6,645

Properties in ZIP Code 21620

Section Image
    • 120 Metcalf Rd, Chestertown, MD 21620
      120 Metcalf Rd, Chestertown, MD 21620
      120 Metcalf Rd, Chestertown, MD 21620
      /19

      Est $249,123

      Not Listed For Sale

      120 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2023
      120 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

    • 118 Metcalf Rd, Chestertown, MD 21620
      118 Metcalf Rd, Chestertown, MD 21620
      118 Metcalf Rd, Chestertown, MD 21620
      /18

      Est $244,914

      Not Listed For Sale

      118 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,140 Sq Ft
      • Built 2023
      118 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

    • 116 Metcalf Rd, Chestertown, MD 21620
      116 Metcalf Rd, Chestertown, MD 21620
      116 Metcalf Rd, Chestertown, MD 21620
      /27

      Est $241,735

      Not Listed For Sale

      116 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • Built 2023
      116 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

    • 114 Metcalf Rd, Chestertown, MD 21620
      114 Metcalf Rd, Chestertown, MD 21620
      114 Metcalf Rd, Chestertown, MD 21620
      /18

      Est $238,370

      Not Listed For Sale

      114 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2024
      114 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 98 Days On Market

    • 106 Metcalf Rd, Chestertown, MD 21620
      106 Metcalf Rd, Chestertown, MD 21620
      106 Metcalf Rd, Chestertown, MD 21620
      /18

      Est $234,688

      Not Listed For Sale

      106 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2024
      106 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

    • 102 Metcalf Rd, Chestertown, MD 21620
      102 Metcalf Rd, Chestertown, MD 21620
      102 Metcalf Rd, Chestertown, MD 21620
      /3

      Est $241,172

      Not Listed For Sale

      102 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,140 Sq Ft
      • Built 2023
      102 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

    • 10719 Mallard Point Rd, Chestertown, MD 21620
      10719 Mallard Point Rd, Chestertown, MD 21620
      10719 Mallard Point Rd, Chestertown, MD 21620
      /26

      Est $342,998

      Not Listed For Sale

      10719 Mallard Point Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2015
      10719 Mallard Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 15 Days On Market

    • 23829 E Fork Dr, Chestertown, MD 21620
      23829 E Fork Dr, Chestertown, MD 21620
      23829 E Fork Dr, Chestertown, MD 21620
      /87

      Est $1,684,892

      Not Listed For Sale

      23829 E Fork Dr, Chestertown, MD 21620

      • 3 Beds
      • 4.5 Baths
      • 3,342 Sq Ft
      • Built 1993
      23829 E Fork Dr, Chestertown, MD 21620

      Last Sold Summary

      • 125 Days On Market

    • 104 Church Aly, Chestertown, MD 21620
      104 Church Aly, Chestertown, MD 21620
      104 Church Aly, Chestertown, MD 21620
      /51

      Est $360,401

      Not Listed For Sale

      104 Church Aly, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,058 Sq Ft
      • Built 1880
      104 Church Aly, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

    • 343 Calvert St, Chestertown, MD 21620
      343 Calvert St, Chestertown, MD 21620
      /2

      Not Listed For Sale

      343 Calvert St, Chestertown, MD 21620

      • 1 Bed
      • 1 Bath
      • 550 Sq Ft
      • Built 1987
      343 Calvert St, Chestertown, MD 21620

    • 8974 S Bayview Dr, Chestertown, MD 21620
      8974 S Bayview Dr, Chestertown, MD 21620
      8974 S Bayview Dr, Chestertown, MD 21620
      /86

      Est $2,207,707

      Not Listed For Sale

      8974 S Bayview Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,232 Sq Ft
      • Built 2011
      8974 S Bayview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

    • Lot 72 & 73 Buck Neck Rd, Chestertown, MD 21620
      Lot 72 & 73 Buck Neck Rd, Chestertown, MD 21620
      Lot 72 & 73 Buck Neck Rd, Chestertown, MD 21620
      /9

      Not Listed For Sale

      Lot 72 & 73 Buck Neck Rd, Chestertown, MD 21620

      Lot 72 & 73 Buck Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 313 Days On Market

    • 7488 Poplar Ave, Chestertown, MD 21620
      7488 Poplar Ave, Chestertown, MD 21620
      7488 Poplar Ave, Chestertown, MD 21620
      /40

