6,682

Leonardtown, MD Homes

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  • 40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    /31

    $470,000

    • 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 One

    (240) 697-2564

    40534 Miss Ettas Way, 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
  • 22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    /86

    $633,000 Sold Sep 19, 2025

    • 3,745 Sq Ft
    • $169/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2004

    22272 Orchard Ct, Leonardtown, MD 20650

    Welcome to Hanover Farms in Breton Bay, a sought-after private water-access community in Leonardtown offering a neighborhood pier and beach. This charming rambler with a full basement sits on nearly an acre at the end of a quiet cul-de-sac, featuring a flat, fenced lot for both privacy and function.Inside, the split floor plan provides the perfect balance of comfort and convenience, with the

    Christina Reed RE/MAX One

    22272 Orchard Ct, Leonardtown, MD 20650
    • 42798 Saint Andrews Church Rd, Leonardtown, MD 20650
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650
      /48

      Est $424,530 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,692 Sq Ft

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 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 One

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • 41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    /34

    $3,500 per month

    • 3 Beds
    • 3.5 Baths
    • 2,859 Sq Ft
    • House for Rent

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    Beautiful 6 year old home is ready for you! Clarks Rest is just minutes form all the shopping and restaurants in Leonardtown Square. Occupancy can be before school starts this fall. 3 large bedrooms upstairs with a separate sitting area off the primary bedroom that could be a 4th bedroom. Luxury vinyl plank flooring throughout the main level. The lower level if finished and features another full

    Gail Nyman RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
  • 22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    /46

    $350,000 Sold Sep 19, 2025

    • 1,160 Sq Ft
    • $302/SF
    • 28 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1978

    22798 Lawrence Ave, Leonardtown, MD 20650

    Looking to be within walking distance to all of the amenities that Leonardtown Square has to offer? Look no further than this updated turn key townhome. You can stroll on the sidewalks to all of the local shops, restaurants, post office, and the waterfront park. Conveniently close to St. Mary's Hospital, Patuxent River Naval Air Station, and Solomons Island. No HOA, public water and public

    Barbara Click O'Brien Realty ERA Powered

    22798 Lawrence Ave, Leonardtown, MD 20650
    • 21919 Budds Creek Rd, Leonardtown, MD 20650
      21919 Budds Creek Rd, Leonardtown, MD 20650
      21919 Budds Creek Rd, Leonardtown, MD 20650
      /48

      Est $364,172 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,680 Sq Ft

      21919 Budds Creek Rd, Leonardtown, MD 20650

      21919 Budds Creek Rd, Leonardtown, MD 20650
  • 21745 Pinehurst Ct, Leonardtown, MD 20650
    21745 Pinehurst Ct, Leonardtown, MD 20650
    21745 Pinehurst Ct, Leonardtown, MD 20650
    /82

    $605,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,860 Sq Ft

    21745 Pinehurst Ct, Leonardtown, MD 20650

    OPEN HOUSE CANCELED DUE TO ACCEPTED CONTRACT. Desirable Breton Bay Brick Colonial with a NEW ROOF! Enter the soaring two-story foyer of this 4-bedroom, 2.5 bath home, and take note of the refinished hardwood floors, wide staircase with wrought iron railings, and Palladian window that allows for lots of natural light. Head past the shiplap wall treatment into the eat-in kitchen that features tall

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 230-4358

    21745 Pinehurst 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
    /22

    $2,400 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 midcentury modern 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

    18858 McKays Beach Rd, Leonardtown, MD 20650
  • 23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    /48

    $469,900 Sold Sep 18, 2025

    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths

    23664 Dragonfly Ln, Leonardtown, MD 20650

    ***UNDER CONTRACT***Unit 86 Cumberland D1New 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,

    Laura Bernth RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
    • 40606 Crimson Way, Leonardtown, MD 20650
      40606 Crimson Way, Leonardtown, MD 20650
      40606 Crimson Way, Leonardtown, MD 20650
      /9

      Est $364,667 Not Listed For Sale

      40606 Crimson Way, Leonardtown, MD 20650

      40606 Crimson Way, Leonardtown, MD 20650
  • 19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    /13

    $130,000

    • Land
    • 5.09 Acres
    • $25,540 per Acre

    19921 Tower Hill Rd, Leonardtown, MD 20650

    Water access on this 5+ acre lot in sought after Leonardtown buildable, wooded, and perc'd lot. Build your dream home or purchase for access for kayaking. Covenants and Restrictions for neighborhood.

