$735,000
9114 Old Highway 99
Winston, OR 97496
Down $50,000 from original list price $785,000.
Active39 days on market$270/sqft
About this home
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.
Listing courtesy of Umpqua Legacy Realty LLC, agent Kristina Scott
Data last updated June 26, 2026
Based on information from Oregon Data Share. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listing information is for consumers personal, non-commercial use only.
A rough estimate, not a quote. A real number comes from a lender.
Loan amount $588,000 · $147,000 down · 30 year term
Monthly cash flow, cap rate, and cash-on-cash return at this price. Every number is an estimate you can adjust to your own financing and rent.
Estimate $3,675 ($3,125–$4,225) · starting estimate. Edit to your own number.
At $735,000 with 20% down, this property runs $1,616 per month negative. Adjust the price, down payment, or rent to find what works.
Estimates only, not investment advice or a guarantee of rent, value, or return. Figures depend on the numbers you enter and current market conditions. Verify with your lender, tax advisor, and a Ryan Realty broker before you rely on them.
We pull climate risk data from FEMA flood maps, the Deschutes County wildland-urban interface map, and NOAA heat trends. Detailed scoring for this property is on request.
Get the climate reportWe compute vacation rental projections from comparable short-term rentals in the same community, weighted by bed count, view, and amenities. A custom projection for this property is on request.
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