12,094

Kent County, MD Homes

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  • /6

    $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
  • /41

    $391,000 Sold Dec 01, 2025

    • 2,000 Sq Ft
    • $196/SF
    • 83 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2025

    21739 Centennial Ln, Rock Hall, MD 21661

    OPEN HOUSE, SATURDAY, NOV 1, 10-12 PM! 100% financing is available! The seller offers up to $10,000 toward closing costs or a rate buy down. This brand new home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 4 bedrooms, 2 bathrooms and 2,000 square feet of single-level living. It offers luxury vinyl floors,

    Donnis Landaverde Keller Williams Flagship

    21739 Centennial Ln, Rock Hall, MD 21661
    • /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
  • /20

    $185,000

    • 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • /55

    $394,000 Sold Nov 26, 2025

    • 1,264 Sq Ft
    • $312/SF
    • 68 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    25070 Lambs Meadow Rd, Worton, MD 21678

    Looking for NEW construction and the convenience of one-story living? Look No Further! At the end of aprivate driveway is this elegantly designed 3 BR 2 bath Country Craftsman nestled on a 0.25 acre lot. Amulti pitched roofline tops this beautiful home which displays craftsmanship and attention to detail. Thisoasis which has a keyless entry two-car attached garage is adorned with

    Antoinette Brooks EXP Realty, LLC

    25070 Lambs Meadow Rd, Worton, MD 21678
    • /17

      Est $280,279 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • /77

    $4,221,800 Sold Nov 24, 2025

    • 9,852 Sq Ft
    • $429/SF
    • 219 Days On Market
    • 5 Beds
    • 8 Baths
    • Built 2001

    23620 Lands End Rd, Chestertown, MD 21620

    Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of the Langford and Chester River. This light filled custom built home and property captures the essence of serene living on Maryland's Eastern Shore. One of only 4 premiere properties at the end of Quaker Neck, often called "Kent County's Gold Coast" is sited to take advantage of the natural landscape with

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, 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
  • /29

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • /31

    $285,000 Sold Nov 21, 2025

    • 1,404 Sq Ft
    • $203/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2000

    5086 Skinners Neck Rd, Rock Hall, MD 21661

    Charming Fully Renovated 3 Bed, 2 Bath Rancher in Rock Hall, Move-In Ready! Welcome to your dream home in Skinners Neck, nestled on the peaceful outskirts of Rock Hall, Maryland; a coastal gem known for its small town charm and waterfront lifestyle. This fully renovated 3-bedroom, 2-bath rancher offers modern comfort, spacious living, and a prime location just minutes from local stores,

    Taylor Leaverton Benson & Mangold, LLC

    5086 Skinners Neck Rd, Rock Hall, MD 21661
    • /59

      Est $284,048 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
  • /23

    $839,500 New Construction

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

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • /47

    $872,500 Sold Nov 21, 2025

    • 2,582 Sq Ft
    • $338/SF
    • 32 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2005

    10761 Kasota Rd, Chestertown, MD 21620

    Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
    • /27

      Est $431,652 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
  • /26

    $753,500 New Construction

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

    36 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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, Chestertown, MD 21620
  • /9

    $890,000 Sold Nov 21, 2025

    • 1,566 Sq Ft
    • $568/SF
    • 98 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1950

    29341 Glencoe Rd, Kennedyville, MD 21645

    NO LOT LINE ADJUSTMENT!!! Nestled along the serene banks of the Sassafras River, this charming brick fixer-upper offers a rare opportunity to create your dream waterfront retreat. Set on a sprawling 2.58-acre lot with 175 feet of private shoreline, the property boasts breathtaking river views, peaceful natural surroundings, and direct deep-water access. Inside, the home offers over 1,500 square

    Christine Catalano Coldwell Banker Realty

    29341 Glencoe Rd, Kennedyville, MD 21645
    • /34

      Est $311,591 Not Listed For Sale

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

      7499 Poplar Ave, Chestertown, MD 21620

      7499 Poplar Ave, Chestertown, MD 21620
  • /24

    $813,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • /25

    $230,000 Sold Nov 20, 2025

    • 1,140 Sq Ft
    • $202/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2023

    126 Metcalf Rd, Chestertown, MD 21620

    Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside

    Brenda Fornos Taylor Properties

    126 Metcalf Rd, Chestertown, MD 21620
    • /12

      Est $507,156 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
  • /25

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 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 ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • /32

    $546,500 Sold Nov 20, 2025

    • 1,632 Sq Ft
    • $335/SF
    • 10 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1930

