112

Homes for Sale in 21620

Section Image Section Image
  • 8276 Broad Neck Rd, Chestertown, MD 21620
    8276 Broad Neck Rd, Chestertown, MD 21620
    /2

    $1,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,383 Sq Ft

    8276 Broad Neck Rd, Chestertown, MD 21620

    Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally well-maintained property offers a rare combination of privacy, space, versatility, and convenience.At the heart of the property is a beautifully maintained brick residence overlooking a picturesque private pond, creating a

    Hayley Norris Select Land & Homes, LLC

    8276 Broad Neck Rd, Chestertown, MD 21620
  • 223 Mount Vernon Ave, Chestertown, MD 21620
    223 Mount Vernon Ave, Chestertown, MD 21620
    /2

    $200,000

    Coming Soon Sep 21
    • 4 Beds
    • 1 Bath
    • 1,816 Sq Ft

    223 Mount Vernon Ave, Chestertown, MD 21620

    Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront.Currently occupied,

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    223 Mount Vernon Ave, Chestertown, MD 21620
  • 104 Lincoln Dr, Chestertown, MD 21620
    104 Lincoln Dr, Chestertown, MD 21620
    104 Lincoln Dr, Chestertown, MD 21620
    /30

    $300,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    104 Lincoln Dr, Chestertown, MD 21620

    This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own.

    Crystal Smith RE/MAX Executive

    104 Lincoln Dr, Chestertown, MD 21620
  • 7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    7482 Poplar Ave, Chestertown, MD 21620
    /40

    $275,000

    • 3 Beds
    • 1 Bath
    • 975 Sq Ft

    7482 Poplar Ave, Chestertown, MD 21620

    Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite

    Lona Todd Taylor Properties

    7482 Poplar Ave, Chestertown, MD 21620
  • 329 Union Church Rd, Chestertown, MD 21620
    329 Union Church Rd, Chestertown, MD 21620
    329 Union Church Rd, Chestertown, MD 21620
    /10

    $568,900

    Coming Soon Sep 28
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    329 Union Church Rd, Chestertown, MD 21620

    Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—a home with plenty of space, useful updates, and room to truly make it your own!Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a

    Heather Dolan Chesapeake Real Estate Associates, LLC

    329 Union Church Rd, Chestertown, MD 21620
  • 0 Towhee Rd, Chesapeake Landing, MD 21620
    0 Towhee Rd, Chesapeake Landing, MD 21620
    /2

    $50,000

    • Land
    • 23,958 Sq Ft
    • $90,909 per Acre

    0 Towhee Rd, Chesapeake Landing, MD 21620

    This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.

    Dustin Parker The Parker Group

    0 Towhee Rd, Chesapeake Landing, MD 21620
  • 217 Edmore Rd, Chestertown, MD 21620
    217 Edmore Rd, Chestertown, MD 21620
    217 Edmore Rd, Chestertown, MD 21620
    /36

    $345,000

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft

    217 Edmore Rd, Chestertown, MD 21620

    Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then.Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings.

    Michele Palmer Doug Ashley Realtors, LLC

    217 Edmore Rd, Chestertown, MD 21620
  • 27942 Old Morgnec Rd, Chestertown, MD 21620
    27942 Old Morgnec Rd, Chestertown, MD 21620
    27942 Old Morgnec Rd, Chestertown, MD 21620
    /4

    $89,000

    • Land
    • 5.17 Acres
    • $17,215 per Acre

    27942 Old Morgnec Rd, Chestertown, MD 21620

    Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

    Brett Davis Gunther-McClary Real Estate

    27942 Old Morgnec Rd, Chestertown, MD 21620
  • 115 Chester Arms Dr, Chestertown, MD 21620
    115 Chester Arms Dr, Chestertown, MD 21620
    /2

    $263,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    115 Chester Arms Dr, Chestertown, MD 21620

    Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own.The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown

    Jarnell Foster Samson Properties

    115 Chester Arms Dr, Chestertown, MD 21620
  • 7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    /23

    $229,000

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    7415 Wilkins Ln, Chestertown, MD 21620

    This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    7415 Wilkins Ln, Chestertown, MD 21620
  • 24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    24775 Langford Rd, Chestertown, MD 21620
    /25

    $315,000

    Coming Soon Sep 18
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    24775 Langford Rd, Chestertown, MD 21620

    Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space.The home

    Joseph A Zang III RE/MAX Chesapeake

    24775 Langford Rd, Chestertown, MD 21620
  • 7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    7464 Shortall St, Chestertown, MD 21620
    /32

    $304,000

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

    7464 Shortall St, Chestertown, MD 21620

    Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy.The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    7464 Shortall St, Chestertown, MD 21620
  • 212 Washington Ave, Chestertown, MD 21620
    212 Washington Ave, Chestertown, MD 21620
    /2

    $675,000

    Open House 10/03 Coming Soon Oct 3
    • 5 Beds
    • 3 Baths
    • 2,838 Sq Ft

    212 Washington Ave, Chestertown, MD 21620

    Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    212 Washington Ave, Chestertown, MD 21620
  • 300 and 302 S Mill St, Chestertown, MD 21620
    300 and 302 S Mill St, Chestertown, MD 21620
    300 and 302 S Mill St, Chestertown, MD 21620
    /17

    $1,195,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    300 and 302 S Mill St, Chestertown, MD 21620

    Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 300 S

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    300 and 302 S Mill St, Chestertown, MD 21620
  • 8184 Rock Hall Rd, Chestertown, MD 21620
    8184 Rock Hall Rd, Chestertown, MD 21620
    8184 Rock Hall Rd, Chestertown, MD 21620
    /38

    $38,200,000

    • 4 Beds
    • 2 Baths
    • 2,330 Sq Ft

    8184 Rock Hall Rd, Chestertown, MD 21620

    Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a

    Joe Hickman Cross Street Realtors LLC

    8184 Rock Hall Rd, Chestertown, MD 21620
  • 101 S College Ave, Chestertown, MD 21620
    101 S College Ave, Chestertown, MD 21620
    101 S College Ave, Chestertown, MD 21620
    /35

    $359,000

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft

    101 S College Ave, Chestertown, MD 21620

    This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space.Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled

    Michele Palmer Doug Ashley Realtors, LLC

    101 S College Ave, Chestertown, MD 21620
  • 22400 Great Oak Landing Rd, Chestertown, MD 21620
    22400 Great Oak Landing Rd, Chestertown, MD 21620
    22400 Great Oak Landing Rd, Chestertown, MD 21620
    /61

    $649,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    22400 Great Oak Landing Rd, Chestertown, MD 21620

    Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    22400 Great Oak Landing Rd, Chestertown, MD 21620
  • 1003 Twin Ct, Chestertown, MD 21620
    1003 Twin Ct, Chestertown, MD 21620
    1003 Twin Ct, Chestertown, MD 21620
    /43

    $499,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,076 Sq Ft

    1003 Twin Ct, Chestertown, MD 21620

    Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and

    Jody Baker Cross Street Realtors LLC

    1003 Twin Ct, 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
    /18

    $295,000

    • 1 Bed
    • 1 Bath

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

    Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 216 Birch Run Rd, Chestertown, MD 21620
    216 Birch Run Rd, Chestertown, MD 21620
    216 Birch Run Rd, Chestertown, MD 21620
    /52

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    216 Birch Run Rd, Chestertown, MD 21620

    Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A

    Liddy Campbell TTR Sotheby's International Realty

    216 Birch Run Rd, Chestertown, MD 21620
  • 124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    124 Wilton Rd, Chestertown, MD 21620
    /23

    $299,900

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

    124 Wilton Rd, Chestertown, MD 21620

    MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis

    Beth Green Doug Ashley Realtors, LLC

    124 Wilton Rd, Chestertown, MD 21620
  • 23208 Buck Neck Rd, Chestertown, MD 21620
    23208 Buck Neck Rd, Chestertown, MD 21620
    23208 Buck Neck Rd, Chestertown, MD 21620
    /35

    $349,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    23208 Buck Neck Rd, Chestertown, MD 21620

    Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price.Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and

    David Moore Real Broker, LLC

    23208 Buck Neck Rd, Chestertown, MD 21620
  • 123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    /45

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    123 Trafford Dr, Chestertown, MD 21620

    Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    123 Trafford Dr, Chestertown, MD 21620
  • 10540 Tonopah Rd, Chestertown, MD 21620
    10540 Tonopah Rd, Chestertown, MD 21620
    10540 Tonopah Rd, Chestertown, MD 21620
    /21

