6,895

Chestertown, MD Homes

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    • /5

      Est $217,651 Not Listed For Sale

      • Studio
      • 1,008 Sq Ft

      327 Pine Tree Rd, Chestertown, MD 21620

      327 Pine Tree Rd, Chestertown, MD 21620
  • /20

    $220,000

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

    300 Hilltop Ln, Chestertown, MD 21620

    Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or entertaining.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • /33

    $685,000 Sold Mar 07, 2025

    • 2,512 Sq Ft
    • $273/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    317 Union Church Rd, Chestertown, MD 21620

    Welcome to 317 Union Church Rd, Stunning Custom Built Farmhouse with all the bells and whistles perfectly sited on over 1 acre. Open concept yet defined spaces allow this home to function wonderfully for entertaining and everyday living...The home exudes style and hospitality from its covered wraparound plantation porch through to the welcoming extra wide entry, seamlessly flowing to the

    Karen Clark Clark & Co Realty, LLC

    317 Union Church Rd, Chestertown, MD 21620
    • /22

      Est $201,377 Not Listed For Sale

      • Studio
      • 1,080 Sq Ft

      340 Pine Tree Rd, Chestertown, MD 21620

      340 Pine Tree Rd, Chestertown, MD 21620
  • /2

    $19,000

    • Land
    • 0.34 Acre
    • $55,882 per Acre

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620
  • /21

    $325,000 Sold Mar 06, 2025

    • 2,376 Sq Ft
    • $137/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1969

    10061 Flatland Rd, Chestertown, MD 21620

    Charming, very well-maintained home located just outside historic Chestertown. The side entrance has a spacious deck and ramp that leads to a full blacktop driveway. Unique split level back entrance. 1.3 grassy acres. Large unfinished basement for extra living space. Hardwood flooring beneath the carpet. Updates include recent paint in interior rooms, (except Kitchen), new paint basement,

    Jo Ann Edwards The Hogans Agency

    10061 Flatland Rd, Chestertown, MD 21620
    • /16

      Est $383,260 Not Listed For Sale

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

      206 Tamarack Rd, Chestertown, MD 21620

      206 Tamarack Rd, Chestertown, MD 21620
  • /2

    $19,000

    • Land
    • 0.34 Acre
    • $55,882 per Acre

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620
  • /21

    $165,300 Sold Mar 05, 2025

    • 1,545 Sq Ft
    • $107/SF
    • 129 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1938

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Welcome to this lovely home with a detached garage in the community of Woods Edge in Kent County! The home features three spacious bedrooms with built-in closets, a full bath with dual vanities and a soaking tub, a family room with a fireplace that opens to the kitchen with appliances and wooden cabinets, and a sunroom with tiled floors and a sliding door that leads to the backyard. The home is

    Gina Gargeu Century 21 Downtown

    23110 Old Fairlee Rd, Chestertown, MD 21620
    • /40

      Est $308,862 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft

      310 Central Dr, Chestertown, MD 21620

      310 Central Dr, Chestertown, MD 21620
  • /52

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /35

    $355,675 Sold Feb 28, 2025

    • 1,872 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    10724 Foreston Rd, Chestertown, MD 21620

    Your dream home is waiting! This remodeled home is waiting for you in the serene water-privileged community of Chesapeake Landing, just minutes from downtown Chestertown. The community offers exclusive access to a boat ramp, a small marina with boat slips, picnic area, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience, and

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620
    • /38

      Est $454,039 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,285 Sq Ft

      105 Holly Ct, Chestertown, MD 21620

      105 Holly Ct, Chestertown, MD 21620
  • /22

    $199,900

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    110 Philosophers Terrace, Chestertown, MD 21620

    Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.

    Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
  • /21

    $305,000 Sold Feb 27, 2025

    • 1,028 Sq Ft
    • $297/SF
    • 13 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1976

    116 Fairview Dr, Chestertown, MD 21620

    Move-in ready and waiting for you! Start the new year in this charming 3-bedroom, 1-bath rancher. The brand-new kitchen is a showstopper, featuring sleek granite countertops, stylish new cabinets, and stainless steel appliances. Durable and attractive LVP flooring flows seamlessly throughout the home, creating a low-maintenance living space. Freshly painted from top to bottom, this home feels

    Jody Baker Cross Street Realtors LLC

    116 Fairview Dr, Chestertown, MD 21620
    • /28

      Est $484,401 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,188 Sq Ft

      118 Hilltop Dr, Chestertown, MD 21620

      118 Hilltop Dr, Chestertown, MD 21620
  • /11

    $49,900

    • Land
    • 1.51 Acres
    • $33,046 per Acre

    0 Cloquet Rd Unit MDKE2004960, 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 MDKE2004960, Chestertown, MD 21620
  • /15

    $325,000 Sold Feb 27, 2025

    • 2,460 Sq Ft
    • $132/SF
    • 112 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    117 Primrose Rd, Chestertown, MD 21620

    Ranch home located in Primrose Point neighborhood( Queen Anne's County with Chestertown address), only ten minutes from downtown Chestertown. This home offers large rooms that could be modified to create a formal dining room and seperate family room if desired. The swimming pool has not been used for two years. This property is being sold "AS-IS". Sign posted.

    Herschell Claggett Davis Real Estate, Inc.

