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Chestertown, MD
Map
128 Properties Available

128 Properties Available

The average price in the selected areas has remained stable. Learn more
  • Newest Listings
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  • Price-Low To High
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
118 LITTLE HARBOR WAY #202, Chestertown, MD 21620
1/19
Coming Soon

$695,000

3 Beds2 Baths1,600 SqFt

118 LITTLE HARBOR WAY #202, Chestertown, MD 21620

MLS# MDKE2005800

Listed by Benson & Mangold, LLC

Bright MLS (BMLS)
8833 GEORGETOWN RD, Chestertown, MD 21620
1/47
Active

$364,000

4 Beds2 Baths1,625 SqFt

8833 GEORGETOWN RD, Chestertown, MD 21620

MLS# MDKE2005766

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
CLARISSA RD, Chestertown, MD 21620
Active

$10,000

0.34 Acres

CLARISSA RD, Chestertown, MD 21620

MLS# MDKE2005786

Listed by Samson Properties

Bright MLS (BMLS)
404 SPRING RD, Chestertown, MD 21620
1/11
Under Contract

$19,500

0.99 Acres

404 SPRING RD, Chestertown, MD 21620

MLS# MDQA2014990

Listed by The Parker Group

Bright MLS (BMLS)
423 CALVERT ST, Chestertown, MD 21620
1/20
Price Dropped by $30K
3D

$135,000

3 Beds2 Baths1,136 SqFt

423 CALVERT ST, Chestertown, MD 21620

MLS# MDKE2005718

Listed by Redfin Corp

Bright MLS (BMLS)
7653 BROAD NECK RD, Chestertown, MD 21620
1/39
Under Contract

$375,000

4 Beds3 Baths1,790 SqFt

7653 BROAD NECK RD, Chestertown, MD 21620

MLS# MDKE2005742

Listed by Benson & Mangold, LLC

Bright MLS (BMLS)
517 HIGH ST, Chestertown, MD 21620
1/51
Pending

$389,900

1,728 SqFt

517 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005736

Listed by L. C. Parker Real Estate

Bright MLS (BMLS)
100 ADELA WAY, Chestertown, MD 21620
1/71
Active

$515,000

4 Beds4 Baths3,799 SqFt

100 ADELA WAY, Chestertown, MD 21620

MLS# MDKE2005636

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
103 METCALF RD, Chestertown, MD 21620
1/25
Active

$259,900

3 Beds2 Baths1,280 SqFt

103 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005688

Listed by Real Broker, LLC

Bright MLS (BMLS)
23110 OLD FAIRLEE RD, Chestertown, MD 21620
1/29
Price Dropped by $10K

$349,900

3 Beds1 Bath1,805 SqFt

23110 OLD FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2005676

Listed by Real Broker LLC

Bright MLS (BMLS)
7989 QUAKER NECK RD, Chestertown, MD 21620
1/90
Price Dropped by $250K
3D

$2,500,000

5 Beds5 Baths4,305 SqFt

7989 QUAKER NECK RD, Chestertown, MD 21620

MLS# MDKE2005590

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
103 LANDING LN, Chestertown, MD 21620
1/69
Price Dropped by $19K

$539,999

2 Beds3 Baths2,100 SqFt

103 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005670

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
100 METCALF RD, Chestertown, MD 21620
1/16
Price Dropped by $5K

$245,000

3 Beds2 Baths1,140 SqFt

100 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005634

Listed by Bayside Realty

Bright MLS (BMLS)
21316 PERSIMMON DR, Chestertown, MD 21620
1/21
Active

$179,000

2 Beds1 Bath1,232 SqFt

21316 PERSIMMON DR, Chestertown, MD 21620

MLS# MDKE2005624

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
10751 MILLBROOK DR, Chestertown, MD 21620
1/50
Under Contract

$350,000

3 Beds2 Baths1,942 SqFt

10751 MILLBROOK DR, Chestertown, MD 21620

MLS# MDKE2005652

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
23043 BAY SHORE SPUR, Chestertown, MD 21620
1/27
Price Dropped by $25K

$325,000

4 Beds3 Baths2,630 SqFt

23043 BAY SHORE SPUR, Chestertown, MD 21620

MLS# MDKE2005584

Listed by Rock Hall Properties Real Estate

Bright MLS (BMLS)
116 HARLAN LOOP, Chestertown, MD 21620
1/21
Active

$519,000

5 Beds4 Baths4,067 SqFt

116 HARLAN LOOP, Chestertown, MD 21620

MLS# MDKE2005610

Listed by Samson Properties

Bright MLS (BMLS)
200 WASHINGTON AVE, Chestertown, MD 21620
1/35
Under Contract

$695,000

4 Beds4 Baths2,917 SqFt

200 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2005538

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
302 PARK ROW #OFFICE 2, Chestertown, MD 21620
1/6
Active

$600

302 PARK ROW #OFFICE 2, Chestertown, MD 21620

MLS# MDKE2005598

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
BUCK NECK LANDING RD, Chestertown, MD 21620
1/2
Active

$10,000

0.55 Acres

BUCK NECK LANDING RD, Chestertown, MD 21620

MLS# MDKE2005586

Listed by Rosendale Realty

Bright MLS (BMLS)
TONOPAH RD., Chestertown, MD 21620
1/2
Active

$40,000

0.34 Acres

TONOPAH RD., Chestertown, MD 21620

MLS# MDKE2005564

Listed by The Hogans Agency

Bright MLS (BMLS)
5700 JOHNSONTOWN RD, Chestertown, MD 21620
1/7
Pending

$110,000

3 Beds1 Bath1,144 SqFt

5700 JOHNSONTOWN RD, Chestertown, MD 21620

MLS# MDKE2005562

Listed by Tesla Realty Group, LLC

Bright MLS (BMLS)
JOHNSONTOWN RD, Chestertown, MD 21620
1/16
Under Contract

$35,000

0.9 Acres

JOHNSONTOWN RD, Chestertown, MD 21620

MLS# MDKE2005550

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
112 METCALF RD, Chestertown, MD 21620
1/20
Active

$249,950

3 Beds2 Baths1,280 SqFt

112 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005498

Listed by Engel & Volkers Annapolis

Bright MLS (BMLS)
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Keller Williams Gateway

Andrew Johns

+1(410) 627-7264 andrew@andrewjohnshometeam.com

8015 Corporate Drive, Ste C, Nottingham, Maryland, 21236, United States

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AJHT - Logo with KW - over black-01
Keller Williams Gateway

Andrew Johns

+1(410) 627-7264 andrew@andrewjohnshometeam.com

8015 Corporate Drive, Ste C, Nottingham, Maryland, 21236, United States

    • Home
      About
      1. About Us
      Schedule Now
      Blogs
    • Buy
      1. Buyers Guide
      2. Find Your Home
      3. Luxury Listings
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      Communities
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      4. Cecil County
      Contact Us
    • Sell
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      2. Sell My Home
      3. Home Valuation
      4. Sold Listings
      Discover
      1. Market Snapshot
      Join our Team

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.