88

Chestertown, MD Homes for Sale

Section Image Section Image
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    300 Hickory Ln, Chestertown, MD 21620
    /30

    $1,297,000

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    300 Hickory Ln, Chestertown, MD 21620

    Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious ranch-style

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 936-6289

    300 Hickory Ln, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /9

    $90,000

    • Land
    • 3.00 Acres
    • $30,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Call listing agent for more information regarding this offering. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (443) 909-1378

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /63

    $1,550,000

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • 24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    /45

    $310,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    Are you ready to make this lovely well-maintained rancher home yours? It has new HVAC, a new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Three-bedroom, one full bath, large open kitchen/dining and cozy living room. Enjoy time in the large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /41

    $569,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /22

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $759,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /23

    $898,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620
  • 724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    724 Aldora Dr Unit 111, Chestertown, MD 21620
    /38

    $569,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    724 Aldora Dr Unit 111, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury, End of Group, 4 Bedroom Villa with a walk-out lower level. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 883-7905

    724 Aldora Dr Unit 111, Chestertown, MD 21620
  • 7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    7514 Muirfield Dr, Chestertown, MD 21620
    /33

    $797,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    7514 Muirfield Dr, Chestertown, MD 21620

    Beautiful home in a prime location! Prestwick offers ample privacy while only a short distance from Historic District Chestertown and just off of the Chester River Yacht and Country Club's 10th tee. Recently constructed in 2023, the house offers three bedrooms, oak floors throughout, a gourmet kitchen, and ample room for entertaining, all on one floor! The kitchen was completed with stainless

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 206-3727

    7514 Muirfield Dr, Chestertown, MD 21620
  • 728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    728 Aldora Dr Unit 113, Chestertown, MD 21620
    /38

    $519,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    HOME OF THE MONTH -Under ConstructionLuxury 4 Bedroom Villa. The layout is welcoming and very functional. The main level boasts an oversized family room which is open to the kitchen and dining area. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 517-7657

    728 Aldora Dr Unit 113, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /22

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    /35

    $490,000

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

    206 Barroll Dr, Chestertown, MD 21620

    Charming Rancher with Private Backyard Oasis in Byford Estates-Don’t miss your opportunity to own this beautifully maintained ranch-style home tucked within the highly sought-after neighborhood of Byford Estates—just a short stroll to historic downtown Chestertown! With 3 spacious bedrooms, 2 full baths, and multiple living spaces, this property offers comfort, privacy, and the kind of charm

    Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
  • 22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    /73

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    22570 Bay Shore Rd, Chestertown, MD 21620

    Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen /

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
  • 114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    114 Ryan Ct, Chestertown, MD 21620
    /36

    $419,000

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft

    114 Ryan Ct, Chestertown, MD 21620

    Priced over $50,000 below recent appraised value! Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stone’s throw from historic

    Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    /32

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft

    26889 Morgnec Rd, Chestertown, MD 21620

    This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • 5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    5179 Quaker Neck Rd, Chestertown, MD 21620
    /48

    $559,900

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    $20,000 Price Reduction!A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $425,000

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits!Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting.Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from the family’s

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /56

    $845,000

    • 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
  • 11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    11040 Kylie Ln, Chestertown, MD 21620
    /66

    $659,000 Open House 7/12

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $495,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • 7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    /27

    $665,000 Coming Soon

    • 4 Beds
    • 4 Baths
    • 2,544 Sq Ft

    7071 Pomona Rd, Chestertown, MD 21620

    Totaling just over 4 acres together, this double lot opportunity just miles from Chestertown proper has EVERYTHING new that you could possibly need: septic, HVAC & roof in 2021; gourmet kitchen appliance package, windows, exterior doors, BRAND NEW hall bath upstairs, electric upgrades, water heater & conditioner, gutter guards, electric, crawl space work, pest control barrier, Talkie fiber optic

    Liddy Campbell TTR Sotheby's International Realty

    7071 Pomona Rd, Chestertown, MD 21620
  • 10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    /19

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    10624 Millbrook Dr, Chestertown, MD 21620

    Charming One-Level Living Near the Chesapeake Bay!This 3-bedroom, 1-bath home offers comfortable one-level living on a spacious 0.45-acre lot just minutes from downtown Chestertown. With 1,000 sq ft of living space, the home features a bright interior, a walk-in shower, and recent updates including a plastic vapor barrier in the crawl space for peace of mind.Enjoy your mornings on

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    /10

    $175,000

    • 2 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    23069 Raleigh Rd, Chestertown, MD 21620

    Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Roof was replaced in 2022.

    George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
  • 10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    /73

    $399,900

    • 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 freshly painted bright and open layout with beautiful

    Adam Murphy RE/MAX Realty Centre, Inc.

