12,108

Kent County, MD Homes

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  • /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
  • /20

    $1,575 per month

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

    517 High St Unit C, Chestertown, MD 21620

    Property Id: 2282226Welcome to this spacious 2-bedroom, 1-bath apartment located on the second floor of a classic Chestertown multi-family home. This well-laid-out unit offers comfortable living with attractive architectural details and plenty of natural light throughout. Residents also have access to a shared deck, fenced yard, and welcoming front porch, all just minutes from downtown

    517 High St Unit C, 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 $762,110

    Last Listing Agent Crystal Smith RE/MAX Executive

    25070 E Kentfield Rd, Worton, MD 21678
    • /24

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,600 Sq Ft

      1 Bayview Rd Unit 3, Betterton, MD 21610

      1 Bayview Rd Unit 3, Betterton, MD 21610
  • /31

    $350,000

    • 4 Beds
    • 2 Baths
    • 1,499 Sq Ft

    21305 Haven Rd, Rock Hall, MD 21661

    This beautiful home is updated and ideally located near marinas and downtown, offering both convenience and tranquility. Key features include:Location: Within town limits, close to marinas and downtown, with easy access to Swan Creek and public boat ramp 4 bedrooms, 2 bathroomsMain Floor: Features Three spacious bedrooms, updated kitchen with granite countertops and stainless steel

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    (410) 648-2974

    21305 Haven Rd, Rock Hall, MD 21661
  • /6

    $1,600 per month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    11149 Old Worton Rd, Worton, MD 21678

    Unit #6 is Available Now – Move-in Ready! This beautifully updated 2nd-floor 3 bed & 1 bath apartment has been recently renovated with modern finishes, including brand-new drywall, fresh paint, luxury vinyl plank (LVP) flooring, upgraded cabinets, stylish countertops, and new appliances throughout. The apartment is spacious, offering comfort and convenience in a desirable location. Key Features:

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11149 Old Worton Rd, Worton, MD 21678
  • /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 $237,431

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    5855 Crosby Rd, Rock Hall, MD 21661
    • /17

      Est $255,987 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • /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
  • /9

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    5785 Downey Ave, Rock Hall, MD 21661

    Property Id: 1632359This 2 bedroom 1 bath home is all 1 level living on a quiet dead end street. Walking distance to shops & restaurants in the heart of Rock Hall. Propane cooking and on demand hot water, so you never run out. If interested, call Chris with Kendall Properties to schedule a showing at . Credit check must be at least 600 and background check fairly clean.

    5785 Downey Ave, 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

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • /22

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,288 Sq Ft

      11335 Needam Rd, Worton, MD 21678

      11335 Needam Rd, Worton, MD 21678
  • /21

    $169,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21316 Persimmon Dr, Chestertown, MD 21620

    Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 267-4230

    21316 Persimmon Dr, Chestertown, MD 21620
  • /16

    $1,550 per month

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

    229 N Kent St Unit 3, Chestertown, MD 21620

    Beautifully renovated Two Bedroom/1 Bath Unit. Remodeled down to studs with new gourmet eat-in kitchen with walk-in pantry. Both bedrooms almost equal size, new bathroom, full size washer/dryer added. Central air and heat, new double pane windows, water included in rent, off-street parking. Two Blocks from High Street and Two Blocks from Washington College

    Peter Braun Long & Foster Real Estate, Inc.

    229 N Kent St Unit 3, 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 $612,376

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • /59

      Est $286,352 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,560 Sq Ft

      128 N Main St, Galena, MD 21635

      128 N Main St, Galena, MD 21635
  • /26

    $475,000

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

    110 Trafford Dr, Chestertown, MD 21620

    Discover an incredible opportunity in the highly sought-after Coventry Farms community—one of the rare chances to get into this neighborhood for under $500K. This inviting Colonial offers the perfect blend of comfort, charm, and value, with plenty of room to make it your own and build equity over time. Step inside to a warm and welcoming layout featuring thoughtfully designed accent walls, a

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • /20

    $1,400 per month

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

    517 High St Unit B, Chestertown, MD 21620

    Property Id: 2282225Welcome to your inviting 1-bedroom, 1-bath apartment in the heart of Chestertown. Located in a classic multi-family home on High Street, this residence offers a comfortable layout with attractive architectural details throughout. Outdoor features include a shared deck, a fenced yard, and a welcoming front porch. This well-located rental is available for $1,400 per

    517 High St Unit B, 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 $308,257

    Last Listing Agent David Moore Real Broker, LLC

    407 Jarman Ave, Galena, MD 21635
    • /27

      Est $430,762 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,008 Sq Ft

      21357 Belair Ave, Chestertown, MD 21620

      21357 Belair Ave, Chestertown, MD 21620
  • /31

    $299,900

    • 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
  • /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
  • /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 $990,721

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    225 S Water St Unit 6, Chestertown, MD 21620
    • /34

      Est $280,264 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      7499 Poplar Ave, Chestertown, MD 21620

      7499 Poplar Ave, Chestertown, MD 21620
  • /47

    $799,000

    • 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
  • /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 $1,060,085

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    12440 Woods Rd, Worton, MD 21678
    • /12

      Est $503,106 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,416 Sq Ft

      102 N Main St, Galena, MD 21635

      102 N Main St, Galena, MD 21635
  • /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
  • /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
  • /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 $1,076,347

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    13931 Eagles Nest Farm Ln, Still Pond, MD 21667
    • /34

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 904 Sq Ft

      10967 Bottom Rd, Worton, MD 21678

      10967 Bottom Rd, Worton, MD 21678
  • /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
  • /54

    $400,000 Sold Mar 28, 2025

    14111 Turners Point Rd, Kennedyville, MD 21645

    • 4 Beds
    • 2.5 Baths
    • 3,187 Sq Ft
    • Built 1936

    Last Sold Summary

    • $126/SF
    • 256 Days On Market

    Current Estimated Value $487,558

    Last Listing Agent Kerry D'Azevedo Integrity Real Estate

    14111 Turners Point Rd, Kennedyville, MD 21645
    • /70

      Est $719,008 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,148 Sq Ft

      147 Carriage Heath, Chester, MD 21619

      147 Carriage Heath, Chester, MD 21619
  • /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
  • /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 $1,148,911

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
    • /27

      Est $508,433 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,416 Sq Ft

      106 Church Aly, Chestertown, MD 21620

      106 Church Aly, Chestertown, MD 21620
  • /36

    $269,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    24339 Chestertown Rd, Chestertown, MD 21620

    One level rancher with new HVAC, new 200 amp electric panel. The water conditioner is owned, and the water heater is about 2 years old. There is a wall mounted propane heater, but with the new HVAC this can be removed if desired. The current owner says the wall unit heated the entire home for him. The home has beautiful farmland views, mature trees, and has a lovely cottage feel. Last sold in

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 584-3270

    24339 Chestertown Rd, Chestertown, MD 21620
  • /35

    $330,000 Sold Feb 26, 2025

    7071 Rock Hall Rd, Rock Hall, MD 21661

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft
    • Built 1993

    Last Sold Summary

    • $246/SF
    • 123 Days On Market

    Current Estimated Value $348,693

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    7071 Rock Hall Rd, Rock Hall, MD 21661

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