5,853

St Marys, MD Homes

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  • /80

    $505,000 Sold Jun 30, 2025

    • 2,850 Sq Ft
    • $177/SF
    • 55 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    41572 Briarwood Cir, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest. Welcome to this beautifully maintained, nearly-new end-unit townhome in the sought-after Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views from both the rear and side.Step inside to a spacious main level featuring luxury vinyl plank flooring and a convenient bonus

    Wayne & Christine Floyd RE/MAX Realty Group

    41572 Briarwood Cir, Leonardtown, MD 20650
    • /91

      Est $672,616 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,145 Sq Ft

      41435 Osborne Ln, Leonardtown, MD 20650

      41435 Osborne Ln, Leonardtown, MD 20650
  • /72

    $537,500

    • 4 Beds
    • 2.5 Baths
    • 2,697 Sq Ft

    23674 Jm Gough Ct, Leonardtown, MD 20650

    Welcome home to this beautifully updated Colonial located in a charming and quiet Leonardtown neighborhood—just minutes from local restaurants, shopping, and all the conveniences of town living.Freshly painted throughout and featuring brand-new carpet, this 4-bedroom, 2.5-bath gem is move-in ready and full of modern upgrades. The heart of the home is a gourmet kitchen with upgraded stainless

    Heather Foster RE/MAX One

    23674 Jm Gough Ct, Leonardtown, MD 20650
  • /11

    $340,000 Sold Jun 27, 2025

    • 2,059 Sq Ft
    • $165/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2004

    38897 Viewriver Dr, Bushwood, MD 20618

    Welcome to your dream home! This beautifully maintained rambler features 4 spacious bedrooms and 2 full bathrooms, great for families seeking additional space. The kitchen has been updated with stainless steel appliances and granite countertops. It is located within the Longview Beach community, which is a water access community with features such as a boat ramp, pier, beach, playground,

    Sabrina Reed Coldwell Banker Realty

    38897 Viewriver Dr, Bushwood, MD 20618
    • /27

      Est $642,393 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,400 Sq Ft

      23620 Pine Bluff Way, Leonardtown, MD 20650

      23620 Pine Bluff Way, Leonardtown, MD 20650
  • /67

    $739,900

    • 4 Beds
    • 4 Baths
    • 4,829 Sq Ft

    41535 Fairwood Ct, Leonardtown, MD 20650

    Stunning 4 Bed / 4 Bath Ranch Rambler in Sought-After Clark’s Rest CommunityWelcome to your dream home! Nestled in the highly desirable Clark’s Rest community, this stunning 4-bedroom, 4-bath Ranch Rambler is only one year old and loaded with upgrades with exceptional curb appeal and luxurious features throughout, this is a rare find that won’t last long. This modern home blends comfort,

    Ms. Stephanie M Lee EXP Realty, LLC

    41535 Fairwood Ct, Leonardtown, MD 20650
  • /35

    $725,000 Sold Jun 26, 2025

    • 2,935 Sq Ft
    • $247/SF
    • 0 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2019

    39840 Stillwater Way, Mechanicsville, MD 20659

    Welcome home to this Amazing home with a true southern style wrap around porch and I mean it is a true wrap around porch! From the moment you pull up in the driveway you will want to see more of this home. Nicely situated on a private lot of 3.54 acres, extra parking, beautiful landscaping, firepit area, and a nice shed, and NO HOA. So many great features which make this house a home from the

    Melanie Montague EXP Realty, LLC

    39840 Stillwater Way, Mechanicsville, MD 20659
    • /41

      Est $880,055 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,021 Sq Ft

      23160 Greenstone Dr, Leonardtown, MD 20650

      23160 Greenstone Dr, Leonardtown, MD 20650
  • /79

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality.The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your

    Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • /71

    $485,000 Sold Jun 23, 2025

    • 2,114 Sq Ft
    • $229/SF
    • 2 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1975

    26468 Forest Hall Dr, Mechanicsville, MD 20659

    Peaceful 3-Acre Mechanicsville Retreat with Modern Comfort and Ample Workshop SpaceNestled on a tranquil 3-acre lot in Mechanicsville, this beautifully maintained home offers a rare combination of space, functionality, and convenience—ideal for those who want room to spread out while remaining close to major commuting routes and nearby military bases.As you step inside, you’ll

