5,168

Chester, MD Homes

Section Image Section Image
  • 35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    /60

    $355,000 Sold Aug 28, 2025

    35 F Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1994

    Last Sold Summary

    • $247/SF
    • 52 Days On Market

    Last Listing Agent Lawrence Doyle Long & Foster Real Estate, Inc.

    35 F Queen Anne Way, Chester, MD 21619
    • 216 Teal Ct, Chester, MD 21619
      216 Teal Ct, Chester, MD 21619
      216 Teal Ct, Chester, MD 21619
      /23

      Est $291,917 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,050 Sq Ft

      216 Teal Ct, Chester, MD 21619

      216 Teal Ct, Chester, MD 21619
  • 104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    /38

    $795,000 Sold Dec 10, 2025

    104 Woods Rd, Chester, MD 21619

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft
    • Built 2002

    Last Sold Summary

    • $259/SF
    • 95 Days On Market

    Last Listing Agent Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
    • 105 Barren Ridge Rd, Chester, MD 21619
      105 Barren Ridge Rd, Chester, MD 21619
      105 Barren Ridge Rd, Chester, MD 21619
      /46

      Est $647,076 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,016 Sq Ft

      105 Barren Ridge Rd, Chester, MD 21619

      105 Barren Ridge 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

    $485,000 Sold Mar 14, 2025

    51D Queen Caroline Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1995

    Last Sold Summary

    • $337/SF
    • 0 Days On Market

    Current Estimated Value $464,091

    Last Listing Agent Kathleen Higginbotham Samson Properties

    51D Queen Caroline Ct, Chester, MD 21619
    • 1006 Auckland Way, Chester, MD 21619
      1006 Auckland Way, Chester, MD 21619
      1006 Auckland Way, Chester, MD 21619
      /60

      Est $552,363 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,076 Sq Ft

      1006 Auckland Way, Chester, MD 21619

      1006 Auckland Way, Chester, MD 21619
  • 1622 Bayside Dr, Chester, MD 21619
    1622 Bayside Dr, Chester, MD 21619
    1622 Bayside Dr, Chester, MD 21619
    /68

    $1,200,000 Sold Sep 30, 2025

    1622 Bayside Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 2009

    Last Sold Summary

    • $400/SF
    • 112 Days On Market

    Current Estimated Value $1,198,468

    Last Listing Agent Cynthia Sullivan Sullivan Select, LLC.

    1622 Bayside Dr, Chester, MD 21619
    • 1905 Roberta Dr, Chester, MD 21619
      1905 Roberta Dr, Chester, MD 21619
      1905 Roberta Dr, Chester, MD 21619
      /39

      Est $521,397 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,100 Sq Ft

      1905 Roberta Dr, Chester, MD 21619

      1905 Roberta Dr, Chester, MD 21619
  • 1752 Harbor Dr, Chester, MD 21619
    1752 Harbor Dr, Chester, MD 21619
    1752 Harbor Dr, Chester, MD 21619
    /62

    $495,000 Sold Mar 06, 2025

    1752 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft
    • Built 1954

    Last Sold Summary

    • $236/SF
    • 19 Days On Market

    Current Estimated Value $480,343

    Last Listing Agent Martin Farmer Cummings & Co. Realtors

    1752 Harbor Dr, Chester, MD 21619
    • 106 Logan Ct, Chester, MD 21619
      106 Logan Ct, Chester, MD 21619
      106 Logan Ct, Chester, MD 21619
      /3

      Est $525,231 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,242 Sq Ft

      106 Logan Ct, Chester, MD 21619

      106 Logan Ct, Chester, MD 21619
  • 15G Queen Anne Way, Chester, MD 21619
    15G Queen Anne Way, Chester, MD 21619
    15G Queen Anne Way, Chester, MD 21619
    /27

    $340,000 Sold Jul 31, 2025

    15G Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft
    • Built 1983

    Last Sold Summary

    • $308/SF
    • 34 Days On Market

    Current Estimated Value $351,387

    Last Listing Agent Mackenzie Hoffer CENTURY 21 New Millennium

    15G Queen Anne Way, Chester, MD 21619
    • 604 Dominion Rd, Chester, MD 21619
      604 Dominion Rd, Chester, MD 21619
      604 Dominion Rd, Chester, MD 21619
      /46

      Est $359,246 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft

      604 Dominion Rd, Chester, MD 21619

      604 Dominion Rd, Chester, MD 21619
  • 124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    /45

    $825,000 Sold Dec 09, 2025

    124 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft
    • Built 2021

    Last Sold Summary

    • $319/SF
    • 87 Days On Market

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
    • 910 Auckland Way, Chester, MD 21619
      910 Auckland Way, Chester, MD 21619
      910 Auckland Way, Chester, MD 21619
      /67

      Est $549,057 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,100 Sq Ft

      910 Auckland Way, Chester, MD 21619

      910 Auckland Way, Chester, MD 21619
  • 148 Nighthawk Dr, Stevensville, MD 21666
    148 Nighthawk Dr, Stevensville, MD 21666
    148 Nighthawk Dr, Stevensville, MD 21666
    /51

