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Leonardtown Homes for Sale

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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

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage 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 crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    20798 Waterside Dr, Leonardtown, MD 20650
  • 40751 Merlin Way, Leonardtown, MD 20650
    40751 Merlin Way, Leonardtown, MD 20650
    40751 Merlin Way, Leonardtown, MD 20650
    /43

    $635,000

    $15K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,601 Sq Ft

    40751 Merlin Way, Leonardtown, MD 20650

    Welcome to this beautiful brick‑front retreat in the highly sought‑after Avenmar Community of historic Leonardtown, Maryland. Set on over 3 private acres and tucked away on a secluded lane shared by only three other homes, this property offers the perfect blend of privacy, nature, and convenience, an ideal setting for cozy fall evenings and peaceful year‑round living.Freshly updated with

    Agent Photo

    Tracy Trammell

    Metro City Realty

    40751 Merlin Way, Leonardtown, MD 20650
  • Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    /42

    $449,900

    New Construction Open Sun 11:30AM - 3:30PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    Ready Now***Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full bath, perfect for a guest suite or home

    Laura Lee Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    /6

    $175,000

    • Land
    • 6.24 Acres
    • $28,045 per Acre

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650

    6+ acre lot zoned RPD in a prime location with approximately 600 ft of road frontage and high visibility potential. This is NOT currently a residential building lot because it failed a perc test in April 2005. However, the current Comprehensive Zoning Ordinance lists other “potential” uses that may not require on-site sewage disposal. The list includes but is not limited to: Construction

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
  • 23684 Dragonfly Ln, Leonardtown, MD 20650
    23684 Dragonfly Ln, Leonardtown, MD 20650
    23684 Dragonfly Ln, Leonardtown, MD 20650
    /41

    $449,900

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

    23684 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersNatural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook 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 CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe Shower

    Quality Built Homes Builder
    23684 Dragonfly Ln, Leonardtown, MD 20650
  • 43175 N Megan Ln, Leonardtown, MD 20650
    43175 N Megan Ln, Leonardtown, MD 20650
    43175 N Megan Ln, Leonardtown, MD 20650
    /30

    $1,450,000

    • Land
    • 70.61 Acres
    • $20,535 per Acre

    43175 N Megan Ln, Leonardtown, MD 20650

    Discover 89± acres of prime real estate offering unparalleled privacy just minutes from Leonardtown, California, Solomons Island, and Naval Air Station Patuxent River. Zoned RPD (Rural Preservation District) with agricultural use, this expansive TWO-PARCEL listing presents many possibilities. Rebuild on an existing foundation overlooking scenic rolling fields, design a custom private estate,

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    43175 N Megan Ln, Leonardtown, MD 20650
  • 24040 Hollywood Rd, Hollywood, MD 20636
    24040 Hollywood Rd, Hollywood, MD 20636
    24040 Hollywood Rd, Hollywood, MD 20636
    /5

    $320,000

    $30K 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
  • 23672 Weeping Willow Way, Leonardtown, MD 20650
    23672 Weeping Willow Way, Leonardtown, MD 20650
    23672 Weeping Willow Way, Leonardtown, MD 20650
    /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
  • 25375 Loveville Rd, Leonardtown, MD 20650
    25375 Loveville Rd, Leonardtown, MD 20650
    25375 Loveville Rd, Leonardtown, MD 20650
    /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 2017, 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
  • 22157 Monterey Place, Leonardtown, MD 20650
    22157 Monterey Place, Leonardtown, MD 20650
    22157 Monterey Place, Leonardtown, MD 20650
    /60

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 3,314 Sq Ft

    22157 Monterey Place, Leonardtown, MD 20650

    Nestled in the charming sought after Clearfields community, this stunning Colonial blends modern luxury with everyday comfort. Set on a beautifully landscaped 1.22-acre lot, this 4-bedroom, 2.5-bathroom home provides ample space for both relaxation and entertaining.At the heart of the home is a chef's dream kitchen, featuring custom cabinetry, gorgeous quartz countertops, a designer

    Tracey Summers CENTURY 21 New Millennium

    22157 Monterey Place, Leonardtown, MD 20650
  • 23208 Clarks Rest Rd, Leonardtown, MD 20650
    23208 Clarks Rest Rd, Leonardtown, MD 20650
    /2

    $549,000

    Coming Soon Oct 22
    • 4 Beds
    • 3.5 Baths
    • 3,006 Sq Ft

    23208 Clarks Rest Rd, Leonardtown, MD 20650

    LOCATION! LOCATION! LOCATION! Coming Soon. Full Pictures and Remarks to come closer to active date.

