6,895

Chestertown, MD Homes

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    • /7

      Est $300,494 Not Listed For Sale

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

      23235 Myers Rd, Chestertown, MD 21620

      23235 Myers Rd, Chestertown, MD 21620
  • /87

    $1,200,000 Pending

    • 5 Beds
    • 6 Baths
    • 3,078 Sq Ft

    22153 1st Point Rd, Chestertown, MD 21620

    Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and

    Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
  • /25

    $565,000 Sold Nov 18, 2024

    • 2,488 Sq Ft
    • $227/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1980

    209 Birch Run Rd, Chestertown, MD 21620

    Upgrades GALORE... wait til you see how this house has been transformed into a home! A spacious four bedroom, three full bath layout on over half acre in one of Chestertown's most desirable neighborhoods: professional kitchen appliances, renovated bathrooms, high end flooring finishes, bonus sun room, fenced back yard, asphalt driveway heading to the two car garage... plus so much more. Live for

    Liddy Campbell TTR Sotheby's International Realty

    209 Birch Run Rd, Chestertown, MD 21620
    • /13

      Est $323,011 Not Listed For Sale

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

      23399 Cloquet Rd, Chestertown, MD 21620

      23399 Cloquet Rd, Chestertown, MD 21620
  • /72

    $625,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,155 Sq Ft

    10175 John Carvill Rd, Chestertown, MD 21620

    Welcome to 10175 John Carvill Road, nestled in the desirable water-oriented community of Great Oak Estates. This spacious home offers an open floor plan with 5 bedrooms and 3.5 baths, hardwood floors throughout the first floor, a cathedral ceiling, gas fireplace in the family room, and two primary suites. Enjoy the private fenced backyard and the sense of space that comes with it. The location of

    Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
  • /26

    $340,000 Sold Nov 18, 2024

    • 1,566 Sq Ft
    • $217/SF
    • 79 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    503 N Kent St, Chestertown, MD 21620

    Within walking distance of Washington College, medical services, parks and schools and convenient to historic downtown arts and entertainment district, this low-maintenance- exterior brick rancher is ready for your personal decorating touches. Living Room and formal dining room. One primary bedroom with en suite bath. Two additional bedrooms and a family bathroom. Country kitchen with

    Hugh Wyble Wyble Enterprises

    503 N Kent St, Chestertown, MD 21620
    • /39

      Est $310,489 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
  • /95

    $1,495,000 Pending

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft

    7961 Quaker Neck Rd, Chestertown, MD 21620

    Highest and Best Offers due by 7pm on Friday, 5/9. Open House - Cancelled.**Exquisite Waterfront Retreat on Chester River**Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four

    Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, 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
    • /12

      Est $313,766 Not Listed For Sale

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

      203 Radcliffe Dr, Chestertown, MD 21620

      203 Radcliffe Dr, Chestertown, MD 21620
  • /2

    $15,000 Pending

    • Land
    • 0.51 Acre
    • $29,412 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. The county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot. There is a 16' right of way to access which has not been maintained. Buyer to do any due diligence. Could be a great hunting property!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, 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
    • /14

      Est $224,540 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,000 Sq Ft

      21385 Pennsylvania Ave, Chestertown, MD 21620

      21385 Pennsylvania Ave, Chestertown, MD 21620
  • /39

    $575,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    25285 Foxchase Dr, Chestertown, MD 21620

    Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, 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
    • /24

      Est $298,059 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,234 Sq Ft

      211 Philosophers Terrace, Chestertown, MD 21620

      211 Philosophers Terrace, Chestertown, MD 21620
  • /56

    $749,900 Pending

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft

    7988 Aldan Dr, Chestertown, MD 21620

    This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor

    Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan 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
    • /36

      Est $966,772 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,352 Sq Ft

      9831 Breezecroft Ln, Chestertown, MD 21620

      9831 Breezecroft Ln, Chestertown, MD 21620
  • /66

    $5,500,000 Pending

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft

    23620 Lands End Rd, Chestertown, MD 21620

    Beautifully situated on the east fork of Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. Sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The

    Richard Keaveney Cross Street Realtors LLC

    23620 Lands End 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
    • /27

      Est $264,030 Not Listed For Sale

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

      316 Roosevelt Dr, Chestertown, MD 21620

      316 Roosevelt Dr, Chestertown, MD 21620
  • /52

    $795,000 Pending

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft

    211 David Dr, Chestertown, MD 21620

    Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, 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
    • /30

      Est $469,928 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
  • /18

    $665,610 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,599 Sq Ft

    3666 Gratitude Way, Chestertown, MD 21620

    TO BE BUILT......Welcome to Ryan Homes at Gilbert Meadows. Offering ranch style & 2-story single family homes with 1st floor primary suites in Harford County, MD. Minutes to Rte. 22 & I-95 - Starting from the low $500's. Our homes are designed to make your life easier with open and modern designs connecting all the spaces you use most! Plus, our homes all offer all the conveniences of main-level

    Tineshia Johnson NVR, INC.

    3666 Gratitude Way, 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
    • /44

      Est $662,535 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,536 Sq Ft

      225 Washington Ave, Chestertown, MD 21620

      225 Washington Ave, Chestertown, MD 21620
  • /2

    $1,350,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 2,909 Sq Ft

    209 N Water St, Chestertown, MD 21620

    One of the "stand-out" North Water Street waterfront homes in Historic Chestertown that has raised children, hosted town development meetings, entertained many, and most recently provided the perfect escape for a loving three-generation family. The house is "old bones with refreshed skin" in many parts of this three-story traditional Four Square and full, multi-room basement. What distinguishes

    Richard Keaveney Cross Street Realtors LLC

    209 N Water St, 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
    • /32

      Est $502,675 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,700 Sq Ft

      311 Mayfair Dr, Chestertown, MD 21620

      311 Mayfair Dr, Chestertown, MD 21620
  • /2

    $12,500 Pending

    • Land
    • 0.50 Acre
    • $25,000 per Acre

    0 Millbrook Dr, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Millbrook 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
    • /13

      Est $226,586 Not Listed For Sale

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

      21286 Maine Ave, Chestertown, MD 21620

      21286 Maine Ave, Chestertown, MD 21620
  • /2

    $399,900 Coming Soon

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft

    10705 Millbrook Dr, Chestertown, MD 21620

    Nestled in the water-access community of Chesapeake Landing, this charming Cape Cod-style home offers a perfect blend of classic character and modern comfort. With over 2,100 square feet of finished living space, the home features four spacious bedrooms and three full bathrooms, ideal for flexible living arrangements. Inside, you’ll find a bright and open layout with beautiful bamboo flooring, a

    Adam Murphy RE/MAX Realty Centre, Inc.

    10705 Millbrook 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
    • /30

      Est $405,611 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
  • /24

    $299,900 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 896 Sq Ft

    21363 Indiana Ave, Chestertown, MD 21620

    Welcome to this low-maintenance coastal cottage in Tolchester, just two blocks from the community beach on the Chesapeake Bay. Set on nearly a half-acre, this home has been completely renovated inside and out.  Inside, you'll find three bedrooms and one and a half baths. Recent upgrades include a new well, new water filtration and softener system, and an encapsulated crawlspace with dehumidifier.

    Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 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
    • /23

      Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,530 Sq Ft

      114 High St, Chestertown, MD 21620

      114 High St, Chestertown, MD 21620

Showing Results 281 - 320, Page 8 of 18

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