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Townhome Foreclosures in Chestertown, MD

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Chestertown, MD Foreclosures

Current Market Conditions in in Chestertown, MD As of April 2026?
In the past month, Chestertown's real estate market has remained competitive, with a slight uptick in inventory levels ensuring more choices for potential buyers. Homes are spending an average of 30 days on the market, which is slightly lower than previous months, indicating strong buyer interest. However, prices have stabilized rather than increased sharply, reflecting a balanced market approach.
How much do homes sell for in Chestertown, MD?
The average home price is currently $488,513.
What’s the average rental cost in Chestertown, MD?
The average rental price in Chestertown is $1,367.
What is the most expensive home in Chestertown?
The most expensive home sold in Chestertown had a price of $14,159,679.
What is currently the cheapest priced home in Chestertown, MD?
The cheapest home for sale in Chestertown is priced at $10,144.

Living in Chestertown, MD

Chestertown, MD is a charming historical town with a vibrant cultural scene and a picturesque waterfront. Known for its well-preserved colonial architecture, it offers a blend of history and modern amenities, making it an ideal place for families and retirees alike. The community boasts ample outdoor activities and a tight-knit community feel, complemented by reputable local schools.

Buyer vs Seller Market in Chestertown, MD

The real estate market in Chestertown remains stable, with a mix of historic homes and new constructions appealing to a variety of buyers. Demand is strong particularly among those looking for vacation homes or retirement properties due to the town's serene environment and artistic flair. Prices have shown modest increases, reflecting the desirability of the area.

Current trends reveal that Chestertown is becoming increasingly attractive to home buyers from surrounding metropolitan areas, seeking more affordable options amidst increasing urban prices. The community’s charm, coupled with improvements in local amenities and infrastructure, continues to drive interest and growth in the market.

Home Value Estimator For Chestertown, MD

There are currently 5,867 real estate properties in Chestertown, MD, with a median automated valuation model (AVM) price of $352,296.00. What is an AVM? It is a smart computer program that analyzes and predicts the approximate value of a home, property or land in Chestertown, MD, based on current market trends, comparable real estate sales nearby, historical data and, of course, property features, among other variables. These automated home estimates are often very helpful, providing buyers and sellers with a better idea of a home’s value ahead of the negotiation process. For example, the average home price in Chestertown, MD, is $488,513.00, with the most expensive house in Chestertown, MD, topping out at $14,159,679.00 and the cheapest home in Chestertown, MD, clocking in at $10,144.00. In other words, there’s something for every potential homebuyer or savvy investor in Chestertown, MD!

Rent Prices In Chestertown, MD

With the expiration of certain local, state and federal housing-related restrictions and mandated programs, the rental market in Chestertown, MD, is on a rollercoaster ride. The average rent price in Chestertown, MD, is $1,367.00. Indeed, when looking to rent in Chestertown, MD, you can expect to pay as little as $780.00 or as much as $2,850.00, with the average rent median estimated to be $1,320.00. The good news is that finding an affordable and desirable property to rent in Chestertown, MD -- whether it’s apartments, townhomes, condominiums or single-family homes -- is made easier with knowledge of the local market and, of course, a little patience.

Chestertown, MD Townhomes


Market Trend for Chestertown, MD

Total Listings Available: 0

Market Values:

Home Prices from $10,144 to $14,159,679

Average Sales Price: $488,513

Rental Values:

Rental from $780 to $2,850

Average Rent Value: $1,367 / month

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