Chestertown

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Real Estate & Property for Sale in Chestertown

Showing 64 - 84 of 426 properties

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Pending

$867,000

25475 Turnberry Court

Chestertown MD 21620

4

4

5

Single-Family

Listing courtesy of Taylor Properties

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SoldApr 17, 2026

$495,000

Chestertown MD 21620

4

3

5

Single-Family

Listing courtesy of Cross Street Realtors LLC and Benson & Mangold, LLC

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SoldApr 17, 2026

$495,000

201 Greenwood Avenue

Chestertown MD 21620

4

3

2

Single-Family

Listing courtesy of Doug Ashley Realtors, LLC and Cross Street Realtors LLC

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SoldApr 17, 2026

$365,000

148 East Step Road

Chestertown MD 21620

4

2

4

Single-Family

Listing courtesy of Anne Arundel Properties, Inc. and Benson & Mangold, LLC

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SoldApr 17, 2026

$480,000

104 Garland Avenue

Kingstown MD 21620

3

2

2

Single-Family

Listing courtesy of Cross Street Realtors LLC

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SoldApr 17, 2026

$552,000

216 Blakefield Drive

Chestertown MD 21620

4

3

2

Single-Family

Listing courtesy of Chesapeake Real Estate Associates, LLC and Anne Arundel Properties, Inc.

Martine McGinty

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For Sale

$288,500

Butlertown MD 21678

3

1

Single-Family

Listing courtesy of Chesapeake Real Estate Associates, LLC

David Moore

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For Sale

$319,900

10584 Klamath Road

Chestertown MD 21620

3

2

Single-Family

Listing courtesy of Real Broker, LLC

Peter Heller

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For Sale

$350,000

11942 Flour Mill St

Kennedyville MD 21645

4

3

2

Single-Family

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company

Peter Heller

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For Sale

$425,000

Kennedyville MD 21645

4

3

2

Single-Family

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company

Jennifer Pogoda

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For Sale

$299,000

208 Central Drive

Kingstown MD 21620

3

1

4

Single-Family

Listing courtesy of Redfin Corp

Patricia Kern

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For Sale

$549,900

14136 Kentmore Park Road

Kennedyville MD 21645

4

2

Single-Family

Listing courtesy of Gunther-McClary Real Estate

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SoldApr 14, 2026

$220,000

513 Round Top Rd

Kingstown MD 21620

4

1

3

Single-Family

Listing courtesy of Cummings & Co. Realtors and Century 21 Don Gurney

SoldApr 13, 2026

$749,500

Chestertown MD 21620

3

3

Single-Family

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company and Cross Street Realtors LLC

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SoldApr 13, 2026

$455,000

206 Camelot Drive

Chestertown MD 21620

4

4

2

Single-Family

Listing courtesy of Chesapeake Real Estate Associates, LLC and Samson Properties

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SoldApr 10, 2026

$250,000

112 Metcalfe Road

Chestertown MD 21620

3

2

Townhouse

Listing courtesy of Rosendale Realty and Chesapeake Real Estate Associates, LLC

SoldApr 10, 2026

$332,000

23055 Old Fairlee Rd

Fairlee MD 21620

3

2

2

Single-Family

Listing courtesy of Benson & Mangold, LLC and Coldwell Banker Chesapeake Real Estate Company

5

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Under Contract

$325,000

2032 Pondtown Road

Chestertown MD 21620

3

2

8

Single-Family

Listing courtesy of Northrop Realty

SoldApr 8, 2026

$512,500

Chestertown MD 21620

4

4

2

Single-Family

Listing courtesy of Integrity Real Estate and Coldwell Banker Chesapeake Real Estate Company

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SoldApr 6, 2026

$334,000

8750 Georgetown Road

Georgetown MD 21620

3

2

9

Other

Listing courtesy of Chesapeake Real Estate Associates, LLC and EXIT Preferred Realty

Cornelia Fallon

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Pending

$369,999

720 Deep Landing Rd

Chestertown MD 21620

3

2

5

Single-Family

Listing courtesy of Coldwell Banker Waterman Realty

64 - 84 of 426

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