6,717

Leonardtown, MD Homes

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  • 41832 Foxwell Point Ln, Leonardtown, MD 20650
    41832 Foxwell Point Ln, Leonardtown, MD 20650
    41832 Foxwell Point Ln, Leonardtown, MD 20650
    /43

    $800,000

    • 3 Beds
    • 4 Baths
    • 3,683 Sq Ft

    41832 Foxwell Point Ln, Leonardtown, MD 20650

    Discover this stunning cedar siding contemporary waterfront home offering a perfect blend of comfort and character. Enjoy water access with a private shared dock, ideal for relaxing days on the water. Freshly painted throughout with brand-new flooring in basement and two bedrooms, this home shines inside and out.The sunroom features beautiful slate floors and peaceful views of the surrounding

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (227) 238-0627

    41832 Foxwell Point Ln, Leonardtown, MD 20650
  • 20670 Bloombury Ln, Leonardtown, MD 20650
    20670 Bloombury Ln, Leonardtown, MD 20650
    20670 Bloombury Ln, Leonardtown, MD 20650
    /18

    $3,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,434 Sq Ft
    • House for Rent

    20670 Bloombury Ln, Leonardtown, MD 20650

    Secluded home in Leonardtown area. Wrap around porch, garage, and plenty of area to spread out. 3 bedrooms on upper level one bedroom or office on main level. Unfinished basement and garage. Lots of outside room to roam and explore nature.

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (227) 234-0617

    20670 Bloombury Ln, Leonardtown, MD 20650
  • 43107 Gum Spring Dr, Leonardtown, MD 20650
    43107 Gum Spring Dr, Leonardtown, MD 20650
    43107 Gum Spring Dr, Leonardtown, MD 20650
    /60

    $625,000 Sold Nov 26, 2025

    • 2,742 Sq Ft
    • $228/SF
    • 11 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1993

    43107 Gum Spring Dr, Leonardtown, MD 20650

    Nestled in prestigious Chestnut Ridge, this exquisite Colonial home offers a harmonious blend of elegance and comfort. Set on a sprawling 5.33-acre, wooded lot, the property invites you to experience a lifestyle of tranquility and sophistication. The heart of the home features a charming brick fireplace, perfect for cozy evenings, while the spacious layout provides ample room for entertaining and

    Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, 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 $527,455 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
  • 21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    /31

    $465,000

    • 3 Beds
    • 2 Baths
    • 2,527 Sq Ft

    21925 Budds Creek Rd, Leonardtown, MD 20650

    This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family room with wood stove insert, large laundry room, and accessory area on the lower level. Also has a 2 Car Detached garage built in 2008. Roof of garage and house was re-shingled in 2020 with 50 year shingles. The HVAC was regularly serviced.

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (227) 230-5161

    21925 Budds Creek Rd, Leonardtown, MD 20650
  • 44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    /32

    $2,175 - $2,575 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
  • 23730 Dragonfly Ln, Leonardtown, MD 20650
    23730 Dragonfly Ln, Leonardtown, MD 20650
    23730 Dragonfly Ln, Leonardtown, MD 20650
    /58

    $459,900 Sold Nov 25, 2025

    • 18 Days On Market
    • 4 Beds
    • 3.5 Baths

    23730 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 97 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 Oakley D1

    Laura Bernth RE/MAX One

    23730 Dragonfly Ln, Leonardtown, MD 20650
    • 22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      /36

      Est $452,438 Not Listed For Sale

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

      22605 Calvert St, Leonardtown, MD 20650

      22605 Calvert St, 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

    $470,000 Pending

    • 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 chef.

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (240) 697-2564

    40534 Miss Ettas Way, Leonardtown, MD 20650
  • 23067 Town Run Dr, Leonardtown, MD 20650
    23067 Town Run Dr, Leonardtown, MD 20650
    23067 Town Run Dr, Leonardtown, MD 20650
    /43

    $3,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,720 Sq Ft
    • House for Rent

    23067 Town Run Dr, Leonardtown, MD 20650

    For rent is this beautifully maintained "Mattingly" from the Village Series. This home plan features 4BR/2.5BA and a full unfinished basement with rough-in for future bath. The Mattingly Model is a two-story that features a Grand Kitchen equipped with large island, double ovens, and pantry. The owner's suite includes QBH's signature Deluxe Shower (4.5'x7' tiled shower with 2 shower heads, and

