6,895

Chestertown, MD Homes

Section Image Section Image
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $438,615 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
  • 726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    /35

    $484,990 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft

    726 Aldora Dr, Chestertown, MD 21620

    2 DECORATED MODEL OPEN The Sophie is a luxury 3 Bedroom Villa with a layout that is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower and an additional

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (443) 429-1073

    726 Aldora Dr, Chestertown, MD 21620
  • 5594 Langford Bay Rd, Chestertown, MD 21620
    5594 Langford Bay Rd, Chestertown, MD 21620
    5594 Langford Bay Rd, Chestertown, MD 21620
    /40

    $750,000 Sold May 22, 2025

    • 1,682 Sq Ft
    • $446/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1956

    5594 Langford Bay Rd, Chestertown, MD 21620

    Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether you're searching for a quiet second home getaway or a prime income-producing investment, this property offers the waterfront lifestyle so many dream about—boating, fishing, and relaxing right from your own private dock.The heart

    Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, Chestertown, MD 21620
    • 218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      /44

      Est $527,695 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
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $512,340 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury 4 Bedroom Villa. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower and

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    1106 Round Top Rd, Chestertown, MD 21620
    /27

    $250,000 Sold May 22, 2025

    • 1,248 Sq Ft
    • $200/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    1106 Round Top Rd, Chestertown, MD 21620

    Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in the peaceful surroundings. The home features an unfinished basement, offering potential for extra storage or future living space. With some vision and TLC, this property could shine—whether you're looking to renovate or start

    Clint Evans Cross Street Realtors LLC

    1106 Round Top Rd, Chestertown, MD 21620
    • 209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      209 Landing Ln, Chestertown, MD 21620
      /33

      Est $684,120 Not Listed For Sale

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

      209 Landing Ln, Chestertown, MD 21620

      209 Landing Ln, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    /22

    $490,000 Sold May 21, 2025

    • 1,476 Sq Ft
    • $332/SF
    • 14 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1900

    101 S Mill St, Chestertown, MD 21620

    Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
    • 108 Harlan Loop, Chestertown, MD 21620
      108 Harlan Loop, Chestertown, MD 21620
      108 Harlan Loop, Chestertown, MD 21620
      /73

      Est $541,271 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,692 Sq Ft

      108 Harlan Loop, Chestertown, MD 21620

      108 Harlan Loop, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /22

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • 108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    /40

    $600,000 Sold May 16, 2025

    • 2,536 Sq Ft
    • $237/SF
    • 5 Beds
    • 2.5 Baths
    • Built 1920

    108 N Queen St, Chestertown, MD 21620

    Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
    • 141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      141 Round Top Creek Ln, Chestertown, MD 21620
      /18

      Est $1,368,317 Not Listed For Sale

      • Studio

      141 Round Top Creek Ln, Chestertown, MD 21620

      141 Round Top Creek Ln, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $759,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3.5 Baths

    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

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • 308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    /32

    $782,500 Sold May 09, 2025

    • 2,204 Sq Ft
    • $355/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    308 Landing Ln, Chestertown, MD 21620

    Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale. The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for

    John Burke Gunther-McClary Real Estate

    308 Landing Ln, Chestertown, MD 21620
    • 204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      204 N Mill St, Chestertown, MD 21620
      /44

      Est $434,380 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft

      204 N Mill St, Chestertown, MD 21620

      204 N Mill St, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /23

    $898,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620
  • 8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    /51

    $370,000 Sold May 08, 2025

    • 1,296 Sq Ft
    • $285/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1968

    8605 Camp Rd, Chestertown, MD 21620

    Your home sweet home retreat - a gorgeous 3 Bedroom 2 Full Bathroom Rancher with attached carport and unfinished basement is available to tour! Major renovations in 2020 and maintained to pristine condition. If you are looking for a place to come home and relax - this is the one! Sit on the front porch and enjoy the afternoon sun, calm surroundings or listen to the birds actively chirping. Head

    Crystal Smith RE/MAX Executive

    8605 Camp Rd, Chestertown, MD 21620
    • 101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      /23

      Est $392,927 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft

      101 S Kent St, Chestertown, MD 21620

      101 S Kent St, Chestertown, MD 21620
  • 730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    /34

    $492,464 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    730 Aldora Dr Unit 114, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury 4 Bedroom Villa. The layout is welcoming and very functional. Featuring a huge family room with gas fireplace, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 431-1757

    730 Aldora Dr Unit 114, Chestertown, MD 21620
  • 202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    /37

    $290,000 Sold May 08, 2025

    • 1,252 Sq Ft
    • $232/SF
    • 104 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1966

    202 Glen St, Chestertown, MD 21620

    Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.

    Debbie Meikle Doug Ashley Realtors, LLC

    202 Glen St, Chestertown, MD 21620
    • 116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      /54

      Est $612,950 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,110 Sq Ft

      116 N Queen St, Chestertown, MD 21620

      116 N Queen St, Chestertown, MD 21620
  • 811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    811 S Meadowview Dr, Chestertown, MD 21620
    /45

    $459,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft

    811 S Meadowview Dr, Chestertown, MD 21620

    Charming and Immaculately Maintained One-Level HomeStep onto the inviting front porch of this meticulously cared-for home, where every detail shines both inside and out. Featuring a thoughtful and spacious floor plan, this home offers a primary suite at one end and two additional bedrooms with a full bath at the opposite end for added privacy. In the heart of the home, you'll find a cozy living

    Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
  • 116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    /38

