100

Homes for Sale near Leonardtown Middle School

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  • /28

    $99,000

    • Land
    • 2.28 Acres
    • $43,421 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
  • /44

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    Located in Clark's Rest, this home features Marrick's Kensington floor plan, with a covered front entry and separate covered sitting porch. Inside, a two-story foyer features hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room offers flexibility for a home office, library, study, or playroom. The dining room connects through the butler's pantry

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn Dr, Leonardtown, MD 20650
  • /54

    $475,000

    $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    40659 Klear Ct, Leonardtown, MD 20650

    Buyers, come take a look. The estate just dropped the price by $10,000 (08/17/2026)This is an estate sale being sold AS-IS. The Estate will not make any repairs. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and 2 full baths and the laundry room on the upper level. The main

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650
  • /15

    $374,900

    $25K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS—ANY RENTAL ADVERTISEMENT FOR THIS PROPERTY IS FRAUDULENT. The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, Leonardtown, MD 20650
  • /2

    $424,900

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    22386 Laceys Ln, California, MD 20619

    Welcome to 22386 Laceys Lane in California, Maryland! Nestled on a quiet cul-de-sac, this spacious 4-bedroom, 3-bath home offers the perfect blend of comfort, functionality, and everyday living. Step inside to discover large, open common areas designed for gathering with family and friends, while an abundance of natural light fills the home, creating a warm and inviting atmosphere throughout. The

    Matthew Burgan Infinitas Realty Group

    22386 Laceys Ln, California, MD 20619
  • /22

    $300,000

    • Land
    • 1.51 Acres
    • $198,675 per Acre

    41708 Fenwick St, Leonardtown, MD 20650

    Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated

    Tig Wright Redfin Corp

    41708 Fenwick St, Leonardtown, MD 20650
  • /31

    $364,900

    $4K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,184 Sq Ft

    45674 Bethfield Way, California, MD 20619

    Welcome to this exceptionally well-maintained 3-level townhome in the desirable Elizabeth Hills community. Lovingly cared for and featuring minimal wear, this home has experienced very little traffic over the years, offering a move-in-ready opportunity that truly shows pride of ownership. The main level is designed for both everyday living and entertaining, showcasing a beautiful kitchen with

    Stella Barbour NOVA Brokers, LLC.

    45674 Bethfield Way, California, MD 20619
  • /12

    $550,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    41888 Jenkins Ct, Leonardtown, MD 20650

    Interior Photos Coming Soon! Expected on market date is Sept 1, 2026Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown

    Wayne & Christine Floyd RE/MAX Realty Group

    41888 Jenkins Ct, Leonardtown, MD 20650
  • /4

    $749,900

    Coming Soon
    • 5 Beds
    • 4 Baths
    • 4,873 Sq Ft

    41402 Omaha Ct, Leonardtown, MD 20650

    2.25% Assumable VA loan & one of the largest lots in Leonard's Grant at .64 acres! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the

    Jonathan Powell Real Broker, LLC

    41402 Omaha Ct, Leonardtown, MD 20650
  • /70

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    41620 Church St, Leonardtown, MD 20650

    Fully renovated. Move-in ready. Prime downtown location.Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value.Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of

    Chanel Li Evergreen Properties

    41620 Church St, Leonardtown, MD 20650
  • /40

    $579,900

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    23636 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath colonial offers nearly 3,000 square feet of comfortable living space on a beautifully maintained 0.51-acre lot.Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • /41

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23679 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D2 Natural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Taj Quartz CountertopsSplendur Cream BacksplashDeluxe Shower in Primary

    Quality Built Homes Builder
    23679 Weeping Willow Way, Leonardtown, MD 20650
  • /6

    $125,000

    • Land
    • 3.42 Acres
    • $36,550 per Acre

    41180 Living Water Ln, Mechanicsville, MD 20659

    Set among the calm, rolling hills of Mechanicsville, Maryland, this 3.429-acre perced lot offers a rare blend of privacy, natural beauty, and readiness for development. Tucked into a peaceful wooded landscape, the property provides a blank canvas for building a single-family home in a setting that feels like a retreat. Property Highlights: Perced and Ready to Build: The lot has passed percolation

