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St Marys County MD Homes for Sale

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  • /29

    $359,777

    • 4 Beds
    • 2 Baths
    • 2,474 Sq Ft

    40743 Magee Dr, Leonardtown, MD 20650

    Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished

    Liam Coonahan Real of Pennsylvania

    40743 Magee Dr, Leonardtown, MD 20650
  • /5

    $335,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    24040 Hollywood Rd, Hollywood, MD 20636

    3BR / 1B Rambler on an acre of land w/garage (storage), Detached carport and outbuildings. Paved driveway just off Hollywood/Leonardtown Road. Hardwood floors throughout Living Room, Hall and bedrooms. Level rear yard bordered by trees. Oil Furnace, water heater, utility sink and washer hook-up are located in the (walk-in) storage area under the home.

    Sheila Milburn Coldwell Banker Premier

    24040 Hollywood Rd, Hollywood, MD 20636
  • /40

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23672 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSandstone Beige Carolina Bead SidingMusket Brown ShuttersBronze Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsWhite Ice Granite CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23672 Weeping Willow Way, Leonardtown, MD 20650
  • /2

    $25,000

    • Land
    • 20,037 Sq Ft
    • $54,348 per Acre

    0 Scott Cir Unit MDSM2032574, Mechanicsville, MD 20659

    Looking for your next spot? This vacant lot is located in the beautiful, water-oriented neighborhood of Golden Beach. Enjoy the ultimate coastal lifestyle in this golf-cart-friendly community with easy access to the water. A rare opportunity to build your dream home exactly the way you want it. Don't let this one slip away!

    Billy Rabbitt The Southside Group Real Estate

    0 Scott Cir Unit MDSM2032574, Mechanicsville, MD 20659
  • /20

    $505,000

    $10K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,004 Sq Ft

    37681 Asher Rd, Mechanicsville, MD 20659

    Welcome to 37681 Asher Road in Mechanicsville, Maryland—a charming and well-maintained property offering comfort, space, and privacy in a peaceful Southern Maryland setting. Situated on a spacious lot, this home provides the perfect balance of quiet country living while still being conveniently located near shopping, dining, and commuter routes.Inside, you’ll find a functional and inviting

    Christopher Carr HomeZu

    37681 Asher Rd, Mechanicsville, MD 20659
  • /9

    $450,000

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    40626 Waterview Dr, Mechanicsville, MD 20659

    Welcome to waterfront living in Golden Beach! This charming 3-bedroom rambler offers comfortable one-level living on nearly half an acre with approximately 75 feet of waterfront. This is a tidal pond and is connected to the Patuxent River but over the years the access to the river has been blocked but the community boat ramp is walking distance from the house. Enjoy peaceful water views and

    Stella Barbour NOVA Brokers, LLC.

    40626 Waterview Dr, Mechanicsville, MD 20659
  • /29

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    20980 Aster Dr, Callaway, MD 20620

    Welcome to 20890 Aster Drive, where privacy, efficiency, and timeless charm come together on more than 4 peaceful acres in the heart of Callaway. This inviting Cape Cod offers the freedom of country living with no HOA, while providing exceptional value through major system upgrades that make homeownership both comfortable and economical. Step inside to discover a light-filled family room with

    Charlotte Long EXP Realty, LLC

    20980 Aster Dr, Callaway, MD 20620
  • /50

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 2,536 Sq Ft

    40220 Golden Beach Rd, Mechanicsville, MD 20659

    Stunning Split-Foyer with Dual Primary Suites & Modern UpdatesWelcome home to this beautifully maintained and thoughtfully updated split-foyer property. Offering 4 bedrooms, 3.5 bathrooms, and an abundance of living space, this home perfectly blends style, comfort, and functionality. Main Level Highlights Bright & Airy Living Space: A large living room welcomes you with dramatic cathedral

    Evelyn Thorne Home Towne Real Estate

    40220 Golden Beach Rd, Mechanicsville, MD 20659
  • /42

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650

    ***** October Delivery *********** Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #139 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space.

