6,869

Chestertown, MD Homes

Section Image
    • 111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      /44

      Est $409,963 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      111 Manor Ave, Chestertown, MD 21620

      111 Manor Ave, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $475,000 Sold Dec 11, 2025

    101 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • Built 1979

    Last Sold Summary

    • $242/SF
    • 38 Days On Market

    Last Listing Agent Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
    • 631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      /9

      Est $246,052 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,234 Sq Ft

      631 High St, Chestertown, MD 21620

      631 High St, Chestertown, MD 21620
  • 7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    /56

    $759,000 Sold Jul 01, 2025

    7988 Aldan Dr, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft
    • Built 2000

    Last Sold Summary

    • $224/SF
    • 2 Days On Market

    Current Estimated Value $758,830

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
    • 207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      /44

      Est $598,574 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft

      207 N Queen St, Chestertown, MD 21620

      207 N Queen St, Chestertown, MD 21620
  • 726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    /35

    $485,960 Sold Oct 31, 2025

    726 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $229/SF
    • 14 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    726 Aldora Dr, Chestertown, MD 21620
    • 7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      /13

      Est $831,755 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,322 Sq Ft

      7694 Waterview Ln, Chestertown, MD 21620

      7694 Waterview Ln, Chestertown, MD 21620
  • 10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    /20

    $246,000 Sold Aug 15, 2025

    10624 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $246/SF
    • 17 Days On Market

    Current Estimated Value $241,239

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
    • 10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      /50

      Est $1,345,762 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,345 Sq Ft

      10705 Tilden Ln, Chestertown, MD 21620

      10705 Tilden Ln, Chestertown, MD 21620
  • 213 N Queen St, Chestertown, MD 21620
    213 N Queen St, Chestertown, MD 21620
    213 N Queen St, Chestertown, MD 21620
    /3

    $675,000 Sold Jun 25, 2025

    213 N Queen St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,945 Sq Ft
    • Built 1904

    Last Sold Summary

    • $347/SF
    • 2 Days On Market

    Current Estimated Value $668,063

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
    • 215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      /30

      Est $366,864 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft

      215 Devon Dr, Chestertown, MD 21620

      215 Devon Dr, Chestertown, MD 21620
  • 9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    /45

    $705,000 Sold Sep 26, 2025

    9194 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 1939

    Last Sold Summary

    • $483/SF
    • 19 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    9194 N Bayview Ave, Chestertown, MD 21620
    • 110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      /69

      Est $518,815 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft

      110 Camelot Dr, Chestertown, MD 21620

      110 Camelot Dr, Chestertown, MD 21620
  • 10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    /43

    $262,500 Sold May 29, 2025

    10705 Millbrook Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft
    • Built 1988

    Last Sold Summary

    • $125/SF
    • 87 Days On Market

    Current Estimated Value $374,044

    Last Listing Agent Edward Kowalski EXP Realty, LLC

    10705 Millbrook Dr, Chestertown, MD 21620
    • 103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      /31

      Est $355,254 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft

      103 Trafford Dr, Chestertown, MD 21620

      103 Trafford Dr, Chestertown, MD 21620
  • 101 Rivershore Rd, Chestertown, MD 21620
    101 Rivershore Rd, Chestertown, MD 21620
    /2

    $1,125,000 Sold Jun 10, 2025

    101 Rivershore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,968 Sq Ft
    • Built 1950

    Last Sold Summary

    • $572/SF

    Current Estimated Value $1,004,039

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 Rivershore Rd, Chestertown, MD 21620
    • 208 N Mill St, Chestertown, MD 21620
      208 N Mill St, Chestertown, MD 21620
      208 N Mill St, Chestertown, MD 21620
      /41

      Est $392,105 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,537 Sq Ft

      208 N Mill St, Chestertown, MD 21620

      208 N Mill St, Chestertown, MD 21620
  • 200 Fey Rd, Chestertown, MD 21620
    200 Fey Rd, Chestertown, MD 21620
    200 Fey Rd, Chestertown, MD 21620
    /18

    $375,000 Sold Oct 10, 2025

    200 Fey Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1996

    Last Sold Summary

    • $239/SF
    • 19 Days On Market

    Last Listing Agent Erik Hoferer Long & Foster Real Estate, Inc.

    200 Fey Rd, Chestertown, MD 21620
    • 503 N Kent St, Chestertown, MD 21620
      503 N Kent St, Chestertown, MD 21620
      503 N Kent St, Chestertown, MD 21620
      /26

      Est $365,171 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft

      503 N Kent St, Chestertown, MD 21620

      503 N Kent St, Chestertown, MD 21620
  • 205 Pine St, Chestertown, MD 21620
    205 Pine St, Chestertown, MD 21620
    205 Pine St, Chestertown, MD 21620
    /23

    $296,337 Sold Sep 30, 2025

    205 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft
    • Built 1955

    Last Sold Summary

    • $134/SF
    • 32 Days On Market

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, Chestertown, MD 21620
    • 202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      /34

      Est $405,180 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft

      202 Byford Dr, Chestertown, MD 21620

      202 Byford Dr, Chestertown, MD 21620
  • 716 Aldora Dr, Chestertown, MD 21620
    716 Aldora Dr, Chestertown, MD 21620
    716 Aldora Dr, Chestertown, MD 21620
    /35

    $510,184 Sold May 29, 2025

    716 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $241/SF
    • 0 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    716 Aldora Dr, Chestertown, MD 21620
    • 7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      /65

      Est $1,037,519 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,730 Sq Ft

      7755 Waterview Ln, Chestertown, MD 21620

      7755 Waterview Ln, Chestertown, MD 21620
  • 10715 Kasota Rd, Chestertown, MD 21620
    10715 Kasota Rd, Chestertown, MD 21620
    10715 Kasota Rd, Chestertown, MD 21620
    /49

    $960,000 Sold Aug 27, 2025

    10715 Kasota Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,401 Sq Ft
    • Built 2005

    Last Sold Summary

    • $282/SF
    • 5 Days On Market

    Current Estimated Value $958,914

    Last Listing Agent Sarah King Cross Street Realtors LLC

    10715 Kasota Rd, Chestertown, MD 21620
    • 9088 Point Ln, Chestertown, MD 21620
      9088 Point Ln, Chestertown, MD 21620
      9088 Point Ln, Chestertown, MD 21620
      /69

      Est $1,263,054 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      9088 Point Ln, Chestertown, MD 21620

      9088 Point Ln, Chestertown, MD 21620
  • 200 Hoffman Ln, Chestertown, MD 21620
    200 Hoffman Ln, Chestertown, MD 21620
    200 Hoffman Ln, Chestertown, MD 21620
    /8

    $360,000 Sold Jun 27, 2025

    200 Hoffman Ln, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1957

    Last Sold Summary

    • $319/SF
    • 15 Days On Market

    Current Estimated Value $405,700

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    200 Hoffman Ln, Chestertown, MD 21620
    • 7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      /22

      Est $507,044 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft

      7920 Carriage Ln, Chestertown, MD 21620

      7920 Carriage Ln, Chestertown, MD 21620
  • 7682 Waterview Ln, Chestertown, MD 21620
    7682 Waterview Ln, Chestertown, MD 21620
    7682 Waterview Ln, Chestertown, MD 21620
    /32

    $645,000 Sold Jul 31, 2025

    7682 Waterview Ln, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,240 Sq Ft
    • Built 1989

    Last Sold Summary

    • $288/SF
    • 2 Days On Market

    Current Estimated Value $647,874

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7682 Waterview Ln, Chestertown, MD 21620
    • 209 E Campus Ave, Chestertown, MD 21620
      209 E Campus Ave, Chestertown, MD 21620
      209 E Campus Ave, Chestertown, MD 21620
      /34