    Aaron Oelrich OE Realty

    26468 Forest Hall Dr, Mechanicsville, MD 20659
    • /20

      Est $366,777 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft

      28845 Point Lookout Rd, Leonardtown, MD 20650

      28845 Point Lookout Rd, Leonardtown, MD 20650
  • /59

    $640,000

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    Main Level living at its finest in the heart of Leonardtown! Customized Lusby model built in 2020 situated on a spacious corner lot in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which transfers to the new homeowner. VA assumable loan available (to veteran only) at 2.75%. This exquisite home boasts an open floorplan that flows effortlessly. The

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • /61

    $440,000 Sold Jun 16, 2025

    • 2,379 Sq Ft
    • $185/SF
    • 46 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    23445 Grovewood Ct, Leonardtown, MD 20650

    Welcome to 23445 Grovewood Court, an exquisitely maintained residence in the esteemed Clark's Rest community, where sophistication and serenity converge. This splendid 3-bedroom, 3.5-bath townhome offers an elevated living experience, combining impeccable design with unparalleled comfort. Step inside to discover an expansive and luminous open-concept floor plan, enhanced by refined finishes and

    John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
    • /4

      Est $139,909 Not Listed For Sale

      36724 Vaughn Dr, Bushwood, MD 20618

      36724 Vaughn Dr, Bushwood, MD 20618
  • /75

    $784,990

    • 5 Beds
    • 3 Baths
    • 6,064 Sq Ft

    40801 Kiskadee Ln, Leonardtown, MD 20650

    Welcome to 40801 Kiskadee Lane — a truly exceptional residence nestled on over 3 private acres in the prestigious waterfront community of Avenmar. This grand colonial home is an entertainer’s dream, offering over 6,000 square feet of beautifully designed living space, and is specially offered with the last available building lot in the community — an additional 3.5+ acre parcel for $200,000,

    Pattee McInerney Scott McInerney RE/MAX One

    40801 Kiskadee Ln, Leonardtown, MD 20650
  • /79

    $750,000 Sold Jun 12, 2025

    • 4,340 Sq Ft
    • $173/SF
    • 0 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1970

    37710 Chaptico Rd, Mechanicsville, MD 20659

    Designed and built by a student of Frank Lloyd Wright, this Prairie style house integrates perfectly into the surrounding landscape. Upon entering, through the front door, you are greeted with the impressive 8’ brick fireplace and vaulted ceilings of the Great Room. The structural exposed wood beams and mantle over the fireplace were extracted from the decommissioned Mechanicsville post office,

    Christina Price Douglas Realty, LLC

    37710 Chaptico Rd, Mechanicsville, MD 20659
    • /30

      Est $434,345 Not Listed For Sale

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

      36789 Dannys Ln, Chaptico, MD 20621

      36789 Dannys Ln, Chaptico, MD 20621
  • /75

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 2,948 Sq Ft

    22626 Chickadee Ln, Leonardtown, MD 20650

    Welcome to your new home in the lovely Avenmar Community! Upon entering your new home you’re greeted by a stunningly adorned 2 story foyer. As you make your way around the lower level you will find a formal living and dining room with a timeless trim work design. Walking into the kitchen you have an open concept flowing seamlessly into your family room where you will find a gas fireplace to keep

    Dillon Wise JPAR Real Estate Professionals

    22626 Chickadee Ln, Leonardtown, MD 20650
  • /37

    $370,000 Sold Jun 12, 2025

    • 1,200 Sq Ft
    • $308/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    37948 George F Dr, Mechanicsville, MD 20659

    Nestled in the peaceful countryside, this 3-bedroom, 2-bathroom home offers the perfect opportunity to create your ideal rural retreat. Set on a spacious 3-acre lot surrounded by nature, this property is rich with potential for those looking to add their own personal touches.Inside, the home features a traditional layout with generously sized rooms and plenty of natural light. The living area and

