$2,850,000
$100K PRICE DROP

20180 Winston Loop Bend, OR 97703

Tumalo Area

Estimated payment $17,844/month

Total Views 9,826
5 Beds
4 Baths
5,528 Sq Ft
$516 Price per Sq Ft

Highlights

  • Horses Allowed On Property
  • Heated In Ground Pool
  • Second Garage
  • Media Room
  • RV Garage
  • Panoramic View

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.

Listing Agent

Betsey Leever Little

Cascade Hasson SIR License #201208569 Listed on: 05/27/2026

Cascade Hasson SIR

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $20,690

Year Built

  • Built in 2000

Lot Details

  • 7.46 Acre Lot
  • Landscaped
  • Level Lot
  • Front and Back Yard Sprinklers
  • Sprinklers on Timer
  • Zoning described as MUA10

HOA Fees

  • $395 Monthly HOA Fees

Parking

  • 6 Car Garage
  • Second Garage
  • Workshop in Garage
  • Tandem Parking
  • Garage Door Opener
  • Driveway
  • RV Garage

Property Views

  • Panoramic
  • Mountain
  • Territorial

Home Design

  • Northwest Architecture
  • Traditional Architecture
  • Stem Wall Foundation
  • Frame Construction
  • Tile Roof

Interior Spaces

  • 5,528 Sq Ft Home
  • 2-Story Property
  • Open Floorplan
  • Built-In Features
  • Dry Bar
  • Ceiling Fan
  • Propane Fireplace
  • Double Pane Windows
  • Great Room with Fireplace
  • Living Room
  • Dining Room
  • Media Room
  • Home Office
  • Bonus Room

Kitchen

  • Breakfast Bar
  • Oven
  • Range
  • Microwave
  • Dishwasher
  • Kitchen Island
  • Granite Countertops
  • Tile Countertops

Flooring

  • Wood
  • Carpet
  • Stone

Bedrooms and Bathrooms

  • 5 Bedrooms
  • Linen Closet
  • Walk-In Closet
  • 4 Full Bathrooms
  • Double Vanity
  • Soaking Tub
  • Bathtub Includes Tile Surround

Laundry

  • Laundry Room
  • Dryer
  • Washer

Home Security

  • Security System Owned
  • Carbon Monoxide Detectors
  • Fire and Smoke Detector
  • Fire Sprinkler System

Pool

  • Heated In Ground Pool
  • Pool Cover

Outdoor Features

  • Covered Patio or Porch
  • Separate Outdoor Workshop
  • Outdoor Storage
  • Built-In Barbecue

Schools

  • North Star Elementary School
  • Sky View Middle School
  • Mountain View Sr High School

Farming

  • 6 Irrigated Acres
  • Pasture

Utilities

  • Forced Air Zoned Heating and Cooling System
  • Heat Pump System
  • Irrigation Water Rights
  • Well
  • Septic Tank
  • Leach Field

Additional Features

  • Easements include irrigation
  • Horses Allowed On Property

Listing and Financial Details

  • Tax Lot 14
  • Assessor Parcel Number 154885

Community Details

Overview

  • Winston Ranch Subdivision

Recreation

  • Snow Removal

Home Details

Home Type

Single Family

Est. Annual Taxes

$20,690

Year Built

Built in 2000

Lot Details

7.46 Acres

HOA Fees

$395 per month

Parking

6

Listing Details

  • Architectural Style: Northwest, Traditional
  • Garage Yn: Yes
  • Unit Levels: Two
  • Lot Size Acres: 7.46
  • Prop. Type: Residential
  • New Construction: No
  • Property Sub Type: Single Family Residence
  • Road Frontage Type: Private Access
  • Road Surface Type: Paved
  • Subdivision Name: Winston Ranch
  • Year Built: 2000
  • Co List Office Phone: 541-383-7600
  • MLS Status: Active
  • General Property Information Audio Surveillance on Premises YN: Yes
  • General Property Information Accessory Dwelling Unit YN: No
  • Patio and Porch Features:Patio and Porch Features: Covered
  • Power Production:Power Production: None
  • Easements:Easements: Irrigation
  • Rooms:Rooms: Bonus Room, Dining Room, Great Room, Laundry, Media Room, Living Room, Kitchen, Office, Primary Bedroom, Eating Area
  • Special Features: VirtualTour

