20180 Winston Loop, Bend, OR 97703
FOR SALE
NEW - 2 HRS AGO
3D VIEW
7.46 ACRES

20180 Winston Loop
Bend, OR 97703

  • 5 Beds
  • 4 Baths
  • 5,528 sqft (on 7.46 acres)

$2,950,000

Est. Mortgage $16,664/mo*
Get Pre-Qualified

$2,950,000

Est. Mortgage $16,664/mo*
Get Pre-Qualified
5 Beds
4 Baths
5,528 sqft
(on 7.46 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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 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.

Home Highlights

Parking
6 Car Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
$395/Monthly
Price/Sqft
$534
Listed
No Info

Home Details for 20180 Winston Loop

Active Status

MLS Status: Active

Interior Features

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)

Exterior Features

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

Days on Market

Days on Market: <1 days on Trulia

Property Information

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

Price & Status

Price
List Price: $2,950,000Price Per Sqft: $534

Media

Location

Direction & Address
City: BendCommunity: Winston Ranch
School Information
Elementary School: North Star ElementaryJr High / Middle School: Sky View MiddleHigh School: Mountain View Sr High

Agent Information

Listing Agent
Listing ID: 220222189

Building

Building Area
Building Area: 5528 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $395/Monthly

Lot Information

Lot Area: 7.46 Acres

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 220222189

Additional Information

HOA Amenities: Snow Removal
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.

Price History for 20180 Winston Loop

DatePriceEventSource
05/27/2026$2,950,000Listed For SaleOregon Datashare #220222189
10/07/2025$2,700,000ListingRemovedOregon Datashare #220206606
09/26/2025$2,700,000PendingOregon Datashare #220206606
07/29/2025$2,700,000Listed For SaleOregon Datashare #220206606
03/02/2022$2,550,000Sold
N/A
09/02/2021ListingRemovedOregon Datashare #220119471
07/19/2021$2,600,000PriceChange
Oregon Datashare #220119471
06/21/2021$2,650,000PriceChange
Oregon Datashare #220119471
04/02/2021$2,750,000Listed For SaleOregon Datashare #220119471
10/06/2020$2,500,000ListingRemovedAgent Provided
07/08/2020$2,500,000Listed For SaleAgent Provided
10/13/2018$2,399,999ListingRemovedAgent Provided
07/12/2018$2,399,999Listed For SaleAgent Provided

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Property Tax and Assessment

Year2025
Tax$20,690
Assessment$2,884,350
Home facts updated by county records

Comparable Sales for 20180 Winston Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20110 Winston Loop, Bend, OR
0.35
Single-Family Home
$2,137,000
06/30/25
4
4
4,122
65020 Swalley Rd, Bend, OR
0.86
Single-Family Home
$2,143,633
12/19/25
5
4
5,627
64520 El Dorado Trl, Bend, OR
0.39
Single-Family Home
$925,000
11/10/25
3
3
2,541
65070 Swalley Rd, Bend, OR
1.00
Single-Family Home
$2,143,633
12/19/25
5
4
4,601
64810 Bill Martin Rd, Bend, OR
1.06
Single-Family Home
$1,375,000
11/07/25
4
3
3,204
20019 Beaver Ln, Bend, OR
0.57
Single-Family Home
$1,162,000
07/21/25
3
3
3,934
65057 Hopper Rd, Bend, OR
0.86
Single-Family Home
$1,275,000
03/10/26
4
5
4,011
65130 Highland Rd, Bend, OR
1.14
Single-Family Home
$1,690,000
06/17/25
3
3
3,207

