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Newest Homes for Sale in Leonardtown, MD

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  • /90

    $715,000

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and effortless entertaining. Inside, stunning Tigerwood floors flow throughout much of

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • /77

    $524,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    NEW PRICE — $524,900! If you’ve been waiting for the right opportunity to make your move to Breton Bay, this could be the one.There’s something special about living in Breton Bay. It’s the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /45

    $619,900

    New Construction Open Sat 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
  • /85

    $619,500

    $60K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    NEW PRICE!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious office

    John Kreamer Taylor Properties

    23636 Hansel Ct, 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
  • /33

    $629,900

    New Construction Open Sat 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
  • /72

    $609,900

    New Construction Open Sat 11:30AM - 3:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,701 Sq Ft

    42102 Wildflower Dr, Leonardtown, MD 20650

    New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow.The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s

    Laura Lee Hefley RE/MAX One

    42102 Wildflower Dr, Leonardtown, MD 20650
  • /31

    $614,900

    New Construction Open Sat 11:30AM - 3:30PM
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42108 Wildflower Dr, Leonardtown, MD 20650

    New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing.The Fenwick offers a smart, comfortable layout with a spacious

    Laura Lee Hefley RE/MAX One

    42108 Wildflower Dr, Leonardtown, MD 20650
  • /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
  • /38

    $419,000

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

    23898 Speith Rd, Leonardtown, MD 20650

    New millings covered road!! 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

    Jimmy Hayden RE/MAX One

    23898 Speith Rd, Leonardtown, MD 20650
  • /74

    $649,000

    $21K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • /89

    $1,590,000

    $110K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,993 Sq Ft

    40115 Combs Creek Way, Leonardtown, MD 20650

    Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year.Perfectly positioned to capture breathtaking water views, this exceptional property offers a

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650
  • /17

    $288,900

    • Land
    • 23.44 Acres
    • $12,325 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or

    Brooke Matthews RE/MAX One

    0 Whirlwind Rd, Leonardtown, MD 20650
  • /40

    $559,900

    $40K 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 living space on a beautifully maintained 0.51-acre lot, combining comfortable everyday living with plenty of room to grow.Step inside to a bright, inviting interior featuring new carpet and luxury vinyl plank flooring, giving the home a fresh, move-in-ready feel.

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • /56

    $749,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,097 Sq Ft

    22393 Saint Clements Ave, Leonardtown, MD 20650

    Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the breathtaking water views, this light-filled home features an open-concept floor plan that seamlessly blends comfortable everyday living with exceptional entertaining space.Offering 4 bedrooms, 2 full baths, and 2 half baths, the home has been extensively

    Alyson Anderson Allfirst Realty, Inc.

    22393 Saint Clements Ave, Leonardtown, MD 20650
  • /2

    $290,000

    $10K PRICE DROP
    • Land
    • 15 Acres
    • $19,333 per Acre

    42700 Moll Dyer Rd, Leonardtown, MD 20650

    Discover a prime 15-acre parcel of land, offering a unique investment opportunity with significant potential returns. This property features a serene backdrop of trees and wooded areas, providing a tranquil setting while ensuring privacy. The sloping terrain enhances the natural beauty and could be ideal for various development projects, from residential homes to recreational retreats. The wooded

    Paul Fenton Coldwell Banker Premier

    42700 Moll Dyer Rd, Leonardtown, MD 20650
  • /13

    $454,900

    New Construction Open Sat 11:30AM - 3:30PM
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    **** December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting!Homesite 157 Madison D1: 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

    Laura Lee Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • /9

    $454,900

    New Construction Open Sat 11:15AM - 3:30PM $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

    ****December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! *****Homesite #156 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space. This interior unit

    Laura Lee Hefley RE/MAX One

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
  • /67

    $799,900

    • Land
    • 3.56 Acres
    • $224,691 per Acre

    39645 Sweetpea Ln, Leonardtown, MD 20650

    UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless

    Sandi Denny CENTURY 21 New Millennium

    39645 Sweetpea Ln, Leonardtown, MD 20650
  • /21

    $449,900

    New Construction Open Sat 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ALMOST READY***Estimated Late October Delivery****Under Construction***Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or

    Laura Lee Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, 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
  • /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
  • /70

    $389,000

    $10K PRICE DROP
    • 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
  • /35

    $840,000

    • Land
    • 10.2 Acres
    • $82,353 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat.With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • /33

    $450,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage 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 crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    20798 Waterside Dr, Leonardtown, MD 20650
  • /6

    $175,000

    • Land
    • 6.24 Acres
    • $28,045 per Acre

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650

    6+ acre lot zoned RPD in a prime location with approximately 600 ft of road frontage and high visibility potential. This is NOT currently a residential building lot because it failed a perc test in April 2005. However, the current Comprehensive Zoning Ordinance lists other “potential” uses that may not require on-site sewage disposal. The list includes but is not limited to: Construction

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    0 St Andrews Church Rd Unit MDSM2029070, 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
  • /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
  • /10

    $190,000

    • Land
    • 5 Acres
    • $38,000 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

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • /140

    $15,000,000

    • 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
  • /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

Showing Results 41 - 71, Page 2 of 2

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