20160 Winston Ct, Bend, OR 97703
OFF MARKET

20160 Winston Ct
Bend, OR 97703

  • 4 Beds
  • 4 Baths
  • 2,830 sqft (on 6.20 acres)

$1,608,700

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $8,982/mo*
Refinance Your Home

$1,608,700

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $8,982/mo*
Refinance Your Home
4 Beds
4 Baths
2,830 sqft
(on 6.20 acres)

Local Information

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

Description

Dramatic setting with spectacular views of Mt. Bachelor to Mt. Jefferson. Private and secluded, Winston Ranch setting. One level home with huge deck that overlooks the valley and to the mountains. The home has been exceptionally well maintained and is extremely comfortable. The pasture and barn will lend itself to horses or cattle. The landscaping is easy to maintain but very appropriate. This home is a must see. Irrigated 2.86 underground system.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 20160 Winston Ct

Interior Features

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

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Deck
Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 6.20 acres

Price History for 20160 Winston Ct

DatePriceEventSource
04/19/2021$1,360,000Sold
N/A
11/18/2011$625,000Sold
N/A
08/03/2011$683,000PriceChange
Agent Provided
05/21/2011$694,000PriceChange
Agent Provided
04/07/2011$744,000PriceChange
Agent Provided
09/10/2010$785,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$10,337
Assessment$1,501,480
Home facts updated by county records

Comparable Sales for 20160 Winston Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20110 Winston Loop, Bend, OR
0.31
Single-Family Home
$2,137,000
06/30/25
4
4
4,122
64520 El Dorado Trl, Bend, OR
0.49
Single-Family Home
$925,000
11/10/25
3
3
2,541
64520 El Dorado Trl, Bend, OR
0.49
Single-Family Home
$925,000
11/10/25
3
3
2,541
64810 Bill Martin Rd, Bend, OR
1.01
Single-Family Home
$1,375,000
11/07/25
4
3
3,204
64810 Bill Martin Rd, Bend, OR
1.01
Single-Family Home
$1,375,000
11/07/25
4
3
3,204
20019 Beaver Ln, Bend, OR
0.47
Single-Family Home
$1,162,000
07/21/25
3
3
3,934
65057 Hopper Rd, Bend, OR
0.76
Single-Family Home
$1,275,000
03/10/26
4
5
4,011
20087 Beaver Ln, Bend, OR
0.59
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
20087 Beaver Ln, Bend, OR
0.59
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
65010 Gerking Market Rd, Bend, OR
1.14
Single-Family Home
$1,200,000
01/09/26
3
4
2,416

Nearby homes

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Assigned Schools

These are the assigned schools for 20160 Winston Ct.
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."
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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
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  • 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
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  • 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
  • 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
    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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20160 Winston Ct, Bend, OR 97703 is a 4 bedroom, 5 bathroom, 2,830 sqft single-family home built in 1992. This property is not currently available for sale. 20160 Winston Ct was last sold on Apr 19, 2021 for $1,360,000. The current Trulia Estimate for 20160 Winston Ct is $1,608,700.