    $884,900 Sold May 23, 2025

    148 Nighthawk Dr, Stevensville, MD 21666

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2024

    Last Sold Summary

    • $319/SF
    • 5 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    148 Nighthawk Dr, Stevensville, MD 21666
    • 204 Schooner Way, Chester, MD 21619
      204 Schooner Way, Chester, MD 21619
      204 Schooner Way, Chester, MD 21619
      /45

      Est $493,015 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft

      204 Schooner Way, Chester, MD 21619

      204 Schooner Way, Chester, MD 21619
  • 103 John Gibson Dr, Chester, MD 21619
    103 John Gibson Dr, Chester, MD 21619
    103 John Gibson Dr, Chester, MD 21619
    /62

    $789,000 Sold Aug 27, 2025

    103 John Gibson Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,602 Sq Ft
    • Built 2012

    Last Sold Summary

    • $303/SF
    • 120 Days On Market

    Current Estimated Value $799,568

    Last Listing Agent Edward Beres RE/MAX Executive

    103 John Gibson Dr, Chester, MD 21619
    • 2608 Harrington Rd, Chester, MD 21619
      2608 Harrington Rd, Chester, MD 21619
      2608 Harrington Rd, Chester, MD 21619
      /23

      Est $416,738 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      2608 Harrington Rd, Chester, MD 21619

      2608 Harrington Rd, Chester, MD 21619
  • 413 Dominion Rd, Chester, MD 21619
    413 Dominion Rd, Chester, MD 21619
    413 Dominion Rd, Chester, MD 21619
    /30

    $370,000 Sold Oct 07, 2025

    413 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft
    • Built 1896

    Last Sold Summary

    • $275/SF
    • 103 Days On Market

    Current Estimated Value $361,180

    Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

    413 Dominion Rd, Chester, MD 21619
    • 230 Cross Creek Ct, Chester, MD 21619
      230 Cross Creek Ct, Chester, MD 21619
      230 Cross Creek Ct, Chester, MD 21619
      /30

      Est $562,539 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,332 Sq Ft

      230 Cross Creek Ct, Chester, MD 21619

      230 Cross Creek Ct, Chester, MD 21619
  • 519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    /20

    $849,990 Sold Jan 07, 2026

    519 Warbler Way, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $307/SF
    • 35 Days On Market

    K. Hovnanian Homes K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series

    519 Warbler Way, Chester, MD 21619
    • 2709 Sherman Dr, Chester, MD 21619
      2709 Sherman Dr, Chester, MD 21619
      2709 Sherman Dr, Chester, MD 21619
      /30

      Est $433,934 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,512 Sq Ft

      2709 Sherman Dr, Chester, MD 21619

      2709 Sherman Dr, Chester, MD 21619
  • 320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    /63

    $775,000 Sold Jul 28, 2025

    320 Bayberry Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • Built 2021

    Last Sold Summary

    • $332/SF
    • 1 Day On Market

    Current Estimated Value $768,596

    Last Listing Agent Melanie Wood Berkshire Hathaway HomeServices PenFed Realty

    320 Bayberry Dr, Chester, MD 21619
    • 304 Widgeon Way, Chester, MD 21619
      304 Widgeon Way, Chester, MD 21619
      304 Widgeon Way, Chester, MD 21619
      /48

      Est $447,138 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 1,899 Sq Ft

      304 Widgeon Way, Chester, MD 21619

      304 Widgeon Way, Chester, MD 21619
  • 306 Skipper Ln, Chester, MD 21619
    306 Skipper Ln, Chester, MD 21619
    306 Skipper Ln, Chester, MD 21619
    /33

    $569,000 Sold Dec 03, 2025

    306 Skipper Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,610 Sq Ft
    • Built 1974

    Last Sold Summary

    • $218/SF
    • 9 Days On Market

    Last Listing Agent Elizabeth Arentz Coldwell Banker Realty

    306 Skipper Ln, Chester, MD 21619
    • 104 Sunset Dr, Chester, MD 21619
      104 Sunset Dr, Chester, MD 21619
      104 Sunset Dr, Chester, MD 21619
      /73

      Est $625,863 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,096 Sq Ft

      104 Sunset Dr, Chester, MD 21619

      104 Sunset Dr, Chester, MD 21619
  • 15J Piney Narrows Rd, Chester, MD 21619
    15J Piney Narrows Rd, Chester, MD 21619
    15J Piney Narrows Rd, Chester, MD 21619
    /13

    $21,000 Sold Apr 18, 2025

    15J Piney Narrows Rd, Chester, MD 21619

    • 600 Sq Ft
    • Built 1980

    Last Sold Summary

    • $35/SF
    • 9 Days On Market

    Current Estimated Value $20,431

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    15J Piney Narrows Rd, Chester, MD 21619
    • 1617 Chester Rd, Chester, MD 21619
      1617 Chester Rd, Chester, MD 21619
      1617 Chester Rd, Chester, MD 21619
      /39

