6,890

Chestertown, MD Homes

Section Image
    • 7514 Muirfield Dr, Chestertown, MD 21620
      7514 Muirfield Dr, Chestertown, MD 21620
      7514 Muirfield Dr, Chestertown, MD 21620
      /20

      Est $831,947

      Not Listed For Sale

      7514 Muirfield Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • Built 2024
      7514 Muirfield Dr, Chestertown, MD 21620

      Last Sold Summary

      • 31 Days On Market

    • 21345 Persimmon Dr, Chestertown, MD 21620
      21345 Persimmon Dr, Chestertown, MD 21620
      21345 Persimmon Dr, Chestertown, MD 21620
      /6

      Est $166,517

      Not Listed For Sale

      21345 Persimmon Dr, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1955
      21345 Persimmon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

    • 117 N Water St Unit 3A, Chestertown, MD 21620
      117 N Water St Unit 3A, Chestertown, MD 21620
      117 N Water St Unit 3A, Chestertown, MD 21620
      /23

      Est $1,125,595

      Not Listed For Sale

      117 N Water St Unit 3A, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 729 Sq Ft
      • Built 1886
      117 N Water St Unit 3A, Chestertown, MD 21620

      Last Sold Summary

      • 77 Days On Market

    • 0 Truslow Farm Ln, Chestertown, MD 21620
      0 Truslow Farm Ln, Chestertown, MD 21620
      0 Truslow Farm Ln, Chestertown, MD 21620
      /10

      Not Listed For Sale

      0 Truslow Farm Ln, Chestertown, MD 21620

      0 Truslow Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 322 Days On Market

    • 0 Foxchase Dr, Chestertown, MD 21620
      0 Foxchase Dr, Chestertown, MD 21620
      0 Foxchase Dr, Chestertown, MD 21620
      /29

      Not Listed For Sale

      0 Foxchase Dr, Chestertown, MD 21620

      0 Foxchase Dr, Chestertown, MD 21620

      Last Sold Summary

      • 34 Days On Market

    • 235 Island Lark Way, Chestertown, MD 21620
      235 Island Lark Way, Chestertown, MD 21620
      235 Island Lark Way, Chestertown, MD 21620
      /22

      Est $296,835

      Not Listed For Sale

      235 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,420 Sq Ft
      • Built 2023
      235 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 8 Days On Market

    • 0 Royston Shores Rd Unit MDQA2008544, Chestertown, MD 21620
      0 Royston Shores Rd Unit MDQA2008544, Chestertown, MD 21620
      0 Royston Shores Rd Unit MDQA2008544, Chestertown, MD 21620
      /13

      Not Listed For Sale

      0 Royston Shores Rd Unit MDQA2008544, Chestertown, MD 21620

      0 Royston Shores Rd Unit MDQA2008544, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

    • 104 W Campus Ave, Chestertown, MD 21620
      104 W Campus Ave, Chestertown, MD 21620
      104 W Campus Ave, Chestertown, MD 21620
      /36

      Est $398,351

      Not Listed For Sale

      104 W Campus Ave, Chestertown, MD 21620

      • 3 Beds
      • 5 Baths
      • 2,884 Sq Ft
      • Built 1949
      104 W Campus Ave, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

    • 245 Island Lark Way, Chestertown, MD 21620
      245 Island Lark Way, Chestertown, MD 21620
      245 Island Lark Way, Chestertown, MD 21620
      /27

      Est $295,664

      Not Listed For Sale

      245 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2023
      245 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 30 Days On Market

    • 247 Island Lark Way, Chestertown, MD 21620
      247 Island Lark Way, Chestertown, MD 21620
      247 Island Lark Way, Chestertown, MD 21620
      /27

      Est $280,942

      Not Listed For Sale

      247 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2023
      247 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

    • 251 Island Lark Way, Chestertown, MD 21620
      251 Island Lark Way, Chestertown, MD 21620
      251 Island Lark Way, Chestertown, MD 21620
      /27

      Est $284,243

      Not Listed For Sale

      251 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2023
      251 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

    • 253 Island Lark Way, Chestertown, MD 21620
      253 Island Lark Way, Chestertown, MD 21620
      253 Island Lark Way, Chestertown, MD 21620
      /27

      Est $292,221

      Not Listed For Sale

      253 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2023
      253 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

    • 0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620
      0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620
      0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620
      /7

      Not Listed For Sale

      0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620

      0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620

      Last Sold Summary

      • 158 Days On Market

    • 22900 Handy Point Rd, Chestertown, MD 21620
      22900 Handy Point Rd, Chestertown, MD 21620
      22900 Handy Point Rd, Chestertown, MD 21620
      /68

      Est $1,783,656

      Not Listed For Sale

      22900 Handy Point Rd, Chestertown, MD 21620

      • 5 Beds
      • 5 Baths
      • 4,885 Sq Ft
      • Built 2006
      22900 Handy Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 132 Days On Market

