6,684

Leonardtown, MD Homes

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  • 23242 Clarks Rest Rd, Leonardtown, MD 20650
    23242 Clarks Rest Rd, Leonardtown, MD 20650
    /2

    $599,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 2,296 Sq Ft

    23242 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Clark’s Rest community of Leonardtown! Boasting an open floor plan filled with natural light, this home offers a perfect blend of comfort and functionality.The main level features spacious living and dining areas that flow effortlessly into a modern kitchen—ideal for entertaining and everyday

    Matthew Burgan Infinitas Realty Group

    23242 Clarks Rest Rd, 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
    • 41895 Tomey Ct, Leonardtown, MD 20650
      41895 Tomey Ct, Leonardtown, MD 20650
      41895 Tomey Ct, Leonardtown, MD 20650
      /83

      Est $538,445 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
  • 21143 Catnip Ct, Leonardtown, MD 20650
    21143 Catnip Ct, Leonardtown, MD 20650
    21143 Catnip Ct, Leonardtown, MD 20650
    /69

    $635,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,642 Sq Ft

    21143 Catnip Ct, Leonardtown, MD 20650

    Welcome to this stunning 4-bedroom, 2.5-bath home in the desirable Kingston Estatesneighborhood of Leonardtown. Lovingly maintained by the original owners, this homesits on a beautifully landscaped lot of nearly an acre, and is nestled in a quiet cul-de-sacthat offers both privacy and convenience.As you step inside, you’ll be greeted by the stunning Acacia wood floors that flowthroughout the main

    Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, 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 Exit Landmark Realty

    21620 Coves End Ct, Leonardtown, MD 20650
    • 21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      /56

      Est $673,005 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
  • 44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    /97

    $615,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,635 Sq Ft

    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
  • 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
    • 4.80 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
    • 41503 Affirmed Way, Leonardtown, MD 20650
      41503 Affirmed Way, Leonardtown, MD 20650
      41503 Affirmed Way, Leonardtown, MD 20650
      /80

      Est $694,430 Not Listed For Sale

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

      41503 Affirmed Way, Leonardtown, MD 20650

      41503 Affirmed Way, Leonardtown, MD 20650
  • 42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    /71

    $599,900 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,233 Sq Ft

    42261 Bird Haven Dr, Leonardtown, MD 20650

    Welcome to this charming 4-bedroom, 3.5-bathroom home nestled in the sought-after Kingston Estates of Leonardtown. Lovingly maintained by its original owners, this house seamlessly blends comfort, convenience and tranquility.Upon entering, you're greeted by bright and airy living spaces adorned with gorgeous wood floors that flow throughout much of the main level. The heart of the home is the

    Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, 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
    • 22555 Breton Bay Dr, Leonardtown, MD 20650
      22555 Breton Bay Dr, Leonardtown, MD 20650
      22555 Breton Bay Dr, Leonardtown, MD 20650
      /48

      Est $662,265 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
  • 23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    /75

    $585,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 3,188 Sq Ft

    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
  • 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
    • 40772 Magee Dr, Leonardtown, MD 20650
      40772 Magee Dr, Leonardtown, MD 20650
      40772 Magee Dr, Leonardtown, MD 20650
      /38

      Est $481,772 Not Listed For Sale

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

      40772 Magee Dr, Leonardtown, MD 20650

      40772 Magee Dr, Leonardtown, MD 20650
  • 21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    /70

    $624,900 Under Contract

    • 5 Beds
    • 2.5 Baths
    • 3,664 Sq Ft

    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 living! Main

    Matthew Burgan Infinitas Realty Group

    21897 Fairway Dr, 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
    • 21715 Pebble Beach Ct, Leonardtown, MD 20650
      21715 Pebble Beach Ct, Leonardtown, MD 20650
      21715 Pebble Beach Ct, Leonardtown, MD 20650
      /78

      Est $741,270 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
  • 41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    /54

    $525,000

    • 5 Beds
    • 3 Baths
    • 2,420 Sq Ft

    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, and a

    Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, 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
    • 40139 Combs Creek Way, Leonardtown, MD 20650
      40139 Combs Creek Way, Leonardtown, MD 20650
      40139 Combs Creek Way, Leonardtown, MD 20650
      /68

      Est $1,186,159 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
  • 41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    /15

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    41130 Cryer Ct, Leonardtown, MD 20650