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (227) 888-6903

    19921 Tower Hill Rd, Leonardtown, MD 20650
  • 22373 Enoch Rd, Leonardtown, MD 20650
    22373 Enoch Rd, Leonardtown, MD 20650
    22373 Enoch Rd, Leonardtown, MD 20650
    /74

    $3,200 per month

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    22373 Enoch Rd, Leonardtown, MD 20650

    Gorgeous, Classy, Completely Remodeled Colonial on a Beautiful Premium Lot Backing to Trees in the Sought After Neighborhood of Breton Bay/Society Hill. A Welcoming Covered Front Porch is the perfect spot for enjoying the array of birds that live around the property. Open Floor Plan with Upgraded, Luxury Vinyl Plank (LVP) Flooring. Stylish Living Room with Wood Burning Fireplace, Charming Dining

    Jenny Norris EXP Realty, LLC

    22373 Enoch Rd, Leonardtown, MD 20650
  • 40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    /72

    $740,000 Sold Sep 18, 2025

    • 6,064 Sq Ft
    • $122/SF
    • 8 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2002

    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
    • 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 $535,277 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
  • 23682 Dragonfly Ln, Leonardtown, MD 20650
    23682 Dragonfly Ln, Leonardtown, MD 20650
    23682 Dragonfly Ln, Leonardtown, MD 20650
    /55

    $469,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    23682 Dragonfly Ln, Leonardtown, MD 20650

    ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Unit 89 Oakley D1New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious

    Laura Bernth RE/MAX One

    23682 Dragonfly Ln, Leonardtown, MD 20650
  • 39872 Wrinkle Free Ln Unit 2, Leonardtown, MD 20650
    39872 Wrinkle Free Ln Unit 2, Leonardtown, MD 20650
    39872 Wrinkle Free Ln Unit 2, Leonardtown, MD 20650
    /34

    $1,900 per month

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • House for Rent

    39872 Wrinkle Free Ln Unit 2, Leonardtown, MD 20650

    Freshly painted 3 bedroom 3 bathroom Leonardtown apartment on quiet country road, near Newtowne Neck State Park and local seafood restaurant. Entrance to unit is from shared entryway with private door. Unit has washer dryer, central heat/AC, parking for two cars and beautiful water views. $40 Application fee to run credit check per person over the age of 18, 1 year lease required, no pets and no

    39872 Wrinkle Free Ln Unit 2, 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 Sold Sep 18, 2025

    • 3,914 Sq Ft
    • $153/SF
    • 20 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1993

    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
    • 22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      /36

      Est $446,657 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
    /89

    $695,000 Under Contract

    • 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
  • 23701 Robert Way, Leonardtown, MD 20650
    23701 Robert Way, Leonardtown, MD 20650
    23701 Robert Way, Leonardtown, MD 20650
    /74

    $3,250 per month

    • 5 Beds
    • 4.5 Baths
    • 4,836 Sq Ft
    • House for Rent

    23701 Robert Way, Leonardtown, MD 20650

    Welcome to the Villages at Leonardtown! This charming and spacious home offers the perfect blend of comfort and style. Situated in a tranquil neighborhood, this property features 4 bedrooms and 4.5 bathrooms, providing ample space for family and guests. Step inside to discover a bright and inviting living area with large windows that flood the space with natural light. The open-concept kitchen

    Claudia Lodge RE/MAX One

    23701 Robert Way, Leonardtown, MD 20650
  • 23280 Hollywood Rd, Leonardtown, MD 20650
    23280 Hollywood Rd, Leonardtown, MD 20650
    23280 Hollywood Rd, Leonardtown, MD 20650
    /20

    $330,000 Sold Sep 16, 2025

    • 1,402 Sq Ft
    • $235/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    23280 Hollywood Rd, Leonardtown, MD 20650

    Charming Brick Home in Downtown Leonardtown!All-brick 3BR, 1,400 sq ft home on a 1/2-acre lot with public water and sewer. Features new windows, roof, and gutters, plus a spacious living/dining combo and family room.Walk to restaurants & shops—prime location in the heart of town! Estate sale. Subject to Orphan's court approval.

