6,982

Homes in ZIP Code 20650

Section Image
    • 40472 Port Place, Leonardtown, MD 20650
      40472 Port Place, Leonardtown, MD 20650
      40472 Port Place, Leonardtown, MD 20650
      /46

      Est $890,904 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,828 Sq Ft

      40472 Port Place, Leonardtown, MD 20650

      40472 Port Place, Leonardtown, MD 20650
  • 23745 Bayside Rd, Leonardtown, MD 20650
    23745 Bayside Rd, Leonardtown, MD 20650
    23745 Bayside Rd, Leonardtown, MD 20650
    /36

    $399,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    23745 Bayside Rd, Leonardtown, MD 20650

    *Offer Deadline for Friday, September 12th, no later than 6PM.* Privacy, peace and pristine are all words that describe 23745 Bayside Road. This three bedroom, two bath rambler has been fully updated with today's modern finishes and custom features like wood pantry shelving & other great features, giving you style in every room. Nestled on one acre of extremely private land with a long winding

    Delaney Burgess RE/MAX United Real Estate

    23745 Bayside Rd, Leonardtown, MD 20650
  • 42921 Hungerford Ct, Hollywood, MD 20636
    42921 Hungerford Ct, Hollywood, MD 20636
    42921 Hungerford Ct, Hollywood, MD 20636
    /47

    $745,000 Sold May 15, 2025

    • 3,929 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    42921 Hungerford Ct, Hollywood, MD 20636

    Stunning Colonial Home on 2.7 AcresThis beautifully maintained Colonial home sits on a private 2.7-acre lot at the end of a cul-de-sac, offering both seclusion and easy access to trails in the woods. The main level features an open kitchen and family room with a gas fireplace. Hardwood floors throughout including living and dining areas. Enjoy entertaining in the 20x20 heated screened porch,

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    42921 Hungerford Ct, Hollywood, MD 20636
    • 42454 Wilderness Rd, Leonardtown, MD 20650
      42454 Wilderness Rd, Leonardtown, MD 20650
      42454 Wilderness Rd, Leonardtown, MD 20650
      /22

      Est $418,235 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft

      42454 Wilderness Rd, Leonardtown, MD 20650

      42454 Wilderness Rd, Leonardtown, MD 20650
  • 23220 Brandon Ct, Leonardtown, MD 20650
    23220 Brandon Ct, Leonardtown, MD 20650
    23220 Brandon Ct, Leonardtown, MD 20650
    /61

    $545,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,102 Sq Ft

    23220 Brandon Ct, Leonardtown, MD 20650

    Welcome home to this beautifully maintained one-level brick front residence, offering a thoughtfully designed split-bedroom floorplan ideal for both comfort and privacy. With 3 bedrooms and 2 full baths, this home features a welcoming foyer entry that leads to a spacious formal dining area, perfect for gatherings and special occasions.The family room boasts vaulted ceilings and a cozy gas

    Jennifer Goddard CENTURY 21 New Millennium

    23220 Brandon Ct, Leonardtown, MD 20650
  • 23598 Belmar Dr, Leonardtown, MD 20650
    23598 Belmar Dr, Leonardtown, MD 20650
    23598 Belmar Dr, Leonardtown, MD 20650
    /10

    $660,000 Sold May 15, 2025

    • 3,758 Sq Ft
    • $176/SF
    • 16 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2010

    23598 Belmar Dr, Leonardtown, MD 20650

    Welcome to this beautifully upgraded 5-bedroom, 3.5-bathroom home, perfectly situated on one of the best lots in the neighborhood! Backing to trees for added privacy, this home offers both elegance and functionality.Step inside to find refinished hardwood floors throughout the main level, adding warmth and sophistication. The gourmet kitchen features sleek quartz countertops, a new backsplash,

    Heather Foster RE/MAX One

    23598 Belmar Dr, Leonardtown, MD 20650
    • 41936 Kentucky Ct, Leonardtown, MD 20650
      41936 Kentucky Ct, Leonardtown, MD 20650
      41936 Kentucky Ct, Leonardtown, MD 20650
      /83