    A rare opportunity on the shores of Breton Bay, presents a canvas for transformation. This expansive 1.05 acre waterfront boast 164 feet of private shoreline and delivers breathtaking sunset panoramas. This classic 1955 construction offers endless renovation potential. With 1468 square feet of main living space and a 1247 square foot basement, this 3 bedroom 2 bathroom home shows potential

    Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, 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
    • 23581 Belmar Dr, Leonardtown, MD 20650
      23581 Belmar Dr, Leonardtown, MD 20650
      23581 Belmar Dr, Leonardtown, MD 20650
      /54

      Est $410,865 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,238 Sq Ft

      23581 Belmar Dr, Leonardtown, MD 20650

      23581 Belmar Dr, Leonardtown, MD 20650
  • 41554 Briarwood Cir, Leonardtown, MD 20650
    41554 Briarwood Cir, Leonardtown, MD 20650
    41554 Briarwood Cir, Leonardtown, MD 20650
    /70

    $449,000

    • 3 Beds
    • 3.5 Baths
    • 2,379 Sq Ft

    41554 Briarwood Cir, Leonardtown, MD 20650

    Location is key.... Not just in Leonardtown, but in the community itself. Through every window of the rear of this house is the picturesque setting of the wooded tree line and abundant privacy, not often found in Townhome living. This home is tucked back from main road on an open green in front and woods in the rear. Upgrades to this home from original build include: Premium COREtec Pro Plus

    Wayne & Christine Floyd RE/MAX Realty Group

    41554 Briarwood Cir, 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
    • 42990 Baywood Place, Leonardtown, MD 20650
      42990 Baywood Place, Leonardtown, MD 20650
      42990 Baywood Place, Leonardtown, MD 20650
      /68

      Est $659,827 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
  • 23674 Jm Gough Ct, Leonardtown, MD 20650
    23674 Jm Gough Ct, Leonardtown, MD 20650
    23674 Jm Gough Ct, Leonardtown, MD 20650
    /72

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,697 Sq Ft

    23674 Jm Gough Ct, Leonardtown, MD 20650

    Welcome home to this beautifully updated Colonial located in a charming and quiet Leonardtown neighborhood—just minutes from local restaurants, shopping, and all the conveniences of town living.Freshly painted throughout and featuring brand-new carpet, this 4-bedroom, 2.5-bath gem is move-in ready and full of modern upgrades. The heart of the home is a gourmet kitchen with upgraded stainless

    Heather Foster RE/MAX One

    23674 Jm Gough Ct, Leonardtown, MD 20650
  • 20503 Deer Wood Park Dr, Leonardtown, MD 20650
    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    /117

    $725,000 Sold Apr 17, 2025

    • 5,862 Sq Ft
    • $124/SF
    • 19 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1997

    20503 Deer Wood Park Dr, Leonardtown, MD 20650

    Discover this expansive, custom-designed brick Colonial situated on 2 pristine acres in the highly sought-after Chestnut Hills subdivision. Meticulously maintained, this stunning home offers a grand 2-story foyer and a soaring family room with a cozy propane fireplace, all complemented by 9-foot ceilings throughout the main level.The open-concept kitchen is a chef’s dream, featuring a center

    Tracey Summers CENTURY 21 New Millennium

    20503 Deer Wood Park Dr, 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 $638,987 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
  • 41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    /50

    $540,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    Welcome to your dream home in highly sought-after Clarks Rest, just minutes from all the charm and dining of Leonardtown Square. This vibrant community features sidewalks, a community pool, and that perfect neighborhood feel you’ve been looking for. Step inside to find real hardwood floors in the entryway and luxury vinyl plank flooring throughout the main living areas, including the spacious

    Delaney Burgess RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
  • 19710 Tower Hill Rd, Leonardtown, MD 20650
    19710 Tower Hill Rd, Leonardtown, MD 20650
    19710 Tower Hill Rd, Leonardtown, MD 20650
    /3

    $1,225,000 Sold Mar 31, 2025

    • 5,690 Sq Ft
    • $215/SF
    • 5 Beds
    • 6.5 Baths
    • Built 1984

    19710 Tower Hill Rd, Leonardtown, MD 20650

    Private 3.31 acre lot with beautiful views across the Potomac River. Home is almost 6000 square feet with close to 200 feet of rip rapped water frontage. 6 bedrooms and 5.5 baths including a private in law suite. Main level formal living room with doors leading to sunroom, formal dining room, private office with custom built ins, large family room off kitchen with wood burning fireplace and

