861

Kent, MD Homes

Section Image
  • 0 Truslow Farm Ln, Chestertown, MD 21620
    0 Truslow Farm Ln, Chestertown, MD 21620
    0 Truslow Farm Ln, Chestertown, MD 21620
    /10

    $390,000 Sold Feb 06, 2025

    • Land
    • 2.30 Acres
    • $169,565 per Acre
    • 322 Days On Market

    0 Truslow Farm Ln, Chestertown, MD 21620

    Opportunity to claim your own 2.3 acres of waterfront situated amidst the serene beauty of Truslow farm. This parcel represents one of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring it to life as your dream home or waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Truslow Farm Ln, Chestertown, MD 21620
    • 112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      /21

      Est $344,831 Not Listed For Sale

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

      112 Pine Chip Rd, Chestertown, MD 21620

      112 Pine Chip Rd, Chestertown, MD 21620
  • 107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    /23

    $299,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    107 Dutchess Rd, Chestertown, MD 21620

    Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen

    Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
  • 125 Primrose Rd, Chestertown, MD 21620
    125 Primrose Rd, Chestertown, MD 21620
    125 Primrose Rd, Chestertown, MD 21620
    /48

    $350,000 Sold Dec 30, 2024

    • 2,102 Sq Ft
    • $167/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    125 Primrose Rd, Chestertown, MD 21620

    **Seller has purchased a new dishwasher and it will be installed in the coming days. Tucked away in a wooded setting in a quiet neighborhood just a block off the Chester River you will find this well built welcoming home. The well designed main floor layout includes a living room, dining room, and eat in kitchen plus a year round spacious sunroom overlooking the back yard and the open space

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    125 Primrose Rd, Chestertown, MD 21620
    • 201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      /5

      Est $175,000 Not Listed For Sale

      201 Duke of Kent St, Chestertown, MD 21620

      201 Duke of Kent St, Chestertown, MD 21620
  • 411 Fairview Dr, Chestertown, MD 21620
    411 Fairview Dr, Chestertown, MD 21620
    411 Fairview Dr, Chestertown, MD 21620
    /30

    $649,000 Sold Dec 20, 2024

    • 1,680 Sq Ft
    • $386/SF
    • 27 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    411 Fairview Dr, Chestertown, MD 21620

    Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around water views in a serene wooded setting. With convenient single level living, the three bedroom two bathroom home offers a flowing floor plan bright with natural light and custom upgrades. Relax and enjoy views from the private walkout

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    411 Fairview Dr, Chestertown, MD 21620
    • 208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      /23

      Est $281,620 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft

      208 Central Dr, Chestertown, MD 21620

      208 Central Dr, Chestertown, MD 21620
  • 221 River Rd, Chestertown, MD 21620
    221 River Rd, Chestertown, MD 21620
    221 River Rd, Chestertown, MD 21620
    /80

    $385,000 Sold Dec 20, 2024

    • 2,240 Sq Ft
    • $172/SF
    • 35 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1969

    221 River Rd, Chestertown, MD 21620

    Hidden within the wandering gardens, you will find this meticulously maintained home with seasonal water views of the Chester River in a quiet family-friendly community just minutes from Chestertown. The spacious front and back yards are private oases with just about every tree or plant one can think of; a true gardner's dream. Enjoy the fall colors from the back screened-in porch. Inside you

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    221 River Rd, Chestertown, MD 21620
    • 224 Fey Rd, Chestertown, MD 21620
      224 Fey Rd, Chestertown, MD 21620
      224 Fey Rd, Chestertown, MD 21620
      /25

      Est $374,803 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft

      224 Fey Rd, Chestertown, MD 21620

      224 Fey Rd, Chestertown, MD 21620
  • 228 Concord Rd, Chestertown, MD 21620
    228 Concord Rd, Chestertown, MD 21620
    228 Concord Rd, Chestertown, MD 21620
    /26

    $325,000 Sold Dec 12, 2024

    • 1,500 Sq Ft
    • $217/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1974

    228 Concord Rd, Chestertown, MD 21620

    This 1500 sq. foot rancher sits on a nice open lot with plenty of parking and room to grow and make your own . Main level offers eat in kitchen, an oversized living room with fireplace , four bedrooms and two full baths. One of the bedrooms could make a perfect home office. This home has been freshly painted and new flooring. This will get the new owners a fresh start while they decide on

    Grace Crockett Doug Ashley Realtors, LLC

    228 Concord Rd, Chestertown, MD 21620
    • 206 Tamarack Rd, Chestertown, MD 21620
      206 Tamarack Rd, Chestertown, MD 21620
      206 Tamarack Rd, Chestertown, MD 21620
      /16