    Jimmy Hayden RE/MAX One

    23208 Clarks Rest Rd, Leonardtown, MD 20650
  • 0 Saint Johns Rd, Hollywood, MD 20636
    0 Saint Johns Rd, Hollywood, MD 20636
    0 Saint Johns Rd, Hollywood, MD 20636
    /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
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /75

    $624,900

    $20K 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
  • 23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    /56

    $615,000

    • 5 Beds
    • 4 Baths
    • 4,346 Sq Ft

    23620 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so

    Tyler Mattingly Coldwell Banker Premier

    23620 Gunnell Dr, Leonardtown, MD 20650
  • 22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    /45

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    22010 Society Hill Rd, Leonardtown, MD 20650

    Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area

    Fran Slade Compass

    22010 Society Hill Rd, Leonardtown, MD 20650
  • 0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    /17

    $288,900

    • Land
    • 23.44 Acres
    • $12,325 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or

    Brooke Matthews RE/MAX One

    0 Whirlwind Rd, Leonardtown, MD 20650
  • 40115 Combs Creek Way, Leonardtown, MD 20650
    40115 Combs Creek Way, Leonardtown, MD 20650
    40115 Combs Creek Way, Leonardtown, MD 20650
    /89

    $1,590,000

    $110K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,993 Sq Ft

    40115 Combs Creek Way, Leonardtown, MD 20650

    Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year.Perfectly positioned to capture breathtaking water views, this exceptional property offers a

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650
  • 23444 Lindsay Dr, Leonardtown, MD 20650
    23444 Lindsay Dr, Leonardtown, MD 20650
    23444 Lindsay Dr, Leonardtown, MD 20650
    /43

    $629,900

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft

    23444 Lindsay Dr, Leonardtown, MD 20650

    Discover a luxurious lifestyle in this stunning 2023 Colonial home nestled in the desirable Clark's Rest community. This exquisite residence boasts four spacious bedrooms and three and a half elegantly appointed bathrooms, perfect for both relaxation and entertaining. There are two unfinished bedrooms in the basement, so potentially it can be 6 bedrooms house. The heart of the home features

    Natalya Ford RE/MAX One

    23444 Lindsay Dr, Leonardtown, MD 20650
  • 40611 Merion Ct, Leonardtown, MD 20650
    40611 Merion Ct, Leonardtown, MD 20650
    40611 Merion Ct, Leonardtown, MD 20650
    /58

    $624,990

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    40611 Merion Ct, Leonardtown, MD 20650

    Welcome to 40611 Merion Court, Leonardtown, MD 20650! This stunning three-level Colonial offers the perfect blend of elegance, comfort, and resort-style living, ideally positioned with beautiful views backing directly to Breton Bay golf course. Featuring 4 bedrooms, 3.5 baths, and a fully finished basement, this home provides exceptional space for both everyday living and entertaining. The

    Kalee Kelly Infinitas Realty Group

    40611 Merion Ct, Leonardtown, MD 20650
  • 23214 Dairy Barn Dr, Leonardtown, MD 20650
    23214 Dairy Barn Dr, Leonardtown, MD 20650
    23214 Dairy Barn Dr, Leonardtown, MD 20650
    /44

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    Located in the sought-after Clark's Rest community, this home features Marrick’s Kensington floor plan with a covered front entry and separate sitting porch. Inside, the two-story foyer opens to a formal dining room and versatile office, library, or playroom. The kitchen features a large center island, granite countertops, gas cooktop, double wall ovens, abundant cabinetry, butler’s pantry, and

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn Dr, Leonardtown, MD 20650
  • 22337 Sandra Ln, California, MD 20619
    22337 Sandra Ln, California, MD 20619
    22337 Sandra Ln, California, MD 20619
    /34

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    22337 Sandra Ln, California, MD 20619

    Spacious 1,472 Sq. Ft. totally remodeled Rancher; New Roof, New siding, New Windows, New Doors, New Heat Pump, New electric Service with Outside Disconnect, Conditioned Crawl Space, New Hot Water Heater, Updated bathrooms w. New Vanities & Fixtures, New Kitchen with Beautiful Meraki Quartz Countertops and Eating-Bar Island, Upgraded Appliances, Open Living Great Room, Separate Family Room

    Carl Franzen Franzen Realtors, Inc.

