5,227

Chester, MD Homes

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  • /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
  • /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 $437,164

    Last Listing Agent Barry Waterman Coldwell Banker Waterman Realty

    326 Hanna Ct, Chester, MD 21619
    • /46

      Est $493,144

      Not Listed For Sale

      915 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,100 Sq Ft
      • Built 2001
      915 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 67 Days On Market

  • /40

    $749,950

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths

    212 Switchgrass Way Unit 34, Chester, MD 21619

    Best View of the Chester River. Check it out!Experience elevated Eastern Shore living in this beautifully appointed corner residence overlooking the Chester River in the sought-after 55+ waterfront community of K. Hovnanian’s Four Seasons at Kent Island. Just one year old and impeccably maintained, this spacious three-bedroom, two-and-a-half-bath home offers more than 2,600 square feet of

    Jennifer Thomas RE/MAX Executive

    212 Switchgrass Way Unit 34, 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 $586,602

    Last Listing Agent Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
    • /27

      Est $355,658

      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

  • /45

    $945,000

    $50K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

    Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, 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
    • /19

      Est $287,538

      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

  • /44

    $639,900

    • 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
  • /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 $952,051

    Last Listing Agent Meg Richardson Engel & Völkers Annapolis

    130 Sunrise Ct, Chester, MD 21619
    • /47

      Est $369,289

      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

  • /32

    $434,900

    $24K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    PRICE REDUCTION! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully refreshed 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

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, 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 $529,189

    Last Listing Agent Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
    • /85

      Est $383,815

      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

  • /81

    $650,000

    Open Wed 5PM - 7PM
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    190 Harrier Way Unit 24, Chester, MD 21619

    Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 square feet of comfort, space, and resort-style amenities. The open living, dining, and kitchen layout is ideal for everyday living and entertaining.Enjoy peaceful views of three ponds from the beautiful porch, with limited views of the Chester River. The kitchen features 42-inch cabinets, white quartz

    Dee Dee McCracken Coldwell Banker Realty

    190 Harrier Way Unit 24, 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 $468,064

    Last Listing Agent Charlotte Savoy The KW Collective

    1701 Bayside Dr, Chester, MD 21619
    • /40

      Est $454,574

      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

  • /73

    $707,000

    $43K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner and priced well below the new construction models that are now selling for over $800,000. With recent improvements including paint and Plantation Shutters, this home is move

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • /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 $581,166

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    200 Harrier Way Unit 42, Chester, MD 21619
    • /48

      Est $367,262

      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

  • /63

    $599,990

    New Construction $100K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    176 Flagstaff Way Unit 2411, Chester, MD 21619

    The Magothy at Lot 2411 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2411, Chester, MD 21619
  • /61

    $704,900

    Sold Feb 19, 2026

    121 Wheelhouse Way Unit 2124, Chester, MD 21619

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

    Last Sold Summary

    • 2% Below List Price
    • $271/SF
    • 0 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2124, Chester, MD 21619
    • /24

      Est $290,109

      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

  • /15

    $769,990

    New Construction $102K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    711 Warbler Way, Chester, MD 21619

    Beautiful kitchen with white cabinetry & glass-front uppers.Vast island & countertops for preparing meals.Elegant dining area for hosting special dinners.Incredible great room featuring stunning fireplace.Serene primary suite with gorgeous ceiling moulding.Lavish primary bath featuring freestanding white vanities.Screened patio off the great room extends living space

    K. Hovnanian Homes Builder
    711 Warbler Way, Chester, MD 21619
  • /11

    $709,900

    Sold Sep 18, 2025

    629 Warbler Way, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $254/SF
    • 42 Days On Market

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

    629 Warbler Way, Chester, MD 21619
    • /39

      Est $369,792

      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

  • /60

    $1,350,000

    • 5 Beds
    • 2 Baths
    • 2,700 Sq Ft

    2513 Cecil Dr, Chester, MD 21619

    The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and

    David Moore Real Broker, LLC

    2513 Cecil Dr, Chester, MD 21619
  • /45

    $492,500

    Sold Oct 06, 2025

    312 Hanna Ct, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 1,988 Sq Ft
    • Built 2001

    Last Sold Summary

    • $248/SF
    • 4 Days On Market

    Current Estimated Value $527,711

    Last Listing Agent Justin Kennedy Samson Properties

    312 Hanna Ct, Chester, MD 21619
    • /22

      Est $392,200

      Not Listed For Sale

      500 Dominion Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2000
      500 Dominion Rd, Chester, MD 21619

      Last Sold Summary

      • 53 Days On Market

  • /27

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • /23

    $335,000

    Sold Jan 02, 2026

    206 Ringneck Ct Unit 78, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • Built 1995

    Last Sold Summary

    • $192/SF
    • 3 Days On Market

    Current Estimated Value $394,363

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    206 Ringneck Ct Unit 78, Chester, MD 21619
    • /43

      Est $495,671

      Not Listed For Sale

      1303 Saint Marys Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,970 Sq Ft
      • Built 1964
      1303 Saint Marys Rd, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /50

    $600,000

    Open Wed 5PM - 7PM
    • 2 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1000 Herons Nest Way Unit 43, Chester, MD 21619

    Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment.Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center

    Dee Dee McCracken Coldwell Banker Realty

    1000 Herons Nest Way Unit 43, Chester, MD 21619
  • /2

    $360,000

    Sold Mar 27, 2026

    9B Queen Victoria Way, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $214/SF
    • 24 Days On Market

    Current Estimated Value $360,632

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    9B Queen Victoria Way, Chester, MD 21619
    • /29

      Est $528,533

      Not Listed For Sale

      1903 Roberta Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,560 Sq Ft
      • Built 1969
      1903 Roberta Dr, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

  • /41

    $449,900

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    *PRICE IMPROVEMENT!* Welcome to this beautifully renovated ranch-style home offering 4 bedrooms, 2 full bathrooms, and a spacious open floor plan designed for modern living. Completely remodeled from top to bottom, this move-in ready property combines style, comfort, and functionality in every detail. The stunning kitchen features sleek quartz countertops, stainless steel appliances, and a large

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • /88

    $734,900

    Sold Sep 10, 2025

    211 Switchgrass Way Unit 1531, Chester, MD 21619

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

    Last Sold Summary

    • $282/SF
    • 27 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1531, Chester, MD 21619
    • /43

      Est $433,762

      Not Listed For Sale

      510 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,899 Sq Ft
      • Built 2001
      510 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

  • /44

    $849,990

    New Construction $90K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619

Showing Results 201 - 240, Page 6 of 18

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