    28781 Valley Rd, Kennedyville, MD 21645

    Originally built in 1930. Completely updated and tastefully renovated. Perfect year round or seasonal cottage. In the very special private community of Kenmtore Park. Year round activities for all. Nightly get together at the Big Pier to capture the most beautiful sunsets on the Sassafras River. Morning coffee is served on the deck off of the kitchen. Invite friends over for a day at the beach

    Patricia Kern Gunther-McClary Real Estate

    28781 Valley Rd, Kennedyville, MD 21645
    • /34

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 904 Sq Ft

      10967 Bottom Rd, Worton, MD 21678

      10967 Bottom Rd, Worton, MD 21678
  • /90

    $2,500,000

    • 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
  • /2

    $140,000 Sold Nov 17, 2025

    • Land
    • 2.64 Acres
    • $53,030 per Acre
    • 120 Days On Market

    0 Private Spry ( Lot 50) Ln, Worton, MD 21678

    Build your dream home on this 2.64-acre cul-de-sac homesite in the peaceful Montabello Hills II community of Worton, MD. This is an approved buildable lot that is ready for your vision, . Enjoy privacy, natural beauty, and a quiet setting just minutes from Chestertown and the Chesapeake Bay. Approved Site Plan SRA Approved Low HOA Fees Ideal for Custom or Vacation Home Located in scenic Kent

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    0 Private Spry ( Lot 50) Ln, Worton, MD 21678
    • /70

      Est $705,125 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
  • /20

    $165,000

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

    423 Calvert St, Chestertown, MD 21620

    READY TO FINISH!!! LVP Flooring installed on 10/04/2025 on the main and upper levels. Materials, fixtures, applicances cabinetry, washer/dryer and new toilet on site and ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • /49

    $329,000 Sold Nov 17, 2025

    • 1,720 Sq Ft
    • $191/SF
    • 23 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1920

    228 Phelps Ave, Galena, MD 21635

    Nestled on a spacious corner lot in the heart of Galena, this historic American Four Square blends timeless character with modern updates. Known for its barn-style outbuildings—perfect for storage, workshop space, or future restoration—this property offers both charm and functionality. Outdoor living is at its best with a beautifully restored in-ground swimming pool, ideal for entertaining or

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    228 Phelps Ave, Galena, MD 21635
    • /56

      Est $441,537 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • /6

    $3,665,000

    • Land
    • 113 Acres
    • $32,434 per Acre

    22537 Shipyard Ln, Rock Hall, MD 21661

    Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between

    Sue Hudson National Land Realty

    22537 Shipyard Ln, Rock Hall, MD 21661
  • /5

    $25,000 Sold Nov 14, 2025

    • Land
    • 0.34 Acre
    • $73,529 per Acre
    • 29 Days On Market

    23628 Canvasback Rd, Chestertown, MD 21620

    Waterfront lot in the community of Chesapeake Landing, just outside of Chestertown. This lot has failed previous perc tests and is most likely not buildable.

    Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
    • /25

      Not Listed For Sale

      10 School House Rd, Millington, MD 21651

      10 School House Rd, Millington, MD 21651
  • /29

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    12400 Woods Rd, Worton, MD 21678

    Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by

    Jack Boniface Cross Street Realtors LLC

    12400 Woods Rd, Worton, MD 21678
  • /73

    $435,000 Sold Nov 14, 2025

    • 2,000 Sq Ft
    • $218/SF
    • 192 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    1 Bayview Rd, Betterton, MD 21610

    Back on the market at no fault of seller. Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    1 Bayview Rd, Betterton, MD 21610
    • /27

      Est $417,119 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,707 Sq Ft

      5837 Clam Cove, Rock Hall, MD 21661

      5837 Clam Cove, Rock Hall, MD 21661
  • /40

    $598,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /49

    $905,000 Sold Nov 14, 2025

    • 1,820 Sq Ft
    • $497/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1993

    10050 Forrest Ln, Chestertown, MD 21620

    Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
    • /7

      Est $93,653 Not Listed For Sale

      5246 Eastern Neck Rd, Rock Hall, MD 21661

      5246 Eastern Neck Rd, Rock Hall, MD 21661
  • /30

    $429,000

    • 4 Beds
    • 2 Baths
    • 1,794 Sq Ft

    32287 Quinn Rd, Massey, MD 21650

    Just off Route 301 for commuters, but located in the country with privacy, space for animals, hobbies, and entertaining. Large detached garage with storage space above, full unfinished basement, fenced pasture area, and inground pool. So much potential here, come with vision and make it your own!

    John Carroll Village Real Estate Company LLC

    32287 Quinn Rd, Massey, MD 21650

Showing Results 41 - 80, Page 2 of 18

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