6,680

Leonardtown, MD Homes

Section Image Section Image
  • 41997 Loker Ct, Leonardtown, MD 20650
    41997 Loker Ct, Leonardtown, MD 20650
    41997 Loker Ct, Leonardtown, MD 20650
    /41

    $479,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,330 Sq Ft

    41997 Loker Ct, Leonardtown, MD 20650

    Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 896-3385

    41997 Loker Ct, Leonardtown, MD 20650
  • 41468 Marwood Cir, Leonardtown, MD 20650
    41468 Marwood Cir, Leonardtown, MD 20650
    41468 Marwood Cir, Leonardtown, MD 20650
    /11

    $2,900 per month

    • 3 Beds
    • 3.5 Baths
    • 2,522 Sq Ft
    • Townhouse for Rent

    41468 Marwood Cir, Leonardtown, MD 20650

    Townhome at the Clark's Rest neighborhood in Leonardtown. This layout is the Compton" Rear Kitchen Model"; featuring a 2-Car Rear Load Garage w. 3 bedrooms/ 3.5 baths with a finished basement ft. rec room and full bath. Upgraded options for this home include vinyl planks at Foyer, Powder Room and Dining Room, Stainless Steel Appliances, Granite Counters, upgraded cabinets, ceramic floors and

    Agent Photo

    Ali Haghgoo

    EXP Realty, LLC

    (240) 759-2241

    41468 Marwood Cir, Leonardtown, MD 20650
  • 21821 Cove Ln, Leonardtown, MD 20650
    21821 Cove Ln, Leonardtown, MD 20650
    21821 Cove Ln, Leonardtown, MD 20650
    /17

    $685,000 Sold Jun 20, 2025

    • 2,748 Sq Ft
    • $249/SF
    • 2 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1967

    21821 Cove Ln, Leonardtown, MD 20650

    Choice location, private point on Cherry Cove with outstanding views of Cherry Cove & Breton Bay. Solid brick rambler with lots of options; generous office could easily be converted into 3rd bedroom....sun room, family room and formal living room with fireplace. Home needs updating. A stunning, private, convenient location!

    Barbara Stellway KW Metro Center

    21821 Cove Ln, Leonardtown, MD 20650
    • 41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
      /47

      Est $530,407 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,156 Sq Ft

      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650

      41080 Paw Paw Hollow Ln, Leonardtown, MD 20650
  • 42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    /42

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft

    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

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 624-9572

    42239 Riverwinds Dr, Leonardtown, MD 20650
  • 44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    /32

    $2,150 - $2,750 per month

    The Hamptons at Leonardtown

    2-3 Beds

    44980 Hamptons Blvd, Leonardtown, MD 20650

    The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • 42279 Bird Haven Dr, Leonardtown, MD 20650
    42279 Bird Haven Dr, Leonardtown, MD 20650
    42279 Bird Haven Dr, Leonardtown, MD 20650
    /65

    $600,000 Sold Jun 17, 2025

    • 3,139 Sq Ft
    • $191/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2002

    42279 Bird Haven Dr, Leonardtown, MD 20650

    Beautiful home located in the desirable Leonardtown neighborhood of Kingston, this home features 5 bedrooms and 3.5 Baths . The main level features a large kitchen with granite counter tops and stainless steel appliances, spacious family room with wood burning fireplace, a home office with built-in storage, and formal dining room. The primary suite located on the second level features a large

    Mike Jordan CENTURY 21 New Millennium

    42279 Bird Haven Dr, Leonardtown, MD 20650
    • 22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      22605 Calvert St, Leonardtown, MD 20650
      /36

      Est $440,056 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft

      22605 Calvert St, Leonardtown, MD 20650

      22605 Calvert St, Leonardtown, MD 20650
  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • 39870 Lady Baltimore Ave, Leonardtown, MD 20650
    39870 Lady Baltimore Ave, Leonardtown, MD 20650
    39870 Lady Baltimore Ave, Leonardtown, MD 20650
    /15