    22337 Sandra Ln, California, MD 20619
  • 42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    /15

    $374,900

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS—ANY RENTAL ADVERTISEMENT FOR THIS PROPERTY IS FRAUDULENT. The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, Leonardtown, MD 20650
  • 22386 Laceys Ln, California, MD 20619
    22386 Laceys Ln, California, MD 20619
    22386 Laceys Ln, California, MD 20619
    /48

    $424,900

    • 4 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    22386 Laceys Ln, California, MD 20619

    Welcome to 22386 Laceys Lane in California, Maryland! Nestled on a quiet cul-de-sac, this spacious 4-bedroom, 3-bath home offers the perfect blend of comfort, functionality, and everyday living. Step inside to discover large, open common areas designed for gathering with family and friends, while an abundance of natural light fills the home, creating a warm and inviting atmosphere

    Matthew Burgan Infinitas Realty Group

    22386 Laceys Ln, California, MD 20619
  • 41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    /22

    $300,000

    • Land
    • 1.51 Acres
    • $198,675 per Acre

    41708 Fenwick St, Leonardtown, MD 20650

    Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated

    Tig Wright Redfin Corp

    41708 Fenwick St, Leonardtown, MD 20650
  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $175,000

    • Land
    • 5 Acres
    • $35,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location.The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • 41888 Jenkins Ct, Leonardtown, MD 20650
    41888 Jenkins Ct, Leonardtown, MD 20650
    41888 Jenkins Ct, Leonardtown, MD 20650
    /41

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    41888 Jenkins Ct, Leonardtown, MD 20650

    Interior Photos Coming Soon! Expected on market date is Sept 1, 2026Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown

    Wayne Floyd RE/MAX One

    41888 Jenkins Ct, Leonardtown, MD 20650
  • 23354 Lindsay Dr, Leonardtown, MD 20650
    23354 Lindsay Dr, Leonardtown, MD 20650
    23354 Lindsay Dr, Leonardtown, MD 20650
    /53

    $609,900

    $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,736 Sq Ft

    23354 Lindsay Dr, Leonardtown, MD 20650

    Welcome to this stunning rambler in the highly sought-after community of Clark's Rest! Thoughtfully designed with 9' ceilings, quartz countertops, designer finishes, and upgrades throughout, this home offers the perfect blend of style, comfort, and functionality.The main level features three spacious bedrooms and two full bathrooms, including a beautiful owner's suite with dual vanities. The

    Dorothy Bistransin Redfin Corp

    23354 Lindsay Dr, Leonardtown, MD 20650
  • 22601 Avenmar Dr, Leonardtown, MD 20650
    22601 Avenmar Dr, Leonardtown, MD 20650
    22601 Avenmar Dr, Leonardtown, MD 20650
    /91

    $699,000

    $81K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,484 Sq Ft

    22601 Avenmar Dr, Leonardtown, MD 20650

    Welcome to Avenmar, where this spacious home is situated on a beautiful lot of over two acres, offering privacy, mature trees, and a peaceful wooded setting. Built in 2002 and largely in its original condition, the home has been well maintained and is ready for its next owner to bring their own style and updates.The main level offers a spacious, open layout with a formal dining room,

    Jennifer Goddard CENTURY 21 New Millennium

    22601 Avenmar Dr, Leonardtown, MD 20650
  • 43146 N Megan Ln, Leonardtown, MD 20650
    43146 N Megan Ln, Leonardtown, MD 20650
    43146 N Megan Ln, Leonardtown, MD 20650
    /14

    $319,000

    • 3 Beds
    • 1 Bath
    • 2,068 Sq Ft

    43146 N Megan Ln, Leonardtown, MD 20650

    Looking for acreage, privacy, and freedom? Discover this 12.73 acre homestead. This mostly wooded property that offers mature trees, privacy, and zero HOA restrictions located just minutes from Leonardtown, California, Solomons Island, and Naval Air Station Patuxent River. Featuring a vintage 1953 3-bed/1-bath home which is being sold "AS IS", detached garage, and multiple outbuildings, the

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    43146 N Megan Ln, Leonardtown, MD 20650
  • 41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    /70

    $389,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    41620 Church St, Leonardtown, MD 20650

    Fully renovated. Move-in ready. Prime downtown location.Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value.Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of

