1,028

Homes in ZIP Code 20621

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  • /39

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,326 Sq Ft

    22801 Pleasant Ln, Maddox, MD 20621

    ALMOST like a new build with this completed renovation. New interior walls, new plumbing, new electric, new appliances, new HVAC, new siding, and new floors all in the last year. New floor joists and crawl space moisture barriers. AND one of the highlights is the WATER ACCESS via the community water access point. Its a 3bedroom 2bath, open floor concept, in the Longview Beach Association. Come

    Agent Photo

    Amanda Scott

    Real Broker, LLC

    (240) 693-3429

    22801 Pleasant Ln, Maddox, MD 20621
  • /8

    $1,500 per month

    • 1 Bed
    • 1 Bath
    • 3,002 Sq Ft
    • Condo for Rent

    36548 Notley Hall Rd Unit A, Chaptico, MD 20621

    A charming one-bedroom, one-bathroom apartment in Chaptico, Maryland. This unit features a spacious kitchen, a family room, and ample storage. Located in the heart of St Mary's County. Electric is included in rent. No pets. This is a great place to call home!

    William Fitzgerald Fitzgerald Realty & Auctioneers

    36548 Notley Hall Rd Unit A, Chaptico, MD 20621
  • /19

    $299,900 Sold Jul 08, 2025

    • 1,200 Sq Ft
    • $250/SF
    • 71 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1969

    24338 Longview Rd, Chaptico, MD 20621

    Welcome home to this recently updated home in a super desirable water privileged community! Enjoy all of the waterfront amenities with out the price tag. This home offers you a 3 bedroom 1 bath with a ton of newer updated to include LVP flooring, fresh paint, SS appliances, roof, bathroom with newer vanity, flooring and lighting. With 1200 sqft of finished living space you will have plenty of

    Tina Gray EXP Realty, LLC

    24338 Longview Rd, Chaptico, MD 20621
    • /3

      Not Listed For Sale

      23104 Upland Dr, Bushwood, MD 20618

      23104 Upland Dr, Bushwood, MD 20618
  • /6

    $7,500

    • Land
    • 0.30 Acre
    • $25,000 per Acre

    0 Hughes Ave Unit MDSM2026518, Chaptico, MD 20621

    Great opportunity to own land near Mill Point Shores. New owner would need to verify with St Mary's county for use and options for building. May have access to Mill Point Shores. New owner to verify.

    Jan Kleponis O'Brien Realty ERA Powered

    0 Hughes Ave Unit MDSM2026518, Chaptico, MD 20621
  • /24

    $2,049 per month

    • 2 Beds
    • 1 Bath
    • 754 Sq Ft
    • House for Rent

    36029 Center Ave, Chaptico, MD 20621

    What a cute rental with updated bathroom, fresh paint, new roof, nice appliances, washer and dryer, and nice screened porch for your enjoyment. Nice level yard and a bonus of a large 2 car detached garage. This neighborhood is located in a community which has water access to its community. Looking for a great place to live you have just found it! Lawn service is included with the rent. Owners

    Melanie Montague EXP Realty, LLC

    36029 Center Ave, Chaptico, MD 20621
  • /14

    $265,000 Sold Jun 30, 2025

    • 1,620 Sq Ft
    • $164/SF
    • 149 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1959

    36078 Carver Rd, Chaptico, MD 20621

    Beautiful home in Mill Point Shores Community, St Mary's County MD.Welcome to this beautifully renovated 3-bedroom, 1-bath home, located in the Mill Point Shores community of St. Mary’s County, Maryland. This move-in ready home has been thoughtfully updated with modern amenities and upgrades throughout. In addition to a cozy fireplace, enjoy the comfort and The stunning kitchen has been

    Vicki Alvey RE/MAX One

    36078 Carver Rd, Chaptico, MD 20621
    • /30

      Est $462,444 Not Listed For Sale

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

      36789 Dannys Ln, Chaptico, MD 20621

      36789 Dannys Ln, Chaptico, MD 20621
  • /39

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 2,255 Sq Ft

    36026 Bay Dr, Chaptico, MD 20621

    Seller says SELL! Peaceful Waterfront living in Chaptico Maryland, approximately 6 miles from Mechanicsville Maryland; Carefully laid out in the Millpoint Shores Community, this 3 bedroom, 2.5-bath ranch-style home with Den/Family room and laundry room, is nestled on the banks of the stunning of the Wicomico River. Extending approximately 60ft the home has a private pier with boat lift—perfect

    Marvin Boone Samson Properties

    36026 Bay Dr, Chaptico, MD 20621
  • /2

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • House for Rent

    35972 Washington Ave, Chaptico, MD 20621

    Discover coastal living at its finest! This freshly updated 3-bedroom, 2-bathroom offers modern comfort in a serene, water oriented community just steps from the Wicomico River. Enjoy the best of both worlds: a private retreat with a fenced backyard, paired with exclusive access to community waterfront amenities. Kayak, community beach, picnic, grills and fishing.

