How much does it cost to buy a house in Chestertown, MD?

In May 2026 Chestertown homes were listed to buy for a median price of $407K, which is a 3% decrease to April 2025 last month, and a 2% decrease to May 2025 last year. The median value of a home listed to buy in Chestertown in May 2026 was $245 per sqft, which is same as April 2025 last month, and same as May 2025 last year.

Is it affordable or expensive to live in Chestertown, MD?

It is affordable to live in Chestertown. Buying a home in Chestertown is 1% less expensive compared with the national average.

Is the Chestertown, MD housing market slowing down?

In May 2026, homes to buy in Chestertown spent an median 73 days on the market, a same May 2025 last year.

What are the best and safest places to live in Chestertown, MD?

The best and safest neighborhoods to live in Chestertown in May 2026 are Guilford, Inner Harbor, Stoneleigh, Parkside, Bolton Hill, Locust Point, Homeland, Springmill, Rodgers Forge, Canton, Charles Village, Fells Point, Hampden, Patterson Park, Cross Keys, Villa Belmont Condominiums, Wild Meadows, Cherry Hill, Waterford Trailer Park, Villagebrook Trailer Park

How much money should I make to buy a house in Chestertown, MD?

In May 2026, Chestertown homes were listed to buy for a median price of $407K, with 25% down you would need $2.3K/month to cover expenses and assume that's 35% of your total monthly income, your total yearly income would need to be $79.1K.