    Chanel Li Evergreen Properties

    41620 Church St, Leonardtown, MD 20650
  • 23679 Weeping Willow Way, Leonardtown, MD 20650
    23679 Weeping Willow Way, Leonardtown, MD 20650
    23679 Weeping Willow Way, Leonardtown, MD 20650
    /41

    $449,900

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

    23679 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D2 Natural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook 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 CabinetsIvory Taj Quartz CountertopsSplendur Cream BacksplashDeluxe Shower in Primary

    Quality Built Homes Builder
    23679 Weeping Willow Way, Leonardtown, MD 20650
  • Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
    /42

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

    *** November Delivery ***ALMOST READY*******Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #143 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

    Laura Lee Hefley RE/MAX One

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /74

    $680,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Exciting New Offer! Sellers are offering $10,000 in buyer assistance to help make this home your own! Put it toward eligible closing costs or an interest rate buydown, and keep more of your own money available for any updates you want. Ask your lender how the credit could work for you.Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • 0 Bayside Rd, Leonardtown, MD 20650
    0 Bayside Rd, Leonardtown, MD 20650
    0 Bayside Rd, Leonardtown, MD 20650
    /30

    $1,750,000

    $115K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft

    0 Bayside Rd, Leonardtown, MD 20650

    Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The

    Bonnie Haley Haley Family Realty

    0 Bayside Rd, Leonardtown, MD 20650
  • 41650 Miss Bessie Dr, Leonardtown, MD 20650
    41650 Miss Bessie Dr, Leonardtown, MD 20650
    41650 Miss Bessie Dr, Leonardtown, MD 20650
    /3

    $155,000

    • Land
    • 19,166 Sq Ft
    • $352,273 per Acre

    41650 Miss Bessie Dr, Leonardtown, MD 20650

    Great building lot in the Leonardtown city limites with water and sewer available. Part of Singletree but no HOA dues. Currently staked for a house location. Property corners are not staked. See map in documents. Located across from the hospital, walking distance to down town.

    Jan Barnes CENTURY 21 New Millennium

    41650 Miss Bessie Dr, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 2

Maryland St Marys County Leonardtown

Real Estate & Homes for Sale in Leonardtown, Leonardtown

Leonardtown, MD, MD Home Prices vs. Nearby Neighborhoods

Leonardtown California Callaway Wildewood
Median Home Price
$545,000
$399,900
$457,500
$399,900
Median Sale Price
$540,000
-3% YoY
$397,000
+7% YoY
$465,000
+4% YoY
$392,500
+2% YoY
Avg. Price per Square Foot
$188
$194
$202
$196
Median Single Family Price
$595,000
$420,000
$487,000
$485,000
Median Townhouse Price
$452,450
$304,000
$258,000
$366,500
Median Condo Price
$302,000
$199,000
--
$235,000
Total Active Listings
61 listings
38 listings
7 listings
24 listings
Market Conditions
3 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
2 Months of Supply
Seller's Market

Frequently Asked Questions Why Live in Leonardtown

Is Leonardtown a good place to live?
Leonardtown is a good place to live. Leonardtown is considered car-dependent and somewhat bikeable with some transit options. Leonardtown has 7 parks for recreational activities.It has a median age of 38. The average household income is $140,110 which is above the national average. College graduates make up 40% of residents. A majority of residents in Leonardtown are home owners, with 28% of residents renting and 72% of residents owning their home. A local real estate agent serving Leonardtown can help you decide if this neighborhood is the right one for you. Learn more on our Leonardtown neighborhood guide.
How much do you need to make to afford a house in Leonardtown?
The median home price in Leonardtown is $545,000. If you put a 20% down payment of $109,000 and had a 30-year fixed mortgage with an interest rate of 7.03%, your estimated principal and interest payment would be $2,910 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $125K a year to afford the median home price in Leonardtown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Leonardtown is $140K.
What are the best public schools in Leonardtown?
The best public schools that serve Leonardtown are:
What are the best private schools in Leonardtown?
The best private schools that serve Leonardtown are:
What are the most popular zip codes in Leonardtown, Leonardtown, MD?
The most popular zip codes in Leonardtown, Leonardtown, MD include 20650, 20636, 20619, 20609 and 20606.
What are the most popular neighborhoods near Leonardtown, Leonardtown, MD?
The most popular neighborhoods near Leonardtown, Leonardtown, MD are Callaway, Mechanicsville, Piney Point, Newburg and Port Republic.
Learn more about living in Leonardtown
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