21620, MD homes for sale & real estate

2 days on Rocket

$2,909 Closing Credit¹

$245,000

3 beds • 1 bath • 1,000 sqft

10624 Millbrook Dr, Chestertown, MD 21620

#MDKE2005398, Kristina L Hyland, Listing office: Coldwell Banker Chesapeake Real Estate Company

Coming soon

$7,897 Closing Credit¹

$665,000

4 beds • 3 baths • 2,544 sqft

7071 Pomona Rd, Chestertown, MD 21620

#MDKE2005364, Liddy Campbell, Listing office: TTR Sotheby's International Realty

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

3 days on Rocket

$2,078 Closing Credit¹

$175,000

2 beds • 1.5 baths • 1,160 sqft

23069 Raleigh Rd, Chestertown, MD 21620

#MDKE2005378, George C McDowell III, Listing office: Keller Williams Select Realtors of Annapolis

5 days on Rocket

$9,464 Closing Credit¹

$797,000

3 beds • 2.5 baths • 2,522 sqft

7514 Muirfield Dr, Chestertown, MD 21620

#MDKE2005370, John J Burke, Listing office: Gunther-McClary Real Estate

Coming soon

$10,000 Closing Credit¹

$975,000

4 beds • 3 baths • 3,401 sqft

10715 Kasota Rd, Chestertown, MD 21620

#MDKE2005366, Sarah E. King, Listing office: Cross Street Realtors LLC

Coming soon

$8,301 Closing Credit¹

$699,000

4 beds • 3.5 baths • 2,008 sqft

206 S Water St, Chestertown, MD 21620

#MDKE2005362, Elisabeth J Ostrander, Listing office: Doug Ashley Realtors, LLC

$2,316 Closing Credit¹

$195,000

2 beds • 1 bath • 1,269 sqft

21317 Persimmon Dr, Chestertown, MD 21620

#MDKE2005356, Michele A Palmer, Listing office: Doug Ashley Realtors, LLC

Room to negotiate?

Median List Price

$427K

Avg. Sale Time

93 Days

Based on our May 2025 Market Report.

$4,749 Closing Credit¹

$399,900

4 beds • 3 baths • 2,106 sqft

10705 Millbrook Dr, Chestertown, MD 21620

#MDKE2005354, Adam J Murphy, Listing office: RE/MAX Realty Centre, Inc.

$3,978 Closing Credit¹

$335,000

3 beds • 2.5 baths • 1,500 sqft

10578 Tonopah Rd, Chestertown, MD 21620

#MDKE2005352, David J. J Moore, Listing office: RE/MAX Executive

$10,000 Closing Credit¹

$1,297,000

5 beds • 3.5 baths • 3,640 sqft

300 Hickory Ln, Chestertown, MD 21620

#MDQA2013388, John J Burke, Listing office: Gunther-McClary Real Estate

$5,819 Closing Credit¹

$490,000

3 beds • 2 baths • 1,820 sqft

206 Barroll Dr, Chestertown, MD 21620

#MDKE2005094, Joelle Dolch, Listing office: Cross Street Realtors LLC

$19,000

Land • 0.34 Acres

Lenapah Rd, Chestertown, MD 21620

#MDKE2005184, Michael H Bennett, Listing office: Compass

$3,563 Closing Credit¹

$300,000

3 beds • 1 bath • 1,056 sqft

925 Round Top Rd, Chestertown, MD 21620

#MDQA2013044, Liddy Campbell, Listing office: TTR Sotheby's International Realty

$2,850 Closing Credit¹

$240,000

2 beds • 1 bath • 1,290 sqft

624 High St, Chestertown, MD 21620

#MDKE2005274, Nicole Stephens, Listing office: Tesla Realty Group, LLC

$949 Closing Credit¹

$79,900

2 beds • 1 bath • 910 sqft

132 Prospect St, Chestertown, MD 21620

#MDKE2005276, Ana Lucia Ron, Listing office: ANR Realty, LLC

Backup offers

$3,491 Closing Credit¹

$294,000

3 beds • 1 bath • 1,104 sqft

212 Central Dr, Chestertown, MD 21620

#MDQA2013564, Lisa P Raffetto, Listing office: Coldwell Banker Chesapeake Real Estate Company

Backup offers

$3,088 Closing Credit¹

$260,000

2 beds • 2 baths • 1,384 sqft

898 Washington Ave, Chestertown, MD 21620

#MDKE2005250, Douglas J Ashley, Listing office: Doug Ashley Realtors, LLC

Backup offers

$3,561 Closing Credit¹

$299,900

3 beds • 1.5 baths • 896 sqft

21363 Indiana Ave, Chestertown, MD 21620

#MDKE2005264, Courtney Chipouras, Listing office: TTR Sotheby's International Realty

$12,000

Land • 0.34 Acres

Buck Neck Rd, Chestertown, MD 21620

#MDKE2005262, Maryn J. LeClair, Listing office: Chesapeake Real Estate Associates, LLC

