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Homes for Sale near Leonardtown Middle School

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  • /68

    $599,900

    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft

    40855 Spring House Ln, Leonardtown, MD 20650

    Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven

    Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • /8

    $200,000

    • Land
    • 1.2 Acres
    • $166,667 per Acre

    0 Saint Johns Rd, Hollywood, MD 20636

    Rare opportunity to own prime land in Hollywood, MD! This vacant, flat, and open parcel sits at the high-visibility intersection of Three Notch Road and St. John’s Road, offering exceptional exposure and accessibility. Public water and sewer are adjacent to the property, creating outstanding development potential. Ideal for a variety of uses—including a farmers market, roadside produce stand,

    John Gatton CENTURY 21 New Millennium

    0 Saint Johns Rd, Hollywood, MD 20636
  • /28

    $149,900

    • Land
    • 2.28 Acres
    • $65,746 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, Leonardtown, MD 20650
  • /48

    $695,990

    • 3 Beds
    • 2 Baths
    • 2,055 Sq Ft

    26669 Queentree Rd, Mechanicsville, MD 20659

    Price drop and Endless Opportunities on a Historic Gem! This beautifully maintained 100+ year old home sitting on 11.82 acres, combines classic charm with modern amenities. Featuring a wrap-around porch, original craftsman staircase, 3 bedrooms, 2 baths, with fully finished attic perfect for an office. The main level bath includes jacuzzi tub and walk-in shower. Enjoy outdoor living with a new

    Deb Kollar Coldwell Banker Premier

    26669 Queentree Rd, Mechanicsville, MD 20659
  • /58

    $499,900

    • 3 Beds
    • 2 Baths
    • 3,140 Sq Ft

    43979 Drum Cliff Rd, Hollywood, MD 20636

    Enjoy waterfront living with this cottage style home offering breathtaking views of the Patuxent River and St. Thomas Creek. The open main-level floor plan of this 3BR 2FB home captures water views from most areas of the home, as does the rear of the fully finished walkout-level basement. The spacious walk-up attic could potentially offer future expansion into a third floor, perhaps maybe with

    Ken Phipps CENTURY 21 New Millennium

    43979 Drum Cliff Rd, Hollywood, MD 20636
  • /7

    $200,000

    • Land
    • 2.56 Acres
    • $78,125 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 entrepreneurs and

    Jessica Raley CENTURY 21 New Millennium

    26350 Three Notch Rd, Mechanicsville, MD 20659
  • /10

    $205,000

    • Land
    • 5 Acres
    • $41,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • /6

    $24,900

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

    0 Long Leaf Ln Unit MDSM2026482, 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 MDSM2026482, Leonardtown, MD 20650
  • /40

    $599,000

    • 4 Beds
    • 2 Baths
    • 1,940 Sq Ft

    27273 Holly Ln, Mechanicsville, MD 20659

    27273 Holly Lane is a home which went under a full renovation costing well over $175,000.00 in recent years. Including foundation sealing, full interior, roof, windows, full kitchen and baths. Water view home in the Sandgate's community of Mechanicsville. Situated on scenic Cat Creek, just off the Patuxent River, this property offers a unique opportunity to enjoy the best of Maryland’s lifestyle.

    Rudy Carrico Baldus Real Estate, Inc.

    27273 Holly Ln, 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 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, 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
  • /30

    $1,750,000

    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft

    0 Bayside Rd, Leonardtown, MD 20650

    Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The

    Bonnie Haley Haley Family Realty

    0 Bayside Rd, Leonardtown, MD 20650
  • /9

    $399,000

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

    26188 Skyview Dr, Hollywood, MD 20636

    JUST REDUCED $100,000.00 WHAT A DEAL = HOME NEEDS SOME WORK = IT'S AN INVESTORS DREAM REMODLE AND SELL IT AND MAKE SOME MONEY= VACANT = WATERFRONT ON COLES CREEK.

    Glen Elrod Elrod & Associates Real Estate, Inc

    26188 Skyview Dr, Hollywood, MD 20636
  • /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 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
  • /3

    $175,000

    • Land
    • 7.58 Acres
    • $23,087 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
  • /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

    $149,900

    • Land
    • 1.44 Acres
    • $104,097 per Acre

    20265 Hawks Way, Leonardtown, MD 20650

    Prime 1.44-Acre Buildable Lot in Leonardtown, MD Welcome to 20265 Hawks Way, a fantastic opportunity to build your dream home on a spacious 1.44-acre parcel on a quiet street. This generous lot offers a blank canvas — cleared and ready for construction — surrounded by other new construction homes that bring a sense of neighborhood and modern living while maintaining a peaceful, rural feel.

