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Homes for Sale near Leonardtown Middle School

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  • /79

    $669,900

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

    23534 Belmar Dr, Leonardtown, MD 20650

    PRICE REDUCTION! Discover unparalleled luxury at 23534 Belmar Drive, an extraordinary residence nestled in the prestigious Leonard’s Grant neighborhood of Leonardtown, MD. This impressive home boasts over 5,000 square feet of refined living space, seamlessly blending comfort, style, and modern functionality in one of St. Mary’s County’s most sought-after communities.Step inside to experience a

    Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
  • /40

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    40905 Knight Rd, Leonardtown, MD 20650

    Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland! This inviting home offers a perfect mix of comfort and practicality, featuring three spacious bedrooms and 2.5 baths—ideal for entertaining or everyday living.Sitting on a generous half-acre lot, the property provides plenty of space to enjoy the outdoors. The fenced backyard is perfect for gatherings, and the large patio and fire

    Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
  • /3

    $95,000

    • Land
    • 0.84 Acre
    • $113,095 per Acre

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Prime Build-Ready Lot – Bring Your Dream Home to Life!Discover the perfect canvas for your dream home on this beautiful [size] acre lot in [location]! This perc-tested property is ready for construction, offering the flexibility to bring your own builder or partner with Graham & Co Custom Creations to design and build a custom home tailored to your vision.Located in a serene

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • /85

    $695,000

    • 4 Beds
    • 3.5 Baths
    • 4,019 Sq Ft

    23055 Town Run Dr, Leonardtown, MD 20650

    Stunning Clarke Model by Quality Built HomesLocated in the desirable Meadows at Town Run, this 4-bedroom, 3.5-bath home offers over 4,000 square feet of living space, including a finished lower level. Built in 2021, this home is just a few years old and has been meticulously maintained.Enjoy a prime location with Duke Elementary and the library within walking distance, Downtown Leonardtown just 5

    Laura Bernth RE/MAX One

    23055 Town Run Dr, Leonardtown, MD 20650
  • /32

    $449,900

    • 3 Beds
    • 3 Baths
    • 2,028 Sq Ft

    22362 Armstrong Dr, Leonardtown, MD 20650

    Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MDNestled in the desirable Society Hill neighborhood of Leonardtown, this one-of-a-kind property offers a rare opportunity with its expansive double lot—a true gem in the community. While the home retains a timeless charm, it presents an exciting chance to add your personal touch and modern updates.Inside, you'll

    Chris Hill CENTURY 21 New Millennium

    22362 Armstrong Dr, Leonardtown, MD 20650
  • /4

    $95,000

    • Land
    • 1.00 Acre
    • $95,000 per Acre

    26181 S Sandgates Rd, Mechanicsville, MD 20659

    Discover the perfect opportunity to build your dream home on this 1-acre buildable lot at 26181 S Sandsgate Rd, Mechanicsville, MD. This flat lot comes with recorded percs, making it ready for development. Enjoy the privacy of a spacious property while still being conveniently located near local amenities. Don’t miss out on this prime piece of land!

    William Rabbitt The Southside Group Real Estate

    26181 S Sandgates Rd, Mechanicsville, MD 20659
  • /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
  • /13

    $375,000

    • 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 single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • /51

    $699,900

    • 3 Beds
    • 2.5 Baths
    • 3,478 Sq Ft

    23773 Meredith Ct, Hollywood, MD 20636

    Spacious home in desirable Hollywood location. (Abell's Ridge) The main level greets you with hardwood flooring in the Foyer. Large owners suite with two walk in closets. The owner's full bath features tile flooring, a double jetted soaking tub, separate shower.Four car garage with work area of garage heated. New HVAC in 2023. Fireplace has wood stove insert. Unfinished basement . Over 7

    Gloria Abell Coldwell Banker Jay Lilly Real Estate

    23773 Meredith Ct, Hollywood, MD 20636
  • /6

    $169,900

    • Land
    • 1.49 Acres
    • $114,027 per Acre

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Charming Cul-de-Sac Lot in Breton Oaks – No HOA!Discover the perfect place to build your dream home on this beautiful, private lot located in the peaceful cul-de-sac of Breton Oaks. This small, custom-built subdivision offers a tranquil setting, with all homes in the neighborhood uniquely designed by St. Maries Builders. You can choose to build with them or bring your own builder to bring your

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /5

    $535,000

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! Both are presently rented. The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • /2

    $35,000

    • Land
    • 0.55 Acre
    • $63,636 per Acre

    26379 Fielding Rd, Hollywood, MD 20636

    Perc Approved buildable lot in wateroriented Hollywood Shores Subdivision. Community pool and boat ramp available within subdivision. Preliminary site plan was drawn up by DH Steffens Surveying.Great deal for a nice buildable lot in a great neighborhood with water access!!!!!Tax ID:1906034942

    Bradley Franzen/Retired Franzen Realtors, Inc.

