Best Real Estate Agents in Windsor, VA• Updated Oct 2026

The data indicates a high-intensity environment in Windsor, VA. Inventory is at 1.3 months, meaning a fast-paced market where inventory is limited. Inventory is critically low, meaning well-priced homes move rapidly often with multiple offers.

Currently, $328,000 represents the median entry point in Windsor, VA. Over the past half-year, home values in Windsor have moved downward by approximately 18% based on regional transaction data.

Buyers have room for negotiation in Windsor, VA, with a Sale Price to List Price Ratio of 97.8%. On average, properties in Windsor are transitioning from active to sold status in 90 days.

Based on closed transaction data, Lori Cutrell ranks at the top of our Windsor leaderboard — with 3 completed transactions on record earning an algorithm performance score of 35. 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.

Windsor, VA maintains a distinct profile within the broader Isle Of Wight region. Median home values are currently 14% lower than the regional average, reflecting the unique demand and inventory dynamics of Windsor.

If you're selling a High-End Detached Home in Windsor, VA, the data points to Lori Cutrell as a standout choice. Their listings in this segment consistently close faster than the local pace — a meaningful edge when carrying costs and market timing matter to sellers.

Our data flags Aaron Holmes as a top buyer's advocate for Entry Level Detached Home properties in Windsor, 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.

If you're hunting for a High-End Detached Home in Windsor, VA, Lori Cutrell's track record speaks for itself. For buyers competing in the High-End Detached Home market in Windsor, VA, their track record indicates speed and negotiating strength that outperforms the segment baseline on both counts.

T Dale Scott has been particularly active in Windsor's Entry Level Detached Home segment, and the numbers back it up. They've built a consistent track record in the Entry Level Detached Home category specifically — not just broad volume, but demonstrated results in this exact niche in Windsor, VA.

When looking specifically at Mid-Market Detached Home transactions, Alexis Wait consistently surfaces as a top performer in Windsor, VA. Alexis Wait's Mid-Market Detached Home transactions in Windsor, VA move more quickly from listing to close than what's typical for this segment, reducing the exposure and uncertainty sellers often face.

For those looking to purchase a Mid-Market Detached Home in Windsor, VA, Amy Willette has the deal history to support the choice. Buying effectively in this segment means knowing when and how hard to push. Their track record here shows they regularly outperform the local sale-to-list benchmark — in the buyer's favor.

Navigating Windsor's Ultra-Luxury Detached Home market as a buyer? Kelsey Derby is among the most effective agents in this niche. Their buyer closings in this segment show a sale-to-list ratio that's more favorable than the local average — a signal of effective negotiation that keeps final purchase prices competitive for buyers.

Shante Cross has helped buyers close on Mid-Market Mobile/Manufactured Home properties in Windsor, VA — and the data shows it. 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.