Pilot Block

South End

Overview

The Pilot Block claims to be the oldest neighborhood association in the South End. While we cannot verify that claim, we do know that the Pilot Block area is an underrated gem when it comes to high end properties in the broader city. The Pilot Block’s strategic location is idyllic for those who covet equal access to the Back Bay’s commercial offerings as well as the South End’s more eclectic culture and boutiques.

 

 

Jamie's South End Series: Pilot Block


Pilot Block area is an underrated gem when it comes to residential areas in the South End. This neighborhood claims to be the oldest neighborhood association in the South End. While I’m not sure if that’s true, I do love the easy access to public green spaces and charming boutiques that created the perfect environment for high end real estate!

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Location

Pilot Block includes lower West Canton Street along with West Newton, Pembroke, West Brookline, and Warren Avenue. The neighborhood’s residents enjoy easy access to Dartmouth Square, James Hayes Park, and Harriet Tubman Square.

Three parallel streets within the Pilot Block control the majority of the housing inventory in this sub neighborhood. West Canton, West Brookline and Pembroke Streets all command premium pricing for real estate sales. A particularly enticing row of houses on West Canton Street backs up to a “secret garden” known as Montgomery Park.

$2M+ Luxury Market Data

One of the top contributors to the South End’s luxury residential markets has traditionally been the Pilot Block, and that was no exception in 2024. Pilot Block reached a total of 16 sales over $2M in 2024, equating to $54,627,500 in sales volume. Out of all of the sub-neighborhoods in the South End, Pilot Block accounted for 17% of total sales volume for 2024. Even though Pilot Block was near the top of the list for South End’s luxury sales, the area did decrease in transactions from 2023, down $9,823,220 in sales volume from last year. 

Pilot Block 2024: Off-Market Deals and a Notable Price Drop

Notably, 2 of the 16 total sales in Pilot Block were off-market sales in 2024 – 90 Dartmouth St, which sold for $2,940,000, and 147 Warren Ave, which sold for $2,300,000. The top sale in this area was a single family at 165 West Brookline Street which sold for $5,725,000. After being on the market for six months, the seller dropped their price by seven percent and found a buyer within a week… the final sales price was 12 percent below the original ask.

We believe when real estate consumers are presented with a complete and robust spread of data, in conjunction with their personal preferences, decisions can be reached with the most confidence.

To learn more about changing market dynamics moving into 2025 check out our Perspective on the Boston Luxury Housing Market>