7,060

Homes in ZIP Code 21620

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  • /53

    $375,000 Sold Apr 16, 2025

    • 3,389 Sq Ft
    • $111/SF
    • 29 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1956

    25740 Collins Ave, Chestertown, MD 21620

    Large Home with Private Pool & Separate Apartment!Nestled in a prime location, this solid, well-maintained home offers breathtaking views of the Chester River Yacht and Country Club Golf Course, creating an inviting and peaceful atmosphere. Originally built in 1956, the character and charm of this property shine through, with a cozy wood stove in the large den, and a welcoming fireplace in the

    Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • /5

      Est $218,572 Not Listed For Sale

      • Studio
      • 1,008 Sq Ft

      327 Pine Tree Rd, Chestertown, MD 21620

      327 Pine Tree Rd, 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
  • /16

    $195,000 Sold Apr 11, 2025

    • 1,350 Sq Ft
    • $144/SF
    • 0 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1955

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620

    This property is in great condition, with a nice kitchen, a living/dining room combo on the main level, a utility room and plenty of storage space. The living room has a slider out to the patio, and there is a storage shed there for outdoor storage. This is an end unit in great condition. Upstairs there are three bedrooms and a full bath. Nice light from windows and indoor lighting.

    Retha Arrabal Doug Ashley Realtors, LLC

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    • /22

      Est $202,008 Not Listed For Sale

      • Studio
      • 1,080 Sq Ft

      340 Pine Tree Rd, Chestertown, MD 21620

      340 Pine Tree Rd, Chestertown, MD 21620
  • /28

    $365,000

    • 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
  • /25

    $385,000 Sold Apr 11, 2025

    • 1,811 Sq Ft
    • $213/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    149 Longfellow Dr, Chestertown, MD 21620

    Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living.Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living space—ideal for a family room, home office, or play area.The

    Isaac Bahary KW Empower

    149 Longfellow Dr, Chestertown, MD 21620
    • /16

      Est $384,098 Not Listed For Sale

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

      206 Tamarack Rd, Chestertown, MD 21620

      206 Tamarack Rd, Chestertown, MD 21620
  • /11

    $103,000

    • Land
    • 0.48 Acre
    • $214,583 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
  • /24

    $359,900 Sold Apr 11, 2025

    • 1,512 Sq Ft
    • $238/SF
    • 67 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2024

    473 Pear Tree Point Rd, Chestertown, MD 21620

    Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting

    David Moore RE/MAX Executive

    473 Pear Tree Point Rd, Chestertown, MD 21620
    • /28

      Est $488,485 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,188 Sq Ft

      118 Hilltop Dr, Chestertown, MD 21620

      118 Hilltop Dr, Chestertown, MD 21620
  • /7

    $75,000

    • Land
    • 2.20 Acres
    • $34,091 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
  • /3

    $553,500 Sold Apr 07, 2025

    • 2,400 Sq Ft
    • $231/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    234 Blakefield Dr, Chestertown, MD 21620

    3 BEDROOM, 2.5 BTHROOM NEW CONSTRUCTION TO START. FINISHED BONUS ROOM. FULL UNFINISHED BASEMENT. APROX 2400 SF.

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
    • /11

      Est $527,875 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,619 Sq Ft

      300 Gatling Dr, Chestertown, MD 21620

      300 Gatling Dr, Chestertown, MD 21620
  • /19

    $3,000,000

    • Land
    • 87 Acres
    • $34,349 per Acre

    0 Cromwell Clark Rd, Chestertown, MD 21620

    Potential for Residential Development!87 Acre land tract that is annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The 44± acres of farmland are surrounded by a forested buffer that may nicely serve the future layout and privacy of a residential community. Site

    BRIAN MORRIS The Land Group

    0 Cromwell Clark Rd, Chestertown, MD 21620
  • /41

    $385,000 Sold Apr 04, 2025

    • 1,560 Sq Ft
    • $247/SF
    • 69 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    109 Secor Rd, Chestertown, MD 21620

