These Are the Most Expensive Streets to Live On in Boston

House hunting on a budget? Here are the addresses to avoid.

Photo via Getty Images/AlbertPego

If you’ve ever wandered down a charming brick sidewalk dotted with grand front doors, or looked up at buildings with wide windows and harbor views, and thought, I bet these homes are expensive, a new report is here to prove you right.

The real estate search portal gathered their home value data, averaged the numbers for streets with at least 10 homes, then ranked the whopping 121 streets with a minimum property value average of $500,000.

Homes values were calculated using the site’s Automated Valuation Model, which synthesizes information such as the property’s last sold date and price, a mortgage estimate, estimated value over time, and data on recently sold or for sale homes nearby, according to a digital marketing associate at

Here are the top five priciest streets in Boston:

Louisburg Square: Expensive real estate in Beacon Hill? Groundbreaking. Surrounding a rectangle of green park, this coveted block is sandwiched by Pinckney and Mt. Vernon streets, and blusters an average home value of $4.8 million.

Charles River Square: Be wary of addresses ending in “square,” apparently. As the name suggests, this small street lies between Charles Street and the Charles River. Beacon Hill brick or Esplanade grass? No need to choose here.

Union Street: Running parallel to Congress Street and perpendicular to Hanover, this lane is in the middle of it all—including the eponymous Union Oyster House.

Liberty Drive: The Seaport is expensive. We know this. But this harborside loop is the area’s most expensive, with an average home value of $2.8 million.

Commonwealth Avenue E: One of the city’s main stretches, it’s somewhat unsurprising that this road, which runs through Fenway and Back Bay, tops the charts.

most expensive streets in Boston

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Lagging slightly behind with home values from $2.3-2.4 million, streets such as Beacon Hill’s Brimmer Street, Cedar Lane Way, and Otis Place, Northampton Street in the South End, and the waterfront Rowes Wharf also boast extravagant price tags.

Though the report didn’t tackle data on the city’s most affordable streets, the least expensive of the $500k-plus bunch are: Rugdale Road, Saint Gregory Street, Waumbeck Street, Goodwin Place, and Aberdeen Street, which run through Dorchester, Roxbury, Beacon Hill (!), and Fenway.