163

Homes for Sale near Leonardtown High School

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  • /49

    $517,900

    Open Sat 12PM - 3PM $22K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,003 Sq Ft

    23302 Misty Pond Ln, California, MD 20619

    Back with an amazing upgraded kitchen. Pics coming. Kitchen received a new deep sink and faucet, beautiful modern white stone counters and the cabinets were painted with new hardware and new soft close hinges. Amazing colonial in quiet cul-da-sac. Home has a new roof in 2022 with the transferable warranty. Basement is finished fully in 2026, new paint in foyer and upstairs hall, new SHUTTERS and

    Agent Photo

    James Dick

    Long & Foster Real Estate, Inc.

    23302 Misty Pond Ln, California, MD 20619
  • /31

    $499,000

    • 5 Beds
    • 3.5 Baths
    • 3,257 Sq Ft

    44905 Widgeon Place, Callaway, MD 20620

    Welcome home to this well-maintained, beautifully landscaped property offering the perfect blend of convenience, comfort, and functionality! Ideally located just minutes from shopping, dining, and Patuxent River Naval Air Station (PAX NAS), this home makes daily commuting and errands a breeze. Inside, you'll find a spacious floor plan featuring a large primary suite with a private ensuite

    Agent Photo

    Amy Scott

    OE Realty

    44905 Widgeon Place, Callaway, MD 20620
  • /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
  • /22

    $179,000

    $16K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    16448 Ball Point Rd, Piney Point, MD 20674

    Have you always wanted a weekend retreat in a neighborhood surrounded by water? You might not have ever been to St Georges Island but you will be in for a treat! Community park, picnic area and boat ramps within about a mile of the property. Great for fishing, crabbing, boating and outdoor events. Water views from your back yard are already yours. Peaceful and quiet neighborhood, you will

    Agent Photo

    Gail Nyman

    RE/MAX United Real Estate

    16448 Ball Point Rd, Piney Point, MD 20674
  • /32

    $369,900

    $17K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    43569 Marguerite Way, California, MD 20619

    Beautiful end-unit townhome showcasing exceptional care and attention to detail throughout. Tastefully decorated and move-in ready, this home is waiting for your personal touch. The spacious kitchen features granite countertops, abundant workspace, and plenty of room for entertaining. Overlooking a huge family room, the layout embodies today's sought after open concept design. Step directly from

    Agent Photo

    Trish Brow

    O'Brien Realty ERA Powered

    43569 Marguerite Way, California, MD 20619
  • /10

    $799,000

    • 5 Beds
    • 3 Baths
    • 2,727 Sq Ft

    44908 Hickory Landing Way, Hollywood, MD 20636

    Welcome to Hickory Landing Waterfront property. The tree-filled private and quiet 17+ acre property is located on a cove off of Cuckold Creek. Experience breathtaking views from both the living room and the upper level, offering a perfect backdrop for daily living and relaxation. Chef's kitchen features custom solid maple painted cabinets, providing timeless elegance and ample storage space for

    Agent Photo

    Barbara Raley

    Berkshire Hathaway HomeServices PenFed Realty

    44908 Hickory Landing Way, Hollywood, MD 20636
  • /19

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***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 4th bedroom with a

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • /36

    $93,500

    • Land
    • 4.11 Acres
    • $22,749 per Acre

    00 Saint Andrews Church Rd, Leonardtown, MD 20650

    Tucked away in Leonardtown in St. Mary's County, this 4.11 acre wooded parcel on St. Andrews Church Road is a rare chance to build, invest, or settle into your own recreational retreat. The property already has a previous perc site in place for a conventional septic system. Soil stability testing will be required, but preliminary work points to favorable conditions. Buyers are encouraged to

    Casey Kennedy Whitetail Properties Real Estate

    00 Saint Andrews Church Rd, Leonardtown, MD 20650
  • /15

    $29,900

    • Land
    • 11,761 Sq Ft
    • $110,741 per Acre

    0 Third St, Piney Point, MD 20690

    Looking for the perfect spot to build your future dream home? This 0.27-acre (12,000 sq. ft.) lot in Tall Timbers, MD offers an excellent buy-and-hold opportunity while awaiting potential sewer availability. With the major OAG project bringing jobs to the area and the Lighthouse development underway nearby, sewer service may be coming sooner rather than later—potentially increasing property

