12,094

Kent County, MD Homes

Section Image Section Image
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /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
  • 5785 Downey Ave, Rock Hall, MD 21661
    5785 Downey Ave, Rock Hall, MD 21661
    5785 Downey Ave, Rock Hall, MD 21661
    /9

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    5785 Downey Ave, Rock Hall, MD 21661

    Property Id: 1632359This 2 bedroom 1 bath home is all 1 level living on a quiet dead end street. Walking distance to shops & restaurants in the heart of Rock Hall. Propane cooking and on demand hot water, so you never run out. If interested, call Chris with Kendall Properties to schedule a showing at . Credit check must be at least 600 and background check fairly clean.

    5785 Downey Ave, Rock Hall, MD 21661
  • 10740 Worton Rd, Worton, MD 21678
    10740 Worton Rd, Worton, MD 21678
    10740 Worton Rd, Worton, MD 21678
    /52

    $355,000 Sold Dec 09, 2025

    • 2,988 Sq Ft
    • $119/SF
    • 58 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1920

    10740 Worton Rd, Worton, MD 21678

    This home was formerly the old Worton Elementary schoolhouse and still retains some of the original features, such as tin ceilings in the living room. The main level has a spacious living room with wood floors, huge kitchen with wood stove, a main level bedroom with a sitting room and full bath with a walk-in shower, and additional hall bath with laundry, several additional rooms and 2 screened

    Doug Ashley Doug Ashley Realtors, LLC

    10740 Worton Rd, Worton, MD 21678
    • 7 Horning Dr, Betterton, MD 21610
      7 Horning Dr, Betterton, MD 21610
      7 Horning Dr, Betterton, MD 21610
      /46

      Est $176,351 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 628 Sq Ft

      7 Horning Dr, Betterton, MD 21610

      7 Horning Dr, Betterton, MD 21610
  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, 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
  • 300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    /27

    $2,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Townhouse for Rent

    300 Hilltop Ln, Chestertown, MD 21620

    ***Must have first month, security deposit and a 620+ credit score. 5 grace period days. 5% late fee. Renter's insurance required.***This thoughtfully renovated end-unit townhouse offers 3 bedrooms, 2.5 bathrooms. The kitchen features freshly painted cabinets and brand-new appliances, complemented by new flooring throughout the home for a clean, modern feel. Step outback to your private patio

    Jordan Larigan VYBE Realty

    300 Hilltop Ln, Chestertown, MD 21620
  • 22783 McKinleyville Rd, Rock Hall, MD 21661
    22783 McKinleyville Rd, Rock Hall, MD 21661
    22783 McKinleyville Rd, Rock Hall, MD 21661
    /15

    $170,000 Sold Dec 08, 2025

    • 1,028 Sq Ft
    • $165/SF
    • 72 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1902

    22783 McKinleyville Rd, Rock Hall, MD 21661

    Classic farm house on half an acre, just a stones throw from the Rock Hall Yacht Club and Langford Bay Marina. The main home has two full bathrooms and two bedrooms. The large screened-in porch overlooks the spacious yard. A nice spot to catch a breeze from the water. Additionally there is guesthouse with a full bath and kitchen. There are two small storage sheds on the property. The houses have

    Julia Hilfiker Gunther-McClary Real Estate

    22783 McKinleyville Rd, Rock Hall, MD 21661
    • 14182 N 1st Ave, Kennedyville, MD 21645
      14182 N 1st Ave, Kennedyville, MD 21645
      14182 N 1st Ave, Kennedyville, MD 21645
      /54

      Est $557,379 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,784 Sq Ft

      14182 N 1st Ave, Kennedyville, MD 21645

      14182 N 1st Ave, Kennedyville, MD 21645
  • 206 Virginia Ave, Galena, MD 21635
    206 Virginia Ave, Galena, MD 21635
    206 Virginia Ave, Galena, MD 21635
    /31

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,406 Sq Ft

    206 Virginia Ave, Galena, MD 21635

    Are you looking for a classic home with a ton of charm? Do you love original wood floors? Not afraid of some updating? This could just be the home for you! Screened in porch welcomes you to a beautiful foyer, and a classic living room with a fireplace that has been closed up but still provides a nice focal point. Owner is not sure if it could become a working wood-burning fireplace or not, but a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (667) 843-7243

    206 Virginia Ave, Galena, MD 21635
  • 319 Holly Ct, Chestertown, MD 21620
    319 Holly Ct, Chestertown, MD 21620
    319 Holly Ct, Chestertown, MD 21620
    /10

    $1,700 per month

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft
    • House for Rent

    319 Holly Ct, Chestertown, MD 21620

    Property Id: 2236431This lovely 2 bedroom 1 bath home is nestled in a quit neighborhood in Centreville Md. It features a great yard, on demand hot water heater, & a large detached garage. Close to shopping and restaurants. If interested, call or text Chris with Kendall Properties LLC for more information. . Credit and background checks will be done.