    26379 Fielding Rd, Hollywood, MD 20636
  • /29

    $999,900

    • Land
    • 10 Acres
    • $98,029 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this breathtaking 10.2-acre waterfront lot overlooking the serene Breton Bay. This rare gem is not just a piece of land; it's an invitation to create a life of adventure, tranquility, and natural beauty.Endless Possibilities:With perc approval already in place, this stunning property is ready for your dream home. Imagine waking up to

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • /4

    $120,000

    • Land
    • 0.85 Acre
    • $141,176 per Acre

    21765 Point Lookout Rd, Leonardtown, MD 20650

    Property has been cleared and is ready for it's new owner. Conveniently located, close to shopping, groceries, restaurants and PAX. Do not enter home; home is not structurally sound.

    Amy Scott OE Realty

    21765 Point Lookout Rd, Leonardtown, MD 20650
  • /7

    $9,999

    • Land
    • 0.92 Acre
    • $10,868 per Acre

    26819 Valley Cir, Mechanicsville, MD 20659

    Buyer is responsible for their own due diligence.

    Bryce Jenifer Keller Williams Legacy

    26819 Valley Cir, Mechanicsville, MD 20659
  • /7

    $225,000

    • Land
    • 2.56 Acres
    • $87,891 per Acre

    26350 Three Notch Rd, Mechanicsville, MD 20659

    **Prime Commercial Opportunity on 2.56 Acres with Excellent Visibility!**This **corner lot** boasts approximately 750 feet of road frontage on busy Route 235 northbound, offering fantastic visibility and accessibility for your business. Zoned **RCL**, this property provides a wide range of commercial possibilities (county verification required), making it a flexible choice for

    Jessica Raley CENTURY 21 New Millennium

    26350 Three Notch Rd, Mechanicsville, MD 20659
  • /9

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,150 Sq Ft

    26188 Skyview Dr, Hollywood, MD 20636

    JUST REDUCED WHAT A DEAL = HOME NEEDS SOME WORK = VACANT = WATERFRONT ON COLES CREEK. SELLER WILL PAY $40,000.00 TOWARD HOME IMPROVEMENTS IF SETTLEMENT CAN BE WITHIN 30 DAYS.

    Glen Elrod Elrod & Associates Real Estate, Inc

    26188 Skyview Dr, Hollywood, MD 20636
  • /2

    $225,000

    • Land
    • 8 Acres
    • $30,000 per Acre

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning 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. The

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, Leonardtown, MD 20650
  • /2

    $86,900

    • Land
    • 1.68 Acres
    • $51,726 per Acre

    22020 Victorian Dr, California, MD 20619

    Build you own home on this 1.677 acre lot in a great location!! No HOA in this community. The property has been perced and it's ready for your plans. Plat is available showing the perc location.

    Dawn Wood O'Brien Realty ERA Powered

    22020 Victorian Dr, California, MD 20619
  • /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2012646, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2012646, Leonardtown, MD 20650
  • /3

    $190,000

    • Land
    • 8 Acres
    • $25,066 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, Leonardtown, MD 20650
  • /3

    $195,000

    • Land
    • 1.87 Acres
    • $104,278 per Acre

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left in Breton Knolls. Breton Knolls is a 24 lot subdivision in Leonardtown with 1 - 7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • /3

    $200,000

    • Land
    • 4.83 Acres
    • $41,408 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, 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
  • /2

    $99,000

    • Land
    • 0.19 Acre
    • $521,053 per Acre

    42278 Allison Dr, Mechanicsville, MD 20659

    This buildable lot comes with a septic system, which is a huge value!! Located in the Saint Mary's Beach neighborhood with partial water view! All the hard work is done for you! Impact fee is paid! Owner has permit for 3 bedroom, 2 bath colonial style home. This price INCLUDES a septic system to be installed after settlement at the appropriate time in the building process. This lot is

    Michelle Camaioni RE/MAX Closers

    42278 Allison Dr, Mechanicsville, MD 20659
  • /2

    $35,000

    • Land
    • 0.37 Acre
    • $94,595 per Acre

    0 Holly Ln Unit MDSM2023572, Mechanicsville, MD 20659

    Welcome to your future haven on this expansive 16,117 square foot lot, perfectly positioned near the Cape St Mary's Marina at the end of the street. This prime location offers a harmonious blend of tranquility and convenience, with nearby attractions such as Seabreeze Restaurant, Snow Hill Park, Budds Creek Motocross Park, Potomac Speedway, and the breathtaking Chesapeake Bay. Enjoy seamless

