7,060

Homes in ZIP Code 21620

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  • /26

    $274,000 Under Contract

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

    118 Tuxedo Rd, Chestertown, MD 21620

    Three bedroom/one bath rancher located in a water-oriented community just minutes from Chestertown. There is a Home Owners Association; however, is not mandatory to join. Home is being sold as is.

    Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo Rd, Chestertown, MD 21620
  • /50

    $501,000 Sold Nov 14, 2024

    • 2,208 Sq Ft
    • $227/SF
    • 35 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1984

    217 Birch Run Rd, Chestertown, MD 21620

    Price improvement! Beautiful cape in the coveted Mile Tree Village with a lovely in-ground pool surrounded by a spacious patio. Large flowing rooms with lots of built-ins. Half bath on the main floor. Second floor has 4 bedrooms, 2 baths, laundry, and an unfinished bonus or storage room. Home needs some finishing touches from its new owners but a little effort will yield big rewards with this

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    217 Birch Run Rd, Chestertown, MD 21620
    • /41

      Est $388,047 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,537 Sq Ft

      208 N Mill St, Chestertown, MD 21620

      208 N Mill St, Chestertown, MD 21620
  • /60

    $799,000 Under Contract

    • 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
  • /56

    $866,395 Sold Nov 14, 2024

    • 3,355 Sq Ft
    • $258/SF
    • 130 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1936

    307 Washington Ave, Chestertown, MD 21620

    This stunning renovation is the jewel of Chestertown's revitalized upper historic district! A beautiful view of Washington College (9th best college in the country by Princeton Review), invites a walk around campus, to the river, or to the shops & restaurants in between. Extensive interior & exterior renovations along with plumbing, mechanical, and electrical upgrades throughout make the beauty

    Beth Ostrander Doug Ashley Realtors, LLC

    307 Washington Ave, Chestertown, MD 21620
    • /36

      Est $376,264 Not Listed For Sale

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

      10656 Millbrook Dr, Chestertown, MD 21620

      10656 Millbrook Dr, Chestertown, MD 21620
  • /17

    $349,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft

    110 Flying Cloud Dr, Chestertown, MD 21620

    SINGLE FAMILY HOME built just 2 years ago! Clean lines and neutral tones make this an easy move-in with nothing to do! Just across the Vintage Chester River Bridge, you will enter a charming little town that surrounds Washington College that has all sorts of new centers and places to go and things to do! The home offers a modern, open-concept layout with plenty of space and style. Large

    Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
  • /82

    $1,200,000 Sold Nov 13, 2024

    • 6,459 Sq Ft
    • $186/SF
    • 119 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2000

    22956 Fairgale Farm Ln, Chestertown, MD 21620

    Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also

    Retha Arrabal Doug Ashley Realtors, LLC

    22956 Fairgale Farm Ln, Chestertown, MD 21620
    • /34

      Est $402,663 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft

      202 Byford Dr, Chestertown, MD 21620

      202 Byford Dr, 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
  • /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
    • /69

      Est $1,251,099 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft

      9088 Point Ln, Chestertown, MD 21620

      9088 Point Ln, Chestertown, MD 21620
  • /3

    $9,500 Under Contract

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    Kent County Health Dept has no record of perc

    Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon 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
    • /22

      Est $475,230 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft

      7920 Carriage Ln, Chestertown, MD 21620

      7920 Carriage Ln, Chestertown, MD 21620
  • /2

    $30,000 Under Contract

    • Land
    • 0.83 Acre
    • $36,145 per Acre

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    Wooded 0.8+ acre building lot on Georgetown Rd in Fairlee, just minutes from Chestertown, Tolchester, Rock Hall, and the Fairlee Boat Ramp. Water and sewer assessment already paid—no perc test needed! A convenient and ready-to-build spot for your Eastern Shore getaway!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
  • /57

    $465,000 Sold Nov 08, 2024

    • 2,733 Sq Ft
    • $170/SF
    • 41 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2001

