6,881

Chestertown, MD Homes

Section Image
    • /17

      Est $209,437 Not Listed For Sale

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

      10484 Cogar Rd, Chestertown, MD 21620

      10484 Cogar Rd, Chestertown, MD 21620
  • /49

    $409,000 Sold May 31, 2024

    • 1,792 Sq Ft
    • $228/SF
    • 1 Day On Market
    • 4 Beds
    • 3 Baths
    • Built 1988

    109 Coleman Dr, Chestertown, MD 21620

    Welcome to your peaceful retreat in the quiet community of Kingstown on the Queen Anne's side of Chestertown! This stick-built rancher by Alton Darling offers a serene setting with its backing to woods and open space, ensuring tranquility and privacy.Step inside to discover one level living that features four bedrooms with two bedrooms with attached private bath for ultimate convenience

    Ken Roderick Chesapeake Real Estate Associates, LLC

    109 Coleman Dr, Chestertown, MD 21620
    • /49

      Est $601,803 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
  • /57

    $525,000 Sold May 31, 2024

    • 2,878 Sq Ft
    • $182/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1993

    207 Pondview Ct, Chestertown, MD 21620

    Welcome to your future haven in the picturesque community of Crestview! Nestled in the heart of Chestertown, this magnificent home at 207 Pondview Ct offers a harmonious blend of natural beauty and modern luxury, creating an unparalleled living experience.Upon arrival, you'll be captivated by the tranquility of the serene community pond that gracefully borders this residence. Imagine

    Ken Roderick Chesapeake Real Estate Associates, LLC

    207 Pondview Ct, Chestertown, MD 21620
    • /20

      Est $419,209 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
  • /21

    $325,000 Sold May 31, 2024

    • 1,248 Sq Ft
    • $260/SF
    • 68 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1978

    112 Pine Chip Rd, Chestertown, MD 21620

    Wonderful neighborhood! The home has a slight Chester River water view from the yard,Dining area and deck. Pictures are from the previous listing before the landscaping was done.The current owner added an accessory building of approx 1000 sq. ft. and a deck. The pool has a rip in the liner, and the repair will be on the buyer. 24-hour notice for appointment

    Mary Fielding Coldwell Banker Chesapeake Real Estate Company

    112 Pine Chip Rd, Chestertown, MD 21620
    • /18

      Est $634,996 Not Listed For Sale

      • Studio
      • 3,114 Sq Ft

      425 High St, Chestertown, MD 21620

      425 High St, Chestertown, MD 21620
  • /36

    $815,000 Sold May 31, 2024

    • 2,200 Sq Ft
    • $370/SF
    • 330 Days On Market
    • 3 Beds
    • 3.5 Baths

    0 Landing Ln Unit 12 MDKE2002644, Chestertown, MD 21620

    Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Chester River. Built with the finest finishes, the main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all

    Kaitlyn Collins Benson & Mangold, LLC

    0 Landing Ln Unit 12 MDKE2002644, 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
  • /37

    $335,000 Sold May 28, 2024

    • 1,344 Sq Ft
    • $249/SF
    • 47 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1990

    9062 Fairlee Rd, Chestertown, MD 21620

    Wow - Major Price Change - Hurry! Enjoy over 3 acres to play, ride 4 wheelers, have horses, chickens & more. Owner has wonderfully updated almost everything about this house and there is home warranty for peace of mind. Relax in the morning on the front porch and watch nature from every window. Gorgeous spacious kitchen with granite counters and including an eat in one that will seat at least

    Brenda Fornos Taylor Properties

    9062 Fairlee Rd, Chestertown, MD 21620
    • /56

      Est $443,561 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

    $395,000 Sold May 23, 2024

    • 1,723 Sq Ft
    • $229/SF
    • 1 Day On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1974

    214 Richard Dr, Chestertown, MD 21620

    Brick Rancher located in the much sought after community Byford Heights. Kitchen was renovated in 2021 after a fire, caused by a microwave malfunction. The roof was also replaced at that time. The furnace was replaced in 2023 and the interior was freshly painted in 2023. The wood floors were refinished in 2024. It is safe to say this home is in move in condition. There is a wood burning

    Doug Ashley Doug Ashley Realtors, LLC

    214 Richard Dr, Chestertown, MD 21620
    • /28

      Est $303,448 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,978 Sq Ft

      10575 Hyala Ct, Chestertown, MD 21620

      10575 Hyala Ct, Chestertown, MD 21620
  • /18

    $299,900 Sold May 23, 2024

    • 1,248 Sq Ft
    • $240/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1994

    10605 Tonopah Rd, Chestertown, MD 21620

    Come by this AWESOME, RENOVATED Rancher in the WATERFRONT Community of Chesapeake Landing is Chestertown. This beautifully renovated single level home is ready for it's new owner today! This home has been carefully renovated in the last few months, including new luxury vinyl plank flooring, new kitchen with white shaker cabinets, granite countertops, new bathrooms, new appliances and much more!

