6,716

Leonardtown, MD Homes

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    • /60

      Est $532,596 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,386 Sq Ft

      20947 Chestnut Ridge Dr, Leonardtown, MD 20650

      20947 Chestnut Ridge Dr, 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
    • /22

      Est $262,467 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      22264 Nomoni St, Leonardtown, MD 20650

      22264 Nomoni St, 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
    • /31

      Est $441,300 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,760 Sq Ft

      41850 Tomey Ct, Leonardtown, MD 20650

      41850 Tomey Ct, Leonardtown, MD 20650
  • /11

    $311,000 Sold Feb 12, 2025

    • 1,640 Sq Ft
    • $190/SF
    • 18 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1963

    21865 Rose Bank Rd, Leonardtown, MD 20650

    3 Bedroom 3 Bath Rambler situated on 2.5 acres. Level lot with plenty of potential. HUD MAKES NO REPAIRS. HUD CASE#243-006639). EQUAL HOUSING OPPORTUNITY. GROUND RENT/HOA/CONDO FEES/FF Fees if any to be verified by purchaser. All offers submitted to HUDHOMESTORE for bid status and availability visit HUDHOMESTORE.

    Christopher White Classic Select Inc

    21865 Rose Bank Rd, Leonardtown, MD 20650
    • /65

      Est $643,438 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,748 Sq Ft

      44143 Woodmont Dr, Leonardtown, MD 20650

      44143 Woodmont Dr, Leonardtown, MD 20650
  • /2

    $470,000 Sold Feb 11, 2025

    • 2,028 Sq Ft
    • $232/SF
    • 4 Beds
    • 3 Baths
    • Built 1978

    22355 White Oak Rd, Leonardtown, MD 20650

    COMING SOON! What you have been waiting for: A large colonial with a 1st floor bedroom. This house is located in Breton Bay Community which is a sought after neighborhood. Just move in and enjoy your privacy or choose to join into this active golf/waterfront community. Hoa is optional but with certain fees to you have access to the following (clubhouse, neighborhood beach, pool, playground, kayak

    Donna Thomas O'Brien Realty ERA Powered

    22355 White Oak Rd, Leonardtown, MD 20650
    • /68

      Est $590,643 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,358 Sq Ft

      21820 Hazeltine Ct, Leonardtown, MD 20650

      21820 Hazeltine Ct, Leonardtown, MD 20650
  • /40

    $414,980 Sold Feb 05, 2025

    • 1,560 Sq Ft
    • $266/SF
    • 3 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1985

    40778 S 40 Dr, Leonardtown, MD 20650

    Welcome to this beautiful Cape Cod home, offering 4 spacious bedrooms, 2 full baths, and a versatile flex room ideal as a home office or hobby space. Nestled in a sought-after water-access neighborhood, this home is perfect for enjoying both indoor and outdoor living.Inside, you'll find fresh paint, brand-new carpet, and new flooring throughout. The kitchen boasts of new appliances to

    Tracey Summers CENTURY 21 New Millennium

    40778 S 40 Dr, Leonardtown, MD 20650
    • /44

      Est $590,010 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 3,492 Sq Ft

      20760 Chestnut Ridge Dr, Leonardtown, MD 20650

      20760 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /42

    $740,000 Sold Feb 03, 2025

    • 5,716 Sq Ft
    • $129/SF
    • 13 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 2006

    41041 Knight Rd, Leonardtown, MD 20650

    This stunning estate is a true masterpiece, set on multiple acres of lush, meticulously landscaped grounds in one of the most sought-after neighborhoods. Boasting expansive living spaces both inside and out, this home offers unparalleled luxury and privacy. The sprawling property provides a sense of serenity and seclusion, yet remains conveniently close to top-tier schools, local beaches, and

