5,228

Chester, MD Homes

Section Image Section Image
    • 2869 Cox Neck Rd, Chester, MD 21619
      2869 Cox Neck Rd, Chester, MD 21619
      2869 Cox Neck Rd, Chester, MD 21619
      /57

      Est $2,039,691

      Not Listed For Sale

      2869 Cox Neck Rd, Chester, MD 21619

      • 4 Beds
      • 4.5 Baths
      • 3,633 Sq Ft
      • Built 1994
      2869 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Michele Sinclair Long & Foster Real Estate, Inc.

  • 444 Macum Creek Dr, Chester, MD 21619
    444 Macum Creek Dr, Chester, MD 21619
    444 Macum Creek Dr, Chester, MD 21619
    /75

    $840,000

    Sold Oct 22, 2025

    444 Macum Creek Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,771 Sq Ft
    • Built 2012

    Last Sold Summary

    • $303/SF
    • 9 Days On Market

    Current Estimated Value $862,337

    Last Listing Agent Deborah Savoie Long & Foster Real Estate, Inc.

    444 Macum Creek Dr, Chester, MD 21619
    • 309 Bentons Pleasure Rd, Chester, MD 21619
      309 Bentons Pleasure Rd, Chester, MD 21619
      309 Bentons Pleasure Rd, Chester, MD 21619
      /10

      Est $540,961

      Not Listed For Sale

      309 Bentons Pleasure Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,878 Sq Ft
      • Built 1996
      309 Bentons Pleasure Rd, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • 170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    /81

    $665,000

    Sold Feb 27, 2026

    170 Harrier Way Unit 34, Chester, MD 21619

    • 3 Beds
    • 2,602 Sq Ft
    • Built 2022

    Last Sold Summary

    • 5% Below List Price
    • $256/SF
    • 26 Days On Market

    Current Estimated Value $652,605

    Last Listing Agent Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
    • 3F Queen Victoria Ct, Chester, MD 21619
      3F Queen Victoria Ct, Chester, MD 21619
      3F Queen Victoria Ct, Chester, MD 21619
      /29

      Est $251,954

      Not Listed For Sale

      3F Queen Victoria Ct, Chester, MD 21619

      • 1 Bed
      • 1 Bath
      • 724 Sq Ft
      • Built 1983
      3F Queen Victoria Ct, Chester, MD 21619

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

  • 47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    /44

    $549,500

    Sold Jan 30, 2026

    47 D Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Built 1993

    Last Sold Summary

    • $355/SF
    • 68 Days On Market

    Last Listing Agent Brenda Fornos Taylor Properties

    47 D Queen Anne Way, Chester, MD 21619
    • 22A Queen Victoria Way, Chester, MD 21619
      22A Queen Victoria Way, Chester, MD 21619
      22A Queen Victoria Way, Chester, MD 21619
      /69

      Est $409,982

      Not Listed For Sale

      22A Queen Victoria Way, Chester, MD 21619

      • 1 Bed
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1985
      22A Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • 1019 Dominion Rd, Chester, MD 21619
    1019 Dominion Rd, Chester, MD 21619
    /2

    $340,000

    Sold Aug 15, 2025

    1019 Dominion Rd, Chester, MD 21619

    • 1 Bed
    • 1 Bath
    • 1,008 Sq Ft
    • Built 2005

    Last Sold Summary

    • $337/SF
    • 81 Days On Market

    Last Listing Agent Lisa Lynch Keller Williams Realty

    1019 Dominion Rd, Chester, MD 21619
    • 101 Kirwans Landing Ln, Chester, MD 21619
      101 Kirwans Landing Ln, Chester, MD 21619
      101 Kirwans Landing Ln, Chester, MD 21619
      /10

      Est $872,496

      Not Listed For Sale

      101 Kirwans Landing Ln, Chester, MD 21619

      • 5 Beds
      • 2.5 Baths
      • 3,048 Sq Ft
      • Built 1994
      101 Kirwans Landing Ln, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /79

    $524,500

    Sold Mar 30, 2026

    49 Queen Guinivere Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1994

    Last Sold Summary

    • $328/SF
    • 131 Days On Market

    Current Estimated Value $497,956

    Last Listing Agent Julia Stevens Realty Navigator

    49 Queen Guinivere Way, Chester, MD 21619
    • 116 Kirwans Landing Ln, Chester, MD 21619
      116 Kirwans Landing Ln, Chester, MD 21619
      116 Kirwans Landing Ln, Chester, MD 21619
      /68

