5265 Upper Olalla Road

Sold 3/28/19
Sold 3/28/19
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Sold
Last Sold Price
$300,000
3 beds1,520 sqft
5265 Upper Olalla Rd, Winston, OR 97496
Single FamilyProperty Type
2.52 acresLot Size
1976Year Built
$197/sq ftPrice per sq ft
4 carsParking Spaces

Description

Beautiful private setting nestled in the country. Ben Irving 5 mins away for recreation. All year round creek with irrigation rights. Ranch style one level home with extended 4 car garage. Updates including kitchen, windows and main bathroom. Large shop and RV covered storage. Large area for gardening that has water irrigation.Beautiful private setting nestled in the country. Ben Irving 5 mins away for recreation. All year round creek with irrigation rights. Ranch style one level home with extended 4 car garage. Updates including kitchen, windows and main bathroom. Large shop and RV covered storage. Large area for gardening that has water irrigation.
Listing closed: 03/28/2019 12:00 AM • Source: RMLS, MLS#: 18297900

Recent comparable sales

Median sold price

$300,000

Avg days on market

80

Sale-to-list ratio

94.6%

Winston, OR

9 comparable properties found

$445,000 | 7950 Upper Olalla Road, Winston, OR 97496
1/49
1

$445,000

Sold 05/30/25

3
Bedrooms
1,393
Square Feet
3.33
Acres

7950 Upper Olalla Road, Winston, OR 97496

a view of an outdoor space
1/40
2

$249,900

Sold 06/11/26

3
Bedrooms
1,440
Square Feet
4.57
Acres

2409 Ireland Road, Winston, OR 97496

$304,000 | 311 Northwest Morgan Avenue, Winston, OR 97496
1/42
3

$304,000

Sold 10/18/24

3
Bedrooms
1,410
Square Feet
0.25
Acres

311 Northwest Morgan Avenue, Winston, OR 97496

front view of house with a yard
4

$285,000

Sold 02/07/25

3
Bedrooms
1,600
Square Feet
1.37
Acres

4910 Tahoe Court, Winston, GA 30187

$320,000 | 401 Southeast Sunnyside Drive, Winston, OR 97496
1/41
5

$320,000

Sold 07/03/25

3
Bedrooms
1,374
Square Feet
0.14
Acres

401 Southeast Sunnyside Drive, Winston, OR 97496

a front view of a house with a yard
6

$285,000

Sold 05/13/25

3
Bedrooms
1,557
Square Feet
0.62
Acres

7244 Valley Drive, Winston, GA 30187

a view of outdoor space and yard
1/48
7

$300,000

Sold 03/25/26

3
Bedrooms
1,374
Square Feet
0.39
Acres

231 Northeast Darrell Avenue, Winston, OR 97496

a front view of a house with a yard
8

$300,000

Sold 07/07/25

3
Bedrooms
1,439
Square Feet
0.99
Acres

4958 Alpine Court, Winston, GA 30187

$315,000 | 120 Southeast Edwards Street, Winston, OR 97496
1/20
9

$315,000

Sold 02/27/26

3
Bedrooms
1,421
Square Feet
0.12
Acres

120 Southeast Edwards Street, Winston, OR 97496

Amenities

  • Garage
  • Parking Included
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Location

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Sold By Blue Wave Real Estate

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Property Information for 5265 Upper Olalla Road