$12,000

Land • 0.34 Acres

Kinglet Rd, Chestertown, MD 21620

#MDKE2005260, Maryn J. LeClair, Listing office: Chesapeake Real Estate Associates, LLC

$4,453 Closing Credit¹

$375,000

3 beds • 2.5 baths • 2,294 sqft

24607 Chestertown Rd, Chestertown, MD 21620

#MDKE2005240, William Sutton, Listing office: Coldwell Banker Chesapeake Real Estate Company

$5,344 Closing Credit¹

$450,000

3 beds • 2 baths • 1,788 sqft

22570 Bay Shore Rd, Chestertown, MD 21620

#MDKE2005230, Joseph S. Ciganek, Listing office: Coldwell Banker Chesapeake Real Estate Company

$115,000

Land • 0.48 Acres

E St, Chestertown, MD 21620

#MDQA2013494, Michael ONeill, Listing office: Coldwell Banker Chesapeake Real Estate Company

$10,000 Closing Credit¹

$1,495,000

3 beds • 3.5 baths • 3,789 sqft

26875 Mallard Rd, Chestertown, MD 21620

#MDKE2005186, Lynn M Hilfiker, Listing office: Gunther-McClary Real Estate

$90,000

Land • 3 Acres

Georgetown Rd, Chestertown, MD 21620

#MDKE2005218, Retha J Arrabal, Listing office: Doug Ashley Realtors, LLC

Tour

$575,000

Land • 3.01 Acres

136 Truslow Farm Ln, Chestertown, MD 21620

#MDQA2013478, Maryn J. LeClair, Listing office: Chesapeake Real Estate Associates, LLC

Backup offers

$3,741 Closing Credit¹

$315,000

3 beds • 2 baths • 1,404 sqft

10670 Tintah Rd, Chestertown, MD 21620

#MDKE2005200, Bronwyn C Scott, Listing office: Samson Properties

$85,000

Land • 2.20 Acres

Fairlee Rd, Chestertown, MD 21620

#MDKE2005204, Lori A Sample, Listing office: EXIT Preferred Realty

Backup offers

$2,434 Closing Credit¹

$205,000

3 beds • 2.5 baths • 1,216 sqft

310 Hilltop Ln, Chestertown, MD 21620

#MDKE2005194, Richard C Evans, Listing office: Cross Street Realtors LLC

Backup offers

$4,691 Closing Credit¹

$395,000

2 beds • 2 baths • 1,080 sqft

420 Cannon St, Chestertown, MD 21620

#MDKE2005174, Elisabeth J Ostrander, Listing office: Doug Ashley Realtors, LLC

$3,000,000

Land • 87.34 Acres

Cromwell Clark Rd, Chestertown, MD 21620

#MDKE2005156, BRIAN MORRIS, Listing office: The Land Group

Backup offers

$75,000

Land • 2.36 Acres

9020 Georgetown Rd, Chestertown, MD 21620

#MDKE2005152, Jennifer L Mobley, Listing office: Coldwell Banker Chesapeake Real Estate Company

$2,529 Closing Credit¹

$213,000

1 bed • 1 bath • 900 sqft

236 Merganser Dr, Chestertown, MD 21620

#MDQA2013084, Dana M Byrd, Listing office: Thurston Wyatt Real Estate, LLC

$10,000 Closing Credit¹

$1,550,000

3 beds • 3.5 baths • 2,699 sqft

21082 Wyoming Ave, Chestertown, MD 21620

#MDKE2005016, Retha J Arrabal, Listing office: Doug Ashley Realtors, LLC

$150,000

Land • 2 Acres

Caulks Field Rd, Chestertown, MD 21620

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

$150,000

Land • 2 Acres

Georgetown Rd SE, Chestertown, MD 21620

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

$15,000

Land • 0.69 Acres

23683 L Rd, Chestertown, MD 21620

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

$4,976 Closing Credit¹

$419,000

2 beds • 2 baths • 1,496 sqft

114 Ryan Ct, Chestertown, MD 21620

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

$9,488 Closing Credit¹

$799,000

2 beds • 2 baths • 1,966 sqft

26889 Morgnec Rd, Chestertown, MD 21620

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

$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

21620, MD Real Estate Market Overview

There are 90 homes for sale in 21620, MD. The following market insights reflect all property types in the 21620, MD real estate market. The inventory of homes for sale in 21620, MD between April 2025 and May 2025 increased by 52.2%. Listings spent 93 days on the market in May 2025, and had a median list price of $427,000 during the same period.

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

What is it like to live in 21620, MD

Overview

21620 is located in Maryland. There are roughly 12,762 residents, living in 5,028 households. The average temperature for 21620 this time of the year is low of 62F and high of 83F. On average, 21620 gets about 3.78 inches of precipitation in June. Most residents are home owners (67%), have a post secondary degree (44%) and are single, no kids (43%).

Data provided by Home Junction

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

Explore popular home types in 21620, MD

Related homes in 21620, MD

Schools near 21620, MD

Housing market reports in Kent County

Homes for sale near 21620, MD

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