    Krista Depenthal Lands2Love

    0 Third St, Piney Point, MD 20690
  • /61

    $299,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    Nassau Cove Plan at Wildewood Village 55+, California, MD 20619

    The Nassau Cove lives beautifully, starting with effortless entry from your one-car garage into a stunning gourmet kitchen. A spacious center island anchors the open great room and dining area—ideal for everyday living or entertaining.Gather indoors or extend the celebration outside on the optional patio. Enjoy the ease of a main-level Owner’s Suite with a dual-vanity bath and oversized walk-in

    Ryan Homes Builder
    23058 Wetstone Ln Unit 36143064, California, MD 20619
  • /2

    $16,000,000

    $6M PRICE INCREASE
    • Land
    • 141.46 Acres
    • $113,106 per Acre

    0 Cottonwood Pkwy, Wildewood, MD 20619

    Rare opportunity to acquire a premier large-scale assemblage within the highly sought-after Wildewood Technology Park and surrounding growth corridor.This offering includes: * 113.42 acres of commercially zoned land within Wildewood Technology Park* 28.038 acres of industrially zoned land along Three Notch Road / Airport RoadTotaling an impressive 141.458 acres of strategic

    Jessica Raley CENTURY 21 New Millennium

    0 Cottonwood Pkwy, Wildewood, MD 20619
  • /7

    $244,998

    $55K PRICE DROP
    • Land
    • 3.36 Acres
    • $72,916 per Acre

    16252 Thomas Rd, Piney Point, MD 20674

    Major Price Improvement- Highly motivated Seller. Bring your best reasonable offer and seize this opportunity.Rare buildable waterfront lot in sought-after Piney Point, Maryland. Located at 16252 Thomas Road, this expansive approximately 3.3-acre parcel offers approximately 348 feet of direct water frontage along a tidal creek, providing a serene setting and excellent potential for a custom

    Payam Bakhaje Realty ONE Group Capital

    16252 Thomas Rd, Piney Point, MD 20674
  • /16

    $334,000

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,274 Sq Ft

    25263 Sotterley Rd, Hollywood, MD 20636

    Welcome to this beautifully renovated home in the heart of Hollywood! Completely updated in 2024, this move-in ready property blends modern finishes with timeless charm and offers the perfect mix of comfort, style, and convenience. From the moment you arrive, you’ll appreciate the fresh exterior appeal and thoughtfully redesigned interior spaces.Inside, the home features a bright and open

    Christopher Carr HomeZu

    25263 Sotterley Rd, Hollywood, MD 20636
  • /67

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 5,939 Sq Ft

    20098 Piney Point Rd, Callaway, MD 20620

    Want to live near your business?! This beautiful and classic 3 bedroom, 2 and half bathroom rancher has well-maintained curb appeal and the interior to match, beginning with the flower bed enriched porch. From the front door you are greeted with a spacious living room great for relaxing and enjoying the view from the large picturesque windows. This area also includes a separate kitchen/dining

    Shanita Kelley Samson Properties

    20098 Piney Point Rd, Callaway, MD 20620
  • /17

    $1,450,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    24715 Half Pone Point Rd, Hollywood, MD 20636

    A rare opportunity to own an extraordinary 11.83-acre wooded property in the prestigious Half Pone Point community. Located directly across from the spectacular waterfront estate at 24730 Half Pone Point Rd, this versatile property offers endless possibilities for a private family compound, car collector, hobbyist, business owner, or recreational enthusiast.The property is improved with five

    Christopher Carr HomeZu

    24715 Half Pone Point Rd, Hollywood, MD 20636
  • /33

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    22755 Deerhaven Ln, California, MD 20619

    Rare opportunity to enjoy the perfect blend of country living and everyday convenience! Nestled on 3 private acres in California, Maryland, this charming farmette is just minutes from schools, shopping, restaurants, and PAX Naval Air Station, yet offers the peaceful setting you've been dreaming of. The 1,824 sq ft rambler features 3 bedrooms, 2 full baths, and a spacious floor plan designed for

