20150 Winston Loop, Bend, OR 97703
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OFF MARKET

20150 Winston Loop
Bend, OR 97703

  • 4 Beds
  • 4 Baths
  • 4,253 sqft (on 5.13 acres)

$1,957,000

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $10,942/mo*
Refinance Your Home

$1,957,000

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $10,942/mo*
Refinance Your Home
4 Beds
4 Baths
4,253 sqft
(on 5.13 acres)

Home Value

Trulia Estimate
$1.96M
Since last month
Decreased$86K (-4.3%)
Since last year
Decreased$88K (-4.4%)
Since last sale
Increased$663K (+53.9%)
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 decreased by -4% in the last 10 years
MonthEstimated value
2026
August 2026$1.89M
July 2026$1.91M
June 2026$1.98M
May 2026$2.01M
April 2026$1.98M
March 2026$1.92M
February 2026$1.91M
January 2026$1.83M
2025

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
0.54
Single-Family Home
$925,000
11/10/25
3
3
2,541
65057 Hopper Rd, Bend, OR
0.70
Single-Family Home
$1,275,000
03/10/26
4
5
4,011
65025 Wapiti Way, Bend, OR
0.65
Single-Family Home
$1,400,000
05/28/26
4
2
2,367
20087 Beaver Ln, Bend, OR
0.53
Single-Family Home
$1,150,000
01/09/26
3
3
2,525
65020 Swalley Rd, Bend, OR
0.72
Single-Family Home
$2,143,633
12/19/25
5
4
5,627
65010 Gerking Market Rd, Bend, OR
1.13
Single-Family Home
$1,200,000
01/09/26
3
4
2,416
64810 Bill Martin Rd, Bend, OR
1.03
Single-Family Home
$1,375,000
11/07/25
4
3
3,204

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
20160 Winston Ct, Bend, OR 97703
0.07
$1,408,900
3
5
3,694
Off Market
20180 Winston Loop, Bend, OR 97703
0.16
$2,850,000
5
4
5,528
For Sale
20110 Winston Loop, Bend, OR 97703
0.25
$2,151,600
4
4
4,122
Off Market
20124 Tumalo Rd, Bend, OR 97703
0.24
$1,619,800
3
3
3,768
Off Market
20040 Tumalo Rd, Bend, OR 97703
0.23
$4,603,300
6
6
7,004
Off Market
20036 Tumalo Rd, Bend, OR 97702
0.23
$2,251,800
4
4
3,589
Off Market
20038 Tumalo Rd, Bend, OR 97703
0.26
$2,141,300
6
4
3,924
Off Market
20100 Winston Loop, Bend, OR 97703
0.31
$1,091,500
3
3
2,036
Off Market
64635 Simon Rd, Bend, OR 97703
0.32
$1,641,700
4
3
2,909
Off Market
19975 Tumalo Rd, Bend, OR 97703
0.31
-
-
-
-
Off Market
20001 Beaver Ln, Bend, OR 97701
0.39
$451,200
3
2
1,440
Off Market

Local Information

  • Map ViewExplore the area around 20150 Winston Loop.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
5.13 acres
Living Area
4,253 sqft
Price/Sqft
$460
Parking
3 Car Garage
HOA
$117/Monthly

About this House

Gorgeous, single level home, is nestled in the middle of a 5.13 acre lot with 1.5 acres of irrigation. This home offers expansive mountain and pastoral views from every room. With 4 bedrooms, 4 full bathrooms, this 4253 sqft home has gorgeous beamed ceilings, a wall of windows for viewing the mountains, meticulously maintained grounds, all new SS appliances, new carpet throughout, and automatic blinds. This home has a huge kitchen, form
20150 Winston Loop, Bend, OR 97703 is a 4 bedroom, 4 bathroom, 4,253 sqft single-family home built in 1997. It last sold for $1,230,000 on Oct 4, 2019 (4% below the $1,285,000 asking price). It is currently off market. The Trulia Estimate is $1,957,000, with a rent estimate of $7,238/month.
Last check for updates: about 8 hours ago
Listed by Christie Glennon Pinnick, (541) 788-1047
Christie Glennon Realty
Bought with: Christie Glennon Pinnick, (541) 788-1047, Christie Glennon Realty
Source: RMLS (OR), MLS#19474406

Home Details for 20150 Winston Loop

Active Status

MLS Status: Sold

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4Number of Bathrooms (main level): 4
Dimensions and Layout
Living Area: 4253 Square Feet
Appliances & Utilities
Appliances: Built-In Range, Built-In Refrigerator, Dishwasher, Disposal, Gas Appliances, Microwave, Stainless Steel Appliance(s), Electric Water Heater, Propane Water HeaterDishwasherDisposalLaundry: Laundry RoomMicrowave
Heating & Cooling
Heating: Radiant,ZonedNo CoolingHas HeatingHeating Fuel: Radiant
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Gas, PropaneHas a Fireplace
Gas & Electric
Gas: Propane
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
View
Has a ViewView: Mountain(s)
Security
Security: Fire Sprinkler System

Exterior Features

Exterior Home Features
Roof: CompositionPatio / Porch: Deck, PatioFencing: FencedOther Structures: RVHookup, WorkshopExterior: RV HookupFoundation: Stem Wall
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,RV Access/Parking,Attached
Frontage
Road Frontage: Private Road
Water & Sewer
Sewer: Septic Tank
Farm & Range
Acres Incl in Water Rights: 1.5Includes Irrigation Water Rights

Days on Market

Cumulative Days on Market: 85

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Vinyl Siding, Wood SidingNot a New ConstructionNot Attached Property
Property Information
Condition: ResaleParcel Number: 154882

Price & Status

Price
List Price: $1,285,000
Status Change & Dates
Off Market Date: Tue Sep 10 2019

Location

Direction & Address
City: Bend
School Information
Elementary School: Lava RidgeJr High / Middle School: Sky ViewHigh School: Mountain View

Building

Building Area
Building Area: 4253 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $1,400/Annually

Lot Information

Lot Area: 5.13 Acres

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 19474406

Additional Information

HOA Amenities: Road Maintenance

Price and Tax history

DateEventPrice
Oct 4, 2019
Source: RMLS (OR) #19474406
Sold
$1,230,000

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
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Around this home

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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!"
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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
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  • 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
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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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
  • 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
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  • 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
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  • 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 20150 Winston Loop

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Off Market Homes Near 20150 Winston Loop

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Frequently asked questions about 20150 Winston Loop

  • What is 20150 Winston Loop estimated to be worth?
    Trulia's estimated value for 20150 Winston Loop in Bend, OR is $1,957,000.
  • What is the price history for 20150 Winston Loop?
    20150 Winston Loop in Bend, OR last sold for $1,230,000 in October 2019.
  • 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 20150 Winston Loop have laundry facilities?
    Yes, 20150 Winston Loop in Bend, OR has laundry facilities.
  • Does 20150 Winston Loop have a yard?
    Yes, 20150 Winston Loop in Bend, OR has a yard.
The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS™ of Portland, Oregon. Real estate listings held by brokerage firms other than Zillow, Inc. are marked with the RMLS™ logo, and detailed information about these properties includes the names of the listing brokers. Listing content is copyright © 2026 RMLS™, Portland, Oregon. This content last updated on 2026-08-12 15:52:12 PDT. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified.