12,109

Kent County, MD Homes

Section Image
  • /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

    Current Estimated Value $173,853

    Last Listing Agent Julia Hilfiker Gunther-McClary Real Estate

    22783 McKinleyville Rd, Rock Hall, MD 21661
    • /36

      Est $444,606 Not Listed For Sale

      23118 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1970
      23118 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $234/SF
      • 9 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • /9

    $364,900 Open Sat 12PM - 2PM

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

    21133 Striper Run, Rock Hall, MD 21661

    New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious

    Cindy Genther Rock Hall Properties Real Estate

    21133 Striper Run, Rock Hall, MD 21661
  • /34

    $665,000 Sold Mar 30, 2026

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $416/SF
    • 8 Days On Market

    Current Estimated Value $644,310

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    • /33

      Est $344,887 Not Listed For Sale

      10550 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2006
      10550 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13% Above List Price
      • $217/SF
      • 2 Days On Market

      Last Sold Price $305,000

      Last Listing Agent David Moore Real Broker, LLC

  • /3

    $125,000

    • Land
    • 0.75 Acre
    • $166,667 per Acre

    12 Wilson Point Rd, Galena, MD 21635

    Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

    Aaron Clark Patterson-Schwartz-Middletown

    12 Wilson Point Rd, Galena, MD 21635
  • /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

    Current Estimated Value $782,617

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
    • /35

      Est $400,874 Not Listed For Sale

      107 Dogwood Dr, Galena, MD 21635

      • 3 Beds
      • 2 Baths
      • 1,804 Sq Ft
      • Built 2000
      107 Dogwood Dr, Galena, MD 21635

      Last Sold Summary

      • 3% Above List Price
      • $216/SF
      • 3 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Mark Saunders Integrity Real Estate

  • /90

    $2,400,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • /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 $527,818

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    5823 S Hawthorne Ave, Rock Hall, MD 21661
    • /14

      Est $238,514 Not Listed For Sale

      6121 Tolchester Rd, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,165 Sq Ft
      • Built 1920
      6121 Tolchester Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 45% Above List Price
      • $142/SF
      • 84 Days On Market

      Last Sold Price $164,900

      Last Listing Agent Matthew Altizer ANR Realty, LLC

  • /38

    $319,000 Under Contract

    • 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
  • /31

    $490,000 Sold Mar 25, 2026

    14525 John Peel Rd, Galena, MD 21635

    • 3 Beds
    • 2.5 Baths
    • 1,932 Sq Ft
    • Built 1991

    Last Sold Summary

    • 1% Above List Price
    • $254/SF
    • 3 Days On Market

    Current Estimated Value $484,302

    Last Listing Agent Jason Hinish Corner House Realty

    14525 John Peel Rd, Galena, MD 21635
    • /7

      Est $327,018 Not Listed For Sale

      23235 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23235 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $214/SF
      • 12 Days On Market

      Last Sold Price $299,900

      Last Listing Agent David Moore Real Broker, LLC

  • /3

    $175,000

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

    8 Wilson Point Rd, Galena, MD 21635

    Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

    Aaron Clark Patterson-Schwartz-Middletown

    8 Wilson Point Rd, Galena, MD 21635
  • /2

    $11,000 Sold Feb 19, 2026

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    • Land
    • 2 Acres
    • $5,500 per Acre

    Last Sold Summary

    • 806 Days On Market

    Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    • /21

      Est $268,794 Not Listed For Sale

      4827 Piney Neck Rd, Rock Hall, MD 21661

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1954
      4827 Piney Neck Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 12% Above List Price
      • $226/SF
      • 7 Days On Market

      Last Sold Price $239,000

      Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

  • /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
  • /20

    $310,000 Sold Jul 14, 2025

    10490 Worton Rd, Worton, MD 21678

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • $294/SF
    • 3 Days On Market

    Current Estimated Value $316,184

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    10490 Worton Rd, Worton, MD 21678
    • /13

      Est $329,547 Not Listed For Sale

      23399 Cloquet Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2004
      23399 Cloquet Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $198/SF
      • 41 Days On Market

      Last Sold Price $300,000

      Last Listing Agent David Moore Real Broker, LLC

  • /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
  • /47

    $359,000 Sold Feb 03, 2026

    8833 Georgetown Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 1900

    Last Sold Summary

    • $221/SF
    • 76 Days On Market

    Current Estimated Value $354,803

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
    • /35

      Est $359,012 Not Listed For Sale

      7071 Rock Hall Rd, Rock Hall, MD 21661

      • 3 Beds
      • 1.5 Baths
      • 1,340 Sq Ft
      • Built 1993
      7071 Rock Hall Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 9% Above List Price
      • $246/SF
      • 123 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /24

