Best Real Estate Agents in Chesterfield, MA• Updated
Looking for the best real estate agent in Chesterfield, MA? This page ranks the top realtors in Chesterfield by actual transaction data — not reviews or paid ads. Whether you want to find a top listing agent in Chesterfield, MA or buy a home in Chesterfield, our 2026 rankings use verified sales records, days on market, and price retention to surface the highest-performing agents.
Market Pulse: Opportunity 📈
The Chesterfield, MA real estate market is currently a Buyer's Market. Homes are retaining 86% of their value (Sale Price to List Price Ratio). With 3 active listings and 1 closed sales this month, inventory remains at 9 months of supply. Trends over the last half-year show median values moving down by 8%, while Average Days on Market has increased by 46%. Transaction speed in Chesterfield is currently 26 days slower than the broader Hampshire benchmark.
Top Listing & Buyer's Agents in Chesterfield, MA
Chesterfield Real Estate Market Trends September 2026
Inventory Breakdown by Segment
| Property Type | High-End | Mid-Market | Total |
|---|---|---|---|
| Detached Home | 1 | 1 | 3 |
Market Insights & FAQ
How is the real estate market in Chesterfield, MA performing right now?
The data indicates a stable environment in Chesterfield, MA. Inventory is at 9 months, meaning a balanced environment with steady turnover. Inventory levels provide a healthy range of options for prospective buyers.
What are the current pricing trends for Chesterfield, MA real estate?
Currently, $300,000 represents the median entry point in Chesterfield, MA. Over the past half-year, home values in Chesterfield have moved downward by approximately 8% based on regional transaction data.
Are sellers in Chesterfield, MA getting their full asking price?
Buyers have room for negotiation in Chesterfield, MA, with a Sale Price to List Price Ratio of 85.7%. On average, properties in Chesterfield are transitioning from active to sold status in 86 days.
Who is the best agent to sell my home in Chesterfield?
Based on closed transaction data, David Murphy ranks at the top of our Chesterfield leaderboard earning an algorithm performance score of -17. 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.
How does the Chesterfield, MA market compare to Hampshire trends?
Chesterfield, MA maintains a distinct profile within the broader Hampshire region. Median home values are currently 40% lower than the regional average, reflecting the unique demand and inventory dynamics of Chesterfield.
Who is a top listing agent for High-End Detached Home homes in Chesterfield, MA?
If you're selling a High-End Detached Home in Chesterfield, MA, the data points to David Murphy as a standout choice. They've built a consistent track record in the High-End Detached Home category specifically — not just broad volume, but demonstrated results in this exact niche in Chesterfield, MA.
Which agent is best for buying a Mid-Market Detached Home in Chesterfield, MA?
Our data flags Ann Jerebtsov as a top buyer's advocate for Mid-Market Detached Home properties in Chesterfield, MA. Across their deals in the Mid-Market Detached Home category, Ann Jerebtsov has consistently achieved better-than-average terms relative to asking price in Chesterfield, MA. That kind of negotiating edge compounds over a transaction.
Who is a top listing agent for Mid-Market Detached Home homes in Chesterfield, MA?
Among agents with recent closings in the Mid-Market Detached Home space, Linda Webster has the strongest performance metrics in Chesterfield, MA. Speed and price retention together are the hardest combination to find in a single agent. Their track record in the Mid-Market Detached Home category in Chesterfield, MA reflects both.
Which agent is best for buying a High-End Detached Home in Chesterfield, MA?
Among agents actively helping buyers in the High-End Detached Home space, Donald Mailloux stands out in Chesterfield, MA. Their buyer transactions in the High-End Detached Home category in Chesterfield, MA reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.