    126 Hilltop Dr, Chestertown, MD 21620

    Discover your dream home perched on a tranquil hill in Chestertown, Maryland. This beautiful 3-bedroom, 2.5-bathroom residence features lush landscaping and a welcoming front porch, ideal for enjoying scenic views. Inside, the open floor plan is filled with natural light, showcasing a spacious living room with a cozy fireplace and a gourmet kitchen that’s perfect for entertaining. The master

    Chardae Eduruke Taylor Properties

    126 Hilltop Dr, Chestertown, MD 21620
    • /34

      Est $430,414 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft

      209 E Campus Ave, Chestertown, MD 21620

      209 E Campus Ave, Chestertown, MD 21620
  • /2

    $29,000 Under Contract

    • Land
    • 2.00 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, 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
    • /55

      Est $622,406 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,952 Sq Ft

      25819 Collins Ave, Chestertown, MD 21620

      25819 Collins Ave, Chestertown, MD 21620
  • /36

    $249,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    It doesn’t get any more hometown than this new offering right smack in the heart of hometown Chestertown! It’s peaceful, it’s rural and it looks like a Norman Rockwell this town. This is the Eastern Shore at its finest with plenty amenities close to town and countless activities for those sportsman who like to hunt fish and crab. That’s what we do out here and you have the Chester River right in

    Joseph Craig Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • /43

    $411,500 Sold Nov 07, 2024

    • 810 Sq Ft
    • $508/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    129 Char Nor Manor Blvd, Chestertown, MD 21620

    Enjoy the serenity of waterfront living in this delightful 2-bedroom, 1-bath ranch home nestled along the scenic Chester River. This cozy retreat offers stunning, uninterrupted views of the water from nearly every room. Imagine spending your mornings sipping coffee on the private dock or screened porch, or relaxing by the warmth of the wood-burning fireplace on cool evenings.The open floor

    Melanie Musser Iron Valley Real Estate of Central PA

    129 Char Nor Manor Blvd, Chestertown, MD 21620
    • /64

      Est $1,580,755 Not Listed For Sale

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

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      9545 Chantilly Farm Ln, Chestertown, MD 21620
  • /14

    $147,000

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    236 Merganser Dr, Chestertown, MD 21620

    Looking for that off the beaten path property, here it is! Looking for water access without all the fees, here it is! Property located in a water privileged community on the Chester River, access at end of road. Investors this property could possibly make a great Airbnb property to add to the portfolio. Make this 1 bedroom possibly into 2. Home offers a 1/2 acre lot with mature trees. Subject

    Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
  • /35

    $406,000 Sold Nov 07, 2024

    • 1,509 Sq Ft
    • $269/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    813 S Meadowview Dr, Chestertown, MD 21620

    Nestled on the edge of the desirable Crestview neighborhood, this main level living home boasts beautiful hardwood floors, an easy flow perfect for entertaining, an ample screened in porch with views of the wooded back yard, and a walk-out, unfinished basement perfect for a gardening room or enclosed storage. Roof is only a few years young! Open house on Sept. 29th, 1-3pm.

    Liddy Campbell TTR Sotheby's International Realty

    813 S Meadowview Dr, Chestertown, MD 21620
    • /46

      Est $559,382 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,264 Sq Ft

      7898 Radcliffe Rd, Chestertown, MD 21620

      7898 Radcliffe Rd, Chestertown, MD 21620
  • /4

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Towhee Rd 21620

    ONLINE AUCTION: Bidding begins 8/19/2025 @ 10:00 AM. Bidding ends 8/21/2025 @ 12:50 PM. List Price is Suggested Opening Bid. 4 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in

    Adam Shpritz Ashland Auction Group LLC

    0 Towhee Rd 21620
  • /16

    $215,000 Sold Nov 04, 2024

    • 966 Sq Ft
    • $223/SF
    • 22 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    112 Snyder Ln, Chestertown, MD 21620

