5,231

Chester, MD Homes

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    • /77

      Not Listed For Sale

      4000 Herons Nest Way Unit 11, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,003 Sq Ft
      • Built 2021
      4000 Herons Nest Way Unit 11, Chester, MD 21619

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Christine Vorsteg Keller Williams Flagship

  • /83

    $525,000

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,552 Sq Ft

    326 Castle Marina Rd, Chester, MD 21619

    Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors

    Ginny Dauses Coldwell Banker Waterman Realty

    326 Castle Marina Rd, Chester, MD 21619
  • /41

    $405,000

    Sold Nov 14, 2025

    1903 Churchhill Ln, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 1,682 Sq Ft
    • Built 1984

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $415,682

    Last Listing Agent Lois Alberti Alberti Realty, LLC

    1903 Churchhill Ln, Chester, MD 21619
    • /98

      Est $755,510

      Not Listed For Sale

      184 Evelyne St, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,437 Sq Ft
      • Built 2013
      184 Evelyne St, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Carrie Rosela Curtis Real Estate Company

  • /32

    $319,000

    $30K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    DON"T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A

    Penny Hope Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • /88

    $689,900

    Sold Nov 12, 2025

    201 Switchgrass Way Unit 1421, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2025

    Last Sold Summary

    • $265/SF
    • 12 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1421, Chester, MD 21619
    • /42

      Est $347,806

      Not Listed For Sale

      300 Drake Tail Place, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1992
      300 Drake Tail Place, Chester, MD 21619

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Donna Wisniewski Long & Foster Real Estate, Inc.

  • /9

    $635,000

    Open Sat 11AM - 1PM Coming Soon Sep 26
    • 5 Beds
    • 2.5 Baths
    • 2,818 Sq Ft

    1616 Postal Rd, Chester, MD 21619

    This charming traditional home, offers a perfect blend of comfort and functionality. With 2,818 square feet of thoughtfully designed living space, this residence features five spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover a cozy family room with wood burning fireplace that seamlessly connects to the kitchen, creating an

    Annie Eaton Coldwell Banker Realty

    1616 Postal Rd, Chester, MD 21619
  • /2

    $445,000

    Sold May 14, 2026

    23F Queen Victoria Way, Chester, MD 21619

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

    Last Sold Summary

    • $403/SF
    • 7 Days On Market

    Current Estimated Value $435,166

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    23F Queen Victoria Way, Chester, MD 21619
    • /34

      Est $729,487

      Not Listed For Sale

      104 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,464 Sq Ft
      • Built 2010
      104 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Paul Mcintye EXIT First Realty

  • /57

    $665,000

    • 2 Beds
    • 2.5 Baths
    • 1,993 Sq Ft

    228 Bayberry Dr, Chester, MD 21619

    OPEN SUNDAY 11:00AM-1:00 Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENSUITE BATHROOMS plus additional HOME OFFICE/DEN or spare bedroom & POWDER ROOM off foyer. The stunning CHEF'S KITCHEN is the heart of this home & opens up to DINING AREA & GREAT ROOM. KITCHEN features upgraded CAFE by GE STAINLESS

    Amy Faust Long & Foster Real Estate, Inc.

    228 Bayberry Dr, Chester, MD 21619
  • /32

    $455,000

    Sold Apr 01, 2026

    1401 Calvert Rd, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • Built 1971

    Last Sold Summary

    • $315/SF
    • 201 Days On Market

    Current Estimated Value $457,645

    Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
    • /55

      Est $685,771

      Not Listed For Sale

      243 Evelyne St, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,386 Sq Ft
      • Built 2011
      243 Evelyne St, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /10

    $216,000

    $24K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    108 Price Rd, Chester, MD 21619

    You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying

    Dana Byrd Thurston Wyatt Real Estate, LLC

    108 Price Rd, Chester, MD 21619
  • /32

    $520,000

    Sold Apr 30, 2026

    190 Harrier Way Unit 11, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2023

    Last Sold Summary

    • 10% Below List Price
    • $260/SF
    • 262 Days On Market

    Current Estimated Value $515,183

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
    • /65

      Est $892,458

      Not Listed For Sale

      151 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,156 Sq Ft
      • Built 2010
      151 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Michele Naish Berkshire Hathaway HomeServices PenFed Realty

  • /56

    $998,000

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

    111 Marshgrass Way Unit 41, Chester, MD 21619

    Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional

    Meg Moran Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 41, Chester, MD 21619
  • /8

    $400,000

    Sold Dec 01, 2025

    326 Hanna Ct, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • Built 2001

    Last Sold Summary

    • $217/SF
    • 98 Days On Market

    Current Estimated Value $429,423

    Last Listing Agent Barry Waterman Coldwell Banker Waterman Realty

    326 Hanna Ct, Chester, MD 21619
    • /60

      Est $554,307

      Not Listed For Sale

      107 Gibson Cir, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 2,048 Sq Ft
      • Built 2009
      107 Gibson Cir, Chester, MD 21619

      Last Sold Summary

      • 35 Days On Market

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

  • /58

    $930,000

    $15K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,761 Sq Ft

    275 Warbler Way, Chester, MD 21619

    Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place.Situated on a premium corner lot, this impressive home

    Justin Kennedy Samson Properties

    275 Warbler Way, Chester, MD 21619
  • /51

    $550,000

    Sold Jan 23, 2026

    224 Bayberry Dr, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft
    • Built 2019

    Last Sold Summary

    • $288/SF
    • 132 Days On Market

    Current Estimated Value $591,675

    Last Listing Agent Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
    • /69

