6,982

Homes in ZIP Code 20650

Section Image
    • 41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      /39

      Est $606,503 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,993 Sq Ft

      41419 Whimsical Ct, Leonardtown, MD 20650

      41419 Whimsical Ct, Leonardtown, MD 20650
  • 40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    /36

    $859,900 New Construction

    • 4 Beds
    • 2.5 Baths

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 square feet of luxury living. As you step inside, you are greeted by an open layout that radiates warmth and spaciousness. The heart of the home, a two-story family room with fireplace, is bathed in natural light, creating an inviting atmosphere for entertaining and relaxation. Cook gourmet

    Michele Posey RE/MAX Realty Group

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • 42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    /42

    $906,500 Sold Jul 18, 2025

    • 2,167 Sq Ft
    • $418/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    42239 Riverwinds Dr, Leonardtown, MD 20650

    Welcome to your waterfront retreat on the Potomac River! This well-maintained 3-bedroom, 2.5-bath rambler is perfectly situated on a level 1-acre lot with stunning panoramic water views from every rear-facing room, including all bedrooms. The spacious kitchen opens to a cozy family room with a wood-burning fireplace, ideal for relaxing or entertaining. Step out to the screened-in porch or

    Connie Fitzgerald RE/MAX One

    42239 Riverwinds Dr, Leonardtown, MD 20650
    • 23546 Belmar Dr, Leonardtown, MD 20650
      23546 Belmar Dr, Leonardtown, MD 20650
      23546 Belmar Dr, Leonardtown, MD 20650
      /74

      Est $630,023 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,548 Sq Ft

      23546 Belmar Dr, Leonardtown, MD 20650

      23546 Belmar Dr, Leonardtown, MD 20650
  • 40552 Breton Knolls Ct, Leonardtown, MD 20650
    40552 Breton Knolls Ct, Leonardtown, MD 20650
    40552 Breton Knolls Ct, Leonardtown, MD 20650
    /38

    $884,900 New Construction

    • 5 Beds
    • 2.5 Baths
    • 3,127 Sq Ft

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    To Be Built - A Breton Knolls exclusive offering. Be the first to call this to-be-built custom-crafted home yours! Located in the heart of Leonardtown on oversized lots, this new 24-lot subdivision offers an elegantly crafted home by well-known local builder, Litz Custom Homes. The Jackson floor plan perfectly combines the essence of a Colonial Farmhouse with a modern twist to include over 3,000

    Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
  • 41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    /54

    $531,000 Sold Jul 18, 2025

    • 2,420 Sq Ft
    • $219/SF
    • 5 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2012

    41699 Courthouse Dr, Leonardtown, MD 20650

    Welcome to 41699 Courthouse Drive, a well-maintained home tucked away on a private lot in the heart of historic Leonardtown. Offering comfort, space, and small-town charm, this property is perfectly positioned with no HOA, public water and sewer, and easy access to everything Leonardtown has to offer.Inside, you’ll find a bright kitchen with plenty of cabinetry, an inviting dining area,

    Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, Leonardtown, MD 20650
    • 41429 Challedon Way, Leonardtown, MD 20650
      41429 Challedon Way, Leonardtown, MD 20650
      41429 Challedon Way, Leonardtown, MD 20650
      /60

      Est $688,673 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,660 Sq Ft

      41429 Challedon Way, Leonardtown, MD 20650

      41429 Challedon Way, Leonardtown, MD 20650
  • 23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    /76

    $619,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,806 Sq Ft

    23092 Town Run Dr, Leonardtown, MD 20650

    Welcome home to The Meadows of Town Run, and this Montross floorplan built by QBHI. The Montross is an efficient floorplan with no wasted space. With 2600 sq ft of above grade living area, 4 bedrooms and 2.5 baths, this home lives comfortably for any family. The beautiful kitchen opens generously to both the living room and an extended morning room. The cozy deck, just off the morning room

    Robin Errington CENTURY 21 New Millennium

    23092 Town Run Dr, Leonardtown, MD 20650
  • 43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    /74

    $475,000 Sold Jul 15, 2025

    • 2,400 Sq Ft
    • $198/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    43985 Main Way Rd, Leonardtown, MD 20650

    HUGE COVERED FRONT PORCH (12X18) INVITES YOU TO THIS AMAZINGLY WELL MAINTAINED RAMBLER IN DESIRABLE LANEDON NEIGHBORHOOD WITH DEEDED WATER ACCESS! 3/4 BEDROOMS; 4TH BEDROOM/CRAFT ROOM HAS ACCESS TO UNFINISHED SPACE FOR STORAGE. HARDWOOD FLOORS IN ALL ROOMS EXCEPT KITCHEN AND FAMILY ROOM. FORMAL LIVING ROOM AND SEPARATE DINING ROOM; PERFECT FOR THOSE FAMILY GATHERINGS AND HOLIDAY DINNERS. GOOD

    Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, Leonardtown, MD 20650
    • 41895 Tomey Ct, Leonardtown, MD 20650
      41895 Tomey Ct, Leonardtown, MD 20650
      41895 Tomey Ct, Leonardtown, MD 20650
      /83

      Est $546,308 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,192 Sq Ft

      41895 Tomey Ct, Leonardtown, MD 20650

      41895 Tomey Ct, Leonardtown, MD 20650
  • 22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    /86

    $633,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,745 Sq Ft

    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
  • 23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    /47

    $660,000 Sold Jul 14, 2025

    • 4,306 Sq Ft
    • $153/SF
    • 10 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23278 Applewood Ln, Leonardtown, MD 20650

    Absolutely stunning home in a premier location! Welcome to 23278 Applewood Ln in the sought-after Clark’s Rest community, directly across from the pool, sports courts, and clubhouse! All 4,000 sqft of living space is in pristine condition. From the moment you enter, you will love all of the natural light throughout. The jewel of the home is the expansive kitchen, curated with upgrades for your

    Jonathan Benya EXP Realty, LLC

    23278 Applewood Ln, Leonardtown, MD 20650
    • 21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      /56

      Est $660,716 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft

      21147 Catnip Ct, Leonardtown, MD 20650

      21147 Catnip Ct, Leonardtown, MD 20650
  • 41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    /30

    $645,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft

    41430 Whimsical Ct, Leonardtown, MD 20650

    Price Improvement!!!! This home is a MUST SEE!!!!Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful updates throughout, this home is perfect for

    Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
  • 23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    /75

    $595,000 Sold Jul 11, 2025

    • 3,188 Sq Ft
    • $187/SF
    • 29 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2011

    23578 Pine Bluff Way, Leonardtown, MD 20650

    LOCATION...LOCATION...LOCATION! THIS LOVELY HAYDEN MODEL IS NESTLED RIGHT AT THE HEAD OF THE VILLAGE GREEN IN DESIRABLE LEONARD'S GRANT NEIGHBORHOOD. 3 BEDROOMS AND 2 FULL BATHS ON SECOND LEVEL AND A PARTIALLY FINISHED BASEMENT TO INCLUDE REC ROOM AND FULL BATH. UNFINISHED SPACE COULD BE FINISHED FOR THE 4TH BEDROOM OR GREAT STORAGE. OPEN FLOOR PLAN FEATURES HARDWOOD FLOORS, GRANITE

    Jennifer Mullennix CENTURY 21 New Millennium

    23578 Pine Bluff Way, Leonardtown, MD 20650
    • 41503 Affirmed Way, Leonardtown, MD 20650
      41503 Affirmed Way, Leonardtown, MD 20650
      41503 Affirmed Way, Leonardtown, MD 20650
      /80

      Est $695,383 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 5,065 Sq Ft

      41503 Affirmed Way, Leonardtown, MD 20650

      41503 Affirmed Way, Leonardtown, MD 20650
  • 43571 Bayberry Ct, Leonardtown, MD 20650
    43571 Bayberry Ct, Leonardtown, MD 20650
    43571 Bayberry Ct, Leonardtown, MD 20650
    /59

    $612,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft

    43571 Bayberry Ct, Leonardtown, MD 20650

    Gorgeous Colonial on a Beautifully Landscaped 4.26 Acre Premium Lot in the Sought After, Well-Established Neighborhood of Chestnut Ridge. A Welcoming Covered Front Porch leads to an Open Floor Plan with 9 Foot Ceilings and New Luxury Vinyl Plank (LVP) Flooring. Stylish Large Living Room with a Wood Burning Fireplace. Bright Kitchen with 48” Cabinetry, Gleaming Granite, and a Large Pantry. The

    Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
  • 23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    /88

    $685,000 Sold Jul 10, 2025

    • 4,267 Sq Ft
    • $161/SF
    • 6 Beds
    • 3.5 Baths
    • Built 2008

    23558 Belmar Dr, Leonardtown, MD 20650

    Beautiful house in the desired neighborhood of Leonard’s Grand in Leonardtown! This house has many unique characteristics! All new carpet! As you walk in to the hardwood entryway, you’ll notice the gorgeous staircase. This level includes a dining room, custom butler’s pantry and a large, upgraded kitchen. The transom windows are gorgeous and bring in a ton of natural light. These cabinets

