Best Real Estate Agents in Windsor, MA• Updated
Looking for the best real estate agent in Windsor, MA? This page ranks the top realtors in Windsor by actual transaction data — not reviews or paid ads. Whether you want to find a top listing agent in Windsor, MA or buy a home in Windsor, our 2026 rankings use verified sales records, days on market, and price retention to surface the highest-performing agents.
Market Pulse: Opportunity 📈
The Windsor, MA real estate market is currently a Buyer's Market. Homes are retaining 98% of their value (Sale Price to List Price Ratio). With 4 active listings and 3 closed sales this month, inventory remains at 24 months of supply. Trends over the last half-year show median values moving up by 400%, while Average Days on Market has increased by 18%. Transaction speed in Windsor is currently 3 days slower than the broader Berkshire benchmark.
Top Listing & Buyer's Agents in Windsor, MA
Detached Homes
Entry Level Detached Home Market Trends Median Price Market Trend The Entry Level Detached Home tier commands a price of $75K. Days On Market Avg. Market Trend Lower is better Detached Home homes in the Entry Level range average 54 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Entry Level Detached Home assets receive 79% of list price.
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Mid-Market Detached Home Market Trends Median Price Market Trend The Mid-Market Detached Home tier commands a price of $375K. Days On Market Avg. Market Trend Lower is better Detached Home homes in the Mid-Market range average 72 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Mid-Market Detached Home assets receive 98% of list price.
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Windsor Real Estate Market Trends September 2026
Inventory Breakdown by Segment
| Property Type | Entry Level | High-End | Mid-Market | Total |
|---|---|---|---|---|
| Detached Home | — | 2 | 2 | 4 |
Market Insights & FAQ
How is the real estate market in Windsor, MA performing right now?
The data indicates a stable environment in Windsor, MA. Inventory is at 24 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 Windsor, MA real estate?
Currently, $375,000 represents the median entry point in Windsor, MA. Over the past half-year, home values in Windsor have moved upward by approximately 400% based on regional transaction data.
Are sellers in Windsor, MA getting their full asking price?
Buyers have room for negotiation in Windsor, MA, with a Sale Price to List Price Ratio of 97.7%. On average, properties in Windsor are transitioning from active to sold status in 72 days.
Who is the best agent to sell my home in Windsor?
Based on closed transaction data, Jessica Rizzo ranks at the top of our Windsor leaderboard earning an algorithm performance score of -39. 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 Windsor, MA market compare to Berkshire trends?
Windsor, MA maintains a distinct profile within the broader Berkshire region. Median home values are currently 30% lower than the regional average, reflecting the unique demand and inventory dynamics of Windsor.
Which agent is best for buying a Entry Level Detached Home in Windsor, MA?
Buyers targeting Entry Level Detached Home homes in Windsor, MA may want to work with Lisa Carroll. Their buyer transactions in the Entry Level Detached Home category in Windsor, MA reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.
Which agent is best for buying a Mid-Market Detached Home in Windsor, MA?
Our data flags Brenda Durant as a top buyer's advocate for Mid-Market Detached Home properties in Windsor, MA. 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.
Who is a top listing agent for Mid-Market Detached Home homes in Windsor, MA?
Among agents with recent closings in the Mid-Market Detached Home space, Jessica Rizzo has the strongest performance metrics in Windsor, 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 Windsor, MA reflects both.
Who is a top listing agent for High-End Detached Home homes in Windsor, MA?
Jesse Dimitropolis has been particularly active in Windsor's High-End Detached Home segment, and the numbers back it up. Their listings in this segment consistently close faster than the local pace — a meaningful edge when carrying costs and market timing matter to sellers.
Which agent is best for buying a High-End Detached Home in Windsor, MA?
Laiken Rapisarda has a strong showing as a buyer's agent in Windsor's High-End 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.
Who is a top listing agent for Entry Level Detached Home homes in Windsor, MA?
Sellers of Entry Level Detached Home homes in Windsor, MA have found a reliable partner in Lisa Carroll, based on closed deal data. Real estate is hyper-local. Lisa Carroll's repeated activity in Windsor's Entry Level Detached Home niche demonstrates the kind of specific, proven familiarity that matters when the stakes are high.