The story of this market
The typical home in Chestertown, Maryland sells for about $455,000, or $241 per square foot.
Prices are up +29% from a year ago, so sellers still have some momentum. Homes take about 67 days to sell, which is slow. HUD's fair market rent for a two-bedroom is $1,750 a month.
Monthly price momentum
Home values since 2015
+1.1%
MD · past 12 months
Freddie Mac House Price Index, single-family homes, monthly through 2026-08. Each line starts at 100 in January 2015, so a reading of 180 means prices are up 80% since then.
Chestertown, Maryland
Chestertown's housing market shows significant price appreciation over the last year, driven by limited inventory and steady demand. While the town remains fiscally sound with active residential development, the market is currently characterized by a low volume of sales and a competitive environment for available listings.
No ARED county foreclosure postings attributed to Chestertown yet — the verified ledger covers every county the foreclosure ingest has read, attributed by published city area. Key-figure check: median price corroborated by the prior refresh cycle (within 12.5%).
Deterministic aggregate of 1 researched ZIP reports — sales_count-weighted (population fallback); per point, children lacking the value or its weight are excluded. Tax rates, sentiment and context notes are tier-native and never roll.
Median prices moved up 2.3% year over year.
Homes spend a median of 68 days on market with 0.0 months of supply — a balanced-paced market.
0% of listings have cut prices · homes sell at 0% of asking — demand is holding steady.
no recorded foreclosure-ledger notices (0.0 per 10,000 residents) · unemployment 3.8% · poverty 11.6% — a stable, low-distress profile.
The amenity base that shapes daily life and property demand in this city — what residents actually live with, and what the pipeline is adding.
The river serves as a central anchor for the town, providing boating, fishing, and scenic views that enhance property desirability.
A well-preserved district featuring local boutiques, restaurants, and cultural venues that drive local tourism and resident activity.
Chestertown is well-suited for families and those seeking a historic, small-town lifestyle with waterfront access, while also attracting investors interested in the town's steady development pipeline.
The area is served by Kent County Public Schools, which provides a standard public education curriculum for the region.
Transportation is primarily road-based, with the town serving as a regional hub for Kent County; car ownership is common but lower than the national average.
Chestertown offers a rich amenity base centered on its historic waterfront, featuring parks, walking trails, and a vibrant downtown district with local shopping and dining.
The rental market shows moderate depth with a median rent of $1,750; vacancy pressure remains balanced, though inventory is limited.
The local economy is anchored by municipal services, education, and a growing residential development sector, with a focus on maintaining fiscal stability.
The town is experiencing moderate development momentum with residential projects like Radcliffe Meadow and Chestertown Arms II, supported by local planning efforts to manage growth while preserving historic character.
The Planning Commission is actively working with the Eastern Shore Land Conservancy on comprehensive rezoning to guide future residential and commercial growth.
Parcels are subject to municipal and county-level taxation, with specific oversight from the Historic District Commission for properties within designated zones.
As a historic riverfront town, Chestertown faces localized flood risks near the Chester River, requiring residents to monitor flood zone designations for insurance purposes.
Composed from the ARED governance burden registry — tier-native tax structure (state + county + city + special districts), never averaged. State (Maryland) — Maryland Real Property Assessment and Taxation: Property is assessed at its phased-in use value. The tax is calculated by multiplying the assessed value by the applicable state and local tax rates.
Researched annual trajectory for this city, from published historical series
Solid: researched ten-year history · dotted: 1 / 3 / 5-year projection extended from the historical 0.0%/yr trend — a deterministic estimate, not a published forecast or guarantee.
Median annual property tax paid on this city's residential parcels
Solid: researched ten-year history · dotted: 1 / 3 / 5-year projection extended from the historical 4.7%/yr trend — a deterministic estimate, not a published forecast or guarantee.
Data retrieved from U.S. Census Bureau QuickFacts and Data USA profiles.
No public schools report a street address in this area. Source: NCES EDGE public school locations 2023-24.