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.
Sold
From this home’s MLS record: the sale price, the closing date, the final asking price and the day it went on the market. The percentage is the sale price divided by the final asking price. Days on market count calendar days from going on the market to closing.
This 4-bed, 5-bath home at 375 Porter Creek Road in Winston sold for $680,000. It has 3,000 square feet, sits on 41.09 acres, was built in 1994, and is in N/A. It was on the market 71 days.
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Listing
Significant priced improvement! Discover the perfect blend of vineyard lifestyle and modern comfort in this recently updated 41-acre estate, nestled in the heart of Oregon's Umpqua Valley AVA. Surrounded by timber, a year-round creek, and a seasonal pond, this scenic retreat offers privacy, natural beauty, and endless potential. A spacious 3,000 sq ft home featuring four large bedrooms, large bonus room and three generous bathrooms--perfectly designed for relaxed living or hosting guests. Recent upgrades include newer metal roofs, HVAC systems, a cozy woodstove, and luxury vinyl plank flooring throughout, creating a warm and inviting environment.The estate also includes 8 acres of vineyard planted in 1995 with resistant rootstock Pinot Gris and Merlot. The vineyard is in need of attention (Mowing,suckering,spraying). A 1,600 sq ft former tasting room and boutique winery space offers charm and utility for ente
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 |
|---|---|---|
| Sep 24, 2026 | Sold | $680,000$95K down |
| Jul 13, 2026 | Listed | $775,000 |
| Year | Tax |
|---|---|
| 2025 | $2,589 |
Tax as filed on the listing. Douglas County. Parcel R65961.
Ask what this one closed at and why, or what it says about the house you own.
Listing courtesy of Triple Oaks 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.
