12,114

Kent County, MD Homes

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  • /31

    $274,000

    • 3 Beds
    • 2 Baths
    • 1,406 Sq Ft

    206 Virginia Ave, Galena, MD 21635

    Are you looking for a classic home with a ton of charm? Do you love original wood floors? Not afraid of some updating? This could just be the home for you! Screened in porch welcomes you to a beautiful foyer, and a classic living room with a fireplace that has been closed up but still provides a nice focal point. Owner is not sure if it could become a working wood-burning fireplace or not, but a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 843-7243

    206 Virginia Ave, Galena, MD 21635
  • /14

    $2,000 per month

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • House for Rent

    9919 Augustine Herman Hwy, Chestertown, MD 21620

    Property Id: 2151738This secluded home sits quietly on a family farm nestled on the bank of Morgnec creek. Built in 1990, it has 4 bedrooms and 2 baths with a full basement for storage. Although no pets are allowed, you can enjoy watching the wildlife walk through your yard while you sit outside on the deck. If interested, call or text Chris with Kendall Properties at . Credit checks and

    9919 Augustine Herman Hwy, Chestertown, MD 21620
  • /57

    $740,000 Sold May 07, 2025

    25070 E Kentfield Rd, Worton, MD 21678

    • 5 Beds
    • 3.5 Baths
    • 3,222 Sq Ft
    • Built 1995

    Last Sold Summary

    • $230/SF
    • 10 Days On Market

    Current Estimated Value $768,760

    Last Listing Agent Crystal Smith RE/MAX Executive

    25070 E Kentfield Rd, Worton, MD 21678
    • /8

      Est $82,361 Not Listed For Sale

      313 Race St, Millington, MD 21651

      313 Race St, Millington, MD 21651

      Last Sold Summary

      • 179% Above List Price
      • 241 Days On Market

      Last Sold Price $29,500

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  • /51

    $745,000

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft

    7844 Chester Ct, Chestertown, MD 21620

    Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • /12

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft
    • House for Rent

    509 Cannon St, Chestertown, MD 21620

    Welcome to 509 Cannon Street! This cozy 2-bedroom, 1-bath home has been thoughtfully updated and is ready for you to move right in. Inside, you'll find a comfortable layout and a brand-new HVAC system to keep you comfortable year-round, plus the convenience of off-street parking. Tenants are responsible for electric, town water and sewer, and internet services. To qualify, applicants must have a

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    509 Cannon St, Chestertown, MD 21620
  • /21

    $364,900 Sold Feb 26, 2026

    108 Flying Cloud Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2023

    Last Sold Summary

    • $188/SF
    • 67 Days On Market

    Current Estimated Value $358,936

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • /18

      Est $269,836 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

      • 6% Above List Price
      • $214/SF
      • 12 Days On Market

      Last Sold Price $255,000

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /21

    $509,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • /13

    $2,000 per month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Condo for Rent

    202 High St Unit E, Chestertown, MD 21620

    Property Id: 1453253Bright, open, newly remodeled, two bedroom apartment in downtown Chestertown. Open kitchen/living/dining room, flooded with light. Kitchen has stainless appliances, including dishwasher, and granite counters. Two large bedrooms, plentiful storage space. In-unit washer and dryer. The building has recently undergone extensive renovations, with many energy improvements,

    202 High St Unit E, Chestertown, MD 21620
  • /14

    $214,000 Sold Jun 18, 2025

    5855 Crosby Rd, Rock Hall, MD 21661

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2005

    Last Sold Summary

    • $159/SF
    • 82 Days On Market

    Current Estimated Value $241,407

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    5855 Crosby Rd, Rock Hall, MD 21661
    • /13

      Est $151,170 Not Listed For Sale

      5860 N Hawthorne Ave, Rock Hall, MD 21661

      5860 N Hawthorne Ave, Rock Hall, MD 21661

      Last Sold Summary

      • 12% Above List Price
      • $149/SF
      • 473 Days On Market

      Last Sold Price $135,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /26

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Here’s the opportunity buyers wait for. A classic Colonial in sought-after Coventry Farms, priced where this neighborhood rarely plays, offering space, comfort, and the chance to build equity while you live well. Step inside and you’re welcomed by a warm, traditional layout that just feels right. Accent walls add personality, the formal dining room sets the stage for holidays and celebrations,