      Est $1,156,238

      Not Listed For Sale

      116 Kirwans Landing Ln, Chester, MD 21619

      • 5 Beds
      • 4.5 Baths
      • 3,736 Sq Ft
      • Built 2000
      116 Kirwans Landing Ln, Chester, MD 21619

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Michelle Abplanalp Rosendale Realty

  • 7C Queen Victoria Way, Chester, MD 21619
    7C Queen Victoria Way, Chester, MD 21619
    7C Queen Victoria Way, Chester, MD 21619
    /68

    $237,000

    Sold Aug 29, 2025

    7C Queen Victoria Way, Chester, MD 21619

    • Studio
    • 1 Bath
    • 724 Sq Ft
    • Built 1983

    Last Sold Summary

    • $327/SF
    • 128 Days On Market

    Current Estimated Value $236,329

    Last Listing Agent Julia Stevens Realty Navigator

    7C Queen Victoria Way, Chester, MD 21619
    • 1A Queen Victoria Ct, Chester, MD 21619
      1A Queen Victoria Ct, Chester, MD 21619
      1A Queen Victoria Ct, Chester, MD 21619
      /35

      Est $311,427

      Not Listed For Sale

      1A Queen Victoria Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1983
      1A Queen Victoria Ct, Chester, MD 21619

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Rick Parreco RE/MAX Executive

  • 108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    /49

    $499,000

    Sold Dec 23, 2025

    108 Bodys Neck Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft
    • Built 1992

    Last Sold Summary

    • $279/SF
    • 91 Days On Market

    Current Estimated Value $485,415

    Last Listing Agent Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
    • 121 Gunners Rest Ln, Chester, MD 21619
      121 Gunners Rest Ln, Chester, MD 21619
      121 Gunners Rest Ln, Chester, MD 21619
      /44

      Est $1,045,736

      Not Listed For Sale

      121 Gunners Rest Ln, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 3,160 Sq Ft
      • Built 1983
      121 Gunners Rest Ln, Chester, MD 21619

      Last Sold Summary

      Last Listing Agent datacorrect BrightMLS Non Subscribing Office

  • 170 Harrier Way Unit 33, Chester, MD 21619
    170 Harrier Way Unit 33, Chester, MD 21619
    170 Harrier Way Unit 33, Chester, MD 21619
    /41

    $485,000

    Sold Oct 30, 2025

    170 Harrier Way Unit 33, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2022

    Last Sold Summary

    • $255/SF
    • 254 Days On Market

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    170 Harrier Way Unit 33, Chester, MD 21619
    • 228 Bentons Pleasure Rd, Chester, MD 21619
      228 Bentons Pleasure Rd, Chester, MD 21619
      228 Bentons Pleasure Rd, Chester, MD 21619
      /73

      Est $1,470,064

      Not Listed For Sale

      228 Bentons Pleasure Rd, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,571 Sq Ft
      • Built 2005
      228 Bentons Pleasure Rd, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

  • 259 Redstart Dr, Chester, MD 21619
    259 Redstart Dr, Chester, MD 21619
    259 Redstart Dr, Chester, MD 21619
    /11

    $799,990

    Sold Feb 26, 2026

    259 Redstart Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 4% Below List Price
    • $287/SF
    • 6 Days On Market

    Current Estimated Value $802,458

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

    259 Redstart Dr, Chester, MD 21619
    • 237 Bentons Pleasure Rd, Chester, MD 21619
      237 Bentons Pleasure Rd, Chester, MD 21619
      237 Bentons Pleasure Rd, Chester, MD 21619
      /40

      Est $521,787

      Not Listed For Sale

      237 Bentons Pleasure Rd, Chester, MD 21619

      • 5 Beds
      • 3 Baths
      • 2,184 Sq Ft
      • Built 1975
      237 Bentons Pleasure Rd, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Scott Swahl Redfin Corp

  • 7014 Bridgepointe Dr, Chester, MD 21619
    7014 Bridgepointe Dr, Chester, MD 21619
    /2

