12,063

Kent County, MD Homes

Section Image
  • /34

    $237,000 Sold Jun 30, 2025

    • 1,384 Sq Ft
    • $171/SF
    • 5 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1967

    898 Washington Ave, Chestertown, MD 21620

    This ranch property most recently was used as an accountants office and at one time a residential rental. The Village zoning allows for many uses. This could easily be turned back into a primary residence or an investment rental property. There are wood floors throughout most of the of the house with laminate flooring in the kitchen area. The HVAC heat pump is relatively new. There is a full

    Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
    • /42

      Est $723,585 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft

      22021 Kelleys Park Rd, Rock Hall, MD 21661

      22021 Kelleys Park Rd, Rock Hall, MD 21661
  • /20

    $265,000

    • 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

    Steven Knopf Engel & Völkers Annapolis

    112 Metcalf Rd, Chestertown, MD 21620
  • /37

    $525,000 Sold Jun 30, 2025

    • 3,016 Sq Ft
    • $174/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    201 Pondview Ct, Chestertown, MD 21620

    Impeccably maintained and thoughtfully upgraded, this custom-designed home is a true standout! Situated on over a half-acre just outside of town limits, this property offers the perfect blend of peace and convenience—within walking and biking distance to shopping, dining, and all the charm the town has to offer.Step inside to discover a warm, welcoming interior featuring gorgeous hardwood

    Jody Baker Cross Street Realtors LLC

    201 Pondview Ct, Chestertown, MD 21620
    • /40

      Est $422,024 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,080 Sq Ft

      8610 Camp Rd, Chestertown, MD 21620

      8610 Camp Rd, Chestertown, MD 21620
  • /3

    $145,000

    • Land
    • 1.39 Acres
    • $104,317 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
  • /150

    $13,500,000 Sold Jun 30, 2025

    • 6,144 Sq Ft
    • $2,197/SF
    • 42 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1900

    22076 Napley Green Rd, Rock Hall, MD 21661

    Introducing Napley Green Farm, an extraordinary 808-acre waterfront estate on the renowned Chester River, an expansive tributary of the Chesapeake Bay, now available for purchase for the first time in nearly a century. This rare and iconic legacy property offers unmatched privacy, breathtaking natural beauty, and incredible recreational opportunities, making it one of the most significant estates

    William Norris Select Land & Homes, LLC

    22076 Napley Green Rd, Rock Hall, MD 21661
    • /27

      Est $164,555 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,320 Sq Ft

      11580 Lynch Rd, Worton, MD 21678

      11580 Lynch Rd, Worton, MD 21678
  • /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

    $30,000 Sold Jun 30, 2025

    • Land
    • 0.21 Acre
    • $142,857 per Acre
    • 1174 Days On Market

    20765 Bayside Ave, Rock Hall, MD 21661

    Chesapeake Bay views at 8 ft elevation on this building lot. Great in-town location near restaurants, marinas and the beach. The site has existing public water and sewer service and electric on site.

    Cindy Genther Rock Hall Properties Real Estate

    20765 Bayside Ave, Rock Hall, MD 21661
    • /44

      Est $626,470 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft

      207 N Queen St, Chestertown, MD 21620

      207 N Queen St, Chestertown, MD 21620
  • /22

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    21384 E Sharp St, Rock Hall, MD 21661

    Built in 1900 and thoughtfully renovated in recent years, this 3-bedroom, 2-bathroom colonial blends timeless character with modern updates. Situated on a 1/3 acre lot, it’s just a short walk to Rock Hall’s Main Street—perfect for enjoying local favorites like Fallfest, Pirates & Wenches Weekend, shops, and dining.Start your mornings on the screened-in front porch, sipping coffee and

    Robin Fithian Rock Hall Properties Real Estate

    21384 E Sharp St, Rock Hall, MD 21661
  • /87

    $1,062,800 Sold Jun 27, 2025

    • 3,078 Sq Ft
    • $345/SF
    • 37 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1975

    22153 1st Point Rd, Chestertown, MD 21620

    Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and

    Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
    • /50

      Est $758,854 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,736 Sq Ft

      201 Radcliffe Dr, Chestertown, MD 21620

      201 Radcliffe Dr, Chestertown, MD 21620
  • /4

    $32,000

    • Land
    • 0.41 Acre
    • $78,049 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
  • /29

