Best Real Estate Agents in Upperville, VA• Updated Jul 2026

The data indicates a stable environment in Upperville, VA. Inventory is at 18 months, meaning a balanced environment with steady turnover. Inventory levels provide a healthy range of options for prospective buyers.

Currently, $1,875,000 represents the median entry point in Upperville, VA. Over the past half-year, home values in Upperville have moved downward by approximately 82% based on regional transaction data.

Sellers hold significant leverage in Upperville, VA, with a Sale Price to List Price Ratio of 104.5%. On average, properties in Upperville are transitioning from active to sold status in 34 days.

Based on closed transaction data, Cricket Bedford ranks at the top of our Upperville leaderboard — with 2 completed transactions on record earning an algorithm performance score of -22. Agent Algo's rankings are built entirely from real deal outcomes — not reviews or paid placements — so this reflects actual results in the local market.

Upperville, VA maintains a distinct profile within the broader Fauquier region. Median home values are currently 105% higher than the regional average, reflecting the unique demand and inventory dynamics of Upperville.

If you're selling a Entry Level Detached Home in Upperville, VA, the data points to Cricket Bedford as a standout choice. Their listings in this segment have consistently closed faster than the local average while achieving above-average sale-to-list ratios — a rare combination that directly benefits sellers on both time and final price.

Our data flags R Clarke as a top buyer's advocate for Entry Level Detached Home properties in Upperville, VA. The data shows a consistent pattern across their deals here: shorter time to close than the segment average, and acquisition terms that tend to land below-average relative to list price. Two things buyers care about most.

Among agents with recent closings in the Mid-Market Detached Home space, Cricket Bedford has the strongest performance metrics in Upperville, VA. Real estate is hyper-local. Cricket Bedford's repeated activity in Upperville's Mid-Market Detached Home niche demonstrates the kind of specific, proven familiarity that matters when the stakes are high.

Among agents actively helping buyers in the High-End Detached Home space, Carolyn Young stands out in Upperville, VA. Their buyer transactions in the High-End Detached Home category in Upperville, VA reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.

Sam Fisher has a strong showing as a buyer's agent in Upperville's Ultra-Luxury Detached Home market. The data shows a consistent pattern across their deals here: shorter time to close than the segment average, and acquisition terms that tend to land below-average relative to list price. Two things buyers care about most.

Sellers of Ultra-Luxury Detached Home homes in Upperville, VA have found a reliable partner in Daniel Heider, based on closed deal data. In a category where leaving money on the table is easy, their sale-to-list performance in this segment stands above the local benchmark — reflecting an ability to negotiate and price effectively.

Navigating Upperville's Mid-Market Detached Home market as a buyer? Will Driskill is among the most effective agents in this niche. Their buyer transactions in the Mid-Market Detached Home category in Upperville, VA reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.

Kathryn Harrell specializes in High-End Detached Home properties and has built a measurable edge in Upperville's market. Our algorithm ranks them based on closed transaction outcomes in the High-End Detached Home segment, not self-reported volume or marketing activity. The ranking reflects actual local performance.