Jersey Shore Real Estate Experts Jersey Shore Real Estate Experts
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Recent Sold
  • Explore Towns
    1. Atlantic City
    2. Avalon
    3. Beach Haven
    4. Cape May
    5. Cape May Court House
    6. Cape May Point
    7. North Cape May
    8. North Wildwood
    9. Ocean City
    10. Rio Grande
    11. Sea Isle City
    12. Stone Harbor
    13. Villas
    14. West Cape May
    15. West Wildwood
    16. Wildwood
    17. Wildwood Crest
  • About
    1. My Team
    2. About Us
    3. Contact Us
    4. Reviews
  • Market Snapshot
  • Resources
    1. Calendar
    2. Affordability Calculator
    3. Mortgage Calculator
    4. Blogs
    5. Partner Lender
Register
/
Sign In
    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+
    Property Type
    Any
  • List
  • Mixed
  • Map
Chestertown, MD
Map
2,673 Sold Properties

2,673 Sold Properties

The average price in the selected areas has remained stable. Learn more
  • Default
  • Most Recent
  • Price-Highest
  • Price-Lowest
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
100 ACORN DR, Chestertown, MD 21620
1/27

$280,000

$285,000

1.8%
3 Beds3 Baths1,930 SqFt

100 ACORN DR, Chestertown, MD 21620

MLS# MDKE2004566

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
1814 PONDTOWN RD, Chestertown, MD 21620
1/8

$86,000

$95,000

9.5%
3 Beds1 Bath973 SqFt

1814 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2013018

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
129 N QUEEN ST N, Chestertown, MD 21620
1/38

$575,000

$598,500

3.9%
3 Beds3 Baths2,296 SqFt

129 N QUEEN ST N, Chestertown, MD 21620

MLS# MDKE2004970

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
508 CANNON ST, Chestertown, MD 21620
1/20

$150,000

$150,000

3 Beds3 Baths2,240 SqFt

508 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005160

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
22671 WOOD YARD LN, Chestertown, MD 21620
1/4

$15,000

$15,000

0.48 Acres

22671 WOOD YARD LN, Chestertown, MD 21620

MLS# MDKE2005122

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
Chestertown, MD 21620

$90,000

$135,000

33.3%
13.46 Acres

Chestertown, MD 21620

MLS# MDKE2005014

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
23315 SANDPIPER RD, Chestertown, MD 21620
1/37

$295,000

$309,000

4.5%
2 Beds2 Baths1,272 SqFt

23315 SANDPIPER RD, Chestertown, MD 21620

MLS# MDKE2004728

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
10705 MILLBROOK DR, Chestertown, MD 21620
1/43

$262,500

$305,000

13.9%
4 Beds3 Baths2,106 SqFt

10705 MILLBROOK DR, Chestertown, MD 21620

MLS# MDKE2004846

Listed by EXP Realty, LLC

Bright MLS (BMLS)
SANDPIPER RD, Chestertown, MD 21620
1/5

$11,000

$10,000

10.0%
0.34 Acres

SANDPIPER RD, Chestertown, MD 21620

MLS# MDKE2003870

Listed by Ashland Auction Group LLC

Bright MLS (BMLS)
5594 LANGFORD BAY RD, Chestertown, MD 21620
1/40

$750,000

$700,000

7.1%
3 Beds2 Baths1,682 SqFt

5594 LANGFORD BAY RD, Chestertown, MD 21620

MLS# MDKE2005118

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
1106 ROUND TOP RD, Chestertown, MD 21620
1/27

$250,000

$289,000

13.5%
3 Beds2 Baths1,248 SqFt

1106 ROUND TOP RD, Chestertown, MD 21620

MLS# MDQA2012854

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
101 S MILL ST, Chestertown, MD 21620
1/22

$490,000

$485,000

1.0%
2 Beds3 Baths1,476 SqFt

101 S MILL ST, Chestertown, MD 21620

MLS# MDKE2004984

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
108 N QUEEN ST, Chestertown, MD 21620
1/40

$600,000

$599,900

5 Beds3 Baths2,536 SqFt

108 N QUEEN ST, Chestertown, MD 21620

MLS# MDKE2004886

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
FAIRLEE RD, Chestertown, MD 21620
1/8

$50,000

$79,900

37.4%
2.2 Acres

FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2004652

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
308-A LANDING LN, Chestertown, MD 21620
1/32

$782,500

$789,000

0.8%
3 Beds3 Baths2,204 SqFt

308-A LANDING LN, Chestertown, MD 21620

MLS# MDKE2004928

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
8605 CAMP RD, Chestertown, MD 21620
1/51

$370,000

$385,000

3.9%
3 Beds2 Baths1,296 SqFt

8605 CAMP RD, Chestertown, MD 21620

MLS# MDKE2004952

Listed by RE/MAX Executive

Bright MLS (BMLS)
202 GLEN ST, Chestertown, MD 21620
1/37

$290,000

$290,000

3 Beds1 Bath1,252 SqFt

202 GLEN ST, Chestertown, MD 21620

MLS# MDKE2004712

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
116 OAK LEAF DR, Chestertown, MD 21620
1/38