    $230,000 Sold Jun 27, 2025

    • 1,440 Sq Ft
    • $160/SF
    • 112 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1949

    192 Comegys St, Millington, MD 21651

    Charming Newly Renovated Cottage – Perfect for Family Living!This beautifully updated cottage reflects the pride of ownership throughout. The home features brand-new LVT flooring and carpet, creating a modern and inviting atmosphere. The kitchen has been completely transformed with all-new appliances, cabinetry, sink, lighting, and flooring, offering a fresh, functional space for culinary

    Mary Julie Long & Foster Real Estate, Inc.

    192 Comegys St, Millington, MD 21651
    • /6

      Est $398,635 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,742 Sq Ft

      403 Embert Dr, Millington, MD 21651

      403 Embert Dr, Millington, MD 21651
  • /3

    $32,000

    • Land
    • 0.41 Acre
    • $78,049 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
  • /49

    $840,000 Sold Jun 27, 2025

    • 3,355 Sq Ft
    • $250/SF
    • 182 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1963

    26865 Mallard Rd, Chestertown, MD 21620

    A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles,

    Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
    • /43

      Est $317,479 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,568 Sq Ft

      12198 Coopers Ln, Worton, MD 21678

      12198 Coopers Ln, Worton, MD 21678
  • /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
  • /28

    $549,000 Sold Jun 26, 2025

    • 2,476 Sq Ft
    • $222/SF
    • 0 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1930

    305 Washington Ave, Chestertown, MD 21620

    Wonderful Chestertown home with many endearing features including spacious rooms, hardwood floors, full basement, off street parking and more. Located across from the Washington College lawn and a block from the local hospital, this home is also ideally situated within walking distance to Historic downtown Chestertown, the Chester River, Kent Plaza, Starbucks and the Chestertown Middle and

    William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
    • /53

      Est $792,386 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,050 Sq Ft

      32483 Galena Sassafras Rd, Galena, MD 21635

      32483 Galena Sassafras Rd, Galena, MD 21635
  • /2

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 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
  • /14

    $100,000 Sold Jun 26, 2025

    • 1,686 Sq Ft
    • $59/SF
    • 11 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    25350 Worton Lynch Rd, Worton, MD 21678

    ***INVESTOR ALERT!*** LOCATED IN THE TOWN OF WORTON WITH PUBLIC WATER AND SEWER! This two story, farm house style home is in need of a renovation. Three bedrooms and one second floor bathroom. Bring your tools and give this home the makeover it is waiting for! Roof is 4 years old with a 10 year transferable warranty. CASH/HARD MONEY LOAN.

    Sheila Tome Empower Real Estate, LLC

    25350 Worton Lynch Rd, Worton, MD 21678
    • /39

      Est $363,730 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,444 Sq Ft

      107 Cedarwood Dr, Galena, MD 21635

      107 Cedarwood Dr, Galena, MD 21635
  • /2

    $15,000

    • Land
    • 0.34 Acre
    • $44,118 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
  • /71

    $745,000 Sold Jun 26, 2025

    • 3,166 Sq Ft
    • $235/SF
    • 7 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2000

    9050 Point Ln, Chestertown, MD 21620

    Welcome to this beautifully maintained 4-bedroom, 3-bath home offering serene views of the Chesapeake Bay in the quiet and friendly community of Tolchester Estates. This wonderful home is nestled just 10–15 minutes from the cities of Chestertown and Rock Hall. This close proximity provides access to shopping, restaurants, a farmers market, theater and local arts. The area abounds with

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    9050 Point Ln, Chestertown, MD 21620
    • /30

      Est $377,968 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft

      215 Devon Dr, Chestertown, MD 21620

      215 Devon Dr, Chestertown, MD 21620
  • /34

    $330,000

    • Studio
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    This duplex is a prime investment located on Washington Avenue in historic Chestertown, Maryland, offering many amenities. It is within walking distance of shopping, entertainment, schools, and medical facilities. Unit A is freshly updated with a spacious living room and dining room. The kitchen offers lots of storage and a stackable washer/dryer. It is a 2-bedroom apartment with a full bath. The

