12,106

Kent County, MD Homes

Section Image
  • 310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    /18

    $205,000 Sold Jul 18, 2025

    310 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 2005

    Last Sold Summary

    • $169/SF
    • 24 Days On Market

    Current Estimated Value $215,279

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
    • 118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      118 Harlan Loop, Chestertown, MD 21620
      /33

      Est $482,412 Not Listed For Sale

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

      118 Harlan Loop, Chestertown, MD 21620

      118 Harlan Loop, Chestertown, MD 21620
  • 11969 Augustine Herman Hwy, Kennedyville, MD 21645
    11969 Augustine Herman Hwy, Kennedyville, MD 21645
    11969 Augustine Herman Hwy, Kennedyville, MD 21645
    /38

    $319,000

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

    11969 Augustine Herman Hwy, Kennedyville, MD 21645

    Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP

    Michele Palmer Doug Ashley Realtors, LLC

    11969 Augustine Herman Hwy, Kennedyville, MD 21645
  • 12664 Still Pond Rd, Still Pond, MD 21667
    12664 Still Pond Rd, Still Pond, MD 21667
    12664 Still Pond Rd, Still Pond, MD 21667
    /40

    $295,000 Sold Apr 17, 2025

    12664 Still Pond Rd, Still Pond, MD 21667

    • 2 Beds
    • 1.5 Baths
    • 1,352 Sq Ft
    • Built 1920

    Last Sold Summary

    • $218/SF
    • 1 Day On Market

    Current Estimated Value $297,096

    Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

    12664 Still Pond Rd, Still Pond, MD 21667
    • 105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      /58

      Est $833,857 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft

      105 S Water St, Chestertown, MD 21620

      105 S Water St, Chestertown, MD 21620
  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    /10

    $175,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    23069 Raleigh Rd, Chestertown, MD 21620

    Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Renters finally moved out and the house is being cleaned up. Roof was replaced in 2022.

    George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
  • 146 N Main St, Galena, MD 21635
    146 N Main St, Galena, MD 21635
    146 N Main St, Galena, MD 21635
    /27

    $250,000 Sold Sep 19, 2025

    146 N Main St, Galena, MD 21635

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Built 1900

    Last Sold Summary

    • $156/SF
    • 55 Days On Market

    Current Estimated Value $254,544

    Last Listing Agent John Carroll Village Real Estate Company LLC

    146 N Main St, Galena, MD 21635
    • 114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      /39

      Est $266,604 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft

      114 School Rd, Chestertown, MD 21620

      114 School Rd, Chestertown, MD 21620
  • 20992 Rock Hall Ave, Rock Hall, MD 21661
    20992 Rock Hall Ave, Rock Hall, MD 21661
    20992 Rock Hall Ave, Rock Hall, MD 21661
    /35

    $749,989

    • 4 Beds
    • 3 Baths
    • 1,912 Sq Ft

    20992 Rock Hall Ave, Rock Hall, MD 21661

    In-town waterfront living in the heart of Rock Hall — the Pearl of the Chesapeake.This beautifully updated home offers plenty of space for family and friends with 4 bedrooms and 3 full baths, all wrapped in natural landscaping that provides privacy inside and out. Enjoy peaceful water views of Swan Creek / Haven Creek Cove from the deck or sunroom, or launch your boat or kayak directly from

    Michael Roenigk Chaney Homes, LLC

    20992 Rock Hall Ave, Rock Hall, MD 21661
  • 898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    /34

    $237,000 Sold Jun 30, 2025

    898 Washington Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • Built 1967

    Last Sold Summary

    • $171/SF
    • 5 Days On Market

    Current Estimated Value $252,766

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
    • 5292 Skinners Neck Rd, Rock Hall, MD 21661
      5292 Skinners Neck Rd, Rock Hall, MD 21661
      5292 Skinners Neck Rd, Rock Hall, MD 21661
      /42

      Est $363,360 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,698 Sq Ft

      5292 Skinners Neck Rd, Rock Hall, MD 21661

      5292 Skinners Neck Rd, Rock Hall, MD 21661
  • 8 Wilson Point Rd, Galena, MD 21635
    8 Wilson Point Rd, Galena, MD 21635
    /2

    $175,000

    • Land
    • 0.75 Acre
    • $233,333 per Acre

    8 Wilson Point Rd, Galena, MD 21635

    Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style

    Aaron Clark Patterson-Schwartz-Middletown

    8 Wilson Point Rd, Galena, MD 21635
  • 6174 Dorlon Dr, Rock Hall, MD 21661
    6174 Dorlon Dr, Rock Hall, MD 21661
    6174 Dorlon Dr, Rock Hall, MD 21661
    /36

    $252,500 Sold Jul 11, 2025

    6174 Dorlon Dr, Rock Hall, MD 21661

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1994

    Last Sold Summary

    • $250/SF
    • 29 Days On Market

    Current Estimated Value $250,792

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    6174 Dorlon Dr, Rock Hall, MD 21661
    • 23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      /36

