Active

Price cut: $50K (6/6)

$735,000

9114 Old Highway 99 S, Winston, OR 97496

3beds

3baths

2,722sqft

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Single Family Residence

Built in 1949

5.4 Acres Lot

$707,900 Zestimate^®

$270/sqft

$-- HOA

What's special

Escape to the peace and beauty of rural Oregon with this beautifully remodeled country retreat set on 5.4 usable acres of fenced pastureland. Offering the perfect blend of modern comfort and small-acreage functionality, this stunning single-level home features 2,722 sq. ft. with 3 bedrooms, 3 full baths, and a versatile flex space ideal for a home office or hobby room. Each bedroom includes its own walk-in closet, providing exceptional storage and comfort throughout the home. Thoughtfully updated throughout, the home combines spacious living with warm country charm, while expansive windows frame serene valley and mountain views from nearly every angle. The attached garage and one-level layout provide convenience and easy living. Outside, the property is ready for your hobby farm or equestrian lifestyle with a large barn complete with workspace, tack rooms, and 3 horse stalls, plus room to expand additional stalls or barn storage. Multiple fenced pastures and two chicken coops.

58 days

406

25

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Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 3

Heating

Heat Pump

Cooling

Heat Pump

Appliances

Included: Dishwasher, Microwave, Range, Refrigerator, Water Heater

Features

Flooring: Carpet, Laminate, Tile
Windows: Double Pane Windows, Vinyl Frames
Basement: None
Has fireplace: Yes
Fireplace features: Wood Burning
Common walls with other units/homes: No Common Walls

Interior area

Total structure area: 2,722
Total interior livable area: 2,722 sqft

Property

Parking

Total spaces: 2
Parking features: Asphalt, Driveway, Garage Door Opener, Storage
Garage spaces: 2
Has uncovered spaces: Yes

Accessibility

Accessibility features: Accessible Full Bath

Features

Levels: One
Stories: 1
Fencing: Fenced
Has view: Yes
View description: Mountain(s), Panoramic, Valley

Lot

Size: 5.4 Acres
Features: Level, Native Plants, Pasture, Sloped

Details

Additional structures: Animal Stall(s), Barn(s), Poultry Coop, RV/Boat Storage, Stable(s), Storage, Workshop
Additional parcels included: R43169 R43097
Parcel number: R42993
Zoning description: FF
Special conditions: Standard
Horses can be raised: Yes

Construction

Type & style

Home type: SingleFamily
Architectural style: Ranch
Property subtype: Single Family Residence

Materials

Concrete, Frame
Foundation: Concrete Perimeter
Roof: Composition

Condition

New construction: No
Year built: 1949

Utilities & green energy

Sewer: Septic Tank
Water: Public

Community & HOA

Community

Security: Smoke Detector(s)

HOA

Has HOA: No

Location

Region: Winston

Financial & listing details

Price per square foot: $270/sqft
Tax assessed value: $675,865
Annual tax amount: $5,002
Date on market: 5/17/2026
Cumulative days on market: 58 days
Listing terms: Cash,Conventional,VA Loan
Road surface type: Paved

Estimated market value

$707,900

$673,000 - $743,000

$2,760/mo

Price history

Date	Event	Price
6/6/2026	Price change	$735,000-6.4%$270/sqft
Source: RMLS (OR) #177934538 Report a problem
5/17/2026	Listed for sale	$785,000+201.9%$288/sqft
Source: Oregon Datashare #220221549 Report a problem
1/9/2007	Sold	$260,000$96/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$4,910 +2.9%	$397,710 +3%
2024	$4,774 +2.9%	$386,127 +3%
2023	$4,640 +3.1%	$374,881 +3%
2022	$4,501 +2.7%	$363,963 +3%
2021	$4,383 +3%	$353,363 +3%
2020	$4,257 +2.2%	$343,071 +3%
2019	$4,164 +2.7%	$333,079 +3%
2018	$4,055	$323,378 +3%
2017	$4,055 +5.3%	$313,960 +3%
2016	$3,850	$304,816 +3%
2015	$3,850 +4.5%	$295,938 +3%
2014	$3,686	$287,319 +3%
2013	$3,686 +8%	$278,951 +3%
2012	$3,411 +2.1%	$270,827 +3%
2011	$3,341 +2.8%	$262,939 +3%
2010	$3,252 +4.2%	$255,281 +3%
2009	$3,122 +3.2%	$247,846 +3%
2008	$3,025 +42.8%	$240,628 +41.8%
2007	$2,119 +2.5%	$169,668 +3%
2006	$2,067 +3.1%	$164,727 +3%
2005	$2,005 +4.4%	$159,930 +6.1%
2003	$1,921 +2.8%	$150,750 +3%
2002	$1,868	$146,360

Find assessor info on the county website

Monthly payment

Est. payment

Payment breakdown

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Principal & interest
$1,547
Mortgage insurance
$0
Property taxes
$170
Home insurance
$105
HOA fees
$0
Utilities
Not included

All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

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Climate risks

Neighborhood: 97496

Getting around

21 / 100

Car-Dependent

28 / 100

Somewhat Bikeable

Nearby schools

GreatSchools rating

7/10
Mcgovern Elementary School
Grades: 3-5Distance: 1.2 mi
4/10
Winston Middle School
Grades: 6-8Distance: 1 mi
5/10
Douglas High School
Grades: 9-12Distance: 1 mi

Schools provided by the listing agent

Elementary: McGovern Elem
Middle: Winston Middle
High: Douglas High

Source: Oregon Datashare. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.