38

Leonardtown, MD Houses for Sale

Section Image Section Image
  • 40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    40534 Miss Ettas Way, Leonardtown, MD 20650
    /31

    $480,000

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

    40534 Miss Ettas Way, Leonardtown, MD 20650

    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 walk-in pantry—ideal for any home

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (240) 697-2564

    40534 Miss Ettas Way, 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 One

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • 21745 Pinehurst Ct, Leonardtown, MD 20650
    21745 Pinehurst Ct, Leonardtown, MD 20650
    /2

    $605,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,860 Sq Ft

    21745 Pinehurst Ct, Leonardtown, MD 20650

    Desirable Breton Bay Brick Colonial with a NEW ROOF! Enter the soaring two-story foyer of this 4-bedroom, 2.5 bath home, and take note of the refinished hardwood floors, wide staircase with wrought iron railings, and Palladian window that allows for lots of natural light. Head past the shiplap wall treatment into the eat-in kitchen that features tall white cabinets, newer appliances, beautiful

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 230-4358

    21745 Pinehurst Ct, Leonardtown, MD 20650
  • 41650 Matthew Ct, Leonardtown, MD 20650
    41650 Matthew Ct, Leonardtown, MD 20650
    41650 Matthew Ct, Leonardtown, MD 20650
    /8

    $575,000

    • 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
  • 41435 Osborne Ln, Leonardtown, MD 20650
    41435 Osborne Ln, Leonardtown, MD 20650
    41435 Osborne Ln, Leonardtown, MD 20650
    /59

    $675,000

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

    41435 Osborne Ln, Leonardtown, MD 20650

    Built in 2018, this home feels better than new with fresh paint and modern updates throughout! With 6 bedrooms, 4.5 bathrooms, and multiple living spaces, there’s room for every member of the household, long-term guests, or effortless entertaining. Osborne Lane greets you with a welcoming front porch and porch swing to enjoy mornings or evenings overlooking the tree-lined, sidewalked streets.

    Delaney Burgess RE/MAX United Real Estate

    41435 Osborne 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
    /53

    $569,000

    • 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,

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, 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
    /61

    $689,900

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

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream come true for boaters and anglers alike.Inside, you’ll find a

    Mileah Walker Real Broker, LLC

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • 22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    /65

    $649,000

    • 4 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    22626 Chickadee Ln, Leonardtown, MD 20650

    Welcome to 22626 Chickadee Lane—an exceptional 4-bedroom, 3.5-bath home nestled on a serene 2-acre lot in the highly sought-after Avenmar neighborhood of Leonardtown. This elegant property offers the perfect blend of privacy, space, and convenience with an open-concept layout that is flooded with natural light and designed for comfortable living and entertaining.Inside, you'll find

    Matthew Burgan Infinitas Realty Group

    22626 Chickadee Ln, Leonardtown, MD 20650
  • 41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    /99

    $635,000

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft

    41402 Silver Charm Ct, Leonardtown, MD 20650

    Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of Leonard's Grant community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field. Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches.

    Kelly Padgett CENTURY 21 New Millennium

    41402 Silver Charm Ct, Leonardtown, MD 20650
  • 20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    /56

    $574,900

    • 4 Beds
    • 3.5 Baths
    • 3,465 Sq Ft

    20919 Ridge Path Way, Leonardtown, MD 20650

    Nestled on a serene and private 3.29-acre lot—plus an additional 0.5-acre parcel—20919 Ridge Path Way offers the perfect balance of seclusion and convenience in the heart of Leonardtown. This professionally upgraded 4-bedroom, 3.5-bath home delivers both peace of mind and high-end comfort with all major systems and appliances less than 5 years old.Step inside and experience a beautifully

    Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
  • 23242 Clarks Rest Rd, Leonardtown, MD 20650
    23242 Clarks Rest Rd, Leonardtown, MD 20650
    23242 Clarks Rest Rd, Leonardtown, MD 20650
    /52

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,296 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 nearly 3,300 square feet with 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

    Matthew Burgan Infinitas Realty Group

    23242 Clarks Rest Rd, Leonardtown, MD 20650
  • 39825 Sweetpea Ln, Leonardtown, MD 20650
    39825 Sweetpea Ln, Leonardtown, MD 20650
    39825 Sweetpea Ln, Leonardtown, MD 20650
    /80

