5,224

Homes in ZIP Code 21619

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  • /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
  • /10

    $659,990

    Sold Mar 11, 2026

    176 Flagstaff Way Unit 12, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 6% Below List Price
    • $330/SF
    • 5 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    176 Flagstaff Way Unit 12, 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

  • /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
  • /2

    $629,990

    Sold Sep 09, 2026

    110 Boatswain Way Unit 12, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $315/SF
    • 8 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 12, 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

  • /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
  • /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
    • /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

  • /66

    $899,000

    • 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
  • /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
    • /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

  • /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
  • /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
    • /44

      Est $568,447

      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

      • 22 Days On Market

      Last Listing Agent Lois Alberti Alberti Realty, LLC

  • /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
  • /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
    • /3

      Est $282,607

      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

      • 36 Days On Market

      Last Listing Agent Regina Fischer Long & Foster Real Estate, Inc.

  • /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
  • /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
    • /20

      Est $444,065

      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

      • 5 Days On Market

      Last Listing Agent Lona Todd Taylor Properties

  • /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
  • /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
    • /11

      Est $279,179

      Not Listed For Sale

      107 Lee Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1984
      107 Lee Rd, Chester, MD 21619

      Last Sold Summary

      • 160 Days On Market

      Last Listing Agent Darlene Winegardner RE/MAX Executive

  • /27

    $689,990

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

    830 Warbler Way Unit 33, Chester, MD 21619

    Private home office with elegant French double doors.Gourmet kitchen features a center island & built-in wall oven.Dining area includes a dry bar for added convenience.Great room with an electric fireplace opens to the balcony.Owner's suite offers balcony access for a relaxing retreat.Spa bath provides comfort with dual vanities & modern design.Laundry room includes

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 33, 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 $858,501

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
    • /73

      Est $399,135

      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

      • 30 Days On Market

      Last Listing Agent Lauren Matera LPT Realty, LLC

  • /21

    $594,990

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

    Severn Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, 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
    • /35

      Est $314,800

      Not Listed For Sale

      28G Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,010 Sq Ft
      • Built 1985
      28G Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Bev Langley Coldwell Banker Realty

  • /79

    $862,750

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,331 Sq Ft

    320 Bayberry Dr, Chester, MD 21619

    THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fastest growing 55+ community on Maryland's Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands

    Jeremy McDonough Mr. Lister Realty

    320 Bayberry Dr, 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
    • /43

      Est $394,808

      Not Listed For Sale

      1808 Chester Dr, Chester, MD 21619

      • 3 Beds
      • 1.5 Baths
      • 1,700 Sq Ft
      • Built 1978
      1808 Chester Dr, Chester, MD 21619

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /5

    $149,900

    • Land
    • 12,632 Sq Ft
    • $516,897 per Acre

    0 Harley Ln, Chester, MD 21619

    Lot 1 of two newly formed building lots on Kent Island in Chester just off Dominion Road. Sewer Allocation has been paid (a $11,800 value!) and this lot has a working well! The site work has been done. Right around the corner from the Goodhands Creek Landing to launch your boat. Close to Rt 50/301 & Main Street for convenient commuting and shopping!

    Jason Dey Kevin Dey Realty

    0 Harley Ln, 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
    • /137

      Est $813,673

      Not Listed For Sale

      117 Kirwans Landing Ln, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,288 Sq Ft
      • Built 1986
      117 Kirwans Landing Ln, Chester, MD 21619

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • /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
  • /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
    • /63

      Est $517,953

      Not Listed For Sale

      23D Queen Victoria Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1985
      23D Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /123

    $747,900

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft

    209 Harrier Way, Stevensville, MD 21666

    Welcome Home!!! Open DAILY by Appointment - Or stop by one of our OPEN HOUSES***If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds.*** Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs

    Violeta Aguirre Long & Foster Real Estate, Inc.

    209 Harrier Way, Stevensville, MD 21666

Showing Results 321 - 360, Page 9 of 18

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