Property Details
  • Taxes: $1,766 / year
  • MLS Type: Residential / Single Family Residence
  • County: Douglas County
Building Information
  • Stories: 1
  • Year Built: 1976
  • Lot Size: 2.52 AC / 109,771 SF
Summary
Location and General Information
  • Accessibility Features: One Level, Minimal Steps
  • Accessibility Y/N: Yes
  • Area: Douglas Co: Winston/southwest of Roseburg
  • Country: US
  • Directions: Hwy 42, Left on Upper Olalla to address on the Right.
  • Style: Daylight Ranch, 1 Story
Parking
  • Garage Or Parking Spaces: 4
  • Garage Type: Extra Deep, Tandem
  • Parking: Driveway
Taxes and HOA Information
  • CC and R Y/N: No
  • FIRPTA Y/N: No
  • HOA Y/N: No
  • Tax Deferral YN: No
Virtual Tour
  • Video Virtual Tour 1 Y/N: No
Property
Lot Information
  • Acres: 2.52
  • Lot Description: Level, Sloped
  • Senior Housing Y/N: No
  • Zoning: R5
  • SqFt Source: Western Ti
Property and Assessments
  • Warranty Available Y/N: No
  • Water Description: Other, Well
Utilities
  • Cooling Description: Heat Pump
  • Fuel Description: Electricity
  • Heating Description: Forced Air
  • Hot Water Description: Electricity
  • Sewer Description: Septic Tank
Interior and Exterior Features
Exterior Features
  • Exterior Description: Lap Siding
  • Exterior Features: Covered Courtyard, RV Parking, Workshop, Yard, RV/Boat Storage
  • Roof Type: Composition
  • RV Description: RV Parking, RV/Boat Storage
  • Water Front Y/N: Yes
  • Waterfront Description: Creek
Interior Features
  • Basement Foundation: Crawl Space, Concrete Perimeter
  • Fireplaces Total: 1
  • Interior Features: Ceiling Fan(s), Wall to Wall Carpet, Laminate Flooring
  • SqFt Calculated: 1520
  • SqFt Lower Level Total: 0
  • SqFt Main Level Total: 1520
  • SqFt Upper Level Total: 0
  • View Y/N: Yes
  • View: Valley
Master Bedroom
  • Primary Bedroom Level: Main
Bedroom 2
  • Bedroom 2 Level: Main
Bedroom 3
  • Bedroom 3 Level: Main
Dining Room
  • Dining Room Level: Main
Family Room
  • Family Room Level: Main
Kitchen
  • Kitchen Appliances: Dishwasher, Tile, Free-Standing Range, Free-Standing Refrigerator, Granite
  • Kitchen Room Level: Main
Living Room
  • Living Room Level: Main
Baths
  • Baths Lower Level Full: 0
  • Baths Lower Level Partial: 0
  • Baths Lower Level Total: 0.0
  • Baths Main Level Full: 2
  • BathsMainLevelPartial: 0
  • Baths Main Level Total: 2
  • Baths Partial: 0
  • Baths Upper Leve lFull: 0
  • Baths Upper Level Partial: 0
  • Baths Upper Level Total: 0
Farm
Farm Information
  • Farm Y/N: No

Property History for 5265 Upper Olalla Road

DateEvent & SourcePriceAppreciation
Mar 26, 2019

Sold (Public Record)

Public Record #641595398

$300,000—
DateEvent & SourcePrice
03/26/2019

Sold (Public Record)

Public Record #641595398

$300,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 5265 Upper Olalla Road

Taxable ValueLand-Additions-Total-
Tax Record2025$2,677 ($223 / month)
Home Facts
Beds3Total Finished SqFt1,520 SqFtAbove Grade Finished SqFt1,520 SqFtStories1Lot Size106,286 SqFtStyleMiscellaneous ResidentialYear Built1976Year Renovated2000ZoningFGCountyDOUGLASAPN29-07W-08-01600Fireplace TypeHas Fireplace

Schools near 5265 Upper Olalla Road

This home is within Winston-Dillard School District 116.
Rating
School
Type
Grades
Distance
Brockway Elementary School
Public - PK to 2
Winston Middle School
Public - 6 to 8
Douglas High School
Public - 9 to 12
Dillard Alternative High School
Public - 9 to 12
Rating
School
Distance
Brockway Elementary School
PublicPK to 2

Winston Middle School
Public6 to 8

Douglas High School
Public9 to 12

Dillard Alternative High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 5265 Upper Olalla Road, Winston, OR 97496
$300,000
3
1,520
109,771
179 Deer Haven Lane, Winston, OR 97496
–
–
–
–
217,800
5191 Upper Olalla Road, Winston, OR 97496
–
3
2
1,296
179,032
5241 Upper Olalla Road, Winston, OR 97496
$85,000
5
4
2,012
217,800
5350 Upper Olalla Road, Winston, OR 97496
–
–
1
924
211,702
5230 Upper Olalla Road, Winston, OR 97496
$210,000
3
1
941
360,241

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX Professional Realty

All information provided is deemed reliable but is not guaranteed and should be independently verified. 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 Compass are marked with the RMLS logo and detailed information about these properties includes the names of the listing brokers. Copyright © 2026 RMLS, Portland, Oregon. Last updated: 03/29/2019 10:55 AM