    $790,000

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft

    39825 Sweetpea Ln, Leonardtown, MD 20650

    Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 feet of water frontage, this 4-bedroom, 3.5-bath home offers peace, privacy, and panoramic views. Inside, you'll find 2,408 square feet of comfortable living space featuring a cozy fireplace, wood stove, and large windows that invite the beauty of the outdoors in. The expansive deck is perfect for entertaining

    Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • 20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    /41

    $615,000

    • 5 Beds
    • 3.5 Baths
    • 3,061 Sq Ft

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    Welcome to this well-built colonial on a corner lot in the picturesque corner Chestnut Ridge neighborhood! With over 3,000 finished square feet, 5 bedrooms, and 3.5 bathrooms, this home is full of charm, character, and thoughtful craftsmanship.Situated on 2.11 acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the

    Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge Dr, 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
    /45

    $589,000

    • 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,

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, 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

    Dawn Riley RE/MAX One

    40461 Old Breton Beach Rd, 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
  • 23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    /59

    $610,000

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    **Custom Floorplan** Front Load Garage with expanded guest parking on driveway, Upgraded cabinets, Countertops, and custom Primary suite walk in frameless glass shower. Built on an oversized premium corner lot. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which transfers to the new homeowner. VA assumable

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /32

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    Are you dreaming of living on the water? This is your perfect opportunity! Well maintained rambler featuring waterfront, pier with boatlift, sunroom, 2-car attached garage, 1-car detached garage, 2-car carport. Gorgeous back yard, perfect for entertaining and spending those summer nights with friends and family. Get on your boat whenever the mood strikes you. This is the perfect home to just

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • 41810 Chelsey Faye Ln, Leonardtown, MD 20650
    41810 Chelsey Faye Ln, Leonardtown, MD 20650
    41810 Chelsey Faye Ln, Leonardtown, MD 20650
    /7

    $720,000 New Construction

    • 4 Beds
    • 4 Baths
    • 2,650 Sq Ft

    41810 Chelsey Faye Ln, Leonardtown, MD 20650

    Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom Creations. Building a custom home allows you to choose between the standard home on a crawl space or opt for a basement foundation for an additional cost, giving you the opportunity to personalize this beautiful dwelling to your exact needs. If there is some other

    Jessica Ascenzo JPAR Real Estate Professionals

    41810 Chelsey Faye Ln, 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
  • 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
  • 0 Wathen Rd, Leonardtown, MD 20650
    0 Wathen Rd, Leonardtown, MD 20650
    /2

    $831,025 New Construction

    • 5 Beds
    • 4 Baths
    • 4,700 Sq Ft

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning 7.5-acre lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen.

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, 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
  • 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
  • 41536 Fairwood Ct, Leonardtown, MD 20650
    41536 Fairwood Ct, Leonardtown, MD 20650
    41536 Fairwood Ct, Leonardtown, MD 20650
    /85

    $599,900

    • 4 Beds
    • 3.5 Baths
    • 3,308 Sq Ft

    41536 Fairwood Ct, Leonardtown, MD 20650

    Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage

    Teresa Klopfer RE/MAX Realty Group

    41536 Fairwood Ct, Leonardtown, MD 20650
  • 41535 Singletree Dr, Leonardtown, MD 20650
    41535 Singletree Dr, Leonardtown, MD 20650
    41535 Singletree Dr, Leonardtown, MD 20650
    /54

    $530,000

    • 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. 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, you’ll find four spacious bedrooms, while

    Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
  • 20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    20959 Redgate Ln, Leonardtown, MD 20650
    /13

    $239,000

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some well-deserved TLC.This

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • 41900 Nazareth Ct, Leonardtown, MD 20650
    41900 Nazareth Ct, Leonardtown, MD 20650
    41900 Nazareth Ct, Leonardtown, MD 20650
    /28

    $470,000

    • 4 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    41900 Nazareth Ct, Leonardtown, MD 20650

    Welcome to the Academy Hills of Leonardtown. The main level features a traditional floor plan, recent upgrades including new carpet August 2025, stainless steel kitchen appliances, plenty of cabinet space, a formal dining room, and a convenient powder room. Major system updates include a brand-new Roof and a new HVAC system for added peace of mind.Upstairs, newly installed banisters, the

