6,883

Chestertown, MD Homes

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    • /22

      Est $206,918 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      614 High St, Chestertown, MD 21620

      614 High St, Chestertown, MD 21620
  • /44

    $365,000 Sold Jul 01, 2024

    • 2,045 Sq Ft
    • $178/SF
    • 16 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1976

    208 Byford Dr, Chestertown, MD 21620

    Lovely Cape Cod in desirable Byford Heights. First-floor Primary Bedroom and Bathroom. 2 large bedrooms with full Bathroom on 2nd floor. Beautiful Hardwood floors. Easy flowing floor plan guides you from bright living room to the dining room and then the kitchen. The Kitchen has lots of quality cabinets and space for a kitchen table. The kitchen overlooks the Family Room with Fireplace for cozy

    Mary Fielding Coldwell Banker Chesapeake Real Estate Company

    208 Byford Dr, Chestertown, MD 21620
    • /14

      Est $381,513 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,722 Sq Ft

      203 Pine St, Chestertown, MD 21620

      203 Pine St, Chestertown, MD 21620
  • /27

    $320,000 Sold Jul 01, 2024

    • 1,560 Sq Ft
    • $205/SF
    • 20 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    310 Longfellow Dr, Chestertown, MD 21620

    Look no more. This home is cute as a button and packs a ton of recent upgrades. . Starting from the top down: New roof, updated heating, hot water heater, wood flooring, kitchen counters, primary bathroom, encapsulated crawl space. This home is move in ready and has so much to offer. Great floor plan, covered front porch, fenced rear yard ready for pets, gardens, fire pits. The home

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    310 Longfellow Dr, Chestertown, MD 21620
    • /21

      Est $197,996 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      612 High St, Chestertown, MD 21620

      612 High St, Chestertown, MD 21620
  • /22

    $435,000 Sold Jun 28, 2024

    • 2,464 Sq Ft
    • $177/SF
    • 0 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1991

    807 S Meadowview Dr, Chestertown, MD 21620

    Still scheduling showings and would entertain backup offers! Please come and see the home & property! -- This IMPECCABLY maintained home has SO much to offer... main level living, family room, formal living room, home office, FOUR bedrooms, two and a half baths, a HUGE primary suite with a walk-in closet and tiled shower, partial walkout basement, massive back deck with tons of room for a crab

    Liddy Campbell TTR Sotheby's International Realty

    807 S Meadowview Dr, Chestertown, MD 21620
    • /72

      Est $844,212 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,743 Sq Ft

      7996 Aldan Dr, Chestertown, MD 21620

      7996 Aldan Dr, Chestertown, MD 21620
  • /30

    $398,000 Sold Jun 28, 2024

    • 1,854 Sq Ft
    • $215/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    1 Reed Ct, Chestertown, MD 21620

    You are invited to come see this beautiful NEW LISTING in quaint Chestertown located on a lovely corner lot and offering great off-street parking for 4+ cars accessed from a rear entry alley way. This well-maintained split foyer features 3 Bedrooms and 2 Full Baths on the main level and a 4th Bedroom and additional half bath on the lower level. You'll love the quality appointments to include

    Carol Tinnin RE/MAX Leading Edge

    1 Reed Ct, Chestertown, MD 21620
    • /22

      Est $292,377 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,388 Sq Ft

      211 Manor Ave, Chestertown, MD 21620

      211 Manor Ave, Chestertown, MD 21620
  • /8

    $128,000 Sold Jun 28, 2024

    • Land
    • 3.76 Acres
    • $34,043 per Acre
    • 726 Days On Market

    0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620

    Back on the market: Buyer got cold feet the day of settlement. Tranquil countryside parcel perc approved and ready for you to build your dream home. Partially wooded and surrounded by farmland on a quiet road. Just minutes outside Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping,

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620
    • /56

      Est $772,473 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,414 Sq Ft

      10258 Mill Hollow Ln, Chestertown, MD 21620

      10258 Mill Hollow Ln, Chestertown, MD 21620
  • /86

    $2,395,000 Sold Jun 27, 2024

    • 3,232 Sq Ft
    • $741/SF
    • 19 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2011

    8974 S Bayview Dr, Chestertown, MD 21620

    Built on a 40-foot bluff overlooking the Chesapeake Bay facing west for nightly sunsets, this is a tour-de-force of design and luxury on the Eastern Shore of Maryland, with truly stunning views from every room. Follow your dreams with this resort-like property as a primary or secondary home. Drive along the maple-lined lighted drive to 1.5 acres of award-winning, irrigated, landscaped grounds

    Richard Keaveney Cross Street Realtors LLC

    8974 S Bayview Dr, Chestertown, MD 21620
    • /12

      Est $743,602 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft

      8042 Brices Mill Rd, Chestertown, MD 21620

      8042 Brices Mill Rd, Chestertown, MD 21620
  • /13

    $350,000 Sold Jun 26, 2024

    • 2,153 Sq Ft
    • $163/SF
    • 12 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1952

    7671 Waterview Ln, Chestertown, MD 21620

    Chestertown Rancher in Country Club Estates! This rancher overlooks the golf course with distant water views. Amenities include fireplace, 2 car detached garage, storage building, wood floors, dining room, circular driveway, and laundry room. This is a Fannie Mae Homepath property. Submit all offers on Homepath site. Downtown Chestertown with restaurants and shops is a short drive away.

