The best way to find top real estate agents in Chestnut Hill, Boston, MA

Skip the search. We analyze thousands of real estate agents in Boston’s Chestnut Hill neighborhood and nationwide to find you proven local pros, for free.

Real estate in Boston’s Chestnut Hill neighborhood.

Compare top Chestnut Hill real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for March 2026. *


* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.

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Learn more about what Chestnut Hill has to offer.

Chestnut Hill provides residents with a balanced blend of historic charm, green spaces, top-rated schools, and convenient access to shops, dining, and both urban and suburban amenities.

Real estate in Boston’s Chestnut Hill neighborhood.

Chestnut Hill attracts buyers who want residential calm with quick access to city life. Professionals commuting into Boston, families seeking strong schools, and empty nesters ready to downsize all tend to thrive here thanks to tree-lined streets, established homes, and convenient retail and transit.

Housing includes classic single-family homes near Boston College, updated colonials, and luxury condos close to The Street at Chestnut Hill and Chestnut Hill Reservoir. Proximity to Boston College shapes parts of the neighborhood, while quieter pockets closer to Newton and Brookline appeal to long-term residents. The Green Line makes downtown commutes manageable, and local spots like The Street Chestnut Hill and Chestnut Hill Square provide shopping, dining, and everyday services.

Buyers often compare areas along the MBTA Green Line or look just beyond the city in places like Somerville and Cambridge. In Chestnut Hill, though, pricing and lifestyle can vary block by block depending on school districts, parking rules, and traffic patterns around the reservoir and retail centers.

That is why working with an agent who understands micro-differences across Chestnut Hill is essential, from condo associations near the reservoir to single-family zoning on quieter streets. Agent Pronto can connect both buyers and sellers with a local expert who knows the neighborhood-level details that truly shape value and everyday living.

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“As first-time home buyers navigating a competitive market, we truly could not have purchased the home we wanted without Jill Fitzpatrick. Jill was incredibly helpful and responsive from day one, really listening to our needs and wants and then tailoring experienced advice and next steps accordingly. We were able to put in a winning offer which included a quick closing timeline only with the help of Jill guiding us through each step of the process. We can't recommend Jill enough!”

Katy · Malden, MA

Photo of Jill Fitzpatrick
Century 21 C21 North East
“Sarah Rodewald was excellent, especially with being a first time home buyer. She was friendly and responsive when I had questions or concerns. Sarah was a strong advocate for me during negotiations to secure a fair price and credits towards closing. I would highly recommend Sarah for anyone looking for a dedicated expert agent.”

Andrew C · Walpole, MA

Photo of Sarah Rodewald
SR Realty
“Len went above and beyond during the whole process of selling my mother's home. He was kind, considerate, compassionate and extremely helpful, during an especially stressful time. I would definitely recommend him without hesitation.”

Denise Kastrinakis · Beverly, MA

Photo of Len Ferrari
Century 21 North East - Integra
“I can't thank John Dean enough for handing the sale of my home. John's knowledge of the industry and the area was exceptional. He kept me informed of all the issues and guided me with decisions that had to be made. He offered to make several trips to the house to meet and coordinate the inspections and other people that assisted me with the move. Not being available to make it to the property for various reasons being the distance and caring for a disabled husband, John saved me from having to be there. John was there to manage everything for me. If you need a professional agent, look no further than John Dean.”

Anna T. · Malden, MA

Photo of John Dean
Engel & Völkers Engel & Volkers Boston
“I interviewed several Realtors, and none of them asked the thoughtful questions that Katherine did to better understand my needs. She also demonstrated a deep knowledge of the Boston program I was using for financing, and her years of experience working in and around Boston was key. But more than anything else, we got along really well in our initial meeting and she had my full trust almost as soon as the process began.”

Valerie Tracy · Dorchester, MA

Photo of Katherine Meisenheimer
LAER Realty Partners
“He was honest enough to direct us away from one of the homes that we looked at because of the horrible basement there. He also showed us at least 5+ homes before we settled on the one we're living in now.”

Thomas McLeod · Sutton, NH

Photo of Philip Elias
Elias Group Realty
“We were referred to Michelle by a friend. She knows Newton and the surrounding areas; she knows real estate; she knows everyone associated with real estate, including mortgage brokers, inspectors, and insurance agents. Michelle is very professional but also personable. She has a knack for explaining markets trends and is skilled at reading the psychological aspects of an offer/counter-offer. She was extremely responsive and helped us buy an incredible house in a great location - in the hottest market in history! In short, I recommend Michelle with great enthusiasm. She is the absolute best.”

Penny · Newton, MA

Photo of Michelle Lane
Michelle Lane Real Estate
“I was recommended by a friend to call Kerry Lapiana with Prestige Homes. I am so glad I did. Kerry went up and beyond from the beginning until the end. She was always available with any questions I had and she made the offer process so easy. It didn't end there. She even took time after I closed to ask me how it was going if I needed anything additional. She went up and beyond every step of the way. I would highly recommend Kerry Lapiana and Prestige Homes to friends, family and colleagues.”

RHD · Medford, MA

Photo of Kerry LaPiana
Diamond Key Real Estate
“We were matched up with Greg Maund who was an incredible broker and help us get the apartment of our dreams. ”

Sharon R. · Boston, MA

Photo of Greg Maund
William Raveis Residential
“Scott was excellent and I highly recommend him. As a first time buyer, I had many questions and concerns, and he answered and alleviated all of them. We were on the same page from the start regarding strategy, and he deftly navigated through a couple unexpected and complicated situations after the initial offer had been accepted. I definitely plan on using Scott for any future real estate needs.”

Nate · Boston, MA

Photo of Scott Paskerian
Engel & Völkers
“Kyle moore and kim arsenalt saved my llife. I Just had a son. Lost my mom. My paperwork wasnt great. these 2 put things together that i couldnt have emagined.hear i am now in a multi. Tenants ask how i want the rent paid. I look at them like they're crazy for 2 seconds and say "check or M.O.".IF YOU Feel like me. Those are the ones you want on your team. Then grab KATHY as the lawyer. Shes the best too”

Ben Moore · Brockton, MA

Photo of Zander Realty Group
Zander Realty Group

Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Chestnut Hill. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.


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