Chestnut Hill

Welcome to Chestnut Hill

Chestnut Hill

Chestnut Hill, MA real estate is property unlike anywhere else, as Chestnut Hill is neither a township nor a neighborhood.

Straddling Norfolk, Middlesex and Suffolk counties, this village is arguably the most sought after real estate in all of New England. Located just 6 miles from downtown Boston, it's part Brookline, part Boston, and part Newton, making it one special place.

There’s a good reason Tom Brady, Robert Kraft, John Henry, and other notable Boston residents have (or had - we miss you, TB12!) called Chestnut Hill home. Chestnut Hill real estate has some of the most exclusive views of the Greater Boston Area, while simultaneously offering beautifully private and secluded land.

Chestnut Hill - Part City, Part Getaway

Although the name may sound like Chestnut Hill is one big hill, it's actually several smaller hills encircling the Chestnut Hill Reservoir. At the same time, it’s accessible to several routes on the MBTA’s Green Line as well as various bus routes, making it very pedestrian-friendly.

Here are just a few of Chestnut Hill more notable sites and institutions: 

• Boston College
• Boston Marathon Route
• Pine Manor College
• Hammond Park Reservation
• Chestnut Hill Reservoir

Chestnut Hill is perfect for those who love to have their own space and exclusive privacy while being minutes away from all the best Boston has to offer. Natural beauty, history, and refinement define Chestnut Hill, MA real estate.

Lost Pond Sanctuary and Skyline Park

This beautiful 58-acre property includes walking trails, skyline views of the city, fields for sports, and various playgrounds. The Sanctuary great for all ages, from young children to adult joggers - it’s a splendid place to spend an outdoor day! Also, Lost Pond is a “quaking bog,” which means peat moss forms on top of the water. It's truly a unique sight to behold - it’s like a giant floating green mat! 

The Shops at Chestnut Hill 

The Shops at Chesnut Hill is one of the most desirable shopping destinations in all of Greater Boston, not to mention New England! The Shops at Chestnut Hill has been a landmark in the community for decades, and it’s got everything you could want in a mall. There are over 50 shops, including the only Bloomingdale’s retail store in Massachusetts. After the shopping is over - Frank Pepe’s Pizza, anyone? 

The Street

The Street has emerged as a unique and community-driven shopping center that residents frequent many times of the week. The Street is over 640,000 square feet of shopping, dining, and entertainment. This includes one of my favorite places to see a movie, the Showcase SuperLux. It’s a truly luxurious experience! The Street overlooks Hammond Pond, a distinctive and beautiful nature reservation.

Hammond Pond Reservation

Hammond Pond is a place I love to head with my family for hiking, walking, fishing, and sometimes when I’m feeling brave, rock climbing! The Hammond Pond Reservation is part of the Metropolitan Park System of Greater Boston - I’ve been going there since I was a child, and I’m happy it’s a place I can share with my children. It’s a staple of Chesnut Hill and a destination for all who know how special it is.