33

Leonardtown, MD Homes for Sale

Section Image Section Image
  • 22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    22547 Landing Way, Leonardtown, MD 20650
    /48

    $515,000

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft

    22547 Landing Way, Leonardtown, MD 20650

    Experience life in a charming waterfront community where every day feels like a getaway. Enjoy kayaking, paddleboarding, and a variety of outdoor activities right at your doorstep. Start your mornings with yoga on the wharf or take a short stroll to the square for weekend concerts and local events. Located in the heart of Leonardtown, this home offers not only convenience but a vibrant lifestyle

    Agent Photo

    Trish Brow

    EXP Realty, LLC

    (227) 230-5778

    22547 Landing Way, Leonardtown, MD 20650
  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $500,000

    • 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

    (227) 230-6008

    20798 Waterside Dr, Leonardtown, MD 20650
  • 40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    /61

    $679,900

    • 2 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    MOTIVATED SELLER! COME FALL IN LOVE WITH THE VIEW AND MAKE AN OFFER! Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream

    Agent Photo

    Mileah Walker

    Real Broker, LLC

    (227) 230-0320

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • 20045 Tower Hill Rd, Leonardtown, MD 20650
    20045 Tower Hill Rd, Leonardtown, MD 20650
    20045 Tower Hill Rd, Leonardtown, MD 20650
    /65

    $1,450,000

    • 5 Beds
    • 7 Baths
    • 7,376 Sq Ft

    20045 Tower Hill Rd, Leonardtown, MD 20650

    Set quietly within 12 picturesque acres overlooking a peaceful creek, Tower Hill Retreat offers an extraordinary opportunity to experience refined country living in a natural setting. This impressive estate features 5 bedrooms (with potential for a sixth) and 5 full and 2 half bathrooms in a thoughtfully designed and exceptionally versatile floor plan. Rich hardwood and tile flooring extend

    Barbara Stellway KW Metro Center

    20045 Tower Hill Rd, Leonardtown, MD 20650
  • 41377 Doctors Crossing Rd, Leonardtown, MD 20650
    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    /63

    $639,999

    • 5 Beds
    • 4 Baths
    • 3,724 Sq Ft

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    Welcome Home!41377 Doctors Crossing Rd is a well-maintained home located in the sought-after Clark’s Rest community — where comfortable living meets a vibrant neighborhood lifestyle, with a pond just steps away and walking distance to the clubhouse. Offering 5,538 total square feet, including 3,724 finished square feet above grade, this home provides the space and flexibility. As you step

    Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
  • Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    /35

    $449,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    Homesite #99 Madison D3: ****ALMOST READY FOR SPRING DELIVERY***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 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that

    Laura Bernth RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    /34

    $449,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650

    Homesite #101 Madison D3: ***ALMOST READY FOR MARCH DELIVERY***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 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that

    Laura Bernth RE/MAX One

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
  • 41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    /50

    $680,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,992 Sq Ft

    41488 Pensive St, Leonardtown, MD 20650

    Updated Photos coming in a couple weeks! Welcome to this Belmont model in Leonard’s Grant, offering a spacious layout and thoughtful design throughout. As you enter the home, you’re welcomed by hardwood floors, a grand entryway, and a beautiful staircase that creates an inviting first impression.To the right, French doors open to a large room that works well as a home office or additional

    Heather Foster RE/MAX One

    41488 Pensive St, Leonardtown, MD 20650
  • 000 Saint Andrews Church Rd, Leonardtown, MD 20650
    000 Saint Andrews Church Rd, Leonardtown, MD 20650
    000 Saint Andrews Church Rd, Leonardtown, MD 20650
    /36

    $104,900

    • Land
    • 4.11 Acres
    • $25,523 per Acre

    000 Saint Andrews Church Rd, Leonardtown, MD 20650

    Located in Leonardtown in St. Marys County, this 4.11 acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable conditions; buyers to

    Casey Kennedy Whitetail Properties Real Estate

    000 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 41655 Church St, Leonardtown, MD 20650
    41655 Church St, Leonardtown, MD 20650
    41655 Church St, Leonardtown, MD 20650
    /4

    $725,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 2,834 Sq Ft

    41655 Church St, Leonardtown, MD 20650

    Built in 1875, this substantial 2,800 sq ft residence offers a rare opportunity to own a large historic home in highly desirable Leonardtown. Featuring 5 bedrooms and 2 bathrooms, the property showcases classic architecture with a formal living room and dining room, and enduring period details. Original features include a beautiful antique stamped tin ceiling and two fireplaces, adding

    Chris Norris Topside Realty

    41655 Church St, Leonardtown, MD 20650
  • 40737 Bobwhite Ln, Leonardtown, MD 20650
    40737 Bobwhite Ln, Leonardtown, MD 20650
    40737 Bobwhite Ln, Leonardtown, MD 20650
    /101

    $809,900

    • 4 Beds
    • 3.5 Baths
    • 5,454 Sq Ft

    40737 Bobwhite Ln, Leonardtown, MD 20650

    Avenmar beauty situated on over 3.5 acres, offering exceptional space and privacy. The custom kitchen features top-of-the-line appliances, custom cabinetry, solid-surface countertops, and stunning light fixtures. The main level includes formal dining and living rooms, a dedicated office space, and a two-story family room with an overlook from above. Floor-to-ceiling windows showcase peaceful

    Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
  • 23592 Belmar Dr, Leonardtown, MD 20650
    23592 Belmar Dr, Leonardtown, MD 20650
    /2

    $680,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft

    23592 Belmar Dr, Leonardtown, MD 20650

    Photos to come.QBH Belmont model with a beautiful Sunroom.

    Heather Foster RE/MAX One

    23592 Belmar Dr, 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
  • 42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    /10

    $1,999,999

    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • 24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • 22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    /3

    $175,000

    • Land
    • 7.58 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, Leonardtown, MD 20650
  • 41516 Marwood Cir, Leonardtown, MD 20650
    41516 Marwood Cir, Leonardtown, MD 20650
    41516 Marwood Cir, Leonardtown, MD 20650
    /55

    $437,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 3.5 Baths
    • 2,402 Sq Ft

    41516 Marwood Cir, Leonardtown, MD 20650

    Open House Sat March 21st and Sun March 22nd from 1:00-3:00pm. Welcome home to Marwood Circle in the desirable Clark's Rest Neighborhood of Leonardtown. This nearly new townhome built in 2020 has over 2400 square feet of living space and is in move in condition. Nice open concept on the main level includes an updated kitchen with granite countertops and island, stainless appliances and pantry,

    Cynthia Ballard CENTURY 21 New Millennium

    41516 Marwood Cir, Leonardtown, MD 20650
  • 20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    /13

    $170,000

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    *Back on the market. A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • 22343 Newtowne Neck Rd, Leonardtown, MD 20650
    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    22343 Newtowne Neck Rd, Leonardtown, MD 20650
    /40

    $474,900

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft

    22343 Newtowne Neck Rd, Leonardtown, MD 20650

    MOVE-IN READY!! Welcome to this beautifully maintained 4-bedroom, 2-bath rambler situated on a 1-acre lot in Leonardtown, Maryland. Offering the ease of one-level living and a functional, flowing floor plan, this home combines space, comfort, and practicality in a peaceful Southern Maryland setting. Step inside to find a spacious living room with gleaming floors and abundant natural light. The

    Mark Frisco CENTURY 21 New Millennium

    22343 Newtowne Neck Rd, Leonardtown, MD 20650
  • 22394 White Oak Rd, Leonardtown, MD 20650
    22394 White Oak Rd, Leonardtown, MD 20650
    22394 White Oak Rd, Leonardtown, MD 20650
    /28

    $495,000

    • 4 Beds
    • 3 Baths
    • 2,507 Sq Ft

    22394 White Oak Rd, Leonardtown, MD 20650

    Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-bedroom, 3-bath split foyer offers space and comfort, and is move-in ready! The main level showcases stunning hardwood floors and a bright, inviting layout perfect for everyday living. The fully finished walk-out lower level features a spacious family room with a cozy fireplace, creating the ideal space for

    Barbara Stellway KW Metro Center

    22394 White Oak Rd, Leonardtown, MD 20650
  • 40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    /28

    $149,900

    • Land
    • 2.28 Acres
    • $65,746 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, Leonardtown, MD 20650
  • Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
    /46

    $489,900 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 132 TO BE BUILT New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and

    Laura Bernth RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
  • 40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    40855 Spring House Ln, Leonardtown, MD 20650
    /68

    $599,900

    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft

    40855 Spring House Ln, Leonardtown, MD 20650

    Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven

    Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, 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

    • 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
  • 20265 Hawks Way, Leonardtown, MD 20650
    20265 Hawks Way, Leonardtown, MD 20650
    /2

    $149,900

    • Land
    • 1.44 Acres
    • $104,097 per Acre

    20265 Hawks Way, Leonardtown, MD 20650

    Prime 1.44-Acre Buildable Lot in Leonardtown, MD Welcome to 20265 Hawks Way, a fantastic opportunity to build your dream home on a spacious 1.44-acre parcel on a quiet street. This generous lot offers a blank canvas — cleared and ready for construction — surrounded by other new construction homes that bring a sense of neighborhood and modern living while maintaining a peaceful, rural feel.