    $2,500 per month

    • 4 Beds
    • 2.5 Baths
    • 1,380 Sq Ft
    • House for Rent

    39870 Lady Baltimore Ave, Leonardtown, MD 20650

    Charming Rambler in Water-Access Community – Available Now!Enjoy easy one-level living in this adorable 4-bedroom, 2.5-bath rambler nestled in the St. Clements Shores community. With access to St. Clements Bay, you'll love spending time outdoors in the spacious yard with mature trees, a large deck, and peaceful surroundings.Inside, the open-concept layout offers great flow for everyday living and

    Lesa Clark Redfin Corp

    39870 Lady Baltimore Ave, Leonardtown, MD 20650
  • 20640 Laurel Ct, Leonardtown, MD 20650
    20640 Laurel Ct, Leonardtown, MD 20650
    20640 Laurel Ct, Leonardtown, MD 20650
    /54

    $635,000 Sold Jun 16, 2025

    • 2,692 Sq Ft
    • $236/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    20640 Laurel Ct, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY MONDAY MAY 19th at NOON! Welcome to your own private retreat with a sparkling in-ground pool! This beautifully maintained 4-bedroom, 3.5-bath rambler is nestled on just under 3 serene acres in popular Chestnut Hills. With a sprawling main level and a massive 2,700+ sq ft unfinished walk-out basement, this home has the potential to offer over 5,500 total square feet of

    Sarah Mulford-Martin EXP Realty, LLC

    20640 Laurel Ct, Leonardtown, MD 20650
    • 41493 Margrove Cir, Leonardtown, MD 20650
      41493 Margrove Cir, Leonardtown, MD 20650
      41493 Margrove Cir, Leonardtown, MD 20650
      /32

      Est $433,301 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft

      41493 Margrove Cir, Leonardtown, MD 20650

      41493 Margrove Cir, Leonardtown, MD 20650
  • 24554 Pin Cushion Rd, Leonardtown, MD 20650
    24554 Pin Cushion Rd, Leonardtown, MD 20650
    /2

    $355,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    24554 Pin Cushion Rd, Leonardtown, MD 20650

    OPEN HOUSE Cancelled due to multiple offers in hand. All offers considered until noon on June 19th. a Welcome to your next adventure! This almost all brick rambler sits on 1.26 acres with NO HOA — giving you the freedom to live how you want. Inside, you’ll find 3 bedrooms, 2 full baths, and a private primary suite ready to be your personal retreat. Outside, enjoy a detached carport, a storage

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 571-2982

    24554 Pin Cushion Rd, Leonardtown, MD 20650
  • 22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    /12

    $1,750 - $1,950 per month

    Seymour Apartments

    1-2 Beds

    22645 Washington St, Leonardtown, MD 20650

    Introducing Seymour Apartments, in the heart of Historic Downtown Leonardtown! Come live in town just up the hill from the Warf while being steps away from the shops and restaurants on the square. Apartments in the Seymour Apartment building. Access to unit is from a common stairwell with private entrance. Units have new ductless heat pumps, onsite laundry is in common basement area,

    22645 Washington St, Leonardtown, MD 20650
  • 23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    /61

    $440,000 Sold Jun 16, 2025

    • 2,379 Sq Ft
    • $185/SF
    • 46 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    23445 Grovewood Ct, Leonardtown, MD 20650

    Welcome to 23445 Grovewood Court, an exquisitely maintained residence in the esteemed Clark's Rest community, where sophistication and serenity converge. This splendid 3-bedroom, 3.5-bath townhome offers an elevated living experience, combining impeccable design with unparalleled comfort. Step inside to discover an expansive and luminous open-concept floor plan, enhanced by refined finishes and

    John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
    • 23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      23748 Coventry Dr, Leonardtown, MD 20650
      /72

      Est $663,393 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,980 Sq Ft

      23748 Coventry Dr, Leonardtown, MD 20650

      23748 Coventry Dr, Leonardtown, MD 20650
  • 40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    /31

    $485,000 Open House 7/06

    • 4 Beds
    • 2.5 Baths
    • 1,770 Sq Ft

    40534 Miss Ettas Way, Leonardtown, MD 20650

    OPEN HOUSE, Sunday, July 6th 1 -3 PM. Welcome home to this beautifully maintained Cape Cod built by Hallmark Homes in 2016, situated on a peaceful 1.98-acre lot! Relax on the inviting front porch and take in the tranquil surroundings. Inside, you'll find a spacious living and dining room combo, perfect for entertaining. The kitchen features granite countertops, stainless steel appliances, and a