    319 Holly Ct, Chestertown, MD 21620
  • 7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    /26

    $287,500 Sold Dec 05, 2025

    • 1,232 Sq Ft
    • $233/SF
    • 35 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    7483 Shortall St, Chestertown, MD 21620

    **SELLERS HAVE FOUND PROPERTY OF CHOICE; BRING YOUR BEST OFFER!**Welcome to this inviting, move-in-ready rancher tucked away in a tranquil Chestertown setting. Offering three bedrooms and two full baths, the home showcases fresh paint, new flooring, sleek stainless steel appliances, and stunning Beechwood butcher block countertops. Natural light pours in through the Anderson windows, filling the

    Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
    • 24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      /24

      Est $369,836 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      24291 Chestertown Rd, Chestertown, MD 21620

      24291 Chestertown Rd, Chestertown, MD 21620
  • 24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    /34

    $799,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    24204 Drayton Landing Dr, Worton, MD 21678

    Welcome to 24204 Drayton Landing Drive — a beautifully renovated 3-bedroom, 2-bath home set on 2 peaceful acres in the heart of Kent County on Maryland’s Eastern Shore.Nestled within the desirable Kinnairds Point community, residents enjoy a warm neighborhood setting along with exclusive access to two waterfront common areas: a boat launch and a swim beach. These shared spaces provide the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 594-6295

    24204 Drayton Landing Dr, Worton, MD 21678
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec 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
  • 26994 Branchtown Rd, Worton, MD 21678
    26994 Branchtown Rd, Worton, MD 21678
    26994 Branchtown Rd, Worton, MD 21678
    /24

    $349,900 Sold Dec 05, 2025

    • 1,440 Sq Ft
    • $243/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2025

    26994 Branchtown Rd, Worton, MD 21678

    Quality built and adorable Cape Cod on Private 1 acre mostly wooded lot. 4 bedrooms, 2 full bathrooms. Stainless steel appliances, 2X6 walls, high efficiency heat pump and central a/c system. Nice deck (10'x14') overlooking peaceful back yard and woods. Extra insulated storage in knee walls thru upstairs bedrooms. Close to Rt 213 and Chestertown. No HOA. Owner agent.

    Jason Dey Kevin Dey Realty

    26994 Branchtown Rd, Worton, MD 21678
    • 32739 Hunt Ln, Galena, MD 21635
      32739 Hunt Ln, Galena, MD 21635
      32739 Hunt Ln, Galena, MD 21635
      /86

      Est $980,908 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,777 Sq Ft

      32739 Hunt Ln, Galena, MD 21635

      32739 Hunt Ln, Galena, MD 21635
  • 11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    /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
  • 118 N Water St, Chestertown, MD 21620
    118 N Water St, Chestertown, MD 21620
    /2

    $1,400 per month

    • 2 Beds
    • 1 Bath
    • House for Rent

    118 N Water St, Chestertown, MD 21620

    Property Id: 1401647This water view apartment has 2 bedroom 1 bath with HVAC on the 2nd floor. Walking distance to downtown restaurants, groceries and shopping. If interested, call or text Chris @ Kendall Properties LLC at for a showing. Credit score must be at least 600 and background check fairly clean.

    118 N Water St, Chestertown, MD 21620
  • 101 Metcalfe Rd, Chestertown, MD 21620
    101 Metcalfe Rd, Chestertown, MD 21620
    101 Metcalfe Rd, Chestertown, MD 21620
    /26

    $264,900 Sold Dec 05, 2025

    • 1,280 Sq Ft
    • $207/SF
    • 2 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 2025

    101 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    101 Metcalfe Rd, Chestertown, MD 21620
    • 11500 Lynch Rd, Worton, MD 21678
      11500 Lynch Rd, Worton, MD 21678
      11500 Lynch Rd, Worton, MD 21678
      /41

      Est $202,852 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 2,318 Sq Ft

      11500 Lynch Rd, Worton, MD 21678

      11500 Lynch Rd, Worton, MD 21678
  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /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
  • 13951 Augustine Herman Hwy, Galena, MD 21635
    13951 Augustine Herman Hwy, Galena, MD 21635
    13951 Augustine Herman Hwy, Galena, MD 21635
    /11

    $2,450 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    13951 Augustine Herman Hwy, Galena, MD 21635

    Property Id: 2260722This beautiful 3 bedroom 2 bath home with an unfinished basement was built in 1970 and has been thoughtfully upgraded and comes fully furnished, you wont need a thing! All new appliances, new HVAC, and new furniture. This home has stunning outdoor lighting. This move in ready home is also close to shopping, restaurants and marinas. 1 small dog is allowed. Credit and

    13951 Augustine Herman Hwy, Galena, MD 21635
  • 8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    /47

    $700,000 Sold Dec 04, 2025

    • 3,735 Sq Ft
    • $187/SF
    • 2 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2014

    8951 Orchard Dr, Chestertown, MD 21620

    Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout. The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water

    Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • 111 Cedarwood Dr, Galena, MD 21635
      111 Cedarwood Dr, Galena, MD 21635
      111 Cedarwood Dr, Galena, MD 21635
      /38