      Est $272,599

      Not Listed For Sale

      7488 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2019
      7488 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

    • 225 S Water St Unit 6, Chestertown, MD 21620
      225 S Water St Unit 6, Chestertown, MD 21620
      225 S Water St Unit 6, Chestertown, MD 21620
      /56

      Est $996,961

      Not Listed For Sale

      225 S Water St Unit 6, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 2,800 Sq Ft
      • Built 2006
      225 S Water St Unit 6, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

    • 829 High St, Chestertown, MD 21620
      829 High St, Chestertown, MD 21620
      829 High St, Chestertown, MD 21620
      /12

      Est $225,549

      Not Listed For Sale

      829 High St, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 928 Sq Ft
      • Built 1900
      829 High St, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

    • 25478 Prestwick Dr, Chestertown, MD 21620
      25478 Prestwick Dr, Chestertown, MD 21620
      25478 Prestwick Dr, Chestertown, MD 21620
      /50

      Est $831,302

      Not Listed For Sale

      25478 Prestwick Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,736 Sq Ft
      • Built 2017
      25478 Prestwick Dr, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

    • 724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      /63

      Est $366,944

      Not Listed For Sale

      724 Deep Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,311 Sq Ft
      • Built 2018
      724 Deep Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 45 Days On Market

    • 709 High St, Chestertown, MD 21620
      709 High St, Chestertown, MD 21620
      709 High St, Chestertown, MD 21620
      /7

      Est $273,246

      Not Listed For Sale

      709 High St, Chestertown, MD 21620

      • Built 2024
      709 High St, Chestertown, MD 21620

      Last Sold Summary

      • 48 Days On Market

    • 136 Pearl Creek Ln, Chestertown, MD 21620
      136 Pearl Creek Ln, Chestertown, MD 21620
      136 Pearl Creek Ln, Chestertown, MD 21620
      /18

      Est $406,485

      Not Listed For Sale

      136 Pearl Creek Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,460 Sq Ft
      • Built 2019
      136 Pearl Creek Ln, Chestertown, MD 21620

      Last Sold Summary

      • 525 Days On Market

    • 221 Central Dr, Chestertown, MD 21620
      221 Central Dr, Chestertown, MD 21620
      221 Central Dr, Chestertown, MD 21620
      /11

      Est $330,575

      Not Listed For Sale

      221 Central Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2022
      221 Central Dr, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

    • 1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      /25

      Est $439,180

      Not Listed For Sale

      1213 Ewingtown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,528 Sq Ft
      • Built 2022
      1213 Ewingtown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 132 Days On Market

    • 108 Harlan Loop, Chestertown, MD 21620
      108 Harlan Loop, Chestertown, MD 21620
      108 Harlan Loop, Chestertown, MD 21620
      /73

      Est $514,560

      Not Listed For Sale

      108 Harlan Loop, Chestertown, MD 21620

      • 5 Beds
      • 2.5 Baths
      • 3,692 Sq Ft
      • Built 2010
      108 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 15 Days On Market

    • 10598 Klamath Rd, Chestertown, MD 21620
      10598 Klamath Rd, Chestertown, MD 21620
      10598 Klamath Rd, Chestertown, MD 21620
      /12

      Est $387,813

      Not Listed For Sale

      10598 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,499 Sq Ft
      • Built 2020
      10598 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 49 Days On Market

    • 141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      /18

      Est $1,133,596

      Not Listed For Sale

      141 Round Top Creek Ln, Chestertown, MD 21620

      • Studio
      • Built 1900
      141 Round Top Creek Ln, Chestertown, MD 21620

      Last Sold Summary

      • 194 Days On Market

    • 8725 Oak St, Chestertown, MD 21620
      8725 Oak St, Chestertown, MD 21620
      8725 Oak St, Chestertown, MD 21620
      /35

      Est $428,390

      Not Listed For Sale

      8725 Oak St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft
      • Built 2009
      8725 Oak St, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

    • 116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      /54

      Est $659,556

      Not Listed For Sale

      116 N Queen St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,110 Sq Ft
      • Built 1920
      116 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

    • 331 Devon Dr, Chestertown, MD 21620
      331 Devon Dr, Chestertown, MD 21620
      331 Devon Dr, Chestertown, MD 21620
      /48