    Laura Lee Hefley RE/MAX One

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
  • /31

    $480,000

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,576 Sq Ft

    37580 Asher Rd, Mechanicsville, MD 20659

    A grand double-door entrance welcomes you into the foyer then head up to main level featuring hardwood floors, a spacious living room, a formal dining room perfect for gatherings, and kitchen with ample cabinet space, and room to expand. The main level also includes primary suite with a private bath alongside two additional bedrooms and a hall bath. The expansive lower level features a recreation

    Becky King Home Towne Real Estate

    37580 Asher Rd, Mechanicsville, MD 20659
  • /5

    $614,900

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 3,896 Sq Ft

    44018 W Mervell Ct, Hollywood, MD 20636

    Welcome to refined living in the Estates at Joy Chapel. Thoughtfully designed across 3,974 total square feet, including 3,896 finished square feet, this beautifully appointed five-bedroom, three-and-a-half-bath Colonial offers generous proportions for both elegant entertaining and comfortable everyday living. Fresh interior paint and newly installed carpet add to the home’s polished,

    Robin Errington CENTURY 21 New Millennium

    44018 W Mervell Ct, Hollywood, MD 20636
  • /35

    $599,900

    • 3 Beds
    • 1 Bath
    • 828 Sq Ft

    16101 Piney Point Rd, Piney Point, MD 20674

    Some properties are purchased for the house. Others are purchased for the place. Set on a narrow finger of land between two bodies of water, 16101 Piney Point Road offers an extraordinary waterfront setting with sunrise light on one side and spectacular sunset views on the other. The existing cottage provides an immediate place to enjoy life, watch the sky change, enjoy the water, and begin

    Michelle Camaioni RE/MAX One

    16101 Piney Point Rd, Piney Point, MD 20674
  • /94

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,388 Sq Ft

    25375 Loveville Rd, Leonardtown, MD 20650

    Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2018, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers

    Kandy Moore RMG Realty

    25375 Loveville Rd, Leonardtown, MD 20650
  • /64

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    29724 Marshall Rd, Mechanicsville, MD 20659

    Welcome home to this move-in-ready 4-bedroom, 2.5-bath home in the Golden Beach community. Enjoy the best parts of living in Southern Maryland with access to community amenities including a beach and boat ramp. Inside, you'll find beautiful hardwood flooring throughout the main level, a large kitchen that opens up to the dining area and living room. Upstairs features spacious bedrooms, and plenty

    Jesieryl Hartzer CENTURY 21 New Millennium

    29724 Marshall Rd, Mechanicsville, MD 20659
  • /40

    $579,000

    $20K PRICE DROP
    • 6 Beds
    • 3.5 Baths
    • 4,446 Sq Ft

    45370 Barefoot Dr, California, MD 20619

    Welcome to this stunning, move-in ready 6 bedroom, 3.5 bath home offering over 4,400 square feet of beautifully finished living space in one of the area’s most desirable communities. From the moment you enter the grand foyer, you’re greeted by soaring ceilings, abundant natural light, and an open, flowing layout designed for both comfortable everyday living and entertaining. The impressive

    Chris Norris JR. Topside Realty

    45370 Barefoot Dr, California, MD 20619
  • /77

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /31

    $474,990

    New Construction $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,989 Sq Ft

    44148 Honeysuckle Ln, California, MD 20619

    Barbados Isle Move-in Ready! Private Homesite Backing to trees! Rear Deck, Finished Recreation Room & Basement Bedroom with Full Bathroom, Upgraded Kitchen, & Much More!Plus, receive $10,000 Towards Closing Costs with the use of NVR Mortgage!Schedule a tour today!

