5,231

Chester, MD Homes

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  • /38

    $349,000

    $14K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,302 Sq Ft

    6005 Bridgepointe Dr, Chester, MD 21619

    Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep cleaned, and ready for its new owners! All appliances new within the last two years, power washed & fresh paint on the deck with beautiful views of the pond. Easy access to RT50 - perfect for the commuter. Quiet neighborhood.

    Megan Rosendale Rosendale Realty

    6005 Bridgepointe Dr, 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
    • /27

      Est $340,703

      Not Listed For Sale

      306 Drake Tail Place, Chester, MD 21619

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

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Melissa Murray Compass

  • /81

    $689,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,075 Sq Ft

    2702 Harrington Rd, Chester, MD 21619

    Get ready to be wowed!!! This home has undergone an extensive renovation over the last 5 years. The owners have poured so much love into this home, and it shows. On the interior one of the big standouts is the gourmet kitchen that will surely be the heart of the house. From the granite counters to the 10x4 quartz center island with seating and a built in beverage fridge, to the cozy built in

    Tammy Rosendale Rosendale Realty

    2702 Harrington Rd, 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
    • /66

      Est $384,672

      Not Listed For Sale

      2747 Cecil Dr, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1992
      2747 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Ryan Briggs Anne Arundel Properties, Inc.

  • /19

    $739,900

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

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, 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
    • /19

      Est $278,031

      Not Listed For Sale

      413 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1999
      413 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Cindy Jacobs Maryland Residential Management Co

  • /56

    $629,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 2911, Chester, MD 21619

    Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2911, 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
    • /51

      Est $488,741

      Not Listed For Sale

      412 Hanna Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 1,840 Sq Ft
      • Built 2001
      412 Hanna Ct, Chester, MD 21619

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Sarah Miller Hubble Bisbee Christie's International Real Estate

  • /32

    $319,000

    $30K PRICE DROP
    • 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

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, 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 $518,686

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
    • /47

      Est $385,410

      Not Listed For Sale

      30F Queen Mary Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1999
      30F Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /10

    $216,000

    $24K PRICE DROP
    • 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
  • /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
    • /85

      Est $423,860

      Not Listed For Sale

      28J Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,660 Sq Ft
      • Built 1985
      28J Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /56

    $998,000

    • 3 Beds
    • 2.5 Baths

    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
  • /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 $572,881

    Last Listing Agent Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
    • /40

      Est $471,546

      Not Listed For Sale

      2709 Cox Neck Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,286 Sq Ft
      • Built 1975
      2709 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jessica Garrison LPT Realty, LLC

  • /38

    $319,900

    $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Priced to Sell! 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 elegant quartz countertops—perfect

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline Ct, 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
    • /48

      Est $355,889

      Not Listed For Sale

      5002 Bridgepointe Dr, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1995
      5002 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kathleen Higginbotham 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 bedrooms and full bath.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, 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 $946,318

    Last Listing Agent Meg Richardson Engel & Völkers Annapolis

    130 Sunrise Ct, Chester, MD 21619
    • /44

      Est $295,757

      Not Listed For Sale

      513 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,073 Sq Ft
      • Built 1996
      513 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent April Heim Rosendale 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
  • /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
    • /24

      Est $278,859

      Not Listed For Sale

      314 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1998
      314 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

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

  • /30

    $789,990

    New Construction $28K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 42, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinetry & wall oven.Open concept living spaces with electric fireplace & dry bar.Private owner's suite for rest & relaxation.Refreshing primary bath featuring split vanities & frameless shower door.Functional home office with French double doors for added privacy.Lovely balcony for spending time with friends.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 42, 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 $498,369

    Last Listing Agent Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
    • /27

      Est $343,688

      Not Listed For Sale

      15G Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      15G Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Mackenzie Hoffer CENTURY 21 New Millennium

  • /68

    $924,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 3 Baths
    • 2,745 Sq Ft

    214 Bayberry Dr, Chester, MD 21619

    Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary

    Jim Corson Benson & Mangold, LLC

    214 Bayberry Dr, 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
    • /45

      Est $693,128

      Not Listed For Sale

      106 Woods Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,551 Sq Ft
      • Built 2000
      106 Woods Rd, Chester, MD 21619

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Jackie Ball Daley Northrop Realty

  • /44

    $639,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, 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 $540,635

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    200 Harrier Way Unit 42, Chester, MD 21619
    • /39

      Est $355,431

      Not Listed For Sale

      7003 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1994
      7003 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent April Heim Rosendale Realty

  • /32

    $399,000

    $60K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    REDUCED! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated from top to bottom! Step inside to find the main level that boasts NEW carpet and new LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home office and

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619

Showing Results 201 - 240, Page 6 of 18

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