12,106

Kent County, MD Homes

Section Image
    • 5998 Boyce Ln, Rock Hall, MD 21661
      5998 Boyce Ln, Rock Hall, MD 21661
      5998 Boyce Ln, Rock Hall, MD 21661
      /38

      Est $454,687 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,936 Sq Ft

      5998 Boyce Ln, Rock Hall, MD 21661

      5998 Boyce Ln, Rock Hall, MD 21661
  • 349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    /47

    $395,000 Under Contract

    • Studio
    • 3,664 Sq Ft

    349 & 351 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
  • 26109 Lambs Meadow Rd, Worton, MD 21678
    26109 Lambs Meadow Rd, Worton, MD 21678
    26109 Lambs Meadow Rd, Worton, MD 21678
    /26

    $235,000 Sold Dec 29, 2025

    26109 Lambs Meadow Rd, Worton, MD 21678

    • 4 Beds
    • 2.5 Baths
    • 2,618 Sq Ft
    • Built 1920

    Last Sold Summary

    • $90/SF
    • 38 Days On Market

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    26109 Lambs Meadow Rd, Worton, MD 21678
    • 7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      /65

      Est $1,064,515 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,730 Sq Ft

      7755 Waterview Ln, Chestertown, MD 21620

      7755 Waterview Ln, Chestertown, MD 21620
  • 8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    /25

    $334,000

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

    8750 Georgetown Rd, Chestertown, MD 21620

    Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
  • 5824 Clam Cove, Rock Hall, MD 21661
    5824 Clam Cove, Rock Hall, MD 21661
    5824 Clam Cove, Rock Hall, MD 21661
    /48

    $335,500 Sold Jul 15, 2025

    5824 Clam Cove, Rock Hall, MD 21661

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 2005

    Last Sold Summary

    • $200/SF
    • 6 Days On Market

    Current Estimated Value $331,553

    Last Listing Agent Johnice Comer Compass

    5824 Clam Cove, Rock Hall, MD 21661
    • 9088 Point Ln, Chestertown, MD 21620
      9088 Point Ln, Chestertown, MD 21620
      9088 Point Ln, Chestertown, MD 21620
      /69

      Est $1,260,965 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      9088 Point Ln, Chestertown, MD 21620

      9088 Point Ln, Chestertown, MD 21620
  • 31569 Jim Davis Rd, Galena, MD 21635
    31569 Jim Davis Rd, Galena, MD 21635
    31569 Jim Davis Rd, Galena, MD 21635
    /42

    $519,999

    • 5 Beds
    • 2.5 Baths
    • 2,660 Sq Ft

    31569 Jim Davis Rd, Galena, MD 21635

    Don't miss this incredible opportunity to own your own piece of Eastern Shore! Nestled on 2 acres at 31569 Jim Davis Rd. Galena, MD, this charming property offers peace, privacy, and plenty of room to grow. Featuring spacious living areas, a beautiful rural setting, and endless potential for outdoor enjoyment - this home is ready for it's next owner to make it their own. Welcome to your country

    Lori Cichocki-Leonardi Remax Vision

    31569 Jim Davis Rd, Galena, MD 21635
  • 26743 Medders Rd, Still Pond, MD 21667
    26743 Medders Rd, Still Pond, MD 21667
    /2

    $50,000 Sold Aug 13, 2025

    26743 Medders Rd, Still Pond, MD 21667

    • 3 Beds
    • 1 Bath
    • 1,272 Sq Ft
    • Built 1900

    Last Sold Summary

    • $39/SF
    • 42 Days On Market

    Current Estimated Value $160,500

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    26743 Medders Rd, Still Pond, MD 21667
    • 7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      /22

      Est $494,176 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft

      7920 Carriage Ln, Chestertown, MD 21620

      7920 Carriage Ln, Chestertown, MD 21620
  • 0 Kinglet Rd, Chestertown, MD 21620
    0 Kinglet Rd, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • 11779 Augustine Herman Hwy, Kennedyville, MD 21645
    11779 Augustine Herman Hwy, Kennedyville, MD 21645
    11779 Augustine Herman Hwy, Kennedyville, MD 21645
    /33

    $445,000 Sold Sep 25, 2025

    11779 Augustine Herman Hwy, Kennedyville, MD 21645

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft
    • Built 1992

    Last Sold Summary

    • $209/SF
    • 75 Days On Market

    Current Estimated Value $434,792

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    11779 Augustine Herman Hwy, Kennedyville, MD 21645
    • 209 E Campus Ave, Chestertown, MD 21620
      209 E Campus Ave, Chestertown, MD 21620
      209 E Campus Ave, Chestertown, MD 21620
      /34

      Est $525,605 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft

      209 E Campus Ave, Chestertown, MD 21620

      209 E Campus Ave, Chestertown, MD 21620
  • 5750 Walnut St, Rock Hall, MD 21661
    5750 Walnut St, Rock Hall, MD 21661
    /2

    $85,000

    • Land
    • 1.12 Acres
    • $75,893 per Acre

    5750 Walnut St, Rock Hall, MD 21661

    This 1.12 acre lot is private and located within walking distance to public beach, public landing, restaurants, shopping and more.

