NEIGHBORHOODS

Pilot Block

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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.

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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.

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Find the home you’ve been searching for.

$2,999,000
21 Nolan Cir
6 Bed | 6.5 Bath | 7,286 SQ.FT
2.02 Acres

$2,499,000
8 Twillingate Lane
5 Bed | 5.5 Bath | 4,120 SQ.FT
1.03 Acres

$2,450,000
35 Kato Drive
5 Bed | 3.5 Bath | 4,000 SQ.FT
1.38 Acres

$2,399,000
45 Widow Rites Ln
4 Bed | 4 Bath | 3,816 SQ.FT
1.33 Acres

$2,350,000
19 Skyview Lane
5 Bed | 6 Bath | 5,730 SQ.FT
1.69 Acres

$2,299,000
36 Cutler Farm Road
5 Bed | 3.5 Bath | 6,068 SQ.FT
6.25 Acres

$2,100,000
51 Atkinson Lane
5 Bed | 3.5 Bath | 5,438 SQ.FT
1.08 Acres

$2,099,000
65 Fox Run Rd
4 Bed | 2.5 Bath | 5,342 SQ.FT
1.53 Acres

$2,099,000
4 Twin Meadow Lane
4 Bed | 4.5 Bath | 4,973 SQ.FT
0.92 Acres

$1,999,999
7 Saddle Ridge Road
4 Bed | 2.5 Bath | 4,038 SQ.FT
0.92 Acres

$1,850,000
781 Boston Post Road
Bed | Bath | SQ.FT
14.56 Acres

$1,720,000
48 Chanticleer Road
5 Bed | 2.5 Bath | 4,874 SQ.FT
0.92 Acres

$1,699,000
42 Ironworks Rd
4 Bed | 3 Bath | 3,429 SQ.FT
0.71 Acres

$1,689,000
80 Pokonoket Ave
5 Bed | 3.5 Bath | 3,774 SQ.FT
0.56 Acres

$1,650,000
41 Phillips Rd
4 Bed | 3.5 Bath | 5,132 SQ.FT
0.92 Acres

$1,599,999
289 Willis Rd
5 Bed | 3.5 Bath | 4,158 SQ.FT
0.94 Acres

$1,599,000
111 Dutton Road
4 Bed | 3.5 Bath | 4,004 SQ.FT
5.35 Acres

$1,599,000
5 Harvard Drive
5 Bed | 4.5 Bath | 4,087 SQ.FT
0.94 Acres

$1,595,000
266 Landham
4 Bed | 4.5 Bath | 4,483 SQ.FT
0.95 Acres

$1,549,000
30 Meadow Dr
4 Bed | 2.5 Bath | 3,484 SQ.FT
0.85 Acres

$1,549,000
59 Highland Ave
4 Bed | 2.5 Bath | 4,087 SQ.FT
1.47 Acres

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$2,999,000
21 Nolan Cir
6 Bed | 6.5 Bath | 7,286 SQ.FT
2.02 Acres

$2,499,000
8 Twillingate Lane
5 Bed | 5.5 Bath | 4,120 SQ.FT
1.03 Acres

$2,450,000
35 Kato Drive
5 Bed | 3.5 Bath | 4,000 SQ.FT
1.38 Acres

$2,399,000
45 Widow Rites Ln
4 Bed | 4 Bath | 3,816 SQ.FT
1.33 Acres

$2,350,000
19 Skyview Lane
5 Bed | 6 Bath | 5,730 SQ.FT
1.69 Acres

$2,299,000
36 Cutler Farm Road
5 Bed | 3.5 Bath | 6,068 SQ.FT
6.25 Acres

$2,100,000
51 Atkinson Lane
5 Bed | 3.5 Bath | 5,438 SQ.FT
1.08 Acres

$2,099,000
65 Fox Run Rd
4 Bed | 2.5 Bath | 5,342 SQ.FT
1.53 Acres

$2,099,000
4 Twin Meadow Lane
4 Bed | 4.5 Bath | 4,973 SQ.FT
0.92 Acres

$1,999,999
7 Saddle Ridge Road
4 Bed | 2.5 Bath | 4,038 SQ.FT
0.92 Acres

$1,850,000
781 Boston Post Road
Bed | Bath | SQ.FT
14.56 Acres

$1,720,000
48 Chanticleer Road
5 Bed | 2.5 Bath | 4,874 SQ.FT
0.92 Acres

$1,699,000
42 Ironworks Rd
4 Bed | 3 Bath | 3,429 SQ.FT
0.71 Acres

$1,689,000
80 Pokonoket Ave
5 Bed | 3.5 Bath | 3,774 SQ.FT
0.56 Acres

$1,650,000
41 Phillips Rd
4 Bed | 3.5 Bath | 5,132 SQ.FT
0.92 Acres

$1,599,999
289 Willis Rd
5 Bed | 3.5 Bath | 4,158 SQ.FT
0.94 Acres

$1,599,000
111 Dutton Road
4 Bed | 3.5 Bath | 4,004 SQ.FT
5.35 Acres

$1,599,000
5 Harvard Drive
5 Bed | 4.5 Bath | 4,087 SQ.FT
0.94 Acres

$1,595,000
266 Landham
4 Bed | 4.5 Bath | 4,483 SQ.FT
0.95 Acres

$1,549,000
30 Meadow Dr
4 Bed | 2.5 Bath | 3,484 SQ.FT
0.85 Acres

$1,549,000
59 Highland Ave
4 Bed | 2.5 Bath | 4,087 SQ.FT
1.47 Acres

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$2M+ LUXURY MARKET DATA

The Pilot Block has long been one of the South End’s most consistent contributors to the luxury residential market, and 2025 continued to reflect the neighborhood’s enduring appeal. The Pilot Block recorded six closed sales above $2 million totaling $27,802,000, a measured level of activity that followed a notably stronger 2024, when 16 sales generated $54,627,500.

$33,902,000 TOTAL SALES VOLUME

$1,409 AVG. PRICE PER SQ. FOOT

7 NUMBER OF $2M+ PROPERTIES SOLD