    Matthew Burgan Infinitas Realty Group

    23067 Town Run Dr, Leonardtown, MD 20650
  • 23712 Dragonfly Ln, Leonardtown, MD 20650
    23712 Dragonfly Ln, Leonardtown, MD 20650
    23712 Dragonfly Ln, Leonardtown, MD 20650
    /51

    $469,900 Sold Nov 25, 2025

    • 4 Beds
    • 3.5 Baths

    23712 Dragonfly Ln, Leonardtown, MD 20650

    ***UNDER CONTRACT***Unit 94 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

    23712 Dragonfly Ln, Leonardtown, MD 20650
    • 23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      /72

      Est $682,378 Not Listed For Sale

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

      23748 Coventry Dr, Leonardtown, MD 20650

      23748 Coventry Dr, Leonardtown, MD 20650
  • 22539 Landing Way, Leonardtown, MD 20650
    22539 Landing Way, Leonardtown, MD 20650
    22539 Landing Way, Leonardtown, MD 20650
    /32

    $520,000 Under Contract

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

    22539 Landing Way, Leonardtown, MD 20650

    Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the

    Agent Photo

    Trish Brow

    EXP Realty, LLC

    (227) 999-1015

    22539 Landing Way, Leonardtown, MD 20650
  • 22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    /15

    $1,650 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, parking for two cars and access to a large side

    22645 Washington St, Leonardtown, MD 20650
  • 21745 Pinehurst Ct, Leonardtown, MD 20650
    21745 Pinehurst Ct, Leonardtown, MD 20650
    21745 Pinehurst Ct, Leonardtown, MD 20650
    /82

    $610,000 Sold Nov 21, 2025

    • 2,860 Sq Ft
    • $213/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1991

    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

    Patrick Deighan CENTURY 21 New Millennium

    21745 Pinehurst Ct, Leonardtown, MD 20650
    • 23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      /71

      Est $715,960 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
  • 19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    /13

    $130,000 Under Contract

    • 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
  • 40905 Spring House Ln, Leonardtown, MD 20650
    40905 Spring House Ln, Leonardtown, MD 20650
    40905 Spring House Ln, Leonardtown, MD 20650
    /50

    $3,000 per month

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft
    • House for Rent

    40905 Spring House Ln, Leonardtown, MD 20650

    Welcome to 40905 Spring House Ln, Leonardtown, MD 20650. This beautifully renovated, modern country themed home offers comfort, charm, and convenience in one of Southern Maryland’s most desirable communities. This cozy, retreat has been thoughtfully updated with warm rustic accents and contemporary finishes, creating an inviting atmosphere that instantly feels like home. Bright open spaces,

    Michael Hunter Real Broker, LLC

    40905 Spring House Ln, Leonardtown, MD 20650
  • 44504 Watson Ln, Leonardtown, MD 20650
    44504 Watson Ln, Leonardtown, MD 20650
    44504 Watson Ln, Leonardtown, MD 20650
    /36

    $465,000 Sold Nov 21, 2025

    • 2,304 Sq Ft
    • $202/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    44504 Watson Ln, Leonardtown, MD 20650

    This 3 bed, 2 bath Cape Cod in the Leonardtown district offers a comfortable secluded setting, removed from the major commercial thruways of the county. The property includes over 2 acres of land, with a cleared, grassy front and rear yard, surrounded by forest on all sides. Inside, there is a large country kitchen with stainless steel appliances and a large living room filled with natural light.

    Danny Morris O'Brien Realty ERA Powered

    44504 Watson Ln, Leonardtown, MD 20650
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $507,950 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
  • 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

    $689,900

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

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    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 come true for boaters and anglers alike.Inside, you’ll find a

    Agent Photo

    Mileah Walker

    Real Broker, LLC

    (227) 240-6440

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • 39564 Potomac Ave, Leonardtown, MD 20650
    39564 Potomac Ave, Leonardtown, MD 20650
    39564 Potomac Ave, Leonardtown, MD 20650
    /9

    $2,200 per month

    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • House for Rent

    39564 Potomac Ave, Leonardtown, MD 20650

    Property Id: 1255022Fully renovated rambler on corner lot with in quiet neighborhood. Rental has 3 bedrooms, 1.5 bathrooms and a screened in porch. Conveniently located near Leonardtown schools, restaurants, shopping & entertainment. Washer, dryer, and shed for extra storage are also included. Small pets on case-by-case basis.

