7,060

Homes in ZIP Code 21620

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    • /33

      Est $1,074,152 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft

      331 Park Ln, Chestertown, MD 21620

      331 Park Ln, Chestertown, MD 21620
  • /47

    $699,000

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    See your boat from your house! This historic home located at Chestertown marina has been remodeled as recently as 2021. Gorgeous Heartland appliances compliment the hand crafted free-standing cabinetry in the kitchen. A first floor guest suite addition includes a sitting room connected to the house via a mudroom/porch. Above the mudroom is a second story deck that was built to hold a hot tub

    Beth Ostrander Doug Ashley Realtors, LLC

    206 S Water St, Chestertown, MD 21620
  • /8

    $86,000 Sold Jun 09, 2025

    • 973 Sq Ft
    • $88/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1974

    1814 Pondtown Rd, Chestertown, MD 21620

    INVESTOR & BUILDER ALERT! 2.69 Acres | No HOA | Unlock the potential of this prime 2.69-acre property in beautiful Queen Anne’s County! A rare opportunity with no HOA and no restrictions, giving you full creative freedom to bring your vision to life. Whether you're a savvy investor, builder, or contractor looking for your next project, this is the blank canvas you've been waiting for.The existing

    Joelle Dolch Cross Street Realtors LLC

    1814 Pondtown Rd, Chestertown, MD 21620
    • /23

      Est $318,588 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,796 Sq Ft

      228 Dutchess Rd, Chestertown, MD 21620

      228 Dutchess Rd, Chestertown, MD 21620
  • /23

    $495,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    201 Birch Run Rd, Chestertown, MD 21620

    This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • /27

    $280,000 Sold Jun 09, 2025

    • 1,930 Sq Ft
    • $145/SF
    • 164 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    100 Acorn Dr, Chestertown, MD 21620

    Open house! This Saturday, April 19th 11am-1pm. Brand new stainless steel appliances, fresh paint and newly stained deck! Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
    • /11

      Est $302,122 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      102 Darden Rd, Chestertown, MD 21620

      102 Darden Rd, Chestertown, MD 21620
  • /35

    $480,000

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

    206 Barroll Dr, Chestertown, MD 21620

    Charming Rancher with Private Backyard Oasis in Byford Estates206 Barroll Drive, Chestertown, MDLocated in the highly desirable Byford Estates community, this well-maintained rancher offers a rare combination of one-level living, thoughtful layout, and exceptional outdoor space—all within walking distance to historic downtown Chestertown. Enjoy access to festivals, the renowned farmers

    Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
  • /20

    $150,000 Sold Jun 06, 2025

    • 2,240 Sq Ft
    • $67/SF
    • 0 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1921

    508 Cannon St, Chestertown, MD 21620

    Duplex in the Historic District of Chestertown located near the rails to trails.

    Deborah Dawkins Coldwell Banker Realty

    508 Cannon St, Chestertown, MD 21620
    • /27

      Est $343,201 Not Listed For Sale

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

      310 Longfellow Dr, Chestertown, MD 21620

      310 Longfellow Dr, Chestertown, MD 21620
  • /32

    $799,000 Open Sat 2PM - 4PM

    • 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
  • /38

    $575,000 Sold Jun 06, 2025

    • 2,296 Sq Ft
    • $250/SF
    • 19 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1920

    129 N Queen St, Chestertown, MD 21620

    Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

    William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
    • /42

      Est $362,182 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,688 Sq Ft

      414 Pine Tree Rd, Chestertown, MD 21620

      414 Pine Tree 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
  • /4

    $15,000 Sold Jun 02, 2025

    • Land
    • 0.48 Acre
    • $31,250 per Acre
    • 4 Days On Market

    22671 Wood Yard Ln, Chestertown, MD 21620

    Almost half acre of recreational property available between Chestertown and Rock Hall! Best use would be hunting since it is surrounded by woods and farms. There is an existing structure that is a tear down of no value. There appears to be electric run to the property but condition is unknown. The county does not have records of the septic and would need to be perc tested to build on. The back of

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • /8

      Est $183,076 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft

      122 1st St, Chestertown, MD 21620

      122 1st St, 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

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • /37

    $295,000 Sold May 29, 2025

    • 1,272 Sq Ft
    • $232/SF
    • 120 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1973

    23315 Sandpiper Rd, Chestertown, MD 21620

    Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax

    Andrew Meikle Doug Ashley Realtors, LLC

    23315 Sandpiper Rd, Chestertown, MD 21620
    • /33

      Est $287,913 Not Listed For Sale

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

      104 Woodstock Rd, Chestertown, MD 21620

      104 Woodstock Rd, Chestertown, MD 21620
  • /67

    $659,000

    • 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
  • /35

    $510,184 Sold May 29, 2025

    • 2,120 Sq Ft
    • $241/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    716 Aldora Dr, Chestertown, MD 21620