    $269,000

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10540 Tonopah Rd, Chestertown, MD 21620

    Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

    Michele Palmer Doug Ashley Realtors, LLC

    10540 Tonopah Rd, Chestertown, MD 21620
  • 8630 Elm Rd, Chestertown, MD 21620
    8630 Elm Rd, Chestertown, MD 21620
    8630 Elm Rd, Chestertown, MD 21620
    /45

    $424,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    8630 Elm Rd, Chestertown, MD 21620

    Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore.The home offers five generously sized bedrooms, providing comfortable space for family,

    Lawrence Lessin Save 6, Incorporated

    8630 Elm Rd, Chestertown, MD 21620
  • 7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    7982 Radcliffe Rd, Chestertown, MD 21620
    /37

    $455,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft

    7982 Radcliffe Rd, Chestertown, MD 21620

    Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed

    Abigail Usilton Doug Ashley Realtors, LLC

    7982 Radcliffe Rd, Chestertown, MD 21620
  • 0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
    /9

    $450,000

    • Land
    • 12,477 Sq Ft
    • $1,570,925 per Acre

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620

    Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
  • 0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
    /9

    $350,000

    • Land
    • 9,380 Sq Ft
    • $1,625,200 per Acre

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620

    Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops,

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
  • 129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • 620 Cannon St, Chestertown, MD 21620
    620 Cannon St, Chestertown, MD 21620
    620 Cannon St, Chestertown, MD 21620
    /9

    $99,999

    • Land
    • 3,096 Sq Ft
    • $1,406,963 per Acre

    620 Cannon St, Chestertown, MD 21620

    Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available.

    Julie Santoboni Taylor Properties

    620 Cannon St, Chestertown, MD 21620
  • 7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    /68

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,857 Sq Ft

    7828 Country Club Ln, Chestertown, MD 21620

    Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room

    Sarah King Cross Street Realtors LLC

    7828 Country Club Ln, Chestertown, MD 21620
  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    /25

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft

    1010 Twin Ct, Chestertown, MD 21620

    Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • 8999 Orchard Dr, Chestertown, MD 21620
    8999 Orchard Dr, Chestertown, MD 21620
    8999 Orchard Dr, Chestertown, MD 21620
    /74

    $824,900

    • 5 Beds
    • 3.5 Baths
    • 4,353 Sq Ft

    8999 Orchard Dr, Chestertown, MD 21620

    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, MD 21620
  • 201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    201 N Lynchburg St, Chestertown, MD 21620
    /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • 115 Metcalf Rd, Chestertown, MD 21620
    115 Metcalf Rd, Chestertown, MD 21620
    115 Metcalf Rd, Chestertown, MD 21620
    /10

    $259,900

    New Construction Open Thu 6PM - 7PM
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    115 Metcalf Rd, Chestertown, MD 21620

    *Open Every Tuesdy and Thursday from 6 to 7pm*Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously

    David Moore Real Broker, LLC

    115 Metcalf Rd, Chestertown, MD 21620
  • 200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    200 Manor Ave, Chestertown, MD 21620
    /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • 233 Merganser Dr, Chestertown, MD 21620
    233 Merganser Dr, Chestertown, MD 21620
    233 Merganser Dr, Chestertown, MD 21620
    /13

    $60,000

    • Land
    • 21,780 Sq Ft
    • $120,000 per Acre

    233 Merganser Dr, Chestertown, MD 21620

    Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

    Barbara Wallace Long & Foster Real Estate, Inc.

    233 Merganser Dr, Chestertown, MD 21620
  • 121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    *Open Every Tuesday and Thursday from 6 to 7pm*Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • 305 Roosevelt Dr, Chestertown, MD 21620
    305 Roosevelt Dr, Chestertown, MD 21620
    /2

    $60,000

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    305 Roosevelt Dr, Chestertown, MD 21620

    Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

    Agent Photo

    Joe Howerton

    Taylor Properties

    305 Roosevelt Dr, Chestertown, MD 21620
  • 7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    /43

    $885,000

    • 5 Beds
    • 4 Baths
    • 2,639 Sq Ft

    7680 Country Club Ln, Chestertown, MD 21620

    Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    7680 Country Club Ln, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 3

Maryland Kent County Chestertown

Real Estate & Homes for Sale in 21620

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 © 2026 CoStar Group