    Mary Chambers JPAR Real Estate Professionals

    22755 Deerhaven Ln, California, MD 20619
  • /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
  • /12

    $454,900

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

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected 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

    Laura Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • /85

    $629,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    CREDIT FOR REPAIRS!! New Lower 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

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • /58

    $499,900

    • 2 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 2BR 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
  • /56

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    43927 Lanedon Dr, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY MONDAY AUGUST 10th at 10:00 AMOwned by the same family since the 1960s, this 3-bedroom, 2-bath rambler has been lovingly maintained and is ready for its next chapter. This one already has the space, setting, and major improvements to make the possibilities exciting. The larger updates have already been taken care of, including a newer roof, siding, windows, new

    Sarah Mulford-Martin EXP Realty, LLC

    43927 Lanedon Dr, Leonardtown, MD 20650
  • /75

    $1,099,900

    New Construction $300K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    16242 Thomas Rd, Piney Point, MD 20674

    PRICE IMPROVEMENT! Experience an exceptional waterfront lifestyle in this newly constructed custom home, thoughtfully designed with luxury, comfort, and breathtaking water views in mind. Situated on over 2 private acres with approximately 340 feet of waterfront, this one-of-a-kind residence offers a rare opportunity to own a truly distinctive property in Southern Maryland. Inside, you’ll find

    Payam Bakhaje Realty ONE Group Capital

    16242 Thomas Rd, Piney Point, MD 20674
  • /43

    $649,900

    Open House 8/16 $99K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,440 Sq Ft

    16104 Piney Point Rd, Piney Point, MD 20674

    Welcome to your waterfront escape on the point of St. George Island, where the Potomac River meets the Chesapeake Bay.This home was built by the local Amish community for this family. This rare offering features 154 feet of riprapped shoreline, delivering sweeping water views and front-row seats to breathtaking sunrises, passing boats, and endless coastal serenity.The main home offers 4

    Debbie Buckingham Samson Properties

    16104 Piney Point Rd, Piney Point, MD 20674
  • /7

    $79,900

    • Land
    • 3.57 Acres
    • $22,381 per Acre

    18832 Piney Point Rd, Valley Lee, MD 20692

    Welcome to 18832 Piney Point Road! This property spans 3.57 acres and includes two lots within one parcel. Build your dream home in the peaceful waterfront community of Piney Point, Maryland. This exceptional parcel offers a rare opportunity to create a custom residence surrounded by natural beauty, privacy, and coastal charm. Nestled near the Potomac River, the property provides a serene setting

    Jonathan Benya EXP Realty, LLC

    18832 Piney Point Rd, Valley Lee, MD 20692
  • /43

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 2,748 Sq Ft

    43410 Old Wharf Ln, Hollywood, MD 20636

    Nestled along the shores of the Patuxent River is this very private, custom-built, all brick home with beautiful hardwood floors throughout, modern kitchen and baths situated on 5 sprawling acres. Riprapped shoreline, professionally landscaped yard, 4 stall horse barn, dog run and more. Enjoy nature's beauty on the water; conveniently located for a D.C. commute. A great get-away for enjoying

    Barbara Stellway KW Metro Center

    43410 Old Wharf Ln, Hollywood, MD 20636
  • /80

    $1,749,000

    • 3 Beds
    • 4 Baths
    • 4,537 Sq Ft

    24814 Half Pone Point Rd, Hollywood, MD 20636

    Welcome to this stunning custom waterfront home, situated high on Half Pone Point, offering elegant living on the St. Mary’s side of the Patuxent River. Built in 2014, this well-maintained property features quality workmanship throughout its approximately 4,500 square feet of above-grade living space. The bright and open interior features a first-floor owner's suite, spacious secondary bedrooms

    Brooke Matthews RE/MAX One

    24814 Half Pone Point Rd, Hollywood, MD 20636
  • /16

    $149,900

    • Land
    • 35,283 Sq Ft
    • $185,062 per Acre

    45025 Nolan Ct, Hollywood, MD 20636

    The lot is located in a well-established, sought-after area of Hollywood, a quiet, secluded, wooded lot. walking distance to Greenwell State Park.Great for the person who likes to walk and jog. Across from a currently farmed field. Conveniently located near the County's Forrest Landing boat ramp to Cuckel Creek, launch your boat or kayaks There is an approved perk for the site.Approximately

    Daniel Rebarchick Franzen Realtors, Inc.

