Engel & Völkers
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
    4. Mortgage Calculator
  • Sell
    1. Sell My Home
    2. Home Valuation
  • Resources
  • About
    1. Reviews
    2. About Me
    3. Contact Us
  • MORE
    1. My Homes
    2. My Tours
    3. My Favorites
    4. My Searches
  • Sign In
  • Register
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
  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
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)
110 TRAFFORD DR, Chestertown, MD 21620
Coming Soon

$475,000

4 Beds3 Baths2,880 SqFt

110 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2005964

Listed by RE/MAX Advantage Realty

Bright MLS (BMLS)
311 DEVON DR, Chestertown, MD 21620
1/40
Open 1/3 2PM-4PM

$598,000

5 Beds4 Baths3,504 SqFt

311 DEVON DR, Chestertown, MD 21620

MLS# MDKE2005930

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
303 CEDAR ST, Chestertown, MD 21620
1/26
New

$333,900

3 Beds3 Baths2,577 SqFt

303 CEDAR ST, Chestertown, MD 21620

MLS# MDKE2005970

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/8
Coming Soon

$525,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
21111 TEXAS AVE, Chestertown, MD 21620
1/16
New

$370,000

3 Beds2 Baths1,680 SqFt

21111 TEXAS AVE, Chestertown, MD 21620

MLS# MDKE2005932

Listed by Keller Williams Select Realtors of Easton

Bright MLS (BMLS)
109 METCALF RD, Chestertown, MD 21620
1/27
Active

$264,900

3 Beds2 Baths1,280 SqFt

109 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005968

Listed by Real Broker, LLC

Bright MLS (BMLS)
676 DEEP LANDING RD, Chestertown, MD 21620
1/24
Under Contract

$315,000

3 Beds3 Baths1,468 SqFt

676 DEEP LANDING RD, Chestertown, MD 21620

MLS# MDQA2015466

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
#25 LANDING LN, Chestertown, MD 21620
1/22
Active

$1,099,900

4 Beds4 Baths2,784 SqFt

#25 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005954

Listed by Gunther-McClary Real Estate

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

$839,500

3 Beds3 Baths1,964 SqFt

102 LITTLE HARBOR WAY, Chestertown, MD 21620

MLS# MDKE2005950

Listed by Gunther-McClary Real Estate

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

$813,900

3 Beds4 Baths2,192 SqFt

104 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005952

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
#35 LANDING LN, Chestertown, MD 21620
1/26
Active

$786,900

3 Beds3 Baths1,964 SqFt

#35 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005956

Listed by Gunther-McClary Real Estate

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

$765,900

3 Beds3 Baths1,964 SqFt

#37 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005960

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
#36 LANDING LN, Chestertown, MD 21620
1/26
Active

$753,500

3 Beds3 Baths1,964 SqFt

#36 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005958

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
213 CENTRAL DR, Chestertown, MD 21620
1/23
Under Contract

$319,900

3 Beds2 Baths1,232 SqFt

213 CENTRAL DR, Chestertown, MD 21620

MLS# MDQA2015648

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
7521 PINE AVE, Chestertown, MD 21620
1/24
Under Contract

$250,000

3 Beds1 Bath1,040 SqFt

7521 PINE AVE, Chestertown, MD 21620

MLS# MDKE2005920

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
204 ROLLING RD, Chestertown, MD 21620
1/31
Active

$370,000

3 Beds2 Baths2,296 SqFt

204 ROLLING RD, Chestertown, MD 21620

MLS# MDKE2005896

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
216 BLAKEFIELD DR, Chestertown, MD 21620
Active

$579,000

4 Beds3 Baths2,400 SqFt

216 BLAKEFIELD DR, Chestertown, MD 21620

MLS# MDQA2015520

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
121 PRIMROSE RD, Chestertown, MD 21620
1/22
Price Dropped by $24K

$375,000

3 Beds3 Baths2,034 SqFt

121 PRIMROSE RD, Chestertown, MD 21620

MLS# MDQA2015570

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
108 FLYING CLOUD DR, Chestertown, MD 21620
1/21
Price Dropped by $10K

$364,900

4 Beds3 Baths1,936 SqFt

108 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2005928

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
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)
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)
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)
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
advisorlogo-shafferkara
    • Home
      Resources
    • Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. Mortgage Calculator
      About
      1. Reviews
      2. About Me
      3. Contact Us
    • Sell
      1. Sell My Home
      2. Home Valuation
Engel & Völkers
Kara Shaffer

+1(443) 926-3287 [email protected]

138 West St, Annapolis, MD, 21401, USA
Kara Shaffer mobile: +1 (443) 926-3287 email: [email protected] office: +1 (443) 292-6767

Get My App

Download for iOS
iOS
Download for Android
Android

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.
advisorlogo-shafferkara
    • Home
      Resources
    • Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. Mortgage Calculator
      About
      1. Reviews
      2. About Me
      3. Contact Us
    • Sell
      1. Sell My Home
      2. Home Valuation
Engel & Völkers
Kara Shaffer

+1(443) 926-3287 [email protected]

138 West St, Annapolis, MD, 21401, USA
Kara Shaffer mobile: +1 (443) 926-3287 email: [email protected] office: +1 (443) 292-6767

Get My App

Download for iOS
iOS
Download for Android
Android

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.