Best Real Estate Agents in Chestnut Hill, MA• Updated Sep 2026

The data indicates a active environment in Chestnut Hill, MA. Inventory is at 3.6 months, meaning a balanced environment with steady turnover. Inventory is balanced but lean, requiring buyers to be decisive.

Currently, $1,981,000 represents the median entry point in Chestnut Hill, MA. Over the past half-year, home values in Chestnut Hill have moved upward by approximately 22% based on regional transaction data.

Buyers have room for negotiation in Chestnut Hill, MA, with a Sale Price to List Price Ratio of 97.3%. On average, properties in Chestnut Hill are transitioning from active to sold status in 70 days.

Based on closed transaction data, Tina DiMonda ranks at the top of our Chestnut Hill leaderboard — with 2 completed transactions on record earning an algorithm performance score of 21. 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.

Chestnut Hill, MA maintains a distinct profile within the broader Middlesex region. Median home values are currently 83% higher than the regional average, reflecting the unique demand and inventory dynamics of Chestnut Hill.

Buyers targeting Entry Level Condo/Co-op homes in Chestnut Hill, MA may want to work with Richard C Dore. Their buyer transactions in the Entry Level Condo/Co-op category in Chestnut Hill, MA reflect genuine niche experience — a meaningful advantage over agents working this segment only occasionally.

Our data flags Ilene Solomon as a top buyer's advocate for Mid-Market Condo/Co-op properties in Chestnut Hill, MA. Across their deals in the Mid-Market Condo/Co-op category, Ilene Solomon has consistently achieved better-than-average terms relative to asking price in Chestnut Hill, MA. That kind of negotiating edge compounds over a transaction.

Among agents with recent closings in the Entry Level Condo/Co-op space, Tina DiMonda has the strongest performance metrics in Chestnut Hill, MA. Speed and price retention together are the hardest combination to find in a single agent. Their track record in the Entry Level Condo/Co-op category in Chestnut Hill, MA reflects both.

Ilene Solomon has been particularly active in Chestnut Hill's Mid-Market Condo/Co-op segment, and the numbers back it up. 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.

When looking specifically at Entry Level Townhome transactions, Brenda van der Merwe consistently surfaces as a top performer in Chestnut Hill, MA. Brenda van der Merwe's Entry Level Townhome transactions in Chestnut Hill, MA 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 High-End Detached Home in Chestnut Hill, MA, Deborah Gordon has the deal history to support the choice. For buyers competing in the High-End Detached Home market in Chestnut Hill, MA, their track record indicates speed and negotiating strength that outperforms the segment baseline on both counts.

In the Mid-Market Detached Home category, few agents in Chestnut Hill, MA can match the track record of MB Associates. 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.

Celine Sellam has helped buyers close on Mid-Market Detached Home properties in Chestnut Hill, MA — and the data shows it. Across their deals in the Mid-Market Detached Home category, Celine Sellam has consistently achieved better-than-average terms relative to asking price in Chestnut Hill, MA. That kind of negotiating edge compounds over a transaction.