    Ryan Homes Builder
    44148 Honeysuckle Ln, California, MD 20619
  • /59

    $399,000

    $1K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    42205 Ridge Rd, Mechanicsville, MD 20659

    Welcome to 42205 Ridge Road in Mechanicsville, a move-in ready Colonial located in the established St. Mary's Beach community.Fully renovated in 2018, this 4 bedroom, 3 full bathroom home offers a comfortable and functional layout. The main level features a welcoming foyer, kitchen and dining area, breakfast nook, crown molding, and a full bathroom. Upstairs, you'll find all four

    Ashley Frazier Five Star Real Estate

    42205 Ridge Rd, Mechanicsville, MD 20659
  • /64

    $700,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown’s most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a fully finished basement, and an expansive backyard designed to be enjoyed.Step inside to a

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • /8

    $550,000

    • Land
    • 5.96 Acres
    • $92,282 per Acre

    0 Mechanicsville Rd Unit MDSM2020678, Mechanicsville, MD 20659

    ****looking for a spot for your new business . . . 5.96 Acres of Commercial property. This was perked in 2010 but is expired. The property has many possibilities. There was a feasibility study done in the past and is now expired. I will be obtaining this information and any other past information and providing it online in the document section. ****ASK ABOUT OWNER FINANCING Available with down

    Stella Barbour NOVA Brokers, LLC.

    0 Mechanicsville Rd Unit MDSM2020678, Mechanicsville, MD 20659
  • /2

    $25,000

    • Land
    • 18,730 Sq Ft
    • $58,140 per Acre

    23253 Maddox Rd, Bushwood, MD 20618

    Build your dream coastal retreat on this beautiful 0.43-acre vacant lot located at 23253 Maddox Road in the desirable, water-oriented community of Bushwood, MD.Positioned in scenic St. Mary’s County, this lot offers the perfect foundation for a custom single-family home or vacation getaway. The critical site prep legwork is already underway—the property is approved for 2 mound septic systems,

    Billy Rabbitt The Southside Group Real Estate

    23253 Maddox Rd, Bushwood, MD 20618
  • /2

    $7,500

    • Land
    • 10,018 Sq Ft
    • $32,609 per Acre

    0 Lagoon Dr, Maddox, MD 20621

    POST AUCTION/BUY NOW: MAKE AN OFFER! Deposit: $5,000 This lot of land is located in Chaptico, MD within St. Mary’s County. The property is in close proximity to Wicomico Shores Golf Course, Christ Episcopal Church, Bachelor's Hope, and Deep Falls. Nestled just off Maryland Route 234, this property enjoys easy entry to a major roadway for regional connectivity, including swift westward access

    Adam Shpritz Ashland Auction Group LLC

    0 Lagoon Dr, Maddox, MD 20621
  • /93

    $1,475,000

    $125K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 4,272 Sq Ft

    23500 River Rd, Lexington Park, MD 20653

    Exceptional waterfront living awaits at 23500 River Road in Town Creek, Maryland. Situated on 1.32 beautifully maintained acres along the Patuxent River, this expansive 3,952 sq. ft. home offers a rare combination of warmth, comfort, functionality, and breathtaking waterfront lifestyle. Designed for both everyday living and entertaining, this 17-room home features four spacious upper-level

    Belinda Taylor EXP Realty, LLC

    23500 River Rd, Lexington Park, MD 20653
  • /3

    $29,900

    • Land
    • 10,454 Sq Ft
    • $124,583 per Acre

    26457 Peninsular Dr, Hollywood, MD 20636

    Vacant parcel around 1/4 acre in size in Hollywood Shores. Call Listing Agent with questions. Photos to be posted soon.

