House Prices

Chester Square Boston, MA House Prices & Home Values 2026


Average Data

average house price$1,245,531
average size per house840 ft²
average price per ft²1361 $ / ft²

04/15/2026 - The value range (VR) for house prices in Chester Square Boston, MA is $1292.95/ sqft to $1429.05/ sqft. An average home with 840 sqft costs approximately $995,934 to $1,100,769. Boston, MA includes 1 ZIP codes and it is located in Suffolk county. The lowest prices are found in ZIP 02118, while the highest are in ZIP 02118. The average price per sqare feet is $1361. Our analysis is based on 12 property listings.

Avergage prices by ZIP codes Chester Square Boston

021181219 $ / ft²




Historical development of home values in Chester Square Boston

Year Estimated value (USD) Change vs. 2025
2010 $578,447 -53.6%
2011 $556,079 -55.4%
2012 $554,581 -55.5%
2013 $575,310 -53.8%
2014 $603,917 -51.5%
2015 $634,912 -49.0%
2016 $668,046 -46.4%
2017 $704,103 -43.5%
2018 $743,030 -40.3%
2019 $777,483 -37.6%
2020 $817,675 -34.4%
2021 $930,018 -25.3%
2022 $1,084,192 -13.0%
2023 $1,143,330 -8.2%
2024 $1,209,474 -2.9%
2025 $1,245,531 0.0%

Graph: estimated home values in Chester Square Boston over time (USD)



Example: 100% financing house in Chester Square Boston

Loan amount: $1,245,531

Interest rate: 5.50%

Fixed monthly payment: $7,073.55

Breakdown in the 1st month:
Interest portion: $5,710.76  –  Principal portion: $1,362.79

Yearly breakdown (100% financing)

Year Interest per year ($) Principal per year ($) Remaining balance at year-end ($)
1 $68,110.35 $16,772.26 $1,228,758.74
2 $67,163.91 $17,718.70 $1,211,040.04
3 $66,164.07 $18,718.55 $1,192,321.50
4 $65,107.80 $19,774.81 $1,172,546.68
5 $63,991.93 $20,890.68 $1,151,656.00
6 $62,813.09 $22,069.52 $1,129,586.48
7 $61,567.73 $23,314.88 $1,106,271.60
8 $60,252.10 $24,630.51 $1,081,641.08
9 $58,862.23 $26,020.39 $1,055,620.70
10 $57,393.93 $27,488.69 $1,028,132.01
11 $55,842.77 $29,039.84 $999,092.17
12 $54,204.08 $30,678.53 $968,413.64
13 $52,472.93 $32,409.69 $936,003.95
14 $50,644.08 $34,238.53 $901,765.42
15 $48,712.04 $36,170.57 $865,594.85
16 $46,670.98 $38,211.64 $827,383.22
17 $44,514.74 $40,367.88 $787,015.34
18 $42,236.82 $42,645.79 $744,369.55
19 $39,830.37 $45,052.24 $699,317.31
20 $37,288.12 $47,594.49 $651,722.82
21 $34,602.41 $50,280.20 $601,442.62
22 $31,765.16 $53,117.45 $548,325.17
23 $28,767.80 $56,114.81 $492,210.35
24 $25,601.30 $59,281.31 $432,929.04
25 $22,256.12 $62,626.49 $370,302.56
26 $18,722.18 $66,160.43 $304,142.13
27 $14,988.82 $69,893.79 $234,248.33
28 $11,044.79 $73,837.82 $160,410.51
29 $6,878.21 $78,004.41 $82,406.11
30 $2,476.50 $82,406.11 $0.00

Note: The calculation is based on a standard annuity mortgage with a fixed monthly payment over the entire term. Extra payments, interest rate changes, and additional purchase costs (e.g. taxes, notary fees) are not included.


How to sell in Chester Square Boston, MA


1500 sqft3900 sqft
Ø selling price$2,265,188$4,818,671
Ø fast selling$2,059,262$4,336,804
Ø high price sale$2,471,114$5,300,538

In 2026, houses in Chester Square Boston, MA will be offered at an average price of $1361 per square foot. A 1,500 sqft home priced at $2,265,188 is 21.09% more expensive per square foot than a 3,900 sqft home priced at $4,818,671. Home prices in Chester Square Boston, MA vary significantly depending on the property’s condition and exact location. For a quick sale, a 2,700 sqft home should be listed at around $3,336,003. Sellers who can wait longer may achieve a higher price of up to $4,077,337.


Chester Square, Boston MA Neighborhood Guide

Overview and Location

Chester Square Boston MA is a historic pocket of the South End known for Victorian brownstones and leafy streets.

Centered along Massachusetts Avenue near Blackstone and Franklin Squares, the area offers classic architecture within minutes of Back Bay and Downtown.

Lifestyle and Amenities

Residents enjoy a walkable lifestyle with cafes, boutiques, and art galleries along Tremont, Washington, and Shawmut.

Green spaces and dog-friendly parks create a neighborly vibe, while seasonal events and South End Open Studios add creative energy.

Dining and Culture

From acclaimed restaurants on ?Restaurant Row? to cozy bakeries, the Chester Square area delivers diverse dining and nightlife.

Proximity to Symphony Hall, the SoWa Art + Design District, and cultural institutions enriches daily life.

Transportation and Access

Excellent transit options include nearby MBTA Orange and Green Line stops, frequent buses on Massachusetts Avenue, and Bluebikes stations.

Drivers benefit from quick links to I-90 and I-93, while dedicated bike lanes support eco-friendly commuting.
Walk Scores are high, making errands and entertainment easy without a car.

Housing and Community

Real estate ranges from restored rowhouse condos to modern apartments, and active groups like Chester Square Neighbors foster community engagement and neighborhood advocacy.



FAQ – Home Values in Chester Square Boston

What is the median home value in Chester Square Boston in 2026?

In 2026, the typical home value in Chester Square Boston is about $1,245,531 for an average home size of 840 square feet. This corresponds to an average price of roughly $1361 per square foot.

What is the average cost per square foot in Chester Square Boston?

In 2026, homes in Chester Square Boston sell for an average of around $1361 per square foot, with a typical range between $1292.95 and $1429.05 per square foot, depending on the property’s location, condition, and lot size.

What is the average home size in Chester Square?

The average home size in Chester Square Boston is about 840 square feet, with an estimated 2026 value around $1,245,531.



Neighborhoods close to Chester Square Boston, MA

Fort Hill Highland Park Roxbury, MA1500 $ / ft²
Mission Hill Roxbury Crossing, MA674 $ / ft²
Neponset Dorchester, MA434 $ / ft²
Wrentham Center Wrentham, MA459 $ / ft²
Islington Westwood, MA405 $ / ft²
Stoughton Center Stoughton, MA238 $ / ft²




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