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 697-2564

    40534 Miss Ettas Way, Leonardtown, MD 20650
  • 43575 Blake Creek Rd, Leonardtown, MD 20650
    43575 Blake Creek Rd, Leonardtown, MD 20650
    43575 Blake Creek Rd, Leonardtown, MD 20650
    /32

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    43575 Blake Creek Rd, Leonardtown, MD 20650

    WATERFRONT RENTAL! Available for occupancy 7-16-25. Prepare to fall in love with the river view. This great brick one-level rental offers an open floor plan for the living, dining and kitchen areas and direct access to a waterfront screened porch overlooking the Potomac River. WIFI, Pier access and one garage bay included. This is an accessory unit that is attached to a larger brick home by a

    Michelle Camaioni RE/MAX Closers

    43575 Blake Creek Rd, Leonardtown, MD 20650
  • 44662 Blake Creek Rd, Leonardtown, MD 20650
    44662 Blake Creek Rd, Leonardtown, MD 20650
    44662 Blake Creek Rd, Leonardtown, MD 20650
    /6

    $320,500 Sold Jun 13, 2025

    • 1,344 Sq Ft
    • $238/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1963

    44662 Blake Creek Rd, Leonardtown, MD 20650

    This cozy cottage is located in a beautiful, peaceful setting with over an acre of mature fruit trees and flowers. This solid home, with its good bones, awaits a refreshing touch, making it an ideal project for investors or enthusiastic DIY buyers looking to create their dream space. Offered as is, this cottage holds great potential to become a truly special retreat.

    Ruth Mudd RE/MAX One

    44662 Blake Creek Rd, Leonardtown, MD 20650
    • 23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      23287 Crestmar Ln, Leonardtown, MD 20650
      /71

      Est $708,360 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,262 Sq Ft

      23287 Crestmar Ln, Leonardtown, MD 20650

      23287 Crestmar Ln, Leonardtown, MD 20650
  • 23745 Hicks Dr, Leonardtown, MD 20650
    23745 Hicks Dr, Leonardtown, MD 20650
    23745 Hicks Dr, Leonardtown, MD 20650
    /50

    $398,000 Open Sat 1PM - 2PM

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft

    23745 Hicks Dr, Leonardtown, MD 20650

    Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location—all with no HOA.Inside, you’ll find a bright and open layout featuring wide plank flooring, recessed lighting,

    Neil Smith Blackwell Real Estate, LLC

    23745 Hicks Dr, Leonardtown, MD 20650
  • 41665 Tudor Hall Rd, Leonardtown, MD 20650
    41665 Tudor Hall Rd, Leonardtown, MD 20650
    41665 Tudor Hall Rd, Leonardtown, MD 20650
    /11

    $2,100 per month

    • 4 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • House for Rent

    41665 Tudor Hall Rd, Leonardtown, MD 20650

    Please fill out application And make sure to include all tenants who are 18 and older also For an application fee.

    41665 Tudor Hall Rd, Leonardtown, MD 20650
  • 40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    /76

    $460,000 Sold Jun 12, 2025

    • 2,524 Sq Ft
    • $182/SF
    • 61 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    Have you been searching for a home with the PERFECT Water Views!! Without; the Water view price??This home may be what your heart Desires!! Walk your kayaks right down the SAME block to the community beach access spot. The "walking beach" as they call it. This home has water views from BOTH levels. There are wood burning stoves on BOTH levels. The main beach access with playground and pavilion

    Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $509,503 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft

      22301 Bayside Rd, Leonardtown, MD 20650

      22301 Bayside Rd, Leonardtown, MD 20650
  • 23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    /88

    $685,000 Under Contract

    • 6 Beds
    • 3.5 Baths
    • 4,267 Sq Ft

    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
  • 22695 Washington St Unit 2, Leonardtown, MD 20650
    22695 Washington St Unit 2, Leonardtown, MD 20650
    22695 Washington St Unit 2, Leonardtown, MD 20650
    /6

    $1,400 per month

    • 1 Bed
    • 1 Bath
    • 11,686 Sq Ft
    • Condo for Rent

    22695 Washington St Unit 2, Leonardtown, MD 20650

    Welcome to your charming new home in the heart of historic Leonardtown! This delightful 1-bedroom, 1-bathroom apartment boasts fresh paint and brand-new luxury vinyl plank (LVP) flooring, providing a modern and comfortable living space. Nestled in an amazing location, you'll enjoy the convenience of being within walking distance to an array of fantastic restaurants, shops, and local attractions.