Interior Features

  • Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • Full Bathrooms: 4
  • Total Bedrooms: 5
  • Fireplace Features: Great Room, Propane, Office
  • Flooring: Carpet, Hardwood, Stone
  • Interior Amenities: 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), Enclosed Toilet(s), Linen Closet, Tile Shower
  • Window Features: Double Pane Windows
  • Fireplace: Yes

Exterior Features

  • Common Walls: No Common Walls
  • Construction Type: Frame
  • Exterior Features: Built-in Barbecue, RV Hookup, RV Dump
  • Foundation Details: Stemwall
  • Lot Features: Landscaped, Level, Pasture, Sprinklers In Front, Sprinklers In Rear, Sprinkler Timer(s)
  • Other Structures: RV/Boat Storage, Second Garage, Storage, Workshop
  • Roof: Tile
  • View: Panoramic, Territorial, Cascade Mountains
  • Horse: Yes
  • Pool Features: Heated, In Ground, Pool Cover
  • Patio And Porch Features: Covered

Garage/Parking

  • Garage Spaces: 6.0
  • Parking Features: Asphalt, Attached, Detached, Driveway, Garage Door Opener, RV Access/Parking, RV Garage, Tandem, Workshop in Garage
  • Attached Garage: Yes

Utilities

  • Cooling: Central Air, Heat Pump, Zoned
  • Heating: Electric, Forced Air, Heat Pump, Zoned
  • Security: Carbon Monoxide Detector(s), Fire Sprinkler System, Security System Owned, Smoke Detector(s)
  • Sewer: Septic Tank, Standard Leach Field
  • Water Source: Well
  • Cooling Y N: Yes
  • HeatingYN: Yes

Condo/Co-op/Association

  • Amenities: Snow Removal
  • Association Fee: 395.08
  • Association Fee Frequency: Monthly
  • Association: Yes
  • Senior Community: No

Schools

  • Elementary School: North Star Elementary
  • High School: Mountain View Sr High
  • Middle Or Junior School: Sky View Middle

Lot Info

  • Additional Parcels: No
  • Lot Size Sq Ft: 324957.6
  • Parcel #: 154885
  • Irrigation Water Rights Acres: 6.4
  • Irrigation Water Rights: Yes
  • ResoLotSizeUnits: Acres
  • Zoning Description: MUA10

Tax Info

  • Tax Annual Amount: 20690.17
  • Tax Lot: 14
  • Tax Year: 2025

Map

Range of Values:

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Value Increase
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $20,690 $1,381,260
2024 $19,795 $1,341,030
2023 $18,628 $1,301,980 $0 $0
2022 $17,045 $1,217,850 $0 $0
2021 $17,150 $1,182,380 $0 $0
2020 $16,192 $1,182,380 $0 $0
2019 $15,735 $1,147,950 $0 $0
2018 $15,275 $1,114,520 $0 $0
2017 $14,872 $1,082,060 $0 $0
2016 $14,130 $1,050,550 $0 $0
2015 $13,733 $1,019,960 $0 $0
2014 $13,292 $990,260 $0 $0
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
07/10/2026 07/10/26 Price Changed $2,850,000 -3.4% $516 / Sq Ft
05/27/2026 05/27/26 For Sale $2,950,000 -- $534 / Sq Ft
Source: Oregon Datashare

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Warranty Deed $2,550,000 Western Title
Source: Public Records

Source: Oregon Datashare

MLS Number: 220222189

Oregon Datashare

APN: 154885

Oregon Deschutes County Bend 97703

20180 Winston Loop, Bend, OR

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Betsey Leever Little
Listing Agent
Betsey Leever Little
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Cascade Hasson SIR
(458) 203-3242
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