5,187

Chester, MD Homes

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    • /48

      Est $352,272 Not Listed For Sale

      5002 Bridgepointe Dr, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1995
      5002 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 5% Below List Price
      • $284/SF
      • 4 Days On Market

      Last Sold Price $369,900

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /59

    $935,990 Pending

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

    176 Flagstaff Way Unit 2424, Chester, MD 21619

    The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for low-maintenance living without sacrificing style. This home features a welcoming electric fireplace, a convenient dry bar for entertaining, and a dedicated storage room to keep everything organized. The kitchen is thoughtfully

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2424, Chester, MD 21619
  • /36

    $705,000 Sold Sep 23, 2025

    242 Peregrine Dr, Chester, MD 21619

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

    Last Sold Summary

    • $224/SF
    • 111 Days On Market

    Last Listing Agent Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
    • /24

      Est $285,019 Not Listed For Sale

      314 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1998
      314 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 8% Above List Price
      • $248/SF
      • 2 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Jimmy White Long & Foster

  • /48

    $574,900 Pending

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

    630 Warbler Way Unit 2223, Chester, MD 21619

    Introducing the Chester Lot 2223, projected to settle in May 2026. This beautiful home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights include a dry bar, electric fireplace, and a dedicated home office with lited French doors. The kitchen features a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, tile backsplash, and Quartz countertops, creating

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2223, Chester, MD 21619
  • /66

    $1,700,000 Sold Jul 11, 2025

    2921 Cox Neck Rd E, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,824 Sq Ft
    • Built 1992

    Last Sold Summary

    • $602/SF
    • 2 Days On Market

    Current Estimated Value $1,665,002

    Last Listing Agent Lynn Tuozzo Berkshire Hathaway HomeServices PenFed Realty

    2921 Cox Neck Rd E, Chester, MD 21619
    • /39

      Est $348,694 Not Listed For Sale

      7003 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1994
      7003 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 2% Below List Price
      • $273/SF
      • 28 Days On Market

      Last Sold Price $355,000

      Last Listing Agent April Heim Rosendale Realty

  • /34

    $285,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    106 Merganser Ct, Chester, MD 21619

    Welcome to easy, coastal living in Bayside on Kent Island. This beautifully updated first-floor condo offers the perfect blend of comfort, convenience, and the lifestyle everyone loves about Kent Island. Step inside to a fresh, move-in-ready interior featuring brand-new hardwood floors in the entryway and kitchen, new appliances, and plush new carpet in both bedrooms. The entire condo has been

    Crystal Smith RE/MAX Executive

    106 Merganser Ct, Chester, MD 21619
  • /23

    $350,000 Sold Feb 06, 2026

    1839 Harbor Dr, Chester, MD 21619

    • 4 Beds
    • 2 Baths
    • 2,035 Sq Ft
    • Built 1975

    Last Sold Summary

    • $172/SF
    • 119 Days On Market

    Current Estimated Value $359,367

    Last Listing Agent Greg Koch Taylor Properties

    1839 Harbor Dr, Chester, MD 21619
    • /22

      Est $383,297 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

      • 1% Above List Price
      • $271/SF
      • 53 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Kelly Alvarez Pugliese Metas Realty Group, LLC

  • /30

    $249,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    8F Queen Victoria Way, Chester, MD 21619

    Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community.Call today for your private showing.

    Linda Austin Long & Foster Real Estate, Inc.

    8F Queen Victoria Way, Chester, MD 21619
  • /65

    $740,000 Sold Jan 09, 2026

    123 Bentons Pleasure Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,791 Sq Ft
    • Built 2002

    Last Sold Summary

    • $265/SF
    • 23 Days On Market

    Current Estimated Value $761,880

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    123 Bentons Pleasure Rd, Chester, MD 21619
    • /43