    Natalya Ford EXP Realty, LLC

    22695 Washington St Unit 2, Leonardtown, MD 20650
  • 23635 Abraham Dr, Leonardtown, MD 20650
    23635 Abraham Dr, Leonardtown, MD 20650
    23635 Abraham Dr, Leonardtown, MD 20650
    /41

    $572,000 Sold Jun 09, 2025

    • 3,272 Sq Ft
    • $175/SF
    • 2 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 2004

    23635 Abraham Dr, Leonardtown, MD 20650

    Welcome Home to Comfort, Charm, and SpaceThis stunning Colonial is nestled in a peaceful, sought-after community — the perfect retreat with 6 bedrooms and 4 full baths. Just minutes from downtown Leonardtown, you’ll have easy access to charming shops, popular restaurants, and scenic waterfront views at the Wharf.From the moment you enter, you’ll feel right at home. The warm and inviting family

    Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
    • 40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      /30

      Est $759,409 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      40630 Breton Oaks Ln, Leonardtown, MD 20650
  • 20814 Deer Wood Park Dr, Leonardtown, MD 20650
    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    /35

    $610,000

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft

    20814 Deer Wood Park Dr, Leonardtown, MD 20650

    This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy on a beautifully treed 4 acre lot. The first floor features a private office/den, formal living room, and elegant dining room. The large kitchen includes a cozy breakfast nook and opens to a step-down family room with a slider leading to a screened-in porch—ideal for indoor-outdoor living.Upstairs, the

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, Leonardtown, MD 20650
  • 41416 Heritage Ln, Leonardtown, MD 20650
    41416 Heritage Ln, Leonardtown, MD 20650
    41416 Heritage Ln, Leonardtown, MD 20650
    /47

    $3,900 per month

    • 4 Beds
    • 2.5 Baths
    • 3,868 Sq Ft
    • House for Rent

    41416 Heritage Ln, Leonardtown, MD 20650

    This well-maintained 4-bedroom, 2.5-bath Grandhaven model sits on a flat lot with a backyard suitable for future fencing. The home offers a functional and stylish kitchen layout with a large island, walk-in pantry, butler’s pantry, quartz countertops, white cabinetry, and stainless steel appliances—including double ovens, electric cooktop, vented microwave, and dishwasher.The main level features

    Natalya Ford EXP Realty, LLC

    41416 Heritage Ln, Leonardtown, MD 20650
  • 39880 Lady Baltimore Ave, Leonardtown, MD 20650
    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    /51

    $415,000 Sold Jun 09, 2025

    • 1,348 Sq Ft
    • $308/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new vinyl flooring throughout, the Roof was replaced in 2019, the appliances are less than 2 years old, the Heat Pump was replaced in 2020, and much much more!This home features a huge pantry in the kitchen, a huge laundry room with even more cabinets for storage, a beautiful

    Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    • 23930 Susies Ln, Leonardtown, MD 20650
      23930 Susies Ln, Leonardtown, MD 20650
      23930 Susies Ln, Leonardtown, MD 20650
      /77

      Est $518,666 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,132 Sq Ft

      23930 Susies Ln, Leonardtown, MD 20650

      23930 Susies Ln, Leonardtown, MD 20650
  • 40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    40461 Old Breton Beach Rd, Leonardtown, MD 20650
    /41

    $700,000

    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Welcome to 40461 Old Breton Beach Road—a breathtaking waterfront retreat on the shores of the Potomac River in Leonardtown, Maryland. Nestled in one of Southern Maryland’s most scenic and peaceful communities, this coastal-style home offers the perfect blend of charm, functionality, and panoramic water views that will leave you speechless. Perfect for a primary or rental. From the moment you

