6,684

Leonardtown, MD Homes

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  • /53

    $442,500 Sold Mar 25, 2025

    • 2,680 Sq Ft
    • $165/SF
    • 30 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1975

    22380 White Oak Rd, Leonardtown, MD 20650

    Welcome to your dream home in the highly sought-after Breton Bay community of Leonardtown, Maryland! This property is a true standout, with major repairs and thoughtful upgrades already done to provide ultimate comfort and peace of mind. At the top of the list are a brand-new septic system and a new roof, alongside a host of enhancements including a fenced rear yard, leaf guards, a new roof on

    Diana Washabaugh CENTURY 21 New Millennium

    22380 White Oak Rd, Leonardtown, MD 20650
    • /45

      Est $423,357 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,728 Sq Ft

      21126 Arbor Ct, Leonardtown, MD 20650

      21126 Arbor Ct, Leonardtown, MD 20650
  • /31

    $665,000

    • 4 Beds
    • 3.5 Baths
    • 3,858 Sq Ft

    23266 Clarks Rest Rd, Leonardtown, MD 20650

    This gorgeous Pinehurst model in Clark's Rest community is not going to last long! This home has 4BR/3.5BA located on large corner home site, Open floor plan, with upgraded Kitchen appliances and gas cook-top and granite counter tops. Hardwood flooring throughout , upgraded lighting with recessed lighting in the kitchen, large walk-in Pantry, freshly painted walls, separate formal dining room,

    Kelly Padgett CENTURY 21 New Millennium

    23266 Clarks Rest Rd, Leonardtown, MD 20650
  • /4

    $483,000 Sold Mar 24, 2025

    • 2,645 Sq Ft
    • $183/SF
    • 4 Beds
    • 3.5 Baths
    • Built 2019

    41482 Margrove Cir, Leonardtown, MD 20650

    This home is the perfect choice in Clarks Rest! It features the expansive Callaway floor plan and offers a beautiful pond view. This end-unit townhome includes a 2-car rear-load garage, gas heating, a tankless water heater, and gas cooking. With 4 bedrooms and 3.5 baths, you will enjoy granite countertops in the kitchen, stainless steel appliances, and upgraded cabinetry. The spacious living area

    Chris Norris JR. Topside Realty

    41482 Margrove Cir, Leonardtown, MD 20650
    • /54

      Est $544,348 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,382 Sq Ft

      21137 Marigold St, Leonardtown, MD 20650

      21137 Marigold St, Leonardtown, MD 20650
  • /79

    $659,000

    • 5 Beds
    • 3.5 Baths
    • 4,738 Sq Ft

    23534 Belmar Dr, Leonardtown, MD 20650

    **SIGNIFICANT PRICE REDUCTION!** Now offered at more than $16,000 below the original list price, 23534 Belmar Drive presents a rare opportunity to own a luxurious, move-in-ready home in the prestigious Leonard’s Grant community of Leonardtown, MD. With over 5,000 square feet of refined living space, this exceptional residence combines elegant design, modern upgrades, and unmatched comfort in one

    Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
  • /23

    $285,000 Sold Mar 20, 2025

    • 1,669 Sq Ft
    • $171/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1966

    22239 Point Lookout Rd, Leonardtown, MD 20650

    Such a convenient location. Minutes from downtown Leonardtown, minutes from NAS Patuxent River. This property is has lots of space and a garage that offers so much. Relax on your front porch or back deck. High ceiling with skylights in super big family room. Primary bedroom exists to large rear deck. Garage has work space and air lines already in place. Oil heat keeps you warm on cold

    John Gatton CENTURY 21 New Millennium

    22239 Point Lookout Rd, Leonardtown, MD 20650
    • /50

      Est $285,388 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,008 Sq Ft

      22204 Nomoni St, Leonardtown, MD 20650

      22204 Nomoni St, Leonardtown, MD 20650
  • /3

    $95,000

    • Land
    • 0.84 Acre
    • $113,095 per Acre

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Prime Build-Ready Lot – Bring Your Dream Home to Life!Discover the perfect canvas for your dream home on this beautiful [size] acre lot in [location]! This perc-tested property is ready for construction, offering the flexibility to bring your own builder or partner with Graham & Co Custom Creations to design and build a custom home tailored to your vision.Located in a serene

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • /41

    $449,900 Sold Mar 14, 2025

    • 1,488 Sq Ft
    • $302/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1981

    21717 Meadow Ct, Leonardtown, MD 20650

    Custom passive solar home designed for energy efficiency and comfort. This thoughtfully updated home features a newly remodeled kitchen with new cabinets, countertops, and appliances, plus LVT flooring throughout. The primary and half baths have been completely renovated.An open floor plan enhances natural light, with a solarium featuring a tiled floor. Additional highlights include a

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    21717 Meadow Ct, Leonardtown, MD 20650
    • /76