    Robin Fithian Rock Hall Properties Real Estate

    5750 Walnut St, Rock Hall, MD 21661
  • 8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    /51

    $370,000 Sold May 08, 2025

    8605 Camp Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1968

    Last Sold Summary

    • $285/SF
    • 10 Days On Market

    Current Estimated Value $378,481

    Last Listing Agent Crystal Smith RE/MAX Executive

    8605 Camp Rd, Chestertown, MD 21620
    • 25819 Collins Ave, Chestertown, MD 21620
      25819 Collins Ave, Chestertown, MD 21620
      25819 Collins Ave, Chestertown, MD 21620
      /55

      Est $652,293 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,952 Sq Ft

      25819 Collins Ave, Chestertown, MD 21620

      25819 Collins Ave, Chestertown, MD 21620
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /24

    $765,900 New Construction

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

    37 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 bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • 26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    /15

    $555,000 Sold Jan 12, 2026

    26933 Mallard Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1956

    Last Sold Summary

    • $347/SF
    • 77 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
    • 9545 Chantilly Farm Ln, Chestertown, MD 21620
      9545 Chantilly Farm Ln, Chestertown, MD 21620
      9545 Chantilly Farm Ln, Chestertown, MD 21620
      /64

      Est $1,369,648 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      9545 Chantilly Farm Ln, Chestertown, MD 21620
  • 21139 Striper Run, Rock Hall, MD 21661
    21139 Striper Run, Rock Hall, MD 21661
    21139 Striper Run, Rock Hall, MD 21661
    /13

    $364,900 Under Contract

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

    21139 Striper Run, Rock Hall, MD 21661

    New Construction Alert! Four beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the living areas, granite counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full bath, two

    Cindy Genther Rock Hall Properties Real Estate

    21139 Striper Run, Rock Hall, MD 21661
  • 12442 Clark Rd, Worton, MD 21646
    12442 Clark Rd, Worton, MD 21646
    12442 Clark Rd, Worton, MD 21646
    /32

    $100,000 Sold Aug 28, 2025

    12442 Clark Rd, Worton, MD 21646

    • Land
    • 7.97 Acres
    • $12,547 per Acre

    Last Sold Summary

    • 34 Days On Market

    Last Listing Agent BRIAN MORRIS The Land Group

    12442 Clark Rd, Worton, MD 21646
    • 7898 Radcliffe Rd, Chestertown, MD 21620
      7898 Radcliffe Rd, Chestertown, MD 21620
      7898 Radcliffe Rd, Chestertown, MD 21620
      /46

      Est $558,328 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,264 Sq Ft

      7898 Radcliffe Rd, Chestertown, MD 21620

      7898 Radcliffe Rd, Chestertown, MD 21620
  • 21103 Striper Run, Rock Hall, MD 21661
    21103 Striper Run, Rock Hall, MD 21661
    21103 Striper Run, Rock Hall, MD 21661
    /20

    $310,000

    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    21103 Striper Run, Rock Hall, MD 21661

    Easy, low-maintenance living in the heart of Rock Hall. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite

    Courtney Chipouras TTR Sotheby's International Realty

    21103 Striper Run, Rock Hall, MD 21661
  • 0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651
    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651
    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651
    /4

    $40,000 Sold Jan 16, 2026

    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651

    • Land
    • 0.41 Acre
    • $97,561 per Acre

    Last Sold Summary

    • 146 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651
    • 11778 Augustine Herman Hwy, Kennedyville, MD 21645
      11778 Augustine Herman Hwy, Kennedyville, MD 21645
      11778 Augustine Herman Hwy, Kennedyville, MD 21645
      /29

      Est $253,886 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft

      11778 Augustine Herman Hwy, Kennedyville, MD 21645

      11778 Augustine Herman Hwy, Kennedyville, MD 21645
  • 7224 Rock Hall Rd, Rock Hall, MD 21661
    7224 Rock Hall Rd, Rock Hall, MD 21661
    7224 Rock Hall Rd, Rock Hall, MD 21661
    /12

