Discover Chestnut Hill

The Massachusetts village of Chestnut Hill, known as one of the most affluent neighborhoods in Greater Boston, remains one of the most celebrated and protected villages in New England. Home to breathtaking luxury residences, varied architectural styles, as well as numerous shopping plazas and upscale dining, this village located a mere six miles southwest of Boston's downtown is now a vibrant, cultural hub.


Since the Hammond family first settled it in 1665, part of the allure of Chestnut Hill is due to the preservation of its rich history. At one time split between Newton and Boston, Chestnut Hill was ceded to Boston in the 1800s, leading to far more residential and commercial developments. The village itself now rests partially within multiple municipal entities, including three counties: Brookline in Norfolk County; Newton in Middlesex County; and both the Brighton and West Roxbury neighborhoods of Boston in Suffolk County.

Boston College, a top-ranked, private Jesuit research university founded in 1863, still today attracts many residential hopefuls and their aspiring students that anticipate pursuing their higher education within its famed walls. In fact, the small liberal arts college's main campus features some of North America's earliest examples of collegiate gothic architecture. In one area of this affluent and idyllic neighborhood known to residents as “Old Chestnut Hill Historic District,” residents can enjoy preserved 19th and early 20th century homes in the historic residential center of its Newton borders. Among the many architectural periods and styles known to last in Chestnut Hill are the Georgian, Colonial, and Revival structures. With the Chestnut Hill Local Historic District established in 1991 to preserve and extend the life of its historic architecture, both new and established residents will be able to enjoy the beauty of this warm and inviting neighborhood and its defining characteristics for many years to come.

Why Chestnut Hill

Chestnut Hill was originally named for its series of small hills overlooking the 135-acre Chestnut Hill Reservoir. Today, Chestnut Hill's claim to fame extends to its list of illustrious residents, including former NFL quarterback Tom Brady, as well as Red Sox and Liverpool F.C. principal owner John W. Henry. Athletes of a different sort may also want to call Chestnut Hill home as the Boston Marathon, the world's oldest annual marathon, includes the village in its route. With an even greater emphasis on academics, the educational institutions in Chestnut Hill draw many new residents looking to share in its history, most notably for the highly-selective Boston College.

There are several popular shopping districts or plazas, as they may also be called, within Chestnut Hill itself. If you're looking to expand your culinary palette or experience luxury services, The Street at Chestnut Hill or The Shops at Chestnut Hill are centers that will keep you coming back for more. If you're wanting to shop and dine on a smaller scale, Chestnut Hill Square and The Shops at Putterham are perfect for a more local, low-key experience. Cleveland Circle, Newton Centre, Newton Highlands, and the Needham Street Shopping Corridor round out the local options with a few more popular chain restaurants, stores, and markets like Chipotle, HomeGoods, CVS, and more.

To learn more about some of the amenities, transportation systems, and academic institutions Chestnut Hill has to offer – and see why this sought-after village has stood the test of time — visit our Chestnut Hill community guide, read about top Chestnut Hill schools including private and public PreK-12 and higher education, and discover luxury shopping and fine-dining experiences with our local resources.

Find Your Forever Home in Chestnut Hill

There are many reasons why you should consider moving to Brookline, or Newton, from our excellent public and private schools to lovely preserved historic buildings, architecturally diverse residences, and scenic grounds. If you are considering purchasing or selling a home in Chestnut Hill – or perhaps Brookline or Newton – or if you simply want to learn more about Chestnut Hill, I can handle all of your questions.

Whether you are looking for a new single-family housecondo, or investment property, I will help you navigate the current market to find the place you can call home. Contact me online or call my office at 571-481-0440 to get started on your journey!