20185 Winston Loop, Bend, OR 97703
Property image
Property image
OFF MARKET

$1,855,900

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,740 sqft (on 7.50 acres)

20185 Winston Loop, Bend, OR 97703

Est. Refi. Payment $11,176/mo*
Refinance Your Home
Currently Off Market - Sold Jul 13, 2020 for $1,610,000

Home Value

Trulia Estimate
$1.86M
Since last month
Increased$4K (+0.2%)
Since last year
Decreased$21K (-1.1%)
Since last sale
Increased$242K (+15%)
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 +160% in the last 10 years
MonthEstimated value
2026
September 2026$1.85M
August 2026$1.85M
July 2026$1.86M
June 2026$1.9M
May 2026$1.88M
April 2026$1.87M
March 2026$1.87M
February 2026$1.83M
January 2026$1.82M
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
64520 El Dorado Trl, Bend, OR
0.36
Single-Family Home
$925,000
11/10/25
3
3
2,541
64520 El Dorado Trl, Bend, OR
0.37
Single-Family Home
$925,000
11/10/25
3
3
2,541
20087 Beaver Ln, Bend, OR
0.71
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
20087 Beaver Ln, Bend, OR
0.71
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
65025 Wapiti Way, Bend, OR
0.79
Single-Family Home
$1,400,000
05/28/26
4
2
2,367
64810 Bill Martin Rd, Bend, OR
1.15
Single-Family Home
$1,375,000
11/07/25
4
3
3,204
64810 Bill Martin Rd, Bend, OR
1.15
Single-Family Home
$1,375,000
11/07/25
4
3
3,204
64727 Hunnell Rd, Bend, OR
1.00
Single-Family Home
$1,010,000
05/15/26
3
2
1,851
65015 Hopper Rd, Bend, OR
0.71
Single-Family Home
$800,000
09/21/26
3
2
1,748
65020 Swalley Rd, Bend, OR
0.81
Single-Family Home
$2,143,633
12/19/25
5
4
5,627

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
20180 Winston Loop, Bend, OR 97703
0.10
$2,850,000
5
4
5,528
For Sale
20160 Winston Ct, Bend, OR 97703
0.16
$1,416,100
3
5
3,694
Off Market
20150 Winston Loop, Bend, OR 97703
0.18
$2,005,900
4
4
4,253
Off Market
64635 Simon Rd, Bend, OR 97703
0.19
$1,692,900
4
3
2,909
Off Market
20110 Winston Loop, Bend, OR 97703
0.29
$2,086,700
4
4
4,122
Off Market
20100 Winston Loop, Bend, OR 97703
0.32
$1,098,800
3
3
2,036
Off Market
20124 Tumalo Rd, Bend, OR 97703
0.37
$1,595,800
3
3
3,768
Off Market
64520 El Dorado Trl, Bend, OR 97703
0.36
$906,500
3
3
2,541
Off Market
19975 Tumalo Rd, Bend, OR 97703
0.38
-
-
-
-
Off Market
64840 Simon Rd, Bend, OR 97703
0.43
$1,859,600
4
4
3,137
Off Market
20040 Tumalo Rd, Bend, OR 97703
0.40
$4,739,500
6
6
7,004
Off Market
20036 Tumalo Rd, Bend, OR 97702
0.41
$2,392,700
4
4
3,589
Off Market

Local Information

  • Map ViewExplore the area around 20185 Winston Loop.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
7.5 acre lot
2,740 sqft
$677/sqft
Garage

About this House

Panoramic 8 white Cascade Mountain views. Spectacular newly redone single level NW ranch home located in Tumalo. Vaulted great room plan w/floor to ceiling windows to stunning Cascade Mountain views. 3 full bedrooms & baths plus office. Full interior remodel 2019. Knotty Alder cabinetry throughout home. All counters granite or Caesar stone. Floor to ceiling dry stack stone fireplace. Kitchen w/slab granite island, informal bar seating, Jenn Air gas cooktop, Bosch appliances, Blanco sink, pantry. Wonderful master suite w/views. Bath w/in-floor radiant heat, European shower. Eagle Creek Prestigious Collection engineered hickory hardwood front & back decks. Waterfall/creek w/Koi fish pond. Presidential roof, new exterior paint & gutters, new well pump 2018, 3-car oversized garage. Shrubbery/flowers auto drip/auto sprinklers. Lush irrigated fenced pasture on 2 sides, 6.6 irrigated acres. Mountain views are protected in CC&R's. Assessor 2374 SF doesn't include 366 SF permitted 2008 office.
20185 Winston Loop, Bend, OR 97703 is a 3 bedroom, 3 bathroom, 2,740 sqft single-family home built in 1996. It last sold for $1,610,000 on Jul 13, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,855,900, with a rent estimate of $4,504/month.

Home Details for 20185 Winston Loop

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Lot Information

Lot Area: 7.50 acres

Price and Tax history

DateEventPrice
Jul 14, 2020
Source: Agent Provided
ListingRemoved
$1,395,000
Jul 14, 2020
Source: Agent Provided
Listed For Sale
$1,395,000
Jul 13, 2020
Source: Oregon Datashare #220103698
Sold
$1,610,000
Jul 2, 2020
Source: Agent Provided
Pending
$1,395,000
Jun 26, 2020
Source: Agent Provided
Listed For Sale
$1,395,000

Market trends in Bend

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$823K
$10KMoM
Sale-to-List Price
99.0%
0.2%MoM
Price per sq ft
$423
$1MoM
Available listings
1097
12MoM

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
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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!"
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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
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  • Roesslerc
    "Great town. Close to mountains but currently over priced. Very worried about the future of home worth in this market "
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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
    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
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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
    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
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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
    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
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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."
    2
    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. "
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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

Frequently asked questions about 20185 Winston Loop

  • What is 20185 Winston Loop estimated to be worth?
    Trulia's estimated value for 20185 Winston Loop in Bend, OR is $1,855,900.
  • What is the price history for 20185 Winston Loop?
    20185 Winston Loop in Bend, OR last sold for $1,610,000 in July 2020.
  • 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 $823K. That is up $10K from the prior month.
  • How big is the lot at 20185 Winston Loop?
    The lot at 20185 Winston Loop in Bend, OR is about 7.5 acres.
  • Does 20185 Winston Loop have a garage?
    Yes, 20185 Winston Loop in Bend, OR has a garage.

Explore by feature - Pet Friendly

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Off Market Homes Near 20185 Winston Loop

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