    Jennifer Goddard CENTURY 21 New Millennium

    19710 Tower Hill Rd, Leonardtown, MD 20650
    • 22223 Monterey Place, Leonardtown, MD 20650
      22223 Monterey Place, Leonardtown, MD 20650
      22223 Monterey Place, Leonardtown, MD 20650
      /63

      Est $645,766 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
  • 39645 Sweetpea Ln, Leonardtown, MD 20650
    39645 Sweetpea Ln, Leonardtown, MD 20650
    39645 Sweetpea Ln, Leonardtown, MD 20650
    /67

    $799,900

    • Land
    • 3.56 Acres
    • $224,691 per Acre

    39645 Sweetpea Ln, Leonardtown, MD 20650

    UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless

    Sandi Denny CENTURY 21 New Millennium

    39645 Sweetpea Ln, Leonardtown, MD 20650
  • 43012 Bluejay Ln, Leonardtown, MD 20650
    43012 Bluejay Ln, Leonardtown, MD 20650
    43012 Bluejay Ln, Leonardtown, MD 20650
    /9

    $740,500 Sold Mar 27, 2025

    • 3,440 Sq Ft
    • $215/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2021

    43012 Bluejay Ln, Leonardtown, MD 20650

    Come visit this lovely Fairfax model home in the desirable community of The Meadows at Town Run. Built in 2021 by Quality Built Homes, this beauty will not disappoint. Nestled on a corner lot at the end of a quiet cul-de-sac and backing to trees add to the charm and privacy of this immaculately kept beauty. Inside the home you will find well thought-out appointments, to include 5 bedrooms and

    Robin Errington CENTURY 21 New Millennium

    43012 Bluejay Ln, Leonardtown, MD 20650
    • 40539 Port Place, Leonardtown, MD 20650
      40539 Port Place, Leonardtown, MD 20650
      40539 Port Place, Leonardtown, MD 20650
      /92

      Est $1,137,768 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
  • 41505 Knight Rd, Leonardtown, MD 20650
    41505 Knight Rd, Leonardtown, MD 20650
    41505 Knight Rd, Leonardtown, MD 20650
    /126

    $5,950,000

    • 5 Beds
    • 8 Baths
    • 12,113 Sq Ft

    41505 Knight Rd, Leonardtown, MD 20650

    Stunning. Welcome to a world of unparalleled luxury and breathtaking beauty. Nestled along the tranquil waters off of the Potomac River, this custom-built four level waterfront estate on almost 18 acres, is a testament to architectural brilliance and sophisticated design. As you approach the grand entrance, you are greeted by a circular driveway, detached 3-car garage, attached 2-car garage, lush

    Travis Gray Engel & Völkers Annapolis

    41505 Knight Rd, Leonardtown, MD 20650
  • 42297 Riverwinds Dr, Leonardtown, MD 20650
    42297 Riverwinds Dr, Leonardtown, MD 20650
    42297 Riverwinds Dr, Leonardtown, MD 20650
    /56

    $1,450,000 Sold Mar 26, 2025

    • 3,709 Sq Ft
    • $391/SF
    • 4 Days On Market
    • 4 Beds
    • 7 Baths
    • Built 1983

    42297 Riverwinds Dr, Leonardtown, MD 20650

    Custom waterfront home on the Potomac River with breathtaking panoramic views. Designed for both family living and entertaining, this spacious residence boasts a thoughtfully remodeled gourmet kitchen by St. Maries Builders, a family room, sunroom, living room, and a large den with a full bath on the main level. Expansive windows maximize natural light and showcase stunning sunsets.The

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    42297 Riverwinds Dr, Leonardtown, MD 20650
    • 21084 Rosebay St, Leonardtown, MD 20650
      21084 Rosebay St, Leonardtown, MD 20650
      21084 Rosebay St, Leonardtown, MD 20650
      /31

      Est $569,651 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,505 Sq Ft

      21084 Rosebay St, Leonardtown, MD 20650

      21084 Rosebay St, Leonardtown, MD 20650
  • 23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    /27

    $419,500

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

    23730 Hicks Dr, Leonardtown, MD 20650

    *Pending Release..Buyer got cold feet* Come check out this charming, move-in ready rambler with room to grow that has been waiting for YOU! This beautifully updated 3-bedroom, 2-bath home sits on a spacious half-acre lot and features a walk-out basement, newer roof, windows, siding, gutters, and furnace. Inside, you’ll find brand new LVP flooring, recessed lighting in the kitchen, living room,

    Kimberlee Randall Group EXP Realty, LLC

    23730 Hicks Dr, Leonardtown, MD 20650

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