    $395,000 New Construction

    • 4 Beds
    • 2 Baths
    • 2,162 Sq Ft

    21733 Centennial Ln, Rock Hall, MD 21661

    Welcome to Crosby Woods, a charming new community located less than a mile from downtown Rock Hall. This thoughtfully designed neighborhood features just ten single-family homes situated on a quiet cul-de-sac with shared open space and no HOA. This brand-new 2,162 sq. ft. rancher offers comfortable one-level living with four bedrooms and two full bathrooms. The home features beautifully finished

    Sarah Ulrick Rock Hall Properties Real Estate

    21733 Centennial Ln, Rock Hall, MD 21661
  • /32

    $700,000 Sold Oct 22, 2025

    26889 Morgnec Rd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft
    • Built 1966

    Last Sold Summary

    • $356/SF
    • 156 Days On Market

    Current Estimated Value $706,036

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
    • /39

      Est $317,814 Not Listed For Sale

      101 S College Ave, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft
      • Built 1920
      101 S College Ave, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $295/SF
      • 1 Day On Market

      Last Sold Price $305,435

      Last Listing Agent Jimmy White Long & Foster

  • /4

    $250,000

    • Land
    • 0.85 Acre
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • /7

    $80,000 Sold Dec 22, 2025

    5700 Johnsontown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1900

    Last Sold Summary

    • $70/SF
    • 107 Days On Market

    Current Estimated Value $137,102

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • /12

      Est $353,916 Not Listed For Sale

      203 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1963
      203 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 54% Above List Price
      • $131/SF
      • 12 Days On Market

      Last Sold Price $230,111

      Last Listing Agent Alex Modaressi RE/MAX

  • /29

    $390,000 Under Contract

    • 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
  • /27

    $310,000 Sold Dec 16, 2025

    21119 Striper Run, Rock Hall, MD 21661

    • 3 Beds
    • 4 Baths
    • 1,628 Sq Ft
    • Built 1996

    Last Sold Summary

    • $190/SF
    • 408 Days On Market

    Current Estimated Value $306,402

    Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

    21119 Striper Run, Rock Hall, MD 21661
    • /25

      Est $358,314 Not Listed For Sale

      5924 Henry Ave, Rock Hall, MD 21661

      • 3 Beds
      • 2 Baths
      • 1,530 Sq Ft
      • Built 1953
      5924 Henry Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 24% Above List Price
      • $190/SF
      • 97 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

  • /31

    $345,000

    • 3 Beds
    • 1.5 Baths
    • 1,215 Sq Ft

    11350 Lynch Rd, Worton, MD 21678

    Welcome home to this well-maintained 3-bedroom, 11⁄2-bath brick rancher that combines classic charm with a ready-to-go layout, making it yours to make your own. Nestled in the peaceful countryside just minutes from Chestertown and an easy commute to Middletown, this home offers the best of rural living with open views and fresh country air. Step inside to find a cozy living room, hallway and

    Grace Crockett Doug Ashley Realtors, LLC

    11350 Lynch Rd, Worton, MD 21678
  • /20

    $125,000 Sold Mar 02, 2026

    423 Calvert St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1992

    Last Sold Summary

    • $110/SF
    • 112 Days On Market

    Current Estimated Value $134,808

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
    • /93

      Est $845,257 Not Listed For Sale

      30741 Duck Puddle Rd, Kennedyville, MD 21645

      • 5 Beds
      • 3.5 Baths
      • 5,118 Sq Ft
      • Built 1999
      30741 Duck Puddle Rd, Kennedyville, MD 21645

      Last Sold Summary

      • 13% Above List Price
      • $147/SF
      • 109 Days On Market

      Last Sold Price $750,000

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • /29

    $230,000 Sold Jun 27, 2025

    192 Comegys St, Millington, MD 21651

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft
    • Built 1949

    Last Sold Summary

    • $160/SF
    • 112 Days On Market

    Current Estimated Value $238,055

    Last Listing Agent Mary Julie Long & Foster Real Estate, Inc.

    192 Comegys St, Millington, MD 21651
    • /29

      Est $367,156 Not Listed For Sale

      21053 Striper Run, Rock Hall, MD 21661

      • 4 Beds
      • 2 Baths
      • 1,256 Sq Ft
      • Built 2013
      21053 Striper Run, Rock Hall, MD 21661

      Last Sold Summary

      • 2% Above List Price
      • $287/SF
      • 0 Days On Market

      Last Sold Price $359,900

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /48

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /2

    $5,800 Sold Apr 14, 2025

    0 Golts Rd, Galena, MD 21635

    • Land
    • 0.5 Acre
    • $11,600 per Acre

    Last Sold Summary

    • 271 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Golts Rd, Galena, MD 21635

Showing Results 161 - 200, Page 5 of 18

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