20180 Winston Loop

Bend, OR 97703

$2,950,000
Price
5
Beds
5,528 Sq. Ft.
$534 / Sq. Ft.
5,528
Sq. Ft.
$534
per Sq. Ft.
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a living room with furniture and a large window
a living room with furniture a fireplace and a large window
a living room with furniture
a living room with furniture and a large window
a living room with furniture and a large window
a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a sink a stove and a wooden cabinets
a kitchen with lots of counter top space and painting on the wall
a kitchen with stainless steel appliances granite countertop a sink and dishwasher next to a large window
a kitchen with stainless steel appliances granite countertop a sink and cabinets
a dining room with furniture floor to ceiling windows and a chandelier
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a bedroom with bed and window
a bedroom with a bed and wooden floor
a bedroom with furniture and a large window
a room with walk in closet and wooden floor
a spacious bathroom with a granite countertop sink and a large mirror
a bathroom with a sink and a bathtub
a spacious bathroom with a granite countertop sink mirror and shower
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First Floor Shared bath #2
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a bathroom with a sink a toilet and shower
2nd Floor Informal Living Space
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2nd Floor Guest Room
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Office Space above the RV Garage
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RV Garage that can host a 44' RV
Storage Areas in the Shop
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West views of the backyard
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Main Floor
Upper Floor
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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...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.
  1. Listed by Betsey Leever Little • Brokerage DRE #201249302 • Cascade Hasson SIR
    P: (541)-301-8140 C: (541)-301-8140 betsey.little@cascadesir.com

Property Details for 20180 Winston Loop

Architectural Style
Northwest, Traditional
Subdivision Name
Winston Ranch
View
Mountain(s), Panoramic, Territorial
Has View
Yes
Zoning Description
MUA10
LISTING UPDATED: 06/02/2026 11:57 AM

Property Details for 20180 Winston Loop

StatusActive
MLS #220222189
Days on Market11
Taxes$20,690 / year
HOA Fees$395 / month
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2000
Lot Size7.46 AC / 324,957 SF
CountyDeschutes County
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Location

Listing Courtesy of Cascade Hasson SIR
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Building Information for 20180 Winston Loop

Stories2Year Built2000Building Size-Lot Size7.46 AC / 324,957 SF

Payment Calculator

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$16,819 per month

30 year fixed, 6.36% Interest

Principal and Interest

$14,700

Property Taxes

$1,724

HOA Dues

$395

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Property Information for 20180 Winston Loop