      Est $556,451 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,115 Sq Ft

      41936 Kentucky Ct, Leonardtown, MD 20650

      41936 Kentucky Ct, Leonardtown, MD 20650
  • 21137 Marigold St, Leonardtown, MD 20650
    21137 Marigold St, Leonardtown, MD 20650
    21137 Marigold St, Leonardtown, MD 20650
    /42

    $544,999 Under Contract

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

    21137 Marigold St, Leonardtown, MD 20650

    Imagine this: a spacious, thoughtfully designed home where bright natural light fills oversized rooms while still offering the privacy you crave. Hardwood floors, crown molding, and 9-foot ceilings creating an inviting atmosphere, and a full walk-out basement plus a laundry room with built-in cabinetry add practical living space. The master suite features a soaking tub and separate shower, and

    Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
  • 20235 Big Oak Ln, Leonardtown, MD 20650
    20235 Big Oak Ln, Leonardtown, MD 20650
    20235 Big Oak Ln, Leonardtown, MD 20650
    /23

    $295,000 Sold May 14, 2025

    • 1,036 Sq Ft
    • $285/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1934

    20235 Big Oak Ln, Leonardtown, MD 20650

    Water access home with 3 bedrooms and 1 bath with laundry closet. Laminate flooring for easy of cleaning and pet friendly throughout much of the home. Level yard with big shed in back with 2 sides to store kayaks or other fun equipment for warm weather use. Patio in back and large clear side yard for volleyball or bocce ball or even corn hole. Make your plans now to come and see and make it your

    Jan Kleponis O'Brien Realty ERA Powered

    20235 Big Oak Ln, Leonardtown, MD 20650
    • 20370 Chingville Rd, Leonardtown, MD 20650
      20370 Chingville Rd, Leonardtown, MD 20650
      20370 Chingville Rd, Leonardtown, MD 20650
      /54

      Est $583,240 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,538 Sq Ft

      20370 Chingville Rd, Leonardtown, MD 20650

      20370 Chingville Rd, Leonardtown, MD 20650
  • 41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    /53

    $699,900 Under Contract

    • 5 Beds
    • 4 Baths
    • 3,825 Sq Ft

    41480 Whimsical Ct, Leonardtown, MD 20650

    Welcome home to this stunning and spacious colonial in sought after Leonards Grant. This home enjoys over 3,800 square feet and is situated on .46 acre at the end of the cul-de-sac making it a private oasis. Upon entering, you're greeted by a two story foyer that is filled with natural sunlight. You'll instantly notice the pristine hard wood floors that flow throughout the home, along with the

    Fran Slade Compass

    41480 Whimsical Ct, Leonardtown, MD 20650
  • 22158 Monterey Place, Leonardtown, MD 20650
    22158 Monterey Place, Leonardtown, MD 20650
    22158 Monterey Place, Leonardtown, MD 20650
    /56

    $500,000 Sold May 09, 2025

    • 1,782 Sq Ft
    • $281/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    22158 Monterey Place, Leonardtown, MD 20650

    Rarely do you have this kind of water view from every room in the home. Enjoy waking to vacation type views everyday....This home has a unique design that affords itself to many buyers. Pride of ownership abounds. Many recent improvements, including windows and doors. Roof replaced approx. 5 years ago. Home shows very well. Come see this home quickly so you can make this your new home.

    C. Brandon Harrington PAX Real Estate

    22158 Monterey Place, Leonardtown, MD 20650
    • 22425 Archer St, Leonardtown, MD 20650
      22425 Archer St, Leonardtown, MD 20650
      22425 Archer St, Leonardtown, MD 20650
      /61

      Est $730,738 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft

      22425 Archer St, Leonardtown, MD 20650

      22425 Archer St, Leonardtown, MD 20650
  • 0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    /6

    $5,000 Under Contract

    • Land
    • 0.14 Acre
    • $35,714 per Acre

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650

    Wonderful opportunity with a buyer that has vision. Nice lot to possibly build on. Call St Mary's county for details and confirm if suitable for your needs.

