12,111

Kent County, MD Homes

Section Image Section Image
    • /17

      Est $251,823 Not Listed For Sale

      104 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2023
      104 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • 25 Days On Market
      • Last Sold Price $234,900
      • Dec 15, 2023

      Last Listing Agent David Moore Real Broker, LLC

  • /28

    $398,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,798 Sq Ft

    107 Boxwood Ln, Galena, MD 21635

    Welcome to 107 Boxwood Lane in the Dogwood Village community. This home is nicely situated at the end of a cul-de-sac with a spacious triangular lot. The backyard is nicely edged with foliage, making a private oasis. The home offers convenient one-floor living. Large open living space, stainless steel appliances, wood floors and natural light. A bonus sunroom is just steps away from the dining

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 724-1207

    107 Boxwood Ln, Galena, MD 21635
  • /21

    $315,000 Sold Mar 13, 2026

    11047 Bottom Rd, Worton, MD 21678

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2023

    Last Sold Summary

    • $262/SF
    • 20 Days On Market

    Current Estimated Value $312,827

    Last Listing Agent Jeff Guthrie Taylor Properties

    11047 Bottom Rd, Worton, MD 21678
    • /22

      Not Listed For Sale

      11335 Needam Rd, Worton, MD 21678

      • 3 Beds
      • 1.5 Baths
      • 1,288 Sq Ft
      • Built 1970
      11335 Needam Rd, Worton, MD 21678

      Last Sold Summary

      • $116/SF
      • 2 Days On Market
      • Last Sold Price $150,000
      • Jun 12, 2023

      Last Listing Agent Brittany Fox RE/MAX

  • /28

    $340,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 2,055 Sq Ft

    202 Waldo Dr, Chestertown, MD 21620

    A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that’s been well-loved. The layout flows

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 971-7157

    202 Waldo Dr, Chestertown, MD 21620
  • /26

    $287,500 Sold Dec 05, 2025

    7483 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 35 Days On Market

    Current Estimated Value $284,668

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • /59

      Est $308,903 Not Listed For Sale

      128 N Main St, Galena, MD 21635

      • 3 Beds
      • 1.5 Baths
      • 1,560 Sq Ft
      • Built 1920
      128 N Main St, Galena, MD 21635

      Last Sold Summary

      • 14% Above List Price
      • $173/SF
      • 6 Days On Market
      • Last Sold Price $270,000
      • Nov 26, 2024

      Last Listing Agent Amber Durand Patterson-Schwartz Real Estate

  • /37

    $319,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent

    Agent Photo

    Ryan Fitzwater

    RE/MAX Advantage Realty

    (410) 835-4609

    24775 Langford Rd, Chestertown, MD 21620
  • /5

    $25,000 Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Current Estimated Value $184,667

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • /27

      Est $443,121 Not Listed For Sale

      21357 Belair Ave, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,008 Sq Ft
      • Built 2010
      21357 Belair Ave, Chestertown, MD 21620

      Last Sold Summary

      • 23% Above List Price
      • $179/SF
      • 1 Day On Market
      • Last Sold Price $360,000
      • May 07, 2024

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /51

    $1,975,000

    • 5 Beds
    • 3 Baths
    • 3,915 Sq Ft

    14183 Roberts Dr, Galena, MD 21635

    Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5094

    14183 Roberts Dr, Galena, MD 21635
  • /38

    $319,000 Sold Apr 30, 2026

    11969 Augustine Herman Hwy, Kennedyville, MD 21645

    • 4 Beds
    • 2 Baths
    • 2,520 Sq Ft
    • Built 1920

    Last Sold Summary

    • $127/SF
    • 145 Days On Market

    Current Estimated Value $315,073

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    11969 Augustine Herman Hwy, Kennedyville, MD 21645
    • /34

      Est $280,152 Not Listed For Sale

      7499 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2018
      7499 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 19% Above List Price
      • $191/SF
      • 14 Days On Market
      • Last Sold Price $235,000
      • Nov 30, 2023

      Last Listing Agent Petra Quinn Realty Navigator

  • /32

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-3661

    226 S Water St, Chestertown, MD 21620
  • /10

    $175,000 Sold Mar 10, 2026

    23069 Raleigh Rd, Chestertown, MD 21620

    • 2 Beds
    • 1,160 Sq Ft
    • Built 1967

    Last Sold Summary

    • $151/SF
    • 184 Days On Market

    Current Estimated Value $186,360

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • /35

      Est $357,886 Not Listed For Sale

      21424 Catholic Ave, Rock Hall, MD 21661

      • 4 Beds
      • 1.5 Baths
      • 1,247 Sq Ft
      • Built 1966
      21424 Catholic Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 59% Above List Price
      • $180/SF
      • 32 Days On Market
      • Last Sold Price $225,000
      • Jun 22, 2023

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /24

    $813,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • /2

    $9,500 Sold Aug 19, 2025

    0 Millbrook Dr, Chestertown, MD 21620

    • Land
    • 21,780 Sq Ft
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    0 Millbrook Dr, Chestertown, MD 21620
    • /12

      Est $499,572 Not Listed For Sale

      102 N Main St, Galena, MD 21635

      • 3 Beds
      • 1.5 Baths
      • 1,416 Sq Ft
      • Built 1900
      102 N Main St, Galena, MD 21635

      Last Sold Summary

      • 284% Above List Price
      • $92/SF
      • 260 Days On Market
      • Last Sold Price $130,000
      • Oct 18, 2018

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /29

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • /2

    $90,000 Sold May 30, 2025

    0 None Unit MDKE2005014, Chestertown, MD 21620

    • Land
    • 13.46 Acres
    • $6,686 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
    • /34