    Gloria Abell Coldwell Banker Premier

    26457 Peninsular Dr, Hollywood, MD 20636
  • /36

    $525,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    37526 River Springs Rd, Avenue, MD 20609

    Priced below tax assessed value, this rare waterfront retreat on beautiful White’s Neck Creek offers a renovated guest house, private dock, and true Southern Maryland charm. Set on over half an acre in the established River Springs waterfront community, 37526 River Springs Road offers the kind of lifestyle buyers wait years to find: peaceful water views, navigable creek access, private outdoor

    Devin Moore Innovation Properties, LLC

    37526 River Springs Rd, Avenue, MD 20609
  • /17

    $750,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    40579 Port Place, Leonardtown, MD 20650

    Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft.Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the

    Carol Kalmus-Choporis Century 21 Redwood Realty

    40579 Port Place, Leonardtown, MD 20650
  • /8

    $200,000

    $50K PRICE DROP
    • Land
    • 1.2 Acres
    • $166,667 per Acre

    0 Saint Johns Rd, Hollywood, MD 20636

    Rare opportunity to own prime land in Hollywood, MD! This vacant, flat, and open parcel sits at the high-visibility intersection of Three Notch Road and St. John’s Road, offering exceptional exposure and accessibility. Public water and sewer are adjacent to the property, creating outstanding development potential. Ideal for a variety of uses—including a farmers market, roadside produce stand,

    John Gatton CENTURY 21 New Millennium

    0 Saint Johns Rd, Hollywood, MD 20636
  • /38

    $739,900

    $110K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,117 Sq Ft

    23680 W Patuxent Beach Rd, California, MD 20619

    Your own dock is your front step to Waterfront Coastal Luxury on the Patuxent: A Waterfront Oasis Offered at: $739,900 Address: 23680 West Patuxent Beach Road Welcome to an unparalleled waterfront lifestyle on the serene shores of the Patuxent River. Nestled on a sprawling 1.88-acre lot in California, Maryland, this magnificent 5-bedroom, 3.5-bathroom retreat masterfully blends modern

    Pete O'Rourke Berkshire Hathaway HomeServices Homesale Realty

    23680 W Patuxent Beach Rd, California, MD 20619
  • /2

    $334,900

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    46538 Majestic Ct, Lexington Park, MD 20653

    This well-maintained rambler-style home features 3 bedrooms and 2 full bathrooms, a spacious living room, an eat-in kitchen with stainless steel appliances, and a cozy family room with a wood-burning stove—perfect for relaxing on cool evenings. Enjoy your morning coffee on the inviting front porch or unwind in the screened rear porch overlooking the backyard. A one-car garage provides additional

    Florentina Killian CENTURY 21 New Millennium

    46538 Majestic Ct, Lexington Park, MD 20653
  • /2

    $90,000

    • Land
    • 8,276 Sq Ft
    • $473,684 per Acre

    20956 Freedom Run Dr, Lexington Park, MD 20653

    Build your dream home on this beautiful 0.1860-acre lot located in the Greenbrier community of Lexington Park. Nestled among well-maintained homes, this property offers the perfect opportunity to create a custom residence in an established neighborhood with public water and sewer available. Conveniently located just minutes from Patuxent River Naval Air Station, shopping, dining, schools, and

    Laura Peruzzi RE/MAX One

    20956 Freedom Run Dr, Lexington Park, MD 20653
  • /6

    $275,000

    • Land
    • 24,829 Sq Ft
    • $482,456 per Acre

    20225 Point Lookout Rd, Great Mills, MD 20634

    Bring your vision to life with this unique opportunity in Great Mills! This offering includes four separate parcels, all zoned commercial—ideal for a wide range of business ventures. Access to public water and sewer. With access on both Route 5 and Flat Iron Road, the property offers exceptional visibility and access in a high-traffic area. Don’t miss the chance to invest in a prime location with

    Billy Rabbitt The Southside Group Real Estate

    20225 Point Lookout Rd, Great Mills, MD 20634
  • /63

    $488,000

    • 3 Beds
    • 3.5 Baths
    • 2,481 Sq Ft

    23230 Colton Point Rd, Avenue, MD 20609

    This beautiful home is back on the market!! The buyer's funding fell through so now's your chance to make this house your home! Beautiful Brick rambler on 1 acre in the sought after area of 7th District. This home has been meticulously cared for and features original hardwood floors that have been restored to their original beauty. The home has 3 bedrooms, two bathrooms, living room, family room,