    Samara Dinnius JPAR Real Estate Professionals

    0 Holly Ln Unit MDSM2023572, Mechanicsville, MD 20659
  • /2

    $229,991

    • 4 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    24399 Morgan Rd, Hollywood, MD 20636

    Diamond in the rough! Solid vintage home on large corner lot is ready for one lucky owners sweat equity or for easy renovation financing. Completed improvements are in; new roof, economical oil fired boiler for wonderful radiant hot water baseboard heat, replacement thermopane windows, environmentally sound mound septic system and more! List price reflects being sold AS IS. Visit soon and see

    Juan Aranda CENTURY 21 New Millennium

    24399 Morgan Rd, Hollywood, MD 20636
  • /2

    $60,000

    • Land
    • 2.25 Acres
    • $26,667 per Acre

    0 Loveville Rd, Mechanicsville, MD 20659

    Samara Dinnius JPAR Real Estate Professionals

    0 Loveville Rd, Mechanicsville, MD 20659
  • /7

    $675,000 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
  • /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
  • /6

    $399,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,530 Sq Ft

    42278 Allison Dr, Mechanicsville, MD 20659

    Embrace a relaxed waterfront lifestyle in the tranquil community of St. Mary's Beach with this to-be-built home, where the soothing sounds of the Patuxent River beckon you to unwind. Enjoy the freedom of no HOA while being just a short stroll from the sandy shores and sparkling waters. Delight in leisurely dining experiences at Sea Breeze Restaurant and Bar or indulge in the charm of Suzanna's

    Michelle Camaioni RE/MAX Closers

    42278 Allison Dr, Mechanicsville, MD 20659
  • /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
  • /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
  • /2

    $680,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,784 Sq Ft

    43478 Greg St, Hollywood, MD 20636

    Fabulous Like-New Rambler in Sought-After Twin Ponds!Step into comfort and style with this impeccably maintained 4-bedroom, 3.5-bath Tappahannock Model built by Quality Built Homes. This spacious rambler features a fully finished basement and a thoughtfully designed layout ideal for one level living or a multi generational set up. Located in the highly desirable Twin Ponds community and zoned for

    Sarah Mulford-Martin EXP Realty, LLC

    43478 Greg St, Hollywood, MD 20636
  • /2

    $750,000 Coming Soon

    • 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
  • /14

    $540,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,356 Sq Ft

    20955 Aster Dr, Callaway, MD 20620

    Well maintained by the original owners, this beautiful home sits on a private, 2-acre lot. Recent updates include a roof (8 years old), Heat pump & AC coil (2020), and a hot water heater (2025). The interior has been freshly painted, and new LVP flooring on the main level. Enjoy outdoor living on the maintenance-free deck, replaced in 2012, or relax on the charming front porch. The family room

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    20955 Aster Dr, Callaway, MD 20620
  • /6

    $843,000 Coming Soon

    • 5 Beds
    • 4 Baths
    • 4,648 Sq Ft

    40738 Bobwhite Ln, Leonardtown, MD 20650

    A Rare Gem in Avenmar – A Must-See Estate at the End of a Tranquil Cul-de-SacWelcome to 5,242 sq. ft. of pure luxury nestled on 3.52 beautifully landscaped acres. This exquisite home offers five spacious bedrooms, four full bathrooms, and over 4,600 finished square feet designed for comfort and elegance.Every room is thoughtfully appointed, featuring high-end finishes and an open, inviting

    Jessica Raley CENTURY 21 New Millennium

    40738 Bobwhite Ln, Leonardtown, MD 20650
  • /77

    $479,000 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 2,645 Sq Ft

    41326 Margrove Cir, Leonardtown, MD 20650

    Stop the Car—This Is the One!Welcome to this stunning and expansive 3,290 sq. ft. end-unit townhome that offers the perfect blend of elegance, comfort, and unbeatable location. From the moment you step inside, you’ll be captivated by the rich hardwood flooring on the main level and the abundance of natural light that pours in through the oversized end-unit windows.The heart of the home is the

    Jessica Raley CENTURY 21 New Millennium

    41326 Margrove Cir, Leonardtown, MD 20650
  • /126

    $5,950,000 Coming Soon

    • 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
  • /2

    $325,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    26290 Skyview Dr, Hollywood, MD 20636

    Coming Soon! 3 bed, 1.5 bath home in the water-privileged Hollywood Shores neighborhood.

    Mithra Uhall Infinitas Realty Group

    26290 Skyview Dr, Hollywood, MD 20636

Showing Results 41 - 80, Page 2 of 3

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