situation?

  • Approximately how much equity do I have?

  • Where would I go after the sale?

  • What would my replacement home cost?

  • Would moving improve my monthly financial picture?

  • Is maintaining my current home becoming a burden?

  • If I don't sell now, what am I waiting for?

  • What would have to happen for me to feel comfortable making the move?

  • If I wait another two years, will I be glad I did?

You don't need perfect answers to every question. But thinking through them can make the decision much clearer.

The Right Time Isn't Always the Top of the Market

I've been through enough real estate cycles in Bend to know how difficult it is to identify the "perfect" time to sell until after that moment has already passed.

That's why I don't think most homeowners should build their plans around predicting the market.

Instead, look at the entire move.

What is your home realistically worth today? How much equity would you have available? Where would you go next? What would that cost? And would making the move put you in a better position personally, financially, or both?

If the answers line up, it may be the right time to sell — even if the market isn't perfect.

And if they don't, staying put may be the better decision.

Thinking About Selling Your Bend Home?

If you're considering a move but aren't sure whether the numbers or timing make sense, I'm happy to help you work through it.

We can look at your home's current market value, your likely selling costs, what's happening in your part of Bend, and what your options might look like after the sale.

No pressure and no need to make a decision before you're ready. Just good information so you can decide what makes the most sense for you.

Denny Osborn, ABR, e-PRO, RSPS
Bend Premier Real Estate
Bend Real Estate Market Clarity Specialist

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/20/2026. The listing information on this page last changed on 10/20/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 10/20/2026 12:18:20 AM EST) or RMLS (last updated Tue 10/20/2026 12:16:26 AM EST) or COAR/MLSCO (last updated Tue 10/20/2026 12:11:18 AM EST). Real estate listings held by brokerage firms other than Bend Premier Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder