5,853

St Marys, MD Homes

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  • /2

    $35,000

    • Land
    • 0.23 Acre
    • $152,174 per Acre

    36764 Roberto Dr, Bushwood, MD 20618

    Raw Land only - Comes with community amenities, utilize for temporary Rv site with water access, additional lot conveys

    Agent Photo

    Rhonda Darden

    Cooperative Real Estate Maryland, LLC

    (240) 226-3669

    36764 Roberto Dr, Bushwood, MD 20618
  • /20

    $3,300 per month

    • 5 Beds
    • 3 Baths
    • 2,666 Sq Ft
    • House for Rent

    23591 Gunnell Dr, Leonardtown, MD 20650

    Excellent Leonardtown location, close to Saint Mary’s Hospital, easy commute to NAVAIR. This home features five generously sized bedrooms including bedroom and full bath on main level. Traditional colonial floor plan, entry level two story foyer, office/flex room, formal dining room, spacious family room open to kitchen, full bath and that main level bedroom off kitchen as well. Upper level

    Becky King Home Towne Real Estate

    23591 Gunnell Dr, Leonardtown, MD 20650
  • /72

    $449,900 Sold Jul 31, 2025

    • 2,379 Sq Ft
    • $189/SF
    • 12 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    41554 Briarwood Cir, Leonardtown, MD 20650

    Location is key.... Not just in Leonardtown, but in the community itself. Through every window of the rear of this house is the picturesque setting of the wooded tree line and abundant privacy, not often found in Townhome living. This home is tucked back from main road on an open green in front and woods in the rear. Upgrades to this home from original build include: Premium COREtec Pro Plus

    Wayne & Christine Floyd RE/MAX Realty Group

    41554 Briarwood Cir, Leonardtown, MD 20650
    • /3

      Not Listed For Sale

      23104 Upland Dr, Bushwood, MD 20618

      23104 Upland Dr, Bushwood, MD 20618
  • /31

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft

    40534 Miss Ettas Way, Leonardtown, MD 20650

    Welcome home to this beautifully maintained Cape Cod built by Hallmark Homes in 2016, situated on a peaceful 1.98-acre lot! Relax on the inviting front porch and take in the tranquil surroundings. Inside, you'll find a spacious living and dining room combo, perfect for entertaining. The kitchen features granite countertops, stainless steel appliances, and a walk-in pantry—ideal for any home

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 697-2564

    40534 Miss Ettas Way, Leonardtown, MD 20650
  • /15

    $2,350 per month

    • 4 Beds
    • 2.5 Baths
    • 1,380 Sq Ft
    • House for Rent

    39870 Lady Baltimore Ave, Leonardtown, MD 20650

    Charming Rambler in Water-Access Community – Available Now!Enjoy easy one-level living in this adorable 4-bedroom, 2.5-bath rambler nestled in the St. Clements Shores community. With access to St. Clements Bay, you'll love spending time outdoors in the spacious yard with mature trees, a large deck, and peaceful surroundings.Inside, the open-concept layout offers great flow for

    Lesa Clark Redfin Corp

    39870 Lady Baltimore Ave, Leonardtown, MD 20650
  • /50

    $406,000 Sold Jul 25, 2025

    • 984 Sq Ft
    • $413/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    23745 Hicks Dr, Leonardtown, MD 20650

    Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location—all with no HOA.Inside, you’ll find a bright and open layout featuring wide plank flooring, recessed

    Neil Smith Blackwell Real Estate, LLC

    23745 Hicks Dr, Leonardtown, MD 20650
    • /46

      Est $467,234 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,184 Sq Ft

      40077 Big Chestnut Rd, Clements, MD 20624

      40077 Big Chestnut Rd, Clements, MD 20624
  • /96

    $1,300,000

    • 6 Beds
    • 3.5 Baths
    • 5,888 Sq Ft

    23155 Greenstone Dr, 3, Leonardtown, MD 20650

    Luxury, Space, and Sophistication – All in One Remarkable Property! Prepare to be impressed by this meticulously maintained almost 7,000 sq ft estate—a rare gem that blends luxury, comfort, and functionality in every detail. If your current home lacks character or space, this extraordinary residence will exceed all your expectations! Interior Highlights: • Gourmet Kitchen with oversized island,

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 387-9601

    23155 Greenstone Dr, 3, Leonardtown, MD 20650
  • /54

    $3,195 per month

    • 5 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • House for Rent

    38525 Chaptico Rd, Mechanicsville, MD 20659

    Awesome farmhouse located on 3 acre lot. 5 bedrooms 2.5 baths. Large eat in kitchen, dinning room off kitchen, family room/office, living room and 1/2 bath on main level. Upstairs you will find 1 main bedroom with attached full bath and 4 other bedrooms & full bath in the hallway. Fully renovated; new baths, new kitchen cabinets, flooring, new paint throughout, new carpet, new led lighting, new

    William Fitzgerald Fitzgerald Realty & Auctioneers

    38525 Chaptico Rd, Mechanicsville, MD 20659
  • /31

    $750,000 Sold Jul 21, 2025

    • 4,500 Sq Ft
    • $167/SF
    • 3 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 2015

    26248 Tranquility View Ct, Mechanicsville, MD 20659

    Welcome to your dream home in one of the area's most sought-after communities! This beautifully maintained rambler sits on a picturesque 1-acre lot near the end of a quiet cul-de-sac, offering peace, privacy, and room to relax.Inside, you'll find a deluxe kitchen featuring stainless steel appliances, granite countertops, and ample cabinetry—perfect for home chefs and entertaining alike.

    Connie Fitzgerald RE/MAX Closers

    26248 Tranquility View Ct, Mechanicsville, MD 20659
    • /31

      Est $491,470 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,400 Sq Ft

      24220 Victory Ln, Clements, MD 20624

      24220 Victory Ln, Clements, MD 20624
  • /58

    $599,900

    • 6 Beds
    • 4.5 Baths
    • 3,913 Sq Ft

    37978 George F Dr, Mechanicsville, MD 20659

    Two Homes in One on 3 Acres - Perfect for In-Laws or Separate Rental Opportunity!This expansive property offers almost 4,000 sq ft of living space across two homes, making it ideal for multigenerational living or a full separate rental setup. The main house features 4 bedrooms and 3 full baths, with updated paint and flooring throughout. The recently renovated gourmet kitchen boasts newer

    Cynthia Crispell CENTURY 21 New Millennium

    37978 George F Dr, Mechanicsville, MD 20659
  • /40

    $620,000 Sold Jul 17, 2025

    • 3,360 Sq Ft
    • $185/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1995

    25335 Leon Way, Mechanicsville, MD 20659

    This home feels like forever; nestled at the end of a peaceful road, this impeccably maintained 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort, privacy, and nature. Situated on 2.5 acres, the property backs to over 600 acres of farmland. Outside, enjoy approximately 1.5 acres of open yard space, and approximately 1 acre of serene wooded landscape with a peaceful creek, and an

    Deanna Hill Real Broker, LLC

    25335 Leon Way, Mechanicsville, MD 20659
    • /48

      Est $714,949 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,144 Sq Ft

      40271 Laurel Cir, Mechanicsville, MD 20659

      40271 Laurel Cir, Mechanicsville, MD 20659
  • /4

    $19,900

    • Land
    • 1.15 Acres
    • $17,304 per Acre

    40414 Friends Ct, Leonardtown, MD 20650

    Discover the perfect blend of rural charm and modern convenience with this 1.15-acre parcel located in the serene Rural Preservation area of St. Mary’s County. Zoned Agricultural, this versatile property is ideal for a wide range of uses, from building a cozy single-family home or a stylish barndominium to placing a modular or manufactured home, or even starting a small-scale agricultural

    Max Acres

    40414 Friends Ct, Leonardtown, MD 20650
  • /47

    $660,000 Sold Jul 14, 2025

    • 4,306 Sq Ft
    • $153/SF
    • 10 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23278 Applewood Ln, Leonardtown, MD 20650

    Absolutely stunning home in a premier location! Welcome to 23278 Applewood Ln in the sought-after Clark’s Rest community, directly across from the pool, sports courts, and clubhouse! All 4,000 sqft of living space is in pristine condition. From the moment you enter, you will love all of the natural light throughout. The jewel of the home is the expansive kitchen, curated with upgrades for your

    Jonathan Benya EXP Realty, LLC

    23278 Applewood Ln, Leonardtown, MD 20650
    • /65

      Est $665,593 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,310 Sq Ft

      40010 Grandview St, Mechanicsville, MD 20659

      40010 Grandview St, Mechanicsville, MD 20659
  • /30

    $634,999 Open Sat 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft

    41430 Whimsical Ct, Leonardtown, MD 20650

    Price Improvement!!!! Plus $5000 towards buyers closing cost!!! This home is a MUST SEE!!!!Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful

    Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
  • /75

    $595,000 Sold Jul 11, 2025

    • 3,188 Sq Ft
    • $187/SF
    • 29 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2011

