Outside our home market
Ryan Realty works Central Oregon. Our brokers live in Bend and cover the towns around it, from Redmond and Sisters to Sunriver and La Pine. Winston is outside that area. Our MLS feed is statewide, so this home and its price are live and current — what we cannot tell you is which street in Winston is the one to buy on.
A broker who works Winston every day will know it better than we do. Tell us what you need and we will introduce you to one we would use ourselves. No cost, no obligation.
This 3-bed, 3-bath home at 9114 Old Highway 99 S in Winston is listed at $735,000. It has 2,722 square feet, sits on 5.4 acres, was built in 1949, and is in N/A. Status is Active, with 151 days on market.
Overview
Interior
Exterior & lot
Systems & utilities
Financial
Listing
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.
A rough estimate, not a quote. Loan amount $588,000 · $147,000 down · 30 year term.
Insurance starts at 0.35% of price each year. Type your quote to replace it.
sold in the last 90 days
Every active and pending listing of every property type on the regional MLS through Oregon Data Share in Winston. The wash is sales density of closes in the last 90 days; homes for sale and pending stay as marks. Pulses and the sold count are the closes of the last 30 days. Counts and medians cover every listing read for this map.
| Date | Event | Price |
|---|---|---|
| Jun 6, 2026 | Price change | $735,000$50K down |
| May 17, 2026 | Listed | $785,000 |
| Year | Tax |
|---|---|
| 2025 | $5,002 |
Tax as filed on the listing. Douglas County. Parcel R42993.
What to do about this house
Tour requests usually get a same-day reply.
Listing courtesy of Umpqua Legacy Realty LLC
Data last updated October 15, 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.
