12,153

Kent, MD Homes

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  • /39

    $299,900 Pending

    • 3 Beds
    • 1.5 Baths
    • 2,296 Sq Ft

    389 Cypress St, Millington, MD 21651

    UNDER CONTRACT! Open House for 7/12 is now cancelled. Welcome to 389 Cypress Street, a delightful home brimming with character and charm. Whether you are looking for a starter home or downsizing, have a look at this terrific home! Updating this home has been a true joy. This owner fell in love with the unique features of this lovely house, from the original wood floors and vintage

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 291-8216

    389 Cypress St, Millington, MD 21651
  • /2

    $2,500 per month

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • House for Rent

    14073 Augustine Herman Hwy, Galena, MD 21635

    Property Id: 2003928This is 1800 square feet of a beautiful 4 bedroom 3 full baths with heated flooring. Full dry basement with plenty of storage with a large deck. Directly across from the Kitty Knight House restaurant and marinas in Galena Md. This property also has a separate beautiful 1 bedroom 1 bath apartment with vaulted ceilings that has been carefully and thoughtfully renovated

    14073 Augustine Herman Hwy, Galena, MD 21635
  • /63

    $390,500 Sold Aug 08, 2025

    • 1,457 Sq Ft
    • $268/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1874

    137 N Main St, Galena, MD 21635

    Historic St. Andrews Chapel - Galena, MD - circa 1874. Architecturally stunning one of a kind former Episcopal wayside chapel converted to fabulous residence. From the exterior you will notice the attention to detail that this home has received during massive updates and renovations over the last few years. Full exterior restoration of original board and batten siding, standing seam metal

    John Carroll Village Real Estate Company LLC

    137 N Main St, Galena, MD 21635
    • /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
  • /24

    $299,900 Pending

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • /9

    $1,450 per month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, seperate dining room, galley kitchen, full bathroom and bedroom. Unit is available immediately, utilities included: electric, water and sewer. Security

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • /53

    $600,000 Sold Aug 08, 2025

    • 5,001 Sq Ft
    • $120/SF
    • 0 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1977

    605 Mill Ln, Galena, MD 21635

    Bring everyone along to experience this stunning property, offering a combination of space, style, & functionality. The 3-bedroom, 2-bath main home has been thoughtfully designed to cater to both relaxation & entertainment, featuring expansive living areas & high-end finishes throughout. The spacious primary suite is a true retreat at the end of the main hall, thoughtfully designed with comfort

    Liddy Campbell TTR Sotheby's International Realty

    605 Mill Ln, Galena, MD 21635
    • /17

      Est $251,229 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • /27

    $260,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft

    5810 Judefind Ave, Rock Hall, MD 21661

    Adorable Cottage featuring 2BR/1.5BA, just over a quarter acre of land! Built in 2010, cute as a button, large front porch and another on the back to match. Large attic (potential for expansion), on-demand water heater, gutter filters, HVAC, shed in back for storage/lawn mower, mature asparagus bed in front yard! Living space is open with a nicely appointed kitchen and the covered back porch

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 222-2354

    5810 Judefind Ave, Rock Hall, MD 21661
  • /16

    $1,300 per month

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

    200 Cannon St Unit 1A, Chestertown, MD 21620

    Ground floor apartment in nice, safe, quiet, upscale area 2 blocks from river and waterfront park, 1 block from downtown (in Historic District). Suitable for 1 persons. No pets or smoking.

    200 Cannon St Unit 1A, Chestertown, MD 21620
  • /24

    $280,000 Sold Aug 07, 2025

    • 896 Sq Ft
    • $312/SF
    • 10 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1955

    21363 Indiana Ave, Chestertown, MD 21620

    Welcome to this low-maintenance coastal cottage in Tolchester, just two blocks from the community beach on the Chesapeake Bay. Set on nearly a half-acre, this home has been completely renovated inside and out. Inside, you'll find three bedrooms and one and a half baths. Recent upgrades include a new well, new water filtration and softener system, and an encapsulated crawlspace with

    Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, 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
  • /26

    $299,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,482 Sq Ft

    11636 Lynch Rd, Worton, MD 21678

    Classic farmhouse on half an acre! Three spacious bedrooms, central air and updated LVT flooring in the living area. Enjoy mornings on the front porch and dinners on the spacious back deck. There is more than enough room in the yard for a garden or other outdoor activities. The large pole barn could be used as a workshop and has plenty of space for additional storage. Plus, there are two smaller

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 412-8908

    11636 Lynch Rd, Worton, MD 21678
  • /10

    $1,450 per month

    • 1 Bed
    • 1 Bath
    • 1,455 Sq Ft
    • Condo for Rent

    128 N Queen St Unit 4, Chestertown, MD 21620

    Move in ready 2nd floor apartment in Downtown Chestertown. One spacious bedroom, full bathroom, living area and a step-up cove/office space. Conveniently located within walking distance to the Chester River. Utilities included with the exception of Internet/Cable. All applicants apply through Rent Spree.

