Listed by: Betsey Leever Little · Cascade Hasson SIR

$2,850,000Price cut $100,000
  • 5 beds
  • 4 baths
  • 5,528 sqft

20180 Winston Loop, Bend, OR 97703

Est. $17,124/moPayment calculator
  • Single Family ResidenceHome type
  • Built in 2000Year built
  • 7.46 acresLot
  • $516/sqftPrice per sqft
  • $395/moHOA
  • 6-car garageParking

About this home

  • Listed May 27, 2026
  • 128 days on market
  • 62 photos

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.

Facts & features

Interior

Bedrooms
5
Bathrooms
4
Full bathrooms
4
Living area
5,528 sqft
Levels
Two

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)

Appliances

  • Dishwasher
  • Dryer
  • Microwave
  • Oven
  • Range
  • Refrigerator
  • Washer

Heating & cooling

  • Electric
  • Forced Air
  • Heat Pump
  • Zoned
  • Central Air
  • Heat Pump
  • Zoned

Flooring

  • Carpet
  • Hardwood
  • Stone

Property

Lot size
7.46 acres
Garage spaces
6
Subdivision
Winston Ranch

Exterior features

  • Built-in Barbecue
  • RV Dump
  • RV Hookup

View

  • Cascade Mountains
  • Panoramic
  • Territorial

Parking

  • Asphalt
  • Attached
  • Detached
  • Driveway
  • Garage Door Opener
  • RV Access/Parking
  • RV Garage
  • Tandem
  • Workshop in Garage

Construction

Home type
Single Family Residence
Property type
Residential
Year built
2000

Materials

  • Frame
  • Tile roof

Utilities

Sewer & water

  • Septic Tank
  • Standard Leach Field
  • Well water

Community & HOA

Subdivision
Winston Ranch
HOA dues
$395 monthly
County
Deschutes

Financial & listing details

List price
$2,850,000
Original list price
$2,950,000
Price per sqft
$516
Annual property tax
$20,690
Date on market
May 27, 2026
Days on market
128
MLS#
220222189

Price & status history

DateEventPrice
May 27, 2026Listed for sale$2,950,000

Neighborhood

  • SubdivisionWinston Ranch
  • CityBend, OR 97703
  • CountyDeschutes

Payment calculator

Estimated monthly payment

$17,124/mo

  • Principal & interest$14,411
  • Property taxes$1,724
  • Homeowners insurance$594
  • HOA dues$395

Loan amount $2,280,000 · 30-year fixed at 6.5%

Down payment
Loan term

An estimate for planning, not a loan offer. The 6.5% rate is an example; ask a lender for today’s rate. Taxes use the listing’s annual tax amount. Insurance is estimated; mortgage insurance is not included.

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MLSCO

Listing provided by Cascade Hasson SIR · Listing agent: Betsey Leever Little

Source
MLS of Central Oregon
MLS#
220222189
Last updated
Aug 29, 2026 at 11:34 PM

Listing information is deemed reliable but not guaranteed and should be independently verified. Listings shown are for demonstration while our MLS of Central Oregon IDX feed is being set up.