    Dawn Riley RE/MAX One

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • 21684 Potomac View Dr, Leonardtown, MD 20650
    21684 Potomac View Dr, Leonardtown, MD 20650
    21684 Potomac View Dr, Leonardtown, MD 20650
    /25

    $447,000 Sold Jun 04, 2025

    • 1,504 Sq Ft
    • $297/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    21684 Potomac View Dr, Leonardtown, MD 20650

    3BR, 2Bath rancher with Front and Rear covered porches. Rear yard is ready for outdoor entertainment. Large side load garage with storage area over. Living Room with fireplace, dining area, open kitchen. No mandatory HOA, however the civic association is an optional fee.HVAC replaced a year ago.

    Terry Tenney Atlantic Southern Realty INC

    21684 Potomac View Dr, Leonardtown, MD 20650
    • 41435 Osborne Ln, Leonardtown, MD 20650
      41435 Osborne Ln, Leonardtown, MD 20650
      41435 Osborne Ln, Leonardtown, MD 20650
      /91

      Est $669,871 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,145 Sq Ft

      41435 Osborne Ln, Leonardtown, MD 20650

      41435 Osborne Ln, Leonardtown, MD 20650
  • 41535 Fairwood Ct, Leonardtown, MD 20650
    41535 Fairwood Ct, Leonardtown, MD 20650
    41535 Fairwood Ct, Leonardtown, MD 20650
    /67

    $750,000

    • 4 Beds
    • 4 Baths
    • 4,829 Sq Ft

    41535 Fairwood Ct, Leonardtown, MD 20650

    Stunning 4 Bed / 4 Bath Ranch Rambler in Sought-After Clark’s Rest CommunityWelcome to your dream home! Nestled in the highly desirable Clark’s Rest community, this stunning 4-bedroom, 4-bath Ranch Rambler is only one year old and loaded with upgrades with exceptional curb appeal and luxurious features throughout, this is a rare find that won’t last long. This modern home blends comfort, style,

    Ms. Stephanie M Lee EXP Realty, LLC

    41535 Fairwood Ct, Leonardtown, MD 20650
  • 20161 Tower Hill Rd, Leonardtown, MD 20650
    20161 Tower Hill Rd, Leonardtown, MD 20650
    20161 Tower Hill Rd, Leonardtown, MD 20650
    /56

    $395,000 Sold Jun 02, 2025

    • 1,661 Sq Ft
    • $238/SF
    • 2 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1990

    20161 Tower Hill Rd, Leonardtown, MD 20650

    This contemporary cape cod style home is it's own private retreat on over 3 acres. The main floor gives you a formal living room with vaulted celing and 2 sided woodstove/fireplace while also providing an additional family room that could easily be converted to a 3rd bedroom. The kitchen has been updated with granite counter tops, subway tiled backsplash, new appliances and more. Dining room

    Trish Wallmark RE/MAX One

    20161 Tower Hill Rd, Leonardtown, MD 20650
    • 23620 Pine Bluff Way, Leonardtown, MD 20650
      23620 Pine Bluff Way, Leonardtown, MD 20650
      23620 Pine Bluff Way, Leonardtown, MD 20650
      /27

      Est $640,877 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,400 Sq Ft

      23620 Pine Bluff Way, Leonardtown, MD 20650

      23620 Pine Bluff Way, Leonardtown, MD 20650
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /79

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality.The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your

    Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • 41918 Sara Ann Ct, Leonardtown, MD 20650
    41918 Sara Ann Ct, Leonardtown, MD 20650
    41918 Sara Ann Ct, Leonardtown, MD 20650
    /33

    $505,000 Sold Jun 02, 2025

    • 3,392 Sq Ft
    • $149/SF
    • 12 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2005

    41918 Sara Ann Ct, Leonardtown, MD 20650

    This beautiful two-story Colonial with a finished basement is perfectly situated in a prime location just minutes from downtown Leonardtown, offering easy access to quaint shops, restaurants, the wharf, and vibrant community events. With a traditional floor plan, the main level features durable vinyl plank flooring, a welcoming living room with a cozy gas fireplace, and a functional kitchen with

    Tracey Summers CENTURY 21 New Millennium

    41918 Sara Ann Ct, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 18

Maryland Leonardtown

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