$2,850,000
Original price: $2,950,000
5 Beds
4 Baths
5,528 sqft (on 7.46 acres)
20180 Winston Loop, Bend, OR 97703
Est. Mortgage $16,235/mo*
Get Pre-QualifiedHome Highlights
Parking
6 Car Garage
Outdoor
Pool
HOA
$395/Monthly
Price/Sqft
$516
Climate Control
Forced Air, Heat Pump & Central Air
Listed
91 days ago
Local Information
- Map ViewExplore the area around 20180 Winston Loop.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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.
Last check for updates: about 1 hour ago
Listing courtesy of Cascade Hasson SIR, (541) 383-7600
Source: Oregon Datashare, MLS#220222189
Also Listed on Oregon Datashare.
Open House
Saturday, August 29
11:00 AM to 1:00 PM
Home Details for 20180 Winston Loop
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MLS Status: Active |
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Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 4 |
Dimensions and Layout Living Area: 5528 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Electric,Forced Air,Heat Pump,ZonedHas CoolingAir Conditioning: Central Air,Heat Pump,ZonedHas HeatingHeating Fuel: Electric |
Fireplace & Spa Fireplace: Great Room, Office, PropaneHas a Fireplace |
Windows, Doors, Floors & Walls Window: Double Pane WindowsFlooring: Carpet, Hardwood, StoneCommon Walls: No Common Walls |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Carpet, Hardwood, Stone |
View Has a ViewView: Mountain(s), Panoramic, Territorial |
Security Security: Carbon Monoxide Detector(s), Fire Sprinkler System, Security System Owned, Smoke Detector(s) |
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Exterior Home Features Roof: TilePatio / Porch: CoveredOther Structures: RV/Boat Storage, Second Garage, Storage, WorkshopExterior: Built-in Barbecue, RV Dump, RV HookupFoundation: StemwallHas a Private Pool |
Parking & Garage Number of Garage Spaces: 6Number of Covered Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Asphalt,Attached,Detached,Driveway,Garage Door Opener,RV Access/Parking,RV Garage,Tandem,Workshop in Garage |
Pool Pool: Heated, In Ground, Pool CoverPool |
Frontage Road Frontage: Private AccessRoad Surface Type: Paved |
Water & Sewer Sewer: Septic Tank, Standard Leach Field |
Farm & Range Acres Incl in Water Rights: 6.4Allowed to Raise HorsesIncludes Irrigation Water Rights |
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Cumulative Days on Market: 90Days on Market: 91 |
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Year Built Year Built: 2000 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Northwest,Traditional |
Building Construction Materials: FrameNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 154885 |
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Price List Price: $2,850,000Price Per Sqft: $516 |
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Direction & Address City: BendCommunity: Winston Ranch |
School Information Elementary School: North Star ElementaryJr High / Middle School: Sky View MiddleHigh School: Mountain View Sr High |
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Listing Agent Listing ID: 220222189 |
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Building Area Building Area: 5528 Square Feet |
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Not Senior Community |
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Has an HOAHOA Fee: $395/Monthly |
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Lot Area: 7.46 Acres |
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Special Conditions: Standard |
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Listing Terms: Cash, Conventional |
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Mls Number: 220222189 |
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HOA Amenities: Snow Removal |
Around this home
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.
What Locals Say about Bend
At least 666 Trulia users voted on each feature.