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 20180 Winston Loop.
View nearby schools on GreatSchools
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 665 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.
  • Daemon Heydon
    "Great place to live, relax and enjoy the outdoors. Lived here in the 80’s and moved back 8 years ago. Bigger but still lovely."
    0
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  • Crystal
    "I have lived many places yet this neighborhood makes me feel it is the safest I have ever lived in. I am female and regularly walk to restaurants, grocery stores, music halls, Downtown Bend, Drake Park etc and I always feel safe and feel a sense of community and caring for others and our furry friends. The sense of community is amazing and genuine!"
    0
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  • Anne B Christmas
    "I have miles and miles of trails outside my house. It’s perfect for dogs. There are areas that are wonderful for off leash running Wonderful for off leash running. "
    0
    Flag
  • Rome Hill
    "The people are nice and so are the dogs. Would love to live here. Great people, great community. I love this neighborhood"
    0
    Flag
  • Roesslerc
    "Great town. Close to mountains but currently over priced. Very worried about the future of home worth in this market "
    0
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  • Christopher.parsonst
    "Dogs seem super welcome. I love it immensely. Lots of great trails nearby. Summer is amazing and being near downtown makes everything so walkable."
    0
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  • Angimoe
    "It’s very walkable and pets are welcome. Animals are on leashes and everyone cleans up after their dogs."
    0
    Flag
  • Annette Solis
    "I’ve lived here for an over a year. The location is excellent but overpriced and impossible to land a great spot."
    1
    Flag
  • Shanda
    "Quiet, family and pet friendly, lots of walkers and bicyclists, large lots, neighbors look out for each other. "
    0
    Flag
  • Lureesk
    "Car is needed for commute. However, there are parks and restaurants that you can walk to. Public transportation is available."
    0
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  • Bart
    "It’s a fantastic place to live and recreate. Neighbors are terrific, and the homes are beautiful. So lucky to be here."
    0
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  • Jonathan Trimm
    "I’ve lived here for 3 years and never had any problems with neighbors or their dogs. The houses are all well maintained and people take care of their property."
    1
    Flag
  • Joellee Davis
    "The Christmas parade and the Neighborhood hero Joey Johnson. Lots of space. We often see wildlife from our window. Tall forest trees "
    0
    Flag
  • SD
    "Quiet & safe neighborhood where there are tons of kids of all ages out playing every day. Perfect neighborhood for a family"
    0
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  • Trulia User
    "You’ll love the new off leash dog park at Alpenglow Park! There are also lots of trails in the area."
    1
    Flag
  • Trulia User
    "I’ve lived here about 18 months. It’s a nice, convenient neighborhood. The Larkspur and Alpenglow parks add so much to the quality of life. "
    2
    Flag
  • Trulia User
    "Private setting, and kids can play freely in the cul-de-sac. Great neighborhood. All the neighbors are all good friends."
    0
    Flag
  • Trulia User
    "It’s a community. People watch out for each other. Children have others to play with. Pet friendly. "
    1
    Flag
  • Trulia User
    "Neighbors are interested in being neighborly. We share garden bounty, help each other out, care about being a friendly community."
    1
    Flag
  • Trulia User
    "There are sidewalks in most neighborhoods, but not a great deal of shade. The new park, Aspenglow, has nice fenced areas for off-leash dogs. "
    0
    Flag
  • Trulia User
    "There is access to public transportation and within walking distance to shopping or the Old Mill District."
    1
    Flag
  • Trulia User
    "Good neighborhood for families and for getting to know bend and all its greatness. Very easy access to downtown and old mill district."
    0
    Flag
  • Trulia User
    "Very family friendly neighborhood with a park and and an elementary school within the neighborhood. "
    0
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  • Trulia User
    "lots of places to walk thru neighborhoods but lots of people have their dogs not leashed or don't pick up after their dog poop"
    0
    Flag
  • Trulia User
    "Amazing neighborhood to raise kids. Beautiful homes and well cared for. A lot of pride of ownership. "
    0
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  • Maxorsini
    "Good place and safe place for kids. The park it’s really nice and the neighborhood it’s clean and safe."
    0
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  • Michelle K.
    "Alley access means that sidewalks aren’t crossed with driveways. It’s very safe for kids riding bikes and walkers. "
    2
    Flag
  • Alexandra H.
    "Trick or treating is great and the neighbors are all very friendly. It’s a rather quiet neighborhood & there’s lots of kids around. Super family friendly "
    1
    Flag
  • Trulia User
    "Lots of families and family centered things to do in Bend. Good schools, lots of parks, wonderful community Parks and Recreation programs "
    0
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  • Phillip W.
    "my work is roughly 5 minutes away from home, easy freeway access. Living in Bend has gotten harder for commuting as population increased."
    2
    Flag
  • Cindee R.
    "Easy access to downtown Bend. Traffic is busy but walking is nice. Lots of great little stores around. "
    0
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  • Melissa
    "Pretty private and quiet. No community events but has old Bend charm and feel. Super convenient to stores but then so peaceful. "
    0
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  • Bryan B.
    "Easy commute. Hardly any traffic, easy to downtown, Redmond or shops in cascade shopping center. More characters here😋"
    2
    Flag
  • Sioux T.
    "beautiful peaceful homes in a area where you are 10 minutes from the heart of town but feel like you are in the middle of nowhere...."
    1
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  • Valdiviafam
    "Seems to have plenty of public transit. Traffic flows well. Easy access to highway and parkway. Area has roundabouts and lots of people in this area bike quite a bit."
    0
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  • Kathleen C.
    "Seems very neighborly- people seem to be open to meeting new people. The homes are a nice mix of small and large, old and new."
    1
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  • Andrewlangenbach
    "We have great friends to hat live here and know all the fun outdoor activities to do. This is a wonderful place for outdoor activities year round. "
    0
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  • Michelle
    "I love this neighborhood. Families are out playing ball with their kids and fur babies every day. Folks stop to say hello and shot the breeze any chance they can get. Their is truly a sense of community. "
    3
    Flag
  • Bucky H.
    "everyone here looks out for each other, I know my neighbors on a first name bases, and consider them friends."
    0
    Flag
  • Blake S.
    "Great place to live close to the rivers and hiking trails. The golf course is maintained and beautiful to play on. "
    0
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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 2026-05-27 12:21:03 PDT
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.