12,149

Kent, MD Homes

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  • /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
  • /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
  • /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
    • /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
  • /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
  • /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
  • /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
    • /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
  • /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
  • /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
  • /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
    • /4

      Est $82,765 Not Listed For Sale

      32072 Shorewood Rd, Galena, MD 21635

      32072 Shorewood Rd, Galena, MD 21635
  • /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
  • /36

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • House for Rent

    6339 Quaker Neck Rd, Chestertown, MD 21620

    Beautiful cape in a peaceful setting. 3 bed and 2 baths. Updated kitchen. Fireplace with built in book shelves in the living room. Lovely screened in porch overlooking the private back yard. Credit score of at least 700 required. No pets. No smoking.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    6339 Quaker Neck Rd, Chestertown, MD 21620
  • /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
    • /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
  • /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
  • /25

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    5117 Deep Point Dr, Chestertown, MD 21620

    Welcome home to historic Overbeck! This beautiful old home overlooks an expansive yard and on to the Chester River. The small beach is a perfect launch site for your paddle boards and kayaks. Inside find fireplaces, hardwood floors on main level along with brick floored sunroom. Great big fireplace in Kitchen then up a few stairs to formal dining room . Cozy living room with covered porch on

    Julie Cary Rosendale Realty

    5117 Deep Point Dr, Chestertown, MD 21620
  • /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
    • /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
  • /63

    $1,550,000

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • /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
  • /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
    • /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
  • /41

    $569,000

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

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, 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
  • /34

    $550,000 Sold Jul 31, 2025

    • 1,649 Sq Ft
    • $334/SF
    • 127 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2014

    21026 Rock Hall Ave, Rock Hall, MD 21661

    Lush gardens frame the entrance to this waterview coastal contemporary home in the heart of Rock Hall. Wide stairs lead to a covered front porch that's just perfect for sipping sweet tea and enjoying your own private oasis. Enter the foyer and leave your troubles (and dirty shoes) here. Up a short set of lighted stairs is a hallway that leads to a 23' x 27' open floorplan living/dining/kitchen

    Cindy Genther Rock Hall Properties Real Estate

    21026 Rock Hall Ave, Rock Hall, MD 21661
    • /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
  • /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • /73

    $380,000 Sold Jul 30, 2025

    • 2,106 Sq Ft
    • $180/SF
    • 11 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1988

    10705 Millbrook Dr, Chestertown, MD 21620

    Nestled in the water-access community of Chesapeake Landing, this charming Cape Cod-style home offers a perfect blend of classic character and modern comfort. With over 2,100 square feet of finished living space, the home features four spacious bedrooms and three full bathrooms, ideal for flexible living arrangements. Inside, you’ll find a freshly painted bright and open layout with beautiful

    Adam Murphy RE/MAX Realty Centre, Inc.

    10705 Millbrook Dr, Chestertown, MD 21620
    • /34

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 904 Sq Ft

      10967 Bottom Rd, Worton, MD 21678

      10967 Bottom Rd, Worton, MD 21678
  • /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 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
  • /22

    $175,000 Sold Jul 25, 2025

    • 896 Sq Ft
    • $195/SF
    • 85 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    110 Philosophers Terrace, Chestertown, MD 21620

    Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

    Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
    • /4

      Est $102,332 Not Listed For Sale

      5120 Eastern Neck Rd, Rock Hall, MD 21661

      5120 Eastern Neck Rd, Rock Hall, MD 21661
  • /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • /28

    $362,500 Sold Jul 22, 2025

    • 1,600 Sq Ft
    • $227/SF
    • 41 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1989

    1 A Bayview Rd Unit 7A, Betterton, MD 21610

    Welcome to Rigbie Bluff Condominium! This is a rare opportunity for an end unit 2-bedroom condo to be available which offers breathtaking panoramic views of the Upper Chesapeake Bay and spectacular sunsets in the spring & summer. Enjoy waterfront living at its finest with your own boat slip, perfect for boating enthusiasts.Relax by the community pool, take advantage of private beach access,

    Ashton Kelley Gunther-McClary Real Estate

    1 A Bayview Rd Unit 7A, Betterton, MD 21610
    • /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
  • /36

    $375,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 2,302 Sq Ft

    206 Silver Heel Dr, Chestertown, MD 21620

    Welcome to The Verona in The Village at Chestertown—a beautifully designed, move-in ready home offering 2,302 square feet of flexible living space across three levels. With 5 bedrooms and 3.5 bathrooms, this home perfectly balances comfort, function, and style. Step inside to a welcoming foyer that leads into a spacious family room, ideal for relaxing or entertaining. The open-concept layout

    Agent Photo

    TJ Bennett

    Samson Properties

    (410) 567-0695

    206 Silver Heel Dr, Chestertown, MD 21620
  • /9

    $190,500 Sold Jul 22, 2025

    • 882 Sq Ft
    • $216/SF
    • 50 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    619 Cannon St, Chestertown, MD 21620

    Buyer Financing fell through, so their loss is your gain! Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect

    Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
    • /56

      Est $401,237 Not Listed For Sale

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

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620

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