20180 Winston Loop, Bend, OR 97703
Local realty services provided by:CENTURY 21 North Homes Realty
Listed by: betsey leever little
Office: cascade hasson sir
MLS#:220222189
Source:OR_SOMLS
Price summary
- Price:$2,850,000
- Price per sq. ft.:$515.56
- Monthly HOA dues:$395
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.
Contact an agent
Home facts
- Year built:2000
- Listing ID #:220222189
- Added:59 day(s) ago
- Updated:July 26, 2026 at 03:04 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:4
- Full bathrooms:4
- Flooring:Carpet, Hardwood, Stone
- Bathrooms Description:Double Vanity, Enclosed Toilet(s), Soaking Tub, Tile Shower
- Kitchen Description:Dishwasher, Microwave, Oven, Range, Refrigerator
- Bedroom Description:Primary Downstairs
- Living area:5,528 sq. ft.
Heating and cooling
- Cooling:Central Air, Heat Pump, Zoned
- Heating:Electric, Forced Air, Heat Pump, Zoned
- Central air:Yes
Structure and exterior
- Roof:Tile
- Year built:2000
- Building area:5,528 sq. ft.
- Lot area:7.46 Acres
- Lot Features:Landscaped, Level, Pasture, Sprinkler Timer(s), Sprinklers In Front, Sprinklers In Rear
- Architectural Style:Northwest, Traditional
- Construction Materials:Frame
- Exterior Features:RV Dump, RV Hookup
- Foundation Description:Stemwall
- Levels:2 Story
Schools
- High school:Mountain View Sr High
- Middle school:Sky View Middle
- Elementary school:North Star Elementary
Utilities
- Water:Well
- Sewer:Septic Tank, Standard Leach Field
Finances and disclosures
- Price:$2,850,000
- Price per sq. ft.:$515.56
- Tax amount:$20,690 (2025)
Features and amenities
- Appliances:Dishwasher, Microwave, Oven, Range, Refrigerator, Washer
Parking
- Parking description:Asphalt, Attached, Detached, Driveway, Garage Door Opener, RV Access/Parking, RV Garage, Tandem
- Garage:Yes
- Garage spaces:6
New listings near 20180 Winston Loop
- New
$3,000Active1 beds 1 baths662 sq. ft.18575 SW Century Drive # 1221 B, Bend, OR 97702
MLS# 220225983Listed by: PATTY MCMEEN REAL ESTATE - New
$825,000Active3 beds 2 baths1,876 sq. ft.3271 NW Melville Drive, Bend, OR 97703
MLS# 220225984Listed by: STELLAR REALTY NORTHWEST - New
$160,000Active3 beds 2 baths1,970 sq. ft.1001 SE 15th Street #12, Bend, OR 97702
MLS# 220225657Listed by: JOHN L SCOTT BEND - New
$629,900Active3 beds 3 baths1,939 sq. ft.3879 NE Petrosa Avenue, Bend, OR 97701
MLS# 220225980Listed by: PAHLISCH REAL ESTATE, INC. - New
$940,000Active3 beds 3 baths2,099 sq. ft.17672 Bittern Lane #8, Bend, OR 97707
MLS# 220225978Listed by: CASCADE HASSON SIR - New
$900,000Active2 beds 3 baths1,774 sq. ft.2641 NW Crossing Drive, Bend, OR 97703
MLS# 220225972Listed by: WINDERMERE REALTY TRUST - New
$950,000Active3 beds 3 baths1,896 sq. ft.1374 NW Fort Clatsop Street, Bend, OR 97703
MLS# 220225973Listed by: REALTY ONE GROUP DISCOVERY - New
$3,300,000Active6 beds 7 baths7,320 sq. ft.62354 Erickson Road, Bend, OR 97701
MLS# 220225889Listed by: NW BEND HOMES, LLC - Open Sun, 10am to 1pmNew
$900,000Active4 beds 3 baths2,899 sq. ft.2048 NE Cradle Mountain Way, Bend, OR 97701
MLS# 220225954Listed by: WORKS REAL ESTATE - Open Sun, 1 to 3pmNew
$699,000Active4 beds 2 baths1,996 sq. ft.61370 SE Preston Street, Bend, OR 97702
MLS# 220225957Listed by: STELLAR REALTY NORTHWEST