    Tina White Real Broker, LLC

    37948 George F Dr, Mechanicsville, MD 20659
    • /8

      Est $126,500 Not Listed For Sale

      36724 Fielding Dr, Chaptico, MD 20621

      36724 Fielding Dr, Chaptico, MD 20621
  • /90

    $630,000

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft

    41402 Silver Charm Ct, Leonardtown, MD 20650

    Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of a community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field. Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches. Freshly painted with

    Kelly Padgett CENTURY 21 New Millennium

    41402 Silver Charm Ct, Leonardtown, MD 20650
  • /41

    $572,000 Sold Jun 09, 2025

    • 3,272 Sq Ft
    • $175/SF
    • 2 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 2004

    23635 Abraham Dr, Leonardtown, MD 20650

    Welcome Home to Comfort, Charm, and SpaceThis stunning Colonial is nestled in a peaceful, sought-after community — the perfect retreat with 6 bedrooms and 4 full baths. Just minutes from downtown Leonardtown, you’ll have easy access to charming shops, popular restaurants, and scenic waterfront views at the Wharf.From the moment you enter, you’ll feel right at home. The warm and inviting family

    Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
    • /7

      Est $152,083 Not Listed For Sale

      23920 Susies Ln, Leonardtown, MD 20650

      23920 Susies Ln, Leonardtown, MD 20650
  • /79

    $649,000

    • 5 Beds
    • 3.5 Baths
    • 4,738 Sq Ft

    23534 Belmar Dr, Leonardtown, MD 20650

    PRICE REDUCED + EXCEPTIONAL FINANCING OPTIONS! Now listed more than $26,000 below the original asking price, 23534 Belmar Drive is your opportunity to own a beautifully maintained, move-in-ready home in the highly sought-after Leonard’s Grant community of Leonardtown. Boasting over 5,000 sq ft of finished living space, this impressive home offers 5 spacious bedrooms, 3.5 baths, and an ideal

    Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
  • /51

    $415,000 Sold Jun 09, 2025

    • 1,348 Sq Ft
    • $308/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new vinyl flooring throughout, the Roof was replaced in 2019, the appliances are less than 2 years old, the Heat Pump was replaced in 2020, and much much more!This home features a huge pantry in the kitchen, a huge laundry room with even more cabinets for storage, a beautiful

    Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    • /35

      Est $538,731 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,920 Sq Ft

      24520 Budds Creek Rd, Clements, MD 20624

      24520 Budds Creek Rd, Clements, MD 20624
  • /36

    $859,900 New Construction

    • 4 Beds
    • 2.5 Baths

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 square feet of luxury living. As you step inside, you are greeted by an open layout that radiates warmth and spaciousness. The heart of the home, a two-story family room with fireplace, is bathed in natural light, creating an inviting atmosphere for entertaining and relaxation. Cook gourmet

    Michele Posey RE/MAX Realty Group

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • /27

    $285,000 Sold Jun 06, 2025

    • 900 Sq Ft
    • $317/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1969

    36786 Wilson Dr, Bushwood, MD 20618

    Welcome to 36786 Wilson Dr. - your completely reimagined haven awaits. Nestled in a peaceful neighborhood, this turnkey home blends modern comforts with move-in readiness. Every major system has been thoughtfully upgraded so you can relax and enjoy. Brand New Kitchen cabinetry, countertops and fixtures and a completely updated bathroom offers buyers the style and function they crave. Beautiful

    Zachary Wyvill RE/MAX United Real Estate

    36786 Wilson Dr, Bushwood, MD 20618
    • /18

      Est $593,648 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,644 Sq Ft

      40725 Fawns Rest Way, Leonardtown, MD 20650

      40725 Fawns Rest Way, Leonardtown, MD 20650
  • /82

    $630,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,252 Sq Ft

    41460 Challedon Way, Leonardtown, MD 20650

    Pride of ownership shines throughout this beautifully maintained Hayden model located in Leonard’s Grant community. From the moment you step inside, you'll be welcomed by neutral paint, beautiful flooring—including gleaming hardwoods, brand-new carpet, and luxury vinyl plank in the finished basement.The gourmet kitchen is truly the heart of the home, featuring updated appliances including a

    Heather Foster RE/MAX One

    41460 Challedon Way, Leonardtown, MD 20650
  • /57

    $759,900 Sold Jun 06, 2025

    • 5,040 Sq Ft
    • $151/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2013