      Est $490,107 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft

      209 E Campus Ave, Chestertown, MD 21620

      209 E Campus Ave, Chestertown, MD 21620
  • 9020 Georgetown Rd, Chestertown, MD 21620
    9020 Georgetown Rd, Chestertown, MD 21620
    9020 Georgetown Rd, Chestertown, MD 21620
    /10

    $65,000 Sold Aug 11, 2025

    9020 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 2.36 Acres
    • $27,542 per Acre

    Last Sold Summary

    • 54 Days On Market

    Current Estimated Value $64,647

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    9020 Georgetown Rd, Chestertown, MD 21620
    • 25819 Collins Ave, Chestertown, MD 21620
      25819 Collins Ave, Chestertown, MD 21620
      25819 Collins Ave, Chestertown, MD 21620
      /55

      Est $635,614 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,952 Sq Ft

      25819 Collins Ave, Chestertown, MD 21620

      25819 Collins Ave, Chestertown, MD 21620
  • 0 Truslow Farm Ln, Chestertown, MD 21620
    0 Truslow Farm Ln, Chestertown, MD 21620
    0 Truslow Farm Ln, Chestertown, MD 21620
    /10

    $390,000 Sold Feb 06, 2025

    0 Truslow Farm Ln, Chestertown, MD 21620

    • Land
    • 2.3 Acres
    • $169,565 per Acre

    Last Sold Summary

    • 322 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Truslow Farm Ln, Chestertown, MD 21620
    • 9545 Chantilly Farm Ln, Chestertown, MD 21620
      9545 Chantilly Farm Ln, Chestertown, MD 21620
      9545 Chantilly Farm Ln, Chestertown, MD 21620
      /64

      Est $1,437,636 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      9545 Chantilly Farm Ln, Chestertown, MD 21620
  • 201 Pondview Ct, Chestertown, MD 21620
    201 Pondview Ct, Chestertown, MD 21620
    201 Pondview Ct, Chestertown, MD 21620
    /37

    $525,000 Sold Jun 30, 2025

    201 Pondview Ct, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,016 Sq Ft
    • Built 2001

    Last Sold Summary

    • $174/SF
    • 2 Days On Market

    Current Estimated Value $537,031

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    201 Pondview Ct, Chestertown, MD 21620
    • 7898 Radcliffe Rd, Chestertown, MD 21620
      7898 Radcliffe Rd, Chestertown, MD 21620
      7898 Radcliffe Rd, Chestertown, MD 21620
      /46

      Est $556,450 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,264 Sq Ft

      7898 Radcliffe Rd, Chestertown, MD 21620

      7898 Radcliffe Rd, Chestertown, MD 21620
  • 5594 Langford Bay Rd, Chestertown, MD 21620
    5594 Langford Bay Rd, Chestertown, MD 21620
    5594 Langford Bay Rd, Chestertown, MD 21620
    /40

    $750,000 Sold May 22, 2025

    5594 Langford Bay Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft
    • Built 1956

    Last Sold Summary

    • $446/SF
    • 0 Days On Market

    Current Estimated Value $750,648

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, Chestertown, MD 21620
    • 5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      /44

      Est $581,264 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
  • 201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    /46

    $425,000 Sold Nov 17, 2025

    201 Boundary Ave, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1968

    Last Sold Summary

    • $137/SF
    • 59 Days On Market

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
    • 8500 Broad Neck Rd, Chestertown, MD 21620
      8500 Broad Neck Rd, Chestertown, MD 21620
      8500 Broad Neck Rd, Chestertown, MD 21620
      /25

      Est $501,092 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft

      8500 Broad Neck Rd, Chestertown, MD 21620

      8500 Broad Neck Rd, Chestertown, MD 21620
  • 216 Silver Heel Rd, Chestertown, MD 21620
    216 Silver Heel Rd, Chestertown, MD 21620
    216 Silver Heel Rd, Chestertown, MD 21620
    /32

    $360,000 Sold Jun 12, 2025

    216 Silver Heel Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2022

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $362,191

    Last Listing Agent Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620

Showing Results 361 - 400, Page 10 of 18

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