House Prices

House Prices & Home Values Chestertown, MD 2026


Average Data

average house price$760,000
average size per house3290 ft²
average price per ft²232 $ / ft²

06/14/2026 - The value range (VR) for house prices in Chestertown, MD is $267/ sqft to $267/ sqft. An average home with 3290 sqft costs approximately $878,430 to $878,430. Chestertown, MD includes 1 ZIP codes and it is located in Kent county. The lowest prices are found in ZIP 21620, while the highest are in ZIP 21620. The average price per sqare feet is $232. Our analysis is based on 2 property listings.

Avergage prices by ZIP codes Chestertown

21620246 $ / ft²




Historical development of home values in Chestertown

Year Estimated value (USD) Change vs. 2025
2010 $352,958 -53.6%
2011 $339,309 -55.4%
2012 $338,395 -55.5%
2013 $351,044 -53.8%
2014 $368,499 -51.5%
2015 $387,412 -49.0%
2016 $407,630 -46.4%
2017 $429,631 -43.5%
2018 $453,383 -40.3%
2019 $474,406 -37.6%
2020 $498,930 -34.4%
2021 $567,480 -25.3%
2022 $661,554 -13.0%
2023 $697,639 -8.2%
2024 $737,999 -2.9%
2025 $760,000 0.0%

Graph: estimated home values in Chestertown over time (USD)



Example: 100% financing house in Chestertown

Loan amount: $760,000

Interest rate: 6.00%

Fixed monthly payment: $4,556.58

Breakdown in the 1st month:
Interest portion: $3,800.00  –  Principal portion: $756.58

Yearly breakdown (100% financing)

Year Interest per year ($) Principal per year ($) Remaining balance at year-end ($)
1 $45,346.12 $9,332.89 $750,667.11
2 $44,770.49 $9,908.52 $740,758.59
3 $44,159.35 $10,519.66 $730,238.93
4 $43,510.52 $11,168.49 $719,070.45
5 $42,821.67 $11,857.33 $707,213.11
6 $42,090.34 $12,588.67 $694,624.44
7 $41,313.90 $13,365.11 $681,259.33
8 $40,489.57 $14,189.44 $667,069.89
9 $39,614.39 $15,064.61 $652,005.28
10 $38,685.24 $15,993.77 $636,011.51
11 $37,698.78 $16,980.23 $619,031.28
12 $36,651.48 $18,027.53 $601,003.75
13 $35,539.58 $19,139.43 $581,864.32
14 $34,359.10 $20,319.91 $561,544.41
15 $33,105.81 $21,573.20 $539,971.22
16 $31,775.23 $22,903.78 $517,067.43
17 $30,362.57 $24,316.44 $492,751.00
18 $28,862.79 $25,816.22 $466,934.77
19 $27,270.50 $27,408.51 $439,526.26
20 $25,580.00 $29,099.01 $410,427.26
21 $23,785.24 $30,893.77 $379,533.48
22 $21,879.78 $32,799.23 $346,734.25
23 $19,856.79 $34,822.22 $311,912.04
24 $17,709.03 $36,969.97 $274,942.06
25 $15,428.81 $39,250.20 $235,691.86
26 $13,007.94 $41,671.07 $194,020.79
27 $10,437.76 $44,241.25 $149,779.55
28 $7,709.06 $46,969.95 $102,809.60
29 $4,812.05 $49,866.96 $52,942.64
30 $1,736.37 $52,942.64 $0.00

Note: The calculation is based on a standard annuity mortgage with a fixed monthly payment over the entire term. Extra payments, interest rate changes, and additional purchase costs (e.g. taxes, notary fees) are not included.


How to sell in Chestertown, MD


1500 sqft3900 sqft
Ø selling price$421,081$895,753
Ø fast selling$382,801$806,177
Ø high price sale$459,361$985,328

In 2026, houses in Chestertown, MD will be offered at an average price of $232 per square foot. A 1,500 sqft home priced at $421,081 is 21.14% more expensive per square foot than a 3,900 sqft home priced at $895,753. Home prices in Chestertown, MD vary significantly depending on the neighborhood and location. For a quick sale, a 2,700 sqft home should be listed at around $620,136. Sellers who can wait longer may achieve a higher price of up to $757,945.


Explore Chestertown, MD

Chestertown, Maryland is a picturesque Eastern Shore town known for its colonial streets, waterfront vistas, and welcoming community.

Historic Charm

Stroll the brick-lined Historic District where 18th-century architecture, independent shops, and galleries showcase the town?s heritage.
History lovers can visit Washington College nearby and explore museums like Sumner Hall and the Sultana Education Foundation exhibits.

Waterfront & Outdoors

The Chester River invites sailing, kayaking, and scenic cruises aboard the schooner Sultana, delivering unforgettable views of the Chesapeake Bay watershed.
Visitors enjoy riverfront parks, birding on nearby preserves, and bike routes that connect Chestertown with Kent County farms.

Arts, Culture, and Events

A vibrant arts scene thrives at the Garfield Center for the Arts and local studios, while live music and theater animate weekend nights.
Signature events like Downrigging Weekend, First Friday art walks, and the Chestertown Farmers? Market fill the calendar with family-friendly things to do.

Dining & Stays

From farm-to-table restaurants to classic seafood spots, Chestertown dining celebrates fresh oysters, crab, and seasonal produce.
Charming bed-and-breakfasts and boutique inns offer walkable access to the waterfront, shopping, and the Washington College campus.

Plan Your Visit

Plan your Chestertown, MD getaway to experience small-town comfort, historic authenticity, and outdoor adventures on the beautiful Chester River.



FAQ – Home Values in Chestertown

What is the median home value in Chestertown in 2026?

In 2026, the typical home value in Chestertown is about $760,000 for an average home size of 3290 square feet. This corresponds to an average price of roughly $232 per square foot.

What is the average cost per square foot in Chestertown?

In 2026, homes in Chestertown sell for an average of around $232 per square foot, with a typical range between $267 and $267 per square foot, depending on the property’s location, condition, and lot size.

What is the average home size in ?

The average home size in Chestertown is about 3290 square feet, with an estimated 2026 value around $760,000.



Locations close to Chestertown, MD

Church Creek, MD248 $ / ft²
Church Hill, MD236 $ / ft²
Claiborne, MD304 $ / ft²
Chester, MD256 $ / ft²
Centreville, MD287 $ / ft²
Cambridge, MD265 $ / ft²
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