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100 Properties
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100 Properties Available In Chestertown

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MD >Chestertown >
Market Insights
105 HIGH ST, Chestertown, MD 21620
Active

$1,395,500

105 HIGH ST, Chestertown, MD 21620

5 Beds5 Baths3,243 SqFt

MLS# MDKE2005002

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
103 LANDING LN, Chestertown, MD 21620
Active

$569,000

103 LANDING LN, Chestertown, MD 21620

2 Beds3 Baths2,100 SqFt

MLS# MDKE2004972

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
128 EDMORE RD, Chestertown, MD 21620
Active

$425,000

128 EDMORE RD, Chestertown, MD 21620

4 Beds2 Baths2,568 SqFt

MLS# MDQA2012546

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
226 S WATER ST, Chestertown, MD 21620
Active

$998,000

226 S WATER ST, Chestertown, MD 21620

3 Beds4 Baths3,782 Sqft Lot

MLS# MDKE2004940

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
21217 TEXAS AVE, Chestertown, MD 21620
Price Dropped by $17K

$232,000

21217 TEXAS AVE, Chestertown, MD 21620

2 Beds1 Bath912 SqFt

MLS# MDKE2004902

Listed by RE/MAX Leading Edge

Bright MLS (BMLS)
212 LANDING LN, Chestertown, MD 21620
Active

$759,000

212 LANDING LN, Chestertown, MD 21620

3 Beds4 Baths

MLS# MDKE2004782

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
109 WILTON RD, Chestertown, MD 21620
Active

$349,900

109 WILTON RD, Chestertown, MD 21620

3 Beds2 Baths1,392 SqFt

MLS# MDQA2011782

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
11040 KYLIE LN, Chestertown, MD 21620
Price Dropped by $20K

$659,000

11040 KYLIE LN, Chestertown, MD 21620

4 Beds4 Baths3,684 SqFt

MLS# MDKE2004586

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
23393 CACAWAY FARM LN, Chestertown, MD 21620
Price Dropped by $100K

$1,350,000

23393 CACAWAY FARM LN, Chestertown, MD 21620

3 Beds4 Baths4,446 SqFt

MLS# MDKE2004002

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
116 PINE CHIP RD, Chestertown, MD 21620
Price Dropped by $20K

$495,000

116 PINE CHIP RD, Chestertown, MD 21620

3 Beds2 Baths2,767 SqFt

MLS# MDQA2010882

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
117 N WATER ST #1A, Chestertown, MD 21620
Active

$725,000

117 N WATER ST #1A, Chestertown, MD 21620

3 Beds3 Baths

MLS# MDKE2004206

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
349 HIGH ST, Chestertown, MD 21620
Active

$395,000

349 HIGH ST, Chestertown, MD 21620

7 Beds4 Baths3,664 SqFt

MLS# MDKE2004076

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
117 WATER ST N #2A, Chestertown, MD 21620
Active

$399,000

117 WATER ST N #2A, Chestertown, MD 21620

2 Beds1 Bath787 SqFt

MLS# MDKE2003742

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
228 S WATER ST, Chestertown, MD 21620
Price Dropped by $52K

$898,000

228 S WATER ST, Chestertown, MD 21620

3 Beds4 Baths2,592 Sqft Lot

MLS# MDKE2001612

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
866 WASHINGTON AVE, Chestertown, MD 21620
New

$299,000

866 WASHINGTON AVE, Chestertown, MD 21620

1,224 SqFt

MLS# MDKE2005460

Listed by Brenton Realty Group

Bright MLS (BMLS)
128 N QUEEN ST #3, Chestertown, MD 21620
New

$1,450

128 N QUEEN ST #3, Chestertown, MD 21620

1 Bed1 Bath900 SqFt

MLS# MDKE2005464

Listed by Brenton Realty Group

Bright MLS (BMLS)
GEORGETOWN RD, Chestertown, MD 21620
New

$30,000

GEORGETOWN RD, Chestertown, MD 21620

0.83 Acres

MLS# MDKE2005448

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
26933 MALLARD RD, Chestertown, MD 21620
Active

$625,000

26933 MALLARD RD, Chestertown, MD 21620

1,600 SqFt

MLS# MDKE2005422

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
CHURCH HILL ( LOT 2) RD, Chestertown, MD 21620
Active

$165,000

CHURCH HILL ( LOT 2) RD, Chestertown, MD 21620

5.34 Acres

MLS# MDQA2014030

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
6339 QUAKER NECK RD, Chestertown, MD 21620
Active

$2,500

6339 QUAKER NECK RD, Chestertown, MD 21620

3 Beds2 Baths1,908 SqFt

MLS# MDKE2005400

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
21217 TEXAS AVE, Chestertown, MD 21620
Active

$1,600

21217 TEXAS AVE, Chestertown, MD 21620

2 Beds1 Bath912 SqFt

MLS# MDKE2005432

Listed by RE/MAX Leading Edge

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

$149,900

HOFFECKER RD, Chestertown, MD 21620

10.05 Acres

MLS# MDQA2013914

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
5117-A DEEP POINT DR, Chestertown, MD 21620
Active

$3,200

5117-A DEEP POINT DR, Chestertown, MD 21620

3 Beds3 Baths31.52 Acres Lot

MLS# MDKE2005376

Listed by Rosendale Realty

Bright MLS (BMLS)
201 N LYNCHBURG ST, Chestertown, MD 21620
Active

$995,000

201 N LYNCHBURG ST, Chestertown, MD 21620

3,527 SqFt

MLS# MDKE2005278

Listed by RE/MAX Associates-Hockessin

Bright MLS (BMLS)
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      Home
      Buy
      1. View All Listings
      2. Steps to Buying Your Home
      Sell
      1. Steps to Sell Your Home
      2. Home Valuation
      3. Sold Listings
      About
      1. Contact Us
      2. About
      Renovate Now
      Simply Elite Exclusives
      1. Client Events
      2. Testimonials
      3. Military Relocation
      4. 30 Day Guarantee
      5. VIP Buyer Program
      6. Referrals
      7. Our Preferred Partners
      8. Market Reports
      Join Us At LPT
      1. Learn More About LPT
LPT Realty

Joseph & Danielle Dedekind

+1(703) 244-8787 joe@simplyelitehometeam.com

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defaultUntitled design (99)New-MRP-Logojpg-removebg-preview (1)
      Home
      Buy
      1. View All Listings
      2. Steps to Buying Your Home
      Sell
      1. Steps to Sell Your Home
      2. Home Valuation
      3. Sold Listings
      About
      1. Contact Us
      2. About
      Renovate Now
      Simply Elite Exclusives
      1. Client Events
      2. Testimonials
      3. Military Relocation
      4. 30 Day Guarantee
      5. VIP Buyer Program
      6. Referrals
      7. Our Preferred Partners
      8. Market Reports
      Join Us At LPT
      1. Learn More About LPT
LPT Realty

Joseph & Danielle Dedekind

+1(703) 244-8787 joe@simplyelitehometeam.com

TREC Consumer Protection Notice

TREC Information About Brokerage Services

Get My App

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

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

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.