    • 106-1 N Water St Unit 1/2, Chestertown, MD 21620
      106-1 N Water St Unit 1/2, Chestertown, MD 21620
      106-1 N Water St Unit 1/2, Chestertown, MD 21620
      /41

      Not Listed For Sale

      106-1 N Water St Unit 1/2, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,866 Sq Ft
      • Built 1900
      106-1 N Water St Unit 1/2, Chestertown, MD 21620

      Last Sold Summary

      • 179 Days On Market

    • 424 Chester River Heights Rd, Chestertown, MD 21620
      424 Chester River Heights Rd, Chestertown, MD 21620
      424 Chester River Heights Rd, Chestertown, MD 21620
      /31

      Not Listed For Sale

      424 Chester River Heights Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,491 Sq Ft
      • Built 1950
      424 Chester River Heights Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

    • 0 Buck Neck Rd Unit MDKE2003206, Chestertown, MD 21620
      0 Buck Neck Rd Unit MDKE2003206, Chestertown, MD 21620
      0 Buck Neck Rd Unit MDKE2003206, Chestertown, MD 21620
      /3

      Not Listed For Sale

      0 Buck Neck Rd Unit MDKE2003206, Chestertown, MD 21620

      0 Buck Neck Rd Unit MDKE2003206, Chestertown, MD 21620

      Last Sold Summary

      • 25 Days On Market

    • 10044 John Carvill (4th Point) Rd, Chestertown, MD 21620
      10044 John Carvill (4th Point) Rd, Chestertown, MD 21620
      10044 John Carvill (4th Point) Rd, Chestertown, MD 21620
      /85

      Not Listed For Sale

      10044 John Carvill (4th Point) Rd, Chestertown, MD 21620

      • 5 Beds
      • 5 Baths
      • 3,477 Sq Ft
      • Built 1976
      10044 John Carvill (4th Point) Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

    • 237 Island Lark Way, Chestertown, MD 21620
      237 Island Lark Way, Chestertown, MD 21620
      237 Island Lark Way, Chestertown, MD 21620
      /27

      Est $283,757

      Not Listed For Sale

      237 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 2023
      237 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 57 Days On Market

    • 241 Island Lark Way, Chestertown, MD 21620
      241 Island Lark Way, Chestertown, MD 21620
      241 Island Lark Way, Chestertown, MD 21620
      /27

      Est $282,880

      Not Listed For Sale

      241 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 2023
      241 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 83 Days On Market

    • 0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620
      0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620
      0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620
      /4

      Not Listed For Sale

      0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620

      0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620

      Last Sold Summary

      • 179 Days On Market

    • 243 Island Lark Way, Chestertown, MD 21620
      243 Island Lark Way, Chestertown, MD 21620
      243 Island Lark Way, Chestertown, MD 21620
      /27

      Est $297,692

      Not Listed For Sale

      243 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 2023
      243 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 57 Days On Market

    • 239 Island Lark Way, Chestertown, MD 21620
      239 Island Lark Way, Chestertown, MD 21620
      239 Island Lark Way, Chestertown, MD 21620
      /27

      Est $283,536

      Not Listed For Sale

      239 Island Lark Way, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 2023
      239 Island Lark Way, Chestertown, MD 21620

      Last Sold Summary

      • 82 Days On Market

    • 21321 Persimmon Dr, Chestertown, MD 21620
      21321 Persimmon Dr, Chestertown, MD 21620
      21321 Persimmon Dr, Chestertown, MD 21620
      /13

      Est $163,009

      Not Listed For Sale

      21321 Persimmon Dr, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1955
      21321 Persimmon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8 Days On Market

    • 318 Landing Ln Unit 30, Chestertown, MD 21620
      318 Landing Ln Unit 30, Chestertown, MD 21620
      318 Landing Ln Unit 30, Chestertown, MD 21620
      /39

      Est $708,212

      Not Listed For Sale

      318 Landing Ln Unit 30, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • Built 2014
      318 Landing Ln Unit 30, Chestertown, MD 21620

      Last Sold Summary

      • 88 Days On Market

    • 407 S Cross St Unit 4, Chestertown, MD 21620
      407 S Cross St Unit 4, Chestertown, MD 21620
      407 S Cross St Unit 4, Chestertown, MD 21620
      /30

      Est $715,165

      Not Listed For Sale

      407 S Cross St Unit 4, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,183 Sq Ft
      • Built 1996
      407 S Cross St Unit 4, Chestertown, MD 21620

      Last Sold Summary

      • 150 Days On Market

    • 0 Landing Ln Unit 12 MDKE2002644, Chestertown, MD 21620
      0 Landing Ln Unit 12 MDKE2002644, Chestertown, MD 21620
      0 Landing Ln Unit 12 MDKE2002644, Chestertown, MD 21620
      /36

      Not Listed For Sale

      0 Landing Ln Unit 12 MDKE2002644, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      0 Landing Ln Unit 12 MDKE2002644, Chestertown, MD 21620