      Est $418,040 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft

      23118 Raleigh Rd, Chestertown, MD 21620

      23118 Raleigh Rd, Chestertown, MD 21620
  • LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    /3

    $9,500 Under Contract

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    Kent County Health Dept has no record of perc

    Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
  • 0 Gratitude Rd Unit MDKE2004420, Rock Hall, MD 21661
    0 Gratitude Rd Unit MDKE2004420, Rock Hall, MD 21661
    0 Gratitude Rd Unit MDKE2004420, Rock Hall, MD 21661
    /7

    $100,000 Sold Mar 28, 2025

    0 Gratitude Rd Unit MDKE2004420, Rock Hall, MD 21661

    • Land
    • 0.66 Acre
    • $151,515 per Acre

    Last Sold Summary

    • 140 Days On Market

    Last Listing Agent LaKeta Burgess NextHome Forward

    0 Gratitude Rd Unit MDKE2004420, Rock Hall, MD 21661
    • 10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      /33

      Est $325,529 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      10550 Klamath Rd, Chestertown, MD 21620

      10550 Klamath Rd, Chestertown, MD 21620
  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $35,000 Under Contract

    • Land
    • 0.9 Acre
    • $38,889 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, Chestertown, MD 21620
  • 33487 Galena Sassafras Rd, Galena, MD 21635
    33487 Galena Sassafras Rd, Galena, MD 21635
    33487 Galena Sassafras Rd, Galena, MD 21635
    /60

    $1,070,000 Sold Jan 13, 2026

    33487 Galena Sassafras Rd, Galena, MD 21635

    • 3 Beds
    • 2.5 Baths
    • 3,076 Sq Ft
    • Built 2013

    Last Sold Summary

    • $348/SF
    • 45 Days On Market

    Last Listing Agent Stephanie Coho Compass RE

    33487 Galena Sassafras Rd, Galena, MD 21635
    • 107 Dogwood Dr, Galena, MD 21635
      107 Dogwood Dr, Galena, MD 21635
      107 Dogwood Dr, Galena, MD 21635
      /35

      Est $416,780 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,804 Sq Ft

      107 Dogwood Dr, Galena, MD 21635

      107 Dogwood Dr, Galena, MD 21635
  • 12035 Galena Rd, Massey, MD 21650
    12035 Galena Rd, Massey, MD 21650
    12035 Galena Rd, Massey, MD 21650
    /54

    $399,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    12035 Galena Rd, Massey, MD 21650

    Welcome to this Hidden Gem on 1.11 Acres! Just minutes from Rt. 301, this property offers the perfect blend of peaceful rural charm and convenient access to Middletown, Dover, and Chestertown. This custom-built, one-level home features energy-efficient 2x6 construction, a partially open floor plan, 3 bedrooms, and 2 full bathrooms—providing comfortable single-story living for the whole family.

    Lona Todd Taylor Properties

    12035 Galena Rd, Massey, MD 21650
  • 5810 Clam Cove, Rock Hall, MD 21661
    5810 Clam Cove, Rock Hall, MD 21661
    /2

    $360,000 Sold Oct 17, 2025

    5810 Clam Cove, Rock Hall, MD 21661

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    Last Sold Summary

    • $221/SF
    • 1 Day On Market

    Current Estimated Value $356,797

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    5810 Clam Cove, Rock Hall, MD 21661
    • 6121 Tolchester Rd, Rock Hall, MD 21661
      6121 Tolchester Rd, Rock Hall, MD 21661
      6121 Tolchester Rd, Rock Hall, MD 21661
      /14

      Est $237,101 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,165 Sq Ft

      6121 Tolchester Rd, Rock Hall, MD 21661

      6121 Tolchester Rd, Rock Hall, MD 21661
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • 0 Griffith Dr Unit MDKE2005256, Galena, MD 21635
    0 Griffith Dr Unit MDKE2005256, Galena, MD 21635
    0 Griffith Dr Unit MDKE2005256, Galena, MD 21635
    /10

    $85,000 Sold Jul 18, 2025

    0 Griffith Dr Unit MDKE2005256, Galena, MD 21635

    • Land
    • 0.8 Acre
    • $106,250 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Jason Zang RE/MAX Chesapeake

    0 Griffith Dr Unit MDKE2005256, Galena, MD 21635
    • 23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      /7

      Est $320,966 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      23235 Myers Rd, Chestertown, MD 21620

      23235 Myers Rd, Chestertown, MD 21620
  • 21124 Striper Run, Rock Hall, MD 21661
    21124 Striper Run, Rock Hall, MD 21661
    21124 Striper Run, Rock Hall, MD 21661
    /29

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,712 Sq Ft

    21124 Striper Run, Rock Hall, MD 21661

    This beautiful home as has many upgrades. There is a lovely front porch, as well as a screened back porch. The back porch provides lots of privacy and faces trees and wildlife for viewing. The open floor plan features a kitchen and dining area, while leading from the living room with a warm propane fireplace. There's a nice pantry for storage and a half bath on the main level. Upstairs features

