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20180 Winston Loop

Bend, OR 97703
  • $2,950,000
  • STATUS: Active
  • ON SITE: 9 Days
  • MLS #: 220222189
UPDATED: 42 min ago
$2,950,000
  • 5
    BEDS
  • 7.46
    ACRES
  • 4
    BATHS
  • 0
    1/2 BATHS
  • 5,528
    SQFT
  • $534
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2000
County:
Area:

School Information

Elementary School:
Middle School:
High School:
Listing provided courtesy of Cascade Hasson SIR :.

Description

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.

Monthly Payment Calculator

Central Oregon Association of Realtors logo © 2026 Oregon Datashare (KCAR | MLSCO | SOMLS). All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Oregon Datashare. Real estate listings held by IDX Brokerage firms other than High Desert Realty are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. The consumer will not copy, retransmit nor redistribute any of the content from this website. Information provided is deemed reliable, but not guaranteed. Listing courtesy of High Desert Realty. Data last updated: .2026-06-06T11:43:50.743
www.bendoregonrealestate.com/homes/176902282
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20180 Winston Loop Bend, OR 97703

  • Price: $2,950,000
  • Status: Active
  • On Site: 9 Days
  • Updated: 42 min ago
  • MLS #: 220222189
5
Beds
4
Baths
0
½ Baths
7.46
Acres
5,528
SQFT
$534
$/SQFT
2000
Built
Neighborhood:
Winston Ranch
County:
Deschutes
Area:
Bend
Elementary School:
North Star Elementary
Middle School:
Sky View Middle
High School:
Mountain View Sr High
Property Description
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.
Exterior Features

Architectural Style NorthwestTraditional Attached Garage YN Yes Body Type [] Construction Materials Frame Exterior Features Built-in BarbecueRV DumpRV Hookup Foundation Details Stemwall Garage YN Yes Lot Features LandscapedLevelPastureSprinkler Timer(s)Sprinklers In FrontSprinklers In Rear Parking Features AsphaltAttachedDetachedDrivewayGarage Door OpenerRV Access/ParkingRV GarageTandemWorkshop in Garage Roof Tile Window Features Double Pane Windows

Interior Features

Appliances DishwasherDryerMicrowaveOvenRangeRefrigeratorWasher Basement [] Bonus Room Yes Cooling Central AirHeat PumpZoned Cooling YN Yes Dining Room Yes Eating Area Yes Fireplace Features Great RoomOfficePropane Fireplace YN Yes Flooring CarpetHardwoodStone Great Room Yes Heating ElectricForced AirHeat PumpZoned Heating YN Yes Interior Features Breakfast BarBuilt-in FeaturesCeiling Fan(s)Double VanityDry BarEnclosed Toilet(s)Granite CountersKitchen IslandLinen ClosetOpen FloorplanPantryPrimary DownstairsSoaking TubTile CountersTile ShowerWalk-In Closet(s) Kitchen Yes Laundry Yes Levels Two Living Room Yes Media Room Yes Office Yes Primary Bedroom Yes

Property Features

Accessibility Features [] Accessory Dwelling Unit YN No Additional Parcels YN No Association Amenities Snow Removal Association Fee 395.08 Association Fee Frequency Monthly Association YN Yes Building Area Total 5528 CCRs YN Yes Common Walls No Common Walls Community Features [] Horse YN Yes Irrigation Source District Irrigation Water Rights YN Yes Listing Terms CashConventional New Construction YN No Other Structures RV/Boat StorageSecond GarageStorageWorkshop Property Sub Type Single Family Residence Rented YN No Road Frontage Type Private Access Road Surface Type Paved Security Features Carbon Monoxide Detector(s)Fire Sprinkler SystemSecurity System OwnedSmoke Detector(s) Senior Community YN No Sewer Septic TankStandard Leach Field Short Term Rental Permit YN No Special Listing Conditions Standard Tax Annual Amount 20690.17 Tax Year 2025 View Cascade MountainsPanoramicTerritorial Water Source Well Waterfront Features [] Zoning Description MUA10

Listing information © 2026 MLS of Central Oregon
Listing provided courtesy of Cascade Hasson SIR :.

Central Oregon Association of Realtors logo © 2026 Oregon Datashare (KCAR | MLSCO | SOMLS). All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Oregon Datashare. Real estate listings held by IDX Brokerage firms other than High Desert Realty are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. The consumer will not copy, retransmit nor redistribute any of the content from this website. Information provided is deemed reliable, but not guaranteed. Listing courtesy of High Desert Realty. Data last updated: .2026-06-06T11:43:50.743
 
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High Desert Realty
101 NE Greenwood Ave Suite 100
Bend OR, 97701
Listing provided courtesy of Cascade Hasson SIR :.