    Connie Gunn CENTURY 21 New Millennium

    41041 Knight Rd, Leonardtown, MD 20650
    • /112

      Est $705,334 Not Listed For Sale

      • 3 Beds
      • 5 Baths
      • 3,712 Sq Ft

      40929 Falcon Way, Leonardtown, MD 20650

      40929 Falcon Way, Leonardtown, MD 20650
  • /47

    $375,000 Sold Jan 30, 2025

    • 2,286 Sq Ft
    • $164/SF
    • 10 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1989

    40459 Breton View Dr, Leonardtown, MD 20650

    Welcome to this charming 3-level end-unit townhouse in Breton Bay! Step inside to an open floor plan and unwind by the cozy wood-burning fireplace. Enjoy the screened-in porch or host a BBQ on the deck. The home features two primary bedrooms, a dining area, and an island kitchen with a pantry. The lower level, currently used as a recreational room with a closet and full bath, could easily serve

    Chris Norris JR. Topside Realty

    40459 Breton View Dr, Leonardtown, MD 20650
    • /36

      Est $474,795 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,304 Sq Ft

      21767 Potomac View Dr, Leonardtown, MD 20650

      21767 Potomac View Dr, Leonardtown, MD 20650
  • /45

    $260,000 Sold Jan 24, 2025

    • 768 Sq Ft
    • $339/SF
    • 19 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    22321 Leonard St, Leonardtown, MD 20650

    Charming Cottage in Water-Privileged St. Clements Bay Discover the serenity of life in this bright and airy cottage, nestled in the sought-after St. Clements Bay community. The home features tasteful updates to the kitchen and bath, blending modern convenience with cozy charm. The level lot includes a fully fenced backyard, perfect for relaxing or entertaining, with a handy shed for extra

    Lesa Clark Redfin Corp

    22321 Leonard St, Leonardtown, MD 20650
    • /8

      Est $238,859 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 736 Sq Ft

      42742 Moll Dyer Rd, Leonardtown, MD 20650

      42742 Moll Dyer Rd, Leonardtown, MD 20650
  • /73

    $579,900 Sold Jan 14, 2025

    • 3,726 Sq Ft
    • $156/SF
    • 27 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2018

    41431 Osborne Ln, Leonardtown, MD 20650

    Clark's Rest in Leonardtown offers a fantastic blend of convenience, recreation, and elegant living! This vibrant community is centrally located near local shops and dining, and residents enjoy access to impressive amenities, including a clubhouse, a spacious pool with water features and a dedicated kiddie pool, basketball and tennis courts, a tot lot, and playgrounds. Walking and biking trails

    Kimberly Page EXP Realty, LLC

    41431 Osborne Ln, Leonardtown, MD 20650
    • /48

      Est $682,194 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,498 Sq Ft

      22835 Avenmar Dr, Leonardtown, MD 20650

      22835 Avenmar Dr, Leonardtown, MD 20650
  • /44

    $639,900 Sold Jan 10, 2025

    • 3,080 Sq Ft
    • $208/SF
    • 24 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2024

    41541 Fairwood Ct, Leonardtown, MD 20650

    $20,000 SELLER CONCESSIONS TO BUYER!! MARRICK HOMES' PINEHURST IN CLARKS REST! MOVE IN NOW! Includes: Quartz Kitchen Countertops, Luxury Vinyl Planks, Stainless Steel Appliances, UPGRADED Cabinets throughout Kitchen & Baths, Separate Owner's Shower & Soaking Tub in Owner's Bath, and MUCH MORE! Clarks Rest community features an Outdoor Swimming Pool, Tennis Court, Basket Ball Court,

    Lynn Smithburger CENTURY 21 New Millennium

    41541 Fairwood Ct, Leonardtown, MD 20650
    • /38

      Est $483,829 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,291 Sq Ft

      21730 Lake Cir, Leonardtown, MD 20650

      21730 Lake Cir, Leonardtown, MD 20650
  • /79

    $625,000 Sold Jan 09, 2025

    • 3,129 Sq Ft
    • $200/SF
    • 151 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2010

