Homes for Sale in Chestertown, MD

50 active listings · 1,103 sold since 2020

For Sale

$314K

Median Sale Price

Median Days on Market

97.5%

Sold-to-List

$183

Price / Sq Ft

Newest homes for sale in Chestertown, MD

See all 50 on the map

21324 Persimmon Drive, Chestertown, MD 21620

Listing Courtesy of Benson & Mangold, LLC

210 N Queen Street, Chestertown, MD 21620

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company

522 High Street, Chestertown, MD 21620

Listing Courtesy of Benson & Mangold, LLC

Preston Lane, Chestertown, MD 21620

Listing Courtesy of Shoreline Realty

121 Metcalf Road, Chestertown, MD 21620

Listing Courtesy of Real Broker, LLC - Chester

10781 Fermoy Road, Chestertown, MD 21620

Listing Courtesy of Real Broker, LLC - Chester

409 Calvert Street, Chestertown, MD 21620

Listing Courtesy of Chesapeake Real Estate Associates, LLC

10720 Foreston Road, Chestertown, MD 21620

Listing Courtesy of Compass

200 Manor Avenue, Chestertown, MD 21620

Listing Courtesy of TTR Sotheby's International Realty

Chestertown, MD home price trend

Year	Median Sale Price	Homes Sold
2026	$350K	75
2025	$419K	116
2024	$345K	143
2023	$320K	165
2022	$352K	146
2021	$270K	245
2020	$256K	213

At the current trend, the median is modeled to reach about $412K in 2027 (estimate).

Cost to buy in Chestertown, MD

At today's ~6.63% 30-year rate, the median $314K home in Chestertown, MD runs about $2,027/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 Chestertown, MD

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

Liddy CampbellTTR Sotheby's International Realty11 sales
Retha J ArrabalDoug Ashley Realtors, LLC10 sales
Peter D HellerColdwell Banker Chesapeake Real Estate Company7 sales
Kristina L HylandColdwell Banker Chesapeake Real Estate Company7 sales
Michael OneillColdwell Banker Chesapeake Real Estate Company7 sales

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Chestertown, MD real estate FAQ

How many homes are for sale in Chestertown, MD?

There are 50 homes currently for sale in Chestertown, MD.

How much do homes sell for in Chestertown, MD?

The median sale price in Chestertown, MD is $314K, based on 1,103 sales since 2020 (ranging from $120K to $950K).

How fast do homes sell in Chestertown, MD?

Homes in Chestertown, MD typically go under contract in about 17 days on market (median).

Do homes in Chestertown, MD sell above asking?

Over the past 12 months, homes in Chestertown, MD sold for an average of 97.5% of list price — below asking.

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

Homes in Chestertown, MD have sold for a median of $183 per square foot since 2020.

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

The median sale price in Chestertown, MD has risen from $256K in 2020 to $350K in 2026. At the current trend, the median is on track for roughly $412K in 2027 (modeled estimate).

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

The most active agents in Chestertown, MD over the past 18 months are: Liddy Campbell (TTR Sotheby's International Realty) — 11 sales; Retha J Arrabal (Doug Ashley Realtors, LLC) — 10 sales; Peter D Heller (Coldwell Banker Chesapeake Real Estate Company) — 7 sales.

Homes for Sale in Chestertown, MD

Newest homes for sale in Chestertown, MD

Chestertown, MD home price trend

Cost to buy in Chestertown, MD

Top agents in Chestertown, MD

Get new-listing alerts for Chestertown, MD

Chestertown, MD real estate FAQ

How many homes are for sale in Chestertown, MD?

How much do homes sell for in Chestertown, MD?

How fast do homes sell in Chestertown, MD?

Do homes in Chestertown, MD sell above asking?

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

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

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

Neighborhoods & Subdivisions in Chestertown, MD