    Jan Kleponis O'Brien Realty ERA Powered

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
  • 21620 Coves End Ct, Leonardtown, MD 20650
    21620 Coves End Ct, Leonardtown, MD 20650
    21620 Coves End Ct, Leonardtown, MD 20650
    /67

    $691,000 Sold May 09, 2025

    • 3,541 Sq Ft
    • $195/SF
    • 33 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    21620 Coves End Ct, Leonardtown, MD 20650

    ASSUMABLE RATE MORTGAGE AVAILABLE AT 2.5%. Don't miss your chance to own property in the highly desirable Breton Bay Golf Community of Leonardtown. Here you'll enjoy stunning views of the beautiful golf course and the perks of living in a waterfront community with a nearby marina and access to a private beach area of the Bay! Situated on a small, quiet cul-de-sac street located directly across

    Hannah Cole Real Broker, LLC

    21620 Coves End Ct, Leonardtown, MD 20650
    • 22373 Armstrong Dr, Leonardtown, MD 20650
      22373 Armstrong Dr, Leonardtown, MD 20650
      22373 Armstrong Dr, Leonardtown, MD 20650
      /43

      Est $341,390 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 912 Sq Ft

      22373 Armstrong Dr, Leonardtown, MD 20650

      22373 Armstrong Dr, Leonardtown, MD 20650
  • 21158 Marigold St, Leonardtown, MD 20650
    21158 Marigold St, Leonardtown, MD 20650
    21158 Marigold St, Leonardtown, MD 20650
    /73

    $500,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,649 Sq Ft

    21158 Marigold St, Leonardtown, MD 20650

    Welcome to 21158 Marigold St, a beautifully maintained Colonial in the sought-after Kingston Estates community. This spacious home offers over 2,600 sq ft of living space on more than an acre, blending comfort, functionality, and privacy. It features 4 generously sized bedrooms, 2.5 bathrooms, a finished basement, and an updated kitchen with stainless steel appliances. Step outside to a peaceful,

    Jarred Green Real Broker, LLC

    21158 Marigold St, Leonardtown, MD 20650
  • 42500 Saint Margarets Dr, Leonardtown, MD 20650
    42500 Saint Margarets Dr, Leonardtown, MD 20650
    42500 Saint Margarets Dr, Leonardtown, MD 20650
    /12

    $135,000 Sold May 09, 2025

    • Land
    • 4.8 Acres
    • $28,125 per Acre
    • 76 Days On Market

    42500 Saint Margarets Dr, Leonardtown, MD 20650

    Expansive 4.8-Acre lot in highly sought after location.RECORDED PERC! Ready to build! Located just minutes outside the heart of Leonardtown, MD, this beautiful 4.8-acre lot offers a rare opportunity to bring your dream home to life on almost 5 private acres. Please be advised lot lines drawn on listing photo are not exact; just approximate and for visual purposes only.

    Kalee Kelly Infinitas Realty Group

    42500 Saint Margarets Dr, Leonardtown, MD 20650
    • 23571 Gunnell Dr, Leonardtown, MD 20650
      23571 Gunnell Dr, Leonardtown, MD 20650
      23571 Gunnell Dr, Leonardtown, MD 20650
      /35

      Est $551,845 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,652 Sq Ft

      23571 Gunnell Dr, Leonardtown, MD 20650

      23571 Gunnell Dr, Leonardtown, MD 20650
  • 40480 Parsons Mill Rd, Leonardtown, MD 20650
    40480 Parsons Mill Rd, Leonardtown, MD 20650
    40480 Parsons Mill Rd, Leonardtown, MD 20650
    /48

    $429,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,884 Sq Ft

    40480 Parsons Mill Rd, Leonardtown, MD 20650

    Experience country living at its finest in this expansive rambler, nestled amidst picturesque farmlands. This charming home offers three generously sized bedrooms and one well-appointed bathroom, epitomizing the timeless appeal of rural living. Rich hardwood floors flow seamlessly throughout the entire residence, adding warmth and character.Each bedroom is designed for comfort, offering