    23636 Hansel Ct, Leonardtown, MD 20650

    Welcome to your dream home, where modern elegance meets everyday comfort in the highly sought-after community of Leonard's Grant, Leonardtown, MD. This stunning 4-bedroom, 2.5-bathroom home offers an exceptional lifestyle with thoughtfully designed spaces and premium finishes.Step inside to discover gleaming hardwood floors that flow seamlessly through a welcoming and versatile floor

    Chris Hill CENTURY 21 New Millennium

    23636 Hansel Ct, Leonardtown, MD 20650
    • /49

      Est $754,130 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,478 Sq Ft

      40728 Avenmar Ct, Leonardtown, MD 20650

      40728 Avenmar Ct, Leonardtown, MD 20650
  • /52

    $425,000 Sold Jan 08, 2025

    • 2,280 Sq Ft
    • $186/SF
    • 66 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1961

    20400 Chingville Rd, Leonardtown, MD 20650

    Buyer got cold feet! BACK ON THE MARKET! Discover your future at this picturesque property, set on a stunning 2 acre lot that feels like your own private park. With a freshly paved driveway and a beautiful stamped concrete walkway, this home is perfect for outdoor entertaining, relaxing with a good book, or hosting gatherings. Inside, this adorable two-level home has been completely updated from

    Delaney Burgess RE/MAX United Real Estate

    20400 Chingville Rd, Leonardtown, MD 20650
    • /30

      Est $514,103 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,450 Sq Ft

      21744 Potomac View Dr, Leonardtown, MD 20650

      21744 Potomac View Dr, Leonardtown, MD 20650
  • /63

    $420,000 Sold Jan 07, 2025

    • 2,896 Sq Ft
    • $145/SF
    • 11 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2014

    23255 Lindsay Dr, Leonardtown, MD 20650

    Discover modern living at its finest in this stunning, fully finished three-level townhouse in the heart of Leonardtown! This meticulously maintained home features a bright, open floor plan with the main level designed for easy gatherings. Enjoy beautiful hardwood floors throughout the main level, along with a sleek kitchen showcasing granite countertops, stainless steel appliances, and upgraded

    Jessica Raley CENTURY 21 New Millennium

    23255 Lindsay Dr, Leonardtown, MD 20650
    • /43

      Est $524,985 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,575 Sq Ft

      40761 Merlin Way, Leonardtown, MD 20650

      40761 Merlin Way, Leonardtown, MD 20650
  • /24

    $440,000 Sold Dec 30, 2024

    • 2,242 Sq Ft
    • $196/SF
    • 0 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1972

    40808 S 40 Dr, Leonardtown, MD 20650

    Charming contemporary rambler with a full basement, offering seasonal views of Breton Bay. The main level boasts an open living/dining area, a remodeled kitchen with new granite countertops (2024), and luxury vinyl plank flooring throughout. Recent updates include a new roof (2019), HVAC (2021), oil tank (2018), and gutters with leaf guards (2021). The home features replacement windows and added

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40808 S 40 Dr, Leonardtown, MD 20650
    • /97

      Est $1,631,306 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 6,814 Sq Ft

      40430 Breton Beach Rd, Leonardtown, MD 20650

      40430 Breton Beach Rd, Leonardtown, MD 20650
  • /91

    $525,000 Sold Dec 20, 2024

    • 3,602 Sq Ft
    • $146/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1990

    21733 Pinehurst Ct, Leonardtown, MD 20650

    Delightful, comfortable home with lots of upgrades, situated on a nice corner lot in a great neighborhood! All the spaces you need: living and family rooms, both with handsome stone fireplaces (one wood, one propane); remodeled kitchen with white cabinetry, gorgeous Brazilian granite countertops, and eating area; separate dining room with bay window. Hardwood flooring & ceramic tile, ceiling

    Patrick Deighan CENTURY 21 New Millennium

    21733 Pinehurst Ct, Leonardtown, MD 20650
    • /64

      Est $516,093 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,060 Sq Ft

      40797 Lake and Breton View Dr, Leonardtown, MD 20650

      40797 Lake and Breton View Dr, Leonardtown, MD 20650
  • /56

    $450,000 Sold Dec 20, 2024

    • 2,226 Sq Ft
    • $202/SF
    • 81 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    40907 Cooper Dr, Leonardtown, MD 20650