      Est $678,708 Not Listed For Sale

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

      41488 Pensive St, Leonardtown, MD 20650

      41488 Pensive St, Leonardtown, MD 20650
  • /32

    $439,900 Open Sat 11AM - 1:30PM

    • 3 Beds
    • 3 Baths
    • 2,028 Sq Ft

    22362 Armstrong Dr, Leonardtown, MD 20650

    Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MDNestled in the desirable Society Hill neighborhood of Leonardtown, this one-of-a-kind property offers a rare opportunity with its expansive double lot—a true gem in the community. While the home retains a timeless charm, it presents an exciting chance to add your personal touch and modern updates.Inside, you'll find

    Chris Hill CENTURY 21 New Millennium

    22362 Armstrong Dr, Leonardtown, MD 20650
  • /27

    $460,000 Sold Mar 14, 2025

    • 2,084 Sq Ft
    • $221/SF
    • 15 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    41952 Loker Ct, Leonardtown, MD 20650

    Beautiful home in Academy Hills Neighborhood in Leonardtown! This home sits on the corner lot with a neighbor on one side and woods along the back. The location is convenient to town and Pax River but offers privacy and a quiet neighborhood without through traffic. The house features a living room, office, family room, eat in kitchen and dining room, laundry room, 4 spacious bedrooms, 2.5

    Diane Fenwick RE/MAX One

    41952 Loker Ct, Leonardtown, MD 20650
    • /70

      Est $675,774 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft

      21380 Fairwood Ct, Leonardtown, MD 20650

      21380 Fairwood Ct, 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 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is 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
  • /36

    $875,000 Sold Mar 14, 2025

    • 3,150 Sq Ft
    • $278/SF
    • 3 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1961

    21790 Cove Ln, Leonardtown, MD 20650

    Welcome to your dream waterfront retreat on Cherry Cove Creek! This stunning 3-bedroom, 3-bathroom rambler sits on 2.79 picturesque acres in Leonardtown, offering over 3,150 square feet of thoughtfully designed living space. As the seller is in the process of moving, professional interior photos are on the way, but you don’t have to wait to explore the incredible features of this home.The

    Mark Frisco CENTURY 21 New Millennium

    21790 Cove Ln, Leonardtown, MD 20650
    • /44

      Est $457,910 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,204 Sq Ft

      22480 Sparrow Ct, Leonardtown, MD 20650

      22480 Sparrow Ct, Leonardtown, MD 20650
  • /13

    $315,000

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

    20959 Redgate Ln, Leonardtown, MD 20650

    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 single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space and is

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • /90

    $961,000 Sold Mar 14, 2025

    • 4,416 Sq Ft
    • $218/SF
    • 14 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    40095 Greentree Dr, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY TUESDAY FEBRUARY 4th at 4:00 PM. Agents, please refer to agent remarks for offer instructions.Why wait for new construction? This like-new modern farmhouse is move-in ready and loaded with upgrades! Built by the highly requested Mednick Construction, this sale includes two lots totaling nearly 7 acres, offering ample space and privacy just outside downtown

    Sarah Mulford-Martin EXP Realty, LLC

    40095 Greentree Dr, Leonardtown, MD 20650
    • /42

      Est $535,190 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft

      21120 Someday Farm Ln, Leonardtown, MD 20650

      21120 Someday Farm Ln, Leonardtown, MD 20650
  • /6

    $169,900

    • Land
    • 1.49 Acres
    • $114,027 per Acre

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Charming Cul-de-Sac Lot in Breton Oaks – No HOA!Discover the perfect place to build your dream home on this beautiful, private lot located in the peaceful cul-de-sac of Breton Oaks. This small, custom-built subdivision offers a tranquil setting, with all homes in the neighborhood uniquely designed by St. Maries Builders. You can choose to build with them or bring your own builder to bring your

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /95

    $605,000 Sold Mar 14, 2025

    • 3,120 Sq Ft
    • $194/SF
    • 42 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2011

    22395 Hood Ln, Leonardtown, MD 20650

    Over the creek and through the woods to your new house we go!! Welcome to ultimate privacy yet such an extremely convenient location. You are just minutes from shopping, restaurants, PAX Naval Base and more! Every time you travel back home it will feel like you are headed to a retreat! New full-length rear deck added in 2024- 900 finished square feet. New fencing in rear yard for pet

    Jessica Raley CENTURY 21 New Millennium

    22395 Hood Ln, Leonardtown, MD 20650
    • /9

      Est $312,061 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft

      23038 Hopton Ln, Leonardtown, MD 20650

      23038 Hopton Ln, Leonardtown, MD 20650
  • /5

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! Both are presently rented. The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • /27

    $375,000 Sold Mar 07, 2025

    • 1,456 Sq Ft
    • $258/SF
    • 53 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    22395 Gore St, Leonardtown, MD 20650

    Discover the charm of 22395 Gore St, nestled in the sought-after town of Leonardtown! This delightful home features a sunroom filled with natural light, offering the perfect space to relax or entertain year-round. The well-appointed kitchen boasts abundant storage, ideal for staying organized while inspiring your culinary creativity. Generously sized rooms provide endless flexibility for living,

