6,693

St Marys, MD Homes

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  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • 44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    /32

    $2,150 - $2,750 per month

    The Hamptons at Leonardtown

    2 - 3 Beds

    44980 Hamptons Blvd, Leonardtown, MD 20650

    The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • 41554 Briarwood Cir, Leonardtown, MD 20650
    41554 Briarwood Cir, Leonardtown, MD 20650
    41554 Briarwood Cir, 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
    • 41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
      /47

      Est $544,060 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,156 Sq Ft

      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650

      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
  • 40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    /31

    $485,000

    • 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
  • 23591 Gunnell Dr, Leonardtown, MD 20650
    23591 Gunnell Dr, Leonardtown, MD 20650
    23591 Gunnell Dr, Leonardtown, MD 20650
    /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
  • 41997 Loker Ct, Leonardtown, MD 20650
    41997 Loker Ct, Leonardtown, MD 20650
    41997 Loker Ct, Leonardtown, MD 20650
    /41

    $479,900 Sold Jul 31, 2025

    • 2,330 Sq Ft
    • $206/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    41997 Loker Ct, Leonardtown, MD 20650

    Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn

    Jimmy Hayden RE/MAX Realty Group

    41997 Loker Ct, Leonardtown, MD 20650
    • 22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      /36

      Est $441,814 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft

      22605 Calvert St, Leonardtown, MD 20650

      22605 Calvert St, Leonardtown, MD 20650
  • 23080 Town Run Dr, Leonardtown, MD 20650
    23080 Town Run Dr, Leonardtown, MD 20650
    23080 Town Run Dr, Leonardtown, MD 20650
    /88

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 3,794 Sq Ft

    23080 Town Run Dr, Leonardtown, MD 20650

    Welcome to this exceptionally upgraded Quality Built Homes Adelina model in the highly desirable Meadows at Town Run community in Leonardtown, Maryland. Built with nearly every available upgrade, this stunning home offers 5 bedrooms, 3.5 bathrooms, and nearly 3,800 square feet of finished living space, thoughtfully designed for comfort, function, and style.You’ll immediately appreciate

    Laura Bernth RE/MAX One

    23080 Town Run Dr, Leonardtown, MD 20650
  • 41665 Tudor Hall Rd, Leonardtown, MD 20650
    41665 Tudor Hall Rd, Leonardtown, MD 20650
    41665 Tudor Hall Rd, Leonardtown, MD 20650
    /11

    $2,100 per month

    • 4 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • House for Rent

    41665 Tudor Hall Rd, Leonardtown, MD 20650

    Please fill out application And make sure to include all tenants who are 18 and older also For an application fee.

    41665 Tudor Hall Rd, Leonardtown, MD 20650
  • 23745 Hicks Dr, Leonardtown, MD 20650
    23745 Hicks Dr, Leonardtown, MD 20650
    23745 Hicks Dr, 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
    • 41493 Margrove Cir, Leonardtown, MD 20650
      41493 Margrove Cir, Leonardtown, MD 20650
      41493 Margrove Cir, Leonardtown, MD 20650
      /32

      Est $439,003 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
  • 22542 Landing Way, Leonardtown, MD 20650
    22542 Landing Way, Leonardtown, MD 20650
    22542 Landing Way, Leonardtown, MD 20650
    /42

    $530,000

    • 3 Beds
    • 3.5 Baths
    • 2,752 Sq Ft

    22542 Landing Way, Leonardtown, MD 20650

    End Unit Townhome with Coastal Charm & Waterfront LivinEnd Unit Townhome with Coastal Charm & Waterfront Living This stunning 3-story end-unit townhome blends spacious living with coastal serenity in a picturesque waterfront community on Breton Bay. Just a short stroll from Leonardtown Square, you’ll enjoy easy access to shops, dining, and festive community events at the

    Trish Brow EXP Realty, LLC

    22542 Landing Way, Leonardtown, MD 20650
  • 22425 Point Lookout Rd, Leonardtown, MD 20650
    22425 Point Lookout Rd, Leonardtown, MD 20650
    22425 Point Lookout Rd, Leonardtown, MD 20650
    /28