      Est $386,084 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft

      206 Tamarack Rd, Chestertown, MD 21620

      206 Tamarack Rd, Chestertown, MD 21620
  • 218 Concord Rd, Chestertown, MD 21620
    218 Concord Rd, Chestertown, MD 21620
    218 Concord Rd, Chestertown, MD 21620
    /22

    $342,000 Sold Dec 09, 2024

    • 1,200 Sq Ft
    • $285/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1997

    218 Concord Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher located in the desirable Chester Harbor neighborhood! This move-in-ready home features a recently updated kitchen with quartz counters and new flooring in the bedrooms. New heat pump. Enjoy the spacious, fenced-in backyard complete with a screened-in porch and fire pit. A large shed offers extra storage. Conveniently situated just minutes from downtown

    Courtney Chipouras TTR Sotheby's International Realty

    218 Concord Rd, Chestertown, MD 21620
    • 240 Duke of Kent St, Chestertown, MD 21620
      240 Duke of Kent St, Chestertown, MD 21620
      240 Duke of Kent St, Chestertown, MD 21620
      /33

      Est $430,677 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft

      240 Duke of Kent St, Chestertown, MD 21620

      240 Duke of Kent St, Chestertown, MD 21620
  • 201 Princess Anne Dr, Chestertown, MD 21620
    201 Princess Anne Dr, Chestertown, MD 21620
    201 Princess Anne Dr, Chestertown, MD 21620
    /36

    $370,247 Sold Nov 15, 2024

    • 2,092 Sq Ft
    • $177/SF
    • 120 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    201 Princess Anne Dr, Chestertown, MD 21620

    Where Shore living begins! Welcome to 201 Princess Anne, located on the Queen Anne's County side of the Chester River Bridge. This well maintained home is established on just over 3/4 of an acre within the quiet subdivision of Kingstowne Manor. Offering 3 bedrooms, 2 baths, attached garage and comes equipped with a fully floored attic for all of your storage needs! A new roof system was

    Andrew Meikle Doug Ashley Realtors, LLC

    201 Princess Anne Dr, Chestertown, MD 21620
    • 210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      /42

      Est $374,675 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,352 Sq Ft

      210 Rosin Dr, Chestertown, MD 21620

      210 Rosin Dr, Chestertown, MD 21620
  • 121 Fairview Dr, Chestertown, MD 21620
    121 Fairview Dr, Chestertown, MD 21620
    121 Fairview Dr, Chestertown, MD 21620
    /25

    $349,000 Sold Nov 08, 2024

    • 1,232 Sq Ft
    • $283/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    121 Fairview Dr, Chestertown, MD 21620

    Great opportunity to own a quality built home by Coldwell Builders. Larger than average lot for the community so room to grow on this one. New home features open design with large central kitchen, dining, living area and split bedroom design. Quartz counters and stainless steel appliances in the kitchen, carpet in bedrooms and LVP everywhere else. Large yard affords many uses. Community has

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    121 Fairview Dr, Chestertown, MD 21620
    • 216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      216 Princess Anne Dr, Chestertown, MD 21620
      /62

      Est $386,857 Not Listed For Sale

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

      216 Princess Anne Dr, Chestertown, MD 21620

      216 Princess Anne Dr, Chestertown, MD 21620
  • 205 Creston Rd, Chestertown, MD 21620
    205 Creston Rd, Chestertown, MD 21620
    205 Creston Rd, Chestertown, MD 21620
    /22

    $337,000 Sold Nov 08, 2024

    • 1,338 Sq Ft
    • $252/SF
    • 16 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1975

    205 Creston Rd, Chestertown, MD 21620

    Located in a desirable community, this charming 3-bedroom, 1-bath home offers the perfect blend of comfort, convenience, and style. Situated on a generous lot, the property provides ample outdoor space for relaxation or entertaining, making it ideal for families or anyone who enjoys the outdoors.As you step inside, you'll be welcomed by a spacious living room featuring vaulted ceilings that

    Jarnell Foster Benson & Mangold, LLC

    205 Creston Rd, Chestertown, MD 21620
    • 306 Rosin Dr, Chestertown, MD 21620
      306 Rosin Dr, Chestertown, MD 21620
      306 Rosin Dr, Chestertown, MD 21620
      /25

      Est $423,980 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,871 Sq Ft

      306 Rosin Dr, Chestertown, MD 21620

      306 Rosin Dr, Chestertown, MD 21620
  • 204 Princess Anne Dr, Chestertown, MD 21620
    204 Princess Anne Dr, Chestertown, MD 21620
    204 Princess Anne Dr, Chestertown, MD 21620
    /35

    $359,000 Sold Nov 08, 2024

    • 1,500 Sq Ft
    • $239/SF
    • 82 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    204 Princess Anne Dr, Chestertown, MD 21620