    Mark Frisco CENTURY 21 New Millennium

    20265 Hawks Way, Leonardtown, MD 20650
  • 40736 Center 40 Cir, Leonardtown, MD 20650
    40736 Center 40 Cir, Leonardtown, MD 20650
    40736 Center 40 Cir, Leonardtown, MD 20650
    /58

    $415,000

    • 3 Beds
    • 2.5 Baths
    • 1,829 Sq Ft

    40736 Center 40 Cir, Leonardtown, MD 20650

    BACK ON MARKET. Charming Split Level home on just over 1/2 an acre in Breton Bay. As you enter the front door, the hardwood floors lead you throughout the main living areas of the home. Living room and dining room are both located on the main level. Kitchen with updated Corian counters and stainless appliances. Back door off kitchen opens to patio and back yard. Great entertaining space or space

    Kelly Padgett CENTURY 21 New Millennium

    40736 Center 40 Cir, Leonardtown, MD 20650
  • 0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    /34

    $104,900

    • Land
    • 4.11 Acres
    • $25,523 per Acre

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    Located in Leonardtown in St. Mary’s County, this 4.11± acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable conditions; buyers

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, 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

    $205,000

    • Land
    • 5 Acres
    • $41,000 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 seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • 43552 Bayberry Ct, Leonardtown, MD 20650
    43552 Bayberry Ct, Leonardtown, MD 20650
    43552 Bayberry Ct, Leonardtown, MD 20650
    /4

    $599,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,428 Sq Ft

    43552 Bayberry Ct, Leonardtown, MD 20650

    Nestled on 2.2 private acres in Chestnut Ridge, this beautiful 4-bedroom home offers space, comfort, and functionality for modern living. The home features generously sized bedrooms and a thoughtfully designed layout perfect for both everyday life and entertaining. The main level includes a spacious kitchen and family room combination—ideal for gatherings—complete with a cozy brick gas fireplace

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    43552 Bayberry Ct, Leonardtown, MD 20650
  • 20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    /28

    $579,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • 0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    /18

    $20,000

    • Land
    • 1.23 Acres
    • $16,260 per Acre

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636

    Rarely does a parcel this clean, this well-located, and this perfectly positioned for long-term appreciation come to market — and this 1.23-acre lot on Hollywood Road in Hollywood, Maryland is exactly that. Gently rolling terrain, paved road frontage, power already at the street, zero flood zone, zero wetlands, and zero floodway make this a compelling land hold in St. Mary's County today. Zoned

    Joseph Hawkins Hawkins Real Estate Company

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
Maryland St Marys County Leonardtown

Real Estate & Homes for Sale in Leonardtown, MD

Why Live in Leonardtown

Leonardtown is a Southern Maryland community on the rise, with the population nearly doubling between 2010 and 2020. “It’s one of the fastest-growing municipalities in Maryland,” says Jimmy Hayden , a Leonardtown native and Realtor with Re/Max Realty Group. ...

Learn more about living in Leonardtown

Frequently Asked Questions

What is the average home price in Leonardtown, MD?
Homes for sale in Leonardtown, MD have an average home price of $615,478.
How many homes have sold over the last 12 months in Leonardtown, MD?
162 homes have sold in Leonardtown, MD over the last 12 months.
Is Leonardtown, MD a safe city?
In general, the safest neighborhoods in Leonardtown, MD with lower crime scores are Callaway, Saint George Island and Piney Point.
What are the most popular zip codes in Leonardtown, MD?
The most popular zip codes in Leonardtown, MD include 20650, 20636, 20619, 20609 and 20659.
What are the most popular neighborhoods in Leonardtown, MD?
The most popular neighborhoods in Leonardtown, MD with the most homes for sale are Callaway, Saint George Island and Piney Point.
How much do you need to make to afford a house in Leonardtown?
The median home price in Leonardtown is $542,500. If you put a 20% down payment of $108,500 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $2,660 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K a year to afford the median home price in Leonardtown. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Leonardtown, MD?
Leonardtown, MD has highly rated public and private schools. Some of the best schools in Leonardtown based on Niche Grades are St. Mary's Ryken High School, Captain Walter Francis Duke Elementary School and Leonardtown Middle School. The neighborhoods in Leonardtown with the highest rated schools are Callaway, Saint George Island and Piney Point. Browse all the schools in Leonardtown, MD to learn more.

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 44 days on the market compared to the national average of 55 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $538,750, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$538,750
Median Single Family Sale Price
$599,000
Median Townhouse Sale Price
$454,225
Average Price Per Sq Ft
$196
Number of Homes for Sale
20
Last 12 months Home Sales
162
Months of Supply
1.50
Median List Price
$542,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group