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • /44

    $3,800 per month

    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    6119 New St Unit 2, Rock Hall, MD 21661

    Nestled on the tranquil shores of Swan Creek, this 3,000+/- sq ft waterfront home offers a rare blend of elegance, comfort and Chesapeake charm. Featuring 3 bedrooms & bonus room, 3.5 baths, and a desirable first-floor primary suite, this thoughtfully designed home invites relaxed coastal living. The great room is a showstopper with its dramatic two-story windows and cozy fireplace, framing

    Cindy Genther Rock Hall Properties Real Estate

    6119 New St Unit 2, Rock Hall, MD 21661
  • /33

    $375,000 Sold Dec 01, 2025

    907 N Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft
    • Built 2002

    Last Sold Summary

    • $204/SF
    • 83 Days On Market

    Current Estimated Value $380,311

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • /31

      Est $361,580 Not Listed For Sale

      11353 Needam Rd, Worton, MD 21678

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft
      • Built 1991
      11353 Needam Rd, Worton, MD 21678

      Last Sold Summary

      • 15% Above List Price
      • $199/SF
      • 62 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Donnis Landaverde Keller Williams Flagship

  • /47

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    24204 Drayton Landing Dr, Worton, MD 21678

    Set on two peaceful acres in the highly regarded Kinnaird’s Point community, this beautifully renovated home offers modern comfort, privacy, and access to the best of Eastern Shore living. Thoughtfully updated inside and out, the property delivers a rare combination of quality upgrades, flexible space, and community water access just minutes from Chestertown. Step inside to a bright, open

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 594-6295

    24204 Drayton Landing Dr, Worton, MD 21678
  • /14

    $1,050 per month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    425 High St Unit 4, Chestertown, MD 21620

    Property Id: 1770574Studio apartment in walking distance to Washington College and downtown Chestertown. Second floor studio apartment in recently renovated building. Updated insulation, modern windows and HVAC with original features, such as wood floors. In-building laundry and shared yard for tenants’ use. Available early June. Landlord requires a minimum 650 credit score and month

    425 High St Unit 4, Chestertown, MD 21620
  • /72

    $609,000 Sold Aug 27, 2025

    10175 John Carvill Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,155 Sq Ft
    • Built 1994

    Last Sold Summary

    • $193/SF
    • 11 Days On Market

    Current Estimated Value $635,772

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • /31

      Est $965,137 Not Listed For Sale

      4954 Huntingfield Rd, Rock Hall, MD 21661

      • 3 Beds
      • 2 Baths
      • 2,428 Sq Ft
      • Built 1961
      4954 Huntingfield Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 15% Above List Price
      • $346/SF
      • 106 Days On Market

      Last Sold Price $840,000

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /20

    $185,000 Under Contract

    • Land
    • 1.95 Acres
    • $94,872 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • /11

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Condo for Rent

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, Chestertown, MD 21620
  • /30

    $297,500 Sold May 16, 2025

    407 Jarman Ave, Galena, MD 21635

    • 3 Beds
    • 1.5 Baths
    • 2,135 Sq Ft
    • Built 1969

    Last Sold Summary

    • $139/SF
    • 23 Days On Market

    Current Estimated Value $309,117

    Last Listing Agent David Moore Real Broker, LLC

    407 Jarman Ave, Galena, MD 21635
    • /14

      Not Listed For Sale

      Lot 17 Hagy Rd, Rock Hall, MD 21661

      Lot 17 Hagy Rd, Rock Hall, MD 21661

      Last Sold Summary

      • 1 Day On Market

      Last Sold Price $145,000

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /5

    $635,000

    • Land
    • 0.09 Acre
    • $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
  • /9

