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Kent County MD Homes for Sale

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  • /69

    $539,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • /16

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Metcalf Rd, Chestertown, MD 21620

    Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of the home is the spectacular eat-in

    Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • /55

    $1,000,000

    • 4 Beds
    • 2.5 Baths
    • 4,504 Sq Ft

    13699 Still Pond Rd, Still Pond, MD 21667

    Endless Possibilities on 20 Rolling Acres at Dawnwood Farm — Discover the magic of Maryland’s Eastern Shore at this captivating 20-acre farmstead, where heritage charm meets modern comfort. Whether you're a dreamer, a doer, or a little of both, this property offers something extraordinary for every kind of buyer—from adventure-seeking families and aspiring homesteaders to seasoned growers and

    Liddy Campbell TTR Sotheby's International Realty

    13699 Still Pond Rd, Still Pond, MD 21667
  • /21

    $179,000

    • 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

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 267-4230

    21316 Persimmon Dr, Chestertown, MD 21620
  • /54

    $399,900

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

    12035 Galena Rd, Massey, MD 21650

    Welcome to this Hidden Gem on 1.11 Acres! Just minutes from Rt. 301, this property offers the perfect blend of peaceful rural charm and convenient access to Middletown, Dover, and Chestertown. This custom-built, one-level home features energy-efficient 2x6 construction, a partially open floor plan, 3 bedrooms, and 2 full bathrooms—providing comfortable single-story living for the whole family.

    Lona Todd Taylor Properties

    12035 Galena Rd, Massey, MD 21650
  • /27

    $325,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, Chestertown, MD 21620
  • /21

    $519,000

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

    116 Harlan Loop, Chestertown, MD 21620

    $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$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

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • /2

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    5898 Williams St, Rock Hall, MD 21661

    Welcome to 5898 Williams Street, Rock Hall, MD! This 5-acre cleared parcel offers an exciting development opportunity in the heart of Rock Hall. With public water and sewer available, the property provides excellent development potential. Formerly zoned MCI, it is now zoned residential under the newly adopted Rock Hall 2040 Comprehensive Plan, opening the door for possible subdivision. Situated

    Cindy Genther Rock Hall Properties Real Estate

    5898 Williams St, 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
  • /2

    $10,000

    • Land
    • 0.55 Acre
    • $18,182 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Lot 60, 61, 62. No perc on file at this time. Property was tested years ago and did not perc.Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek.

    Michelle Abplanalp Rosendale Realty

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /21

    $40,000

    • Land
    • 1 Acre
    • $40,000 per Acre

    0 Allens Ln Unit MDKE2005580, Rock Hall, MD 21661

    Welcome to your slice of country solitude! This wooded 1-acre lot comes with a sewer allocation already in place so no septic headaches here. You’ll just need to add a well... unless, of course, you discover one hiding on the property. (The county has no records, but there’s an old house/structure tucked in the trees, so who knows what secrets it holds.)The sewer is serviced by a grinder

    Micheal Vakas EXP Realty, LLC

    0 Allens Ln Unit MDKE2005580, Rock Hall, MD 21661
  • /2

    $40,000

    • Land
    • 0.34 Acre
    • $117,647 per Acre

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620

    Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

    Jo Ann Edwards The Hogans Agency

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
  • /41

    $394,999 New Construction

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    21733 Centennial Ln, Rock Hall, MD 21661

    OPEN HOUSE, SATURDAY, NOV 1, 10-12 PM! 100% financing is available! The seller is offering a special incentive with in-house financing that includes 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 four bedrooms and two bathrooms with

    James Schaecher Keller Williams Flagship

    21733 Centennial Ln, Rock Hall, MD 21661
  • /20

    $249,950

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed for

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • /3

    $120,000

    • Land
    • 1.39 Acres
    • $86,331 per Acre

    LOT 4 Piney Neck Rd, Rock Hall, MD 21661

    Build Your Waterfront Dream Retreat – Lot 4 Piney Neck Rd, Rock Hall, MDDiscover a rare opportunity to own 1.39 acres of serene, partially wooded land in the heart of Rock Hall, Maryland — a beloved Chesapeake Bay waterfront town known for boating, fishing, and peaceful Eastern Shore living. This prime parcel offers deeded right-of-way access to Davis Creek and includes shared use of a