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 4, Chestertown, MD 21620
  • /60

    $725,000 Sold Aug 05, 2025

    • 4,023 Sq Ft
    • $180/SF
    • 134 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1989

    24576 Langford Rd, Chestertown, MD 21620

    Designed by noted architectural historian and restoration consultant, Michael Bourne, Highfield exemplifies a deep appreciation and intimate knowledge of historic architectural composition and its elements. With its steep pitch hip roof, catslide roof slope on one end, tall chimney, and enclosed front entry, in form and style, Highfield is reminiscent of the vernacular farmhouses of southeastern

    Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
    • /4

      Est $82,765 Not Listed For Sale

      32072 Shorewood Rd, Galena, MD 21635

      32072 Shorewood Rd, Galena, MD 21635
  • /45

    $310,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    Are you ready to make this lovely well-maintained rancher home yours? It has new HVAC, a new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Three-bedroom, one full bath, large open kitchen/dining and cozy living room. Enjoy time in the large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, 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
  • /46

    $585,000 Sold Aug 05, 2025

    • 2,819 Sq Ft
    • $208/SF
    • 209 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1943

    5738 Beach Rd, Rock Hall, MD 21661

    Spectacular Chesapeake Bay views from this in-town Rock Hall waterfront home. The 2800+ sq.ft. home features 3-4 bedrooms, 3 bathrooms and a layout that's great for large groups or multifamily gatherings. The house has a new (2024) roof, new kitchen appliances, fresh paint and some new flooring. Outside, the large water-side yard was recently graded and seeded, and a new fishing pier was

    Cindy Genther Rock Hall Properties Real Estate

    5738 Beach Rd, Rock Hall, MD 21661
    • /15

      Est $366,071 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 4,300 Sq Ft

      21326 E Sharp St, Rock Hall, MD 21661

      21326 E Sharp St, Rock Hall, MD 21661
  • /29

    $315,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10670 Tintah Rd, Chestertown, MD 21620

    Agent Photo

    Bronwyn Scott

    Samson Properties

    (443) 767-4153

    10670 Tintah Rd, Chestertown, MD 21620
  • /13

    $150,000 Sold Aug 04, 2025

    • 800 Sq Ft
    • $188/SF
    • 26 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    21899 Lovers Ln, Rock Hall, MD 21661

    Why rent when you can own this renovated and move-in ready 2BR/1BA mobile home located minutes from the heart of Rock Hall. Enjoy peaceful living with bonus features like a covered rear porch, shed, and a wooden children's play set — perfect for relaxing or entertaining. Set on a quiet lot with easy access to marinas, the Chesapeake Bay, and everything the Eastern Shore has to offer. Ideal

    Nicole Stephens Tesla Realty Group, LLC

    21899 Lovers Ln, Rock Hall, MD 21661
    • /27

      Est $397,823 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
  • /45

    $698,000

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft

    9194 N Bayview Ave, Chestertown, MD 21620

    Stunning home and property with 180-degree views of the Chesapeake Bay.The home was completely remodeled in 2017 by Taylor Loughry Construction. Boasting a bright open floor plan with high-end finishing, vaulted ceilings with skylights, and beautifully landscaped outdoor space. Two bedrooms and two full bathrooms, open living space with a gourmet kitchen, and a large deck overlooking the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 650-6367

    9194 N Bayview Ave, Chestertown, MD 21620
  • /36

    $250,000 Sold Jul 31, 2025

    • 1,325 Sq Ft
    • $189/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    304 Hadaway Dr, Chestertown, MD 21620

    It doesn’t get any more hometown than this new offering right smack in the heart of hometown Chestertown! It’s peaceful, it’s rural and it looks like a Norman Rockwell this town. This is the Eastern Shore at its finest with plenty amenities close to town and countless activities for those sportsman who like to hunt fish and crab. That’s what we do out here and you have the Chester River right in

    Joseph Craig Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
    • /34

      Est $273,153 Not Listed For Sale

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

      7499 Poplar Ave, Chestertown, MD 21620

      7499 Poplar Ave, Chestertown, MD 21620
  • /20

    $310,000

    • 3 Beds
    • 1.5 Baths
    • 1,982 Sq Ft

    390 Hurtt Ave, Millington, MD 21651

    Welcome to this charming Federal-style home, meticulously maintained and thoughtfully updated. As you step onto the inviting front porch and through the elegant double doors, you'll find a beautifully renovated interior. The kitchen boasts cherry cabinets, granite countertops, and stainless-steel appliances. The family room addition features a cozy wood-burning fireplace and built-in shelving.

