NEIGHBORHOODS

Brookline

Find your Brookline niche area to explore.

OVERVIEW

Brookline hosts a wide array of real estate offerings ranging from the grand estates of Chestnut Hill and Cottage Farms to the more moderately priced two-family and condo inventory in Washington Square, Coolidge Corner and Brookline Village. Known for its blend of suburban charm and urban convenience, Brookline serves as a wonderful transition from urban living to the suburban dream.

Brookline has long been a playground for the wealthy and well-connected, attracting business leaders, renowned academics, and professional athletes who appreciate its privacy, prestige, and proximity to Boston. Brookline’s Chestnut Hill Estates are home to some of the most expensive and private residences in Massachusetts, with sprawling mansions tucked away behind manicured hedges and robust gates. Often owned by CEOs, surgeons, and influential figures in Boston’s finance and real estate sectors, these homes are truly stunning trophies within the broader realm of estates nationally. This area surrounds one of the most exclusive and prestigious private clubs in the country, The Country Club. This club is steeped in history, dating back to its founding in 1882.

Explore by the Building

For when you know where you want to live and just need to know when the right unit comes available.

Terrazza

The Tudor

Pierce Boston

Exploring Brookline with Claire McClintock

Claire has been lucky enough to call this town home for many years.

Brookline has a depth that reveals itself slowly: layered history, unmistakable character, and a collection of neighborhoods that each feel like their own small world. From #FisherHill to #BrooklineVillage, #CottageFarms to #CoolidgeCorner (and many more of pockets in between), no two areas are quite the same. Some streets feel timeless and residential, others hum with energy and life—but all of them carry a strong sense of community.

So, explore Brookline with Claire, one neighborhood at a time, and learn what makes each corner unique—and maybe uncovering a few lesser-known spots along the way.

Search to Buy

Search to Rent

Get Ready to Sell