Homes for Sale in Chester, MD

65 active listings · 1,285 sold since 2020

For Sale

$485K

Median Sale Price

Median Days on Market

98.0%

Sold-to-List

$251

Price / Sq Ft

Newest homes for sale in Chester, MD

See all 65 on the map

715 Warbler Way, Chester, MD 21619

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

723 Warbler Way, Chester, MD 21619

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

540 Warbler Way, Chester, MD 21619

Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

111 Marshgrass Way #21, Chester, MD 21619

Listing Courtesy of Samson Properties

2008 Bridgepointe Drive, Chester, MD 21619

Listing Courtesy of RE/MAX Executive

134 Richard Ingle Way, Chester, MD 21619

Listing Courtesy of Redfin Corp

124 Riverside Drive, Chester, MD 21619

Listing Courtesy of Douglas Realty LLC

2645 Cox Neck Road, Chester, MD 21619

Listing Courtesy of Compass

230 Switchgrass Way #12, Chester, MD 21619

Listing Courtesy of Real Broker, LLC - Chester

Chester, MD home price trend

Year	Median Sale Price	Homes Sold
2026	$532K	96
2025	$575K	181
2024	$597K	202
2023	$505K	187
2022	$430K	169
2021	$415K	227
2020	$390K	223

At the current trend, the median is modeled to reach about $623K in 2027 (estimate).

Cost to buy in Chester, MD

At today's ~6.63% 30-year rate, the median $485K home in Chester, MD runs about $3,131/mo with 20% down (principal & interest plus estimated taxes and insurance).

Estimate only — not a loan offer. Actual rate and payment depend on your profile.

Top agents in Chester, MD

Most active agents by closed sales here over the past 18 months.

Mary Anne KowalewskiKOVO Realty64 sales
Jennifer Anne ThomasRE/MAX Executive9 sales
Gueler StevensRealty Navigator9 sales
Ralph S. KennedyRE/MAX Executive8 sales
Dee Dee R MccrackenColdwell Banker Realty7 sales

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Chester, MD real estate FAQ

How many homes are for sale in Chester, MD?

There are 65 homes currently for sale in Chester, MD.

How much do homes sell for in Chester, MD?

The median sale price in Chester, MD is $485K, based on 1,285 sales since 2020 (ranging from $226K to $974K).

How fast do homes sell in Chester, MD?

Homes in Chester, MD typically go under contract in about 23 days on market (median).

Do homes in Chester, MD sell above asking?

Over the past 12 months, homes in Chester, MD sold for an average of 98.0% of list price — below asking.

What is the price per square foot in Chester, MD?

Homes in Chester, MD have sold for a median of $251 per square foot since 2020.

Is the Chester, MD housing market heating up or cooling down?

The median sale price in Chester, MD has risen from $390K in 2020 to $532K in 2026. At the current trend, the median is on track for roughly $623K in 2027 (modeled estimate).

Who are the top real estate agents in Chester, MD?

The most active agents in Chester, MD over the past 18 months are: Mary Anne Kowalewski (KOVO Realty) — 64 sales; Jennifer Anne Thomas (RE/MAX Executive) — 9 sales; Gueler Stevens (Realty Navigator) — 9 sales.

Homes for Sale in Chester, MD

Newest homes for sale in Chester, MD

Chester, MD home price trend

Cost to buy in Chester, MD

Top agents in Chester, MD

Get new-listing alerts for Chester, MD

Chester, MD real estate FAQ

How many homes are for sale in Chester, MD?

How much do homes sell for in Chester, MD?

How fast do homes sell in Chester, MD?

Do homes in Chester, MD sell above asking?

What is the price per square foot in Chester, MD?

Is the Chester, MD housing market heating up or cooling down?

Who are the top real estate agents in Chester, MD?

Neighborhoods & Subdivisions in Chester, MD