    William Rabbitt The Southside Group Real Estate

    22395 Gore St, Leonardtown, MD 20650
    • /63

      Est $735,578 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 5,258 Sq Ft

      23467 Lindsay Dr, Leonardtown, MD 20650

      23467 Lindsay Dr, Leonardtown, MD 20650
  • /29

    $999,900

    • Land
    • 10 Acres
    • $98,029 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this breathtaking 10.2-acre waterfront lot overlooking the serene Breton Bay. This rare gem is not just a piece of land; it's an invitation to create a life of adventure, tranquility, and natural beauty.Endless Possibilities:With perc approval already in place, this stunning property is ready for your dream home. Imagine waking up to stunning views

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • /28

    $305,000 Sold Feb 28, 2025

    • 1,040 Sq Ft
    • $293/SF
    • 1 Day On Market
    • 3 Beds
    • 1 Bath
    • Built 1971

    40315 Wathen Rd, Leonardtown, MD 20650

    This recently renovated rambler features three spacious bedrooms and one modern bathroom. Set on a flat half-acre lot, the property offers ample outdoor space for recreation, gardening, or however you see fit. The new septic tank ensures efficient waste management, enhancing the home's overall functionality. With its updated interiors and generous lot size, this residence combines comfort and

    Brian Mayer Samson Properties

    40315 Wathen Rd, Leonardtown, MD 20650
    • /39

      Est $446,677 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft

      41464 Helen Marie Ct, Leonardtown, MD 20650

      41464 Helen Marie Ct, Leonardtown, MD 20650
  • /2

    $225,000

    • Land
    • 8 Acres
    • $30,000 per Acre

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen. The

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, Leonardtown, MD 20650
  • /2

    $430,000 Sold Feb 25, 2025

    • 2,402 Sq Ft
    • $179/SF
    • 3 Beds
    • 3.5 Baths
    • Built 2014

    23259 Lindsay Dr, Leonardtown, MD 20650

    Location location location!! The Beautiful Town of Leonardtown offers Trolley Car transportation for those nights at the local winery or pub for example. This Former model Townhome offers Upgrades and plenty of space for a growing family if needed. Bsmt recreation room can be used as a bedroom and has a full bath. Garage located off Rec Room has room for 2 cars if needed along with paved

    Diana Divver Exit Landmark Realty

    23259 Lindsay Dr, Leonardtown, MD 20650
    • /90

      Est $707,071 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,748 Sq Ft

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      20746 Deer Wood Park Dr, Leonardtown, MD 20650
  • /6

    $24,900

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

    0 Long Leaf Ln Unit MDSM2012646, 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 MDSM2012646, Leonardtown, MD 20650
  • /109

    $655,000 Sold Feb 21, 2025

    • 2,469 Sq Ft
    • $265/SF
    • 110 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    40721 Merlin Way, Leonardtown, MD 20650

    This 4.5 acre lot features "Wooded Privacy" for this attractive two story in the lovely community of Avenmar. An inviting foyer greets you at the front door with the formal dining room on the right and the living room on the left. The family room is straight ahead and is open to the kitchen. The kitchen features custom cabinets, a large island, granite counter tops and stainless steel

    Ron Leonard Leonard Realty, Inc.

    40721 Merlin Way, Leonardtown, MD 20650
    • /55

      Est $537,800 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,546 Sq Ft

      23285 Joanne Dr, Leonardtown, MD 20650

      23285 Joanne Dr, Leonardtown, MD 20650
  • /3

    $175,000

    • Land
    • 8 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
  • /58

    $427,500 Sold Feb 20, 2025

    • 2,522 Sq Ft
    • $170/SF
    • 3 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2021

    41474 Marwood Cir, Leonardtown, MD 20650

    Offer deadline 1/6/2025 at noon. Welcome Home to this beautiful townhome located in Clarks Rest. Unit is less than 3 years young and is in immaculate condition. There is open space out of the front of the home and unit backs to trees in the rear for additional privacy. Open concept main level with all LVP flooring. Upgraded kitchen to include granite countertops and cabinets with soft close

    Cynthia Ballard CENTURY 21 New Millennium

    41474 Marwood Cir, Leonardtown, MD 20650
    • /50

      Est $673,938 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,540 Sq Ft

      39994 Ben Morgan Rd, Leonardtown, MD 20650

      39994 Ben Morgan Rd, Leonardtown, MD 20650
  • /3

    $180,000

    • Land
    • 1.87 Acres
    • $96,257 per Acre

    40533 Breton Knolls Ct, Leonardtown, MD 20650

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

    Mark Posey Greenmark Real Estate

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • /61

    $550,000 Sold Feb 18, 2025

    • 3,024 Sq Ft
    • $182/SF
    • 45 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2017

    23246 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this beautiful home nestled in the highly sought-after Clark Rest Subdivision in Leonardtown, Maryland. This charming neighborhood offers a wealth of amenities, including a pool, playground, basketball court, tennis court, and a community center. Additionally, the Leonardtown Trolley conveniently runs through the neighborhood during the summer and holiday seasons, providing easy access

    Jesieryl Hartzer CENTURY 21 New Millennium

    23246 Clarks Rest Rd, Leonardtown, MD 20650

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