    ***Property back on market due to Buyer Default. ***This move-in ready home has been tastefully updated and is conveniently located close to downtown Chestertown while maintaining the benefits of Queen Anne's County. The primary suite has a spacious en suite bathroom and laundry area. An open floor plan provides plenty of living space and leads to another full bathroom and bedroom. An

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    112 Snyder Ln, Chestertown, MD 21620
    • /44

      Est $631,617 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
  • /4

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Bunting Rd, 6, Fairlee, MD 21620

    ONLINE AUCTION: Bidding begins 8/19/2025 @ 10:00 AM. Bidding ends 8/21/2025 @ 12:30 PM. List Price is Suggested Opening Bid. 4 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in

    Adam Shpritz Ashland Auction Group LLC

    0 Bunting Rd, 6, Fairlee, MD 21620
  • /25

    $299,900 Sold Nov 01, 2024

    • 1,464 Sq Ft
    • $205/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    8489 Broad Neck Rd, Chestertown, MD 21620

    Welcome to this newly updated 3-bedroom, 2-bathroom rancher, conveniently located on Broad Neck Road, just minutes from historic Chestertown! This home offers some nice upgrades such as a brand-new roof, gutters, and HVAC system, ensuring year-round comfort and a full unfinished basement with heating and air conditioning—perfect for extra storage or future expansion. The interior has been

    Jody Baker Cross Street Realtors LLC

    8489 Broad Neck Rd, Chestertown, MD 21620
    • /27

      Est $321,258 Not Listed For Sale

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

      10791 Foreston Rd, Chestertown, MD 21620

      10791 Foreston Rd, Chestertown, MD 21620
  • /6

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 8/19/2025 @ 10:00 AM. Bidding ends 8/21/2025 @ 12:20 PM. List Price is Suggested Opening Bid. 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to Worton Creek Marina, and all

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /37

    $600,000 Sold Nov 01, 2024

    • 3,240 Sq Ft
    • $185/SF
    • 6 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1900

    208 N Queen St, Chestertown, MD 21620

    Welcome to this charming Colonial four square home, nestled on the north end of Queen Street in Chestertown's historic district, just two blocks from the river. Step inside to find a beautifully remodeled kitchen, updated living room, dining room, den which doubles as a library or family room, and a sunlit porch, all on the main level. With high ceilings, intricate detailing, and polished

    Jody Baker Cross Street Realtors LLC

    208 N Queen St, Chestertown, MD 21620
    • /44

      Est $424,220 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,045 Sq Ft

      208 Byford Dr, Chestertown, MD 21620

      208 Byford Dr, Chestertown, MD 21620
  • /7

    $5,000

    • Land
    • 0.37 Acre
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 8/19/2025 @ 10:00 AM. Bidding ends 8/21/2025 @ 12:40 PM. List Price is Suggested Opening Bid. 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • /17

    $275,000 Sold Oct 29, 2024

    • 1,317 Sq Ft
    • $209/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    24105 Chestertown Rd, Chestertown, MD 21620

    Custom quality-built 1970 brick rancher on 0.46 acre lot just outside Chestertown. House features original hardwood floors, stained woodwork, trim moldings and hand built wood kitchen cabinetry. The living room has large bay window and brick wood burning fireplace. Full unfinished basement offers lots of extra storage space with room to expand. Attached carport with storage closets and

    Yvonne Andres Keller Williams Select Realtors of Annapolis

    24105 Chestertown Rd, Chestertown, MD 21620
    • /24

      Est $425,469 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,316 Sq Ft

      247 Devon Dr, Chestertown, MD 21620

      247 Devon Dr, Chestertown, MD 21620
  • /2

    $10,000

    • Land
    • 0.09 Acre
    • $111,111 per Acre

    0 Texas Ave, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    0 Texas Ave, Chestertown, MD 21620

Showing Results 361 - 400, Page 10 of 18

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