    Aaron Butler Real Estate Consultants

    7671 Waterview Ln, Chestertown, MD 21620
    • /17

      Est $248,086 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,237 Sq Ft

      10755 Glenola Rd, Chestertown, MD 21620

      10755 Glenola Rd, Chestertown, MD 21620
  • /28

    $269,975 Sold Jun 26, 2024

    • 1,376 Sq Ft
    • $196/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    106 Pine St, Chestertown, MD 21620

    Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.

    Beth Ostrander Doug Ashley Realtors, LLC

    106 Pine St, Chestertown, MD 21620
    • /25

      Est $338,130 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      8550 Caulks Field Rd, Chestertown, MD 21620

      8550 Caulks Field Rd, Chestertown, MD 21620
  • /32

    $345,000 Sold Jun 25, 2024

    • 1,812 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    23530 Clarissa Rd, Chestertown, MD 21620

    Welcome to 23530 Clarissa Road! This well maintained home is established on a beautifully situated lot located within the water access community of Chesapeake Landing. You'll be greeted here by vibrant greens, found flourishing through mature surrounding woods and meticulously cared for landscaping. Find your seat and enjoy peace in nature as an abundance of wildlife can be heard and seen

    Andrew Meikle Doug Ashley Realtors, LLC

    23530 Clarissa Rd, Chestertown, MD 21620
    • /42

      Est $298,832 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,855 Sq Ft

      626 High St, Chestertown, MD 21620

      626 High St, Chestertown, MD 21620
  • /41

    $645,000 Sold Jun 25, 2024

    • 2,866 Sq Ft
    • $225/SF
    • 179 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1900

    106-1 N Water St Unit 1/2, Chestertown, MD 21620

    This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel

    Richard Keaveney Cross Street Realtors LLC

    106-1 N Water St Unit 1/2, Chestertown, MD 21620
    • /28

      Est $256,121 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft

      403 E Campus Ave, Chestertown, MD 21620

      403 E Campus Ave, Chestertown, MD 21620
  • /32

    $324,000 Sold Jun 21, 2024

    • 1,505 Sq Ft
    • $215/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    22939 Bay Shore Rd, Chestertown, MD 21620

    Welcome to your Eastern Shore haven! This charming property boasts recent updates and in a prime location, offering the perfect blend of modern comfort and public water access to Fairlee Creek & the Chesapeake Bay!Enjoy the 6ft privacy fence that enhances the privacy and security, allowing a safe haven for pets and family or easily store your boat with the double gate entrance. Enjoy the

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    22939 Bay Shore Rd, Chestertown, MD 21620
    • /8

      Est $422,077 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft

      219 Philosophers Terrace, Chestertown, MD 21620

      219 Philosophers Terrace, Chestertown, MD 21620
  • /12

    $1,000,000 Sold Jun 21, 2024

    • 2,945 Sq Ft
    • $340/SF
    • 9 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1917

    204 Truslow Farm Ln, Chestertown, MD 21620

    Extraordinary opportunity to purchase the estate of Clorea Truslow—the cherished namesake of Truslow Rd. For generations, this land has been held dear by the Truslow family, and now, for the first time, it is being offered for sale, presenting a once-in-a-lifetime chance to make it your own.Nestled just across the river from the vibrant events of the Sulatana, Downrigging, Tea Party

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    204 Truslow Farm Ln, Chestertown, MD 21620
    • /4

      Est $465,351 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,693 Sq Ft

      928 Gateway Dr, Chestertown, MD 21620

      928 Gateway Dr, Chestertown, MD 21620
  • /7

    $500,000 Sold Jun 21, 2024

    • Land
    • 3.23 Acres
    • $154,799 per Acre
    • 77 Days On Market

    210 Truslow Farm Ln, Chestertown, MD 21620

    Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases, eagerly awaiting your imagination to bring them to life.For years,

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    210 Truslow Farm Ln, Chestertown, MD 21620
    • /34

      Est $675,453 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,683 Sq Ft

      112 S Mill St, Chestertown, MD 21620

      112 S Mill St, Chestertown, MD 21620
  • /40

    $263,000 Sold Jun 14, 2024

    • 1,232 Sq Ft
    • $213/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 2019

    7488 Poplar Ave, Chestertown, MD 21620

    Welcome to 7488 Poplar Ave in the heart of Chestertown. This charming 3-bedroom, 2-bath rancher nestled in a serene setting, backing onto scenic woods. Built in 2019, this modern home offers a perfect blend of comfort and style.As you step inside, you'll be greeted by a spacious open floor plan illuminated by natural light. The living area features luxurious LVP (Luxury Vinyl Plank)

