855.375.4001
Listing Courtesy of: Betsey Little - Cascade Hasson SIR 541-383-7600
$2,850,000 affordable loan icon Calculate Payment

20180 Winston Loop Bend, OR 97703

Down payment assistance icon
Single Family Residence
5 Beds
4 Baths
... Bed/Bath
5,528 Sq. Ft.

Property Activity

Time on Site
days
Days on Market
Views
Saves
Last updated on 10/1/2026 11:00 AM
Set above downtown Tumalo on just over 7 acres, this legacy estate in Winston Ranch is the kind of property that rarely comes available. Mornings open to 180-degree Cascade Mountain views, afternoons unfold by the pool, and evenings settle into a private movie theater or the one-of-a-kind office and... den wrapped in spectacular woodwork. Freshly updated throughout with new interior and exterior paint, hardwood flooring, new carpet, updated fixtures, and a reworked primary ensuite, the home feels both timeless and ready. The ground-level primary suite frames an incredible mountain view with a large walk-in closet, picture-perfect tub, and dual vanities, while cherry cabinetry and an open-concept kitchen and living space anchor everyday life. A finished shop with bathroom and workspace and a 44' RV bay deliver rare flexibility. HOA-managed underground irrigation, a 1-mile private loop, and an underground dog fence make country living effortless. Call for a private tour. Continue reading
MLS#
220222189
Property Type
Single Family
Bedrooms
5
Bathrooms
4 Full
Year Built
2000
HOA Fee
$395
Square Feet
5,528 sq. ft
Lot Size
7.46
Stories
2.0
Sewer
Holding Tank

Receive an email as soon as the price changes

Receive an email

as soon as the price changes
Get Price Alerts
price alerts icon

Get Price Alerts

Don't miss your chance. Receive an email as soon as the price changes.

Notify Me

Get email alerts when
a home price changes

Sign up
view of kitchen

Walk Score measures the walkability of any address, Transit Score measures access to public transit on a scale of 1-100.

Source: Walk Score®
scales icon

How much home can I afford?

Kickstart your home search journey with our online Pre-Approval.

Get Started
megaphone icon

See How Much You Could Save

Thinking about buying or selling? Talk to one of our Mortgage Professionals today to see how much you could save on your next home. Call us at 833-685-2565.

Let's Talk
Listing Courtesy of: Betsey Little - Cascade Hasson SIR 541-383-7600
Andrea D. Conner, License 201225347, Xome Inc., License 201213296, [email protected], 844-400-XOME (9663), 725 S. Main Street, Milton-Freewater, OR 97862

The content relating to real estate for sale on this website comes in part from the MLS of Central Oregon. Real estate listings held by Brokerages other than Xome Inc. are marked with the Reciprocity/IDX logo, and detailed information about these properties includes the name of the listing Brokerage. © MLS of Central Oregon (MLSCO).
This content last refreshed on 10/1/2026 11:00 AM. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Information is deemed reliable but is not guaranteed.
save icon Save
save icon Save
share icon Share
checkmark icon Get Pre-Approved