6,895

Chestertown, MD Homes

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  • /33

    $279,900 Sold Jul 09, 2024

    • 1,326 Sq Ft
    • $211/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    10589 Klamath Rd, Chestertown, MD 21620

    Come by this lovely 3 BR Cape Cod in quiet, waterfront community of Chesapeake Landing located just off Worton Creek in beautiful, near historic Chestertown. Large eat-in kitchen area. Traditional dining room or separate home office area. Main floor Primary bedroom with full bathroom. Brand New Roof & gutters 2024. Hot water heater, well pump, appliances and flooring are all new within last 5

    David Moore RE/MAX Executive

    10589 Klamath Rd, Chestertown, MD 21620
    • /18

      Est $481,488 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,260 Sq Ft

      208 Leeds Ct, Chestertown, MD 21620

      208 Leeds Ct, Chestertown, MD 21620
  • /18

    $290,000 Sold Jul 03, 2024

    • 1,056 Sq Ft
    • $275/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1976

    124 Wilton Rd, Chestertown, MD 21620

    MOVE IN READY !!! Charming 3/1 ranch home nestled in a water-oriented community of Chester Harbor. Perfect for those who love being close to the Bay and all it has to offer. This recently updated property boasts modern amenities and a cozy atmosphere, offering the ideal blend of comfort and convenience. Embrace the coastal lifestyle with opportunities for boating,

    Jeff Guthrie Cross Street Realtors LLC

    124 Wilton Rd, Chestertown, MD 21620
    • /35

      Est $401,104 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,181 Sq Ft

      220 N Kent St, Chestertown, MD 21620

      220 N Kent St, Chestertown, MD 21620
  • /18

    $337,600 Sold Jul 01, 2024

    • 1,144 Sq Ft
    • $295/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1986

    120 Edmore Rd, Chestertown, MD 21620

    Welcome to this delightful three bedroom home on the Queen Anne's County side of Chestertown. Located in a friendly neighborhood this home is close to parks, shopping and dining. Charming, comfortable rancher with attached two car garage and many upgrades. A 14X20 back porch with state-of-the-art triple casement windows that you can adjust to three different levels. New items include HVAC,

    Beth Green Doug Ashley Realtors, LLC

    120 Edmore Rd, Chestertown, MD 21620
    • /49

      Est $2,029,761 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,033 Sq Ft

      22600 Fairgale Farm Ln, Chestertown, MD 21620

      22600 Fairgale Farm Ln, Chestertown, MD 21620
  • /24

    $267,250 Sold Jul 01, 2024

    • 2,088 Sq Ft
    • $128/SF
    • 3 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1927

    23795 Lands End Rd, Chestertown, MD 21620

    BRING YOUR BOAT - this gem is located 3/4 Mile to Cliff City's Public Landing. OFFER SUBMISSION DEADLINE - MONDAY, JUNE 3RD AT 12:00 NOON.This country farmhouse, a solid residence constructed in c. 1900 with period details intact, is bordered by lush landscape (both natural and decorative), offers a fenced yard, large shed with electric, whole house Generac Generator... exposed

    Stacy Kendall Cross Street Realtors LLC

    23795 Lands End Rd, Chestertown, MD 21620
    • /54

      Est $409,884 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft

      204 Richard Dr, Chestertown, MD 21620

      204 Richard Dr, Chestertown, MD 21620
  • /7

    $530,000 Sold Jul 01, 2024

    • 3,497 Sq Ft
    • $152/SF
    • 6 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1900

    128 N Queen St, Chestertown, MD 21620

    Price improvement!This building has been converted into 4 apartments. All units are currently rented. Limited interior photos to respect tenant privacy. Landlord pays all utilities. 128 North Queen Street, built in the beautiful Queen Anne style is one of the finest 19th-century houses in the Chestertown Historic District. The house is a block from the Chester River, close to

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    128 N Queen St, Chestertown, MD 21620
    • /4

      Est $347,557 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,356 Sq Ft

      115 School Rd, Chestertown, MD 21620

      115 School Rd, Chestertown, MD 21620
  • /44

    $365,000 Sold Jul 01, 2024

    • 2,045 Sq Ft
    • $178/SF
    • 16 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1976

    208 Byford Dr, Chestertown, MD 21620

    Lovely Cape Cod in desirable Byford Heights. First-floor Primary Bedroom and Bathroom. 2 large bedrooms with full Bathroom on 2nd floor. Beautiful Hardwood floors. Easy flowing floor plan guides you from bright living room to the dining room and then the kitchen. The Kitchen has lots of quality cabinets and space for a kitchen table. The kitchen overlooks the Family Room with Fireplace for cozy

    Mary Fielding Coldwell Banker Chesapeake Real Estate Company

    208 Byford Dr, Chestertown, MD 21620
    • /44

      Est $324,804 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,624 Sq Ft

      10769 Glenola Rd, Chestertown, MD 21620

      10769 Glenola Rd, Chestertown, MD 21620
  • /27

    $320,000 Sold Jul 01, 2024

    • 1,560 Sq Ft
    • $205/SF
    • 20 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    310 Longfellow Dr, Chestertown, MD 21620

