20101 Winston Loop, Bend, OR 97703
OFF MARKET

20101 Winston Loop
Bend, OR 97703

  • 5 Beds
  • 3 Baths
  • 3,973 sqft (on 5.61 acres)

$1,432,200

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $8,118/mo*
Refinance Your Home

$1,432,200

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $8,118/mo*
Refinance Your Home
5 Beds
3 Baths
3,973 sqft
(on 5.61 acres)

Local Information

  • Map ViewExplore the area around 20101 Winston Loop.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1978
Lot Size
5.61 acres
Living Area
3,973 sqft
Price/Sqft
$360
Parking
Garage

About this House

This single-family home is located at 20101 Winston Loop, Bend, OR. 20101 Winston Loop is in Bend, OR and in ZIP code 97703. This property has 5 bedrooms, 3 bathrooms and approximately 3,973 sqft of floor space. This property has a lot size of 5.61 acres and was built in 1978.
20101 Winston Loop, Bend, OR 97703 is a 5 bedroom, 3 bathroom, 3,973 sqft single-family home built in 1978. It last sold for $820,000 on May 11, 2017. It is currently off market. The Trulia Estimate is $1,432,200, with a rent estimate of $6,104/month.

Home Details for 20101 Winston Loop

Interior Features

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

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Deck
Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 5.61 acres

Price History for 20101 Winston Loop

DatePriceEventSource
05/11/2017$820,000Sold
N/A

Market trends in Bend

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$777K
$14.87KMoM
Sale-to-List Price
99.2%
0.4%MoM
Price per sq ft
$416
$4MoM
Available listings
1060
25MoM
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Property Tax and Assessment

Year2025
Tax$10,224
Assessment$1,344,430
Home facts updated by county records

Comparable Sales for 20101 Winston Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
64520 El Dorado Trl, Bend, OR
0.55
Single-Family Home
$925,000
11/10/25
3
3
2,541
64520 El Dorado Trl, Bend, OR
0.56
Single-Family Home
$925,000
11/10/25
3
3
2,541
65025 Wapiti Way, Bend, OR
0.60
Single-Family Home
$1,400,000
05/28/26
4
2
2,367
65057 Hopper Rd, Bend, OR
0.68
Single-Family Home
$1,275,000
03/10/26
4
5
4,011
65020 Swalley Rd, Bend, OR
0.60
Single-Family Home
$2,143,633
12/19/25
5
4
5,627
20087 Beaver Ln, Bend, OR
0.56
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
20087 Beaver Ln, Bend, OR
0.56
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
65070 Swalley Rd, Bend, OR
0.74
Single-Family Home
$2,143,633
12/19/25
5
4
4,601
20123 Elder Ln, Bend, OR
0.73
Single-Family Home
$1,125,000
07/27/26
4
3
2,092
64727 Hunnell Rd, Bend, OR
0.94
Single-Family Home
$1,010,000
05/15/26
3
2
1,851

Nearby homes

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Assigned Schools

These are the assigned schools for 20101 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 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
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  • 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
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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 "
    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
    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
    Flag
  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 20101 Winston Loop

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Off Market Homes Near 20101 Winston Loop

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Frequently asked questions about 20101 Winston Loop

  • What is 20101 Winston Loop estimated to be worth?
    Trulia's estimated value for 20101 Winston Loop in Bend, OR is $1,432,200.
  • What is the price history for 20101 Winston Loop?
    20101 Winston Loop in Bend, OR last sold for $820,000 in May 2017.
  • 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 $777K. That is up $14.87K from the prior month.
  • How big is the lot at 20101 Winston Loop?
    The lot at 20101 Winston Loop in Bend, OR is about 5.6 acres.
  • Does 20101 Winston Loop have a garage?
    Yes, 20101 Winston Loop in Bend, OR has a garage.