5,229

Chester, MD Homes

Section Image Section Image
  • 1803 Chester Dr, Chester, MD 21619
    1803 Chester Dr, Chester, MD 21619
    1803 Chester Dr, Chester, MD 21619
    /29

    $385,000

    Sold May 09, 2026

    1803 Chester Dr, Chester, MD 21619

    • 4 Beds
    • 2 Baths
    • 1,636 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $235/SF
    • 3 Days On Market

    Current Estimated Value $388,815

    Last Listing Agent Jennifer Kramer-Dela Cruz Keller Williams Legacy

    1803 Chester Dr, Chester, MD 21619
    • 1832 Saint Marys Rd, Chester, MD 21619
      1832 Saint Marys Rd, Chester, MD 21619
      1832 Saint Marys Rd, Chester, MD 21619
      /32

      Est $1,111,505

      Not Listed For Sale

      1832 Saint Marys Rd, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,140 Sq Ft
      • Built 1999
      1832 Saint Marys Rd, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jamil Wright EXP Realty, LLC

  • 104 Golden Eye Ct, Chester, MD 21619
    104 Golden Eye Ct, Chester, MD 21619
    104 Golden Eye Ct, Chester, MD 21619
    /30

    $300,000

    Sold Dec 11, 2025

    104 Golden Eye Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 2000

    Last Sold Summary

    • $280/SF
    • 19 Days On Market

    Current Estimated Value $287,693

    Last Listing Agent Terri Murray RE/MAX Executive

    104 Golden Eye Ct, Chester, MD 21619
    • 208 Merganser Ct, Chester, MD 21619
      208 Merganser Ct, Chester, MD 21619
      208 Merganser Ct, Chester, MD 21619
      /8

      Est $282,132

      Not Listed For Sale

      208 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,073 Sq Ft
      • Built 1998
      208 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Regina Fischer Long & Foster Real Estate, Inc.

  • 109 Price Rd, Chester, MD 21619
    109 Price Rd, Chester, MD 21619
    /2

    $435,100

    Sold Apr 08, 2026

    109 Price Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,466 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Above List Price
    • $297/SF
    • 2 Days On Market

    Current Estimated Value $435,608

    Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    109 Price Rd, Chester, MD 21619
    • 1752 Harbor Dr, Chester, MD 21619
      1752 Harbor Dr, Chester, MD 21619
      1752 Harbor Dr, Chester, MD 21619
      /62

      Est $476,538

      Not Listed For Sale

      1752 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 2,100 Sq Ft
      • Built 1954
      1752 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Martin Farmer Cummings & Co. Realtors

  • 164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    /25

    $879,900

    Sold Sep 09, 2025

    164 Redstart Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $317/SF
    • 6 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    164 Redstart Dr, Chester, MD 21619
    • 2655 Cox Neck Rd, Chester, MD 21619
      2655 Cox Neck Rd, Chester, MD 21619
      2655 Cox Neck Rd, Chester, MD 21619
      /32

      Est $417,990

      Not Listed For Sale

      2655 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,770 Sq Ft
      • Built 1975
      2655 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Mark Milligan RE/Max Experience

  • 308 Dominion Rd, Chester, MD 21619
    308 Dominion Rd, Chester, MD 21619
    308 Dominion Rd, Chester, MD 21619
    /35

    $325,000

    Sold Sep 17, 2025

    308 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Built 1955

    Last Sold Summary

    • $254/SF
    • 193 Days On Market

    Current Estimated Value $340,879

    Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

    308 Dominion Rd, Chester, MD 21619
    • 1715 Little Creek Rd, Chester, MD 21619
      1715 Little Creek Rd, Chester, MD 21619
      1715 Little Creek Rd, Chester, MD 21619
      /58

      Est $685,498

      Not Listed For Sale

      1715 Little Creek Rd, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,726 Sq Ft
      • Built 1953
      1715 Little Creek Rd, Chester, MD 21619

      Last Sold Summary

      • 103 Days On Market

      Last Listing Agent Bill Beam Beam Realty Group, Inc.