    Kathleen Brenton Brenton Realty Group

    866 Washington Ave, Chestertown, MD 21620
  • /3

    $675,000 Sold Jun 25, 2025

    • 1,945 Sq Ft
    • $347/SF
    • 2 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1904

    213 N Queen St, Chestertown, MD 21620

    A 3 car garage in the Historic District! With a rare combination of desirable features including comfortable modern amenities, this historic home will likely find its new owner quickly! Highlights of the interior include a roomy Family Room between the open concept Kitchen and the Courtyard, a formal Dining Room with a bay window, a front Living Room with gas fireplace, a formal Entry Hall, two

    Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
    • /69

      Est $544,343 Not Listed For Sale

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

      110 Camelot Dr, Chestertown, MD 21620

      110 Camelot Dr, Chestertown, MD 21620
  • /10

    $995,000

    • 2 Beds
    • 1.5 Baths
    • 1,566 Sq Ft

    29341 Glencoe Rd, Kennedyville, MD 21645

    Nestled along the tranquil banks of the Sassafras River, this charming brick fixer-upper presents a rare opportunity to own a waterfront paradise. Imagine waking up to sweeping river views and sipping coffee from the expansive enclosed porch as the sun rises.Though the home requires renovating, its potential is undeniable. Offering over 1,500 sq ft of functional space, this 2-bedroom

    Christine Catalano Coldwell Banker Realty

    29341 Glencoe Rd, Kennedyville, MD 21645
  • /40

    $252,500 Sold Jun 25, 2025

    • 2,230 Sq Ft
    • $113/SF
    • 465 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    100 N Main St, Galena, MD 21635

    Make this corner location your new Home Sweet Home!! Zoned Commercial, this zoning allows for owner occupancy, a business or both! With a little love and some updates you can have a large home in an adorable small town! Great location for a business!! Skies are truly the limit with this one of a kind property! Don't hesitate to reach out for more information today!! Thinking business??

    Jenyne Ward Patterson-Schwartz Real Estate

    100 N Main St, Galena, MD 21635
    • /14

      Est $95,555 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 572 Sq Ft

      21903 Yerkey Rd, Rock Hall, MD 21661

      21903 Yerkey Rd, Rock Hall, MD 21661
  • /15

    $625,000

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

    26933 Mallard Rd, Chestertown, MD 21620

    Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
  • /61

    $655,000 Sold Jun 24, 2025

    • 3,114 Sq Ft
    • $210/SF
    • 2 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2003

    24383 Waterview Dr, Worton, MD 21678

    Countryside elegance at its finest in this sprawling and updated Dutch Colonial in the rolling farmlands of Worton. A tasteful blend of traditional colonial character along with modern amenities creates your perfect setting for a peaceful retreat. The primary suite includes cathedral ceilings, private balcony, and a beautifully remodeled en suite bathroom. The spacious living room gracefully

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    24383 Waterview Dr, Worton, MD 21678
    • /26

      Est $417,749 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,797 Sq Ft

      21089 Haven Rd, Rock Hall, MD 21661

      21089 Haven Rd, Rock Hall, MD 21661
  • /54

    $648,750

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Just in time for the annual Downrigging Festival! See tall ships sailing the Chester River from your front porch and live in the heart of Chestertown's thriving Historic District! This versatile home has over 2,000 square feet of finished living space and was rebuilt and expanded with future customizations in mind!* The rear addition includes a sunroom/mudroom with a separate entrance connecting

    Beth Ostrander Doug Ashley Realtors, LLC

    206 S Water St, Chestertown, MD 21620
  • /45

    $459,000 Sold Jun 23, 2025

    • 2,064 Sq Ft
    • $222/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    811 S Meadowview Dr, Chestertown, MD 21620

    Charming and Immaculately Maintained One-Level HomeStep onto the inviting front porch of this meticulously cared-for home, where every detail shines both inside and out. Featuring a thoughtful and spacious floor plan, this home offers a primary suite at one end and two additional bedrooms with a full bath at the opposite end for added privacy. In the heart of the home, you'll find a cozy

    Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620

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