      Est $504,216 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,976 Sq Ft

      1617 Chester Rd, Chester, MD 21619

      1617 Chester Rd, Chester, MD 21619
  • 214 Claiborne St, Chester, MD 21619
    214 Claiborne St, Chester, MD 21619
    214 Claiborne St, Chester, MD 21619
    /94

    $570,000 Sold May 20, 2025

    214 Claiborne St, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,852 Sq Ft
    • Built 2014

    Last Sold Summary

    • $308/SF
    • 153 Days On Market

    Current Estimated Value $592,195

    Last Listing Agent Barbara McCaffrey Redfin Corp

    214 Claiborne St, Chester, MD 21619
    • 507 Teal Ct, Chester, MD 21619
      507 Teal Ct, Chester, MD 21619
      507 Teal Ct, Chester, MD 21619
      /20

      Est $290,472 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,071 Sq Ft

      507 Teal Ct, Chester, MD 21619

      507 Teal Ct, Chester, MD 21619
  • 157 John Gibson Dr, Chester, MD 21619
    157 John Gibson Dr, Chester, MD 21619
    157 John Gibson Dr, Chester, MD 21619
    /79

    $680,000 Sold Nov 03, 2025

    157 John Gibson Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft
    • Built 2010

    Last Sold Summary

    • $302/SF
    • 26 Days On Market

    Current Estimated Value $681,607

    Last Listing Agent Ryan Briggs Anne Arundel Properties, Inc.

    157 John Gibson Dr, Chester, MD 21619
    • 106 Blenny Ln, Chester, MD 21619
      106 Blenny Ln, Chester, MD 21619
      106 Blenny Ln, Chester, MD 21619
      /50

      Est $373,252 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 1,899 Sq Ft

      106 Blenny Ln, Chester, MD 21619

      106 Blenny Ln, Chester, MD 21619
  • 201 Switchgrass Way Unit 42, Chester, MD 21619
    201 Switchgrass Way Unit 42, Chester, MD 21619
    201 Switchgrass Way Unit 42, Chester, MD 21619
    /25

    $784,900 Sold Aug 20, 2025

    201 Switchgrass Way Unit 42, 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 K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos

    201 Switchgrass Way Unit 42, Chester, MD 21619
    • 6008 Bridgepointe Dr, Chester, MD 21619
      6008 Bridgepointe Dr, Chester, MD 21619
      6008 Bridgepointe Dr, Chester, MD 21619
      /41

      Est $352,233 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,302 Sq Ft

      6008 Bridgepointe Dr, Chester, MD 21619

      6008 Bridgepointe Dr, Chester, MD 21619
  • 246 Peregrine Dr, Stevensville, MD 21666
    246 Peregrine Dr, Stevensville, MD 21666
    246 Peregrine Dr, Stevensville, MD 21666
    /40

    $749,900 Sold May 16, 2025

    246 Peregrine Dr, Stevensville, MD 21666

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • Built 2025

    Last Sold Summary

    • $269/SF
    • 44 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    246 Peregrine Dr, Stevensville, MD 21666
    • 102 Skipper Ln, Chester, MD 21619
      102 Skipper Ln, Chester, MD 21619
      102 Skipper Ln, Chester, MD 21619
      /24

      Est $536,033 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,810 Sq Ft

      102 Skipper Ln, Chester, MD 21619

      102 Skipper Ln, Chester, MD 21619
  • 3C Piney Narrows Rd, Chester, MD 21619
    3C Piney Narrows Rd, Chester, MD 21619
    3C Piney Narrows Rd, Chester, MD 21619
    /14

    $28,000 Sold Mar 13, 2025

    3C Piney Narrows Rd, Chester, MD 21619

    • 540 Sq Ft
    • Built 1492

    Last Sold Summary

    • $52/SF
    • 1 Day On Market

    Current Estimated Value $27,553

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    3C Piney Narrows Rd, Chester, MD 21619
    • 206 Widgeon Way, Chester, MD 21619
      206 Widgeon Way, Chester, MD 21619
      206 Widgeon Way, Chester, MD 21619
      /40

      Est $516,305 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft

      206 Widgeon Way, Chester, MD 21619

      206 Widgeon Way, Chester, MD 21619
  • 211 Switchgrass Way Unit 42, Chester, MD 21619
    211 Switchgrass Way Unit 42, Chester, MD 21619
    211 Switchgrass Way Unit 42, Chester, MD 21619
    /26

    $679,900 Sold Jul 23, 2025

    211 Switchgrass Way Unit 42, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $358/SF
    • 4 Days On Market

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

    211 Switchgrass Way Unit 42, Chester, MD 21619
    • 601 Teal Ct, Chester, MD 21619
      601 Teal Ct, Chester, MD 21619
      601 Teal Ct, Chester, MD 21619
      /35

      Est $280,237 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft

      601 Teal Ct, Chester, MD 21619

      601 Teal Ct, Chester, MD 21619

Showing Results 321 - 360, Page 9 of 18

Maryland Queen Annes County Chester

Real Estate & Homes

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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