    Marizel Brewington RE/MAX One

    41900 Nazareth Ct, Leonardtown, MD 20650
  • 21056 Woodmere Dr, Leonardtown, MD 20650
    21056 Woodmere Dr, Leonardtown, MD 20650
    21056 Woodmere Dr, Leonardtown, MD 20650
    /56

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    21056 Woodmere Dr, Leonardtown, MD 20650

    Nice Colonial with Covered Front Porch with concrete, Brick paver sidewalk and step, front load two car garage with exterior door to back yard. Storm Front Door with Side lights, Formal Living Room with Crown Molding, Dining Room Crown and Chair Molding, Hardwood Flooring in Foyer, Hall and Powder Room. Nice Kitchen with Center Island granite countertops, ceramic backsplash, Ceiling Light, New

    Kathryn Mausen Coldwell Banker Jay Lilly Real Estate

    21056 Woodmere Dr, 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

    This property is back on the market. This is your gain. 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

    Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, 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,

    Travis Gray Engel & Völkers Annapolis

    41505 Knight Rd, Leonardtown, MD 20650
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    /10

    $1,999,999

    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • 41815 Chelsey Faye Ln, Leonardtown, MD 20650
    41815 Chelsey Faye Ln, Leonardtown, MD 20650
    41815 Chelsey Faye Ln, Leonardtown, MD 20650
    /3

    $530,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home is a modestly sized one story design that is loaded with all the necessities. Beautiful white siding and stained timber accents are perfect material choices for the farmhouse style. Offering an open main level with one large space for living and dining. The family room has a high ceiling. Enjoy the cozy ambiance of this home

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • 23849 Point Lookout Rd, Leonardtown, MD 20650
    23849 Point Lookout Rd, Leonardtown, MD 20650
    /2

    $335,000 Coming Soon

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

    23849 Point Lookout Rd, Leonardtown, MD 20650

    More Photos to come on 9/16. 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. Neer 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.

    Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
  • 22323 Saint Clements Ave, Leonardtown, MD 20650
    22323 Saint Clements Ave, Leonardtown, MD 20650
    /2

    $249,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    22323 Saint Clements Ave, Leonardtown, MD 20650

    Welcome to 22323 Saint Clements Avenue, a rare and exciting opportunity to create your dream waterfront retreat or a lucrative investment property. Nestled on the serene shores of the Potomac River, this charming 2-bedroom, 2-bath cottage offers stunning water views, a private pier, and a detached garage—all on a generous lot in one of Southern Maryland’s most desirable waterfront

    Matthew Burgan Infinitas Realty Group

    22323 Saint Clements Ave, Leonardtown, MD 20650
  • 42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    /2

    $559,900 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    42043 Starlight Dr, Leonardtown, MD 20650

    Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, Leonardtown, MD 20650
  • 21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    /4

    $125,000

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    ONLINE AUCTION: Bidding begins 9/9/2025 @ 10:00 AM. Bidding ends 9/11/2025 @ 11:00 AM. List Price is Suggested Opening Bid. Deposit: $15,000. Single Family Home located in the Belvidere Woodland area.Located on +/- 40,000 SF of land, this property is JUST MINUTES to the St. Mary's State Park.Easy access to major traffic artery St. Andrew's Church Rd.

    Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Houses for Sale in Leonardtown, MD

Why Live in Leonardtown

Leonardtown is a Southern Maryland community on the rise, with the population nearly doubling between 2010 and 2020. “It’s one of the fastest-growing municipalities in Maryland,” says Jimmy Hayden , a Leonardtown native and Realtor with Re/Max Realty Group. ...

Learn more about living in Leonardtown

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 29 days on the market compared to the national average of 52 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $549,900, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$549,900
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$442,950
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$198
Number of Homes for Sale
34
Last 12 months Home Sales
135
Months of Supply
3.00
Median List Price
$565,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

In Leonardtown, there are currently 38 houses for sale, offering an array of options for potential buyers. With houses priced between $125,000 to $20,000,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Leonardtown is $565,950, while the average sale price is $571,130, offering insights into the local housing market. On average, houses spend 29 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Leonardtown, MD and find the perfect place to call home.

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