    39564 Potomac Ave, Leonardtown, MD 20650
  • 21515 Our Drive Way, Leonardtown, MD 20650
    21515 Our Drive Way, Leonardtown, MD 20650
    21515 Our Drive Way, Leonardtown, MD 20650
    /70

    $492,000 Sold Nov 21, 2025

    • 1,848 Sq Ft
    • $266/SF
    • 2 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1988

    21515 Our Drive Way, Leonardtown, MD 20650

    Charming 4 bedroom 2 full bath Cape Cod on a 5.27 acre lot in Leonardtown! This adorable home is ready for a new owner just in time for the holidays. As you drive up to the house the expansive lot opens up to the beautiful front porch and entry into the home. Hard wood floors throughout the main level. The living room is spacious and has a brick fireplace with a wood insert. Perfect for cozy

    Kelly Padgett CENTURY 21 New Millennium

    21515 Our Drive Way, 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 $638,601 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
  • 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
  • 23398 Hollywood Rd, Leonardtown, MD 20650
    23398 Hollywood Rd, Leonardtown, MD 20650
    23398 Hollywood Rd, Leonardtown, MD 20650
    /10

    $1,900 per month

    • 2 Beds
    • 1 Bath
    • 1,308 Sq Ft
    • House for Rent

    23398 Hollywood Rd, Leonardtown, MD 20650

    Welcome to 23398 Hollywood Rd, Leonardtown, MD - where charm and convenience meet in this adorable 2-bed, 1-bath home. Step into the warmth of wood floors throughout the main living area, creating a cozy and inviting atmosphere. The main floor laundry adds a touch of modern convenience to this classic gem. The spacious backyard is a haven for relaxation and outdoor activities, with a back deck

    Matthew Burgan Infinitas Realty Group

    23398 Hollywood Rd, Leonardtown, MD 20650
  • 21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    /4

    $163,500 Sold Nov 20, 2025

    • 1,144 Sq Ft
    • $143/SF
    • 37 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    21983 Point Lookout Rd, Leonardtown, MD 20650

    ONLINE AUCTION: Bidding begins 10/07/2025 @ 10:00 AM. Bidding ends 10/09/2025 @ 12:25 PM. List Price is Suggested Opening Bid. Deposit: $15,000. Single Family Home located in the Belvidere Woodland area. Located on +/- 40,000 SF of land, this property is JUST MINUTES to the St. Mary's State Park. Easy access to major traffic artery St. Andrew's Church Rd.

    Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, 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 $778,688 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
  • Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
    /49

    $449,900 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths

    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, Receive $10,000 in 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. (Must Settle In 2025!) Unit 95 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes!

    Laura Bernth RE/MAX One

    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
  • 22397 Armstrong Dr, Leonardtown, MD 20650
    22397 Armstrong Dr, Leonardtown, MD 20650
    22397 Armstrong Dr, Leonardtown, MD 20650
    /45

    $2,800 per month

    • 3 Beds
    • 3 Baths
    • 2,331 Sq Ft
    • House for Rent

    22397 Armstrong Dr, Leonardtown, MD 20650

    **Now Accepting Housing Vouchers** Just 7 minutes from the Leonardtown Square & Wharf, St. Mary's Hospital. 10 minutes from the beaches & trails of Newtowne Neck State Park. Armstrong Drive is located in the charming Breton Bay community. This delightful split-level home offers a perfect blend of comfort and convenience. Students are served by Benjamin Banneker Elementary School and Leonardtown

    Jonathan Powell Real Broker, LLC

    22397 Armstrong Dr, Leonardtown, MD 20650
  • 41435 Osborne Ln, Leonardtown, MD 20650
    41435 Osborne Ln, Leonardtown, MD 20650
    41435 Osborne Ln, Leonardtown, MD 20650
    /59

    $665,000 Sold Nov 20, 2025

    • 4,145 Sq Ft
    • $160/SF
    • 21 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2018

    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
    • 23930 Susies Ln, Leonardtown, MD 20650
      23930 Susies Ln, Leonardtown, MD 20650
      23930 Susies Ln, Leonardtown, MD 20650
      /77