    John Gatton CENTURY 21 New Millennium

    40480 Parsons Mill Rd, Leonardtown, MD 20650
  • 41442 Dauber Way, Leonardtown, MD 20650
    41442 Dauber Way, Leonardtown, MD 20650
    41442 Dauber Way, Leonardtown, MD 20650
    /50

    $610,000 Sold May 08, 2025

    • 3,558 Sq Ft
    • $171/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2013

    41442 Dauber Way, Leonardtown, MD 20650

    Don’t miss this fantastic find in Leonard's Grant! This bright and airy home features an open floor plan, soaring ceilings, and abundant natural light. The spacious family room flows seamlessly into the kitchen and main living areas, creating an inviting space for everyday living.Upstairs, you’ll find three well-sized bedrooms and convenient bedroom-level laundry. The primary suite offers high

    Lesa Clark Redfin Corp

    41442 Dauber Way, Leonardtown, MD 20650
    • 40457 Breton View Dr, Leonardtown, MD 20650
      40457 Breton View Dr, Leonardtown, MD 20650
      40457 Breton View Dr, Leonardtown, MD 20650
      /58

      Est $418,093 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,286 Sq Ft

      40457 Breton View Dr, Leonardtown, MD 20650

      40457 Breton View Dr, Leonardtown, MD 20650
  • 22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    /46

    $350,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    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
  • 21500 Point Lookout Rd, Callaway, MD 20620
    21500 Point Lookout Rd, Callaway, MD 20620
    21500 Point Lookout Rd, Callaway, MD 20620
    /97

    $600,000 Sold May 06, 2025

    • 3,605 Sq Ft
    • $166/SF
    • 253 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1955

    21500 Point Lookout Rd, Callaway, MD 20620

    All-Brick Rambler on a 6.11 acre lot along with a 9.58 acre separate lot with potential for additional homesite. This price includes both lots Welcome to 21500 Point Lookout Road, Leonardtown! This all-brick rambler sits on a large extensively landscaped lot and offers over 3,600 sq. ft. on the main level, plus 1,200 sq. ft. in the partially finished lower level. The home features 3 bedrooms

    Jennifer Goddard CENTURY 21 New Millennium

    21500 Point Lookout Rd, Callaway, MD 20620
    • 23577 Abraham Dr, Leonardtown, MD 20650
      23577 Abraham Dr, Leonardtown, MD 20650
      23577 Abraham Dr, Leonardtown, MD 20650
      /47

      Est $611,847 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,929 Sq Ft

      23577 Abraham Dr, Leonardtown, MD 20650

      23577 Abraham Dr, Leonardtown, MD 20650
  • 41474 Charismatic Way, Leonardtown, MD 20650
    41474 Charismatic Way, Leonardtown, MD 20650
    41474 Charismatic Way, Leonardtown, MD 20650
    /79

    $639,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,647 Sq Ft

    41474 Charismatic Way, Leonardtown, MD 20650

    Welcome to 41474 Charismatic Way in the highly sought-after Leonard’s Grant community of Leonardtown, Maryland. This beautifully maintained 5-bedroom, 3.5-bath home offers over 3,600 square feet of finished living space and combines elegance, comfort, and function in every detail. From the charming large front porch to the professionally landscaped yard, the curb appeal is undeniable. Step inside

    Laura Bernth RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
  • 40222 Breton Beach Rd, Leonardtown, MD 20650
    40222 Breton Beach Rd, Leonardtown, MD 20650
    40222 Breton Beach Rd, Leonardtown, MD 20650
    /37

    $540,000 Sold Apr 30, 2025

    • 1,296 Sq Ft
    • $417/SF
    • 207 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1976

    40222 Breton Beach Rd, Leonardtown, MD 20650

    This dreamy waterfront getaway is the perfect spot for you to fully unwind and relax. Located directly along Breton Bay, you'll enjoy peace and serenity while only being a short 10 minute drive from downtown Leonardtown, or take a short boat ride across the bay to Fitzies for drinks and dinner. This charming cape cod offers amazing sunsets whether it's from the scenic deck, screened in porch or

    Jake Grier Baldus Real Estate, Inc.