    Crystal Smith RE/MAX Executive

    7488 Poplar Ave, Chestertown, MD 21620
    • /59

      Est $893,391 Not Listed For Sale

      • 6 Beds
      • 6 Baths
      • 6,334 Sq Ft

      954 High St, Chestertown, MD 21620

      954 High St, Chestertown, MD 21620
  • /22

    $1,200,000 Sold Jun 14, 2024

    • 2,028 Sq Ft
    • $592/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    9220 N Bayview Ave, Chestertown, MD 21620

    Stunning home with 180-degree views of the Chesapeake Bay Welcome to 9220 N. Bayview Avenue. This quintessential Cape Cod is perched on a half-acre of beautifully landscaped property with amazing views of the Bay. Highlights include a bright open floorplan with hardwood floors and a view from every space, a loaded kitchen with quartz countertops and stainless steel appliances, a cozy

    Lynn Hilfiker Gunther-McClary Real Estate

    9220 N Bayview Ave, Chestertown, MD 21620
    • /40

      Est $362,786 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,790 Sq Ft

      7653 Broad Neck Rd, Chestertown, MD 21620

      7653 Broad Neck Rd, Chestertown, MD 21620
  • /4

    $130,000 Sold Jun 14, 2024

    • Land
    • 1.00 Acre
    • $130,000 per Acre
    • 179 Days On Market

    0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620

    Lot 5- A one acre building lot in the desirable Prestwick community on the golf course. No builder tie-in. Public sewer and well water. Surrounded by mature beech trees. Roads will have final paving after the last few lots are sold. Prestwick is a 12 lot community next to Chester River Yacht and Country Club, 4 miles from Chestertown. A perfect place to build your dream home.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    0 Muirfield Dr Unit MDKE2002984, Chestertown, MD 21620
    • /41

      Est $423,817 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,422 Sq Ft

      203 Leeds Ct, Chestertown, MD 21620

      203 Leeds Ct, Chestertown, MD 21620
  • /34

    $499,000 Sold Jun 12, 2024

    • 1,624 Sq Ft
    • $307/SF
    • 39 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1970

    9816 Fairlee Rd, Chestertown, MD 21620

    Price Reduced $20k!!! Buyers got cold feet! Their loss is your win!Discovery your sanctuary on this 6 plus acre property, nestled on the outskirts of Chestertown. The property houses an abundance of wildlife such as deer, turkey, fox, and ducks! You might even find a beaver swimming up the creek. Thoughtfully updated, you won’t want to miss this a little over 1600 sq ft 3 bedroom 3 bath home,

    Jennifer Thomas RE/MAX Executive

    9816 Fairlee Rd, Chestertown, MD 21620
    • /15

      Est $220,339 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft

      7509 Sunburst Ave, Chestertown, MD 21620

      7509 Sunburst Ave, Chestertown, MD 21620
  • /31

    $340,000 Sold Jun 06, 2024

    • 1,296 Sq Ft
    • $262/SF
    • 75 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    707 Round Top Rd, Chestertown, MD 21620

    Be sure to check out the photos - this home has real charm and character! This well-maintained house has been home to the same family since 1975: blacktopped driveway resealed in 2022, new roof 2017, new well 2016, quarterly Pest Service and mature landscaping with a fenced backyard. New washer and dryer and a full tank of propane for use of the attractive oak fireplace. Both bathrooms

    Jo Ann Edwards The Hogans Agency

    707 Round Top Rd, Chestertown, MD 21620
    • /39

      Est $316,401 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,444 Sq Ft

      100 Malone Ave, Chestertown, MD 21620

      100 Malone Ave, Chestertown, MD 21620
  • /28

    $485,000 Sold Jun 04, 2024

    • 4,067 Sq Ft
    • $119/SF
    • 3 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2009

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown, where this captivating colonial-style home awaits you! Built in 2009, this meticulously maintained property offers over 4000 square feet of living space across three levels, including a spacious finished basement.As you arrive, you'll notice the inviting brick front and the convenience of an attached two-car garage. Inside, the main level boasts a

    Robert Kaetzel Real Estate Professionals, Inc.

    116 Harlan Loop, Chestertown, MD 21620
    • /57

      Est $552,355 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,693 Sq Ft

      206 Leeds Ct, Chestertown, MD 21620

      206 Leeds Ct, Chestertown, MD 21620
  • /23

    $232,000 Sold May 31, 2024

    • 1,280 Sq Ft
    • $181/SF
    • 12 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1979

    104 Conley Dr, Chestertown, MD 21620

    Introducing a fantastic opportunity for move-in ready living in the heart of Chestertown! This townhouse, priced under $250,000, offers the ideal blend of convenience and comfort. Situated for easy access to local amenities including shops, schools, and the YMCA, this property provides low-maintenance living at its finest. Featuring a fenced rear yard, this home is perfect for outdoor

    Jordan Larigan VYBE Realty

    104 Conley Dr, Chestertown, MD 21620

Showing Results 401 - 440, Page 11 of 18

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