Summary
Location and General Information
  • Cross Street: Tumalo Road
  • Latitude: 44.14951898
  • Longitude: -121.32038396
  • Senior Community: No
Taxes and HOA
  • Additional Parcels: No
  • Association Fee: $395.08
  • Association Fee Frequency: Monthly
  • Association: Yes
  • Derived Association Fee Monthly: $395.08
  • Parcel Number: 154885
  • Tax Annual Amount: $20,690.17
  • Tax Lot: 14
  • Tax Map Number: 1612320000505
  • Tax Year: 2025
School Information
  • Elementary School: North Star Elementary
  • High School: Mountain View Sr High
  • Middle Or Junior School: Sky View Middle
Parking
  • Attached Garage: Yes
  • Garage Spaces: 6.0
  • Garage: Yes
  • Parking Features: Asphalt, Attached, Detached, Driveway, Garage Door Opener, RV Access/Parking, RV Garage, Tandem, Workshop in Garage, Garage
Property
Lot Information
  • Lot Features: Landscaped, Level, Pasture, Sprinklers In Front, Sprinklers In Rear
  • Lot Size Acres: 7.46
  • Lot Size Area: 7.46
  • Lot Size Square Feet: 324957.6
  • Lot Size Units: Acres
  • Road Responsibility: Private Maintained Road
  • Road Surface Type: Paved
Property and Assessments
  • Building Area Total: 5528.0
  • Living Area: 5528.0
  • Living Area Source: Assessor
  • New Construction: No
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Year Built: 2000
Building Features
  • Common Walls: No Common Walls
  • Construction Materials: Stone, Frame
  • Levels: Two
  • Other Structures: RV/Boat Storage, Second Garage, Storage, Workshop
Farm Information
  • Horse: Yes
  • Irrigation Source: District
  • Irrigation Water Rights Acres: 6.4
  • Irrigation Water Rights: Yes
Utilities
  • Sewer: Septic Tank
  • Water Source: Private, Well
Interior and Exterior Features
Exterior Features
  • Association Amenities: Snow Removal
  • Exterior Features: Barbecue, Built-in Barbecue, RV Hookup
  • Patio And Porch Features: Covered
  • Pool Features: Heated, In Ground, Pool Cover
  • Roof: Tile
Interior Features
  • Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • Full Bathrooms: 4
  • Total Integer Bathrooms: 4
  • Total Bedrooms: 5
  • Cooling: Ceiling Fan(s), Central Air, Heat Pump, Zoned
  • Has Cooling: Yes
  • Fireplace Features: Great Room, Propane
  • Has Fireplace: Yes
  • Fire Sprinkler System: Yes
  • Flooring: Carpet, Hardwood, Stone
  • Heating: Electric, Forced Air, Heat Pump, Zoned
  • Has Heating: Yes
  • Interior Features: Bar, Breakfast Bar, Built-in Features, Ceiling Fan(s), Double Vanity, Dry Bar, Granite Counters, Kitchen Island, Open Floorplan, Pantry, Soaking Tub, Tile Counters, Walk-In Closet(s)
  • Security Features: Carbon Monoxide Detector(s), Fire Sprinkler System, Security System Owned, Smoke Detector(s)
  • Has Spa: No
  • Window Features: Double Pane Windows
Rental
Tenant Information
  • Occupant Type: Owner

Property History for 20180 Winston Loop

DateEvent & SourcePriceAppreciation
May 26, 2026

Listed (Active)

Oregon Data Share #220222189

$2,950,000—
Oct 6, 2025

Expired

Oregon Data Share #220206606

$2,700,000—
Jul 28, 2025

Listed (Active)

Oregon Data Share #220206606

$2,700,000—
DateEvent & SourcePrice
05/26/2026

Listed (Active)

Oregon Data Share #220222189

$2,950,000
10/06/2025

Expired

Oregon Data Share #220206606

$2,700,000
07/28/2025

Listed (Active)

Oregon Data Share #220206606

$2,700,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 20180 Winston Loop

Taxable ValueLand-Additions-Total-
Tax Record2025$20,690 ($1,724 / month)
Home Facts
Beds5Baths4Total Finished SqFt5,528 SqFtAbove Grade Finished SqFt5,528 SqFtStories2Lot Size324,958 SqFtStyleSingle Family ResidenceYear Built2000CountyDESCHUTESAPN161232 00 00505Fireplace TypePre Fab

Schools near 20180 Winston Loop

This home is within Bend-La Pine Schools.
Rating
School
Type
Grades
Distance
North Star Elementary
Public - K to 5
Sky View Middle School
Public - 6 to 8
Mountain View Senior High School
Public - 9 to 12
Three Rivers K-8 School
Public - K to 8
Rating
School
Distance
North Star Elementary
PublicK to 5

Sky View Middle School
Public6 to 8

Mountain View Senior High School
Public9 to 12

Three Rivers K-8 School
PublicK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 20180 Winston Loop, Bend, OR 97703

20180 Winston Loop is a single family home for sale in Bend, OR 97703. This property was listed for sale on May 27, 2026 by Cascade Hasson SIR, it's currently listed at $2,950,000. It has been on the market for a total of 11 days and was last sold on October 18, 2022. This listing's school district is Bend-La Pine Schools. Nearby schools include North Star Elementary, Sky View Middle School and Mountain View Senior High School. 20180 Winston Loop is a 5-bed, 4-bath, 5,528 sqft single family home built in 2000.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Cascade Hasson SIR

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