      Last Sold Summary

      • 330 Days On Market

    • 481 Pear Tree Point Rd, Chestertown, MD 21620
      481 Pear Tree Point Rd, Chestertown, MD 21620
      481 Pear Tree Point Rd, Chestertown, MD 21620
      /22

      Est $395,166

      Not Listed For Sale

      481 Pear Tree Point Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2024
      481 Pear Tree Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 223 Days On Market

    • 477 Pear Tree Point Rd, Chestertown, MD 21620
      477 Pear Tree Point Rd, Chestertown, MD 21620
      477 Pear Tree Point Rd, Chestertown, MD 21620
      /20

      Est $369,670

      Not Listed For Sale

      477 Pear Tree Point Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2024
      477 Pear Tree Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 282 Days On Market

    • 473 Pear Tree Point Rd, Chestertown, MD 21620
      473 Pear Tree Point Rd, Chestertown, MD 21620
      473 Pear Tree Point Rd, Chestertown, MD 21620
      /24

      Est $376,380

      Not Listed For Sale

      473 Pear Tree Point Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,512 Sq Ft
      • Built 2024
      473 Pear Tree Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 67 Days On Market

    • 0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620
      0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620
      0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620
      /8

      Not Listed For Sale

      0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620

      0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620

      Last Sold Summary

      • 726 Days On Market

    • 308 Landing Ln Unit 17, Chestertown, MD 21620
      308 Landing Ln Unit 17, Chestertown, MD 21620
      308 Landing Ln Unit 17, Chestertown, MD 21620
      /6

      Not Listed For Sale

      308 Landing Ln Unit 17, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • Built 2014
      308 Landing Ln Unit 17, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

    • 116 Riverside Terrace Unit 7, Chestertown, MD 21620
      116 Riverside Terrace Unit 7, Chestertown, MD 21620
      116 Riverside Terrace Unit 7, Chestertown, MD 21620
      /38

      Est $381,020

      Not Listed For Sale

      116 Riverside Terrace Unit 7, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 900 Sq Ft
      • Built 1900
      116 Riverside Terrace Unit 7, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

    • 21320 Persimmon Dr, Chestertown, MD 21620
      21320 Persimmon Dr, Chestertown, MD 21620
      21320 Persimmon Dr, Chestertown, MD 21620
      /27

      Est $170,981

      Not Listed For Sale

      21320 Persimmon Dr, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1955
      21320 Persimmon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 24 Days On Market

    • 21336 Persimmon Dr Unit 13, Chestertown, MD 21620
      21336 Persimmon Dr Unit 13, Chestertown, MD 21620
      21336 Persimmon Dr Unit 13, Chestertown, MD 21620
      /41

      Est $189,313

      Not Listed For Sale

      21336 Persimmon Dr Unit 13, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,269 Sq Ft
      • Built 1955
      21336 Persimmon Dr Unit 13, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

    • 21341 Persimmon Dr Unit 17, Chestertown, MD 21620
      21341 Persimmon Dr Unit 17, Chestertown, MD 21620
      21341 Persimmon Dr Unit 17, Chestertown, MD 21620
      /23

      Est $168,334

      Not Listed For Sale

      21341 Persimmon Dr Unit 17, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,269 Sq Ft
      • Built 1955
      21341 Persimmon Dr Unit 17, Chestertown, MD 21620

      Last Sold Summary

      • 206 Days On Market

    • 21313 Persimmon Dr Unit 24, Chestertown, MD 21620
      21313 Persimmon Dr Unit 24, Chestertown, MD 21620
      21313 Persimmon Dr Unit 24, Chestertown, MD 21620
      /16

      Est $193,997

      Not Listed For Sale

      21313 Persimmon Dr Unit 24, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,350 Sq Ft
      • Built 1955
      21313 Persimmon Dr Unit 24, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

    • 101 Landing Ln Unit 39, Chestertown, MD 21620
      101 Landing Ln Unit 39, Chestertown, MD 21620
      101 Landing Ln Unit 39, Chestertown, MD 21620
      /35

      Est $651,573

      Not Listed For Sale

      101 Landing Ln Unit 39, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 3,300 Sq Ft
      • Built 2013
      101 Landing Ln Unit 39, Chestertown, MD 21620

      Last Sold Summary

      • 151 Days On Market

    • 0 Gateway Dr, Chestertown, MD 21620
      0 Gateway Dr, Chestertown, MD 21620
      0 Gateway Dr, Chestertown, MD 21620
      /6

      Not Listed For Sale

      0 Gateway Dr, Chestertown, MD 21620

      0 Gateway Dr, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

    • 210 Truslow Farm Ln, Chestertown, MD 21620
      210 Truslow Farm Ln, Chestertown, MD 21620
      210 Truslow Farm Ln, Chestertown, MD 21620
      /7

      Est $528,000

      Not Listed For Sale

      210 Truslow Farm Ln, Chestertown, MD 21620

      210 Truslow Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 77 Days On Market

Showing Results 641 - 680, Page 17 of 18

Maryland Kent County

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