    40222 Breton Beach Rd, Leonardtown, MD 20650
    • 22909 Cedar Lane Rd, Leonardtown, MD 20650
      22909 Cedar Lane Rd, Leonardtown, MD 20650
      22909 Cedar Lane Rd, Leonardtown, MD 20650
      /77

      Est $491,242 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,275 Sq Ft

      22909 Cedar Lane Rd, Leonardtown, MD 20650

      22909 Cedar Lane Rd, 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 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,914 Sq Ft

    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
  • 23267 Clarks Rest Rd, Leonardtown, MD 20650
    23267 Clarks Rest Rd, Leonardtown, MD 20650
    23267 Clarks Rest Rd, Leonardtown, MD 20650
    /66

    $700,000 Sold Apr 25, 2025

    • 5,213 Sq Ft
    • $134/SF
    • 3 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 2015

    23267 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this impressive and elegant 5-bedroom, 4 full and 2 half-bath home, offering the perfect blend of luxury, comfort, and energy efficiency. Located in a highly desirable community with walking sidewalks, a community center, playgrounds, and a sparkling pool, this property provides an exceptional lifestyle. Plus, it's only a convenient trolley ride away from downtown Leonardtown, where

    Chris Hill CENTURY 21 New Millennium

    23267 Clarks Rest Rd, Leonardtown, MD 20650
    • 40427 Breton View Dr, Leonardtown, MD 20650
      40427 Breton View Dr, Leonardtown, MD 20650
      40427 Breton View Dr, Leonardtown, MD 20650
      /86

      Est $420,372 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 2,676 Sq Ft

      40427 Breton View Dr, Leonardtown, MD 20650

      40427 Breton View Dr, Leonardtown, MD 20650
  • 43658 Redmond Rd, Leonardtown, MD 20650
    43658 Redmond Rd, Leonardtown, MD 20650
    43658 Redmond Rd, Leonardtown, MD 20650
    /16

    $275,000 Under Contract

    • 4 Beds
    • 1.5 Baths
    • 2,078 Sq Ft

    43658 Redmond Rd, Leonardtown, MD 20650

    DON'T MISS THIS FABULOUS OPPORTUNITY***FANTASTIC BRICK RAMBLER***4 BEDROOMS***2 CAR GARAGE***FORMAL DINING ROOM***HARDWOOD FLOORS***BRICK FIREPLACE***CHAINLINK FENCE***CEILING FANS***2 CAR CARPORT***ENJOY THE PEAR TREE***CENTRAL AIR***THIS HOME IS BEING SOLD COMPLETELY AS-IS***HURRY THIS PROPERTY WON'T LAST LONG**

    Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
  • 23749 Coventry Dr, Leonardtown, MD 20650
    23749 Coventry Dr, Leonardtown, MD 20650
    23749 Coventry Dr, Leonardtown, MD 20650
    /64

    $739,900 Sold Apr 25, 2025

    • 6,015 Sq Ft
    • $123/SF
    • 179 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2013

    23749 Coventry Dr, Leonardtown, MD 20650

    This exceptional home is designed with luxury and space in mind, featuring expansive rooms thanks to bump-outs on two sides. The main level is an entertainer's dream, boasting an open floor plan that seamlessly connects the gourmet kitchen, breakfast room, family room, dining area, and sunroom. A library or office adds a touch of versatility. Hardwood floors run throughout the first two levels,

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23749 Coventry Dr, Leonardtown, MD 20650
    • 42705 Redgate Farm Ln, Leonardtown, MD 20650
      42705 Redgate Farm Ln, Leonardtown, MD 20650
      42705 Redgate Farm Ln, Leonardtown, MD 20650
      /64