$289,500

$289,500

2 Beds4 Baths1,867 SqFt

116 OAK LEAF DR, Chestertown, MD 21620

MLS# MDKE2004942

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
118 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/34

$265,000

$269,000

1.5%
3 Beds2 Baths1,114 SqFt

118 CHAR NOR MANOR BLVD, Chestertown, MD 21620

MLS# MDQA2011266

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
123 BURCHARD SAWMILL RD, Chestertown, MD 21620
1/53

$485,000

$485,000

3 Beds3 Baths1,648 SqFt

123 BURCHARD SAWMILL RD, Chestertown, MD 21620

MLS# MDQA2012234

Listed by EXP Realty, LLC

Bright MLS (BMLS)
107 CHESTER ARMS DR, Chestertown, MD 21620
1/19

$230,000

$236,000

2.5%
3 Beds2 Baths1,140 SqFt

107 CHESTER ARMS DR, Chestertown, MD 21620

MLS# MDKE2004904

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
505 N KENT ST, Chestertown, MD 21620
1/23

$352,500

$345,000

2.2%
3 Beds2 Baths1,402 SqFt

505 N KENT ST, Chestertown, MD 21620

MLS# MDKE2004864

Listed by Rock Hall Properties Real Estate

Bright MLS (BMLS)
113 PINE COVE LN, Chestertown, MD 21620
1/2

$57,500

$68,500

16.1%
0.45 Acres

113 PINE COVE LN, Chestertown, MD 21620

MLS# MDQA2009464

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
130 SHEAFFER RD, Chestertown, MD 21620
1/25

$431,000

$434,500

0.8%
4 Beds2 Baths1,766 SqFt

130 SHEAFFER RD, Chestertown, MD 21620

MLS# MDQA2012600

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
  • 1
  • ...
  • 4
  • 5
  • 6
  • 7
  • 8
  • ...
  • 112
eXp Realty - White
eXp Realty
Chip Watson
      Home
      Buy
      1. All Listings
      2. Featured Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Recent Sold
      Explore Towns
      1. Atlantic City
      2. Avalon
      3. Beach Haven
      4. Cape May
      5. Cape May Court House
      6. Cape May Point
      7. North Cape May
      8. North Wildwood
      9. Ocean City
      10. Rio Grande
      11. Sea Isle City
      12. Stone Harbor
      13. Villas
      14. West Cape May
      15. West Wildwood
      16. Wildwood
      17. Wildwood Crest
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      Market Snapshot
      Resources
      1. Calendar
      2. Affordability Calculator
      3. Mortgage Calculator
      4. Blogs
      5. Partner Lender
+1(856) 625-5900
howard.watson@exprealty.com

Get My App

Do Not Sell or Share My Personal Data

Name: Debra Ball - Maine MLS Contact: 1-888-439-8743 Name: Deborah Penny contact: 1-805-284-0995 email: deborah.penny@exprealty.net Designation: Licensed Broker of EXP Realty for Metrolist   Name: Christopher Cribb contact: 1-816-982-5990 email: chris.cribb@exprealty.net Designation: Licensed Broker of EXP Realty for Heartland MLS   Name: Amy Logue contact:  1-503-814-9613 email:  amy.logue@exprealty.net Designation: Licensed Broker of EXP Realty for Willamette Valley MLS    

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.

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

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

eXp Realty - White
eXp Realty
Chip Watson
      Home
      Buy
      1. All Listings
      2. Featured Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Recent Sold
      Explore Towns
      1. Atlantic City
      2. Avalon
      3. Beach Haven
      4. Cape May
      5. Cape May Court House
      6. Cape May Point
      7. North Cape May
      8. North Wildwood
      9. Ocean City
      10. Rio Grande
      11. Sea Isle City
      12. Stone Harbor
      13. Villas
      14. West Cape May
      15. West Wildwood
      16. Wildwood
      17. Wildwood Crest
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      Market Snapshot
      Resources
      1. Calendar
      2. Affordability Calculator
      3. Mortgage Calculator
      4. Blogs
      5. Partner Lender
+1(856) 625-5900
howard.watson@exprealty.com

Get My App

Do Not Sell or Share My Personal Data

Name: Debra Ball - Maine MLS Contact: 1-888-439-8743 Name: Deborah Penny contact: 1-805-284-0995 email: deborah.penny@exprealty.net Designation: Licensed Broker of EXP Realty for Metrolist   Name: Christopher Cribb contact: 1-816-982-5990 email: chris.cribb@exprealty.net Designation: Licensed Broker of EXP Realty for Heartland MLS   Name: Amy Logue contact:  1-503-814-9613 email:  amy.logue@exprealty.net Designation: Licensed Broker of EXP Realty for Willamette Valley MLS    

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.

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

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