    David Moore RE/MAX Executive

    10605 Tonopah Rd, Chestertown, MD 21620
    • /73

      Est $249,407 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
  • /7

    $30,000 Sold May 23, 2024

    • Land
    • 0.67 Acre
    • $44,776 per Acre
    • 158 Days On Market

    0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620

    Raw land. Building Lot. Mostly wooded. Owner paid for water & sewer allocation, verify with county.

    Vince Raimond Doug Ashley Realtors, LLC

    0 Caulks Field Rd Unit MDKE2003398, Chestertown, MD 21620
    • /32

      Est $229,829 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,534 Sq Ft

      103 Prospect St, Chestertown, MD 21620

      103 Prospect St, Chestertown, MD 21620
  • /8

    $135,000 Sold May 22, 2024

    • 720 Sq Ft
    • $188/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    122 1st St, Chestertown, MD 21620

    This cottage home rests on 3/4 of an acre surrounded by wood and wildlife. Home is in need of complete remodel. Home has hardwood floors, Roof and windows have been replaced. Home is being sold As Is with No Financing Conditions. Located just outside of Chestertown towards Crumpton off of Ewingtown Rd.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    122 1st St, Chestertown, MD 21620
    • /32

      Est $240,767 Not Listed For Sale

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

      8891 Georgetown Rd, Chestertown, MD 21620

      8891 Georgetown Rd, Chestertown, MD 21620
  • /28

    $252,000 Sold May 22, 2024

    • 1,056 Sq Ft
    • $239/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1974

    124 Edmore Rd, Chestertown, MD 21620

    Cute and compact 3 bed, 1 bath rancher in Chester Harbor. Just minutes outside town on the Queen Anne's County side of Chestertown. Fully fenced backyard. Roof is 1 year old. Reverse osmosis system. Queen Anne's County schools. 3rd bedroom was not photographed as seller is storing boxes in that room. Property is being sold as is.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    124 Edmore Rd, Chestertown, MD 21620
    • /24

      Est $280,557 Not Listed For Sale

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

      307 Cedar St, Chestertown, MD 21620

      307 Cedar St, Chestertown, MD 21620
  • /80

    $612,500 Sold May 22, 2024

    • 2,248 Sq Ft
    • $272/SF
    • 39 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    118 Westwood Ln, Chestertown, MD 21620

    Price Reductions!!! This deal just got a good bit sweeter...Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you name it. 15 acres, with small pond and open areas for your animals, sports field, fire pit or huge gardens. Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    118 Westwood Ln, Chestertown, MD 21620
    • /64

      Est $749,918 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,686 Sq Ft

      122 N Queen St, Chestertown, MD 21620

      122 N Queen St, Chestertown, MD 21620
  • /5

    $550,000 Sold May 22, 2024

    • 3,572 Sq Ft
    • $154/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    193 Westwood Ln, Chestertown, MD 21620

    Serene & private, just minutes outside of Chestertown.

    Liddy Campbell TTR Sotheby's International Realty

    193 Westwood Ln, Chestertown, MD 21620
    • /35

      Est $530,334 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
  • /28

    $383,000 Sold May 22, 2024

    • 1,846 Sq Ft
    • $207/SF
    • 67 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    209 Myers Rd, Chestertown, MD 21620

    Don't miss your chance to own this charming rancher located in the sought-after community of The Grove. With over 2000 sq. ft., three bedrooms, two bathrooms, and an open floor plan that bathes the space in natural light, it's a perfect blend of comfort and privacy. Nestled in a sprawling 1.23-acre yard, partially fenced for added privacy, this residence is a haven in a quiet cul-de-sac within

    Joelle Dolch Cross Street Realtors LLC

    209 Myers Rd, Chestertown, MD 21620
    • /57

      Est $719,898 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
  • /68

    $1,700,000 Sold May 17, 2024

    • 4,885 Sq Ft
    • $348/SF
    • 132 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 2006

    22900 Handy Point Rd, Chestertown, MD 21620

    Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or Rock Hall. Enjoy the wildlife, rural setting, and inground pool. Native plants create a very nicely landscaped home. All wall paneling is Western Red Cedar and the wood floors are 150+ years old heart pine. The game room could

    Herschell Claggett Davis Real Estate, Inc.