    DECORATED MODELS NOW OPEN Luxury 3 Bedroom Villas The layout is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. 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., and an additional bath for family and

    Terri Hill Builder Solutions Realty

    716 Aldora Dr, Chestertown, MD 21620
    • /36

      Est $491,096 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,848 Sq Ft

      101 Pine Tree Rd, Chestertown, MD 21620

      101 Pine Tree 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
  • /5

    $11,000 Sold May 29, 2025

    • Land
    • 0.34 Acre
    • $32,353 per Acre
    • 371 Days On Market

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Deposit: $5,000. Lot of land located in the Chestertown area of Kent County, MD.JUST MINUTES to the many attractions of the downtown Chestertown area. Easy access to major traffic artery Fairlee Rd. +/- 15,000 SF. Vacant lot of land.

    Adam Shpritz Ashland Auction Group LLC

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    • /18

      Est $302,338 Not Listed For Sale

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

      124 Wilton Rd, Chestertown, MD 21620

      124 Wilton Rd, Chestertown, MD 21620
  • /36

    $399,000 Pending

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

    114 Ryan Ct, Chestertown, MD 21620

    Priced over $70,000 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
  • /40

    $750,000 Sold May 22, 2025

    • 1,682 Sq Ft
    • $446/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1956

    5594 Langford Bay Rd, Chestertown, MD 21620

    Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether you're searching for a quiet second home getaway or a prime income-producing investment, this property offers the waterfront lifestyle so many dream about—boating, fishing, and relaxing right from your own private dock.The heart

    Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, Chestertown, MD 21620
    • /53

      Est $693,052 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 5,366 Sq Ft

      106 Goose Roost Ln, Chestertown, MD 21620

      106 Goose Roost Ln, Chestertown, MD 21620
  • /7

    $470,000 Open House 8/09

    • 4 Beds
    • 3 Baths
    • 3,096 Sq Ft

    201 Boundary Ave, Chestertown, MD 21620

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
  • /27

    $250,000 Sold May 22, 2025

    • 1,248 Sq Ft
    • $200/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    1106 Round Top Rd, Chestertown, MD 21620

    Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in the peaceful surroundings. The home features an unfinished basement, offering potential for extra storage or future living space. With some vision and TLC, this property could shine—whether you're looking to renovate or start

    Clint Evans Cross Street Realtors LLC

    1106 Round Top Rd, Chestertown, MD 21620
    • /32

      Est $366,095 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,345 Sq Ft

      202 Tamarack Rd, Chestertown, MD 21620

      202 Tamarack Rd, Chestertown, MD 21620
  • /73

    $399,900 Under Contract

    • 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
  • /22

    $490,000 Sold May 21, 2025

    • 1,476 Sq Ft
    • $332/SF
    • 14 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1900

    101 S Mill St, Chestertown, MD 21620

    Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
    • /49

      Est $634,227 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,904 Sq Ft

      121 Bass Track Ct, Chestertown, MD 21620

      121 Bass Track Ct, Chestertown, MD 21620
  • /73

    $435,000 Under Contract

    • 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
  • /40

    $600,000 Sold May 16, 2025

    • 2,536 Sq Ft
    • $237/SF
    • 5 Beds
    • 2.5 Baths
    • Built 1920

    108 N Queen St, Chestertown, MD 21620

    Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
    • /28

      Est $289,645 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,240 Sq Ft

      105 Snyder Ln, Chestertown, MD 21620

      105 Snyder Ln, Chestertown, MD 21620
  • /55

    $475,000 Pending

    • 3 Beds
    • 2 Baths
    • 3,280 Sq Ft

    24543 Chestertown Rd, Chestertown, MD 21620

    Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home offers incredible potential for those looking to earn a little sweat equity. This home is ready for a buyer looking to uncover its true potential. Boasting 3 large bedrooms, a very large room on 2nd level could be a bedroom ? game room ? you decide, 3 flexible spaces that can be used as offices, dens, or

    Terri Murray RE/MAX Executive

    24543 Chestertown Rd, Chestertown, MD 21620
  • /32

    $782,500 Sold May 09, 2025

    • 2,204 Sq Ft
    • $355/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    308 Landing Ln, Chestertown, MD 21620

    Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale. The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for

    John Burke Gunther-McClary Real Estate

    308 Landing Ln, Chestertown, MD 21620
    • /33

      Est $717,054 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,327 Sq Ft

      121 Lyons Ln, Chestertown, MD 21620

      121 Lyons Ln, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 18

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