    $1,650 per month

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • House for Rent

    22425 Point Lookout Rd, Leonardtown, MD 20650

    Great Opportunity in Leonardtown!Discover this unique property featuring a spacious garage with a 3-bedroom, 1-bath private residence situated on nearly an acre of land. The home is in excellent condition and has been thoughtfully updated in recent years. Improvements include heat pumps, cabinetry, hot water heater, and more — offering both comfort and peace of mind. The property is serviced

    Conor Loughran CENTURY 21 New Millennium

    22425 Point Lookout Rd, Leonardtown, MD 20650
  • 21549 Point Lookout Rd, Leonardtown, MD 20650
    21549 Point Lookout Rd, Leonardtown, MD 20650
    21549 Point Lookout Rd, Leonardtown, MD 20650
    /43

    $710,000 Sold Jul 24, 2025

    • 3,153 Sq Ft
    • $225/SF
    • 6 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2001

    21549 Point Lookout Rd, Leonardtown, MD 20650

    Contemporary Farmhouse Living on over 24 acres! Drive down the lane past some of your pasture acreage on the left to your 3,000+ sf home backing to mature trees and wooded trails. A small pond is also located on the property. Possibilities abound with the level acreage in front! The property is located between Leonardtown and Callaway close to the Saint Mary's Rive State Park area. Close to

    MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • 23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry 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
  • 22064 Daffodil Ct, Leonardtown, MD 20650
    22064 Daffodil Ct, Leonardtown, MD 20650
    22064 Daffodil Ct, Leonardtown, MD 20650
    /81

    $689,900

    • 6 Beds
    • 4.5 Baths
    • 5,012 Sq Ft

    22064 Daffodil Ct, Leonardtown, MD 20650

    Welcome to this beautifully upgraded Fairfax Model, built in 2022 by Quality Built Homes, Inc., and located in the sought-after Meadows at Town Run community in Leonardtown, Maryland. Just a few years old and meticulously maintained, this home offers 6 bedrooms, 4.5 bathrooms, and 4,295 sq. ft. of finished living space across three levels.Step inside to find wide-plank engineered hardwood

    Laura Bernth RE/MAX One

    22064 Daffodil Ct, Leonardtown, MD 20650
  • 18858 McKays Beach Rd, Leonardtown, MD 20650
    18858 McKays Beach Rd, Leonardtown, MD 20650
    18858 McKays Beach Rd, Leonardtown, MD 20650
    /20

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 2,682 Sq Ft
    • House for Rent

    18858 McKays Beach Rd, Leonardtown, MD 20650

    Experience waterfront living in this beautifully furnished 4-bedroom, 2-bath home, available for lease from November 11, 2025 through May 1, 2026. Flexible lease terms: minimum 2 months, preferred up to 5.5 months. As this is our part-time residence, only furnished, short-term leases are available. No exceptions to our no-pet policy, as other animal scents upset our cats.Property

    18858 McKays Beach Rd, Leonardtown, MD 20650
  • 23075 Hollywood Rd, Leonardtown, MD 20650
    23075 Hollywood Rd, Leonardtown, MD 20650
    23075 Hollywood Rd, Leonardtown, MD 20650
    /82

    $574,000 Sold Jul 24, 2025

    • 3,238 Sq Ft
    • $177/SF
    • 55 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1942

    23075 Hollywood Rd, Leonardtown, MD 20650

    Seller offering up to 3% in Closing assistance - Close in July, just in time for summer in Leonardtown! Built in 1942, this 5-bedroom, 2.5-bath home offers over 3,200 square feet of character-filled living space Original hardwood floors, arched openings, detailed trim work, and vintage glass door knobs are just a few of the timeless details that give this home its warmth and soul—while