    10705 Millbrook Dr, Chestertown, MD 21620
  • 21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    /31

    $195,000

    • 2 Beds
    • 1 Bath
    • 1,269 Sq Ft

    21317 Persimmon Dr, Chestertown, MD 21620

    Gently used 2 bedroom townhome in sought after Tolchester Village! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms are good sized and have vaulted ceilings! Tolchester Village is a quaint community that underwent a complete renovation in 2021. Public water and sewer! Thoughtfully remodeled and it shows

    Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
  • 925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    /19

    $300,000

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

    925 Round Top Rd, Chestertown, MD 21620

    Welcome to this cute-as-a-button home in the water-access community of Chester Harbor! Whether you're starting out, downsizing, or simply looking to simplify your lifestyle, this move-in ready gem offers the perfect balance of comfort, convenience, and charm. Set on a spacious third of an acre lot, this home offers just the right amount of space—three bedrooms, one full bath, and room to grow

    Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
  • 624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    624 High St, Chestertown, MD 21620
    /3

    $240,000

    • 2 Beds
    • 1 Bath
    • 1,290 Sq Ft

    624 High St, Chestertown, MD 21620

    Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or

    Nicole Stephens Tesla Realty Group, LLC

    624 High St, Chestertown, MD 21620
  • 132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    /10

    $79,900

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    132 Prospect St, Chestertown, MD 21620

    Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

    Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • 9062 Fairlee Rd, Chestertown, MD 21620
    9062 Fairlee Rd, Chestertown, MD 21620
    9062 Fairlee Rd, Chestertown, MD 21620
    /31

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    9062 Fairlee Rd, Chestertown, MD 21620

    ALL BUYERS, PLEASE DO NOT PROCEED DOWN THE PRIVATE DRIVEWAY WITHOUT AN APPOINTMENT! THANK YOU!!Centrally located between historic Chestertown MD and Rock Hall, enjoy this 3.5 acre property to explore, ride 4 wheelers, have horses, chickens & more! Great hunting, lots of deer and wild turkey! 3 bedrooms, 2 full baths in this cute recently updated ranch home. The kitchen is very spacious and has

    Lori Sample EXIT Preferred Realty

    9062 Fairlee Rd, Chestertown, MD 21620
  • 0 Kinglet Rd, Chestertown, MD 21620
    0 Kinglet Rd, Chestertown, MD 21620
    /2

    $12,000

    • Land
    • 0.34 Acre
    • $35,294 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    Recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not buildable. Any reasonable offer considered!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • 26875 Mallard Rd, Chestertown, MD 21620
    26875 Mallard Rd, Chestertown, MD 21620
    26875 Mallard Rd, Chestertown, MD 21620
    /42

    $1,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,789 Sq Ft

    26875 Mallard Rd, Chestertown, MD 21620

    Discover the luxury of coastal living with this masterpiece waterfront property located in a much sought-after location on the Chester River. When entering the home, you’re immediately greeted in the elegant foyer that opens to a formal dining room to the right, and an office to the left that could easily be converted to a first floor bedroom.The fully renovated chef’s kitchen features

    Lynn Hilfiker Gunther-McClary Real Estate

    26875 Mallard Rd, Chestertown, MD 21620
  • 136 Truslow Farm Ln, Chestertown, MD 21620
    136 Truslow Farm Ln, Chestertown, MD 21620
    136 Truslow Farm Ln, Chestertown, MD 21620
    /12

    $575,000

    • Land
    • 3.01 Acres
    • $191,030 per Acre

    136 Truslow Farm Ln, Chestertown, MD 21620

    Don't miss this rare opportunity to own one of the only waterfront lots still available on the Chester River! Perfectly positioned just across the river from the historic charm of Chestertown, this premier property offers front-row access to the area's beloved events, including the Tea Party Festival, Fourth of July celebrations, and the Dickens Festival.Situated in a highly desirable and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    136 Truslow Farm Ln, Chestertown, MD 21620
  • 24607 Chestertown Rd, Chestertown, MD 21620
    24607 Chestertown Rd, Chestertown, MD 21620
    24607 Chestertown Rd, Chestertown, MD 21620
    /28

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,294 Sq Ft

    24607 Chestertown Rd, Chestertown, MD 21620

    Situated on a generous 0.653-acre lot just outside of Chestertown, this property offers the best of both worlds—proximity to town amenities with the added benefit of space and privacy. This well-maintained home features 3 bedrooms and 2.5 bathrooms, including two recently updated baths. The interior boasts a welcoming entryway, formal dining room, and a spacious kitchen equipped with an island,

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    24607 Chestertown Rd, Chestertown, MD 21620
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /11

    $115,000

    • Land
    • 0.48 Acre
    • $239,583 per Acre

    0 East St, Chestertown, MD 21620

    Great chance to purchase a corner lot just across the river from Chestertown's Historic District. Sit and listen to the birds by the pond on this peaceful retreat just minutes from the town's shops, galleries, and waterfront. There aren't many more opportunities like this. Please see the documents for the perc approval and site plan.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 East St, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /7

    $85,000

    • Land
    • 2.20 Acres
    • $38,636 per Acre

    0 Fairlee Rd, Chestertown, MD 21620

    Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land

    Lori Sample EXIT Preferred Realty

    0 Fairlee Rd, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 3

Maryland Chestertown

Real Estate & Homes for Sale in Chestertown, MD

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group