7,060

Homes in ZIP Code 21620

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  • 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
  • 7452 Poplar Ave, Chestertown, MD 21620
    7452 Poplar Ave, Chestertown, MD 21620
    7452 Poplar Ave, Chestertown, MD 21620
    /9

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 842 Sq Ft
    • House for Rent

    7452 Poplar Ave, Chestertown, MD 21620

    Fully Remodeled 3BR/1BA Home on Half Acre+ Lot!This beautifully updated home features brand new flooring, appliances, plumbing, electric, and new drywall/ fresh paint.Enjoy energy efficiency with new insulation throughout. Rent includes sewer and water system annual maintenance. Requirements: Income: $5,000+/month, Credit: 580+, small dogs considered case by caseMove-in ready and

    7452 Poplar Ave, 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
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $458,148 Not Listed For Sale

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

      148 Grant Ct, Chestertown, MD 21620

      148 Grant Ct, 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
  • 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
  • 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
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, 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
  • 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
  • 6339 Quaker Neck Rd, Chestertown, MD 21620
    6339 Quaker Neck Rd, Chestertown, MD 21620
    6339 Quaker Neck Rd, Chestertown, MD 21620
    /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
  • 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
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, 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
  • 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
  • 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
  • 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
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $362,046 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
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, 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
  • 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
    • 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
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    /5

    $149,900

    • Land
    • 10 Acres
    • $14,915 per Acre

    0 Hoffecker Rd, Chestertown, MD 21620

    Serene 10-acre wooded lot on Hoffecker Rd. A short distance to the Deep Landing boat launch and historic Chestertown. This parcel offers the perfect balance of seclusion and convenience, surrounded by farmland, beautiful trees, and a short distance to the Chester River. Tons of potential to become a family retreat or private future home.Perc test completed.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 216-1306

    0 Hoffecker Rd, 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
  • 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
    • 724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      /63

      Est $369,837 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
  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,297,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    300 Hickory Ln, Chestertown, MD 21620

    Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious ranch-style

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-6289

    300 Hickory 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
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $385,029 Not Listed For Sale

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

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • 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

    $80,000

    • Land
    • 3.00 Acres
    • $26,667 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
  • 10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    /5

    $285,000 Sold Jul 08, 2025

    • 2,142 Sq Ft
    • $133/SF
    • 8 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    10141 Flatland Rd, Chestertown, MD 21620

    Farmhouse located on two acre cleared lot that overlooks farmland. Improvements have been made to the property, including a metal farm/garage/workshop building with electric and three garage doors. There is a shed that improvements have started on, but not complete. Property has two bedrooms and one bath, with a traditional floor plan typical for a farmhouse style home. The kitchen is in

    Retha Arrabal Doug Ashley Realtors, LLC

    10141 Flatland Rd, 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
  • 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
  • 25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    /39

    $550,000 Sold Jul 01, 2025

    • 2,010 Sq Ft
    • $274/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1992

    25285 Foxchase Dr, Chestertown, MD 21620

    Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
    • 1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      /25

      Est $428,533 Not Listed For Sale

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

      1213 Ewingtown Rd, Chestertown, MD 21620

      1213 Ewingtown 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
  • 7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    7988 Aldan Dr, Chestertown, MD 21620
    /56

    $759,000 Sold Jul 01, 2025

    • 3,394 Sq Ft
    • $224/SF
    • 2 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2000

    7988 Aldan Dr, Chestertown, MD 21620

    This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor

    Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $438,816 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
  • 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
  • 898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    /34

    $237,000 Sold Jun 30, 2025

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

    898 Washington Ave, Chestertown, MD 21620

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

    Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
    • 218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      /44

      Est $519,560 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
  • 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

Showing Results 1 - 40, Page 1 of 18

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