  • 133 Henry Stoupe Way, Chester, MD 21619
    133 Henry Stoupe Way, Chester, MD 21619
    133 Henry Stoupe Way, Chester, MD 21619
    /72

    $960,000

    Sold Aug 08, 2025

    133 Henry Stoupe Way, Chester, MD 21619

    • 6 Beds
    • 4.5 Baths
    • 3,541 Sq Ft
    • Built 2011

    Last Sold Summary

    • $271/SF
    • 4 Days On Market

    Current Estimated Value $995,622

    Last Listing Agent Tara Trout Samson Properties

    133 Henry Stoupe Way, Chester, MD 21619
    • 5010 Bridgepointe Dr, Chester, MD 21619
      5010 Bridgepointe Dr, Chester, MD 21619
      5010 Bridgepointe Dr, Chester, MD 21619
      /52

      Est $405,294

      Not Listed For Sale

      5010 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,635 Sq Ft
      • Built 1995
      5010 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Lamar Braithwaite Coldwell Banker Realty - Washington

  • 330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    /55

    $989,000

    Sold Sep 11, 2025

    330 Macum Creek Dr, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 3,949 Sq Ft
    • Built 2015

    Last Sold Summary

    • $250/SF
    • 27 Days On Market

    Current Estimated Value $999,570

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    330 Macum Creek Dr, Chester, MD 21619
    • 1435 Cox Neck Rd, Chester, MD 21619
      1435 Cox Neck Rd, Chester, MD 21619
      1435 Cox Neck Rd, Chester, MD 21619
      /29

      Est $400,804

      Not Listed For Sale

      1435 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,104 Sq Ft
      • Built 1975
      1435 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Bevia Patrick Keller Williams Flagship

  • 102 Boatswain Way Unit 24, Chester, MD 21619
    102 Boatswain Way Unit 24, Chester, MD 21619
    102 Boatswain Way Unit 24, Chester, MD 21619
    /21

    $819,990

    Sold Jul 15, 2026

    102 Boatswain Way Unit 24, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $315/SF
    • 55 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    102 Boatswain Way Unit 24, Chester, MD 21619
    • 2861 Cox Neck Rd, Chester, MD 21619
      2861 Cox Neck Rd, Chester, MD 21619
      2861 Cox Neck Rd, Chester, MD 21619
      /79

      Est $1,850,979

      Not Listed For Sale

      2861 Cox Neck Rd, Chester, MD 21619

      • 5 Beds
      • 2.5 Baths
      • 3,716 Sq Ft
      • Built 1997
      2861 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

  • 137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    /81

    $721,000

    Sold Sep 16, 2025

    137 Warbler Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 2,147 Sq Ft
    • Built 2024

    Last Sold Summary

    • $336/SF
    • 129 Days On Market

    Last Listing Agent Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Chester, MD 21619
    • 1702 Harbor Dr, Chester, MD 21619
      1702 Harbor Dr, Chester, MD 21619
      1702 Harbor Dr, Chester, MD 21619
      /36

      Est $336,879

      Not Listed For Sale

      1702 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 980 Sq Ft
      • Built 1949
      1702 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Michael Roenigk Chaney Homes, LLC

  • 110 Boatswain Way Unit 33, Chester, MD 21619
    110 Boatswain Way Unit 33, Chester, MD 21619
    110 Boatswain Way Unit 33, Chester, MD 21619
    /28

    $699,990

    Sold Apr 01, 2026

    110 Boatswain Way Unit 33, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 11% Below List Price
    • $368/SF
    • 14 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 33, Chester, MD 21619
    • 2601 Ellicott Dr, Chester, MD 21619
      2601 Ellicott Dr, Chester, MD 21619
      2601 Ellicott Dr, Chester, MD 21619
      /26