      Est $487,407 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

      • 18% Below List Price
      • $302/SF
      • 3 Days On Market

      Last Sold Price $595,000

      Last Listing Agent Deborah Shiley Long & Foster

  • /28

    $299,900

    • 2 Beds
    • 1.5 Baths
    • 1,220 Sq Ft

    1905 Bayside Dr, Chester, MD 21619

    INVESTORS!! THIS COULD BE YOUR NEXT PROJECT!!Estate Sale – Peaceful Tranquility on the Eastern ShoreThere’s something special about living near the water—the smell of the bay, the calm in the air, and the sound of birds all around you. This brick rancher in the desirable Marling Farms community is right in the center of it all. With views of Crab Alley Creek and located within the Chester

    Lisa Ciofani Cummings & Co. Realtors

    1905 Bayside Dr, Chester, MD 21619
  • /38

    $829,900 Sold Jun 16, 2025

    110 Richard Ingle Way, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,380 Sq Ft
    • Built 2019

    Last Sold Summary

    • $349/SF
    • 5 Days On Market

    Current Estimated Value $838,142

    Last Listing Agent Elizabeth Arentz Coldwell Banker Realty

    110 Richard Ingle Way, Chester, MD 21619
    • /29

      Est $502,265 Not Listed For Sale

      1903 Roberta Dr, Chester, MD 21619

      • 4 Beds
      • 3 Baths
      • 2,560 Sq Ft
      • Built 1969
      1903 Roberta Dr, Chester, MD 21619

      Last Sold Summary

      • 6% Above List Price
      • $186/SF
      • 2 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Jimmy White Long & Foster

  • /27

    $979,990 New Construction

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

    307 Kingfisher Ln, Chester, MD 21619

    Welcoming foyer leads to beautiful open concept floorplan. Inviting kitchen featuring white cabinetry, quartz countertops, & center island. Spacious great room with cozy fireplace, perfect for spending time with family. Tranquil primary suite featuring detailed ceiling treatment. Polished primary bath with brushed nickel finishes & generous walk-in closet. Convenient Extra Suite & home office off

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, Chester, MD 21619
  • /48

    $705,000 Sold Mar 28, 2025

    209 Harrier Way, Stevensville, MD 21666

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • Built 2024

    Last Sold Summary

    • $253/SF
    • 131 Days On Market

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    209 Harrier Way, Stevensville, MD 21666
    • /43

      Est $392,773 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

      • 2% Above List Price
      • $203/SF
      • 3 Days On Market

      Last Sold Price $385,900

      Last Listing Agent Crystal Smith RE/MAX

  • /48

    $574,900 Pending

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

    630 Warbler Way Unit 2222, Chester, MD 21619

    Chester|| Available May 2026 This home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Standout features include a dry bar, an electric fireplace, and a dedicated home office with lited French doors. The kitchen is thoughtfully designed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, and a tile backsplash, all accented by quartz countertops. The flooring

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2222, Chester, MD 21619
  • /55

    $829,900 Sold Jul 30, 2025

    218 Switchgrass Way Unit 1732, Chester, MD 21619

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

    Last Sold Summary

    • $437/SF
    • 17 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1732, Chester, MD 21619
    • /67

      Est $577,460 Not Listed For Sale

      1606 Chester Rd, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 2,030 Sq Ft
      • Built 1972
      1606 Chester Rd, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $275/SF
      • 231 Days On Market

      Last Sold Price $559,000

      Last Listing Agent Judy Murray Long & Foster

  • /8

    $445,000 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    23F Queen Victoria Way, Chester, MD 21619

    Offered for the first time in over 30 years, this lovingly maintained 2-bedroom, 2-bath residence is filled with warmth, history, and memories that have been cherished by the same family for decades. Perfectly positioned in sought-after Queen’s Landing, the home captures truly exceptional, direct views of the marina basin, marina fairway, and the Chester River—an ever-changing waterfront backdrop

    Jennifer Thomas RE/MAX Executive

    23F Queen Victoria Way, Chester, MD 21619
  • /56

    $760,000 Sold Apr 10, 2025

    119 Cavalier Ct, Chester, MD 21619

    • 3 Beds
    • 4 Baths
    • 2,959 Sq Ft
    • Built 2019

    Last Sold Summary

    • $257/SF
    • 30 Days On Market

    Current Estimated Value $802,808

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

    119 Cavalier Ct, Chester, MD 21619
    • /33

      Est $480,642 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

      • 2% Below List Price
      • $219/SF
      • 3 Days On Market

      Last Sold Price $490,000

      Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

  • /32

    $454,900 Pending

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    1401 Calvert Rd, Chester, MD 21619