      Est $620,122

      Not Listed For Sale

      201 Gibson Cir, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2010
      201 Gibson Cir, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /29

    $899,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    247 Redstart Dr, Chester, MD 21619

    Efficient kitchen featuring white cabinetry, corner pantry, & vast island.Cozy fireplace adds warmth & character to expansive great room.Serene primary suite with feature wall & stylish ceiling treatment.Refreshing primary bath featuring matte black finishes & walk-in closet.Formal home office provides a quiet space to work remotely.Versatile screened patio for relaxing with

    K. Hovnanian Homes Builder
    247 Redstart Dr, Chester, MD 21619
  • /79

    $499,000

    Sold Apr 10, 2026

    170 Harrier Way Unit 22, Chester, MD 21619

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

    Last Sold Summary

    • $263/SF
    • 320 Days On Market

    Last Listing Agent Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
    • /72

      Est $960,589

      Not Listed For Sale

      432 Macum Creek Dr, Chester, MD 21619

      • 5 Beds
      • 3.5 Baths
      • 3,158 Sq Ft
      • Built 2010
      432 Macum Creek Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Edward Beres RE/MAX Executive

  • /38

    $299,900

    $46K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Motivated Seller! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline Ct, Chester, MD 21619
  • /80

    $935,000

    Sold Nov 17, 2025

    130 Sunrise Ct, Chester, MD 21619

    • 3 Beds
    • 4 Baths
    • 3,494 Sq Ft
    • Built 2022

    Last Sold Summary

    • $268/SF
    • 39 Days On Market

    Current Estimated Value $964,687

    Last Listing Agent Meg Richardson Engel & Völkers Annapolis

    130 Sunrise Ct, Chester, MD 21619
    • /31

      Est $361,609

      Not Listed For Sale

      1817 Stevens Dr, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1976
      1817 Stevens Dr, Chester, MD 21619

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Toni McDowell Keller Williams Select Realtors of Annapolis

  • /46

    $569,900

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

    233 Cross Creek Ct, Chester, MD 21619

    Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass columns (2025) to the

    Christopher Nagel Rory S. Coakley Realty, Inc.

    233 Cross Creek Ct, Chester, MD 21619
  • /50

    $412,000

    Sold Aug 07, 2026

    200 Newtown Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft
    • Built 2017

    Last Sold Summary

    • 7% Below List Price
    • $318/SF
    • 76 Days On Market

    Current Estimated Value $423,436

    Last Listing Agent Kathleen Higginbotham Samson Properties

    200 Newtown Rd, Chester, MD 21619
    • /52

      Est $374,942

      Not Listed For Sale

      6004 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,885 Sq Ft
      • Built 1992
      6004 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /25

    $1,200,000

    New Construction Pending
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    111 Flycatcher Way, Chester, MD 21619

    The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication.Standout features include a dedicated home office, an inviting fireplace, and

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    111 Flycatcher Way, Chester, MD 21619
  • /71

    $499,000

    Sold Jan 15, 2026

    170 Harrier Way Unit 11, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2022

    Last Sold Summary

    • $249/SF
    • 221 Days On Market

    Current Estimated Value $494,472

    Last Listing Agent Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
    • /54

      Est $631,090

      Not Listed For Sale

      143 Carriage Heath, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,241 Sq Ft
      • Built 2009
      143 Carriage Heath, Chester, MD 21619

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Tara Trout Samson Properties

  • /13

    $701,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    Simone Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests.Striking kitchen with large island and plenty of counter space.Open and airy great room with slider to covered patio.Convenient covered patio with screened patio option.Luxurious primary suite with oversized walk-in closet.Relaxing primary bath with split vanities.Versatile loft on second floor with 2 secondary

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • /47

    $465,000

    Sold Jan 07, 2026

    1701 Bayside Dr, Chester, MD 21619

    • 4 Beds
    • 2 Baths
    • 1,980 Sq Ft
    • Built 1954

    Last Sold Summary

    • $235/SF
    • 1 Day On Market

    Current Estimated Value $491,854

    Last Listing Agent Charlotte Savoy The KW Collective

    1701 Bayside Dr, Chester, MD 21619
    • /30

      Est $527,105

      Not Listed For Sale

      1713 Bayside Dr, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 1,980 Sq Ft
      • Built 1972
      1713 Bayside Dr, Chester, MD 21619

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Biana Arentz Coldwell Banker Realty

  • /24

    $1,200,000

    New Construction $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    Formal dining room off the foyer for hosting celebrations. Breathtaking kitchen with stacked grey cabinetry & glass uppers. Sprawling quartz island perfect for prep & dining. Vaulted ceiling with ceiling beams connects dining area and great room. Elegant fireplace and sliding door to screened patio in great room. Private home office for working remotely. Primary suite & bath with dual vanities

    K. Hovnanian Homes Builder
    117 Flycatcher Way, Chester, MD 21619
  • /49

    $557,000

    Sold Nov 10, 2025

    200 Harrier Way Unit 42, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2023

    Last Sold Summary

    • $293/SF
    • 2 Days On Market

    Current Estimated Value $528,076

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    200 Harrier Way Unit 42, Chester, MD 21619
    • /23

      Not Listed For Sale

      1437 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 2009
      1437 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Petra Quinn Realty Navigator

Showing Results 201 - 240, Page 6 of 18

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