    Mark Frisco CENTURY 21 New Millennium

    20265 Hawks Way, Leonardtown, MD 20650
  • /2

    $999,000

    • Land
    • 8 Acres
    • $124,875 per Acre

    24699 Hollywood Rd, Hollywood, MD 20636

    Beautiful 8 acre corner lot in Hollywood, Md. Over 1500 feet of road frontage on Rt 235 and Hollywood/Leonardtown Rd combined. Vacant home that possibly could be renovated. Presently zoned R but could be zoned commercial. May possibly be subdivided in to building lots. Many possible uses for this property. Private business, car dealership, etc. Do not enter house

    Steve Lowe United Real Estate Premier

    24699 Hollywood Rd, Hollywood, MD 20636
  • /46

    $489,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland.

    Laura Bernth RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650
  • /41

    $479,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650

    **TO BE BUILT**** Homesite 141 - Oakley D1 End Unit ***October Delivery**** ***Choose your color scheme from of our available options** 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous

    Laura Bernth RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
  • /3

    $779,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,745 Sq Ft

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Welcome to Breton Oaks—one of Leonardtown’s most sought-after communities—where this beautifully designed to-be-built home by Mednick Construction offers the perfect blend of modern farmhouse style and peaceful, wooded surroundings. Tucked away on a private, wooded lot on a quiet cul-de-sac, this thoughtfully crafted residence delivers timeless curb appeal paired with today’s most desirable

    Charlotte Long EXP Realty, LLC

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /45

    $449,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 110 Madison D1: *** Late April Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an

    Laura Bernth RE/MAX One

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
  • /46

    $489,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 132 TO BE BUILT New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and

    Laura Bernth RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650
  • /28

    $579,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • /2

    $590,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,123 Sq Ft

    23282 Lindsay Dr, Leonardtown, MD 20650

    4-year young home built in 2022 — Coming Soon! This 3-level home features 5 bedrooms, 3.5 bathrooms, and is well-maintained throughout. VA assumable loan at 4.5% available for qualified veteran buyers.--loan balance is $464K. Professional photos coming soon!

    Nichelle Jeter Samson Properties

    23282 Lindsay Dr, Leonardtown, MD 20650
  • /4

    $639,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,261 Sq Ft

    23621 Margrave Dr, Leonardtown, MD 20650

    Welcome to this beautifully maintained, single-owner Colonial in the highly sought-after Leonard’s Grant community. Blending classic charm with thoughtful upgrades, this home offers both comfort and functionality throughout. The main level features wood flooring in the living and dining areas, a private dining room, and a cozy fireplace. The spacious kitchen boasts stainless steel appliances,

    Lauren Garner EXP Realty, LLC

    23621 Margrave Dr, Leonardtown, MD 20650
  • /50

    $680,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,992 Sq Ft

    41488 Pensive St, Leonardtown, MD 20650

    Updated Photos coming in a couple weeks! Welcome to this Belmont model in Leonard’s Grant, offering a spacious layout and thoughtful design throughout. As you enter the home, you’re welcomed by hardwood floors, a grand entryway, and a beautiful staircase that creates an inviting first impression.To the right, French doors open to a large room that works well as a home office or additional

    Heather Foster RE/MAX One

    41488 Pensive St, Leonardtown, MD 20650
  • /4

    $725,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 2,834 Sq Ft

    41655 Church St, Leonardtown, MD 20650

    Built in 1875, this substantial 2,800 sq ft residence offers a rare opportunity to own a large historic home in highly desirable Leonardtown. Featuring 5 bedrooms and 2 bathrooms, the property showcases classic architecture with a formal living room and dining room, and enduring period details. Original features include a beautiful antique stamped tin ceiling and two fireplaces, adding

    Chris Norris Topside Realty

    41655 Church St, Leonardtown, MD 20650
  • /2

    $649,000 Coming Soon

    • 5 Beds
    • 5 Baths
    • 2,756 Sq Ft

    43430 Browns Ln, Leonardtown, MD 20650

    This unique property has so much to offer and has been a great family home, however owners are moving and have found their next home. Well cared for 4 BR, 2 full BA, 2 half BA home has 2,116 sq. ft, wood stove, porch, deck, and garage which is currently used as an exercise room. The large detached garage, 28 x 40, has a 640 sq. ft. in-law suite on the upper level w/own laundry rm and kitchenette.