    Ralph Harvey ListWithFreedom.com

    41180 Living Water Ln, Mechanicsville, MD 20659
  • /30

    $1,750,000

    $115K PRICE INCREASE
    • 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
  • /3

    $155,000

    • Land
    • 19,166 Sq Ft
    • $352,273 per Acre

    41650 Miss Bessie Dr, Leonardtown, MD 20650

    Great building lot in the Leonardtown city limites with water and sewer available. Part of Singletree but no HOA dues. Currently staked for a house location. Property corners are not staked. See map in documents. Located across from the hospital, walking distance to down town.

    Jan Barnes CENTURY 21 New Millennium

    41650 Miss Bessie Dr, Leonardtown, MD 20650
  • /44

    $564,900

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,632 Sq Ft

    44294 Plantation Ct, California, MD 20619

    Welcome home to the perfect blend of timeless elegance, modern updates, and peaceful country living. Situated on a picturesque 1-acre lot in California, Maryland, this beautifully maintained 5-bedroom home offers the space, comfort, and privacy you've been searching for.Step inside to a bright, welcoming foyer that opens to a thoughtfully designed floor plan ideal for both everyday living and

    Chris Hill CENTURY 21 New Millennium

    44294 Plantation Ct, California, MD 20619
  • /33

    $629,900

    New Construction Open Thu 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42084 Wildflower Dr, Leonardtown, MD 20650

    To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start.This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an

    Laura Lee Hefley RE/MAX One

    42084 Wildflower 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
  • /16

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    18800 McKays Beach Rd, Leonardtown, MD 20650

    This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one

    Chris Coughlan RE/MAX One

    18800 McKays Beach Rd, Leonardtown, MD 20650
  • /6

    $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
  • /36

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23714 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSavannah Wicker Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe

    Quality Built Homes Builder
    23714 Weeping Willow Way, Leonardtown, MD 20650
  • /2

    $600,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 3,793 Sq Ft

    41524 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality.The thoughtful layout

    Billy Rabbitt The Southside Group Real Estate

    41524 Fairwood Ct, Leonardtown, MD 20650
  • /56

    $390,000

    • 5 Beds
    • 3 Baths
    • 1,080 Sq Ft

    23750 Hollywood Rd, Leonardtown, MD 20650

    Located on a private lot in Leonardtown, this 5 bedroom 3 full bathroom house has been updated and is ready for a new owner! Move right in and make it your own home. The upper level features an open kitchen with breakfast bar, formal dining & living rooms. There are 3 bedrooms and a full bathroom in the hallway. The primary bedroom has it's own bathroom. The lower level has 2 additional bedrooms

    Kelly Padgett Century 21 Redwood Realty

    23750 Hollywood Rd, Leonardtown, MD 20650
  • /45

    $619,900

    New Construction Open Thu 11:30AM - 3:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,976 Sq Ft

    42096 Wildflower Dr, Leonardtown, MD 20650

    Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space.This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level

    Laura Lee Hefley RE/MAX One

    42096 Wildflower Dr, Leonardtown, MD 20650
  • /22

    $420,000

    • 4 Beds
    • 2 Baths
    • 2,104 Sq Ft

    41012 Oakville Rd, Mechanicsville, MD 20659

    Must-See Turn-Key Home on a Private 1-Acre Lot Backing to Trees!Welcome home to this beautifully maintained, turn-key 4-bedroom, 2-bathroom home offering approximately 2,100 square feet of comfortable living space. Situated on a private 1-acre lot backing to mature trees, this home offers plenty of space both inside and out.The inviting interior features a spacious and functional layout

    Kristy Matthai-Dosberg CENTURY 21 New Millennium

    41012 Oakville Rd, Mechanicsville, MD 20659
  • /13

    $399,000

    • Land
    • 10,890 Sq Ft
    • $1,596,000 per Acre

    Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650

    Build your dream home in one of Leonardtown's most desirable locations! Welcome to Parcel 323, Tract 2, a newly created homesite just moments from the heart of historic downtown Leonardtown. Perfectly positioned to take advantage of beautiful water views of Breton Bay, this exceptional parcel offers the opportunity to enjoy the best of small-town coastal living. Imagine strolling to Leonardtown's