    Look no more. This home is cute as a button and packs a ton of recent upgrades. . Starting from the top down: New roof, updated heating, hot water heater, wood flooring, kitchen counters, primary bathroom, encapsulated crawl space. This home is move in ready and has so much to offer. Great floor plan, covered front porch, fenced rear yard ready for pets, gardens, fire pits. The home

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    310 Longfellow Dr, Chestertown, MD 21620
    • /41

      Est $529,725 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,126 Sq Ft

      10181 3rd Point Rd, Chestertown, MD 21620

      10181 3rd Point Rd, Chestertown, MD 21620
  • /22

    $435,000 Sold Jun 28, 2024

    • 2,464 Sq Ft
    • $177/SF
    • 0 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1991

    807 S Meadowview Dr, Chestertown, MD 21620

    Still scheduling showings and would entertain backup offers! Please come and see the home & property! -- This IMPECCABLY maintained home has SO much to offer... main level living, family room, formal living room, home office, FOUR bedrooms, two and a half baths, a HUGE primary suite with a walk-in closet and tiled shower, partial walkout basement, massive back deck with tons of room for a crab

    Liddy Campbell TTR Sotheby's International Realty

    807 S Meadowview Dr, Chestertown, MD 21620
    • /62

      Est $705,105 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,496 Sq Ft

      115 N Queen St, Chestertown, MD 21620

      115 N Queen St, Chestertown, MD 21620
  • /30

    $398,000 Sold Jun 28, 2024

    • 1,854 Sq Ft
    • $215/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    1 Reed Ct, Chestertown, MD 21620

    You are invited to come see this beautiful NEW LISTING in quaint Chestertown located on a lovely corner lot and offering great off-street parking for 4+ cars accessed from a rear entry alley way. This well-maintained split foyer features 3 Bedrooms and 2 Full Baths on the main level and a 4th Bedroom and additional half bath on the lower level. You'll love the quality appointments to include

    Carol Tinnin RE/MAX Leading Edge

    1 Reed Ct, Chestertown, MD 21620
    • /17

      Est $204,417 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      10484 Cogar Rd, Chestertown, MD 21620

      10484 Cogar Rd, Chestertown, MD 21620
  • /8

    $128,000 Sold Jun 28, 2024

    • Land
    • 3.76 Acres
    • $34,043 per Acre
    • 726 Days On Market

    0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620

    Back on the market: Buyer got cold feet the day of settlement. Tranquil countryside parcel perc approved and ready for you to build your dream home. Partially wooded and surrounded by farmland on a quiet road. Just minutes outside Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping,

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Annie Crow Rd Unit MDKE2001556, Chestertown, MD 21620
    • /49

      Est $651,692 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 2,776 Sq Ft

      111 S Mill St, Chestertown, MD 21620

      111 S Mill St, Chestertown, MD 21620
  • /86

    $2,395,000 Sold Jun 27, 2024

    • 3,232 Sq Ft
    • $741/SF
    • 19 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2011

    8974 S Bayview Dr, Chestertown, MD 21620

    Built on a 40-foot bluff overlooking the Chesapeake Bay facing west for nightly sunsets, this is a tour-de-force of design and luxury on the Eastern Shore of Maryland, with truly stunning views from every room. Follow your dreams with this resort-like property as a primary or secondary home. Drive along the maple-lined lighted drive to 1.5 acres of award-winning, irrigated, landscaped grounds

    Richard Keaveney Cross Street Realtors LLC

    8974 S Bayview Dr, Chestertown, MD 21620
    • /20

      Est $431,478 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,705 Sq Ft

      212 Mount Vernon Ave, Chestertown, MD 21620

      212 Mount Vernon Ave, Chestertown, MD 21620
  • /13

    $350,000 Sold Jun 26, 2024

    • 2,153 Sq Ft
    • $163/SF
    • 12 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1952

    7671 Waterview Ln, Chestertown, MD 21620

    Chestertown Rancher in Country Club Estates! This rancher overlooks the golf course with distant water views. Amenities include fireplace, 2 car detached garage, storage building, wood floors, dining room, circular driveway, and laundry room. This is a Fannie Mae Homepath property. Submit all offers on Homepath site. Downtown Chestertown with restaurants and shops is a short drive away.

    Aaron Butler Real Estate Consultants

    7671 Waterview Ln, Chestertown, MD 21620
    • /18

      Est $610,570 Not Listed For Sale

      • Studio
      • 3,114 Sq Ft

      425 High St, Chestertown, MD 21620

      425 High St, Chestertown, MD 21620
  • /28

    $269,975 Sold Jun 26, 2024

    • 1,376 Sq Ft
    • $196/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    106 Pine St, Chestertown, MD 21620

    Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.