    Ebon Jackson EbonAries Realty Group, LLC.

    35972 Washington Ave, Chaptico, MD 20621
  • /35

    $331,700 Sold May 26, 2025

    • 2,536 Sq Ft
    • $131/SF
    • 3 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2010

    23110 Upland Dr, Bushwood, MD 20618

    Welcome to 23110 Upland Drive in charming Bushwood, MD—offering peaceful living with extra space to grow! This well-maintained, one-owner home features 3 bedrooms and 3 full baths, with an impressive utility room providing ample storage. Enjoy outdoor living on the brand-new Trex decks and take advantage of the included adjacent lot for added privacy or future potential. Just a short drive from

    William Rabbitt The Southside Group Real Estate

    23110 Upland Dr, Bushwood, MD 20618
    • /8

      Est $126,500 Not Listed For Sale

      36724 Fielding Dr, Chaptico, MD 20621

      36724 Fielding Dr, Chaptico, MD 20621
  • /7

    $10,000

    • Land
    • 0.25 Acre
    • $40,000 per Acre

    0 Mill Point Rd, 4, Chaptico, MD 20621

    Build your dream home on this lot in Chaptico.

    William Rabbitt The Southside Group Real Estate

    0 Mill Point Rd, 4, Chaptico, MD 20621
  • /5

    $99,000 Sold Mar 20, 2025

    • 1,236 Sq Ft
    • $80/SF
    • 31 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1920

    23690 Maddox Rd, Chaptico, MD 20621

    Situated on a 1-acre lot, this property offers a rare opportunity to create your dream home within its existing footprint. With proper approval from the Saint Mary’s County Health Department and other government organizations, this home can be beautifully remodeled to fit your vision while utilizing the existing well and septic systems. The property boasts a prime location with plenty of

    Darrin Carter RE/MAX One

    23690 Maddox Rd, Chaptico, MD 20621
    • /27

      Est $345,946 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,506 Sq Ft

      23289 Colton Point Rd, Avenue, MD 20609

      23289 Colton Point Rd, Avenue, MD 20609
  • /51

    $270,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    24238 River Dr, Chaptico, MD 20621

    JUST REDUCED! Discover this charming and cozy brick rambler with stunning waterfront views, offering endless potential for both personal enjoyment and investment opportunities. This home presents a unique opportunity for Airbnb or rental income. NOTE: Possible structural damage-buyers are advised to conduct their own inspections. Don't miss this chance to unlock the full potential of this

    Sherietta Dunton The Realty Shoppe LLC

    24238 River Dr, Chaptico, MD 20621
  • /36

    $378,800 Sold Feb 28, 2025

    • 1,352 Sq Ft
    • $280/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    23700 Maddox Rd, Chaptico, MD 20621

    This is the one you are looking for! This cozy rambler is sure to impress. Perched upon a hill with its scenic views of rolling agricultural fields, glistening glimpses of the Wicomico River, and serene wooded privacy to your rear. Starting in 2024 this rambler received a modern facelift with its new metal roof, windows, new paint, appliances, lighting, LVP flooring, carpeted bedrooms and

    Darrin Carter RE/MAX One

    23700 Maddox Rd, Chaptico, MD 20621
    • /59

      Est $588,873 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,538 Sq Ft

      38141 Dons Way, Clements, MD 20624

      38141 Dons Way, Clements, MD 20624
  • /35

    $524,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,953 Sq Ft

    35836 Bay Dr, Mechanicsville, MD 20659

    Waterfront Elegance on the Wicomico River| 3 bed, 2 bath | recently renovated, .045 Acres Direct, Wicomico River Access, Discover the perfect blend of modern luxury and serene riverfront living, Nestled on a peaceful half-acre lot with breathtaking views of the Wicomico River, this meticulously renovated 3 bedroom, 2-bathroom home offers a rare opportunity to own a slice of paradise just moments

    Ebon Jackson EbonAries Realty Group, LLC.