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23280 Hollywood Rd, Leonardtown, MD 20650
    • 41493 Margrove Cir, Leonardtown, MD 20650
      41493 Margrove Cir, Leonardtown, MD 20650
      41493 Margrove Cir, Leonardtown, MD 20650
      /32

      Est $441,216 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
  • 23670 Dragonfly Ln, Leonardtown, MD 20650
    23670 Dragonfly Ln, Leonardtown, MD 20650
    23670 Dragonfly Ln, Leonardtown, MD 20650
    /48

    $445,900 Under Contract

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

    23670 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company.Unit 87 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior

    Laura Bernth RE/MAX One

    23670 Dragonfly Ln, 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
  • 21784 Potomac View Dr, Leonardtown, MD 20650
    21784 Potomac View Dr, Leonardtown, MD 20650
    /2

    $287,000 Sold Sep 15, 2025

    • 1,056 Sq Ft
    • $272/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1962

    21784 Potomac View Dr, Leonardtown, MD 20650

    Society Hill fixer-upper: 3 BR, 1 BA, approx. 1,100 sq ft, attached 1-car garage. Ready for updates—great potential to renovate and make it your own! Optional Breton Bay Community Association membership offers beach, pool, tennis, and golf access (membership/fees apply). Property details are estimated; buyer to verify all information. Just a short walk to the neighborhood beach, pier, and picnic

    Mike Benton Home Towne Real Estate

    21784 Potomac View Dr, Leonardtown, MD 20650
    • 23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      /72

      Est $675,347 Not Listed For Sale

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

      23748 Coventry Dr, Leonardtown, MD 20650

      23748 Coventry Dr, Leonardtown, MD 20650
  • 23676 Dragonfly Ln, Leonardtown, MD 20650
    23676 Dragonfly Ln, Leonardtown, MD 20650
    23676 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $445,900 Open Sat 1PM - 3:45PM

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    23676 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company.Unit 88 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison

    Laura Bernth RE/MAX One

    23676 Dragonfly Ln, Leonardtown, MD 20650
  • 43840 Tarrywyle Way, Leonardtown, MD 20650
    43840 Tarrywyle Way, Leonardtown, MD 20650
    43840 Tarrywyle Way, Leonardtown, MD 20650
    /42

    $5,000 per month

    • 6 Beds
    • 5 Baths
    • 5,278 Sq Ft
    • House for Rent

    43840 Tarrywyle Way, Leonardtown, MD 20650

    Tatiana Bell Quasar Property Management And Real Estate LLC

    43840 Tarrywyle Way, Leonardtown, MD 20650
  • 22530 Bull Rd, Leonardtown, MD 20650
    22530 Bull Rd, Leonardtown, MD 20650
    22530 Bull Rd, Leonardtown, MD 20650
    /27

    $575,000 Sold Sep 12, 2025

    • 1,976 Sq Ft
    • $291/SF
    • 3 Beds
    • 3 Baths
    • Built 1971

    22530 Bull Rd, Leonardtown, MD 20650

    Beautiful park-like setting on 8 acres featuring a family home and the unique Three Bears House! The main residence, built and lovingly cared for by the original owner, offers 3 bedrooms with hardwood floors and 2 full baths on the main level. A walk-out lower level includes a 3rd full bath, kitchenette, and spacious family room with a woodstove—ideal for gatherings or separate living

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    22530 Bull Rd, Leonardtown, MD 20650
    • 23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      /71

      Est $719,494 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
  • 42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    /49

    $559,900

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    42043 Starlight Dr, Leonardtown, MD 20650

    Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has all-new flooring and a freshly painted interior. A bright and cheery home with four spacious bedrooms on the upper level, with generous closets. Convenient laundry on this upper level. The main floor features an oversized great room, a kitchen with solid surface counters, and a garden window over the kitchen

    Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, Leonardtown, MD 20650
  • 23330 Lindsay Dr, Leonardtown, MD 20650
    23330 Lindsay Dr, Leonardtown, MD 20650
    23330 Lindsay Dr, Leonardtown, MD 20650
    /26

    $584,000 Sold Sep 12, 2025

    • 1,926 Sq Ft
    • $303/SF
    • 0 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2022

    23330 Lindsay Dr, Leonardtown, MD 20650

    COMING SOON!!!! Rare opportunity in Clark's Rest. This beautiful home was built in 2022 and still looks and feels brand new!! This rear load garage home features 3 bedrooms/2 baths on the main level with just over 1880 sq feet of finished living space to enjoy. Basement is unfinished but does have a finished full bath and a window well perfect for a future bedroom opportunity. This

    Kristen Quinn Realty Navigator

    23330 Lindsay Dr, Leonardtown, MD 20650
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $535,359 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
  • 41435 Osborne Ln, Leonardtown, MD 20650
    41435 Osborne Ln, Leonardtown, MD 20650
    41435 Osborne Ln, Leonardtown, MD 20650
    /59

    $675,000

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

    41435 Osborne Ln, Leonardtown, MD 20650

    Built in 2018, this home feels better than new with fresh paint and modern updates throughout! With 6 bedrooms, 4.5 bathrooms, and multiple living spaces, there’s room for every member of the household, long-term guests, or effortless entertaining. Osborne Lane greets you with a welcoming front porch and porch swing to enjoy mornings or evenings overlooking the tree-lined, sidewalked streets.

    Delaney Burgess RE/MAX United Real Estate

    41435 Osborne Ln, Leonardtown, MD 20650
  • 22064 Daffodil Ct, Leonardtown, MD 20650
    22064 Daffodil Ct, Leonardtown, MD 20650
    22064 Daffodil Ct, Leonardtown, MD 20650
    /82

    $701,650 Sold Sep 11, 2025

    • 5,012 Sq Ft
    • $140/SF
    • 43 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2022

    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
    • 23567 Pine Bluff Way, Leonardtown, MD 20650
      23567 Pine Bluff Way, Leonardtown, MD 20650
      23567 Pine Bluff Way, Leonardtown, MD 20650
      /69

      Est $641,286 Not Listed For Sale

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

      23567 Pine Bluff Way, Leonardtown, MD 20650

      23567 Pine Bluff Way, Leonardtown, MD 20650
  • 20814 Deer Wood Park Dr, Leonardtown, MD 20650
    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    /53

    $569,000

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft

    20814 Deer Wood Park Dr, Leonardtown, MD 20650

    This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy on a beautifully treed 4 acre lot. The first floor features a private office/den, formal living room, and elegant dining room. The large kitchen includes a cozy breakfast nook and opens to a step-down family room with a slider leading to a screened-in porch—ideal for indoor-outdoor living.Upstairs,

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, Leonardtown, MD 20650
  • 21055 Breton Beach Ct, Leonardtown, MD 20650
    21055 Breton Beach Ct, Leonardtown, MD 20650
    21055 Breton Beach Ct, Leonardtown, MD 20650
    /71

    $1,215,200 Sold Sep 08, 2025

    • 3,052 Sq Ft
    • $398/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    21055 Breton Beach Ct, Leonardtown, MD 20650

    Tucked away on nearly four acres of waterfront privacy along protected Breton Bay, this exceptional Leonardtown estate offers the perfect blend of comfort, craftsmanship, and coastal lifestyle. With approximately 150 feet of shoreline, the property’s elevated positioning above the waterline provides both added protection and sweeping water views. A beautifully constructed rip rap revetment

    Robert Gauger EXP Realty, LLC

    21055 Breton Beach Ct, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 18

Maryland St Marys County Leonardtown

Real Estate & Homes

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 29 days on the market compared to the national average of 52 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $544,950, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$544,950
Median Single Family Sale Price
$589,950
Median Townhouse Sale Price
$437,500
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$199
Number of Homes for Sale
32
Last 12 months Home Sales
140
Months of Supply
2.70
Median List Price
$556,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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