    Nestled in one of the most sought-after neighborhoods, this charming residence offers an inviting blend of warmth, comfort and cozy. Boasting 3 bedrooms and 2.5 baths, this home is perfect for both families and those who love to entertain. New Roof just installed! The moment you step inside, you're greeted by beautiful hardwood floors that flow throughout the main living areas, enhancing the

    Barbara Blades CENTURY 21 New Millennium

    40907 Cooper Dr, Leonardtown, MD 20650
    • /48

      Est $532,681 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 3,172 Sq Ft

      22520 Armstrong Dr, Leonardtown, MD 20650

      22520 Armstrong Dr, Leonardtown, MD 20650
  • /37

    $510,000 Sold Dec 20, 2024

    • 2,764 Sq Ft
    • $185/SF
    • 2 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2005

    22540 Landing Way, Leonardtown, MD 20650

    Walk ability in Saint Marys Count how amazing! This home is right next to Leonardtown Wharf. Walk to the restaurants, festivals, and Santa sightings in Leonardtown. The beautiful home has 3 decks and 2 balconies. It has an elevator. Freshly professionally painted. New light fixtures. New Flooring. It has a newer roof.

    Trish Brow EXP Realty, LLC

    22540 Landing Way, Leonardtown, MD 20650
    • /61

      Est $964,550 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,818 Sq Ft

      21625 Coves End Ct, Leonardtown, MD 20650

      21625 Coves End Ct, Leonardtown, MD 20650
  • /64

    $625,000 Sold Dec 20, 2024

    • 1,144 Sq Ft
    • $546/SF
    • 21 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1961

    40481 Old Breton Beach Rd, Leonardtown, MD 20650

    Price included TWO Separate deeded LOTS! TWO PIERS!!! One New Sectic. This Dream Waterfront Home is being sold as a Turn-Key Home. Upgraded, Updated, new A/C and Ready for You. Did I mention TWO PIERS!!! The additional lot includes electric and septic, & utilities, as it previously had a home on it. The lot is being sold as is. Total acreage for both lots is 1.66. House = 1.32 acres and the lot

    Dawn Riley RE/MAX One

    40481 Old Breton Beach Rd, Leonardtown, MD 20650
    • /63

      Est $662,312 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,013 Sq Ft

      43910 Woodmont Dr, Leonardtown, MD 20650

      43910 Woodmont Dr, Leonardtown, MD 20650
  • /25

    $279,000 Sold Dec 18, 2024

    • 1,056 Sq Ft
    • $264/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2008

    41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

    Experience the blend of comfort and convenience of the sought after "Foxwell Community" at this beautifully upgraded 2-bedroom, 1-bathroom condo located at 41800 Eastwick Lane #1303. With 1,056 square feet of living space, this one-owner home beams with pride of ownership. The interior features new hardwood flooring throughout and a full suite of new stainless steel appliances, complemented by an

    Kelly Niland Home Towne Real Estate

    41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650
    • /53

      Est $543,793 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,916 Sq Ft

      41555 Hame Ct, Leonardtown, MD 20650

      41555 Hame Ct, Leonardtown, MD 20650
  • /52

    $549,900 Sold Dec 17, 2024

    • 4,832 Sq Ft
    • $114/SF
    • 14 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2004

    23585 Abraham Dr, Leonardtown, MD 20650

    IMMACULATE! Beautiful 5-bedroom, 3.5-bath 4832 SQFT Colonial with a 2-car garage is ready to welcome you!As you arrive, the lovely landscaping and inviting front elevation immediately catch your eye. The architectural roof is just a few years old, and the fully fenced backyard sits on a generous 0.38-acre lot in Leonardtown.The charming front porch is perfect for enjoying quiet

    Mark Frisco CENTURY 21 New Millennium

    23585 Abraham Dr, Leonardtown, MD 20650

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