      Est $509,884 Not Listed For Sale

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

      23930 Susies Ln, Leonardtown, MD 20650

      23930 Susies Ln, Leonardtown, MD 20650
  • Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $447,400 Pending

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

    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650

    ***MOVE IN READY***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 D2,

    Laura Bernth RE/MAX One

    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
  • 42271 Bird Haven Dr, Leonardtown, MD 20650
    42271 Bird Haven Dr, Leonardtown, MD 20650
    42271 Bird Haven Dr, Leonardtown, MD 20650
    /51

    $3,200 per month

    • 5 Beds
    • 3.5 Baths
    • 3,448 Sq Ft
    • House for Rent

    42271 Bird Haven Dr, Leonardtown, MD 20650

    Gorgeous 5 Bedroom 3.5 Bathroom Colonial w/ 3500sqft of Finished Living Space, a 2 Car Garage, & a pool! Solar Panels are a nice touch that will help keep the utility bills low! Home is situated in a well kept community within the Leonardtown High School District. Driving up you notice the charming curb appeal & cozy front porch! Entering into the foyer you will find a formal living room & dining

    Mark Frisco CENTURY 21 New Millennium

    42271 Bird Haven Dr, Leonardtown, MD 20650
  • 22305 Hanover Dr, Leonardtown, MD 20650
    22305 Hanover Dr, Leonardtown, MD 20650
    22305 Hanover Dr, Leonardtown, MD 20650
    /57

    $629,000 Sold Nov 18, 2025

    • 3,404 Sq Ft
    • $185/SF
    • 7 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2005

    22305 Hanover Dr, Leonardtown, MD 20650

    Welcome to your ideal home in the sought-after Hanover at Breton Bay! This beautiful, spacious home shines with thoughtful design, featuring hardwood floors that flow through a bright, open-concept layout and a striking two-story foyer. The well-appointed kitchen is a cook’s dream, with ample cabinetry, generous countertops, a spacious center island, and a cozy breakfast nook, effortlessly

    Tracey Summers CENTURY 21 New Millennium

    22305 Hanover Dr, Leonardtown, MD 20650
    • 23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      /44

      Est $435,578 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
  • Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    /49

    $445,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 96-23724 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 96 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

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
  • 21692 Potomac View Dr, Leonardtown, MD 20650
    21692 Potomac View Dr, Leonardtown, MD 20650
    21692 Potomac View Dr, Leonardtown, MD 20650
    /48

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 2,050 Sq Ft
    • House for Rent

    21692 Potomac View Dr, Leonardtown, MD 20650

    Brick 3 bedroom/2 bath rambler on a half acre lot in beautiful water-oriented Breton Bay/Society Hill. This home offers lots of space, washer/dryer, a level, clear yard, storage sheds, and a circular driveway. Plenty of places to walk/bike, as well as a community beach/pier to kayak from, and a picnic area/pavilion. Membership available at the nearby Breton Bay Golf and Country Club -- featuring

    Brooke Matthews RE/MAX One

    21692 Potomac View Dr, Leonardtown, MD 20650
  • 23534 Belmar Dr, Leonardtown, MD 20650
    23534 Belmar Dr, Leonardtown, MD 20650
    23534 Belmar Dr, Leonardtown, MD 20650
    /45

    $639,000 Sold Nov 17, 2025

    • 4,738 Sq Ft
    • $135/SF
    • 96 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2008

    23534 Belmar Dr, Leonardtown, MD 20650

    **Back on the market after buyer failed to perform.** **Price reduced and now below recent appraised value**, 23534 Belmar Drive is your opportunity to own a beautifully maintained, move-in-ready home in the sought-after Leonard’s Grant community of Leonardtown. With over 5,000 sq ft of finished living space, this impressive residence offers 5 spacious bedrooms, 3.5 baths, and an ideal layout for

    Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
    • 40840 Greenwood Ln, Leonardtown, MD 20650
      40840 Greenwood Ln, Leonardtown, MD 20650
      40840 Greenwood Ln, Leonardtown, MD 20650
      /70

      Est $772,888 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,320 Sq Ft

      40840 Greenwood Ln, Leonardtown, MD 20650

      40840 Greenwood Ln, 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 38 days on the market compared to the national average of 53 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $542,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$542,500
Median Single Family Sale Price
$586,925
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$196
Number of Homes for Sale
25
Last 12 months Home Sales
158
Months of Supply
1.90
Median List Price
$549,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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