5,231

Chester, MD Homes

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    • /43

      Est $547,434

      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

      Last Listing Agent Deborah Shiley Long & Foster Real Estate, Inc.

  • /32

    $949,990

    New Construction $25K PRICE DROP Pending
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    323 Kingfisher Ln, Chester, MD 21619

    Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort and functionality. Projected for November 2026 settlement, this spacious home features 5 bedrooms, 4.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    323 Kingfisher Ln, Chester, MD 21619
  • /22

    $265,000

    Sold Apr 01, 2026

    306 Teal Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $247/SF
    • 6 Days On Market

    Current Estimated Value $267,609

    Last Listing Agent Kelly Schuit Kelly and Co Realty, LLC

    306 Teal Ct, Chester, MD 21619
    • /46

      Est $315,637

      Not Listed For Sale

      31C Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      31C Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /63

    $724,999

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    233 Peregrine Dr, Chester, MD 21619

    Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel

    Michelle Abplanalp Rosendale Realty

    233 Peregrine Dr, Chester, MD 21619
  • /2

    $459,000

    Sold Sep 30, 2025

    113 Chessie Ct, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,858 Sq Ft
    • Built 1999

    Last Sold Summary

    • $247/SF
    • 0 Days On Market

    Current Estimated Value $454,994

    Last Listing Agent Carol Delayo Chaney Homes, LLC

    113 Chessie Ct, Chester, MD 21619
    • /33

      Est $492,818

      Not Listed For Sale

      1852 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,238 Sq Ft
      • Built 1953
      1852 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

  • /91

    $789,000

    • 3 Beds
    • 2.5 Baths
    • 2,787 Sq Ft

    402 Macum Creek Dr, Chester, MD 21619

    Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living

    Tara Trout Samson Properties

    402 Macum Creek Dr, Chester, MD 21619
  • /73

    $524,900

    Sold Feb 17, 2026

    121 Wheelhouse Way Unit 2111, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $262/SF
    • 37 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2111, Chester, MD 21619
    • /12

      Est $376,128

      Not Listed For Sale

      1303 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1955
      1303 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent susan taylor Chaney Homes, LLC

  • /61

    $1,290,000

    $60K PRICE DROP Under Contract
    • 5 Beds
    • 2 Baths
    • 2,700 Sq Ft

    2513 Cecil Dr, Chester, MD 21619

    Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property belongs in a conversation with the finest waterfront offerings on Kent Island, not the most common. Waterfront properties with this combination of acreage, waterfront footage, and finishes are rare at this price

    David Moore Real Broker, LLC

    2513 Cecil Dr, Chester, MD 21619
  • /35

    $501,200

    Sold May 08, 2026

    1363 Calvert Rd, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1992

    Last Sold Summary

    • 7% Above List Price
    • $358/SF
    • 82 Days On Market

    Current Estimated Value $505,415

    Last Listing Agent Benjamin Love Revol Real Estate, LLC

    1363 Calvert Rd, Chester, MD 21619
    • /48

      Est $324,341

      Not Listed For Sale

      1905 Cecil Ct, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,108 Sq Ft
      • Built 1983
      1905 Cecil Ct, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • /2

    $645,000

    Coming Soon Oct 1
    • 6 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1351 Calvert Rd, Chester, MD 21619

    Julie Katcef Engel & Völkers Annapolis

    1351 Calvert Rd, Chester, MD 21619
  • /34

    $700,000

    Sold Dec 04, 2025

    245 Peregrine Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • Built 2024

    Last Sold Summary

    • $222/SF
    • 95 Days On Market

    Last Listing Agent Brandi Bradshaw Keller Williams Select Realtors of Annapolis

    245 Peregrine Dr, Chester, MD 21619
    • /53

      Est $449,588

      Not Listed For Sale

      205 Newtown Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1992
      205 Newtown Rd, Chester, MD 21619

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Teresa Klopfer RE/MAX Realty Group

  • /28

    $350,000

    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft

    200 Church St, Chester, MD 21619

    Your Island Getaway Is Waiting!Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for!Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the

    Darlene Winegardner RE/MAX Executive

    200 Church St, Chester, MD 21619
  • /22

    $714,900

    Sold Nov 03, 2025

    621 Warbler Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $359/SF
    • 9 Days On Market

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

    621 Warbler Way, Chester, MD 21619
    • /65

      Est $315,036

      Not Listed For Sale

      53B Queen Caroline Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1998
      53B Queen Caroline Ct, Chester, MD 21619

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /47

    $819,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2932, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2932, Chester, MD 21619
  • /56

    $837,000

    Sold Sep 30, 2025

    223 Broadwater Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,745 Sq Ft
    • Built 2022

    Last Sold Summary

    • $305/SF
    • 11 Days On Market

    Current Estimated Value $883,627

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
    • /35

      Est $544,244

      Not Listed For Sale

      511 Skipper Ct, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,754 Sq Ft
      • Built 1972
      511 Skipper Ct, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Julie Hall Sellers Choice Real Estate, LLC.