    Robin Fithian Rock Hall Properties Real Estate

    21124 Striper Run, Rock Hall, MD 21661
  • 12191 Galena Rd, Massey, MD 21650
    12191 Galena Rd, Massey, MD 21650
    12191 Galena Rd, Massey, MD 21650
    /32

    $85,000 Sold Sep 23, 2025

    12191 Galena Rd, Massey, MD 21650

    • 4 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 1935

    Last Sold Summary

    • $56/SF
    • 7 Days On Market

    Current Estimated Value $85,490

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    12191 Galena Rd, Massey, MD 21650
    • 4827 Piney Neck Rd, Rock Hall, MD 21661
      4827 Piney Neck Rd, Rock Hall, MD 21661
      4827 Piney Neck Rd, Rock Hall, MD 21661
      /21

      Est $266,777 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft

      4827 Piney Neck Rd, Rock Hall, MD 21661

      4827 Piney Neck Rd, Rock Hall, MD 21661
  • 10669 Chesterville Forest Rd, Millington, MD 21651
    10669 Chesterville Forest Rd, Millington, MD 21651
    10669 Chesterville Forest Rd, Millington, MD 21651
    /26

    $140,000

    • Land
    • 4.94 Acres
    • $28,340 per Acre

    10669 Chesterville Forest Rd, Millington, MD 21651

    $!$ Price Improvement!$! Looking for space? Come see this almost FIVE ACRE residential lot! Conveniently located to the town of Millington without being too close to neighbors. No HOA! Bring your vision and your builder! The front of the lot has been cleared and is ready for your dream home to be built. Public sewage lines are available with the installation of a grinder pump (Buyer expense).

    Michelle Oles Coldwell Banker Realty

    10669 Chesterville Forest Rd, Millington, MD 21651
  • 11636 Lynch Rd, Worton, MD 21678
    11636 Lynch Rd, Worton, MD 21678
    11636 Lynch Rd, Worton, MD 21678
    /26

    $285,000 Sold Aug 22, 2025

    11636 Lynch Rd, Worton, MD 21678

    • 3 Beds
    • 1.5 Baths
    • 1,482 Sq Ft
    • Built 1930

    Last Sold Summary

    • $192/SF
    • 13 Days On Market

    Current Estimated Value $277,707

    Last Listing Agent John Burke Gunther-McClary Real Estate

    11636 Lynch Rd, Worton, MD 21678
    • 23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      /13

      Est $330,966 Not Listed For Sale

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

      23399 Cloquet Rd, Chestertown, MD 21620

      23399 Cloquet Rd, Chestertown, MD 21620
  • 0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
    /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
  • 22783 McKinleyville Rd, Rock Hall, MD 21661
    22783 McKinleyville Rd, Rock Hall, MD 21661
    22783 McKinleyville Rd, Rock Hall, MD 21661
    /15

    $170,000 Sold Dec 08, 2025

    22783 McKinleyville Rd, Rock Hall, MD 21661

    • 3 Beds
    • 3 Baths
    • 1,028 Sq Ft
    • Built 1902

    Last Sold Summary

    • $165/SF
    • 72 Days On Market

    Last Listing Agent Julia Hilfiker Gunther-McClary Real Estate

    22783 McKinleyville Rd, Rock Hall, MD 21661
    • 101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      /39

      Est $327,858 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft

      101 S College Ave, Chestertown, MD 21620

      101 S College Ave, Chestertown, MD 21620
  • 82 Kent Mill Dr, Millington, MD 21651
    82 Kent Mill Dr, Millington, MD 21651
    82 Kent Mill Dr, Millington, MD 21651
    /5

    $2,750,000

    • Land
    • 103.32 Acres
    • $26,616 per Acre

    82 Kent Mill Dr, Millington, MD 21651

    103 acres of raw buildable land annexed into the Town of Millington. Approved concept plan for 213 single family lots, and 40 townhouse/duplex lots. Long road frontage along Millington Rd. Less than a quarter mile from Rt. 301. Ready to go for construction!

    John Carroll Village Real Estate Company LLC

    82 Kent Mill Dr, Millington, MD 21651
  • 8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    /59

    $775,000 Sold Nov 08, 2025

    8293 Brices Mill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,836 Sq Ft
    • Built 1900

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
    • 203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      /12

      Est $354,266 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft

      203 Radcliffe Dr, Chestertown, MD 21620

      203 Radcliffe Dr, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $165,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Taylor Properties

    141 Prospect St, Chestertown, MD 21620
  • 5823 S Hawthorne Ave, Rock Hall, MD 21661
    5823 S Hawthorne Ave, Rock Hall, MD 21661
    5823 S Hawthorne Ave, Rock Hall, MD 21661
    /47

    $539,000 Sold Jun 09, 2025

    5823 S Hawthorne Ave, Rock Hall, MD 21661

    • 5 Beds
    • 3 Baths
    • 1,410 Sq Ft
    • Built 1933

    Last Sold Summary

    • $382/SF
    • 2 Days On Market

    Current Estimated Value $538,141

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    5823 S Hawthorne Ave, Rock Hall, MD 21661

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