12,134

Kent County, MD Homes

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  • /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • /43

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    13755 Shallcross Wharf Rd, Kennedyville, MD 21645

    Wonderful 2 Bedroom / 2 Bath Cape Cod on a Bluff with Water View. This open concept home has great views and presents the opportunity to live off the beaten path. If living in and amongst nature interests you this home could be perfect. Hardwood floors, modern kitchen, full UN-finished basement, and the opportunity to watch and enjoy the seasons overlooking a tributary of the Sassafras River.

    Michael Davis Phoenix Real Estate

    13755 Shallcross Wharf Rd, Kennedyville, MD 21645
  • /2

    $1,100,000

    Sold Jun 30, 2025

    209 N Water St, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,909 Sq Ft
    • Built 1900

    Last Sold Summary

    • $378/SF
    • 0 Days On Market

    Current Estimated Value $1,156,728

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
    • /32

      Est $376,325

      Not Listed For Sale

      216 Silver Heel Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,724 Sq Ft
      • Built 2022
      216 Silver Heel Rd, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

  • /5

    $60,000

    Pending
    • Land
    • 3 Acres
    • $20,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • /10

    $1,400 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,040 Sq Ft
    • Townhouse for Rent

    103 S Lynchburg St, Chestertown, MD 21620

    This charming townhouse offers comfortable living in the heart of Chestertown. The main level features a roomy living space, an eat-in kitchen with a convenient half bath, and first-floor laundry. Upstairs, you'll find two bedrooms and a full bathroom. Enjoy the added bonus of one off-street parking spot. Move-in ready now. ***Tenants will be responsible for electric, town water and sewer, and

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    103 S Lynchburg St, Chestertown, MD 21620
  • /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 $314,181

    Last Listing Agent Jeff Guthrie Taylor Properties

    11047 Bottom Rd, Worton, MD 21678
    • /42

      Est $329,893

      Not Listed For Sale

      306 Cedar St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1959
      306 Cedar St, Chestertown, MD 21620

      Last Sold Summary

      • 55 Days On Market

  • /34

    $384,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    23416 Cloquet Rd, Chestertown, MD 21620

    Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches. Step

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    (443) 920-7517

    23416 Cloquet Rd, 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 $285,711

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • /22

      Est $278,909

      Not Listed For Sale

      25241 Porters Grove Rd, Worton, MD 21678

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1978
      25241 Porters Grove Rd, Worton, MD 21678

      Last Sold Summary

      • 31 Days On Market

  • /46

    $540,000

    Open House 7/02
    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft

    21186 Chesapeake Ave, Rock Hall, MD 21661

    Deck was washed and stained on 5/20/26! Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike ride, or drive away. Nature lovers

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    (667) 247-9594

    21186 Chesapeake Ave, Rock Hall, MD 21661
  • /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 $186,667

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • /15

      Est $384,993

      Not Listed For Sale

      5814 Clam Cove, Rock Hall, MD 21661

      • 3 Beds
      • 2.5 Baths
      • 1,626 Sq Ft
      • Built 2024
      5814 Clam Cove, Rock Hall, MD 21661

      Last Sold Summary

      • 0 Days On Market

  • /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
  • /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 $313,546

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    11969 Augustine Herman Hwy, Kennedyville, MD 21645
    • /8

      Est $73,092

      Not Listed For Sale

      313 Race St, Millington, MD 21651

      313 Race St, Millington, MD 21651

      Last Sold Summary

      • 241 Days On Market

  • /65

    $760,000

    • 3 Beds
    • 2 Baths
    • 2,058 Sq Ft

    34203 Cypress Rd, Millington, MD 21651

    Two parcels combine for a total of 5.22 acres, offering a rare blend of space, versatility, and opportunity. The separate 3.21-acre parcel is perc-approved and buildable, currently used for hunting, and includes its own right-of-way for private access. The main home sits on 2.012 acres and has been lovingly maintained and thoughtfully updated over the years. Inside, you’ll find a spacious and

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    (410) 634-7639

    34203 Cypress Rd, Millington, MD 21651
  • /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 $187,318

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
    • /24

      Not Listed For Sale

      1 Bayview Rd Unit 3, Betterton, MD 21610

      • 2 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1989
      1 Bayview Rd Unit 3, Betterton, MD 21610

      Last Sold Summary

      • 1 Day On Market

  • /34

    $282,000

    Open House 7/05 $13K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,000 Sq Ft

    6374 Rock Hall Rd, Rock Hall, MD 21661

    Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    (667) 222-3358

    6374 Rock Hall Rd, Rock Hall, MD 21661
  • /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
    • /17

      Est $255,573

      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

      • 25 Days On Market

  • /31

    $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
  • /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 $431,981

    Last Listing Agent Sarah King Cross Street Realtors LLC

    21311 Lee St, Rock Hall, MD 21661
    • /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

      • 2 Days On Market

  • /4

    $245,000

    • Studio
    • 2,718 Sq Ft

    11989 Augustine Herman Hwy, Kennedyville, MD 21645

    Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 846-6502

    11989 Augustine Herman Hwy, Kennedyville, MD 21645
  • /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 $227,337

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
    • /59

      Est $294,143

      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

      • 6 Days On Market

  • /7

    $86,000

    • Land
    • 18,730 Sq Ft
    • $200,000 per Acre

    0 River Bend Ln, Millington, MD 21651

    Located on the upper Chester River in Millington, River Bend Lane offers the perfect blend of convenience and waterfront lifestyle just seconds from Route 301 for easy commuting. Skip the hassle and expense of a perc test — the owners have already secured public water and sewer allocation, making the building process that much easier. Enjoy kayaking, fishing, and peaceful river views right from

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    (410) 413-1519

    0 River Bend Ln, Millington, MD 21651
  • /3

    $7,200

    Sold Jun 04, 2026

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $21,176 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 457 Days On Market

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    • /27

      Est $400,310

      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

      • 1 Day On Market

  • /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
  • /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 $706,233

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
    • /34

      Est $281,658

      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

      • 14 Days On Market

  • /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
  • /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 $915,493

    Last Listing Agent Joe Hickman Cross Street Realtors LLC

    12083 Blacks Station Rd, Kennedyville, MD 21645
    • /12

      Est $498,298

      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

      • 260 Days On Market

  • /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
  • /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 $817,732

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620

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