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns Ln, Leonardtown, MD 20650
  • /2

    $715,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft

    41389 Holiday Ct, Leonardtown, MD 20650

    Welcome to 41389 Holiday Court, a stunning QBH Sotterley model located in the highly sought-after QBH community of Leonard’s Grant! Perfectly positioned on a desirable corner lot, this beautifully maintained 5-bedroom, 3.5-bath home offers the ideal blend of space, functionality, and thoughtful upgrades throughout. Step inside to find gorgeous hardwood floors flowing through the main level,

    Laura Bernth RE/MAX One

    41389 Holiday Ct, Leonardtown, MD 20650
  • /2

    $520,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,926 Sq Ft

    23207 Moakley St, Leonardtown, MD 20650

    Professional photos coming! Charming home located in Leonardtown, offering the perfect combination of privacy and convenience. Situated on a flat 1-acre lot with no HOA, this property gives you space to spread out while still being just minutes from shopping, dining, and everything Leonardtown has to offer.Inside, you’ll find wood floors throughout the entire first level and a bright white

    Heather Foster RE/MAX One

    23207 Moakley St, Leonardtown, MD 20650
  • /2

    $675,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 4,040 Sq Ft

    24065 Pappys Way, Hollywood, MD 20636

    Beautiful colonial situated on a 4.12 acre secluded lot backing to 28 acres of Forest Conservation area! This home has it all including 4 bedrooms, 3 1/2 bathrooms, finished basement with kitchen and more. As you enter the foyer the hardwood floors lead you to a den/office perfect for working from home and extra space. The kitchen includes upgraded stainless appliances, a breakfast area, and

    Kelly Padgett CENTURY 21 New Millennium

    24065 Pappys Way, Hollywood, MD 20636
  • /2

    $680,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft

    23592 Belmar Dr, Leonardtown, MD 20650

    Photos to come.QBH Belmont model with a beautiful Sunroom.

    Heather Foster RE/MAX One

    23592 Belmar Dr, Leonardtown, MD 20650
  • /2

    $655,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    23012 S Pembrook Dr, Hollywood, MD 20636

    SPECTACULAR COLONIAL IS SOUGHT AFTER FORREST FARMS. HOME HAS BEEN METICULOUSLY MAINTAINED AND MANY RECENT UPDATES INLUDES...NEW PRIMARY BATH, NEW APPLIANCES, LAUNDRY MOVED TO BEDROOM LEVEL FROM BASEMENT, FRESH LIGHT FIXTURES AND FRESHENED UP PAINT. GREAT FLOOR PLAN FEATURES LARGE OFFICE, OPEN KITCHEN TO FAMILY ROOM, HUGE DINING ROOM AND INCREDIBLE PRIMARY SUITE WITH GORGEOUS BATH. 3 OTHER

    Jennifer Mullennix CENTURY 21 New Millennium

    23012 S Pembrook Dr, Hollywood, MD 20636
  • /2

    $624,900 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,155 Sq Ft

    24475 Broad Creek Dr, Hollywood, MD 20636

    Welcome to this immaculate Ashford model in the highly desirable Broad Creek community, offering over 4,300 square feet of beautifully finished living space designed for comfort, style, and functionality. Step inside to a grand two-story foyer highlighted by hardwood flooring and recessed lighting throughout the main level, creating a bright and welcoming first impression. The home features five

    Matthew Burgan Infinitas Realty Group

    24475 Broad Creek Dr, Hollywood, MD 20636
  • /2

    $524,900 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft

    24433 Broad Creek Dr, Hollywood, MD 20636

    Welcome to 24433 Broad Creek — a beautifully maintained 3-bedroom, 2.5-bath colonial located in the highly sought-after Broad Creek community. This inviting home offers a bright and open layout designed for both comfortable living and effortless entertaining. Step inside to discover an open-concept main level filled with abundant natural light and a seamless flow between the living, dining, and

    Matthew Burgan Infinitas Realty Group

    24433 Broad Creek Dr, Hollywood, MD 20636

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