Best Real Estate Agents in Holliston, MA• Updated Sep 2026

The data indicates a high-intensity environment in Holliston, MA. Inventory is at 1.5 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, $834,000 represents the median entry point in Holliston, MA. Over the past half-year, home values in Holliston have moved downward by approximately 0% based on regional transaction data.

Sellers hold significant leverage in Holliston, MA, with a Sale Price to List Price Ratio of 101.4%. On average, properties in Holliston are transitioning from active to sold status in 52 days.

Based on closed transaction data, Kathy Chisholm ranks at the top of our Holliston leaderboard — with 9 completed transactions on record earning an algorithm performance score of 85. 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.

Holliston, MA maintains a distinct profile within the broader Middlesex region. Median home values are currently 23% lower than the regional average, reflecting the unique demand and inventory dynamics of Holliston.

If you're selling a Mid-Market Detached Home in Holliston, MA, the data points to Kathy Chisholm 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 transaction-level analysis puts Michael Yerardi at the top for Mid-Market Townhome listings in Holliston, MA. The data points to a dual edge here: shorter time on market than is typical for this segment, and sale prices that hold closer to — or above — the asking price compared to local norms.

Among agents with recent closings in the High-End Detached Home space, Kathy Chisholm has the strongest performance metrics in Holliston, MA. Speed and price retention together are the hardest combination to find in a single agent. Their track record in the High-End Detached Home category in Holliston, MA reflects both.

Among agents actively helping buyers in the Mid-Market Townhome space, Ginger Reilly stands out in Holliston, MA. 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.

Donald Simon has a strong showing as a buyer's agent in Holliston's Mid-Market Detached Home market. Across their deals in the Mid-Market Detached Home category, Donald Simon has consistently achieved better-than-average terms relative to asking price in Holliston, MA. That kind of negotiating edge compounds over a transaction.

Sellers of Ultra-Luxury Detached Home homes in Holliston, MA have found a reliable partner in Tara DAmato, based on closed deal data. Speed and price retention together are the hardest combination to find in a single agent. Their track record in the Ultra-Luxury Detached Home category in Holliston, MA reflects both.

Navigating Holliston's High-End Detached Home market as a buyer? Chris Dudzic is among the most effective agents in this niche. Their buyer transactions in this segment close faster than the local norm and at sale-to-list ratios that are more favorable than typical — meaning they move quickly and negotiate effectively for the buyers they represent.

Jeanne Murphy specializes in Entry Level Detached Home properties and has built a measurable edge in Holliston's market. The data points to a dual edge here: shorter time on market than is typical for this segment, and sale prices that hold closer to — or above — the asking price compared to local norms.