    23578 Pine Bluff Way, Leonardtown, MD 20650

    LOCATION...LOCATION...LOCATION! THIS LOVELY HAYDEN MODEL IS NESTLED RIGHT AT THE HEAD OF THE VILLAGE GREEN IN DESIRABLE LEONARD'S GRANT NEIGHBORHOOD. 3 BEDROOMS AND 2 FULL BATHS ON SECOND LEVEL AND A PARTIALLY FINISHED BASEMENT TO INCLUDE REC ROOM AND FULL BATH. UNFINISHED SPACE COULD BE FINISHED FOR THE 4TH BEDROOM OR GREAT STORAGE. OPEN FLOOR PLAN FEATURES HARDWOOD FLOORS, GRANITE

    Jennifer Mullennix CENTURY 21 New Millennium

    23578 Pine Bluff Way, Leonardtown, MD 20650
    • /32

      Est $436,149 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft

      41493 Margrove Cir, Leonardtown, MD 20650

      41493 Margrove Cir, Leonardtown, MD 20650
  • /65

    $649,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    22626 Chickadee Ln, Leonardtown, MD 20650

    Welcome to 22626 Chickadee Lane—an exceptional 4-bedroom, 3.5-bath home nestled on a serene 2-acre lot in the highly sought-after Avenmar neighborhood of Leonardtown. This elegant property offers the perfect blend of privacy, space, and convenience with an open-concept layout that is flooded with natural light and designed for comfortable living and entertaining.Inside, you'll find

    Matthew Burgan Infinitas Realty Group

    22626 Chickadee Ln, Leonardtown, MD 20650
  • /88

    $685,000 Sold Jul 10, 2025

    • 4,267 Sq Ft
    • $161/SF
    • 6 Beds
    • 3.5 Baths
    • Built 2008

    23558 Belmar Dr, Leonardtown, MD 20650

    Beautiful house in the desired neighborhood of Leonard’s Grand in Leonardtown! This house has many unique characteristics! All new carpet! As you walk in to the hardwood entryway, you’ll notice the gorgeous staircase. This level includes a dining room, custom butler’s pantry and a large, upgraded kitchen. The transom windows are gorgeous and bring in a ton of natural light. These cabinets

    Heather Foster RE/MAX One

    23558 Belmar Dr, Leonardtown, MD 20650
    • /72

      Est $669,702 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,980 Sq Ft

      23748 Coventry Dr, Leonardtown, MD 20650

      23748 Coventry Dr, Leonardtown, MD 20650
  • /61

    $595,000 Open Sat 12PM - 3PM

    • 6 Beds
    • 4.5 Baths
    • 3,913 Sq Ft

    37978 George F Dr, Mechanicsville, MD 20659

    Home Sweet Home! This distinctive property features two fully equipped homes under one roof, making it perfect for multigenerational living, a guest house or guaranteed rental income! Great combination of privacy, space and comfort with a serene three acres and NO HOA! Come on inside the main home and enjoy a beautifully upgraded kitchen consisting of custom soft close cabinetry, stainless steel

    Bobby Brown II Five Star Real Estate

    37978 George F Dr, Mechanicsville, MD 20659
  • /43

    $445,000 Sold Jul 08, 2025

    • 1,820 Sq Ft
    • $245/SF
    • 82 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    40905 Knight Rd, Leonardtown, MD 20650

    Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland!This charming home blends comfort and functionality with three spacious bedrooms, 2.5 baths, and a layout that’s perfect for both everyday living and entertaining.Set on a generous half-acre lot, the fully fenced backyard offers plenty of room to enjoy the outdoors. Whether you're hosting a summer barbecue or winding

    Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
    • /71

      Est $713,192 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,262 Sq Ft

      23287 Crestmar Ln, Leonardtown, MD 20650

      23287 Crestmar Ln, Leonardtown, MD 20650
  • /60

    $599,000

    • 4 Beds
    • 3.5 Baths
    • 3,914 Sq Ft

    23650 Rocky Ridge Ct, Leonardtown, MD 20650

    TWO HOUSES FOR THE PRICE OF ONE!** Perfect for a multi-family (in-laws, grown kids) or generating significant rental income. **MAIN HOUSE** offers 2,000 sq ft of single-story living with 3 bedrooms, 2 baths, expansive living & dining areas, hardwood floors, and tons of natural light. Laundry/mud room with a half bath and pantry off the 2-car garage is a bonus. **TWO-STORY GARAGE APARTMENT**

    Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
  • /64

    $1,100,000 Sold Jul 01, 2025

    • 6,508 Sq Ft
    • $169/SF
    • 7 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2009