    $1,450 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    425 High St Unit 5, Chestertown, MD 21620

    Property Id: 1426365A modern apartment in the heart of Chestertown. Blocks from Fountain Park and Washington College, this third floor, 2 bedroom apartment is in a building that was recently renovated to the studs, with modern windows and HVAC and original features, such as wood floors and exposed beams. In-building laundry and shared yard for tenants' use. Available immediately. Landlord

    425 High St Unit 5, Chestertown, MD 21620
  • /16

    $350,000 Sold Mar 05, 2026

    21111 Texas Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $363,864

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • /35

      Est $357,967 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

      • 8% Above List Price
      • $246/SF
      • 123 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /5

    $60,000

    • 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
  • /17

    $1,350 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    425 High St Unit 3, Chestertown, MD 21620

    Property Id: 1770537Modern apartment in the heart of Chestertown. Blocks from Fountain Park and Washington College. Second floor 1 bedroom in recently renovated building. Updated insulation, modern windows and HVAC with original features, such as wood floors. In-building laundry and shared yard for tenants’ use. Available April 1. Landlord requires a minimum 650 credit score and month

    425 High St Unit 3, Chestertown, MD 21620
  • /56

    $965,500 Sold Mar 21, 2025

    225 S Water St Unit 6, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • Built 2006

    Last Sold Summary

    • $345/SF
    • 14 Days On Market

    Current Estimated Value $1,030,313

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    225 S Water St Unit 6, Chestertown, MD 21620
    • /35

      Est $385,081 Not Listed For Sale

      10724 Foreston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1995
      10724 Foreston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $190/SF
      • 3 Days On Market

      Last Sold Price $355,675

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • /36

    $319,900

    • 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
  • /10

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 1,600 Sq Ft
    • Condo for Rent

    12775 Main St Unit LowerApartment, Still Pond, MD 21667

    Charming upper apartment located at the beautiful town Still Pond.

    12775 Main St Unit LowerApartment, Still Pond, MD 21667
  • /37

    $1,080,000 Sold May 12, 2025

    12440 Woods Rd, Worton, MD 21678

    • 4 Beds
    • 2 Baths
    • 1,955 Sq Ft
    • Built 1986

    Last Sold Summary

    • $552/SF
    • 12 Days On Market

    Current Estimated Value $1,111,661

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12440 Woods Rd, Worton, MD 21678
    • /87

      Est $1,062,787 Not Listed For Sale

      14079 Crataegus Ct, Galena, MD 21635

      • 6 Beds
      • 7 Baths
      • 5,961 Sq Ft
      • Built 1995
      14079 Crataegus Ct, Galena, MD 21635

      Last Sold Summary

      • 15% Above List Price
      • $155/SF
      • 49 Days On Market

      Last Sold Price $925,000

      Last Listing Agent Ann Marie Germano Patterson Schwartz

  • /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
  • /13

    $2,000 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    7121 Quaker Neck Rd, Chestertown, MD 21620

    This is a perfect little house in the country on a 1 acre secluded lot 1 1/2 miles from Chestertown. It is brand new on the inside with high end finishes. New Anderson windows, new doors, tile and laminate floors, SS appliances, granite countertops, Rinnai hot water heater, mini split heat pump, Owner will cut grass and maintain exterior ( 2 tomato plants) for one year, high speed internet

    7121 Quaker Neck Rd, Chestertown, MD 21620
  • /57

    $1,075,000 Sold Aug 28, 2025

    13931 Eagles Nest Farm Ln, Still Pond, MD 21667

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1987

    Last Sold Summary

    • $582/SF
    • 22 Days On Market

    Current Estimated Value $1,074,355

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    13931 Eagles Nest Farm Ln, Still Pond, MD 21667
    • /17

      Est $316,634 Not Listed For Sale

      104 Oak Leaf Dr, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 1,840 Sq Ft
      • Built 2003
      104 Oak Leaf Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $154/SF
      • 38 Days On Market

      Last Sold Price $283,000

      Last Listing Agent Krystal Zellner Crown Homes Real Estate

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