    $363,000

    Sold Dec 09, 2025

    7014 Bridgepointe Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft
    • Built 1993

    Last Sold Summary

    • $222/SF
    • 88 Days On Market

    Current Estimated Value $359,851

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    7014 Bridgepointe Dr, Chester, MD 21619
    • 103 Old Point Rd, Chester, MD 21619
      103 Old Point Rd, Chester, MD 21619
      103 Old Point Rd, Chester, MD 21619
      /68

      Est $563,460

      Not Listed For Sale

      103 Old Point Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 1987
      103 Old Point Rd, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Lona Todd Taylor Properties

  • 201 Switchgrass Way Unit 43, Chester, MD 21619
    201 Switchgrass Way Unit 43, Chester, MD 21619
    201 Switchgrass Way Unit 43, Chester, MD 21619
    /25

    $784,900

    Sold Aug 20, 2025

    201 Switchgrass Way Unit 43, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $413/SF
    • 31 Days On Market

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

    201 Switchgrass Way Unit 43, Chester, MD 21619
    • 104 Barren Ridge Rd, Chester, MD 21619
      104 Barren Ridge Rd, Chester, MD 21619
      104 Barren Ridge Rd, Chester, MD 21619
      /41

      Est $454,207

      Not Listed For Sale

      104 Barren Ridge Rd, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 2,055 Sq Ft
      • Built 1979
      104 Barren Ridge Rd, Chester, MD 21619

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Martha Brown Long & Foster Real Estate, Inc.

  • 129 Sailcloth Way, Chester, MD 21619
    129 Sailcloth Way, Chester, MD 21619
    129 Sailcloth Way, Chester, MD 21619
    /54

    $764,900

    Sold May 22, 2026

    129 Sailcloth Way, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 2,303 Sq Ft
    • Built 2021

    Last Sold Summary

    • $332/SF
    • 3 Days On Market

    Current Estimated Value $763,431

    Last Listing Agent Catherine Watson - Bye RE/MAX Executive

    129 Sailcloth Way, Chester, MD 21619
    • 1830 Sherman Dr, Chester, MD 21619
      1830 Sherman Dr, Chester, MD 21619
      1830 Sherman Dr, Chester, MD 21619
      /20

      Est $465,515

      Not Listed For Sale

      1830 Sherman Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,176 Sq Ft
      • Built 1988
      1830 Sherman Dr, Chester, MD 21619

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Stan Rehn Douglas Realty LLC

  • 235 Bayberry Dr, Chester, MD 21619
    235 Bayberry Dr, Chester, MD 21619
    235 Bayberry Dr, Chester, MD 21619
    /70

    $910,000

    Sold Oct 03, 2025

    235 Bayberry Dr, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 3,514 Sq Ft
    • Built 2021

    Last Sold Summary

    • $259/SF
    • 62 Days On Market

    Current Estimated Value $944,226

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    235 Bayberry Dr, Chester, MD 21619
    • 1816 Stevens Dr, Chester, MD 21619
      1816 Stevens Dr, Chester, MD 21619
      1816 Stevens Dr, Chester, MD 21619
      /40

      Est $496,936

      Not Listed For Sale

      1816 Stevens Dr, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,930 Sq Ft
      • Built 1989
      1816 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Christian Schou TTR Sotheby's International Realty

  • 255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    /56

    $898,000

    Sold Oct 01, 2025

    255 Sailcloth Way, Chester, MD 21619

    • 4 Beds
    • 4 Baths
    • 3,450 Sq Ft
    • Built 2021

    Last Sold Summary

    • $260/SF
    • 36 Days On Market

    Current Estimated Value $930,562

    Last Listing Agent Kathleen Higginbotham Samson Properties

    255 Sailcloth Way, Chester, MD 21619
    • 1833 Harbor Dr, Chester, MD 21619
      1833 Harbor Dr, Chester, MD 21619
      1833 Harbor Dr, Chester, MD 21619
      /46

      Est $376,717

      Not Listed For Sale

      1833 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,024 Sq Ft
      • Built 1986
      1833 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Janice O'Donnell Chaney Homes, LLC

  • 1870 Harbor Dr, Chester, MD 21619
    1870 Harbor Dr, Chester, MD 21619
    1870 Harbor Dr, Chester, MD 21619
    /34

