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$2,950,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 5,528 Sq. Ft.
  • 6 Car Garage
  • Updated 11 days ago
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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.

Full Property Details for 20180 Winston Loop

General

  • Price: $2,950,000
  • HOA FEE: $395/month
  • Taxes: $20,690 (2025)
  • Status: Active
  • Type: Single Family
  • Source: ODS
  • MLS ID: 220222189
  • Updated: 5/27/2026
  • Added to Site: 12 day(s) ago

Interior

  • Rooms/Areas: Bonus Room, Dining Room, Eating Area, Laundry, Kitchen, Office, Living Room, Primary Room
  • Interior 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)
  • Fireplace: Yes
  • Fireplace(s): Great Room, Office, Propane
  • Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • Flooring: Carpet, Hardwood, Stone

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5

Additional Information

  • Shared Amenities: Snow Removal
  • Pool Description: Heated, In Ground, Pool Cover
  • Security/Safety: Carbon Monoxide Detector(s), Fire Sprinkler System, Security System Owned, Smoke Detector(s)

Parking

  • Garage: Yes
  • Garage Spaces: 6
  • Parking Features: Asphalt, Attached, Detached, Driveway, Garage Door Opener, RV Access/Parking, RV Garage, Tandem, Workshop in Garage
  • Parking: Primary Suite, Attached, Detached, Driveaway, Garage Door Opener

Location

  • Area: 5528
  • County: Deschutes
  • Subdivision: Winston Ranch
  • Cross Streets: Tumalo Road

School Information

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

Community

  • Community Features: Snow Removal
  • Association: Yes
  • Home Owners Assn.: 1

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air, Heat Pump, Zoned
  • Heating Type: Electric, Forced Air, Heat Pump, Zoned

Utilities

  • Sewer: Septic Tank, Standard Leach Field
  • Water: Well
  • Well: Yes

Structural Information

  • Architectural Style: Northwest, Traditional
  • Construction: Frame
  • Exterior Const.: Built-in Barbecue, RV Dump, RV Hookup
  • Foundation: Stemwall
  • Roof: Tile
  • Common Walls: No Common Walls
  • Windows: Double Pane Windows
  • Stories/Levels: 2
  • Square Feet: 5,528
  • Sq. Ft. Source: Assessor
  • Living Area: 5,528 Sq. Ft.
  • Year Built: 2000

Additional Structures

  • Other Structures: RV/Boat Storage, Second Garage, Storage, Workshop

Lot Features

  • Property View: Cascade Mountains, Panoramic, Territorial
  • Mountain views: Yes
  • Lot Size (Acres): 7.46
  • Lot Size (Sq. Ft.): 324,958
  • Frontage: Private Access
  • Street/Road Desc.: Paved
  • Irrigation System: District
  • Lot Features: Landscaped, Level, Pasture, Sprinkler Timer(s), Sprinklers In Front, Sprinklers In Rear
  • Zoning: MUA10

Horse Property

  • Horse Property: Yes

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $395
  • Assoc Fee Freq.: Monthly
  • Tax Amount: $20,690.17
  • Tax Year: 2025
  • Terms: Cash, Conventional

Disclosures and Reports

  • Special Conditions: Standard
  • APN: 154885
  • Section: NW
  • Lot Number: 14

Listed by Cascade Hasson SIR (541) 383-7600, Betsey Leever Little (541) 301-8140

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Listing agent

— 20180 Winston Loop —

  • Betsey Leever Little

    Cascade Hasson SIR

    541-383-7600

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NMLS#: 1598647

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NMLS#: 1598647

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Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 20180 Winston Loop

School District:Bend-la Pine Administrative School District 1
NameGradesDistance
North Star Elementary
63567 N.W. Brownrigg Road, Bend, OR 97703
K-52.9 mi
Sky View Middle School
63555 Northeast 18th Street, Bend, OR 97701
6-83.6 mi
Mountain View Senior High School
2755 Northeast 27th Street, Bend, OR 97701
9-125.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20180 Winston Loop Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/27/2026
Listed
$2,950,000
15.69%
MLS
2/01/2022
Sold
$2,550,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 20180 Winston Loop

Year
Property Taxes
Change
Tax Assessment
Change
2025
$20,690
5%
$1,381,260
3%
2024
$19,795
6%
$1,341,030
3%
2023
$18,628
9%
$1,301,980
7%
2021
$17,150
-2%
$1,217,850
—
2022
$17,573
2%
$1,217,850
3%
2021
$17,150
9%
$1,182,380
3%
2019
$15,735
3%
$1,147,950
3%
2018
$15,275
3%
$1,114,520
3%
2017
$14,872
5%
$1,082,060
3%
2016
$14,130
3%
$1,050,550
3%
2015
$13,733
3%
$1,019,960
3%
2014
$13,292
5%
$990,260
3%
2013
$12,682
—
$961,420
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Cascade Hasson SIR (541) 383-7600, Betsey Leever Little (541) 301-8140

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Price Reduced near 20180 Winston Loop

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Listed by Cascade Hasson SIR, Karen A Wilson
Sold by Cascade Hasson SIR, Brian John Ladd

20180 Winston Loop, Bend, OR 97703 (MLS# 220222189) is a Single Family property with 5 bedrooms and 4 full bathrooms. 20180 Winston Loop is currently listed for $2,950,000 and was received on May 27, 2026. Want to learn more about 20180 Winston Loop? Do you have questions about finding other Single Family real estate for sale in Bend? You can browse all Bend real estate or contact a Coldwell Banker agent to request more information.

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