5,197

Chester, MD Homes

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    • /53

      Est $360,769 Not Listed For Sale

      102 Ringneck Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,747 Sq Ft
      • Built 1995
      102 Ringneck Ct, Chester, MD 21619

      Last Sold Summary

      • 2% Below List Price
      • $212/SF
      • 21 Days On Market

      Last Sold Price $369,999

      Last Listing Agent Crystal Smith RE/MAX

  • /28

    $375,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 2,200 Sq Ft

    1150 Little Creek Rd, Chester, MD 21619

    Start living the watermen dream! This charming home offers a thoughtfully designed layout with an open, airy flow and spacious rooms throughout. Situated on nearly one acre, you’ll enjoy both comfort and room to roam. The oversized living area is filled with natural sunlight streaming through the windows, creating a warm and inviting atmosphere. The first floor recently fresh coat of paint. Step

    Dee Dee McCracken Coldwell Banker Realty

    1150 Little Creek Rd, Chester, MD 21619
  • /47

    $394,000 Sold Jun 05, 2025

    3 Queen Victoria Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 1985

    Last Sold Summary

    • $313/SF
    • 32 Days On Market

    Last Listing Agent Carol Tinnin RE/MAX Leading Edge

    3 Queen Victoria Way, Chester, MD 21619
    • /27

      Est $332,162 Not Listed For Sale

      1304 Little Creek Rd, Chester, MD 21619

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1979
      1304 Little Creek Rd, Chester, MD 21619

      Last Sold Summary

      • 6% Below List Price
      • $387/SF
      • 72 Days On Market

      Last Sold Price $353,000

      Last Listing Agent Mark Andrews Keller Williams Select Realtors of Annapolis

  • /21

    $849,990 New Construction

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

    110 Boatswain Way Unit 31, Chester, MD 21619

    Home office with double doors for privacy. Great room with an electric fireplace for warmth & charm. Large central island anchors the gourmet kitchen. Dry bar in dining area creates a perfect hosting space. Owner’s suite with a serene sitting room & balcony access. Dual walk-in closets for organized living. Owner’s bath with sleek dual sinks & spacious layout.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 31, 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 $431,046

    Last Listing Agent Barry Waterman Coldwell Banker Waterman Realty

    326 Hanna Ct, Chester, MD 21619
    • /17

      Est $472,335 Not Listed For Sale

      2616 Cecil Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • Built 1984
      2616 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 26% Below List Price
      • 354 Days On Market

      Last Sold Price $634,595

      Last Listing Agent George Bailey Keller Williams Flagship

  • /5

    $5,000

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

    507 Teal Ct, Chester, MD 21619

    Foreclosure Auction Ends April 14, 2026 at 10:05 AM EST. Discover this inviting 2-bedroom, 2-bathroom single-family home, offering a great opportunity in a welcoming Chester community. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa Home App.

    Jamie Boone Jamie L Boone LLC

    507 Teal Ct, 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 $561,128

    Last Listing Agent Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
    • /38

      Est $412,045 Not Listed For Sale

      1806 Chester Dr, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 1962
      1806 Chester Dr, Chester, MD 21619

      Last Sold Summary

      • 2% Below List Price
      • $289/SF
      • 14 Days On Market

      Last Sold Price $420,000

      Last Listing Agent Jackie Ball Daley Creig Northrop Team of Long & Foster

  • /29

    $324,900 Under Contract

    • 1,747 Sq Ft

    204 Ringneck Ct, Chester, MD 21619

    Price improvement just in time for the spring market!Come see all of amazing amenities this water privileged community has! Enjoy the boating, pool, restaurants and Cross Island trail all within walking distance of this great home! Lovely 3 level townhome in the water oriented community of Bayside Marina offering 2/3 bedrooms and 3 full and one half baths. This multifunctional unit can be two

    Mary Wagner Cummings & Co. Realtors

    204 Ringneck 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 $947,390

    Last Listing Agent Meg Richardson Engel & Völkers Annapolis

    130 Sunrise Ct, Chester, MD 21619
    • /42

      Est $373,774 Not Listed For Sale

      218 Blenny Ln, Chester, MD 21619

      • 4 Beds
      • 4 Baths
      • 1,900 Sq Ft
      • Built 1999
      218 Blenny Ln, Chester, MD 21619

      Last Sold Summary

      • 4% Below List Price
      • $205/SF
      • 31 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Michael Roenigk Chaney Homes, LLC

  • /2

    $599,000 Coming Soon

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

    1000 Herons Nest Way Unit 42, Chester, MD 21619

    Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and the Community Kayak's. Located within the serene and vibrant community of Four Seasons at Kent Island, this exquisite 2-bedroom, 2.5 bath Built in 2020, this elegant unit combines modern design with high-end finishes, creating a

    Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 42, Chester, MD 21619
  • /61