    Welcome home to this 3 BR 2 bath home in Kingstown Manor, situated on 1/2 acre just seconds from the Chester River. Newly refinished flooring throughout! The gorgeous, custom tiled backsplash, updated kitchen includes stainless steel appliances and is open to the dining area with built in bench seating. From the dining area you can exit the rear door onto the patio overlooking the fenced backyard

    Jamil Wright EXP Realty, LLC

    204 Princess Anne Dr, Chestertown, MD 21620
    • 545 Fey Rd, Chestertown, MD 21620
      545 Fey Rd, Chestertown, MD 21620
      545 Fey Rd, Chestertown, MD 21620
      /8

      Est $1,292,330 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,420 Sq Ft

      545 Fey Rd, Chestertown, MD 21620

      545 Fey Rd, Chestertown, MD 21620
  • 319 Fairview Dr, Chestertown, MD 21620
    319 Fairview Dr, Chestertown, MD 21620
    319 Fairview Dr, Chestertown, MD 21620
    /37

    $675,000 Sold Oct 21, 2024

    • 2,128 Sq Ft
    • $317/SF
    • 1 Day On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1961

    319 Fairview Dr, Chestertown, MD 21620

    Live authentically. Welcome to your dream waterfront oasis! This charming home, nestled in a serene spot near historic Chestertown, offers the perfect blend of community amenities and private retreat. Boasting three bedrooms and two beautifully designed bathrooms, this property is the epitome of move-in ready.Step inside to discover a host of updates that ensure modern convenience without

    Michelle Schwab Krauss Real Property Brokerage

    319 Fairview Dr, Chestertown, MD 21620
    • 120 Edmore Rd, Chestertown, MD 21620
      120 Edmore Rd, Chestertown, MD 21620
      120 Edmore Rd, Chestertown, MD 21620
      /18

      Est $335,171 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      120 Edmore Rd, Chestertown, MD 21620

      120 Edmore Rd, Chestertown, MD 21620
  • 209 Princess Anne Dr, Chestertown, MD 21620
    209 Princess Anne Dr, Chestertown, MD 21620
    209 Princess Anne Dr, Chestertown, MD 21620
    /26

    $398,000 Sold Sep 27, 2024

    • 1,776 Sq Ft
    • $224/SF
    • 45 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2001

    209 Princess Anne Dr, Chestertown, MD 21620

    Welcome to 209 Princess Anne Drive, a delightful 3-bedroom, 2-bathroom home nestled on a double lot in the heart of Chestertown, Maryland. As you step into the grand foyer, you'll immediately appreciate the spaciousness and elegance this home offers.This meticulously maintained residence boasts three comfortable bedrooms that provide ample space for relaxation and privacy. The property

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    209 Princess Anne Dr, Chestertown, MD 21620
    • 102 Concord Rd, Chestertown, MD 21620
      102 Concord Rd, Chestertown, MD 21620
      102 Concord Rd, Chestertown, MD 21620
      /16

      Est $343,680 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      102 Concord Rd, Chestertown, MD 21620

      102 Concord Rd, Chestertown, MD 21620
  • 105 Coleman Dr, Chestertown, MD 21620
    105 Coleman Dr, Chestertown, MD 21620
    105 Coleman Dr, Chestertown, MD 21620
    /45

    $440,000 Sold Sep 16, 2024

    • 2,128 Sq Ft
    • $207/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    105 Coleman Dr, Chestertown, MD 21620

    KINGS COURT! This Colonial, sited on an acre of land, is move-in ready and boasts so many wonderful features! Here are just some that are sure to pique your interest! Freshly painted; gleaming floors; stainless steel appliances; lots of counter and cabinet space; breakfast room; separate pantry space; family room with large picture window; fireplace with stainless steel liner; newer LG washer and

    Jenn Klarman Long & Foster Real Estate, Inc.

    105 Coleman Dr, Chestertown, MD 21620
    • 119 Darden Rd, Chestertown, MD 21620
      119 Darden Rd, Chestertown, MD 21620
      119 Darden Rd, Chestertown, MD 21620
      /48

      Est $335,041 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,424 Sq Ft

      119 Darden Rd, Chestertown, MD 21620

      119 Darden Rd, Chestertown, MD 21620
  • 201 Tamarack Rd, Chestertown, MD 21620
    201 Tamarack Rd, Chestertown, MD 21620
    201 Tamarack Rd, Chestertown, MD 21620
    /50

    $342,000 Sold Aug 14, 2024

    • 1,225 Sq Ft
    • $279/SF
    • 1 Day On Market
    • 2 Beds
    • 2 Baths
    • Built 1973

    201 Tamarack Rd, Chestertown, MD 21620

    Discover the charm and tranquility of this inviting ranch-style home, perfectly situated on the Queen Anne's County side of Chestertown, Maryland. Just steps from Rosin Creek, this property offers not only spacious living but also exciting opportunities for canoeing, boating, fishing, and crabbing on the beautiful Chester River.Step inside to find large, airy bedrooms, a generously sized