    22900 Handy Point Rd, Chestertown, MD 21620
    • /45

      Est $405,550 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,676 Sq Ft

      411 Greenwood Ave, Chestertown, MD 21620

      411 Greenwood Ave, Chestertown, MD 21620
  • /64

    $1,725,000 Sold May 15, 2024

    • 2,200 Sq Ft
    • $784/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1986

    9545 Chantilly Farm Ln, Chestertown, MD 21620

    Welcome to your own private paradise nestled upon a picturesque 23.5-acre expanse along the edge of the peaceful Chesapeake Bay. It is here where you can enjoy an abundance of seasonal and local wildlife such as Bald Eagles, ospreys, Canada geese, ducks, bluebirds, turkey, and whitetail deer. There is an ideal blend of tillable and wooded acreage providing for an array of activities including

    William Norris Select Land & Homes, LLC

    9545 Chantilly Farm Ln, Chestertown, MD 21620
    • /45

      Est $492,983 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,824 Sq Ft

      27325 Preston Ln, Chestertown, MD 21620

      27325 Preston Ln, Chestertown, MD 21620
  • /35

    $380,000 Sold May 13, 2024

    • 2,080 Sq Ft
    • $183/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1964

    313 River Rd, Chestertown, MD 21620

    Open House on Saturday, April 13th, 2024 from 11am-1pm!Nestled in the heart of Kingstown's Sarah Skipper Lands development, this charming four-bedroom home in Queen Anne's County, Chestertown offers serene glimpses of the Chester River from its beautifully shaded lot. With spacious room dimensions and a seamless flow, the main level boasts a recently updated kitchen, a large living room

    Liddy Campbell TTR Sotheby's International Realty

    313 River Rd, Chestertown, MD 21620
    • /56

      Est $787,713 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,226 Sq Ft

      117 High St, Chestertown, MD 21620

      117 High St, Chestertown, MD 21620
  • /7

    $265,000 Sold May 10, 2024

    • Land
    • 9 Acres
    • $28,649 per Acre
    • 4 Days On Market

    510 Truslow Rd, Chestertown, MD 21620

    Embrace a piece of history and create your own legacy with this extraordinary opportunity to own 9.2 acres of Truslow Farm—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.Discover this exceptional 9.2-acre parcel,

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    510 Truslow Rd, Chestertown, MD 21620
    • /17

      Est $265,771 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      10355 Bunting Rd, Chestertown, MD 21620

      10355 Bunting Rd, Chestertown, MD 21620
  • /6

    $100,000 Sold May 09, 2024

    • Land
    • 1.09 Acres
    • $91,743 per Acre
    • 5 Days On Market

    0 Gateway Dr, Chestertown, MD 21620

    Beautiful 1 acre cleared land ready to build your dream home. Septic and well locations already approved.Driveway culvert already installed. One half mile from downtown Chestertown with easy access to localshopping. Crestview offers lots of open community space for quiet walks and two ponds for fishing. Theareas behind and to the right of Lot 92 are community space. Your view

    Alex Hodges Cottage Street Realty LLC

    0 Gateway Dr, Chestertown, MD 21620
    • /38

      Est $563,896 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,749 Sq Ft

      225 Richard Dr, Chestertown, MD 21620

      225 Richard Dr, Chestertown, MD 21620
  • /43

    $405,000 Sold May 09, 2024

    • 2,064 Sq Ft
    • $196/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2010

    105 Sutton Way, Chestertown, MD 21620

    Beautifully kept home in Coventry Farm features 4 bedrooms and 2.5 baths. Gleaming hardwood floors throughout the main level. Entering the front door is an office to the right and the formal dining room to the left. Heading down the hall, passing the half bath, enter the large combination living room and kitchen. Sliding doors to the fenced back yard and deck. Living room has a decorative

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    105 Sutton Way, Chestertown, MD 21620
    • /26

      Est $398,855 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,820 Sq Ft

      206 Barroll Dr, Chestertown, MD 21620

      206 Barroll Dr, Chestertown, MD 21620
  • /5

    $145,000 Sold May 08, 2024

    • 1,352 Sq Ft
    • $107/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2007

    24581 Willow Oak Ln, Chestertown, MD 21620

    This fixer upper is a great chance to have a house on a large lot in a prime area just outside of Chestertown. The house itself needs serious renovation and has evidence of smoke/fire damage however has a septic system, well, and great bones. The lot provides 2.4 acres of privacy and tranquility among nature but with the culture and amenities of the town just a short drive away. The property is

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    24581 Willow Oak Ln, Chestertown, MD 21620

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