      Est $381,897

      Not Listed For Sale

      2601 Ellicott Dr, Chester, MD 21619

      • 3 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 1974
      2601 Ellicott Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Jarnell Foster Samson Properties

  • 202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    /72

    $335,000

    Sold Sep 05, 2025

    202 Ringneck Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,956 Sq Ft
    • Built 1995

    Last Sold Summary

    • $171/SF
    • 94 Days On Market

    Current Estimated Value $341,184

    Last Listing Agent Sheila Washburn Benson & Mangold, LLC

    202 Ringneck Ct, Chester, MD 21619
    • 1712 Bayside Dr, Chester, MD 21619
      1712 Bayside Dr, Chester, MD 21619
      1712 Bayside Dr, Chester, MD 21619
      /73

      Est $1,111,259

      Not Listed For Sale

      1712 Bayside Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,616 Sq Ft
      • Built 1977
      1712 Bayside Dr, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

  • 1906 Stevens Dr, Chester, MD 21619
    1906 Stevens Dr, Chester, MD 21619
    1906 Stevens Dr, Chester, MD 21619
    /49

    $471,500

    Sold Jun 30, 2026

    1906 Stevens Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $234/SF
    • 22 Days On Market

    Current Estimated Value $462,863

    Last Listing Agent Terri Murray RE/MAX Executive

    1906 Stevens Dr, Chester, MD 21619
    • 212 Ringneck Ct, Chester, MD 21619
      212 Ringneck Ct, Chester, MD 21619
      212 Ringneck Ct, Chester, MD 21619
      /44

      Est $376,605

      Not Listed For Sale

      212 Ringneck Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,747 Sq Ft
      • Built 1995
      212 Ringneck Ct, Chester, MD 21619

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Michael Rosendale Rosendale Realty

  • 1604 Midway Rd, Chester, MD 21619
    1604 Midway Rd, Chester, MD 21619
    1604 Midway Rd, Chester, MD 21619
    /73

    $800,000

    Sold May 15, 2026

    1604 Midway Rd, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,972 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Above List Price
    • $269/SF
    • 7 Days On Market

    Current Estimated Value $807,445

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    1604 Midway Rd, Chester, MD 21619
    • 29H Queen Mary Ct, Chester, MD 21619
      29H Queen Mary Ct, Chester, MD 21619
      29H Queen Mary Ct, Chester, MD 21619
      /28

      Est $383,298

      Not Listed For Sale

      29H Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1999
      29H Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Anita Snyder Star Realty

  • 176 Flagstaff Way Unit 43, Chester, MD 21619
    176 Flagstaff Way Unit 43, Chester, MD 21619
    176 Flagstaff Way Unit 43, Chester, MD 21619
    /29

    $979,990

    Sold Mar 16, 2026

    176 Flagstaff Way Unit 43, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 4% Below List Price
    • $516/SF
    • 10 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    176 Flagstaff Way Unit 43, Chester, MD 21619
    • 45H Queen Neva Ct, Chester, MD 21619
      45H Queen Neva Ct, Chester, MD 21619
      45H Queen Neva Ct, Chester, MD 21619
      /31

      Est $454,781

      Not Listed For Sale

      45H Queen Neva Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,842 Sq Ft
      • Built 1995
      45H Queen Neva Ct, Chester, MD 21619

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Jimmy White Long & Foster Real Estate, Inc.

  • 2817 Cox Neck Rd, Chester, MD 21619
    2817 Cox Neck Rd, Chester, MD 21619
    2817 Cox Neck Rd, Chester, MD 21619
    /35

    $1,850,000

    Sold Nov 14, 2025

    2817 Cox Neck Rd, Chester, MD 21619

    • 6 Beds
    • 5.5 Baths
    • 5,174 Sq Ft
    • Built 2002

    Last Sold Summary

    • $358/SF
    • 561 Days On Market

    Current Estimated Value $1,959,399

    Last Listing Agent Michael Bozek Michael J. Bozek

    2817 Cox Neck Rd, Chester, MD 21619
    • 51D Queen Caroline Ct, Chester, MD 21619
      51D Queen Caroline Ct, Chester, MD 21619
      51D Queen Caroline Ct, Chester, MD 21619
      /76

