Listed by: Betsey Leever Little · Cascade Hasson SIR
- 5 beds
- 4 baths
- 5,528 sqft
20180 Winston Loop, Bend, OR 97703
- Single Family ResidenceHome type
- Built in 2000Year built
- 7.46 acresLot
- $516/sqftPrice per sqft
- $395/moHOA
- 6-car garageParking
About this home
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.
Facts & features
Interior
- Bedrooms
- 5
- Bathrooms
- 4
- Full bathrooms
- 4
- Living area
- 5,528 sqft
- Levels
- Two
Features
- Breakfast Bar
- Built-in Features
- Ceiling Fan(s)
- Double Vanity
- Dry Bar
- Enclosed Toilet(s)
- Granite Counters
- Kitchen Island
- Linen Closet
- Open Floorplan
- Pantry
- Primary Downstairs
- Soaking Tub
- Tile Counters
- Tile Shower
- Walk-In Closet(s)
Appliances
- Dishwasher
- Dryer
- Microwave
- Oven
- Range
- Refrigerator
- Washer
Heating & cooling
- Electric
- Forced Air
- Heat Pump
- Zoned
- Central Air
- Heat Pump
- Zoned
Flooring
- Carpet
- Hardwood
- Stone
Property
- Lot size
- 7.46 acres
- Garage spaces
- 6
- Subdivision
- Winston Ranch
Exterior features
- Built-in Barbecue
- RV Dump
- RV Hookup
View
- Cascade Mountains
- Panoramic
- Territorial
Parking
- Asphalt
- Attached
- Detached
- Driveway
- Garage Door Opener
- RV Access/Parking
- RV Garage
- Tandem
- Workshop in Garage
Construction
- Home type
- Single Family Residence
- Property type
- Residential
- Year built
- 2000
Materials
- Frame
- Tile roof
Utilities
Sewer & water
- Septic Tank
- Standard Leach Field
- Well water
Community & HOA
- Subdivision
- Winston Ranch
- HOA dues
- $395 monthly
- County
- Deschutes
Financial & listing details
- List price
- $2,850,000
- Original list price
- $2,950,000
- Price per sqft
- $516
- Annual property tax
- $20,690
- Date on market
- May 27, 2026
- Days on market
- 128
- MLS#
- 220222189
Price & status history
| Date | Event | Price |
|---|---|---|
| May 27, 2026 | Listed for sale | $2,950,000 |
Neighborhood
- SubdivisionWinston Ranch
- CityBend, OR 97703
- CountyDeschutes
Payment calculator
Estimated monthly payment
$17,124/mo
- Principal & interest$14,411
- Property taxes$1,724
- Homeowners insurance$594
- HOA dues$395
Loan amount $2,280,000 · 30-year fixed at 6.5%
An estimate for planning, not a loan offer. The 6.5% rate is an example; ask a lender for today’s rate. Taxes use the listing’s annual tax amount. Insurance is estimated; mortgage insurance is not included.
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Listing provided by Cascade Hasson SIR · Listing agent: Betsey Leever Little
- Source
- MLS of Central Oregon
- MLS#
- 220222189
- Last updated
- Aug 29, 2026 at 11:34 PM
Listing information is deemed reliable but not guaranteed and should be independently verified. Listings shown are for demonstration while our MLS of Central Oregon IDX feed is being set up.