    $310,000

    Sold Mar 23, 2026

    1870 Harbor Dr, Chester, MD 21619

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • Built 1952

    Last Sold Summary

    • $373/SF
    • 135 Days On Market

    Current Estimated Value $306,854

    Last Listing Agent Rick Parreco RE/MAX Executive

    1870 Harbor Dr, Chester, MD 21619
    • 212 Kirby St, Chester, MD 21619
      212 Kirby St, Chester, MD 21619
      212 Kirby St, Chester, MD 21619
      /28

      Est $541,314

      Not Listed For Sale

      212 Kirby St, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 2,496 Sq Ft
      • Built 1975
      212 Kirby St, Chester, MD 21619

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Eric Smith Vylla Home

  • 255 Redstart Dr, Chester, MD 21619
    255 Redstart Dr, Chester, MD 21619
    255 Redstart Dr, Chester, MD 21619
    /11

    $829,990

    Sold Feb 05, 2026

    255 Redstart Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 2% Below List Price
    • $297/SF
    • 4 Days On Market

    Current Estimated Value $782,894

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

    255 Redstart Dr, Chester, MD 21619
    • 118 Dundee Ave, Chester, MD 21619
      118 Dundee Ave, Chester, MD 21619
      118 Dundee Ave, Chester, MD 21619
      /56

      Est $423,271

      Not Listed For Sale

      118 Dundee Ave, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,174 Sq Ft
      • Built 1937
      118 Dundee Ave, Chester, MD 21619

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Steve Belinky RE/MAX United Real Estate

  • 360 Macum Creek Dr, Chester, MD 21619
    360 Macum Creek Dr, Chester, MD 21619
    360 Macum Creek Dr, Chester, MD 21619
    /71

    $915,000

    Sold Aug 15, 2025

    360 Macum Creek Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 3,225 Sq Ft
    • Built 2012

    Last Sold Summary

    • $284/SF
    • 3 Days On Market

    Current Estimated Value $943,475

    Last Listing Agent Tara Trout Samson Properties

    360 Macum Creek Dr, Chester, MD 21619
    • 2015 Stevens Dr, Chester, MD 21619
      2015 Stevens Dr, Chester, MD 21619
      2015 Stevens Dr, Chester, MD 21619
      /42

      Est $497,784

      Not Listed For Sale

      2015 Stevens Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 2,272 Sq Ft
      • Built 1993
      2015 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent John Logan Real Broker, LLC - Annapolis

  • 630 Warbler Way Unit 2211, Chester, MD 21619
    630 Warbler Way Unit 2211, Chester, MD 21619
    630 Warbler Way Unit 2211, Chester, MD 21619
    /73

    $524,900

    Sold May 14, 2026

    630 Warbler Way Unit 2211, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2025

    Last Sold Summary

    • $262/SF
    • 28 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2211, Chester, MD 21619
    • 1808 Stevens Dr, Chester, MD 21619
      1808 Stevens Dr, Chester, MD 21619
      1808 Stevens Dr, Chester, MD 21619
      /30

      Est $406,847

      Not Listed For Sale

      1808 Stevens Dr, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 1,412 Sq Ft
      • Built 1956
      1808 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Julie Katcef Engel & Völkers Annapolis

  • 527 Warbler Way, Chester, MD 21619
    527 Warbler Way, Chester, MD 21619
    527 Warbler Way, Chester, MD 21619
    /25

    $869,900

    Sold Dec 08, 2025

    527 Warbler Way, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $314/SF
    • 17 Days On Market

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

    527 Warbler Way, Chester, MD 21619
    • 1500 Little Creek Rd, Chester, MD 21619
      1500 Little Creek Rd, Chester, MD 21619
      1500 Little Creek Rd, Chester, MD 21619
      /33

      Est $320,425

      Not Listed For Sale

      1500 Little Creek Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 2,324 Sq Ft
      • Built 1900
      1500 Little Creek Rd, Chester, MD 21619

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Walter Liang Coldwell Banker Realty

  • 1771 Harbor Dr, Chester, MD 21619
    1771 Harbor Dr, Chester, MD 21619
    1771 Harbor Dr, Chester, MD 21619
    /51

    $735,000

    Sold Sep 05, 2025

    1771 Harbor Dr, Chester, MD 21619

    • 5 Beds
    • 2.5 Baths
    • 2,564 Sq Ft
    • Built 1986

    Last Sold Summary

    • $287/SF
    • 195 Days On Market

    Current Estimated Value $758,610

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1771 Harbor Dr, Chester, MD 21619

Showing Results 481 - 520, Page 13 of 18

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