      Not Listed For Sale

      10967 Bottom Rd, Worton, MD 21678

      • 3 Beds
      • 1 Bath
      • 904 Sq Ft
      • Built 1983
      10967 Bottom Rd, Worton, MD 21678

      Last Sold Summary

      • $314/SF
      • 38 Days On Market
      • Last Sold Price $284,000
      • Jul 31, 2024

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

  • /23

    $839,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • /39

    $415,000 Sold Sep 17, 2025

    21311 Lee St, Rock Hall, MD 21661

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1979

    Last Sold Summary

    • $240/SF
    • 13 Days On Market

    Current Estimated Value $402,232

    Last Listing Agent Sarah King Cross Street Realtors LLC

    21311 Lee St, Rock Hall, MD 21661
    • /26

      Est $334,636 Not Listed For Sale

      24990 Heather Ln, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 2022
      24990 Heather Ln, Worton, MD 21678

      Last Sold Summary

      • 10% Above List Price
      • $237/SF
      • 43 Days On Market
      • Last Sold Price $305,000
      • Feb 19, 2025

      Last Listing Agent Jordan Larigan LPT Realty, LLC

  • /26

    $753,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, Chestertown, MD 21620
  • /20

    $220,000 Sold Sep 22, 2025

    300 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • $183/SF
    • 147 Days On Market

    Current Estimated Value $226,030

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • /18

      Est $279,500 Not Listed For Sale

      11951 Kennedyville Rd, Kennedyville, MD 21645

      • 3 Beds
      • 1 Bath
      • 1,194 Sq Ft
      • Built 1920
      11951 Kennedyville Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 10% Above List Price
      • $214/SF
      • 12 Days On Market
      • Last Sold Price $255,000
      • Feb 14, 2025

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /25

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • /44

    $680,000 Sold Sep 30, 2025

    8978 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • $178/SF
    • 1 Day On Market

    Current Estimated Value $696,265

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • /13

      Est $146,516 Not Listed For Sale

      5860 N Hawthorne Ave, Rock Hall, MD 21661

      5860 N Hawthorne Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 9% Above List Price
      • $149/SF
      • 473 Days On Market
      • Last Sold Price $135,000
      • Feb 28, 2025

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /39

    $1,250,000

    • 4 Beds
    • 5.5 Baths
    • 3,527 Sq Ft

    5979 Lawton Ave, Rock Hall, MD 21661

    This spectacular waterfront retreat offers over 3,500 square feet of living space on 0.76 acres, ideally located within the town limits of Rock Hall. With an elevator, five bedrooms an office and four and a half baths, there is abundant space for family, guests, and effortless entertaining.The ground level welcomes you with a spacious game room, sitting area, exercise space, and an oversized

    Cindy Genther Rock Hall Properties Real Estate

    5979 Lawton Ave, Rock Hall, MD 21661
  • /73

    $910,000 Sold Jul 31, 2025

    12083 Blacks Station Rd, Kennedyville, MD 21645

    • 5 Beds
    • 4.5 Baths
    • 2,542 Sq Ft
    • Built 1990

    Last Sold Summary

    • $358/SF
    • 11 Days On Market

    Current Estimated Value $904,009

    Last Listing Agent Joe Hickman Cross Street Realtors LLC

    12083 Blacks Station Rd, Kennedyville, MD 21645
    • /70

      Est $738,703 Not Listed For Sale

      147 Carriage Heath, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,148 Sq Ft
      • Built 2015
      147 Carriage Heath, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $333/SF
      • 20 Days On Market
      • Last Sold Price $715,000
      • Oct 15, 2024

      Last Listing Agent Yael Beckman Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /22

    $749,900

    • Land
    • 7.9 Acres
    • $94,924 per Acre

    21610 Hidden Creek Dr, Rock Hall, MD 21661

    Enjoy a long, secluded driveway to 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Greys Inn Creek. The home features vaulted ceilings and has access to a private pier and dock; its perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this

    Mike Arajakis Whitetail Properties Real Estate

    21610 Hidden Creek Dr, Rock Hall, MD 21661
  • /52

    $795,000 Sold Jul 14, 2025

    211 David Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft
    • Built 1963

    Last Sold Summary

    • $181/SF
    • 2 Days On Market

    Current Estimated Value $817,511

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • /27

      Est $520,576 Not Listed For Sale

      106 Church Aly, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,416 Sq Ft
      • Built 1880
      106 Church Aly, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $350/SF
      • 7 Days On Market
      • Last Sold Price $495,000
      • Dec 13, 2024

      Last Listing Agent Cindy Genther Rock Hall Properties

  • /6

    $3,665,000

    • Land
    • 113 Acres
    • $32,434 per Acre

    22537 Shipyard Ln, Rock Hall, MD 21661

    Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between

    Sue Hudson National Land Realty

    22537 Shipyard Ln, Rock Hall, MD 21661
  • /35

    $210,000 Sold Oct 03, 2025

    19 1st Ave, Betterton, MD 21610

    • 2 Beds
    • 1 Bath
    • 504 Sq Ft
    • Built 1951

    Last Sold Summary

    • $417/SF
    • 3 Days On Market

    Current Estimated Value $214,833

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    19 1st Ave, Betterton, MD 21610
    • /56

      Est $448,228 Not Listed For Sale

      10570 Cogar Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft
      • Built 2010
      10570 Cogar Rd, Chestertown, MD 21620

      Last Sold Summary

      • 28% Above List Price
      • $122/SF
      • 118 Days On Market
      • Last Sold Price $349,000
      • Apr 26, 2024

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home