Chestertown, MD Rental Listings

3 real estate listings match this search criteria near Chestertown.

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For Rent
11 photos
$1,300/mo
1 bd, 1 ba, 785 Sq Ft
101 Morgnec RoadChestertown, MD 21620#MDKE113944
Condominium
For Rent
7 photos
$1,495/mo
2 bd, 1 ba, 600 Sq Ft
104 Maple Avenue 3Chestertown, MD 21620#MDKE2007068
Condominium
For Rent
10 photos
$1,450/mo
1 bd, 1 ba, 900 Sq Ft
128 N Queen Street 3Chestertown, MD 21620#MDKE2006574
Single Family Residence

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Market Overview — Chestertown, MD

Showing Chestertown, MD

Property type

ResidentialCommercial

Transaction

For SaleFor Lease

Area Average

Median over the active for-sale listings

$380,000
Median Listing Price: 89
Median Days on EXIT Realty: 1,964
Median Sq Ft: $256
Median Price per Sq Ft

Compare

Compare Chestertown, MD to another area

Median price, days on market and size comparison by area
Area	Median Listing Price	Median Days on EXIT Realty	Median Sq Ft	Median Price per Sq Ft	Actions
Chestertown, MD	$380,000	89	1,964	$256

Market Composition

What's on the market

51%Residential74 active
33%Land48 active
8%Commercial11 active
3%Commercial Lease5 active
3%For Lease5 active
<1%Business1 active
<1%Farm1 active

Active listings by price

Under $200K3% · 2
$200K-$400K50% · 37
$400K-$600K14% · 10
$600K-$800K12% · 9
$800K-$1M9% · 7
Over $1M12% · 9

Median Price Trend

Jul 2026: $300,000 +13.2%Sep 2026: $339,500

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Nearby Schools

Elementary 9

HH Garnet Elementary School Pta
Chestertown, MD · 0.2 mi away
Church Hill Elementary School
Church Hill, MD · 6.4 mi away
Eastern Shore Junior Academy
Sudlersville, MD · 9.2 mi away
Rock Hall Elementary School
Rock Hall, MD · 10.4 mi away
Sudlersville Elementary School
Sudlersville, MD · 11.3 mi away
Centreville Elementary School
Centreville, MD · 11.4 mi away
Kennard Elementary School
Centreville, MD · 12.1 mi away
Millington Elementary School
Millington, MD · 12.8 mi away
Galena Elementary School
Galena, MD · 13.3 mi away

Secondary 4

Kent School
Chestertown, MD · 3.4 mi away
Kent County High School
Worton, MD · 5.2 mi away
Wye River Upper School
Centreville, MD · 11.8 mi away
Queen Anne's County High School
Centreville, MD · 12.1 mi away

Post-secondary 1

Washington College Campus Garden
Chestertown, MD · 0.3 mi away

Other schools 6

Chester River Adventist School
Chestertown, MD · 0.1 mi away
Maryland School of Sailing & Seamanship
Rock Hall, MD · 8.9 mi away
The Gunston School
Centreville, MD · 9.9 mi away
Kent County Public Schools
Rock Hall, MD · 10.4 mi away
Judy Center
Sudlersville, MD · 11.3 mi away
New Covenant Christian Academy
Queenstown, MD · 16.0 mi away

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Chestertown, MD Rental Listings

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Chestertown, MD Rental Listings

101 Morgnec RoadChestertown, MD 21620#MDKE113944

104 Maple Avenue 3Chestertown, MD 21620#MDKE2007068

128 N Queen Street 3Chestertown, MD 21620#MDKE2006574

101 Morgnec RoadChestertown, MD 21620#MDKE113944

104 Maple Avenue 3Chestertown, MD 21620#MDKE2007068

128 N Queen Street 3Chestertown, MD 21620#MDKE2006574

Market Overview — Chestertown, MD

Area Average

Compare

Market Composition

What's on the market

Active listings by price

Median Price Trend

Nearby Schools

Elementary 9

Secondary 4

Post-secondary 1

Other schools 6