5,231

Chester, MD Homes

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  • /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
    • /22

      Est $387,327

      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

      Last Listing Agent Kelly Alvarez Pugliese Metas Realty Group, LLC

  • /63

    $989,800

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 3,036 Sq Ft

    203 Riverside Dr, Chester, MD 21619

    Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • /44

    $764,000

    Sold Jul 27, 2026

    126 Claiborne St, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,276 Sq Ft
    • Built 2011

    Last Sold Summary

    • 3% Below List Price
    • $336/SF
    • 56 Days On Market

    Current Estimated Value $773,420

    Last Listing Agent Tara Trout Samson Properties

    126 Claiborne St, Chester, MD 21619
    • /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.

  • /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
  • /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
    • /43

      Est $415,906

      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

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /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
  • /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 $515,875

    Last Listing Agent Justin Kennedy Samson Properties

    312 Hanna 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

  • /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
  • /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 $349,144

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    206 Ringneck Ct Unit 78, 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

  • /55

    $380,000

    Open Sat 9AM - 11AM $8K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,885 Sq Ft

    6010 Bridgepointe Dr, Chester, MD 21619

    Open House, Saturday August 8th 9-11AM- Welcome to this beautifully situated two-story townhome overlooking the tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient location to Route 50 and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and

    April Heim Rosendale Realty

    6010 Bridgepointe Dr, 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 $352,851

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    9B Queen Victoria Way, 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

  • /84

    $719,900

    • 2 Beds
    • 2 Baths
    • 2,118 Sq Ft

    121 Merlin Dr, Chester, MD 21619

    Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay.Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful

    Yael Beckman Coldwell Banker Realty

    121 Merlin 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
    • /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

  • /14

    $629,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 11, Chester, MD 21619

    Open home office just off the main living space.Gourmet kitchen with central island for everyday cooking & gathering.Dining area with dry bar for easy entertaining.Electric fireplace adds warmth to the great room.Patio connects seamlessly to the great room & owner’s suite.Owner’s suite with dual closets for added storage.Owner’s bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 11, Chester, MD 21619
  • /95

    $2,350,000

    Sold May 28, 2026

    1901 Cox Neck Rd, Chester, MD 21619

    • 4 Beds
    • 4.5 Baths
    • 5,510 Sq Ft
    • Built 1997

    Last Sold Summary

    • $426/SF
    • 0 Days On Market

    Current Estimated Value $2,341,573

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1901 Cox Neck Rd, 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

  • /38

    $769,990

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

    711 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 the

    Mary Anne Kowalewski KOVO Realty

    711 Warbler Way, Chester, MD 21619
  • /17

    $724,900

    Sold Nov 10, 2025

    630 Warbler Way Unit 21, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $279/SF
    • 19 Days On Market

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

    630 Warbler Way Unit 21, 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.

  • /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
  • /30

    $332,500

    Sold Feb 20, 2026

    206 Blenny Ln, Chester, MD 21619

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $175/SF
    • 4 Days On Market

    Current Estimated Value $338,939

    Last Listing Agent Chris Craddock EXP Realty, LLC

    206 Blenny Ln, 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

  • /44

    $225,000

    Under Contract
    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    26 Queen Anne Way, Chester, MD 21619

    Bring your vision to one of the most affordable condos currently available in Queen’s Landing. This one-bedroom, one-bath unit offers approximately 640 square feet and is priced well below its tax-assessed value to reflect its original interior condition, giving buyers the flexibility to update and personalize the space to suit their own style. The condo overlooks Lake Amletto, offering a

    Julia Stevens Realty Navigator

    26 Queen Anne Way, Chester, MD 21619
  • /73

    $760,000

    Sold Oct 30, 2025

    314 Thomas White Blvd, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 2013

    Last Sold Summary

    • $317/SF
    • 47 Days On Market

    Current Estimated Value $782,169

    Last Listing Agent Kathleen Higginbotham Samson Properties

    314 Thomas White Blvd, 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

  • /50

    $595,000

    $5K PRICE DROP
    • 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
  • /51

    $500,000

    Sold Aug 22, 2025

    2008 Palm Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,283 Sq Ft
    • Built 1997

    Last Sold Summary

    • $219/SF
    • 64 Days On Market

    Current Estimated Value $526,838

    Last Listing Agent Marilyn Hendley EXP Realty, LLC

    2008 Palm Dr, Chester, MD 21619
    • /66

      Est $1,712,474

      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

  • /25

    $1,009,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    114 Kinglet Ct, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests or extended living.Home office with sliding doors for added privacy.Crown molding adds a refined touch to the great room & kitchen.Screened patio extends directly from the great room.Stacked cabinetry with glass-front uppers brings layered detail to the kitchen.Decorative feature walls add custom character to the foyer &

    K. Hovnanian Homes Builder
    114 Kinglet Ct, Chester, MD 21619
  • /28

    $375,000

    Sold Jun 03, 2026

    1150 Little Creek Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 2,200 Sq Ft
    • Built 1896

    Last Sold Summary

    • 12% Below List Price
    • $170/SF
    • 55 Days On Market

    Current Estimated Value $384,052

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1150 Little Creek 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

  • /41

    $429,900

    $70K PRICE DROP Pending
    • 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
  • /35

    $500,000

    Sold Feb 02, 2026

    1221 Cox Neck Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • Built 2012

    Last Sold Summary

    • $337/SF
    • 77 Days On Market

    Current Estimated Value $500,837

    Last Listing Agent Jorge Zea Jorge A. Zea

    1221 Cox Neck Rd, Chester, MD 21619

Showing Results 241 - 280, Page 7 of 18

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