    Beth Ostrander Doug Ashley Realtors, LLC

    106 Pine St, Chestertown, MD 21620
    • /2

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 8,190 Sq Ft

      121 Washington Ave, Chestertown, MD 21620

      121 Washington Ave, Chestertown, MD 21620
  • /32

    $345,000 Sold Jun 25, 2024

    • 1,812 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    23530 Clarissa Rd, Chestertown, MD 21620

    Welcome to 23530 Clarissa Road! This well maintained home is established on a beautifully situated lot located within the water access community of Chesapeake Landing. You'll be greeted here by vibrant greens, found flourishing through mature surrounding woods and meticulously cared for landscaping. Find your seat and enjoy peace in nature as an abundance of wildlife can be heard and seen

    Andrew Meikle Doug Ashley Realtors, LLC

    23530 Clarissa Rd, Chestertown, MD 21620
    • /56

      Est $446,322 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,784 Sq Ft

      306 Mayfair Dr, Chestertown, MD 21620

      306 Mayfair Dr, Chestertown, MD 21620
  • /41

    $645,000 Sold Jun 25, 2024

    • 2,866 Sq Ft
    • $225/SF
    • 179 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1900

    106-1 N Water St Unit 1/2, Chestertown, MD 21620

    This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel

    Richard Keaveney Cross Street Realtors LLC

    106-1 N Water St Unit 1/2, Chestertown, MD 21620
    • /73

      Est $258,423 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 2,336 Sq Ft

      22954 Bay Shore Rd, Chestertown, MD 21620

      22954 Bay Shore Rd, Chestertown, MD 21620
  • /32

    $324,000 Sold Jun 21, 2024

    • 1,505 Sq Ft
    • $215/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    22939 Bay Shore Rd, Chestertown, MD 21620

    Welcome to your Eastern Shore haven! This charming property boasts recent updates and in a prime location, offering the perfect blend of modern comfort and public water access to Fairlee Creek & the Chesapeake Bay!Enjoy the 6ft privacy fence that enhances the privacy and security, allowing a safe haven for pets and family or easily store your boat with the double gate entrance. Enjoy the

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    22939 Bay Shore Rd, Chestertown, MD 21620
    • /32

      Est $251,333 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,600 Sq Ft

      8891 Georgetown Rd, Chestertown, MD 21620

      8891 Georgetown Rd, Chestertown, MD 21620
  • /12

    $1,000,000 Sold Jun 21, 2024

    • 2,945 Sq Ft
    • $340/SF
    • 9 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1917

    204 Truslow Farm Ln, Chestertown, MD 21620

    Extraordinary opportunity to purchase the estate of Clorea Truslow—the cherished namesake of Truslow Rd. For generations, this land has been held dear by the Truslow family, and now, for the first time, it is being offered for sale, presenting a once-in-a-lifetime chance to make it your own.Nestled just across the river from the vibrant events of the Sulatana, Downrigging, Tea Party

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    204 Truslow Farm Ln, Chestertown, MD 21620
    • /24

      Est $294,047 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft

      307 Cedar St, Chestertown, MD 21620

      307 Cedar St, Chestertown, MD 21620
  • /7

    $500,000 Sold Jun 21, 2024

    • Land
    • 3.23 Acres
    • $154,799 per Acre
    • 77 Days On Market

    210 Truslow Farm Ln, Chestertown, MD 21620

    Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases, eagerly awaiting your imagination to bring them to life.For years,

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    210 Truslow Farm Ln, Chestertown, MD 21620
    • /35

      Est $531,983 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,301 Sq Ft

      204 Cedar St, Chestertown, MD 21620

      204 Cedar St, Chestertown, MD 21620
  • /2

    $539,000 Sold Jun 16, 2025

    • 3,050 Sq Ft
    • $177/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1879

    107 N Queen St, Chestertown, MD 21620

    The Vannort House stands proudly on historic Queen Street with a colonial-era smokehouse in the yard! Light & breezy: The 31' long screened-in side-porch has doors from the eat-in Kitchen, formal Dining Room, and the grand high-ceilinged Living Room! Keep all the doors open into the screened porch for an amazing indoor-outdoor way of living! A truly versatile layout for entertaining and

    Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
    • /57

      Est $689,137 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,350 Sq Ft

      10230 John Carvill Rd, Chestertown, MD 21620

      10230 John Carvill Rd, Chestertown, MD 21620
  • /2

    $90,000 Sold May 30, 2025

    • Land
    • 13 Acres
    • $6,686 per Acre
    • 0 Days On Market

    0 None Unit MDKE2005014, Chestertown, MD 21620

    13.5 wooded acres with very limited access on north side of Chestertown. Should be excellent deer hunting. 16' paper right of way to access.

    William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
    • /5

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft

      24581 Willow Oak Ln, Chestertown, MD 21620

      24581 Willow Oak Ln, Chestertown, MD 21620

Showing Results 441 - 480, Page 12 of 18

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