    Petra Quinn Realty Navigator

    201 Tamarack Rd, Chestertown, MD 21620
    • 109 Coleman Dr, Chestertown, MD 21620
      109 Coleman Dr, Chestertown, MD 21620
      109 Coleman Dr, Chestertown, MD 21620
      /49

      Est $427,785 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,792 Sq Ft

      109 Coleman Dr, Chestertown, MD 21620

      109 Coleman Dr, Chestertown, MD 21620
  • 332 Truslow Rd, Chestertown, MD 21620
    332 Truslow Rd, Chestertown, MD 21620
    332 Truslow Rd, Chestertown, MD 21620
    /29

    $252,400 Sold Aug 12, 2024

    • 1,408 Sq Ft
    • $179/SF
    • 118 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    332 Truslow Rd, Chestertown, MD 21620

    Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a

    James Blackwell Blackwell Real Estate, LLC

    332 Truslow Rd, Chestertown, MD 21620
    • 236 Duke of Kent St, Chestertown, MD 21620
      236 Duke of Kent St, Chestertown, MD 21620
      236 Duke of Kent St, Chestertown, MD 21620
      /29

      Est $402,497 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,780 Sq Ft

      236 Duke of Kent St, Chestertown, MD 21620

      236 Duke of Kent St, Chestertown, MD 21620
  • 415 Fairview Dr, Chestertown, MD 21620
    415 Fairview Dr, Chestertown, MD 21620
    415 Fairview Dr, Chestertown, MD 21620
    /24

    $718,000 Sold Aug 09, 2024

    • 1,376 Sq Ft
    • $522/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    415 Fairview Dr, Chestertown, MD 21620

    Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around waterviews in a serene wooded setting. With convenient single level living, the three bedroom one-and-half bath home offers an open flowing floorplan bright with natural light and custom wood detail. Relax and enjoy views from the

    Richard Budden Coldwell Banker Chesapeake Real Estate Company

    415 Fairview Dr, Chestertown, MD 21620
    • 313 River Rd, Chestertown, MD 21620
      313 River Rd, Chestertown, MD 21620
      313 River Rd, Chestertown, MD 21620
      /35

      Est $416,685 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,080 Sq Ft

      313 River Rd, Chestertown, MD 21620

      313 River Rd, Chestertown, MD 21620
  • 101 Rivershore Rd, Chestertown, MD 21620
    101 Rivershore Rd, Chestertown, MD 21620
    /2

    $1,125,000 Sold Jun 10, 2025

    • 1,968 Sq Ft
    • $572/SF
    • 3 Beds
    • 2 Baths
    • Built 1950

    101 Rivershore Rd, Chestertown, MD 21620

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 Rivershore Rd, Chestertown, MD 21620
    • 109 Essex Rd, Chestertown, MD 21620
      109 Essex Rd, Chestertown, MD 21620
      109 Essex Rd, Chestertown, MD 21620
      /26

      Est $380,349 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,920 Sq Ft

      109 Essex Rd, Chestertown, MD 21620

      109 Essex Rd, Chestertown, MD 21620
    • 124 Edmore Rd, Chestertown, MD 21620
      124 Edmore Rd, Chestertown, MD 21620
      124 Edmore Rd, Chestertown, MD 21620
      /28

      Est $278,063 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      124 Edmore Rd, Chestertown, MD 21620

      124 Edmore Rd, Chestertown, MD 21620
    • 729 Rosin Dr, Chestertown, MD 21620
      729 Rosin Dr, Chestertown, MD 21620
      729 Rosin Dr, Chestertown, MD 21620
      /32

      Est $306,188 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      729 Rosin Dr, Chestertown, MD 21620

      729 Rosin Dr, Chestertown, MD 21620
    • 319 Round Top Rd, Chestertown, MD 21620
      319 Round Top Rd, Chestertown, MD 21620
      319 Round Top Rd, Chestertown, MD 21620
      /16

      Est $243,886 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft

      319 Round Top Rd, Chestertown, MD 21620

      319 Round Top Rd, Chestertown, MD 21620
    • 332 Longfellow Dr, Chestertown, MD 21620
      332 Longfellow Dr, Chestertown, MD 21620
      332 Longfellow Dr, Chestertown, MD 21620
      /19

      Est $306,352 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,263 Sq Ft

      332 Longfellow Dr, Chestertown, MD 21620

      332 Longfellow Dr, Chestertown, MD 21620
    • 537 Truslow Rd, Chestertown, MD 21620
      537 Truslow Rd, Chestertown, MD 21620
      537 Truslow Rd, Chestertown, MD 21620
      /43

      Est $319,284 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,304 Sq Ft

      537 Truslow Rd, Chestertown, MD 21620

      537 Truslow Rd, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 18

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