    26132 Harmony View St, Mechanicsville, MD 20659

    Welcome to Your Dream Home in Grandview Haven! One Acre Lot!Step into elegance with a breathtaking two-story foyer adorned by a stunning spiral staircase, and gleaming hardwood floors,—an entrance that instantly feels like home.This spacious 4-bedroom, 3.5-bath residence is loaded with high-end upgrades in the highly sought-after Grandview Haven community. The gourmet kitchen is a true chef’s

    Ms. Stephanie M Lee EXP Realty, LLC

    26132 Harmony View St, Mechanicsville, MD 20659
    • /54

      Est $357,333 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft

      23170 Longview Blvd, Bushwood, MD 20618

      23170 Longview Blvd, Bushwood, MD 20618
  • /79

    $639,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,647 Sq Ft

    41474 Charismatic Way, Leonardtown, MD 20650

    Welcome to 41474 Charismatic Way in the highly sought-after Leonard’s Grant community of Leonardtown, Maryland. This beautifully maintained 5-bedroom, 3.5-bath home offers over 3,600 square feet of finished living space and combines elegance, comfort, and function in every detail. From the charming large front porch to the professionally landscaped yard, the curb appeal is undeniable. Step inside

    Laura Bernth RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
  • /50

    $525,000 Sold Jun 06, 2025

    • 3,024 Sq Ft
    • $174/SF
    • 24 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1990

    37938 George F Dr, Mechanicsville, MD 20659

    Welcome home. This beautiful, well maintained three level large home, strategically placed on over three acres, is tucked away for your quiet enjoyment. From the formal areas to the informal, there is something for everyone. With this home you can entertain guests inside or outside on your deck and/or in the large backyard. The main level circular flow makes it easy for all to move around from

    Stacy Early Long & Foster Real Estate, Inc.

    37938 George F Dr, Mechanicsville, MD 20659
    • /9

      Est $288,259 Not Listed For Sale

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

      23240 Longview Blvd, Bushwood, MD 20618

      23240 Longview Blvd, Bushwood, MD 20618
  • /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
  • /4

    $325,000 Sold Jun 02, 2025

    • 2,310 Sq Ft
    • $141/SF
    • 7 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1975

    26530 Forest Hall Dr, Mechanicsville, MD 20659

    Deeply Discounted two level brick 4 bedroom 3 bath home on 3 acres in highly desirable Helen Estates. Homes in this tight-knit community do not become available frequently so take advantage of this rare opportunity. This property offers privacy and promise, a blank canvas ready for new Owner to bring their vision to life. Home being sold AS-IS, Seller will make no repairs. Passing well and

    Carl Buchheister Save 6, Incorporated

    26530 Forest Hall Dr, Mechanicsville, MD 20659
    • /24

      Est $297,751 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft

      23225 Meadow Rd, Bushwood, MD 20618

      23225 Meadow Rd, Bushwood, MD 20618
  • /66

    $529,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,328 Sq Ft

    22338 White Oak Rd, Leonardtown, MD 20650

    COMING SOON! Beautiful 4 bedroom, 2 1/2 bathroom colonial on over half an acre lot in Breton Bay! This home has has everything you could want with formal living & dining rooms, kitchen w/upgraded counter tops and appliances. The kitchen has bar style seating, a breakfast nook with built in bench and a seating area perfect for morning coffee and enjoying views of the back yard and pool. The

    Kelly Padgett CENTURY 21 New Millennium

    22338 White Oak Rd, Leonardtown, MD 20650
  • /46

    $950,000 Sold Jun 02, 2025

    • 6,762 Sq Ft
    • $140/SF
    • 30 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2001

    22855 White Swan Way, Leonardtown, MD 20650

    Move right in! Tucked away on 3.59 acres, everything has been upgraded. Main level offers stunning hardwood flooring throughout, great room with 2 story ceilings and walls of windows letting nature and light in. Formal living room with custom, built-in bar and formal dining make this an exceptional home for entertaining and large gatherings. Kitchen for the gourmet cook offers natural quartzite

    Barbara Stellway KW Metro Center

    22855 White Swan Way, Leonardtown, MD 20650

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