90 % Say it's dog friendly
84 % Say car is needed
79 % Say people would walk alone at night
78 % Say yards are well-kept
77 % Say parking is easy
75 % Say there's wildlife
75 % Say there's holiday spirit
71 % Say kids play outside
68 % Say it's quiet
68 % Say there are sidewalks
57 % Say neighbors are friendly
53 % Say they plan to stay for at least 5 years
48 % Say it's walkable to restaurants
42 % Say it's walkable to grocery stores
33 % Say streets are well-lit
30 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
Market trends in Bend
Last updated July 2026
Avg. sale price
$813K
$36KMoM
Sale-to-List Price
99.2%
0.1%MoM
Price per sq ft
$422
$7MoM
Available listings
1083
20MoM
Home Value
Trulia Estimate
$2.69MSince last month
Increased$2K (+0.1%)Since last year
Increased$121K (+4.7%)Since last sale
Increased$145K (+5.7%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +80% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $2.7M |
| July 2026 | $2.69M |
| June 2026 | $2.81M |
| May 2026 | $2.93M |
| April 2026 | $2.86M |
| March 2026 | $2.54M |
| February 2026 | $2.54M |
| January 2026 | $2.53M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.86 | Single-Family Home | $2,143,633 | 12/19/25 | 5 | 4 | 5,627 | |
0.39 | Single-Family Home | $925,000 | 11/10/25 | 3 | 3 | 2,541 | |
1.00 | Single-Family Home | $2,143,633 | 12/19/25 | 5 | 4 | 4,601 | |
1.06 | Single-Family Home | $1,375,000 | 11/07/25 | 4 | 3 | 3,204 | |
0.86 | Single-Family Home | $1,275,000 | 03/10/26 | 4 | 5 | 4,011 | |
0.80 | Single-Family Home | $1,400,000 | 05/28/26 | 4 | 2 | 2,367 | |
0.69 | Single-Family Home | $1,150,000 | 01/09/26 | 3 | 3 | 2,525 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.10 | $1,430,900 | 3 | 5 | 3,694 | Off Market | |
0.16 | $1,987,900 | 4 | 4 | 4,253 | Off Market | |
0.17 | $1,721,000 | 4 | 3 | 2,909 | Off Market | |
0.28 | - | - | - | - | Off Market | |
0.35 | $2,090,900 | 4 | 4 | 4,122 | Off Market | |
0.39 | $1,132,900 | 3 | 3 | 2,036 | Off Market | |
0.37 | $2,271,400 | 4 | 4 | 3,589 | Off Market | |
0.39 | $1,630,400 | 3 | 3 | 3,768 | Off Market | |
0.38 | $4,599,700 | 6 | 6 | 7,004 | Off Market | |
0.35 | $821,000 | 3 | 2 | 1,580 | Off Market | |
0.37 | $850,300 | 3 | 3 | 1,702 | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jul 10, 2026 Source: Oregon Datashare #220222189 | PriceChange | $2,850,000 Price decreased by 3% |
May 27, 2026 Source: Oregon Datashare #220222189 | Listed For Sale | $2,950,000 |
Oct 7, 2025 Source: Oregon Datashare #220206606 | ListingRemoved | $2,700,000 |
Sep 26, 2025 Source: Oregon Datashare #220206606 | Pending | $2,700,000 |
Jul 29, 2025 Source: Oregon Datashare #220206606 | Listed For Sale | $2,700,000 |
Mar 2, 2022 Source: N/A | Sold | $2,550,000 |
Sep 2, 2021 Source: Oregon Datashare #220119471 | ListingRemoved | |
Jul 19, 2021 Source: Oregon Datashare #220119471 | PriceChange | $2,600,000 Price decreased by 2% |
Jun 21, 2021 Source: Oregon Datashare #220119471 | PriceChange | $2,650,000 Price decreased by 4% |
Apr 2, 2021 Source: Oregon Datashare #220119471 | Listed For Sale | $2,750,000 |
Oct 6, 2020 Source: Agent Provided | ListingRemoved | $2,500,000 |
Jul 8, 2020 Source: Agent Provided | Listed For Sale | $2,500,000 |
Oct 13, 2018 Source: Agent Provided | ListingRemoved | $2,399,999 |
Jul 12, 2018 Source: Agent Provided | Listed For Sale | $2,399,999 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $20,690 | $2,884,350 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Cascade Hasson SIR, (541) 383-7600
© 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 Zillow Inc. 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. This content has last been updated on 2026-08-25 23:52:31 PDT
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Frequently asked questions about 20180 Winston Loop
- What is the estimated monthly payment for 20180 Winston Loop?Based on a $2,850,000 list price with 20% down at today's rates, the estimated monthly payment for 20180 Winston Loop in Bend, OR is approximately $16,255 (about $14,826 principal & interest, $1,354 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 20180 Winston Loop compare to homes in Bend?20180 Winston Loop in Bend, OR is listed at $2,850,000, about 250% above the $813K median sale price in Bend.
- What do residents say about Bend?Residents describe Bend, OR as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Bend, OR.
- What are the closest schools to 20180 Winston Loop?The closest schools to 20180 Winston Loop in Bend, OR are Mountain View Senior High School (rated 7/10), North Star Elementary (rated 8/10), Sky View Middle School (rated 7/10).
- Does 20180 Winston Loop have air conditioning?Yes, 20180 Winston Loop in Bend, OR has air conditioning.
- Does 20180 Winston Loop have a pool?Yes, 20180 Winston Loop in Bend, OR has a pool.
20180 Winston Loop, Bend, OR 97703 is a 5 bedroom, 4 bathroom, 5,528 sqft single-family home built in 2000. This property is currently available for sale and was listed by Oregon Datashare on May 27, 2026. The MLS # for this home is MLS# 220222189.