5,228

Chester, MD Homes

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  • /32

    $374,900

    $8K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    2004 Bridgepointe Dr, Chester, MD 21619

    OPEN HOUSE this Saturday 7/25 - 9am to 11am! ALL NEW Carpet & flooring, fresh custom paint, granite countertops and newer appliances! Welcome to one of the most desirable homes in the Bridgepointe community! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of

    Sheryl Carmody RE/MAX Executive

    2004 Bridgepointe Dr, Chester, MD 21619
  • /54

    $570,000

    Sold Jun 19, 2026

    1000 Herons Nest Way Unit 402, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $300/SF
    • 42 Days On Market

    Last Listing Agent Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 402, Chester, MD 21619
    • /39

      Est $497,919

      Not Listed For Sale

      405 Widgeon Way, Chester, MD 21619

      • 2 Beds
      • 3.5 Baths
      • 2,112 Sq Ft
      • Built 2000
      405 Widgeon Way, Chester, MD 21619

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Carol Tinnin RE/MAX Leading Edge

  • /33

    $829,990

    New Construction $35K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island. Spacious great room featuring electric fireplace. Charming dining area with dry bar for efficient serving. Serene owner's suite & spa bath with frameless shower door. Convenient home office for working remotely. Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • /32

    $779,900

    Sold Sep 11, 2025

    121 Wheelhouse Way Unit 42, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $410/SF
    • 16 Days On Market

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

    121 Wheelhouse Way Unit 42, Chester, MD 21619
    • /55

      Est $468,837

      Not Listed For Sale

      905 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 2001
      905 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Jeanne Kent Northrop Realty

  • /29

    $929,990

    New Construction $41K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    540 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry & glass-front uppers.Vast center island, perfect for prepping family meals.Stunning fireplace adds character & warmth to spacious great room.Lavish primary suite & bath featuring bath barn door.Secluded Extra Suite for overnight guests.Functional home office for leisure activities.Cozy screened patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    540 Warbler Way, 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
    • /35

      Est $353,213

      Not Listed For Sale

      44B Queen Neva Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,312 Sq Ft
      • Built 1996
      44B Queen Neva Ct, Chester, MD 21619

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Raymond Johnson Berkshire Hathaway HomeServices Homesale Realty

  • /11

    $709,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in closet. Convenient covered patio with screen patio option.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36471203, 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
    • /43

      Est $603,725

      Not Listed For Sale

      1614 Postal Rd, Chester, MD 21619

      • 5 Beds
      • 2.5 Baths
      • 2,656 Sq Ft
      • Built 2003
      1614 Postal Rd, Chester, MD 21619

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /52

    $979,900

    New Construction $42K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, 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
    • /37

      Est $540,930

      Not Listed For Sale

      327 Cross Creek Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,106 Sq Ft
      • Built 2001
      327 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Violeta Aguirre Long & Foster Real Estate, Inc.

  • /18

    $849,990

    New Construction $29K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 34, Chester, MD 21619

    Gourmet kitchen with large island & built-in wall oven.Bright dining area includes a convenient dry bar.Great room features an electric fireplace.Balcony offers a perfect space for outdoor entertaining.Owner's suite includes a sitting room & balcony access.Two walk-in closets provide ample storage in the suite.Spa bath features dual vanities for added convenience.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 34, 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
    • /48

      Est $502,506

      Not Listed For Sale

      410 Hanna Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,242 Sq Ft
      • Built 2001
      410 Hanna Ct, Chester, MD 21619

      Last Sold Summary

      • 4 Days On Market

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

  • /2

    $555,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,486 Sq Ft

    532 Cross Creek Ct, Chester, MD 21619

    Eastern Shore living begins here! Welcome to 532 Cross Creek Court in the desirable Claybourne Woods community of Chester. This beautifully maintained 4-bedroom, 2.5-bath home offers plenty of space to gather, relax, and create lasting memories. Whether you're hosting gatherings, enjoying quiet evenings at home, or entertaining friends, this home provides the perfect setting. Located on Kent

    Jerilynn Montgomery Long & Foster Real Estate, Inc.

    532 Cross Creek Ct, Chester, MD 21619
  • /51

    $654,900

    Sold Sep 11, 2025

    416 Warbler Way, Chester, MD 21619

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

    Last Sold Summary

    • $329/SF
    • 23 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    416 Warbler Way, Chester, MD 21619
    • /24

      Est $380,133

      Not Listed For Sale

      10H Queen Elizabeth Ct, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      10H Queen Elizabeth Ct, Chester, MD 21619

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Jon Ridgeway Berkshire Hathaway HomeServices PenFed Realty

  • /44

    $749,990

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

    110 Warbler Way Unit 3021, 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 3021, 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
    • /53

      Est $336,130

      Not Listed For Sale

      1024 Dundee Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,360 Sq Ft
      • Built 2003
      1024 Dundee Ct, Chester, MD 21619

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /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
  • /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
    • /38

      Est $741,068

      Not Listed For Sale

      1518 Saint Marys Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1968
      1518 Saint Marys Rd, Chester, MD 21619

      Last Sold Summary

      • 189 Days On Market

      Last Listing Agent Darlene Winegardner RE/MAX Executive

  • /21

    $299,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    302 Merganser Ct Unit A, Chester, MD 21619

    Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an

    Jen Kenney Keller Williams Flagship

    302 Merganser Ct Unit A, 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
    • /39

      Est $463,000

      Not Listed For Sale

      10A Queen Elizabeth Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1983
      10A Queen Elizabeth Ct, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jen Holden Compass

  • /47

    $829,990

    New Construction
    • 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 office

    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 $858,501

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
    • /73

      Est $2,213,872

      Not Listed For Sale

      2801 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 4,297 Sq Ft
      • Built 1999
      2801 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 36 Days On Market

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

  • /29

    $700,000

    $80K 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

    $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
    • /23

      Est $329,065

      Not Listed For Sale

      1823 Chester Dr, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1976
      1823 Chester Dr, Chester, MD 21619

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Mary Wagner Cummings & Co. Realtors

  • /84

    $999,000

    $46K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    233 Kingfisher Ln, Stevensville, MD 21666

    Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living

    Tara Trout Samson Properties

    233 Kingfisher Ln, Stevensville, MD 21666
  • /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
    • /38

      Est $532,876

      Not Listed For Sale

      518 Cross Creek Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,356 Sq Ft
      • Built 2002
      518 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Darlene Winegardner RE/MAX Executive

  • /65

    $765,000

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619

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