21620, MD homes for sale & real estate

9 hours on Rocket

$150,000

Land • 2 Acres

Caulks Field Rd, Chestertown, MD 21620

#MDKE2005120, Sebrin Adem, Listing Office: RE/MAX Allegiance

Coming soon

$8,847 Closing Credit¹

$745,000

4 beds • 3 baths • 3,166 sqft

9050 Point Ln, Chestertown, MD 21620

#MDKE2005102, Terri L Kulp, Listing Office: Coldwell Banker Chesapeake Real Estate Company

Save big

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Coming soon

$6,282 Closing Credit¹

$529,000

4 beds • 2 baths • 3,050 sqft

107 N Queen St, Chestertown, MD 21620

#MDKE2005108, Elisabeth J Ostrander, Listing Office: Doug Ashley Realtors, LLC

2 days on Rocket

$3,705 Closing Credit¹

$312,000

3 beds • 2 baths • 1,188 sqft

104 Dutchess Rd, Chestertown, MD 21620

#MDQA2013072, Helen J Butler, Listing Office: Taylor Properties

view of front of house with brick siding, a front lawn, and driveway

Coming soon

$6,234 Closing Credit¹

$525,000

4 beds • 2.5 baths • 4,086 sqft

325 Devon Dr, Chestertown, MD 21620

#MDKE2005100, LISA GAMBINO LESCALLEET, Listing Office: Berkshire Hathaway HomeServices PenFed Realty

3 days on Rocket

$150,000

Land • 2 Acres

Georgetown Rd SE, Chestertown, MD 21620

#MDKE2005076, Sebrin Adem, Listing Office: RE/MAX Allegiance

4 days on Rocket

$1,186 Closing Credit¹

$99,900

2 beds • 1 bath • 910 sqft

132 Prospect St, Chestertown, MD 21620

#MDKE2005084, Ana Lucia Ron, Listing Office: ANR Realty, LLC

Room to negotiate?

Median Sold Price

$369.5K

Avg. Sale Time

55 Days

Based on our March 2025 Market Report.

5 days on Rocket

$6,519 Closing Credit¹

$549,000

3 beds • 2 baths • 1,961 sqft

101 Birch Run Rd, Chestertown, MD 21620

#MDKE2005088, Stacy L. Kendall, Listing Office: Cross Street Realtors LLC

Backup offers

$7,124 Closing Credit¹

$599,900

5 beds • 2.5 baths • 2,536 sqft

108 N Queen St, Chestertown, MD 21620

#MDKE2004886, Peter D Heller, Listing Office: Coldwell Banker Chesapeake Real Estate Company

$6,828 Closing Credit¹

$575,000

3 beds • 2.5 baths • 2,010 sqft

25285 Foxchase Dr, Chestertown, MD 21620

#MDKE2005078, Mary C Carlisle, Listing Office: Coldwell Banker Chesapeake Real Estate Company

$8,609 Closing Credit¹

$725,000

2 beds • 2.5 baths • 2,204 sqft

100 Little Harbor Way, Chestertown, MD 21620

#MDKE2005040, Jeannette A Westcott, Listing Office: Keller Williams Realty Centre

chalet / cabin with fence private yard and a shingled roof

Coming soon

$2,613 Closing Credit¹

$220,000

1 bed • 1 bath • 882 sqft

619 Cannon St, Chestertown, MD 21620

#MDKE2005050, Sarah E. King, Listing Office: Cross Street Realtors LLC

$15,000

Land • 0.69 Acres

23683 L Rd, Chestertown, MD 21620

#MDKE2005072, Alyson Anderson I, Listing Office: Allfirst Realty, Inc.

Iowa Ave, Chestertown MD, 21620 land for sale

$10,000

Land • 0.73 Acres

Iowa Ave, Chestertown, MD 21620

#MDKE2005066, John T Carroll, Listing Office: Village Real Estate Company LLC

$5,451 Closing Credit¹

$459,000

2 beds • 2 baths • 1,496 sqft

114 Ryan Ct, Chestertown, MD 21620

#MDQA2012972, Julie H SANTOBONI, Listing Office: Taylor Properties

$10,000 Closing Credit¹

$865,000

2 beds • 2 baths • 1,966 sqft

26889 Morgnec Rd, Chestertown, MD 21620

#MDKE2005060, Michael ONeill, Listing Office: Coldwell Banker Chesapeake Real Estate Company

Backup offers

$8,905 Closing Credit¹

$749,900

5 beds • 3 baths • 3,394 sqft

7988 Aldan Dr, Chestertown, MD 21620

#MDKE2004966, Douglas J Ashley, Listing Office: Doug Ashley Realtors, LLC

$7,707 Closing Credit¹

$649,000

3 beds • 2.5 baths • 2,296 sqft

129 N Queen St N, Chestertown, MD 21620

#MDKE2004970, William H Norris III, Listing Office: Select Land & Homes, LLC

Backup offers

$9,441 Closing Credit¹

$795,000

4 beds • 4 baths • 4,401 sqft

211 David Dr, Chestertown, MD 21620

#MDKE2005038, Michael ONeill, Listing Office: Coldwell Banker Chesapeake Real Estate Company

$10,000 Closing Credit¹

$1,459,000

3 beds • 2.5 baths • 2,315 sqft

Little Harbor Way Unit 1, Chestertown, MD 21620

#MDKE2004992, John J Burke, Listing Office: Gunther-McClary Real Estate

$6,886 Closing Credit¹

$579,900

1 bath • 1,148 sqft

5179 Quaker Neck Rd, Chestertown, MD 21620

#MDKE2005028, Jonathan C Taylor, Listing Office: Hyatt & Company Real Estate, LLC