      Est $461,237

      Not Listed For Sale

      51D Queen Caroline Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1995
      51D Queen Caroline Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • 202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    /63

    $825,000

    Sold Mar 30, 2026

    202 Mchenny Ct, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft
    • Built 2012

    Last Sold Summary

    • $327/SF
    • 79 Days On Market

    Current Estimated Value $816,873

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    202 Mchenny Ct, Chester, MD 21619
    • 6011 Bridgepointe Dr, Chester, MD 21619
      6011 Bridgepointe Dr, Chester, MD 21619
      6011 Bridgepointe Dr, Chester, MD 21619
      /29

      Est $376,191

      Not Listed For Sale

      6011 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,635 Sq Ft
      • Built 1992
      6011 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Jennifer Angel-Fuhlman Coldwell Banker Realty

  • 176 Flagstaff Way Unit 24, Chester, MD 21619
    176 Flagstaff Way Unit 24, Chester, MD 21619
    176 Flagstaff Way Unit 24, Chester, MD 21619
    /18

    $935,990

    Sold Jan 21, 2026

    176 Flagstaff Way Unit 24, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $360/SF
    • 12 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    176 Flagstaff Way Unit 24, Chester, MD 21619
    • 1921 Stevens Dr, Chester, MD 21619
      1921 Stevens Dr, Chester, MD 21619
      1921 Stevens Dr, Chester, MD 21619
      /27

      Est $380,793

      Not Listed For Sale

      1921 Stevens Dr, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,484 Sq Ft
      • Built 1990
      1921 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Justin Disborough Samson Properties

  • 327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    /38

    $949,900

    Sold Aug 26, 2025

    327 Kingfisher Ln, Chester, MD 21619

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $295/SF
    • 7 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    327 Kingfisher Ln, Chester, MD 21619
    • 32F Queen Anne Way, Chester, MD 21619
      32F Queen Anne Way, Chester, MD 21619
      32F Queen Anne Way, Chester, MD 21619
      /61

      Est $565,849

      Not Listed For Sale

      32F Queen Anne Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1983
      32F Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent The Williams Home Team Douglas Realty, LLC

  • 830 Warbler Way Unit 32, Chester, MD 21619
    830 Warbler Way Unit 32, Chester, MD 21619
    830 Warbler Way Unit 32, Chester, MD 21619
    /28

    $719,815

    Sold Jul 31, 2026

    830 Warbler Way Unit 32, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $379/SF
    • 23 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    830 Warbler Way Unit 32, Chester, MD 21619
    • 32B Queen Anne Way, Chester, MD 21619
      32B Queen Anne Way, Chester, MD 21619
      32B Queen Anne Way, Chester, MD 21619
      /37

      Est $302,699

      Not Listed For Sale

      32B Queen Anne Way, Chester, MD 21619

      • 1 Bed
      • 1 Bath
      • 724 Sq Ft
      • Built 1983
      32B Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • 630 Warbler Way Unit 2233, Chester, MD 21619
    630 Warbler Way Unit 2233, Chester, MD 21619
    630 Warbler Way Unit 2233, Chester, MD 21619
    /48

    $599,900

    Sold May 29, 2026

    630 Warbler Way Unit 2233, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $316/SF
    • 75 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2233, Chester, MD 21619
    • 2904 Cox Neck Rd E, Chester, MD 21619
      2904 Cox Neck Rd E, Chester, MD 21619
      2904 Cox Neck Rd E, Chester, MD 21619
      /42

      Est $1,200,873

      Not Listed For Sale

      2904 Cox Neck Rd E, Chester, MD 21619

      • 4 Beds
      • 4.5 Baths
      • 4,613 Sq Ft
      • Built 1996
      2904 Cox Neck Rd E, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

Showing Results 441 - 480, Page 12 of 18

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