20110 Winston Loop, Bend, OR 97703
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Property image
OFF MARKET

20110 Winston Loop
Bend, OR 97703

  • 4 Beds
  • 4 Baths
  • 4,122 sqft (on 5 acres)

$2,137,700

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $11,911/mo*
Refinance Your Home

$2,137,700

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $11,911/mo*
Refinance Your Home
4 Beds
4 Baths
4,122 sqft
(on 5 acres)

Home Value

Trulia Estimate
$2.14M
Since last month
Decreased$3K (-0.2%)
Since last year
$1K (0%)
Since last sale
Increased$7K (+0.3%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$2.14M
July 2026$2.15M
June 2026$2.19M
May 2026$2.16M
April 2026$2.17M
March 2026$2.17M
February 2026$2.11M
January 2026$2.08M
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
65020 Swalley Rd, Bend, OR
0.52
Single-Family Home
$2,143,633
12/19/25
5
4
5,627
65070 Swalley Rd, Bend, OR
0.66
Single-Family Home
$2,143,633
12/19/25
5
4
4,601
65057 Hopper Rd, Bend, OR
0.62
Single-Family Home
$1,275,000
03/10/26
4
5
4,011
65025 Wapiti Way, Bend, OR
0.54
Single-Family Home
$1,400,000
05/28/26
4
2
2,367
64520 El Dorado Trl, Bend, OR
0.62
Single-Family Home
$925,000
11/10/25
3
3
2,541
20087 Beaver Ln, Bend, OR
0.53
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
20123 Elder Ln, Bend, OR
0.67
Single-Family Home
$1,125,000
07/27/26
4
3
2,092
65010 Gerking Market Rd, Bend, OR
1.28
Single-Family Home
$1,200,000
01/09/26
3
4
2,416

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
20100 Winston Loop, Bend, OR 97703
0.07
$1,111,200
3
3
2,036
Off Market
20124 Tumalo Rd, Bend, OR 97703
0.17
$1,588,600
3
3
3,768
Off Market
64885 Simon Rd, Bend, OR 97703
0.22
$2,242,400
5
5
4,593
Off Market
64840 Simon Rd, Bend, OR 97703
0.22
$1,824,300
4
4
3,137
Off Market
64840 Simon Rd, Bend, OR 97703
0.24
$1,662,000
4
3
3,137
Off Market
20150 Winston Loop, Bend, OR 97703
0.25
$1,941,100
4
4
4,253
Off Market
20040 Tumalo Rd, Bend, OR 97703
0.30
$4,536,800
6
6
7,004
Off Market
20160 Winston Ct, Bend, OR 97703
0.31
$1,398,500
3
5
3,694
Off Market
64892 Simon Rd, Bend, OR 97703
0.33
$2,074,400
4
4
4,330
Off Market
20036 Tumalo Rd, Bend, OR 97702
0.37
$2,280,100
4
4
3,589
Off Market
20038 Tumalo Rd, Bend, OR 97703
0.37
$2,174,900
6
4
3,924
Off Market

Local Information

  • Map ViewExplore the area around 20110 Winston Loop.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
5 acres
Living Area
4,122 sqft
Price/Sqft
$519
Parking
3 Car Garage
HOA
$250/Monthly

About this House

This stunning french country estate spans 5 full irrigated acres in the highly sought-after Winston Ranch area of Tumalo. The property offers dramatic views of the Cascade mountains, visible from nearly every window of the house. the home boast high-end finishes, including slab granite countertops, hardwood floors, large windows and a spectacular basalt rock fireplace. The completely remodelled kitchen is a must-see with high-end appliances, a double island, wine refrigerator and more. The primary suite is located upstairs, with guest bedrooms on the main floor and a 4th bedroom / flex room with adjoining ensuite over the garage. The private and unique setting includes a 3-stall barn, dry lt for horses, a shop with garage and RV/boat carport, underground irrigation, and a round pen adjacent to the lush, fenced pasture. This turn-key property is located just minutes from bend, offers a perfect blend of luxury and rural charm in Winston Ranch.
20110 Winston Loop, Bend, OR 97703 is a 4 bedroom, 4 bathroom, 4,122 sqft single-family home built in 1994. It last sold for $2,137,000 on Jun 30, 2025 (11% below the $2,400,000 asking price). It is currently off market. The Trulia Estimate is $2,137,700, with a rent estimate of $6,662/month.
Last check for updates: about 19 hours ago
Listed by Keller Williams Realty Central Oregon, (541) 585-3760
Bought with: Realty One Group Discovery, (541) 645-0244
Source: Oregon Datashare, MLS#220198720