    Charming Home in Chester Harbor with Water Access!Welcome to 109 Secor Rd, Chestertown, MD 21620, nestled on a peaceful cul-de-sac in the desirable water-access community of Chester Harbor on the Queen Anne’s side of the Chester River. This home offers a perfect blend of comfort, charm, and recent updates, making it an exceptional choice for your next chapter.Key

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
    • /33

      Est $430,677 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft

      240 Duke of Kent St, Chestertown, MD 21620

      240 Duke of Kent St, Chestertown, MD 21620
  • /95

    $1,550,000

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft

    7961 Quaker Neck Rd, Chestertown, MD 21620

    **Exquisite Waterfront Retreat on Chester River**Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre

    Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
  • /46

    $474,000 Sold Apr 03, 2025

    • 1,900 Sq Ft
    • $249/SF
    • 84 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    220 Blakefield Dr, Chestertown, MD 21620

    Brand New Gorgeous Custom Home completed & ready for a family to start their next adventure. Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island & granite counters, cathedral ceilings, huge family room, 1st floor laundry, front porch, sky-basement on 2nd floor for storage, 2 large bedrooms and full bath on second floor. This great floor plan is hard

    Brenda Fornos Taylor Properties

    220 Blakefield Dr, Chestertown, MD 21620
    • /42

      Est $374,675 Not Listed For Sale

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

      210 Rosin Dr, Chestertown, MD 21620

      210 Rosin Dr, Chestertown, MD 21620
  • /2

    $150,000

    • Land
    • 2.00 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home!Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and the

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • /31

    $305,000 Sold Apr 01, 2025

    • 1,196 Sq Ft
    • $255/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    10640 Watonga Rd, Chestertown, MD 21620

    Located in Chesapeake Landing, this property offers access to a community area with a boat launch and docks, available through membership in the very reasonable community association. The deck overlooks a semi-private backyard. Inside, the house features new carpeting and fresh paint. It offers single-level living with three bedrooms, two full baths, and a kitchen/dining area with a sliding door

    Retha Arrabal Doug Ashley Realtors, LLC

    10640 Watonga Rd, Chestertown, MD 21620
    • /62

      Est $386,857 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      216 Princess Anne Dr, Chestertown, MD 21620

      216 Princess Anne Dr, Chestertown, MD 21620
  • /3

    $15,000

    • Land
    • 0.69 Acre
    • $21,739 per Acre

    23683 L Rd, Chestertown, MD 21620

    This wooded property offers a peaceful, rural setting while still being close to local amenities and waterfront attractions just minutes from the town of Chestertown, Worton Creek Marina, and Great Oak Landing.

    Alyson Anderson Allfirst Realty, Inc.

    23683 L Rd, Chestertown, MD 21620
  • /39

    $355,000 Sold Mar 31, 2025

    • 1,200 Sq Ft
    • $296/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    105 Justin Buch Dr, Chestertown, MD 21620

    Welcome to 105 Justin Buch Drive, a delightful single-family home nestled in a quiet community on the Queen Anne's side of Chestertown, MD. This charming residence offers 3 spacious bedrooms and 2 full bathrooms, providing ample space for comfortable living. Buy with ease with this recently renovated home within the last 3 years, to include a new roof, HVAC, Kitchen backsplash, new garage

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    105 Justin Buch Dr, Chestertown, MD 21620
    • /6

      Est $174,435 Not Listed For Sale

      216 Spring Rd, Millington, MD 21651

      216 Spring Rd, Millington, MD 21651
  • /20

    $220,000

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    300 Hilltop Ln, Chestertown, MD 21620

    Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • /22

    $319,000 Sold Mar 31, 2025

    • 1,188 Sq Ft
    • $269/SF
    • 49 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    201 Fairview Dr, Chestertown, MD 21620

