Chestertown, MD housing market
The typical Chestertown home is worth about $391,000, up 1.9% in a year, 9% below the Maryland typical home.
Home values, sales, trends and how Chestertown compares with the towns next door — updated as new data is published.
Chestertown at a glance
Typical home value, 2016–2026
Show as a table
| January | Chestertown | Maryland |
|---|---|---|
| 2017 | $226,000 | $290,000 |
| 2018 | $237,000 | $301,000 |
| 2019 | $244,000 | $310,000 |
| 2020 | $257,000 | $322,000 |
| 2021 | $288,000 | $349,000 |
| 2022 | $331,000 | $384,000 |
| 2023 | $342,000 | $398,000 |
| 2024 | $361,000 | $412,000 |
| 2025 | $383,000 | $427,000 |
| 2026 | $388,000 | $429,000 |
| August 2026 | $391,000 | $428,000 |
18 new homes permitted in 2025
Builders were permitted 18 new homes in Chestertown in 2025: 2 single-family houses and 16 in buildings with two or more homes, worth about $3.2 million to build. That's 3.2 per 1,000 residents, faster than across Maryland (2.4). Over the past 10 years, Chestertown has permitted 120 homes in all.
Homes vs. people, 2010–2020
Between the 2010 and 2020 censuses, Chestertown gained 280 residents while 41 new homes were permitted: about 6.8 new residents per new home. Population grew faster than building, so existing homes filled up: a sign of tight supply. Across Maryland: 2.5 new residents per new home.
Residents: U.S. Census Bureau, 2010 and 2020 censuses. New homes: permits issued 2010–2019.
Show as a table
| Year | New homes | Single-family | 2+ per building | Value |
|---|---|---|---|---|
| 2026 (Jan–Aug) | 4 | 4 | 0 | $909,000 |
| 2025 | 18 | 2 | 16 | $3.2 million |
| 2024 | 4 | 4 | 0 | $1.5 million |
| 2023 | 31 | 31 | 0 | $9.3 million |
| 2022 | 35 | 31 | 4 | $6.2 million |
| 2021 | 10 | 4 | 6 | $2.7 million |
| 2020 | 13 | 5 | 8 | $2.5 million |
| 2019 | 1 | 1 | 0 | $400,000 |
| 2018 | 0 | 0 | 0 | — |
| 2017 | 1 | 1 | 0 | $318,000 |
| 2016 | 7 | 7 | 0 | $1.4 million |
| 2015 | 3 | 3 | 0 | $656,000 |
| 2014 | 4 | 4 | 0 | $1.9 million |
| 2013 | 3 | 3 | 0 | $1.2 million |
| 2012 | 4 | 2 | 2 | $1.2 million |
| 2011 | 0 | 0 | 0 | — |
| 2010 | 18 | 18 | 0 | $2.5 million |
| 2009 | 68 | 68 | 0 | $12.7 million |
| 2008 | 27 | 27 | 0 | $4.5 million |
| 2007 | 57 | 46 | 11 | $11.4 million |
| 2006 | 55 | 55 | 0 | $11 million |
| 2005 | 27 | 27 | 0 | $5 million |
| 2004 | 34 | 34 | 0 | $3 million |
| 2003 | 37 | 37 | 0 | $4.2 million |
| 2002 | 47 | 11 | 36 | $3.1 million |
| 2001 | 11 | 11 | 0 | $1.4 million |
| 2000 | 4 | 4 | 0 | $455,000 |
How Chestertown ranks on new homes being built →
Homes authorized by building permits, counted in the year the permit was issued. U.S. Census Bureau, Building Permits Survey, through August 2026.
7.2 years of income
The typical Chestertown home costs about 7.2 years of the town's median household income, more than across Maryland (4.1 years).
How Chestertown ranks on affordability →
Home value ÷ ACS median household income.
Owners, rent & taxes
U.S. Census Bureau, ACS 2020-2024.
A two-bedroom rents for about $1,770
HUD's Fair Market Rent for a two-bedroom in Chestertown is $1,770 a month, utilities included: roughly what a modest, recently rented unit costs. Renters already in Chestertown pay a median of $1,206, so moving in tends to cost more than staying put. A two-bedroom takes about 39% of the town's median household income, above the 30% guideline for affordable housing.
Studio $1,270 · 4 bedrooms $2,550
U.S. Department of Housing and Urban Development, FY2026 Fair Market Rents by ZIP code (21620; Baltimore-Columbia-Towson, MD MSA), weighted by land area. A Fair Market Rent is the 40th-percentile rent plus utilities for a standard unit. Median rent: U.S. Census Bureau, American Community Survey.
Home values: Zillow Home Value Index (ZHVI), Zillow Research, August 2026. Sales, days on market and supply: Redfin Data Center. Income, ownership, taxes and rent: U.S. Census Bureau, American Community Survey. New homes: U.S. Census Bureau, Building Permits Survey. Fair Market Rents: U.S. Department of Housing and Urban Development. Listings link to their publishers.