“Brad was the best Realtor around. He cared deeply and treated my family as his. I can't thank Brad enough. I will recommend him to every single person that I know who is looking to buy or sell a home.”
Century 21 North East
- Agent Pronto
- Massachusetts
- Newton
- Chestnut Hill
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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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Chestnut Hill real estate Market Report.
Information and statistics on the latest trends in the Chestnut Hill real estate market, updated for March 2026. *
Chestnut Hill’s home values have shifted notably from a year ago, with typical values down about 24.44 percent. Inventory has also fallen 52.17 percent year over year, while pending sales are down 50 percent. New listings declined even more sharply, dropping 74.19 percent compared with last year.
In February 2026, the typical home value in Chestnut Hill was about $1,700,000, higher than Newton’s $1,487,500. Homes spent a median of 28 days on the market, which is 66.67 percent faster than a year earlier even as days on market ticked up 14.29 percent from the prior month.
Buyers saw a median list price of $1,099,000 with 11 homes on the market, 8 new listings, and 6 going under contract, and only about 11 percent of recent sales closed above asking with an average sale-to-list ratio near 0.93. Looking ahead to March 2026, typical values in Chestnut Hill are projected to edge up to about $1,796,875, while inventory is expected to increase to 13 homes even as the broader area of Newton heads toward a typical value of roughly $1,488,750. With a seller’s market reading of 18 on the local gauge, both buyers and sellers can benefit from Agent Pronto’s help in connecting with a knowledgeable agent who understands these dynamics.
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Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Learn more about what Chestnut Hill has to offer.
Chestnut Hill offers residents a village-like vibe with charming shops, ample green spaces, strong schools, and easy access to transit and nearby city conveniences.
Chestnut Hill immediately feels distinct from nearby Newton villages and Brookline, combining a leafy residential setting with destination retail and respected schools. Around the Chestnut Hill Reservoir, walkers and runners share paths with commuters heading toward Boston on the Green Line, a reminder that this quiet enclave stays closely connected to the city.
Tree lined streets feature substantial single family homes, historic properties, and a growing number of luxury condos. The Shops at Chestnut Hill and The Street Chestnut Hill bring upscale restaurants, cafés, and everyday services, while nearby Boston College adds cultural events and athletic energy. Families are drawn to strong local schools such as Newton South High School and access to parks like Hammond Pond Reservation for hiking and nature.
Housing here is competitive and inventory is often limited, especially for updated homes close to transit or shopping. Sellers benefit from thoughtful preparation and pricing that reflects micro differences between pockets near Brookline, Brighton, and West Roxbury. Buyers who understand timing, financing, and neighborhood nuances have an advantage when the right property appears.
Whether you are already a Chestnut Hill resident or considering a move from nearby Allston or Jamaica Plain, connecting with the right local expert matters. Agent Pronto can match you with a real estate agent who knows how to position sellers and prepare buyers to succeed in this competitive market.
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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!”
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.”
SR Realty
“Spencer is a gem! From the start, his deep knowledge of the market and attention to detail when we were looking at properties blew us away. He’s always available, whether to answer questions or provide guidance, making us feel completely supported every step of the way. Spencer’s approachable, funny, and yet always professional—he truly made the process enjoyable and stress-free. He handled the sale of our home with perfection, the entire process was above expectations. Highly recommend him to anyone looking for an outstanding realtor!”
Topp Realtors
“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.”
Century 21 North East - Integra
“Great real estate experience with Charlotte. I recently had the pleasure of working with Charlotte as my realtor, and I cannot express how grateful I am for her outstanding service throughout the entire home buying process. From our initial meeting to the closing day, Charlotte demonstrated a level of professionalism, expertise, and dedication that greatly met my expectations. One of Charlotte's standout qualities is her extensive knowledge of the local real estate market. She took the time to understand my preferences and priorities, providing valuable insights into neighborhoods, property values, and future market trends. Her expertise not only streamlined the decision-making process but also ensured that I made informed choices.”
Berkshire Hathaway Verani Realty
“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.”
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.”
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.”
Elias Group Realty
“Can't recommend Smita enough - she is extremely knowledgeable, is well aware of the ins and outs of the local market, and will always guide you towards the best decision based on your requirements. Smita played a huge role in helping me and my wife find our dream home. Being first-time homeowners, we didn't know where to start, but Smita did great due diligence researching individual properties and analyzing local market trends. Before we went to see a property, we had all the links and documents we needed to learn about the property which was immensely helpful in making an informed decision. Smita was always available for us which made the whole process very smooth for us. My wife and I highly recommend Smita and would to work with her again.”
Keller Williams Pinnacle MetroWest
“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.”
Michelle Lane Real Estate
“Elena is one of a kind just like how she found my perfect home for me in West Boylston, Massachusetts. I am from San Diego, California and never would have imagined to own a home in central Massachusetts but she opened my eyes to a beautiful town of West Boylston and provided great statistical feedback to help me make my decision. I am happy with my decision and a lot of it comes from a skilled and professional agent such as Elena. Highly recommend her.”
Keller Williams Boston Metrowest
“I found Lyn through an online realtor search. She called me right away and I was impressed with her grasp of our complex situation: we were buying a house for us and my mother in law and selling our home as well as my mother inlaw’s home in NJ. Lyn gave us great advice at every turn of this long and sometimes arduous journey!! So glad we hooked up with her from the start! She worked so hard for us!! When our first buyers lost their financing she said she wanted to have an open house every weekend until we got another buyer and she did it! We didn’t deal directly with other century 21 staff but I know Lyn consulted with others from her group at times. It was reassuring to know there was a whole team on our side working for our common goal. Lyn was so professional and reliable; it was truly a pleasure working with her.”
Century 21 The Real Estate Group
“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.”
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. ”
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.”
Engel & Völkers
“It was great working with Sam Renuka , do you help my brother and sister find their dream home,and as time passes me and my wife decided to look for a place of our own so we decided to call Sam up and after five years he still remembers me and my family,there's a lot of stress and buy your house and he made the experience more enjoyable definitely recommend him,The seller agent was very please with him to.”
REVA CAPITAL REALTY
“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”
Zander Realty Group
Frequently Asked Questions
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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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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Chestnut Hill Realtor® or real estate agent today.
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