    Agent Photo

    Demetra Rice

    Rice Premier Properties LLC

    (410) 724-1166

    390 Hurtt Ave, Millington, MD 21651
  • /32

    $645,000 Sold Jul 31, 2025

    • 2,240 Sq Ft
    • $288/SF
    • 2 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1989

    7682 Waterview Ln, Chestertown, MD 21620

    Lovely colonial in Country Club Estates. The property goes back to Country Club Lane. 3 bedrooms and 3 full baths. One of the full baths is on the first floor so there is potential for a main floor bedroom. Screened-in porch overlooking the landscaped yard. 2 gas fireplaces. Open kitchen to family room. Mature landscaping. Nicely set back from the road. Well water, public sewer. Side

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7682 Waterview Ln, Chestertown, MD 21620
    • /12

      Est $504,597 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
  • /31

    $209,900

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft

    304 Hilltop Ln, Chestertown, MD 21620

    The townhouse is the second from the end and has three bedrooms and 2.5 baths. The slider door provides easy access to the patio and there is a stack washer on the main level, kitchen has the needed appliances. Located in Chestertown you can enjoy all of the amenities of this historic town, the Farmer's Market, Washington College is only a couple of minutes away, the many parks, marinas, and

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 824-5679

    304 Hilltop Ln, Chestertown, MD 21620
  • /40

    $350,000 Sold Jul 31, 2025

    • 1,416 Sq Ft
    • $247/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    113 Cedarwood Dr, Galena, MD 21635

    Welcome to this charming 3-Bedroom, 2-Bath Cape Cod home nestled in the desirable Dogwood Village community in Galena. With only one previous owner, this meticulously maintained property offers exceptional move-in ready condition and fantastic curb appeal.The main level features the first of three bedrooms, complete with a large walk-in closet and full hall bath, a cozy living room, and a

    Mrs. Brittany Fox RE/MAX Chesapeake

    113 Cedarwood Dr, Galena, MD 21635
    • /34

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 904 Sq Ft

      10967 Bottom Rd, Worton, MD 21678

      10967 Bottom Rd, Worton, MD 21678
  • /76

    $390,000

    • Studio
    • 2,762 Sq Ft

    396 Cypress St, Millington, MD 21651

    Investment Opportunity! If you are searching for an opportunity to start or relocate your business with rental potential to offset your mortgage, your search is over. Live in one area and rent out the other two!! This income producer is located in the heart of Millington at the main intersection. With its flexible zoning, the property is well-suited for a blend of commercial, retail, and

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 705-7528

    396 Cypress St, Millington, MD 21651
  • /63

    $473,000 Sold Jul 31, 2025

    • 2,112 Sq Ft
    • $224/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1920

    22652 McKinleyville Rd, Rock Hall, MD 21661

    Welcome to your private Eastern Shore escape! Nestled on 8.36 tranquil acres just outside the charming waterfront town of Rock Hall and only 20 minutes from historic Chestertown, this beautifully updated property offers a rare blend of nature, comfort, and recreation. Surrounded by abundant wildlife, this property is a haven for hunters and nature lovers alike—ideal for deer, turkey, and

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    22652 McKinleyville Rd, Rock Hall, MD 21661
    • /4

      Est $102,332 Not Listed For Sale

      5120 Eastern Neck Rd, Rock Hall, MD 21661

      5120 Eastern Neck Rd, Rock Hall, MD 21661
  • /25

    $489,000

    • 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
  • /22

    $359,000 Sold Jul 31, 2025

    • 1,978 Sq Ft
    • $181/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    10575 Hyala Ct, Chestertown, MD 21620

    Nestled in the tranquil Chesapeake Landing community. This large three bedroom, two bathroom contemporary rancher offers 1978 square feet of comfortable one-level living. This home is situated on a 0.33 acre corner lot with direct access to Worton Creek, minutes from downtown Chestertown. It has an open -concept floor plan with cathedral ceilings. Many upgrades have been done to this house

    Laura Anthony Benson & Mangold, LLC

    10575 Hyala Ct, Chestertown, MD 21620
    • /51

      Est $342,020 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 2,304 Sq Ft

      11993 Augustine Herman Hwy, Kennedyville, MD 21645

      11993 Augustine Herman Hwy, Kennedyville, MD 21645
  • /9

    $70,000

    • Land
    • 3.00 Acres
    • $23,333 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
  • /33

    $535,000 Sold Jul 31, 2025

    • 2,400 Sq Ft
    • $223/SF
    • 25 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1990

    20565 Rock Hall Ave Unit 5, Rock Hall, MD 21661

    Luxurious water view condo by the bay with high-end kitchen and baths. You'll feel pampered with the Chesapeake Bay views from every level. Exceptional view from the kitchen and dining area provides a beautiful space for entertaining. Truly a chef's gourmet kitchen, with granite countertops, a Wolf stove and Sub-Zero refrigerator. beautiful cherry floors in the kitchen. Decks on two levels- one

    Julia Hilfiker Gunther-McClary Real Estate

    20565 Rock Hall Ave Unit 5, Rock Hall, MD 21661

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