    117 Primrose Rd, Chestertown, MD 21620
    • /11

      Est $521,149 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,619 Sq Ft

      300 Gatling Dr, Chestertown, MD 21620

      300 Gatling Dr, Chestertown, MD 21620
  • /26

    $274,000

    • 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
  • /17

    $283,000 Sold Feb 19, 2025

    • 1,840 Sq Ft
    • $154/SF
    • 38 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2003

    104 Oak Leaf Dr, Chestertown, MD 21620

    Welcome to your new home in the vibrant community of Chestertown! This beautiful 3-bedroom, 3.5-bath townhome features an open layout perfect for modern living. The heart of the home is the stylish kitchen, equipped with contemporary finishes and ample storage.Enjoy relaxing in the spacious living area or step outside to your private deck—ideal for entertaining or soaking up the sun. The

    Krystal Zellner Crown Homes Real Estate

    104 Oak Leaf Dr, Chestertown, MD 21620
    • /33

      Est $431,223 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
  • /16

    $232,000

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft

    21217 Texas Ave, Chestertown, MD 21620

    MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • /38

    $389,900 Sold Feb 06, 2025

    • 1,344 Sq Ft
    • $290/SF
    • 40 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2021

    109 Grant Ct, Chestertown, MD 21620

    This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect blend of comfort and modern features. Located in a tranquil setting that backs to farmland, it boasts an open floor plan with cathedral ceilings, creating a spacious and airy atmosphere throughout. The upgraded kitchen with stainless steel appliances that make it ideal for both cooking and entertaining. The

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    109 Grant Ct, Chestertown, MD 21620
    • /68

      Est $1,038,138 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,782 Sq Ft

      408 Pear Tree Point Rd, Chestertown, MD 21620

      408 Pear Tree Point Rd, Chestertown, MD 21620
  • /17

    $349,900

    • 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
  • /29

    $600,000 Sold Feb 06, 2025

    • 2,672 Sq Ft
    • $225/SF
    • 155 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2007

    110 Birch Run Rd, Chestertown, MD 21620

    CUSTOM - BUILT 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome maple flooring throughout the central living

    Paula Ruckelshaus Long & Foster Real Estate, Inc.

    110 Birch Run Rd, Chestertown, MD 21620
    • /42

      Est $378,874 Not Listed For Sale

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

      210 Rosin Dr, Chestertown, MD 21620

      210 Rosin Dr, Chestertown, MD 21620
  • /16

    $449,000

    • Land
    • 2.02 Acres
    • $222,277 per Acre

    0 Walnut Point Rd, Chestertown, MD 21620

    Extremely Rare offering! 2 acre recorded waterfront parcel in Quaker Neck on Walnut Point Road with 211 feet of frontage on the East Fork Of Langford Creek. Parcel was perc evaluated years ago and require re-evaluation which has been applied for, please see documents. Partially wooded and partially cleared with gorgeous views of the Langford Creek. Dock is allowed by the County. Possibility of 4"

    William Norris Select Land & Homes, LLC

    0 Walnut Point Rd, 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
    • /62

      Est $392,526 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
  • /22

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • /24

    $299,900 Sold Jan 31, 2025

    • 1,288 Sq Ft
    • $233/SF
    • 30 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2018

    7500 Shortall St, Chestertown, MD 21620

    This charming 3-bedroom, 2-bath rancher nestled in a serene setting of Quaker Estates is a gem you won't want to miss! This modern 2018 home offers a perfect blend of comfort and style on a back corner lot with scenic trees on two sides. The perfect split bedroom design with large open central living room, kitchen, and dining with generous space perfect for gatherings. Durable vinyl laminate

    Lona Todd Taylor Properties

    7500 Shortall St, Chestertown, MD 21620
    • /25

      Est $415,898 Not Listed For Sale

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

      306 Rosin Dr, Chestertown, MD 21620

      306 Rosin Dr, Chestertown, MD 21620
  • /20

    $299,000

    • Studio
    • 1,224 Sq Ft

    866 Washington Ave, Chestertown, MD 21620

    Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

    Jeff Guthrie Cross Street Realtors LLC

    866 Washington Ave, Chestertown, MD 21620
  • /23

    $379,989 Sold Jan 30, 2025

    • 2,128 Sq Ft
    • $179/SF
    • 56 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1999

    107 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Waterfront with dock and 4-5’ water depth. Enjoy sunsets and western views over the upper Chester River while having the opportunity to crab and fish from your own Dock! 5 bedroom and 3 full baths, sunroom, spacious kitchen with island, and spacious lot. Reasonably priced waterfront under $500,000.00. Great vacation home opportunity! All improvements being sold in "AS-IS" condition.

    William Norris Select Land & Homes, LLC

    107 Char Nor Manor Blvd, Chestertown, MD 21620
    • /16

      Est $342,748 Not Listed For Sale

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

      102 Concord Rd, Chestertown, MD 21620

      102 Concord Rd, Chestertown, MD 21620
  • /6

    $8,000

    • Land
    • 0.42 Acre
    • $19,048 per Acre

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620

    Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek. Lot failed percolation Test in March of 1989.

    Andrew Meikle Doug Ashley Realtors, LLC

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
  • /57

    $427,000 Sold Jan 29, 2025

    • 1,995 Sq Ft
    • $214/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1997

    313 S Queen St, Chestertown, MD 21620

    Amazing opportunity to own a lovely townhouse, located in a row of 6 charming townhomes across from Wilmer Park with water views of the Chester River. No HOA or dues. Walk to restaurants, quaint shops and art galleries downtown or walk over to the Chestertown Marina just a couple of minutes away. Inside you will find an updated kitchen with open access to the dining area and vaulted living

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    313 S Queen St, Chestertown, MD 21620
    • /80

      Est $636,118 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,248 Sq Ft

      118 Westwood Ln, Chestertown, MD 21620

      118 Westwood Ln, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 18

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