    David Sordelet Real Broker, LLC

    LOT 4 Piney Neck Rd, Rock Hall, MD 21661
  • /54

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 3,935 Sq Ft

    251 Devon Dr, Chestertown, MD 21620

    NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that

    Debbie Meikle Doug Ashley Realtors, LLC

    251 Devon Dr, Chestertown, MD 21620
  • /2

    $9,000

    • Land
    • 0.61 Acre
    • $14,754 per Acre

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620

    Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    0 Sandpiper Rd Unit MDKE2005542, Chestertown, MD 21620
  • /4

    $39,750

    • Land
    • 0.41 Acre
    • $96,951 per Acre

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

    Wooded, 0.4+ acre buildable lot on Chesterville Forest Rd with sewer allocation already paid—a $11,800 value! Buyer just needs to install a grinder pump and connect. Survey and setbacks included for easy due diligence. Conveniently located near Rt. 301 for quick access north to Middletown, DE, or south to the Bay Bridge.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Chesterville Forest Rd Unit PARCEL 84A, 1, Massey, MD 21651
  • /3

    $39,750

    • Land
    • 0.41 Acre
    • $96,951 per Acre

    0 Chesterville Forest Rd Unit PARCEL 60, 1, Massey, MD 21651

    Wooded, 0.4+ acre buildable lot on Chesterville Forest Rd with sewer allocation already paid—a $11,800 value! Buyer just needs to install a grinder pump and connect. Survey and setbacks included in documents for easy due diligence. Conveniently located near Rt. 301 for quick access north to Middletown, DE, or south to the Bay Bridge.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Chesterville Forest Rd Unit PARCEL 60, 1, Massey, MD 21651
  • /16

    $167,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Cross Street Realtors LLC

    141 Prospect St, Chestertown, MD 21620
  • /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620
  • /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
  • /10

    $128,000

    • Land
    • 1.64 Acres
    • $78,049 per Acre

    0 Crosby Rd, Rock Hall, MD 21661

    This nice wooded lot on Crosby Rd is 0.2 mile to Long Cove Marina and Long Cove County Landing. Rock Hall Yacht Club is just around the bend on McKinleyville Rd. With 142 ft of road frontage and a wooded buffer, there's lots of privacy and room to roam. The property is near navigable water, but not in the flood plain. Winter water views are possible. There's a public sewer allocation and hook up

    Cindy Genther Rock Hall Properties Real Estate

    0 Crosby Rd, Rock Hall, MD 21661
  • /40

    $545,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    21090 W Sharp St Unit 133, Rock Hall, MD 21661

    Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern

    Lynn Hilfiker Gunther-McClary Real Estate

    21090 W Sharp St Unit 133, Rock Hall, MD 21661
  • /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
  • /2

    $150,000

    • Land
    • 0.75 Acre
    • $200,000 per Acre

    11 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

    11 Wilson Point Rd, Galena, MD 21635
  • /25

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,156 Sq Ft

    11944 Augustine Herman Hwy, Kennedyville, MD 21645

    This classic home has been beautifully renovated and updated while maintaining the original charm. Enjoy cooking meals in the gourmet kitchen with stainless steel appliances, double wall oven and downdraft cooktop. The kitchen leads to the formal dining room and large open living space, perfect for entertaining. There are four bedrooms, two full bathrooms, and a third-floor bonus room, which

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 892-1081

    11944 Augustine Herman Hwy, Kennedyville, MD 21645
  • /2

    $125,000

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

    12 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

    12 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
  • /2

    $175,000

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

    9 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

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

    $125,000

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

    13 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

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

    $150,000

    • Land
    • 0.75 Acre
    • $200,000 per Acre

    10 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

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

    $175,000

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

    8 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

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

    $150,000

    • Land
    • 0.75 Acre
    • $200,000 per Acre

    6 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

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

    $175,000

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

    7 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

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

    $120,000

    • Land
    • 0.75 Acre
    • $160,000 per Acre

    3 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

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

    $135,000

    • Land
    • 0.75 Acre
    • $180,000 per Acre

    5 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

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

    $125,000

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

    4 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

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

    $9,000

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

    0 Kinglet Rd, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • /2

    $9,000

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

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

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