EXIT Landmark Realty
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
  • Blogs
  • About
    1. About Us
    2. Contact Us
    3. Reviews
  • Market Snapshot
  • MORE
    1. My Homes
    2. My Tours
    3. My Favorites
    4. My Searches
  • Sign In
  • Register
Filters Reset
Save Search (2)
Save your search to get Alerts
96 Properties

96 Properties Available In Chestertown

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
MD >Chestertown >
Market Insights
204 ROLLING RD, Chestertown, MD 21620
1/31 31
Open Sat 11AM-1PM

$ 370,000

3 Beds2 Baths2,296 SqFt

204 ROLLING RD, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005896

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
318 LINCOLN, Chestertown, MD 21620
1/21 21
Open Sat 12PM-3PM

$ 269,000

3 Beds2 Baths960 SqFt

318 LINCOLN, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005842

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$ 315,000

3 Beds3 Baths1,468 SqFt

676 DEEP LANDING RD, Chestertown, MD 21620

Single Family Home

MLS# MDQA2015466

Listed by Cross Street Realtors LLC

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

$ 1,099,900

4 Beds4 Baths2,784 SqFt

#25 LANDING LN, Chestertown, MD 21620

Condo

MLS# MDKE2005954

Listed by Gunther-McClary Real Estate

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

$ 839,500

3 Beds3 Baths1,964 SqFt

102 LITTLE HARBOR WAY, Chestertown, MD 21620

Condo

MLS# MDKE2005950

Listed by Gunther-McClary Real Estate

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

$ 813,900

3 Beds4 Baths2,192 SqFt

104 LANDING LN, Chestertown, MD 21620

Condo

MLS# MDKE2005952

Listed by Gunther-McClary Real Estate

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

$ 786,900

3 Beds3 Baths1,964 SqFt

#35 LANDING LN, Chestertown, MD 21620

Condo

MLS# MDKE2005956

Listed by Gunther-McClary Real Estate

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

$ 765,900

3 Beds3 Baths1,964 SqFt

#37 LANDING LN, Chestertown, MD 21620

Condo

MLS# MDKE2005960

Listed by Gunther-McClary Real Estate

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

$ 753,500

3 Beds3 Baths1,964 SqFt

#36 LANDING LN, Chestertown, MD 21620

Condo

MLS# MDKE2005958

Listed by Gunther-McClary Real Estate

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

$ 319,900

3 Beds2 Baths1,232 SqFt

213 CENTRAL DR, Chestertown, MD 21620

Single Family Home

MLS# MDQA2015648

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$ 265,000

3 Beds1 Bath1,040 SqFt

7521 PINE AVE, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005920

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
311 DEVON DR, Chestertown, MD 21620
1/40 40
Active

$ 598,000

5 Beds4 Baths3,504 SqFt

311 DEVON DR, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005930

Listed by Doug Ashley Realtors, LLC

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

$ 579,000

4 Beds3 Baths2,400 SqFt

216 BLAKEFIELD DR, Chestertown, MD 21620

Single Family Home

MLS# MDQA2015520

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
121 PRIMROSE RD, Chestertown, MD 21620
1/22 22
Active

$ 399,000

3 Beds3 Baths2,034 SqFt

121 PRIMROSE RD, Chestertown, MD 21620

Single Family Home

MLS# MDQA2015570

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
108 FLYING CLOUD DR, Chestertown, MD 21620
1/21 21
Active

$ 375,000

4 Beds3 Baths1,936 SqFt

108 FLYING CLOUD DR, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005928

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
611 CANNON ST, Chestertown, MD 21620
1/18 18
Active

$ 299,000

2 Beds2 Baths920 SqFt

611 CANNON ST, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005906

Listed by Select Land & Homes, LLC

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

$ 1,459,000

3 Beds3 Baths2,231 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

Condo

MLS# MDKE2005768

Listed by Gunther-McClary Real Estate

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

$ 849,900

3 Beds3 Baths1,980 SqFt

104 LITTLE HARBOR WAY, Chestertown, MD 21620

Condo

MLS# MDKE2005894

Listed by Gunther-McClary Real Estate

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

$ 799,900

3 Beds4 Baths2,092 SqFt

106 LANDING LN, Chestertown, MD 21620

Condo

MLS# MDKE2005892

Listed by Gunther-McClary Real Estate

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

$ 1,395,500

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$ 399,000

4 Beds2 Baths1,325 SqFt

304 HADAWAY DR, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005848

Listed by Cummings & Co. Realtors

Bright MLS (BMLS)
222 MOUNT VERNON AVE, Chestertown, MD 21620
1/29 29
Price Dropped by $5K

$ 470,000

4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005876

Listed by Long & Foster Real Estate, Inc.

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

$ 2,350,000

6 Beds5 Baths4,954 SqFt

10121 FAIRLEE RD, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005852

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$ 499,900

4 Beds3 Baths2,524 SqFt

8620 PARK DR, Chestertown, MD 21620

Single Family Home

MLS# MDKE2005850

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
  • 1
  • 2
  • 3
  • 4

explore listings in Chestertown

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
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.

SITE MAP

      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      Blogs
      About
      1. About Us
      2. Contact Us
      3. Reviews
      Market Snapshot
Real Logo Outline White

Real Broker, LLC

Sharron Owens License ID: SP89810, 584245, 0225271273

+1(240) 504-5394 sharron@sharronowens.com

4550 Crain Hwy Ste 100, White Plains, MD 20695

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.

SITE MAP

      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      Blogs
      About
      1. About Us
      2. Contact Us
      3. Reviews
      Market Snapshot
Real Logo Outline White

Real Broker, LLC

Sharron Owens License ID: SP89810, 584245, 0225271273

+1(240) 504-5394 sharron@sharronowens.com

4550 Crain Hwy Ste 100, White Plains, MD 20695

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