Keller Williams Gateway
  • Home
  • Buy
    1. Buyers Guide
    2. Find Your Home
      1. Featured Listings
      2. Search Properties
    3. Luxury Listings
    4. Mortgage Calculator
  • Sell
    1. Sellers Guide
    2. Sell My Home
    3. Home Valuation
    4. Sold Listings
  • About
    1. About Us
  • Communities
    1. Baltimore City
    2. Baltimore County
    3. Harford County
    4. Cecil County
  • Discover
    1. Market Snapshot
      1. Baltimore City
      2. Baltimore County
      3. Harford County
  • Schedule Now
  • Contact Us
  • Join our Team
  • Blogs
  • Register
  • Sign In
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
    Beds Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
    Baths Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
  • List
  • Mixed
  • Map
Chestertown, MD
Map
128 Properties Available

128 Properties Available

The average price in the selected areas has remained stable. Learn more
  • Newest Listings
  • Price-High To Low
  • Price-Low To High
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
611 CANNON ST, Chestertown, MD 21620
1/18
Active

$299,000

2 Beds2 Baths920 SqFt

611 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005906

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
104 LITTLE HARBOR WAY, Chestertown, MD 21620
1/23
Active

$849,900

3 Beds3 Baths1,980 SqFt

104 LITTLE HARBOR WAY, Chestertown, MD 21620

MLS# MDKE2005894

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
106 LANDING LN, Chestertown, MD 21620
1/24
Active

$799,900

3 Beds4 Baths2,092 SqFt

106 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005892

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
LITTLE HARBOR WAY #1, Chestertown, MD 21620
1/25
Active

$1,459,000

3 Beds3 Baths2,231 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

MLS# MDKE2005768

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
105 HIGH ST, Chestertown, MD 21620
1/51
Active

$1,395,500

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
304 HADAWAY DR, Chestertown, MD 21620
1/44
Price Dropped by $26K

$399,000

4 Beds2 Baths1,325 SqFt

304 HADAWAY DR, Chestertown, MD 21620

MLS# MDKE2005848

Listed by Cummings & Co. Realtors

Bright MLS (BMLS)
222 MOUNT VERNON AVE, Chestertown, MD 21620
1/29
Active

$469,000

4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2005876

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
10230 JOHN CARVILL RD, Chestertown, MD 21620
1/41
Pending

$750,000

4 Beds3 Baths2,350 SqFt

10230 JOHN CARVILL RD, Chestertown, MD 21620

MLS# MDKE2005716

Listed by Shoreline Realty

Bright MLS (BMLS)
112 SILVER HEEL DR, Chestertown, MD 21620
1/43
Under Contract

$369,900

5 Beds4 Baths2,615 SqFt

112 SILVER HEEL DR, Chestertown, MD 21620

MLS# MDKE2005880

Listed by EXP Realty, LLC

Bright MLS (BMLS)
303 E CAMPUS AVE, Chestertown, MD 21620
1/32
Under Contract

$363,000

3 Beds2 Baths1,532 SqFt

303 E CAMPUS AVE, Chestertown, MD 21620

MLS# MDKE2005756

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
411 GREENWOOD AVE, Chestertown, MD 21620
1/32
Pending

$419,000

3 Beds3 Baths1,676 SqFt

411 GREENWOOD AVE, Chestertown, MD 21620

MLS# MDKE2005824

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
318 LINCOLN, Chestertown, MD 21620
1/21
Active

$269,000

3 Beds2 Baths960 SqFt

318 LINCOLN, Chestertown, MD 21620

MLS# MDKE2005842

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
10121 FAIRLEE RD, Chestertown, MD 21620
1/67
Active

$2,350,000

6 Beds5 Baths4,954 SqFt

10121 FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2005852

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
109 S COLLEGE AVE, Chestertown, MD 21620
1/24
Active

$449,900

3 Beds3 Baths1,216 SqFt

109 S COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2005818

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
8620 PARK DR, Chestertown, MD 21620
1/53
Active

$499,900

4 Beds3 Baths2,524 SqFt

8620 PARK DR, Chestertown, MD 21620

MLS# MDKE2005850

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
7844 CHESTER CT, Chestertown, MD 21620
1/51
Active

$770,000

4 Beds3 Baths3,248 SqFt

7844 CHESTER CT, Chestertown, MD 21620

MLS# MDKE2005796

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
206 S WATER ST, Chestertown, MD 21620
1/43
Active

$619,000

4 Beds4 Baths2,008 SqFt

206 S WATER ST, Chestertown, MD 21620

MLS# MDKE2005840

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
222 DUTCHESS RD, Chestertown, MD 21620
1/24
Active

$320,000

3 Beds2 Baths1,096 SqFt

222 DUTCHESS RD, Chestertown, MD 21620

MLS# MDQA2014830

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
492 PEAR TREE POINT RD, Chestertown, MD 21620
1/73
Under Contract

$875,000

3 Beds2 Baths3,720 SqFt

492 PEAR TREE POINT RD, Chestertown, MD 21620

MLS# MDQA2015126

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
228 S WATER ST, Chestertown, MD 21620
1/32
Active

$878,000

3 Beds4 Baths2,310 SqFt

228 S WATER ST, Chestertown, MD 21620

MLS# MDKE2005812

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
8750 GEORGETOWN RD, Chestertown, MD 21620
1/30
Price Dropped by $5K

$334,000

3 Beds2 Baths1,900 SqFt

8750 GEORGETOWN RD, Chestertown, MD 21620

MLS# MDKE2005834

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
127 WOOD DUCK LN, Chestertown, MD 21620
1/26
Active

$215,000

3 Beds2 Baths1,666 SqFt

127 WOOD DUCK LN, Chestertown, MD 21620

MLS# MDQA2015154

Listed by RE/MAX Point Realty

Bright MLS (BMLS)
107 MALONE AVE, Chestertown, MD 21620
1/27
Under Contract

$290,000

3 Beds1 Bath1,200 SqFt

107 MALONE AVE, Chestertown, MD 21620

MLS# MDKE2005764

Listed by Douglas Realty LLC

Bright MLS (BMLS)
206 VALLEY, Chestertown, MD 21620
1/35
Pending

$615,000

4 Beds2 Baths2,869 SqFt

206 VALLEY, Chestertown, MD 21620

MLS# MDKE2005762

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
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
      4. Mortgage Calculator
      Communities
      1. Baltimore City
      2. Baltimore County
      3. Harford County
      4. Cecil County
      Contact Us
    • Sell
      1. Sellers Guide
      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.
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
      4. Mortgage Calculator
      Communities
      1. Baltimore City
      2. Baltimore County
      3. Harford County
      4. Cecil County
      Contact Us
    • Sell
      1. Sellers Guide
      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.