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Homes for Sale in Chestertown Historic District, Chestertown, MD

6 active listings · 48 sold since 2020

6

For Sale

$350K

Median Sale Price

10

Median Days on Market

97.3%

Sold-to-List

$233

Price / Sq Ft

Newest homes for sale in Chestertown Historic District, Chestertown, MD

See all 6 on the map

Chestertown Historic District, Chestertown, MD home price trend

YearMedian Sale PriceHomes Sold
2026$478K2
2025$410K5
2024$399K6
2023$402K9
2022$395K7
2021$288K8
2020$230K11

At the current trend, the median is modeled to reach about $513K in 2027 (estimate).

Cost to buy in Chestertown Historic District, Chestertown, MD

At today's ~6.63% 30-year rate, the median $350K home in Chestertown Historic District, Chestertown, MD runs about $2,260/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 Historic District, Chestertown, MD

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

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Chestertown Historic District, Chestertown, MD real estate FAQ

How many homes are for sale in Chestertown Historic District, Chestertown, MD?

There are 6 homes currently for sale in Chestertown Historic District, Chestertown, MD.

How much do homes sell for in Chestertown Historic District, Chestertown, MD?

The median sale price in Chestertown Historic District, Chestertown, MD is $350K, based on 48 sales since 2020 (ranging from $140K to $829K).

How fast do homes sell in Chestertown Historic District, Chestertown, MD?

Homes in Chestertown Historic District, Chestertown, MD typically go under contract in about 10 days on market (median).

Do homes in Chestertown Historic District, Chestertown, MD sell above asking?

Over the past 12 months, homes in Chestertown Historic District, Chestertown, MD sold for an average of 97.3% of list price — below asking.

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

Homes in Chestertown Historic District, Chestertown, MD have sold for a median of $233 per square foot since 2020.

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

The median sale price in Chestertown Historic District, Chestertown, MD has risen from $230K in 2020 to $478K in 2026. At the current trend, the median is on track for roughly $513K in 2027 (modeled estimate).

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

The most active agents in Chestertown Historic District, Chestertown, MD over the past 18 months are: Elisabeth J Ostrander (Doug Ashley Realtors, LLC) — 2 sales; John J Burke (Gunther-McClary Real Estate) — 1 sale; Tracy A Stone (Coldwell Banker Chesapeake Real Estate Company) — 1 sale.