    Katy Galloway CENTURY 21 New Millennium

    23075 Hollywood Rd, Leonardtown, MD 20650
    • 23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, 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
  • 40414 Friends Ct, Leonardtown, MD 20650
    40414 Friends Ct, Leonardtown, MD 20650
    40414 Friends Ct, Leonardtown, MD 20650
    /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
  • 22695 Washington St Unit 2, Leonardtown, MD 20650
    22695 Washington St Unit 2, Leonardtown, MD 20650
    22695 Washington St Unit 2, Leonardtown, MD 20650
    /6

    $1,400 per month

    • 1 Bed
    • 1 Bath
    • 11,686 Sq Ft
    • Condo for Rent

    22695 Washington St Unit 2, Leonardtown, MD 20650

    Welcome to your charming new home in the heart of historic Leonardtown! This delightful 1-bedroom, 1-bathroom apartment boasts fresh paint and brand-new luxury vinyl plank (LVP) flooring, providing a modern and comfortable living space. Nestled in an amazing location, you'll enjoy the convenience of being within walking distance to an array of fantastic restaurants, shops, and local attractions.

    Natalya Ford EXP Realty, LLC

    22695 Washington St Unit 2, Leonardtown, MD 20650
  • 21143 Catnip Ct, Leonardtown, MD 20650
    21143 Catnip Ct, Leonardtown, MD 20650
    21143 Catnip Ct, Leonardtown, MD 20650
    /69

    $622,500 Sold Jul 21, 2025

    • 2,642 Sq Ft
    • $236/SF
    • 16 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2003

    21143 Catnip Ct, Leonardtown, MD 20650

    Welcome to this stunning 4-bedroom, 2.5-bath home in the desirable Kingston Estatesneighborhood of Leonardtown. Lovingly maintained by the original owners, this homesits on a beautifully landscaped lot of nearly an acre, and is nestled in a quiet cul-de-sacthat offers both privacy and convenience.As you step inside, you’ll be greeted by the stunning Acacia wood floors that

    Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $527,258 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
  • 23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    /78

    $675,000

    • 5 Beds
    • 3.5 Baths
    • 3,806 Sq Ft

    23092 Town Run Dr, Leonardtown, MD 20650

    Welcome home to The Meadows of Town Run, and this Montross floorplan built by QBHI. The Montross is an efficient floorplan with no wasted space. With 2600 sq ft of above grade living area, 4 bedrooms and 2.5 baths, this home lives comfortably for any family. The beautiful kitchen opens generously to both the living room and an extended morning room. The cozy deck, just off the morning room

    Robin Errington CENTURY 21 New Millennium

    23092 Town Run Dr, Leonardtown, MD 20650
  • 22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    /5

    $1,550 - $1,750 per month

    Seymour Apartments

    1 Bed

    22645 Washington St, Leonardtown, MD 20650

    Introducing Seymour Apartments, in the heart of Historic Downtown Leonardtown! Come live in town just up the hill from the Warf while being steps away from the shops and restaurants on the square. Apartments in the Seymour Apartment building. Access to unit is from a common stairwell with private entrance. Units have new ductless heat pumps, onsite laundry is in common basement area,

    22645 Washington St, Leonardtown, MD 20650
  • 42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    /42

    $906,500 Sold Jul 18, 2025

    • 2,167 Sq Ft
    • $418/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    42239 Riverwinds Dr, Leonardtown, MD 20650

    Welcome to your waterfront retreat on the Potomac River! This well-maintained 3-bedroom, 2.5-bath rambler is perfectly situated on a level 1-acre lot with stunning panoramic water views from every rear-facing room, including all bedrooms. The spacious kitchen opens to a cozy family room with a wood-burning fireplace, ideal for relaxing or entertaining. Step out to the screened-in porch or

    Connie Fitzgerald RE/MAX Closers

    42239 Riverwinds Dr, Leonardtown, MD 20650
    • 40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, 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
  • 41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    /30

    $634,999

    • 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
  • 22680 Washington St Unit 1, Leonardtown, MD 20650
    22680 Washington St Unit 1, Leonardtown, MD 20650
    22680 Washington St Unit 1, Leonardtown, MD 20650
    /46

    $2,300 per month

    • 2 Beds
    • 2.5 Baths
    • 900 Sq Ft
    • House for Rent

    22680 Washington St Unit 1, Leonardtown, MD 20650

    Apartments in beautifully renovated Seymour Building on the square in Leonardtown! 2 bedrooms and 2.5 baths along with all stainless steel appliances. Washer and dryer included. Rent includes water, sewer, trash . Apartment # 1.