    Welcome to Chester Harbor. Great starter or downsizer, 3 bed 2 bath rancher awaits new owners. The floor plan includes generous Eat -in kitchen and large living room, separate laundry, and a huge screened in porch for picking crabs, parties, or just relaxing. New flooring , fresh paint, and new kitchen counters are a few of the recent updates. Tree lined rear yard and front holly hedge

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    201 Fairview Dr, Chestertown, MD 21620
    • /25

      Est $413,877 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,871 Sq Ft

      306 Rosin Dr, Chestertown, MD 21620

      306 Rosin Dr, Chestertown, MD 21620
  • /2

    $19,000

    • Land
    • 0.34 Acre
    • $55,882 per Acre

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Cogar Rd Unit MDKE2004996, Chestertown, MD 21620
  • /22

    $155,200 Sold Mar 31, 2025

    • Land
    • 1.90 Acres
    • $81,684 per Acre
    • 300 Days On Market

    Lot 4 Muirfield Dr, Chestertown, MD 21620

    Location (3 fairway lots available), Location (minutes from historic Chestertown), Location (easy access to pristine waterways of Maryland s eastern shore). Two other interior lots available including two corner locations. Lot 4 overlooks two greens on on hole #10 the other on # 5 with fairway boarders on two sides. Prestwick offers the best in eastern shore living with the small town charm of

    John Burke Gunther-McClary Real Estate

    Lot 4 Muirfield Dr, Chestertown, MD 21620
    • /8

      Est $1,292,330 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,420 Sq Ft

      545 Fey Rd, Chestertown, MD 21620

      545 Fey Rd, Chestertown, MD 21620
  • /2

    $19,000

    • Land
    • 0.34 Acre
    • $55,882 per Acre

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Michael Bennett Compass

    0 Tonopah Rd Unit MDKE2004994, Chestertown, MD 21620
  • /35

    $365,000 Sold Mar 28, 2025

    • 744 Sq Ft
    • $491/SF
    • 23 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1885

    117 Court St, Chestertown, MD 21620

    Truly fine example of Italianate architecture nestled among Lawyer's Row in Historic District of Chestertown, Maryland. Immerse oneself in the lifestyle of an Historic Eastern Shore Town on the "beautiful" - as so any describe - Chester River. Home of 18th & 19th c. residences, charming shops, strong Arts & Craft Community, live theater and 10th oldest college in America - Washington College.

    Nancy McGuire Maryland Heritage Properties

    117 Court St, Chestertown, MD 21620
    • /18

      Est $345,253 Not Listed For Sale

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

      120 Edmore Rd, Chestertown, MD 21620

      120 Edmore Rd, Chestertown, MD 21620
  • /52

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /28

    $343,600 Sold Mar 26, 2025

    • 1,556 Sq Ft
    • $221/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2000

    249 Duke of Kent St, Chestertown, MD 21620

    Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction soft close drawers, solid butcher block countertops, tile backsplash, large island, brand new stainless steel appliances and much more! eng hardwood flooring, recessed lighting, vertical custom ship lap, gas fireplace, screened

    Lee Wolff FSBO Broker

    249 Duke of Kent St, Chestertown, MD 21620
    • /16

      Est $343,680 Not Listed For Sale

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

      102 Concord Rd, Chestertown, MD 21620

      102 Concord Rd, Chestertown, MD 21620
  • /32

    $49,900

    • Land
    • 1.51 Acres
    • $33,046 per Acre

    0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2004960, Chestertown, MD 21620
  • /41

    $320,000 Sold Mar 26, 2025

    • 1,298 Sq Ft
    • $247/SF
    • 199 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1964

    6744 Church Hill Rd, Chestertown, MD 21620

    Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly resealed driveway accommodates up to 6+ vehicles, with the potential for parking lot expansion, ensuring ample space for guests or clients. The property features two inviting front entries: one through an 8x16 sunporch, ideal for

    Sarah Ulrick Rock Hall Properties Real Estate

    6744 Church Hill Rd, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 18

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