Best Real Estate Agents in Winchester, OR• Updated
Looking for the best real estate agent in Winchester, OR? This page compares realtors in Winchester within each home type and price range using actual transaction data — not reviews or paid ads. Whether you want a listing agent in Winchester, OR or help buying a home in Winchester, our 2026 scores use verified sales records, days on market, and sale-to-list ratios.
Market Pulse: Hot 🔥
The Winchester, OR real estate market is currently a Seller's Market. Homes are selling at 99% of list price on average (Sale Price to List Price Ratio). With 1 active listings and 6 closed sales in the latest month, inventory remains at 0.5 months of supply. Trends over the last half-year show median values moving down by 11%, while Average Days on Market has decreased by 22%. Listings in Winchester are moving 15 days faster than the Douglas County average.
Top Listing & Buyer's Agents in Winchester, OR
Source: third-party closed MLS records, data as of Oct 2026. Agents are compared within each home type and price range. How we score agents →
Detached Homes
Mid-Market Detached Home Market Trends Median Price Market Trend The Mid-Market Detached Home tier had a median sale price of $517K over the last 6 months. Days On Market Avg. Market Trend Lower is better Detached Homes in the Mid-Market range averaged 64 days on market over the last 6 months. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Mid-Market Detached Homes received 98% of list price on average over the last 6 months.
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High-End Detached Home Market Trends Median Price Market Trend The High-End Detached Home tier had a median sale price of $740K over the last 6 months. Days On Market Avg. Market Trend Lower is better Detached Homes in the High-End range averaged 52 days on market over the last 6 months. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of High-End Detached Homes received 98% of list price on average over the last 6 months.
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Winchester Real Estate Market Trends October 2026
Inventory Breakdown by Segment
| Property Type | Entry Level | High-End | Mid-Market | Total |
|---|---|---|---|---|
| Detached Home | — | — | 1 | 1 |
Market Insights & FAQ
How is the real estate market in Winchester, OR performing right now?
The data indicates a high-intensity seller's market in Winchester, OR. Inventory is at 0.5 months of supply. Inventory is critically low, meaning well-priced homes move rapidly, often with multiple offers.
What are the current pricing trends for Winchester, OR real estate?
Currently, $516,000 represents the median entry point in Winchester, OR. Over the past half-year, home values in Winchester have moved downward by approximately 11% based on regional transaction data.
Are sellers in Winchester, OR getting their full asking price?
Sellers hold the edge, though homes are closing slightly below asking in Winchester, OR, with a Sale Price to List Price Ratio of 98.5%. On average, properties in Winchester are transitioning from active to sold status in 50 days.
Which listing agents does Agent Algo feature in Winchester, OR?
Agent Algo compares agents within the same home type and price range, so Winchester, OR has no single overall winner. Featured listing agents include Deleta Dickson (Mid-Market Detached Homes, 2 closed listings), Carol Thompson (High-End Detached Homes, 1 closed listing), Bob Lamonte (Entry Level Detached Homes, 1 closed listing). Scores are built from closed sales outcomes — not reviews or paid placements.
How does the Winchester, OR market compare to Douglas County trends?
Winchester, OR maintains a distinct profile within the broader Douglas County region. Median home values are currently 65% higher than the regional average, reflecting the unique demand and inventory dynamics of Winchester.
Which listing agents are active in Mid-Market Detached Homes in Winchester, OR?
Deleta Dickson has recent Mid-Market Detached Home listings in Winchester, OR, at an above-average sale-to-list ratio for the segment. With only a few closings in this segment, treat this as an early signal rather than a ranking. Based on 2 closed listings in this segment.
Which buyer's agents are active in Mid-Market Detached Homes in Winchester, OR?
Shawn Mogenson has recent Mid-Market Detached Home purchases in Winchester, OR. With only a few closings in this segment, treat this as an early signal rather than a ranking. Based on 2 closed purchases in this segment.
Which buyer's agents are active in High-End Detached Homes in Winchester, OR?
Chris Woodruff has recent High-End Detached Home purchases in Winchester, OR, closing faster than the segment average at a below-average sale-to-list ratio. With only a few closings in this segment, treat this as an early signal rather than a ranking. Based on 1 closed purchase in this segment.
Which listing agents are active in High-End Detached Homes in Winchester, OR?
Carol Thompson has recent High-End Detached Home listings in Winchester, OR, closing faster than the segment average at an above-average sale-to-list ratio. With only a few closings in this segment, treat this as an early signal rather than a ranking. Based on 1 closed listing in this segment.
Which listing agents are active in Entry Level Detached Homes in Winchester, OR?
Bob Lamonte has recent Entry Level Detached Home listings in Winchester, OR. With only a few closings in this segment, treat this as an early signal rather than a ranking. Based on 1 closed listing in this segment.
Which buyer's agents are active in Entry Level Detached Homes in Winchester, OR?
Jeremiah Perry has recent Entry Level Detached Home purchases in Winchester, OR. With only a few closings in this segment, treat this as an early signal rather than a ranking. Based on 1 closed purchase in this segment.