    Karen Alford-Brooks CENTURY 21 New Millennium

    22680 Washington St Unit 1, Leonardtown, MD 20650
  • 41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    /54

    $531,000 Sold Jul 18, 2025

    • 2,420 Sq Ft
    • $219/SF
    • 5 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2012

    41699 Courthouse Dr, Leonardtown, MD 20650

    Welcome to 41699 Courthouse Drive, a well-maintained home tucked away on a private lot in the heart of historic Leonardtown. Offering comfort, space, and small-town charm, this property is perfectly positioned with no HOA, public water and sewer, and easy access to everything Leonardtown has to offer.Inside, you’ll find a bright kitchen with plenty of cabinetry, an inviting dining area,

    Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, Leonardtown, MD 20650
    • 23930 Susies Ln, Leonardtown, MD 20650
      23930 Susies Ln, Leonardtown, MD 20650
      23930 Susies Ln, Leonardtown, MD 20650
      /77

      Est $522,286 Not Listed For Sale

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

      23930 Susies Ln, Leonardtown, MD 20650

      23930 Susies Ln, Leonardtown, MD 20650
  • 22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, 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
  • 39870 Lady Baltimore Ave, Leonardtown, MD 20650
    39870 Lady Baltimore Ave, Leonardtown, MD 20650
    39870 Lady Baltimore Ave, 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
  • 43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    /74

    $475,000 Sold Jul 15, 2025

    • 2,400 Sq Ft
    • $198/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    43985 Main Way Rd, Leonardtown, MD 20650

    HUGE COVERED FRONT PORCH (12X18) INVITES YOU TO THIS AMAZINGLY WELL MAINTAINED RAMBLER IN DESIRABLE LANEDON NEIGHBORHOOD WITH DEEDED WATER ACCESS! 3/4 BEDROOMS; 4TH BEDROOM/CRAFT ROOM HAS ACCESS TO UNFINISHED SPACE FOR STORAGE. HARDWOOD FLOORS IN ALL ROOMS EXCEPT KITCHEN AND FAMILY ROOM. FORMAL LIVING ROOM AND SEPARATE DINING ROOM; PERFECT FOR THOSE FAMILY GATHERINGS AND HOLIDAY DINNERS. GOOD

    Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, Leonardtown, MD 20650
    • 23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      /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
  • 20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    /56

    $574,900

    • 4 Beds
    • 3.5 Baths
    • 3,465 Sq Ft

    20919 Ridge Path Way, Leonardtown, MD 20650

    Nestled on a serene and private 3.29-acre lot—plus an additional 0.5-acre parcel—20919 Ridge Path Way offers the perfect balance of seclusion and convenience in the heart of Leonardtown. This professionally upgraded 4-bedroom, 3.5-bath home delivers both peace of mind and high-end comfort with all major systems and appliances less than 5 years old.Step inside and experience a beautifully

    Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
  • 23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, 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
    • 41435 Osborne Ln, Leonardtown, MD 20650
      41435 Osborne Ln, Leonardtown, MD 20650
      41435 Osborne Ln, Leonardtown, MD 20650
      /91

      Est $686,839 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
  • 23650 Rocky Ridge Ct, Leonardtown, MD 20650
    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    23650 Rocky Ridge Ct, 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

Showing Results 1 - 40, Page 1 of 18

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Real Estate & Homes

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 21 days on the market compared to the national average of 70 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $485,000, down 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$485,000
Median Single Family Sale Price
$630,000
Median Townhouse Sale Price
$483,000
Average Price Per Sq Ft
$155
Number of Homes for Sale
6
Last 12 months Home Sales
120
Months of Supply
0.60
Median List Price
$490,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-18%
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