    Charlotte Long EXP Realty, LLC

    Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650
  • /10

    $299,000

    • Land
    • 5.8 Acres
    • $51,552 per Acre

    21365 Bogies Ln, Leonardtown, MD 20650

    Looking for land to build your dream home....well wait no more! This 5.8 acre parcel has been perc tested, recorded, surveyed and even has builder specs for a future home site and floor plans. You can also pick your own builder and get construction started on your new home. Property is currently registered and enrolled in an Agricultural program. Close to schools, shopping and area amenities.

    Kelly Padgett Century 21 Redwood Realty

    21365 Bogies Ln, Leonardtown, MD 20650
  • /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
  • /36

    $419,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft

    23898 Speith Rd, Leonardtown, MD 20650

    PRICE ENHANCEMENT! Step into this ONE level, completely renovated home that was stripped down to the studs and everything was replaced from the roof to the floor, new well, and connected to public sewer in 2022. Expand without having to worry about where the septic or septic reserve area is. See and feel the craftsmanship that was put in with wood flooring, stainless appliances, sought after barn

    Jimmy Hayden RE/MAX One

    23898 Speith Rd, Leonardtown, MD 20650
  • /4

    $169,900

    • Land
    • 2.82 Acres
    • $60,248 per Acre

    42262 Broyhill Ln, Hollywood, MD 20636

    VERY Nice Lot - Ready for you to build your dream home. Lot has been perced and ready for you. Buyer responsible for verifying and checking all information on the lot. Do Not Wait.

    Donna Lacey CENTURY 21 New Millennium

    42262 Broyhill Ln, Hollywood, MD 20636
  • /140

    $15,000,000

    Open Sat 1PM - 3PM
    • 6 Beds
    • 4.5 Baths
    • 5,500 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    OPEN HOUSES BY APPOINTMENT. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED!Mulberry Fields is one of those rare places where the land itself tells the story. The mile-long cedar avenue announces the approach, its rows planted at an ever-widening angle to draw the eye toward the Potomac below, a feat of 18th-century landscape design

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • /77

    $619,900

    • 4 Beds
    • 3.5 Baths
    • 3,940 Sq Ft

    43618 Albatross St, Hollywood, MD 20636

    Welcome to 43618 Albatross Street in the desirable Broad Creek community of Hollywood, MD! This beautifully appointed 4 bedroom, 3.5 bath home offers the perfect combination of spacious living, modern finishes, and a private backyard setting. The main level features a welcoming floor plan with a formal sitting room, a separate formal dining room, and a spacious family room with a cozy gas

    Erika Yowell EXP Realty, LLC

    43618 Albatross St, Hollywood, MD 20636
  • /25

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,218 Sq Ft

    42163 Blacksmith Shop Rd, Leonardtown, MD 20650

    Welcome Home! This charming rambler offers approximately 1,200 square feet of comfortable one-level living situated on a level 0.60-acre lot. A covered front porch provides a welcoming entry, while inside, the home has a practical floor plan with new flooring throughout and new kitchen appliances. Outside, enjoy the deck for relaxing or entertaining. With no HOA, you’ll appreciate the added

    Wanda White CENTURY 21 New Millennium

    42163 Blacksmith Shop Rd, Leonardtown, MD 20650
  • /2

    $714,900

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 4,744 Sq Ft

    23760 Coventry Dr, Leonardtown, MD 20650

    Welcome home to the Hampton model, featuring fresh paint, newer flooring, and updated carpet throughout! The main level showcases a welcoming two-story foyer and a soaring two-story family room flooded with natural light, along with dedicated formal living and dining room, a private study, and a chef-inspired grand kitchen with an expansive center island. Upstairs, you’ll find four spacious

    Tracey Summers CENTURY 21 New Millennium

    23760 Coventry Dr, Leonardtown, MD 20650

Showing Results 41 - 80, Page 2 of 3

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