    MARLING FARMS -Waterviews of Crab Alley Bay - PRICE REDUCED -Brick Rancher- All on ONE LEVEL - Beautifully landscaped 3/4 acre lot that backs to trees - fenced patio area - 2 bedrooms with lots of windows and large closets - 2 full baths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer cabinetry, beverage

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
  • /41

    $405,000 Sold Nov 14, 2025

    1903 Churchhill Ln, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 1,682 Sq Ft
    • Built 1984

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $407,715

    Last Listing Agent Lois Alberti Alberti Realty, LLC

    1903 Churchhill Ln, Chester, MD 21619
    • /12

      Est $360,148 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

      • 8% Above List Price
      • $349/SF
      • 16 Days On Market

      Last Sold Price $335,000

      Last Listing Agent susan taylor Chaney Homes, LLC

  • /32

    $530,000 Pending

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

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell! Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel appliances, custom

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • /88

    $689,900 Sold Nov 12, 2025

    201 Switchgrass Way Unit 1421, Chester, MD 21619

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

    Last Sold Summary

    • $265/SF
    • 12 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1421, Chester, MD 21619
    • /48

      Est $287,779 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

      • 11% Above List Price
      • $235/SF
      • 8 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • /79

    $499,000 Under Contract

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

    170 Harrier Way Unit 22, Chester, MD 21619

    For a limited time, the seller is offering $4,000 toward the capital contribution fee—an incredible opportunity to move into the sought-after Four Seasons at Kent Island lifestyle just in time for warmer days on the Chesapeake Bay. This beautifully maintained, turnkey condo offers the perfect blend of comfort and sophistication. The thoughtfully designed floor plan features two spacious bedrooms,

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • /28

    $389,000 Sold May 13, 2025

    33 F Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 1988

    Last Sold Summary

    • $232/SF
    • 68 Days On Market

    Last Listing Agent Alex Martinez The Agency DC

    33 F Queen Anne Way, Chester, MD 21619
    • /53

      Est $443,696 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

      • 8% Above List Price
      • $252/SF
      • 54 Days On Market

      Last Sold Price $412,000

      Last Listing Agent Teresa Klopfer Remax 100

  • /47

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades.Welcome to Bayside living at its finest. This meticulously maintained

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • /14

    $21,000 Sold Apr 18, 2025

    18J Piney Narrows Rd, Chester, MD 21619

    • 600 Sq Ft
    • Built 1980

    Last Sold Summary

    • $35/SF
    • 9 Days On Market

    Current Estimated Value $20,464

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    18J Piney Narrows Rd, Chester, MD 21619
    • /23

      Est $279,654 Not Listed For Sale

      108 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,050 Sq Ft
      • Built 1994
      108 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • 14% Above List Price
      • $233/SF
      • 3 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Crystal Smith RE/MAX

  • /28

    $499,000

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

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Step into the good life in the sought-after Four Seasons on Kent Island, where low-maintenance living meets waterfront vibes. This 2-bedroom, 2-bath home offers spacious one-level living with an open, airy layout, freshly painted interiors, and a stylish kitchen featuring a modern glass subway tile backsplash—perfect for entertaining or unwinding after a day on the Shore. The 1-car garage plus

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • /26

    $685,813 Sold Jun 12, 2025

    1770 Harbor Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths

    Last Sold Summary

    • 52 Days On Market

    Current Estimated Value $635,082

    Last Listing Agent George Bailey Keller Williams Flagship

    1770 Harbor Dr, Chester, MD 21619
    • /13

      Est $380,382 Not Listed For Sale

      3A Queen Victoria Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1985
      3A Queen Victoria Ct, Chester, MD 21619

      Last Sold Summary

      • 36% Above List Price
      • $222/SF

      Last Sold Price $280,000

      Last Listing Agent Kathleen Higginbotham Samson Properties

Showing Results 161 - 200, Page 5 of 18

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