    35836 Bay Dr, Mechanicsville, MD 20659
  • /52

    $549,900 Sold Dec 06, 2024

    • 3,017 Sq Ft
    • $182/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1993

    23565 Mount Chance Ct, Clements, MD 20624

    Nestled at the end of a serene cul-de-sac, this home offers nearly 5 acres of lush, private landscape, making it a perfect retreat from the bustle of everyday life. Surrounded by mature trees, the property boasts an idyllic setting that provides both tranquility and a sense of seclusion. the vast grounds are perfect for outdoor activities, whether it's gardening, hosting barbecues, or simply

    Connie Gunn CENTURY 21 New Millennium

    23565 Mount Chance Ct, Clements, MD 20624
    • /26

      Est $339,967 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,539 Sq Ft

      24148 Hurry Rd, Chaptico, MD 20621

      24148 Hurry Rd, Chaptico, MD 20621
  • /4

    $249,900 Pending

    • Land
    • 40 Acres
    • $6,243 per Acre

    0 Bushwood City Rd Unit MDSM2024670, Chaptico, MD 20621

    EFFECTIVE 5/10/25: NO ADDITIONAL SHOWINGS. BEST AND FINAL OFFERS DUE 4/16/25 AT 5PMA Rare 40-Acre Opportunity in Historic Maddox, Maryland – Untouched, Serene, and Full of PotentialNestled in the heart of Maddox, Maryland, this extraordinary 40-acre parcel offers a once-in-a-generation opportunity to own a truly untouched piece of Southern Maryland's rural heritage. Located in St.

    James Marcum CENTURY 21 New Millennium

    0 Bushwood City Rd Unit MDSM2024670, Chaptico, MD 20621
  • /41

    $335,000 Sold Dec 06, 2024

    • 2,476 Sq Ft
    • $135/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1971

    23060 Upland Dr, Chaptico, MD 20621

    **Charming Renovated Home with Fireplace in Longview Beach, St. Mary's County**Welcome to this beautifully renovated 3-bedroom, 1.5-bath home, located in the peaceful Longview Beach community of St. Mary’s County, Maryland. Nestled on approximately half an acre, this move-in ready home has been thoughtfully updated with modern amenities and upgrades throughout.In addition to a

    LeShawn Rollins Samson Properties

    23060 Upland Dr, Chaptico, MD 20621
    • /16

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 892 Sq Ft

      36681 Owens Rd, Chaptico, MD 20621

      36681 Owens Rd, Chaptico, MD 20621
  • /31

    $235,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 916 Sq Ft

    24385 Macarthur Dr, Maddox, MD 20621

    Attention all First-Time Home Buyers or Buyers looking for 1 Level Living. This charming 2 bedroom, 2 bath rambler sits on a large level 1/2 Acre lot and features a spacious 15x25 deck—perfect for relaxing outdoors. Home has been lovingly maintained and ready for it's new owner. The home offers an open floor plan with a bright living room that has a ceiling fan and large picture window, flowing

    Frank McKnew RE/MAX Realty Group

    24385 Macarthur Dr, Maddox, MD 20621
  • /3

    $450,000 Sold Dec 06, 2024

    • 2,096 Sq Ft
    • $215/SF
    • 3 Beds
    • 2 Baths
    • Built 2013

    36838 Manor Rd, Chaptico, MD 20621

    Welcome to this charming 3-bedroom, 2-bathroom rambler-style home built in 2013, offering a perfect blend of modern convenience and country living. Located in a peaceful setting, this property features a spacious great room designed by Francis Tennyson’s construction company, with the replacement dwelling portion built by Buddy Gibson. Enjoy the comfort and efficiency of the pellet stove

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    36838 Manor Rd, Chaptico, MD 20621
    • /5

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 912 Sq Ft

      22811 Overland, Chaptico, MD 20621

      22811 Overland, Chaptico, MD 20621
  • /40

    $429,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    24215 Thistle Place, Chaptico, MD 20621

    Here's a rare opportunity in Mill Point Shores! BRAND NEW CONSTRUCTION! This custom-built home is ready for its first owners! Enjoy views of the broad Wicomico River from the front porch, under the shade of the pecan tree. Built with your comfort in mind, this home features ceiling fans in nearly every room, with craftsman features, such as the 2-panel round-top interior doors, a custom-finished

    William Matthews RE/MAX One

    24215 Thistle Place, Chaptico, MD 20621
  • /4

    $10,000 Sold Nov 30, 2024

    • Land
    • 0.26 Acre
    • $38,462 per Acre
    • 122 Days On Market

    Lot 58 Bay Dr, Chaptico, MD 20621

    Flat level wooded lot ready for you to build your dream home! This water oriented community offers it all, a clubhouse, beach access and this lot is close to the public boat ramp.