Home Details for 20110 Winston Loop

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: NoneWet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4
Dimensions and Layout
Living Area: 4122 Square Feet
Appliances & Utilities
Appliances: Cooktop, Dishwasher, Disposal, Microwave, Oven, Refrigerator, Trash Compactor, Water Heater, Wine RefrigeratorDishwasherDisposalMicrowaveRefrigerator
Heating & Cooling
Heating: Electric,Forced Air,Heat Pump,PropaneHas CoolingAir Conditioning: Central Air,Heat PumpHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: PropaneSpa: Indoor Spa/Hot Tub, Spa/Hot TubHas a Fireplace
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Vinyl FramesFlooring: Carpet, Hardwood, TileCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Hardwood, Tile
View
Has a ViewView: Mountain(s)
Security
Security: Carbon Monoxide Detector(s), Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: DeckFencing: FencedOther Structures: Animal Stall(s), RV/Boat Storage, Second Garage, Stable(s), WorkshopFoundation: Stemwall
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Asphalt,Attached,Driveway,Garage Door Opener,Paver Block,RV Garage,Workshop in Garage
Frontage
Road Frontage: Shared AccessRoad Surface Type: Paved
Water & Sewer
Sewer: Septic Tank
Farm & Range
Acres Incl in Water Rights: 5Allowed to Raise HorsesIncludes Irrigation Water Rights

Days on Market

Cumulative Days on Market: 41

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Tudor
Building
Construction Materials: FrameNot a New ConstructionNo Additional Parcels
Property Information
Included in Sale: Refrigerator, Entertainment Center in Family RoomParcel Number: 154846

Price & Status

Price
List Price: $2,400,000
Status Change & Dates
Off Market Date: Thu May 15 2025

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

Building

Building Area
Building Area: 4122 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $3,003/Annually

Lot Information

Lot Area: 5 Acres

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 220198720

Additional Information

HOA Amenities: Snow Removal

Price and Tax history

DateEventPrice
Jun 30, 2025
Source: Oregon Datashare #220198720
Sold
$2,137,000
May 15, 2025
Source: Oregon Datashare #220198720
Pending
$2,400,000
Apr 4, 2025
Source: Oregon Datashare #220198720
Listed For Sale
$2,400,000
Oct 14, 2024
Source: Oregon Datashare #220187305
ListingRemoved
$2,400,000
Sep 24, 2024
Source: Oregon Datashare #220187305
PriceChange
$2,400,000
Price decreased by 8%

Market trends in Bend

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$813K
$36KMoM
Sale-to-List Price
99.2%
0.1%MoM
Price per sq ft
$422
$7MoM
Available listings
1083
20MoM

Around this home

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 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.
  • Cara C.
    "Safe neighborhood. Lots of families. Multiple trails and outdoor areas to recreate just out your door. "
    0
    Flag
  • 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
    Flag
  • 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!"
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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
    Flag
  • 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
    Flag
  • Bart
    "It’s a fantastic place to live and recreate. Neighbors are terrific, and the homes are beautiful. So lucky to be here."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Maxorsini
    "Good place and safe place for kids. The park it’s really nice and the neighborhood it’s clean and safe."
    0
    Flag
  • 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
  • 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
    Flag
  • Melissa
    "Pretty private and quiet. No community events but has old Bend charm and feel. Super convenient to stores but then so peaceful. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

© 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 2026-08-22 00:15:05 PDT

Frequently asked questions about 20110 Winston Loop

  • What is 20110 Winston Loop estimated to be worth?
    Trulia's estimated value for 20110 Winston Loop in Bend, OR is $2,137,700.
  • What is the price history for 20110 Winston Loop?
    20110 Winston Loop in Bend, OR last sold for $2,137,000 in June 2025.
  • Is Bend a buyer's or seller's market?
    Bend is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Bend?
    The median sale price in Bend is $813K. That is up $36K from the prior month.
  • Does 20110 Winston Loop have air conditioning?
    Yes, 20110 Winston Loop in Bend, OR has air conditioning.
  • Does 20110 Winston Loop have a yard?
    Yes, 20110 Winston Loop in Bend, OR has a yard.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Off Market Homes Near 20110 Winston Loop

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