      Est $510,724

      Not Listed For Sale

      331 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,834 Sq Ft
      • Built 2009
      331 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

    • 335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      /44

      Est $526,933

      Not Listed For Sale

      335 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 4,874 Sq Ft
      • Built 2009
      335 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

    • 106 Camelot Dr, Chestertown, MD 21620
      106 Camelot Dr, Chestertown, MD 21620
      106 Camelot Dr, Chestertown, MD 21620
      /55

      Est $519,814

      Not Listed For Sale

      106 Camelot Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,760 Sq Ft
      • Built 2009
      106 Camelot Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8 Days On Market

    • 103 Camelot Dr, Chestertown, MD 21620
      103 Camelot Dr, Chestertown, MD 21620
      103 Camelot Dr, Chestertown, MD 21620
      /22

      Est $493,788

      Not Listed For Sale

      103 Camelot Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 3,816 Sq Ft
      • Built 2009
      103 Camelot Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

    • 113 Trafford Dr, Chestertown, MD 21620
      113 Trafford Dr, Chestertown, MD 21620
      113 Trafford Dr, Chestertown, MD 21620
      /36

      Est $477,303

      Not Listed For Sale

      113 Trafford Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,490 Sq Ft
      • Built 2010
      113 Trafford Dr, Chestertown, MD 21620

      Last Sold Summary

      • 28 Days On Market

    • 118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      /8

      Est $649,480

      Not Listed For Sale

      118 Little Harbor Way Unit 102, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2009
      118 Little Harbor Way Unit 102, Chestertown, MD 21620

      Last Sold Summary

    • 23150 Club Terrace, Chestertown, MD 21620
      23150 Club Terrace, Chestertown, MD 21620
      23150 Club Terrace, Chestertown, MD 21620
      /30

      Est $326,760

      Not Listed For Sale

      23150 Club Terrace, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1991
      23150 Club Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 36 Days On Market

    • 105 Lyons Ln, Chestertown, MD 21620
      105 Lyons Ln, Chestertown, MD 21620
      105 Lyons Ln, Chestertown, MD 21620
      /35

      Est $336,970

      Not Listed For Sale

      105 Lyons Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft
      • Built 1997
      105 Lyons Ln, Chestertown, MD 21620

      Last Sold Summary

      • 29 Days On Market

    • 110 Wilton Rd, Chestertown, MD 21620
      110 Wilton Rd, Chestertown, MD 21620
      110 Wilton Rd, Chestertown, MD 21620
      /32

      Est $350,143

      Not Listed For Sale

      110 Wilton Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,411 Sq Ft
      • Built 1975
      110 Wilton Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

    • 117 Tuxedo Rd, Chestertown, MD 21620
      117 Tuxedo Rd, Chestertown, MD 21620
      117 Tuxedo Rd, Chestertown, MD 21620
      /46

      Est $374,833

      Not Listed For Sale

      117 Tuxedo Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1984
      117 Tuxedo Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

    • 120 Klinefellar Ln, Chestertown, MD 21620
      120 Klinefellar Ln, Chestertown, MD 21620
      120 Klinefellar Ln, Chestertown, MD 21620
      /39

      Est $472,202

      Not Listed For Sale

      120 Klinefellar Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,344 Sq Ft
      • Built 1977
      120 Klinefellar Ln, Chestertown, MD 21620

      Last Sold Summary

      • 42 Days On Market

    • 414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      /42

      Est $399,223

      Not Listed For Sale

      414 Pine Tree Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,688 Sq Ft
      • Built 1968
      414 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 47 Days On Market

    • 326 Rolphs Wharf Rd, Chestertown, MD 21620
      326 Rolphs Wharf Rd, Chestertown, MD 21620
      326 Rolphs Wharf Rd, Chestertown, MD 21620
      /4

      Not Listed For Sale

      326 Rolphs Wharf Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1999
      326 Rolphs Wharf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

    • 153 Longfellow Dr, Chestertown, MD 21620
      153 Longfellow Dr, Chestertown, MD 21620
      153 Longfellow Dr, Chestertown, MD 21620
      /27

      Est $297,556

      Not Listed For Sale

      153 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft
      • Built 1974
      153 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 121 Days On Market

Showing Results 361 - 400, Page 10 of 18

Maryland Kent County Chestertown

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group