      Est $359,793 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,276 Sq Ft

      111 Cedarwood Dr, Galena, MD 21635

      111 Cedarwood Dr, Galena, MD 21635
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /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
  • 7121 Quaker Neck Rd, Chestertown, MD 21620
    7121 Quaker Neck Rd, Chestertown, MD 21620
    7121 Quaker Neck Rd, Chestertown, MD 21620
    /10

    $2,000 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    7121 Quaker Neck Rd, Chestertown, MD 21620

    This is a perfect little house in the country on a 1 acre secluded lot 1 1/2 miles from Chestertown. It is brand new on the inside with high end finishes. New Anderson windows, new doors, tile and laminate floors, SS appliances, granite countertops, Rinnai hot water heater, mini split heat pump, Owner will cut grass and maintain exterior ( 2 tomato plants) for one year, high speed internet

    7121 Quaker Neck Rd, Chestertown, MD 21620
  • 10444 Worton Rd, Worton, MD 21678
    10444 Worton Rd, Worton, MD 21678
    10444 Worton Rd, Worton, MD 21678
    /25

    $320,000 Sold Dec 04, 2025

    • 1,120 Sq Ft
    • $286/SF
    • 37 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1985

    10444 Worton Rd, Worton, MD 21678

    Nestled in the serene countryside of Worton, Maryland, this charming 3 bed, 1 bath home offers the perfect balance of seclusion and convenience. Sitting on nearly half an acre, the property provides ample outdoor space, ideal for entertaining guests or simply relaxing in peace.Inside, you’ll find three cozy bedrooms and a full bathroom, while a large garage adds significant storage (or

    Natasha Lasek AB & Co Realtors, Inc.

    10444 Worton Rd, Worton, MD 21678
    • 23055 Parsons Rd, Chestertown, MD 21620
      23055 Parsons Rd, Chestertown, MD 21620
      23055 Parsons Rd, Chestertown, MD 21620
      /33

      Est $340,184 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,473 Sq Ft

      23055 Parsons Rd, Chestertown, MD 21620

      23055 Parsons Rd, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /9

    $1,150,000 Pending

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 419-7633

    206 Cannon St, Chestertown, MD 21620
  • 12776 Still Pond Rd, Still Pond, MD 21667
    12776 Still Pond Rd, Still Pond, MD 21667
    12776 Still Pond Rd, Still Pond, MD 21667
    /68

    $309,000 Sold Dec 02, 2025

    • 1,735 Sq Ft
    • $178/SF
    • 171 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1915

    12776 Still Pond Rd, Still Pond, MD 21667

    Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views and

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    12776 Still Pond Rd, Still Pond, MD 21667
    • 305 Lincoln Dr, Chestertown, MD 21620
      305 Lincoln Dr, Chestertown, MD 21620
      305 Lincoln Dr, Chestertown, MD 21620
      /33

      Est $272,911 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,632 Sq Ft

      305 Lincoln Dr, Chestertown, MD 21620

      305 Lincoln Dr, Chestertown, MD 21620
  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /2

    $475,000 Open House 1/03

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Discover an incredible opportunity in the highly sought-after Coventry Farms community—one of the rare chances to get into this neighborhood for under $500K. This inviting Colonial offers the perfect blend of comfort, charm, and value, with plenty of room to make it your own and build equity over time. Step inside to a warm and welcoming layout featuring thoughtfully designed accent walls, a

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $375,000 Sold Dec 01, 2025

    • 1,842 Sq Ft
    • $204/SF
    • 83 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2002

    907 N Meadowview Dr, Chestertown, MD 21620

    JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space. Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 25270 Swamp Rd, Worton, MD 21678
      25270 Swamp Rd, Worton, MD 21678
      25270 Swamp Rd, Worton, MD 21678
      /31

      Est $293,637 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,048 Sq Ft

      25270 Swamp Rd, Worton, MD 21678

      25270 Swamp Rd, Worton, MD 21678
  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 0.09 Acre
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • 119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    /60

    $1,165,000 Sold Dec 01, 2025

    • 4,409 Sq Ft
    • $264/SF
    • 5 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1876

    119 High St, Chestertown, MD 21620

    From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of

    Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
    • 11325 Station Rd, Worton, MD 21678
      11325 Station Rd, Worton, MD 21678
      11325 Station Rd, Worton, MD 21678
      /42

      Est $395,699 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,408 Sq Ft

      11325 Station Rd, Worton, MD 21678

      11325 Station Rd, Worton, MD 21678
  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $770,000

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft

    7844 Chester Ct, Chestertown, MD 21620

    Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $750,000 Sold Dec 01, 2025

    • 238 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2024

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize

    John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
    • 4742 Huntingfield Rd, Rock Hall, MD 21661
      4742 Huntingfield Rd, Rock Hall, MD 21661
      4742 Huntingfield Rd, Rock Hall, MD 21661
      /42

      Est $1,899,880 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,625 Sq Ft

      4742 Huntingfield Rd, Rock Hall, MD 21661

      4742 Huntingfield Rd, Rock Hall, MD 21661

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group