    Heather Foster RE/MAX One

    23558 Belmar Dr, Leonardtown, MD 20650
    • 22555 Breton Bay Dr, Leonardtown, MD 20650
      22555 Breton Bay Dr, Leonardtown, MD 20650
      22555 Breton Bay Dr, Leonardtown, MD 20650
      /48

      Est $668,788 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,176 Sq Ft

      22555 Breton Bay Dr, Leonardtown, MD 20650

      22555 Breton Bay Dr, Leonardtown, MD 20650
  • 23647 Hansel Ct, Leonardtown, MD 20650
    23647 Hansel Ct, Leonardtown, MD 20650
    23647 Hansel Ct, Leonardtown, MD 20650
    /74

    $660,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,194 Sq Ft

    23647 Hansel Ct, Leonardtown, MD 20650

    GORGEOUS HOME ON A CUL DE SAC! HIGHLIGHTS: 2 NEW HVAC UNITS, RADON MITIGATION SYSTEM, IN GROUND SPRINKLERS, 2 TIER COMPOSITE DECK WITH PAVER PATIO, FENCE, ETC...This beautifully maintained QBH Newport model located in the sought-after Leonards Grant community is move in ready! Walk in to a welcoming entryway that opens to a few spacious rooms and a gourmet kitchen. The kitchen has

    Heather Foster RE/MAX One

    23647 Hansel Ct, Leonardtown, MD 20650
  • 40905 Knight Rd, Leonardtown, MD 20650
    40905 Knight Rd, Leonardtown, MD 20650
    40905 Knight Rd, Leonardtown, MD 20650
    /43

    $445,000 Sold Jul 08, 2025

    • 1,820 Sq Ft
    • $245/SF
    • 82 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    40905 Knight Rd, Leonardtown, MD 20650

    Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland!This charming home blends comfort and functionality with three spacious bedrooms, 2.5 baths, and a layout that’s perfect for both everyday living and entertaining.Set on a generous half-acre lot, the fully fenced backyard offers plenty of room to enjoy the outdoors. Whether you're hosting a summer barbecue or winding

    Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
    • 40772 Magee Dr, Leonardtown, MD 20650
      40772 Magee Dr, Leonardtown, MD 20650
      40772 Magee Dr, Leonardtown, MD 20650
      /38

      Est $487,958 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,258 Sq Ft

      40772 Magee Dr, Leonardtown, MD 20650

      40772 Magee Dr, Leonardtown, MD 20650
  • 20620 Laurel Ct, Leonardtown, MD 20650
    20620 Laurel Ct, Leonardtown, MD 20650
    20620 Laurel Ct, Leonardtown, MD 20650
    /43

    $687,900 Pending

    • 5 Beds
    • 3 Baths
    • 3,500 Sq Ft

    20620 Laurel Ct, Leonardtown, MD 20650

    Move Right In and Start Living the Leonardtown Lifestyle!Welcome to 20620 Laurel Court — where modern luxury meets small town charm on nearly 5 private acres in sought-after Leonardtown, Maryland. Nestled in a peaceful cul-de-sac, this thoughtfully reimagined home offers over 3,000 sq ft of exceptional living space with 5 bedrooms and 3 full baths — including a convenient main level

    Amy Gallo RE/MAX One

    20620 Laurel Ct, Leonardtown, MD 20650
  • 23055 Town Run Dr, Leonardtown, MD 20650
    23055 Town Run Dr, Leonardtown, MD 20650
    23055 Town Run Dr, Leonardtown, MD 20650
    /85

    $695,000 Sold Jul 02, 2025

    • 4,019 Sq Ft
    • $173/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    23055 Town Run Dr, Leonardtown, MD 20650

    Stunning Clarke Model by Quality Built HomesLocated in the desirable Meadows at Town Run, this 4-bedroom, 3.5-bath home offers over 4,000 square feet of living space, including a finished lower level. Built in 2021, this home is just a few years old and has been meticulously maintained.Enjoy a prime location with Duke Elementary and the library within walking distance, Downtown

    Laura Bernth RE/MAX One

    23055 Town Run Dr, Leonardtown, MD 20650
    • 21715 Pebble Beach Ct, Leonardtown, MD 20650
      21715 Pebble Beach Ct, Leonardtown, MD 20650
      21715 Pebble Beach Ct, Leonardtown, MD 20650
      /78