    $164,000

    • Land
    • 2.15 Acres
    • $76,279 per Acre

    7224 Rock Hall Rd, Rock Hall, MD 21661

    Discover the charm of Kent County’s rural lifestyle on this fenced, 2.15-acre cleared lot. Perfectly situated along Rock Hall Road, the property features an existing two-car garage, a 6’x8’ storage shed, and mature trees framing vast pastoral views. With electric service and an existing well already in place, it’s ready for your vision—whether that’s building your dream home, creating a weekend

    Cindy Genther Rock Hall Properties Real Estate

    7224 Rock Hall Rd, Rock Hall, MD 21661
  • 23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    /31

    $310,000 Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Current Estimated Value $311,900

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
    • 31691 Well Bottom Rd, Galena, MD 21635
      31691 Well Bottom Rd, Galena, MD 21635
      31691 Well Bottom Rd, Galena, MD 21635
      /31

      Est $341,352 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 660 Sq Ft

      31691 Well Bottom Rd, Galena, MD 21635

      31691 Well Bottom Rd, Galena, MD 21635
  • 303 Cedar St, Chestertown, MD 21620
    303 Cedar St, Chestertown, MD 21620
    303 Cedar St, Chestertown, MD 21620
    /26

    $333,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft

    303 Cedar St, Chestertown, MD 21620

    Great Chestertown location in College Heights. Large corner lot consisting of .51 acres. This home needs to be remodeled but has great potential and a lot of floor area. The old carpet has been removed down to sub flooring. Lovely sunporch, garage, off street driveway, and entrance courtyard are just a few features! Spacious rooms too! Close to Washington College, Downtown Chestertown, and

    Hayley Norris Select Land & Homes, LLC

    303 Cedar St, Chestertown, MD 21620
  • 325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    /61

    $525,000 Sold Jun 13, 2025

    325 Devon Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 4,086 Sq Ft
    • Built 2011

    Last Sold Summary

    • $128/SF
    • 7 Days On Market

    Current Estimated Value $532,026

    Last Listing Agent Lisa Gambino Berkshire Hathaway HomeServices PenFed Realty

    325 Devon Dr, Chestertown, MD 21620
    • 5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      /44

      Est $591,645 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
  • 14 Wilson Point Rd, Galena, MD 21635
    14 Wilson Point Rd, Galena, MD 21635
    /2

    $110,000

    • Land
    • 0.75 Acre
    • $146,667 per Acre

    14 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

    14 Wilson Point Rd, Galena, MD 21635
  • 7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    /18

    $620,000 Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
    • 12445 Coopers Ln, Worton, MD 21678
      12445 Coopers Ln, Worton, MD 21678
      12445 Coopers Ln, Worton, MD 21678
      /52

      Est $1,116,092 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 3,243 Sq Ft

      12445 Coopers Ln, Worton, MD 21678

      12445 Coopers Ln, Worton, MD 21678
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /5

    $225,000 Pending

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 24383 Waterview Dr, Worton, MD 21678
    24383 Waterview Dr, Worton, MD 21678
    24383 Waterview Dr, Worton, MD 21678
    /61

    $655,000 Sold Jun 24, 2025

    24383 Waterview Dr, Worton, MD 21678

    • 3 Beds
    • 2.5 Baths
    • 3,114 Sq Ft
    • Built 2003

    Last Sold Summary

    • $210/SF
    • 2 Days On Market

    Current Estimated Value $689,033

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    24383 Waterview Dr, Worton, MD 21678
    • 8500 Broad Neck Rd, Chestertown, MD 21620
      8500 Broad Neck Rd, Chestertown, MD 21620
      8500 Broad Neck Rd, Chestertown, MD 21620
      /25

      Est $518,907 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft

      8500 Broad Neck Rd, Chestertown, MD 21620

      8500 Broad Neck Rd, Chestertown, MD 21620
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $455,000

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    Motivated sellers - bring us an offer! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    /39

    $550,000 Sold Jul 01, 2025

    25285 Foxchase Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 1992

    Last Sold Summary

    • $274/SF
    • 3 Days On Market

    Current Estimated Value $554,013

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
    • 11811 Augustine Herman Hwy, Kennedyville, MD 21645
      11811 Augustine Herman Hwy, Kennedyville, MD 21645
      11811 Augustine Herman Hwy, Kennedyville, MD 21645
      /16

      Est $288,289 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,217 Sq Ft

      11811 Augustine Herman Hwy, Kennedyville, MD 21645

      11811 Augustine Herman Hwy, Kennedyville, MD 21645

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