  • /25

    $779,990

    New Construction $70K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    715 Warbler Way, Chester, MD 21619

    Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point.A dedicated home office provides a private space for work or study, while

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    715 Warbler Way, Chester, MD 21619
  • /37

    $382,000

    Sold Mar 20, 2026

    2644 Cecil Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,108 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Above List Price
    • $345/SF
    • 19 Days On Market

    Current Estimated Value $377,894

    Last Listing Agent Julia Stevens Realty Navigator

    2644 Cecil Dr, Chester, MD 21619
    • /53

      Est $375,478

      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

      • 21 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /66

    $899,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    148 Elinor St, Chester, MD 21619

    Welcome to 148 Elinor Street, where timeless coastal style meets a beautifully reimagined interior in the sought-after waterfront community of Gibson’s Grant. This 3-bedroom, 2.5-bath Hartley model by Koch Homes underwent an extensive renovation in 2025, creating a truly turnkey home filled with thoughtful upgrades, designer finishes, and exceptional attention to detail.Step inside to

    Tara Trout Samson Properties

    148 Elinor St, Chester, MD 21619
  • /58

    $768,900

    Sold Nov 24, 2025

    201 Switchgrass Way Unit 1442, Chester, MD 21619

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

    Last Sold Summary

    • $405/SF
    • 53 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1442, Chester, MD 21619
    • /27

      Est $339,064

      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

      • 72 Days On Market

      Last Listing Agent Mark Andrews Keller Williams Select Realtors of Annapolis

  • /29

    $699,000

    $81K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value.Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four

    Matthew Arnold Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • /37

    $999,000

    Sold Jun 15, 2026

    1704 Bayside Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,830 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Below List Price
    • $546/SF
    • 147 Days On Market

    Current Estimated Value $1,036,964

    Last Listing Agent Alex Hodges Cottage Street Realty LLC

    1704 Bayside Dr, Chester, MD 21619
    • /66

      Est $1,699,318

      Not Listed For Sale

      2921 Cox Neck Rd E, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,824 Sq Ft
      • Built 1992
      2921 Cox Neck Rd E, Chester, MD 21619

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lynn Tuozzo Berkshire Hathaway HomeServices PenFed Realty

  • /29

    $899,990

    New Construction $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    532 Warbler Way, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests.Ceiling detail & crown molding carry through the kitchen and great room.Stacked cabinetry with glass-front uppers brings added depth to the kitchen.Fireplace creates a warm focal point in the great room.Screened patio off the great room extends the living space outdoors.Decorative feature walls in the foyer & primary suite

    K. Hovnanian Homes Builder
    532 Warbler Way, 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

    Current Estimated Value $809,570

    Last Listing Agent Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
    • /17

      Est $494,368

      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

      • 354 Days On Market

      Last Listing Agent George Bailey Keller Williams Flagship

  • /36

    $700,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River.The gourmet kitchen is the heart of the home,

    Matthew Arnold Real Broker, LLC

    2000 Herons Nest Way Unit 401, 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 $1,246,047

    Last Listing Agent Cynthia Sullivan Berkshire Hathaway HomeServices Homesale Realty

    1622 Bayside Dr, Chester, MD 21619
    • /38

      Est $419,809

      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

      • 14 Days On Market

      Last Listing Agent Jackie Ball Daley Northrop Realty

  • /39

    $699,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    205 Riverside Dr, Chester, MD 21619

    Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This

    Melissa Chick Engel & Völkers Annapolis

    205 Riverside Dr, Chester, MD 21619
  • /36

    $490,000

    Sold Feb 19, 2026

    906 Auckland Way, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft
    • Built 2001

    Last Sold Summary

    • $236/SF
    • 74 Days On Market

    Current Estimated Value $486,915

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    906 Auckland Way, Chester, MD 21619
    • /42

      Est $394,080

      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

      • 31 Days On Market

      Last Listing Agent Michael Roenigk Chaney Homes, LLC

Showing Results 321 - 360, Page 9 of 18

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