    Lee Hayes RE/MAX Closers

    Lot 58 Bay Dr, Chaptico, MD 20621
    • /8

      Not Listed For Sale

      0 Center Ave Unit MDSM2005632, Chaptico, MD 20621

      0 Center Ave Unit MDSM2005632, Chaptico, MD 20621
  • /2

    $16,000 Under Contract

    • Land
    • 0.25 Acre
    • $64,000 per Acre

    0 Washington Ave Unit MDSM2025414, Chaptico, MD 20621

    Ebon Jackson EbonAries Realty Group, LLC.

    0 Washington Ave Unit MDSM2025414, Chaptico, MD 20621
  • /6

    $200,000 Sold Nov 26, 2024

    • Land
    • 17 Acres
    • $11,547 per Acre
    • 98 Days On Market

    37775 Kinder, Chaptico, MD 20621

    Bring your walking shoes! This beautiful lot is just waiting for your builder to build your dream home! Please call your agent prior to entering property and do not drive onto property. You must use Dynard Road to access property!

    Teresa Dove RE/MAX Realty Group

    37775 Kinder, Chaptico, MD 20621
    • /10

      Not Listed For Sale

      0 Roosevelt Blvd Unit MDSM2009504, Chaptico, MD 20621

      0 Roosevelt Blvd Unit MDSM2009504, Chaptico, MD 20621
  • /2

    $10,000

    • Land
    • 0.23 Acre
    • $43,478 per Acre

    0 Lagoon Dr, Maddox, MD 20621

    ONLINE AUCTION: Bidding begins 09/04/2025 @ 10:00 AM. Bidding ends 09/08/2025 @ 11:30 AM. List Price is Suggested Opening Bid. Deposit: $5,000.Nestled just off Maryland Route 234, this property enjoys easy entry to a major roadway for regional connectivity, including swift westward access toward U.S. 301. Within a short drive lie the Wicomico Shores Golf Course, and the expansive 250-acre

    Adam Shpritz Ashland Auction Group LLC

    0 Lagoon Dr, Maddox, MD 20621
  • /39

    $310,000 Sold Nov 25, 2024

    • 1,792 Sq Ft
    • $173/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2013

    23710 John Walter Ln, Chaptico, MD 20621

    Beautiful Manufactured home that sits on almost 1.5 acres. All rooms are spacious with fresh paint. Please note this home has a new well, new furnace and a new washer and dryer. Great views with privacy. Schedule your showing today!

    Heather Foster RE/MAX One

    23710 John Walter Ln, Chaptico, MD 20621
    • /41

      Est $152,500 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,050 Sq Ft

      22780 Overland Dr, Chaptico, MD 20621

      22780 Overland Dr, Chaptico, MD 20621
  • /3

    $10,000

    • Land
    • 0.33 Acre
    • $30,303 per Acre

    0 Longview Rd, Chaptico, MD 20621

    ONLINE AUCTION: Bidding begins 09/08/2025 @ 10:00 AM. Bidding ends 09/10/2025 @ 11:30 AM. List Price is Suggested Opening Bid. Deposit: $5,000.The parcel 'Lt-32 Longview' sits in a rural residential neighborhood with minimal flood risk, zoned for low-density conservation. Located near the junction of Fairview Drive and Upland Drive, the area offers access to Wicomico Shores Golf Course, a

    Adam Shpritz Ashland Auction Group LLC

    0 Longview Rd, Chaptico, MD 20621
  • /8

    $200,000 Sold Nov 08, 2024

    • Land
    • 15 Acres
    • $13,333 per Acre
    • 81 Days On Market

    37805 Kinder Way, Chaptico, MD 20621

    Bring your walking shoes! This beautiful lot is just waiting for your builder to build your dream home! Please call your agent prior to entering property and do not drive onto property. You must use Dynard Road to access property!

    Teresa Dove RE/MAX Realty Group

    37805 Kinder Way, Chaptico, MD 20621
    • /6

      Not Listed For Sale

      0 Overland Dr Unit MDSM2008958, Maddox, MD 20621

      0 Overland Dr Unit MDSM2008958, Maddox, MD 20621
  • /31

    $250,000 Sold Oct 25, 2024

    • 1,200 Sq Ft
    • $208/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    23136 Upland Dr, Bushwood, MD 20618

    Welcome Home!Discover this charming Brick Rambler offering 3 bedrooms and 2 baths, complete with a 2-car garage. As you enter, you'll be greeted by a spacious living area featuring a bay window and a cozy double-sided wood-burning fireplace, perfect for relaxing on cool evenings. The kitchen boasts tile flooring and sliders leading to the yard, making it a great spot for casual dining and

    Lesa Clark Redfin Corp

    23136 Upland Dr, Bushwood, MD 20618

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