7,012

Homes in ZIP Code 21620

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  • 0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    /32

    $39,000

    • Land
    • 1.51 Acres
    • $25,828 per Acre

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
  • 204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    /30

    $400,000 Sold Mar 12, 2025

    204 Pine Cove Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft
    • Built 2021

    Last Sold Summary

    • $185/SF
    • 19 Days On Market

    Current Estimated Value $406,089

    Last Listing Agent Kelly Harris Coldwell Banker Realty

    204 Pine Cove Ln, Chestertown, MD 21620
    • 23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      /7

      Est $317,479 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft

      23235 Myers Rd, Chestertown, MD 21620

      23235 Myers Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
    /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home!Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • 105 Justin Buch Dr, Chestertown, MD 21620
    105 Justin Buch Dr, Chestertown, MD 21620
    105 Justin Buch Dr, Chestertown, MD 21620
    /39

    $355,000 Sold Mar 31, 2025

    105 Justin Buch Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1991

    Last Sold Summary

    • $296/SF
    • 19 Days On Market

    Current Estimated Value $349,493

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    105 Justin Buch Dr, Chestertown, MD 21620
    • 23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      /13

      Est $329,155 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      23399 Cloquet Rd, Chestertown, MD 21620

      23399 Cloquet Rd, Chestertown, MD 21620
  • 517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    /51

    $389,900 Pending

    • Studio
    • 1,728 Sq Ft

    517 High St, Chestertown, MD 21620

    Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and cooling would be a window unit- super efficient space.The main

    Kristie Midash L. C. Parker Real Estate

    517 High St, Chestertown, MD 21620
  • 302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    302 Rosin Dr, Chestertown, MD 21620
    /70

    $550,000 Sold Dec 05, 2025

    302 Rosin Dr, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 3,877 Sq Ft
    • Built 1996

    Last Sold Summary

    • $142/SF
    • 5 Days On Market

    Last Listing Agent Lori Willis Cross Street Realtors LLC

    302 Rosin Dr, Chestertown, MD 21620
    • 101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      /39

      Est $322,921 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft

      101 S College Ave, Chestertown, MD 21620

      101 S College Ave, Chestertown, MD 21620
  • 24543 Chestertown Rd, Chestertown, MD 21620
    24543 Chestertown Rd, Chestertown, MD 21620
    24543 Chestertown Rd, Chestertown, MD 21620
    /55

    $425,000 Pending

    • 3 Beds
    • 2 Baths
    • 3,280 Sq Ft

    24543 Chestertown Rd, Chestertown, MD 21620

    Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home offers incredible potential for those looking to earn a little sweat equity. This home is ready for a buyer looking to uncover its true potential. Boasting 3 large bedrooms, a very large room on 2nd level could be a bedroom ? game room ? you decide, 3 flexible spaces that can be used as offices, dens, or

    Terri Murray RE/MAX Executive

    24543 Chestertown Rd, Chestertown, MD 21620
  • 104 Oak Leaf Dr, Chestertown, MD 21620
    104 Oak Leaf Dr, Chestertown, MD 21620
    104 Oak Leaf Dr, Chestertown, MD 21620
    /17

    $283,000 Sold Feb 19, 2025

    104 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 1,840 Sq Ft
    • Built 2003

    Last Sold Summary

    • $154/SF
    • 38 Days On Market

    Current Estimated Value $301,923

    Last Listing Agent Krystal Zellner Crown Homes Real Estate

    104 Oak Leaf Dr, Chestertown, MD 21620
    • 203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      /12

      Est $359,025 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft

      203 Radcliffe Dr, Chestertown, MD 21620

      203 Radcliffe Dr, Chestertown, MD 21620
  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /67

    $409,900

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Views from Every Angle!Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living. This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy entertaining

    Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • 305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    305 Washington Ave, Chestertown, MD 21620
    /28

    $549,000 Sold Jun 26, 2025

    305 Washington Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • Built 1930

    Last Sold Summary

    • $222/SF
    • 0 Days On Market

    Current Estimated Value $556,757

    Last Listing Agent William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
    • 316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      /27

      Est $269,588 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      316 Roosevelt Dr, Chestertown, MD 21620

      316 Roosevelt Dr, Chestertown, MD 21620
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /26

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Tom Riccio RE/MAX Point Realty

    127 Wood Duck Ln, 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

    $535,000 Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • 105 S Kent St, Chestertown, MD 21620
      105 S Kent St, Chestertown, MD 21620
      105 S Kent St, Chestertown, MD 21620
      /30

      Est $455,733 Not Listed For Sale

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

      105 S Kent St, Chestertown, MD 21620

      105 S Kent St, Chestertown, MD 21620
  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    26865 Mallard Rd, Chestertown, MD 21620
    /49

    $840,000 Sold Jun 27, 2025

    26865 Mallard Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,355 Sq Ft
    • Built 1963

    Last Sold Summary

    • $250/SF
    • 182 Days On Market

    Current Estimated Value $907,318

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
    • 21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      /13

      Est $240,035 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft

      21286 Maine Ave, Chestertown, MD 21620

      21286 Maine Ave, Chestertown, MD 21620
  • 10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    /50

    $350,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft

    10751 Millbrook Dr, Chestertown, MD 21620

    Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another

    Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, 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 Sold Jun 23, 2025

    811 S Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 2002

    Last Sold Summary

    • $222/SF
    • 4 Days On Market

    Current Estimated Value $466,200

    Last Listing Agent Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
    • 208 W Campus Ave, Chestertown, MD 21620
      208 W Campus Ave, Chestertown, MD 21620
      208 W Campus Ave, Chestertown, MD 21620
      /30

      Est $408,620 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,390 Sq Ft

      208 W Campus Ave, Chestertown, MD 21620

      208 W Campus Ave, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $695,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, 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

    $285,000 Sold Aug 08, 2025

    117 N Water St Unit 3B, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft
    • Built 1886

    Last Sold Summary

    • $437/SF
    • 457 Days On Market

    Current Estimated Value $761,860

    Last Listing Agent John Burke Gunther-McClary Real Estate

    117 N Water St Unit 3B, Chestertown, MD 21620
    • 545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      /28

      Est $279,337 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft

      545 High St, Chestertown, MD 21620

      545 High St, Chestertown, MD 21620
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    /14

    $85,000 Sold Oct 01, 2025

    236 Merganser Dr, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1973

    Last Sold Summary

    • $94/SF
    • 118 Days On Market

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
    • 9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      /47

      Est $338,619 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft

      9041 S Bayview Dr, Chestertown, MD 21620

      9041 S Bayview Dr, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, 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

    212 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 1972

    Last Sold Summary

    • $280/SF
    • 2 Days On Market

    Current Estimated Value $307,091

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    212 Central Dr, Chestertown, MD 21620
    • 10069 John Carvill Rd, Chestertown, MD 21620
      10069 John Carvill Rd, Chestertown, MD 21620
      10069 John Carvill Rd, Chestertown, MD 21620
      /69

      Est $1,229,071 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,869 Sq Ft

      10069 John Carvill Rd, Chestertown, MD 21620

      10069 John Carvill Rd, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    /2

    $539,000 Sold Jun 16, 2025

    107 N Queen St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 3,050 Sq Ft
    • Built 1879

    Last Sold Summary

    • $177/SF
    • 1 Day On Market

    Current Estimated Value $558,367

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
    • 217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      /37

      Est $513,731 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft

      217 Radcliffe Dr, Chestertown, MD 21620

      217 Radcliffe Dr, Chestertown, MD 21620
  • 303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    /32

    $363,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    303 E Campus Ave, Chestertown, MD 21620

    Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and

    Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
  • 477 Pear Tree Point Rd, Chestertown, MD 21620
    477 Pear Tree Point Rd, Chestertown, MD 21620
    477 Pear Tree Point Rd, Chestertown, MD 21620
    /20

    $355,000 Sold Mar 21, 2025

    477 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft
    • Built 2024

    Last Sold Summary

    • $235/SF
    • 282 Days On Market

    Current Estimated Value $361,998

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    477 Pear Tree Point Rd, Chestertown, MD 21620
    • 502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      /45

      Est $425,866 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft

      502 Cannon St, Chestertown, MD 21620

      502 Cannon St, Chestertown, MD 21620
  • 7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    /24

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    7521 Pine Ave, Chestertown, MD 21620

    Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620

Showing Results 321 - 360, Page 9 of 18

Maryland Kent County Chestertown 21620

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