      Est $742,593 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,437 Sq Ft

      21715 Pebble Beach Ct, Leonardtown, MD 20650

      21715 Pebble Beach Ct, Leonardtown, MD 20650
  • 21039 Woodmere Dr, Leonardtown, MD 20650
    21039 Woodmere Dr, Leonardtown, MD 20650
    21039 Woodmere Dr, Leonardtown, MD 20650
    /10

    $595,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 4,112 Sq Ft

    21039 Woodmere Dr, Leonardtown, MD 20650

    ***COMING SOON*** More exterior and interior photos coming. Roof replaced December 2022, Septic last pumped in 2023, New air conditioning and Heat Pump replaced September 2023, 73 Gallon Hot water heater replaced in 2017. This spacious and well-maintained Colonial style home offers privacy and convenience, set on a secluded lot surrounded by trees with an open yard and a fully fenced

    Wayne & Christine Floyd RE/MAX Realty Group

    21039 Woodmere Dr, Leonardtown, MD 20650
  • 21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    /70

    $625,000 Sold Jul 02, 2025

    • 3,664 Sq Ft
    • $171/SF
    • 69 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1997

    21897 Fairway Dr, Leonardtown, MD 20650

    Qualified VA buyers using their own entitlement can assume the current 2.25% VA loan.Custom-Built Beauty Overlooking Breton Bay Golf Course! Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunning 5-bedroom, 2.5-bath custom-built home in the desirable Breton Bay community. This home is in impeccable condition with numerous upgrades—simply move right in and start enjoying luxury

    Matthew Burgan Infinitas Realty Group

    21897 Fairway Dr, Leonardtown, MD 20650
    • 40139 Combs Creek Way, Leonardtown, MD 20650
      40139 Combs Creek Way, Leonardtown, MD 20650
      40139 Combs Creek Way, Leonardtown, MD 20650
      /68

      Est $1,203,184 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,944 Sq Ft

      40139 Combs Creek Way, Leonardtown, MD 20650

      40139 Combs Creek Way, Leonardtown, MD 20650
  • 21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    /2

    $649,900 Open House 10/11

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Absolutely stunning home in Leonardtown’s sought-after Kingston Subdivision! Perched on a hill with mature trees, beautiful landscaping, and plenty of open yard space, this 5BR/3.5BA home boasts over $165K in upgrades. Enjoy new high-efficiency HVAC systems (2023 & 2025), architectural roof (2018), luxury vinyl plank flooring, gourmet kitchen with granite countertops, tile backsplash, Kraus sink

    James Marcum CENTURY 21 New Millennium

    21117 Catnip Ct, Leonardtown, MD 20650
  • 23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    /64

    $1,100,000 Sold Jul 01, 2025

    • 6,508 Sq Ft
    • $169/SF
    • 7 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2009

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650

    Exceptional Private Estate with Detached Efficiency Apartment, Greenhouse, & Extensive Upgrades.Beautifully maintained and thoughtfully updated, this 5 BR, 6.5 BA custom estate offers space, privacy, and versatility in a stunning setting. A long, private farm lane leads to a solar-powered gated entry and professionally landscaped grounds, including wooden and wire fencing designed with

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    • 42990 Baywood Place, Leonardtown, MD 20650
      42990 Baywood Place, Leonardtown, MD 20650
      42990 Baywood Place, Leonardtown, MD 20650
      /68

      Est $674,865 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,724 Sq Ft

      42990 Baywood Place, Leonardtown, MD 20650

      42990 Baywood Place, Leonardtown, MD 20650
  • 23849 Point Lookout Rd, Leonardtown, MD 20650
    23849 Point Lookout Rd, Leonardtown, MD 20650
    23849 Point Lookout Rd, Leonardtown, MD 20650
    /37

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft

    23849 Point Lookout Rd, Leonardtown, MD 20650

    Excellent one level living in Leonardtown just past the high school, NO HOA, and sits on 1.5 acres of land. Front door was replaced in 2018; the rest of the doors and windows were replaced in 2025. Newer shingles replaced in 2015, the hall bathroom updated in 2024. Kitchen features a center island, which leads to a large outdoor deck for grilling and entertaining. Washer and dryer is being " sold

    Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
  • 23433 Grovewood Ct, Leonardtown, MD 20650
    23433 Grovewood Ct, Leonardtown, MD 20650
    23433 Grovewood Ct, Leonardtown, MD 20650
    /78

    $519,000 Sold Jul 01, 2025

    • 2,804 Sq Ft
    • $185/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23433 Grovewood Ct, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest Community. *OPEN HOUSE* Saturday, May 3rd from 11-2.Welcome to this beautifully maintained, "nearly-new" end-unit townhome in the desirable Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views. The chef-inspired kitchen is a dream, showcasing granite countertops, a