      Est $492,086 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,243 Sq Ft

      42705 Redgate Farm Ln, Leonardtown, MD 20650

      42705 Redgate Farm Ln, Leonardtown, MD 20650
  • 23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    /25

    $415,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft

    23730 Hicks Dr, Leonardtown, MD 20650

    Back on market at a new price — the buyer’s loss is your gain! This is one of only five single-family homes in Leonardtown currently listed under $500,000 — and it’s move-in ready with major updates already done. Renovated just 3 years ago, this charming 3-bedroom, 2-bath rambler sits on a spacious half-acre lot with a walk-out basement and no HOA, giving you flexibility to bring your vision to

    Kimberlee Randall Group EXP Realty, LLC

    23730 Hicks Dr, Leonardtown, MD 20650
  • 41443 Whimsical Ct, Leonardtown, MD 20650
    41443 Whimsical Ct, Leonardtown, MD 20650
    41443 Whimsical Ct, Leonardtown, MD 20650
    /4

    $645,000 Sold Apr 22, 2025

    • 3,400 Sq Ft
    • $190/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2010

    41443 Whimsical Ct, Leonardtown, MD 20650

    Welcome to this beautifully updated 5-bedroom, 3.5-bath Colonial home, offering the perfect blend of modern updates and classic charm. Step inside to find refinished hardwood floors, fresh paint, and new carpet throughout, creating a bright and inviting atmosphere.The heart of the home extends outdoors, where you'll discover a serene, tree-lined backyard with an incredible outdoor living space.

    Heather Foster RE/MAX One

    41443 Whimsical Ct, Leonardtown, MD 20650
    • 20995 Chestnut Ridge Dr, Leonardtown, MD 20650
      20995 Chestnut Ridge Dr, Leonardtown, MD 20650
      20995 Chestnut Ridge Dr, Leonardtown, MD 20650
      /9

      Est $527,329 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,149 Sq Ft

      20995 Chestnut Ridge Dr, Leonardtown, MD 20650

      20995 Chestnut Ridge Dr, Leonardtown, MD 20650
  • 23534 Belmar Dr, Leonardtown, MD 20650
    23534 Belmar Dr, Leonardtown, MD 20650
    23534 Belmar Dr, Leonardtown, MD 20650
    /79

    $649,000 Under Contract

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

    23534 Belmar Dr, Leonardtown, MD 20650

    PRICE REDUCED + EXCEPTIONAL FINANCING OPTIONS! Now listed more than $16,000 below the original asking price, 23534 Belmar Drive is your opportunity to own a beautifully maintained, move-in-ready home in the highly sought-after Leonard’s Grant community of Leonardtown. Boasting over 5,000 sq ft of finished living space, this impressive home offers 5 spacious bedrooms, 3.5 baths, and an ideal

    Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
  • 22925 Downs Cir, Leonardtown, MD 20650
    22925 Downs Cir, Leonardtown, MD 20650
    22925 Downs Cir, Leonardtown, MD 20650
    /38

    $387,000 Sold Apr 21, 2025

    • 1,904 Sq Ft
    • $203/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1977

    22925 Downs Cir, Leonardtown, MD 20650

    Convenient, central location walkable to downtown Leonardtown! Tucked away on a quiet cul-de-sac, this house was beautifully renovated. ! Enjoy evenings on the generously oversized deck with pergola. Huge yard backs to trees. Great use of space throughout - master features walk-in closet and full master bath, finished basement offers lots of extra room!

    Ross Simone RE/MAX Realty Group

    22925 Downs Cir, Leonardtown, MD 20650
    • 22292 White Oak Rd, Leonardtown, MD 20650
      22292 White Oak Rd, Leonardtown, MD 20650
      22292 White Oak Rd, Leonardtown, MD 20650
      /43

      Est $441,595 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft

      22292 White Oak Rd, Leonardtown, MD 20650

      22292 White Oak Rd, Leonardtown, MD 20650

Showing Results 201 - 240, Page 6 of 18

Maryland St Marys County Leonardtown 20650

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