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650

    Exceptional Private Estate with Detached Efficiency Apartment, Greenhouse, & Extensive Upgrades.Beautifully maintained and thoughtfully updated, this 5 BR, 6.5 BA custom estate offers space, privacy, and versatility in a stunning setting. A long, private farm lane leads to a solar-powered gated entry and professionally landscaped grounds, including wooden and wire fencing designed with

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    • /28

      Est $508,760 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft

      22301 Bayside Rd, Leonardtown, MD 20650

      22301 Bayside Rd, Leonardtown, MD 20650
  • /52

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,296 Sq Ft

    23242 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Clark’s Rest community of Leonardtown! Boasting nearly 3,300 square feet with an open floor plan filled with natural light, this home offers a perfect blend of comfort and functionality.The main level features spacious living and dining areas that flow effortlessly into a modern

    Matthew Burgan Infinitas Realty Group

    23242 Clarks Rest Rd, Leonardtown, MD 20650
  • /78

    $519,000 Sold Jul 01, 2025

    • 2,804 Sq Ft
    • $185/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23433 Grovewood Ct, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest Community. *OPEN HOUSE* Saturday, May 3rd from 11-2.Welcome to this beautifully maintained, "nearly-new" end-unit townhome in the desirable Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views. The chef-inspired kitchen is a dream, showcasing granite countertops, a

    Wayne & Christine Floyd RE/MAX Realty Group

    23433 Grovewood Ct, Leonardtown, MD 20650
    • /30

      Est $768,423 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      40630 Breton Oaks Ln, Leonardtown, MD 20650
  • /80

    $825,000

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft

    39825 Sweetpea Ln, Leonardtown, MD 20650

    Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 feet of water frontage, this 4-bedroom, 3.5-bath home offers peace, privacy, and panoramic views. Inside, you'll find 2,408 square feet of comfortable living space featuring a cozy fireplace, wood stove, and large windows that invite the beauty of the outdoors in. The expansive deck is perfect for entertaining

    Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • /36

    $495,000 Sold Jun 30, 2025

    • 2,124 Sq Ft
    • $233/SF
    • 6 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1994

    25795 Shamrock Ln, Mechanicsville, MD 20659

    Welcome to your dream home nestled on 2 serene acres in a peaceful country neighborhood — Step inside to find a newly renovated kitchen that’s sure to impress — complete with brand-new stainless steel appliances, sleek countertops, and stylish cabinetry. Whether you’re preparing meals for the family or entertaining guests, this kitchen is the heart of the home.The inviting living spaces feature

    Connor Brown Fathom Realty MD, LLC

    25795 Shamrock Ln, Mechanicsville, MD 20659
    • /77

      Est $520,580 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,132 Sq Ft

      23930 Susies Ln, Leonardtown, MD 20650

      23930 Susies Ln, Leonardtown, MD 20650
  • /38

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 3,876 Sq Ft

    23246 Lindsay Dr, Leonardtown, MD 20650

    Welcome to this stunning 5-bedroom, 3.5-bath home located in the desirable Clark’s Rest community! Enjoy peace of mind and long-term savings with fully owned solar panels—no solar panel lease payments—drastically reducing electric bills and increasing your home’s efficiency and value. Additional features include convenient attic access located above the 2-car garage, ideal for extra

    Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
  • /40

    $400,000 Sold Jun 30, 2025

    • 1,556 Sq Ft
    • $257/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    25555 Chaptico Overlook Way, Mechanicsville, MD 20659

    Come take a look at this property nestled in the beautiful countryside! On a 2.5 acre lot, this lovely home has incredible views from its hilltop location. This home is in excellent condition inside and out, move-in ready, and even has newly designed landscaping. It has three bedrooms and two baths. The siding has been recently power-washed, the HVAC system was just serviced, and the ducts were

    Chris Norris JR. Topside Realty

    25555 Chaptico Overlook Way, Mechanicsville, MD 20659
    • /44

      Est $432,586 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft

      23380 Marview Ct, Leonardtown, MD 20650

      23380 Marview Ct, Leonardtown, MD 20650
  • /93

    $689,900

    • 4 Beds
    • 3.5 Baths
    • 4,736 Sq Ft

    39929 Grandview Haven Dr, Mechanicsville, MD 20659

    Welcome home to your 1+ acre piece of paradise in the sought after Grandview Haven! Professionally landscaped, you'll notice the pride in ownership the second you pull in. Side load two car garage. Front porch. Gleaming hardwood flooring, crown & chair molding, and 9' ceilings throughout the main floor. Granite countertops, upgraded refinished 42" cabinetry, & like new stainless steel

    Michael Gray CENTURY 21 New Millennium

    39929 Grandview Haven Dr, Mechanicsville, MD 20659

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