    Wayne & Christine Floyd RE/MAX Realty Group

    23433 Grovewood Ct, Leonardtown, MD 20650
    • 24606 Pin Cushion Rd, Leonardtown, MD 20650
      24606 Pin Cushion Rd, Leonardtown, MD 20650
      24606 Pin Cushion Rd, Leonardtown, MD 20650
      /79

      Est $650,824 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,466 Sq Ft

      24606 Pin Cushion Rd, Leonardtown, MD 20650

      24606 Pin Cushion Rd, Leonardtown, MD 20650
  • 41535 Singletree Dr, Leonardtown, MD 20650
    41535 Singletree Dr, Leonardtown, MD 20650
    41535 Singletree Dr, Leonardtown, MD 20650
    /54

    $530,000 Open Sat 11:30AM - 1:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft

    41535 Singletree Dr, Leonardtown, MD 20650

    Welcome home to 41535 Singletree Dr. This beautiful colonial offers 4 bedrooms and 2.5 baths with laminate hardwood floors throughout the first level. NEW CARPET being installed on 9/22 and 9/23. The kitchen features quartz countertops and opens to a living room with a cozy gas fireplace, as well as a formal dining room and sitting area, perfect for gatherings and everyday living. Upstairs,

    Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
  • 41572 Briarwood Cir, Leonardtown, MD 20650
    41572 Briarwood Cir, Leonardtown, MD 20650
    41572 Briarwood Cir, Leonardtown, MD 20650
    /80

    $505,000 Sold Jun 30, 2025

    • 2,850 Sq Ft
    • $177/SF
    • 55 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    41572 Briarwood Cir, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest. Welcome to this beautifully maintained, nearly-new end-unit townhome in the sought-after Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views from both the rear and side.Step inside to a spacious main level featuring luxury vinyl plank flooring and a convenient bonus

    Wayne & Christine Floyd RE/MAX Realty Group

    41572 Briarwood Cir, Leonardtown, MD 20650
    • 22223 Monterey Place, Leonardtown, MD 20650
      22223 Monterey Place, Leonardtown, MD 20650
      22223 Monterey Place, Leonardtown, MD 20650
      /63

      Est $641,280 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,592 Sq Ft

      22223 Monterey Place, Leonardtown, MD 20650

      22223 Monterey Place, Leonardtown, MD 20650
  • 41650 Matthew Ct, Leonardtown, MD 20650
    41650 Matthew Ct, Leonardtown, MD 20650
    41650 Matthew Ct, Leonardtown, MD 20650
    /15

    $540,000

    • 4 Beds
    • 2.5 Baths
    • 2,230 Sq Ft

    41650 Matthew Ct, Leonardtown, MD 20650

    This home features 4 spacious Bedrooms, an open Kitchen & great room w/built-in TV Niche over the gas Fireplace. There is a full basement w/rough-in. A Walk-in jetted tub and electric stair chair have been added. The property has a large, level fenced back yard with raised garden beds and is at the end of a cul-de-sac! The back deck provides space for cooking out and private entertaining.

    Paula Turner Pax River Realty LLC

    41650 Matthew Ct, Leonardtown, MD 20650
  • 44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    /97

    $640,000 Sold Jun 29, 2025

    • 3,635 Sq Ft
    • $176/SF
    • 10 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1999

    44114 Woodmont Dr, Leonardtown, MD 20650

    NO SHOWINGS UNTILL THE OPEN HOUSE MAY 24, SAT 11-2.Exceptional 5-Bedroom Home on 2 Acres. Welcome to this gorgeous 5-bedroom, 3.5-bath custom home, perfectly situated on a beautifully landscaped 2-acre lot. Impeccably maintained and thoughtfully designed, this property offers an ideal blend of luxury, comfort, and practicality. All five bedrooms are located on the upper level, including a

    Lori Jean Buongiovanni (Hethmon) RE/MAX Realty Group

    44114 Woodmont Dr, Leonardtown, MD 20650
    • 40539 Port Place, Leonardtown, MD 20650
      40539 Port Place, Leonardtown, MD 20650
      40539 Port Place, Leonardtown, MD 20650
      /92

      Est $1,109,860 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,371 Sq Ft

      40539 Port Place, Leonardtown, MD 20650

      40539 Port Place, Leonardtown, MD 20650

Showing Results 81 - 120, Page 3 of 18

Maryland St Marys County Leonardtown 20650

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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 © 2025 CoStar Group