    $289,500 Sold May 05, 2025

    • 1,867 Sq Ft
    • $155/SF
    • 13 Days On Market
    • 2 Beds
    • 4 Baths
    • Built 2004

    116 Oak Leaf Dr, Chestertown, MD 21620

    Charming & Move-In ReadyDiscover this beautifully maintained end-unit townhome just minutes from downtown Chestertown! This home has been loved and cared for by the original owners. Offering updated hardwood flooring, carpeting on stairs, fresh paint in the primary living space, a new roof, this ensuring peace of mind for years to come.The spacious master suite features vaulted ceilings, a stall

    Grace Crockett Doug Ashley Realtors, LLC

    116 Oak Leaf Dr, Chestertown, MD 21620
    • 107 Adela Way, Chestertown, MD 21620
      107 Adela Way, Chestertown, MD 21620
      107 Adela Way, Chestertown, MD 21620
      /31

      Est $488,109 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft

      107 Adela Way, Chestertown, MD 21620

      107 Adela Way, Chestertown, MD 21620
  • 22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    /73

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    22570 Bay Shore Rd, Chestertown, MD 21620

    Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen /

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
  • 118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    /34

    $265,000 Sold May 02, 2025

    • 1,114 Sq Ft
    • $238/SF
    • 120 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    118 Char Nor Manor Blvd, Chestertown, MD 21620

    An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your

    Rylie Patrick Chesapeake Real Estate Associates, LLC

    118 Char Nor Manor Blvd, Chestertown, MD 21620
    • 105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      /43

      Est $413,452 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      105 Sutton Way, Chestertown, MD 21620

      105 Sutton Way, Chestertown, MD 21620
  • 114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    /36

    $419,000 Open Sat 10:30AM - 12:30PM

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft

    114 Ryan Ct, Chestertown, MD 21620

    Priced over $50,000 below recent appraised value! Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stone’s throw from historic

    Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
  • 107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    /19

    $230,000 Sold May 01, 2025

    • 1,140 Sq Ft
    • $202/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2022

    107 Chester Arms Dr, Chestertown, MD 21620

    Why rent when you can own for less?!?! Three beds, 2 baths!! This inviting one-level home offers easy one-level living. Featuring luxury vinyl plank flooring , a stylish open kitchen and granite countertops, and a cozy eat-in area that opens to the living room, this home feels very welcoming. The comfortable primary suite features a full bath, while two additional bedrooms provide flexibility

    Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, Chestertown, MD 21620
    • 331 Devon Dr, Chestertown, MD 21620
      331 Devon Dr, Chestertown, MD 21620
      331 Devon Dr, Chestertown, MD 21620
      /48

      Est $518,304 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,834 Sq Ft

      331 Devon Dr, Chestertown, MD 21620

      331 Devon Dr, Chestertown, MD 21620
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    /48

    $559,900

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    $20,000 Price Reduction!A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • 123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    /53

    $485,000 Sold May 01, 2025

    • 1,648 Sq Ft
    • $294/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1918

    123 Burchard Sawmill Rd, Chestertown, MD 21620

    This is it! This is the one you and your horse have been dreaming about! Absolutely darling 4+ acre farmette! Charm charm charm plus function function function. Turnkey and ready for your horses, your ponies or your 4-H projects, or all of the above! Built in 1918, this 3 Bedroom American Folk merges vernacular farmhouse (winder staircase, built-in corner cupboard, beautiful curved plaster wall)

    Crystal Pickett EXP Realty, LLC

    123 Burchard Sawmill Rd, Chestertown, MD 21620
    • 335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      /44

      Est $519,385 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,874 Sq Ft

      335 Devon Dr, Chestertown, MD 21620

      335 Devon Dr, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $425,000

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from the family’s

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    /23

    $352,500 Sold Apr 30, 2025

    • 1,402 Sq Ft
    • $251/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    505 N Kent St, Chestertown, MD 21620

    Charming Rancher in Sought-After Byford Development!Nestled in the desirable Byford Development of Chestertown, this 1,402 sq. ft. rancher sits on a spacious 1/3-acre lot offering comfort, convenience, and opportunity! Featuring 3 bedrooms and 2 full baths, this one-level home boasts a primary suite with double sinks and an oversized shower, as well as a bright enclosed Florida room with vaulted

    Sarah Ulrick Rock Hall Properties Real Estate

    505 N Kent St, Chestertown, MD 21620
    • 106 Camelot Dr, Chestertown, MD 21620
      106 Camelot Dr, Chestertown, MD 21620
      106 Camelot Dr, Chestertown, MD 21620
      /55

      Est $542,336 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,760 Sq Ft

      106 Camelot Dr, Chestertown, MD 21620

      106 Camelot Dr, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /52

    $845,000

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft

    24576 Langford Rd, Chestertown, MD 21620

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

    Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
  • 113 Pine Cove Ln, Chestertown, MD 21620
    113 Pine Cove Ln, Chestertown, MD 21620
    /2

    $57,500 Sold Apr 30, 2025

    • Land
    • 0.45 Acre
    • $127,778 per Acre
    • 185 Days On Market

    113 Pine Cove Ln, Chestertown, MD 21620

    Wonderful opportunity to purchase two established adjoining residential lots within a short walking distance to the Chester River and deep water boat ramp. These two recorded lots were purchased many years ago by a family that vacationed in a home nearby. These lots have not been perc tested but the soil types are conducive to percing and there are homes on the neighboring parcels. Please

    William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • 112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      /18

      Not Listed For Sale

      112 Pine Tree Rd, Chestertown, MD 21620

      112 Pine Tree Rd, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 18

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