6,913

Kent, MD Homes

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  • 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
    /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
  • 200 Cannon St Unit 1A, Chestertown, MD 21620
    200 Cannon St Unit 1A, Chestertown, MD 21620
    200 Cannon St Unit 1A, Chestertown, MD 21620
    /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
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, 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
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $447,538 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft

      148 Grant Ct, Chestertown, MD 21620

      148 Grant Ct, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming 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
  • 128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, 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
  • 7682 Waterview Ln, Chestertown, MD 21620
    7682 Waterview Ln, Chestertown, MD 21620
    7682 Waterview Ln, 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
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $268,707 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, 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
  • 5117 Deep Point Dr, Chestertown, MD 21620
    5117 Deep Point Dr, Chestertown, MD 21620
    5117 Deep Point Dr, 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
  • 10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, 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
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      /27

      Est $392,499 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
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /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
  • 128 N Queen St Unit 4, Chestertown, MD 21620
    128 N Queen St Unit 4, Chestertown, MD 21620
    128 N Queen St Unit 4, 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
  • 212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    212 Central Dr, Chestertown, MD 21620
    /21

    $309,500 Sold Jul 31, 2025

    • 1,104 Sq Ft
    • $280/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1972

    212 Central Dr, Chestertown, MD 21620

    Great house with good bones. Lots of the big ticket items have already been done. Situated on an oversized lot with a fully fenced yard. Large driveway for plenty of parking. 3 bedrooms and 1 bath. Central air and heat. Newer roof. BAT septic system. The house is older and needs updating. but wait until you see the basement! Huge unfinished basement that the seller uses for storage and

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    212 Central Dr, Chestertown, MD 21620
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $369,436 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft

      213 Pine Cove Ln, Chestertown, MD 21620

      213 Pine Cove Ln, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /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
  • 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
  • 10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, 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
    • 7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, 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
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /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
  • 110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, 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
    • 724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      /63

      Est $360,462 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,311 Sq Ft

      724 Deep Landing Rd, Chestertown, MD 21620

      724 Deep Landing Rd, Chestertown, MD 21620
  • 206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    /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
  • 619 Cannon St, Chestertown, MD 21620
    619 Cannon St, Chestertown, MD 21620
    619 Cannon St, 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
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, 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
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /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
  • 310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    /18

    $205,000 Sold Jul 18, 2025

    • 1,216 Sq Ft
    • $169/SF
    • 24 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    310 Hilltop Ln, Chestertown, MD 21620

    Super clean, well-maintained and move-in ready! This charming 3-bedroom, 2.5-bath townhouse offers affordable, low-maintenance living. The main level features a bright kitchen, convenient half bath, in-unit laundry, a spacious living room, and an open dining area with sliding doors leading to a private patio and beautifully maintained common grounds. High Speed internet available. HOA covers lawn

    Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
    • 209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      /9

      Est $427,705 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      209 Blakefield Dr, Chestertown, MD 21620

      209 Blakefield Dr, Chestertown, MD 21620
  • 24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    /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
  • 420 Cannon St, Chestertown, MD 21620
    420 Cannon St, Chestertown, MD 21620
    420 Cannon St, Chestertown, MD 21620
    /39

    $350,000 Sold Jul 18, 2025

    • 1,080 Sq Ft
    • $324/SF
    • 29 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    420 Cannon St, Chestertown, MD 21620

    Fabulous location in the Chestertown Historic District with lots of room for expansion among brand new luxury homes! 420 Cannon sits on a 5,000 square foot lot that fronts on historic Cannon Street and is surrounded by the new Cannon Square development. Enjoy it in comfort now with plenty of room for new equity over time: Maybe double the house? Add a first floor bedroom suite? A garage? (As

    Beth Ostrander Doug Ashley Realtors, LLC

    420 Cannon St, Chestertown, MD 21620
    • 1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      /25

      Est $424,053 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,528 Sq Ft

      1213 Ewingtown Rd, Chestertown, MD 21620

      1213 Ewingtown Rd, Chestertown, MD 21620
  • 10670 Tintah Rd, Chestertown, MD 21620
    10670 Tintah Rd, Chestertown, MD 21620
    10670 Tintah Rd, Chestertown, MD 21620
    /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
  • 314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    /45

    $485,000 Sold Jul 18, 2025

    • 3,420 Sq Ft
    • $142/SF
    • 79 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2010

    314 Devon Dr, Chestertown, MD 21620

    Welcome to 314 Devon Drive in Chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets style in every room. From the moment you step into the grand foyer, you’ll feel the openness and care that’s gone into every detail.The heart of the home is the spacious kitchen, featuring a large island that’s perfect for prepping meals, gathering with friends, or simply enjoying

    Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $422,507 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,656 Sq Ft

      200 Ashley Ln, Chestertown, MD 21620

      200 Ashley Ln, Chestertown, MD 21620
  • 9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview 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
  • 211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    /52

    $795,000 Sold Jul 14, 2025

    • 4,401 Sq Ft
    • $181/SF
    • 2 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1963

    211 David Dr, Chestertown, MD 21620

    Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
    • 218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      /44

      Est $520,289 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,932 Sq Ft

      218 Camelot Dr, Chestertown, MD 21620

      218 Camelot Dr, Chestertown, MD 21620
  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, 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
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $410,000 Sold Jul 08, 2025

    • 1,656 Sq Ft
    • $248/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1916

    222 Mount Vernon Ave, Chestertown, MD 21620

    Lovingly maintained, this charming home in Chestertown’s Historic District seamlessly blends classic character with modern comfort. Restored windows, original yellow heart pine floors, and cypress siding reflect its rich history, while newer appliances, a high-efficiency boiler, tankless on-demand hot water, 3-zone heating, and leaf filter system provide everyday ease. The third floor offers

    Casey Scattergood Cross Street Realtors LLC

    222 Mount Vernon Ave, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County Chestertown

Real Estate & Homes

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 48 days on the market compared to the national average of 70 days. The median sale price for homes in Chestertown, MD over the last 12 months is $495,000, up 82% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$495,000
Median Single Family Sale Price
$495,000
Median Townhouse Sale Price
$569,990
Median 2 Bedroom Sale Price
$565,000
Average Price Per Sq Ft
$303
Number of Homes for Sale
5
Last 12 months Home Sales
57
Months of Supply
1.10
Median List Price
$495,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
82%
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