    45025 Nolan Ct, Hollywood, MD 20636
  • /19

    $699,900

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

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • /9

    $399,000

    $181K PRICE DROP
    • 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
  • /2

    $525,000

    Coming Soon
    • 3 Beds
    • 3.5 Baths
    • 2,314 Sq Ft

    22931 Snow Leopard Dr, California, MD 20619

    This well maintained two story with basement is just waiting for that new family. Three bedrooms, 3 1/2 baths, fenced back yard for the family dog, stone patio off deck, two car garage, main level family room with gas fireplace, eat at counter in the kitchen as well as room for a breakfast table and a large seperate dining room. A rocking chair front porch for relaxed evenings, rec room in

    Jan Barnes CENTURY 21 New Millennium

    22931 Snow Leopard Dr, California, MD 20619
  • /29

    $359,777

    • 4 Beds
    • 2 Baths
    • 2,474 Sq Ft

    40743 Magee Dr, Leonardtown, MD 20650

    Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished

    Liam Coonahan Real of Pennsylvania

    40743 Magee Dr, Leonardtown, MD 20650
  • /5

    $335,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    24040 Hollywood Rd, Hollywood, MD 20636

    3BR / 1B Rambler on an acre of land w/garage (storage), Detached carport and outbuildings. Paved driveway just off Hollywood/Leonardtown Road. Hardwood floors throughout Living Room, Hall and bedrooms. Level rear yard bordered by trees. Oil Furnace, water heater, utility sink and washer hook-up are located in the (walk-in) storage area under the home.

    Sheila Milburn Coldwell Banker Premier

    24040 Hollywood Rd, Hollywood, MD 20636
  • /3

    $625,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    20980 Aster Dr, Callaway, MD 20620

    Welcome to 20890 Aster Drive, where privacy, efficiency, and timeless charm come together on more than 4 peaceful acres in the heart of Callaway. This inviting Cape Cod offers the freedom of country living with no HOA, while providing exceptional value through major system upgrades that make homeownership both comfortable and economical. Step inside to discover a light-filled family room with

    Charlotte Long EXP Realty, LLC

    20980 Aster Dr, Callaway, MD 20620
  • /24

    $599,900

    Open House 8/16
    • 3 Beds
    • 1 Bath
    • 828 Sq Ft

    16101 Piney Point Rd, Piney Point, MD 20674

    Some properties are purchased for the house. Others are purchased for the place. Set on a narrow finger of land between two bodies of water, 16101 Piney Point Road offers an extraordinary waterfront setting with sunrise light on one side and spectacular sunset views on the other. The existing cottage provides an immediate place to enjoy life, watch the sky change, enjoy the water, and begin

    Michelle Camaioni RE/MAX One

    16101 Piney Point Rd, Piney Point, MD 20674
  • /77

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /64

    $700,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • /40

    $249,900

    Open Sun 11AM - 2PM
    • 2 Beds
    • 2.5 Baths
    • 1,588 Sq Ft

    20811 Harlequin Ln, Callaway, MD 20620

    Spacious Callaway townhome with plenty of room to make your own. The main level features an eat-in kitchen and a large living room that opens directly to the deck and private backyard. Upstairs, you’ll find two generously sized bedrooms, one with a private en suite bathroom and the other with direct access to a full hall bathroom. The finished lower level offers a versatile recreation room with

    Katy Galloway Century 21 Redwood Realty

    20811 Harlequin Ln, Callaway, MD 20620
  • /3

    $29,900

    • Land
    • 10,454 Sq Ft
    • $124,583 per Acre

    26457 Peninsular Dr, Hollywood, MD 20636

    Vacant parcel around 1/4 acre in size in Hollywood Shores. Call Listing Agent with questions. Photos to be posted soon.

    Gloria Abell Coldwell Banker Premier

    26457 Peninsular Dr, Hollywood, MD 20636

Showing Results 1 - 40, Page 1 of 5

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