    $559,000 Sold Jun 18, 2025

    32F Queen Anne Way, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 1983

    Last Sold Summary

    • $333/SF
    • 10 Days On Market

    Current Estimated Value $541,755

    Last Listing Agent The Williams Home Team Douglas Realty, LLC

    32F Queen Anne Way, Chester, MD 21619
    • /32

      Est $506,053 Not Listed For Sale

      1402 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft
      • Built 1972
      1402 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 8% Above List Price
      • $255/SF
      • 6 Days On Market

      Last Sold Price $470,000

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /40

    $349,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    Nothing to do but move in! 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 propane fireplace highlights the great room turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, 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 $497,762

    Last Listing Agent Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
    • /34

      Est $367,322 Not Listed For Sale

      108 Blenny Ln, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,899 Sq Ft
      • Built 2000
      108 Blenny Ln, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $187/SF
      • 32 Days On Market

      Last Sold Price $356,000

      Last Listing Agent Matthew Wyble Next Step Realty

  • /48

    $479,000

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

    312 Blenny Ln, Chester, MD 21619

    You don't want to miss the opportunity to enjoy Island Living in this maintenance free Pond View End Unit! Come enjoy Island Living in the Bayside Community. Offering Pond Views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout on your

    Judith Brown EXP Realty, LLC

    312 Blenny Ln, 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 $464,964

    Last Listing Agent Charlotte Savoy The KW Collective

    1701 Bayside Dr, Chester, MD 21619
    • /44

      Est $587,541 Not Listed For Sale

      1624 Calvert Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,470 Sq Ft
      • Built 1976
      1624 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 16% Above List Price
      • $204/SF
      • 22 Days On Market

      Last Sold Price $505,000

      Last Listing Agent Lois Alberti Alberti Realty, LLC

  • /44

    $889,990 New Construction

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

    102 Warbler Way Unit 2921, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, 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 $555,520

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    200 Harrier Way Unit 42, Chester, MD 21619
    • /72

      Est $1,097,028 Not Listed For Sale

      1507 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,558 Sq Ft
      • Built 1966
      1507 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 6% Above List Price
      • $406/SF
      • 6 Days On Market

      Last Sold Price $1,039,000

      Last Listing Agent Beverly Sloane Benson & Mangold, LLC

  • /13

    $701,990 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, 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
  • /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
    • /56

      Est $367,875 Not Listed For Sale

      30G Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1999
      30G Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 1% Above List Price
      • $285/SF
      • 20 Days On Market

      Last Sold Price $365,000

      Last Listing Agent Cynthia Sullivan Sullivan Select, LLC.

  • /49

    $1,100,000 New Construction

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

    127 Flycatcher Way, Chester, MD 21619

    The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    127 Flycatcher 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 K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series

    629 Warbler Way, Chester, MD 21619
    • /3

      Est $276,889 Not Listed For Sale

      202 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,073 Sq Ft
      • Built 1998
      202 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 5% Below List Price
      • $270/SF
      • 36 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Regina Fischer Long & Foster

  • /24

    $1,400,000 New Construction

    • 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
  • /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 $518,429

    Last Listing Agent Justin Kennedy Samson Properties

    312 Hanna Ct, Chester, MD 21619
    • /20

      Est $444,667 Not Listed For Sale

      1703 Chester Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,556 Sq Ft
      • Built 1991
      1703 Chester Rd, Chester, MD 21619

      Last Sold Summary

      • 6% Above List Price
      • $270/SF
      • 5 Days On Market

      Last Sold Price $420,000

      Last Listing Agent Lona Todd Taylor Properties

  • /45

    $995,000

    • 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
  • /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 $355,176

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    206 Ringneck Ct Unit 78, Chester, MD 21619
    • /73

      Est $381,760 Not Listed For Sale

      312 Widgeon Way, Chester, MD 21619

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

      Last Sold Summary

      • 2% Above List Price
      • $197/SF
      • 30 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Lauren Matera BHHS PenFed (actual)

  • /89

    $779,900

    • 3 Beds
    • 2 Baths
    • 2,394 Sq Ft

    169 Harrier Way, Chester, MD 21619

    Look no further—welcome to the prestigious 55+ resort-style community of Four Seasons at Kent Island, where refined living meets effortless elegance. This exquisitely upgraded Killarney model offers over 2,300 square feet of thoughtfully designed single-level living, featuring an open-concept layout and high-end finishes throughout.At the heart of the home is a stunning gourmet kitchen,

    Dorothea Slaughter Century 21 Redwood Realty

    169 Harrier Way, Chester, MD 21619
  • /67

    $319,000 Sold Jun 13, 2025

    53C Queen Caroline Ct Unit C, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1998

    Last Sold Summary

    • $222/SF
    • 52 Days On Market

    Last Listing Agent Julia Stevens Realty Navigator

    53C Queen Caroline Ct Unit C, Chester, MD 21619
    • /56

      Est $458,653 Not Listed For Sale

      6B Queen Victoria Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1983
      6B Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 5% Above List Price
      • $261/SF
      • 31 Days On Market

      Last Sold Price $438,000

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

Showing Results 201 - 240, Page 6 of 18

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