$3,966 Closing Credit¹

$334,000

3 beds • 1 bath • 1,104 sqft

24095 Chestertown Rd, Chestertown, MD 21620

#MDKE2005020, Lona Sue Todd, Listing Office: Taylor Properties

$4,333 Closing Credit¹

$364,900

3 beds • 2.5 baths • 1,724 sqft

216 Silver Heel Rd, Chestertown, MD 21620

#MDKE2005024, Cynthia F Gardner, Listing Office: CENTURY 21 New Millennium

$3,443 Closing Credit¹

$289,900

3 beds • 1 bath • 1,056 sqft

114 Darden Rd, Chestertown, MD 21620

#MDQA2012808, Lee F. Wolff, Listing Office: FSBO Broker

$10,000 Closing Credit¹

$1,200,000

5 beds • 5 baths • 3,078 sqft

22153 1st Point Rd, Chestertown, MD 21620

#MDKE2004460, Liddy Campbell, Listing Office: TTR Sotheby's International Realty

$2,791 Closing Credit¹

$235,000

3 beds • 2.5 baths • 1,200 sqft

300 Hilltop Ln, Chestertown, MD 21620

#MDKE2005004, William Sutton, Listing Office: Coldwell Banker Chesapeake Real Estate Company

$35,000

Land • 0.34 Acres

Cogar Rd, Chestertown, MD 21620

#MDKE2004996, Michael H Bennett, Listing Office: Compass

$35,000

Land • 0.34 Acres

Tonopah Rd, Chestertown, MD 21620

#MDKE2004994, Michael H Bennett, Listing Office: Compass

$10,000 Closing Credit¹

$1,395,000

5 beds • 4.5 baths • 3,243 sqft

105 High St, Chestertown, MD 21620

#MDKE2005002, Michael ONeill, Listing Office: Coldwell Banker Chesapeake Real Estate Company

$2,374 Closing Credit¹

$199,900

2 beds • 1 bath • 896 sqft

110 Philosophers Ter, Chestertown, MD 21620

#MDKE2004982, Debra B Meikle, Listing Office: Doug Ashley Realtors, LLC

$6,876 Closing Credit¹

$579,000

2 beds • 2.5 baths • 2,100 sqft

103 Landing Ln, Chestertown, MD 21620

#MDKE2004972, John J Burke, Listing Office: Gunther-McClary Real Estate

Backup offers

$5,759 Closing Credit¹

$485,000

2 beds • 2.5 baths • 1,476 sqft

101 S Mill St, Chestertown, MD 21620

#MDKE2004984, Michael ONeill, Listing Office: Coldwell Banker Chesapeake Real Estate Company

Old Morgnec Rd, Chestertown MD, 21620 land for sale

$64,000

Land • 1.37 Acres

Old Morgnec Rd, Chestertown, MD 21620

#MDKE2004974, Kristina L Hyland, Listing Office: Coldwell Banker Chesapeake Real Estate Company

$3,788 Closing Credit¹

$319,000

4 beds • 2 baths • 1,404 sqft

306 Cedar St, Chestertown, MD 21620

#MDKE2004954, Douglas J Ashley, Listing Office: Doug Ashley Realtors, LLC

$49,900

Land • 1.51 Acres

Cloquet Rd, Chestertown, MD 21620

#MDKE2004960, Rebecca M Schor, Listing Office: Berkshire Hathaway HomeServices Homesale Realty

$6,116 Closing Credit¹

$515,000

4 beds • 3.5 baths • 3,420 sqft

314 Devon Dr, Chestertown, MD 21620

#MDKE2004946, Heather Branham, Listing Office: The Parker Group

Backup offers

$3,438 Closing Credit¹

$289,500

2 beds • 3 baths • 1,867 sqft

116 Oak Leaf Dr, Chestertown, MD 21620

#MDKE2004942, Grace M Crockett, Listing Office: Doug Ashley Realtors, LLC

$250,000

Land • 0.93 Acres

Scheeler Rd, Chestertown, MD 21620

#MDKE2004650, William H Norris III, Listing Office: Select Land & Homes, LLC

$10,000 Closing Credit¹

$998,000

3 beds • 3.5 baths

226 S Water St, Chestertown, MD 21620

#MDKE2004940, John J Burke, Listing Office: Gunther-McClary Real Estate

Backup offers

$9,369 Closing Credit¹

$789,000

3 beds • 2.5 baths • 2,204 sqft

308 Landing Ln, Chestertown, MD 21620

#MDKE2004928, John J Burke, Listing Office: Gunther-McClary Real Estate

21620, MD Real Estate Market Overview

Browse 93 homes for sale in 21620, MD. View properties, photos, nearby real estate with school and housing market information. In March 2025 in 21620, MD there were 38% more homes for sale than in February 2025. Listings spent 55 days on the market in March 2025, and had a median list price of $369,500 during the same period. 21620, MD housing market in March 2025 saw over 3 listings sold above listed price, more than 3 sold at listed price and over 7 sold below.

From Rocket Homes Real Estate and based on county public records data

Schools near 21620, MD

Elementary Schools

Church Hill Elementary School
631 Main St
Public District PK-4
Henry Highland Garnet Elementary School
320 Calvert St
Public District PK-5
Rock Hall Elementary School
21203 W Sharp St
Public District PK-5

Middle Schools

Kent County Middle School
402 E Campus Ave
Public District 6-8

High Schools

Kent County High School
25301 Lambs Meadow Rd
Public District 9-12

Data provided by Great Schools

Homes for sale in 21620, MD

21620, MD Real Estate Market Overview

What is it like to live in 21620, MD

Overview

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Homes for sale near 21620, MD

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