    Diane Fenwick RE/MAX One

    23230 Colton Point Rd, Avenue, MD 20609
  • /63

    $760,000

    Open Sun 12PM - 3PM
    • 5 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    27075 Widow Ln, Mechanicsville, MD 20659

    Here is your chance! Available for showing starting on 7/31/26! This expansive Cape Cod style home is a once in a lifetime find. Perfect for a farmette or luxurious retreat on 4.51 acres and no HOA. Enjoy a delicious nectarine from one of the many fruit trees while relaxing by your inground pool. The back yard features extensive hardscaping, mature landscaping and a fully fenced in yard. A gas

    Brittany Bahen JPAR Real Estate Professionals

    27075 Widow Ln, Mechanicsville, MD 20659
  • /69

    $925,000

    • 3 Beds
    • 3 Baths
    • 2,304 Sq Ft

    14623 C Way, Scotland, MD 20687

    This well-maintained, three-story Waterfront home on Tanners Creek offers a spacious and versatile layout. Three levels of living space including 3 bedroom 3 bath. The main level features 2 bedrooms, 1 full bathroom, a living room, a kitchen, and a dining area. The upper level includes a primary bedroom with a full bath, while the lower level offers a kitchenette with a large pantry, a family

    Stella Barbour NOVA Brokers, LLC.

    14623 C Way, Scotland, MD 20687
  • /75

    $635,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside.The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • /4

    $100,000

    $150K PRICE DROP

    20910 Olen Mattingly Rd, Avenue, MD 20609

    Rare opportunity in the highly desirable 7th District of St. Mary’s County! This unique offering includes three separate waterfront lots totaling approximately 1.5 acres. Each lot currently contains existing structures that are in dilapidated condition and are likely tear-downs, offering a blank slate for buyers with vision. With its scenic waterfront setting and location in one of the county’s

    Justin Tiede The Southside Group Real Estate

    20910 Olen Mattingly Rd, Avenue, MD 20609
  • /30

    $450,000

    • 3 Beds
    • 2 Baths
    • 2,848 Sq Ft

    28994 Autumnwood Dr, Mechanicsville, MD 20659

    Nestled in the serene community of Big Oak, this exquisite split-level contemporary home offers a perfect blend of comfort and luxury. With three spacious bedrooms and two full bathrooms, this residence is designed to cater to your every need, providing an inviting atmosphere that feels like home from the moment you step inside. As you enter, you are greeted by an open floor plan that seamlessly

    Kathy Lee Suite Samson Properties

    28994 Autumnwood Dr, Mechanicsville, MD 20659
  • /41

    $449,999

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,997 Sq Ft

    23131 Meadow Rd, Bushwood, MD 20618

    Move in today! This brand-new construction home—a stunning masterpiece that seamlessly blends high-end design, functionality and flow with the peace of mind only a new build can provide. From the moment you arrive, the inviting Andersen windows sets the stage for what’s inside: an expansive open-concept main level featuring 9-foot ceilings, recessed lighting, and a cozy gas fireplace. The

    Darrin Carter RE/MAX One

    23131 Meadow Rd, Bushwood, MD 20618
  • /48

    $1,167,000

    • 4 Beds
    • 3 Baths
    • 2,472 Sq Ft

    21485 Canoe Neck Way, Abell, MD 20606

    Bob Tran ExecuHome Realty

    21485 Canoe Neck Way, Abell, MD 20606
  • /48

    $447,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,186 Sq Ft

    48274 Choptank Place, Lexington Park, MD 20653

    Welcome to Choptank Place, a spacious and versatile five bedroom, two and one half bath home nestled on a quiet cul de sac in the heart of Kedges Strait. Ideally located just minutes from Patuxent River Naval Air Station, shopping, dining, schools, and all that St. Mary’s County has to offer, this home combines everyday convenience with an exceptional community lifestyle.Inside, you’ll

    Diana Washabaugh CENTURY 21 New Millennium

    48274 Choptank Place, Lexington Park, MD 20653

Showing Results 81 - 120, Page 3 of 11

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