24

Hollywood, MD Homes for Sale with Acreage

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  • 23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    /31

    $439,900

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,634 Sq Ft

    23801 Mcintosh Rd, Hollywood, MD 20636

    BIG PRICE IMPROVEMENT – Now Offered at $439,900. Pool is open and ready for summer. Welcome to this well-maintained split foyer home situated on a 1.25-acre lot in Hollywood, MD, offering the perfect blend of space, comfort, and convenience. Located in the sought-after Leonardtown school district—Duke Elementary, Leonardtown Middle, and Leonardtown High School—this home offers NO HOA and no

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    23801 Mcintosh Rd, Hollywood, MD 20636
  • 42625 Richly Ln, Hollywood, MD 20636
    42625 Richly Ln, Hollywood, MD 20636
    42625 Richly Ln, Hollywood, MD 20636
    /50

    $900,000

    $50K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,179 Sq Ft

    42625 Richly Ln, Hollywood, MD 20636

    PRICE REDUCED!!! Welcome to refined living in this exceptional QBHI Fairfax model, perfectly situated on nearly two private acres and just 16 months young. Located in the highly sought-after Broyhill community of Leonardtown, this beautifully crafted home blends luxury, comfort, and thoughtful design at every turn. From the moment you arrive, you’ll appreciate the expansive, mostly flat

    Dorothy Bistransin Redfin Corp

    42625 Richly Ln, Hollywood, MD 20636
  • 00 Saint Andrews Church Rd, Leonardtown, MD 20650
    00 Saint Andrews Church Rd, Leonardtown, MD 20650
    00 Saint Andrews Church Rd, 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
  • 0 Cottonwood Pkwy, Wildewood, MD 20619
    0 Cottonwood Pkwy, Wildewood, 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
  • 24715 Half Pone Point Rd, Hollywood, MD 20636
    24715 Half Pone Point Rd, Hollywood, MD 20636
    24715 Half Pone Point Rd, Hollywood, MD 20636
    /17

    $1,450,000

    Coming Soon
    • 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
  • 22755 Deerhaven Ln, California, MD 20619
    22755 Deerhaven Ln, California, MD 20619
    22755 Deerhaven Ln, California, MD 20619
    /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
  • 0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, 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
  • 43979 Drum Cliff Rd, Hollywood, MD 20636
    43979 Drum Cliff Rd, Hollywood, MD 20636
    43979 Drum Cliff Rd, Hollywood, MD 20636
    /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
  • 24040 Hollywood Rd, Hollywood, MD 20636
    24040 Hollywood Rd, Hollywood, MD 20636
    24040 Hollywood Rd, Hollywood, MD 20636
    /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
  • 0 Saint Johns Rd, Hollywood, MD 20636
    0 Saint Johns Rd, Hollywood, MD 20636
    0 Saint Johns Rd, Hollywood, MD 20636
    /8

    $200,000

    $50K PRICE DROP
    • 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
  • 24301 Old Hollywood Rd, Hollywood, MD 20636
    24301 Old Hollywood Rd, Hollywood, MD 20636
    24301 Old Hollywood Rd, Hollywood, MD 20636
    /6

    $515,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,365 Sq Ft

    24301 Old Hollywood Rd, Hollywood, MD 20636

    One owner for almost 60 years! Home recently had new roof, new windows, new doors, and appliances. If you desire no subdivision, 1+ acres, detached garage/workshop, extra outside storage, secluded area, centrally located, and ONE level, this may be what you're looking for. Unfinished walk up/out basement centrally located in Hollywood close to park. Close to downtown Leonardtown, hospital,

    Jimmy Hayden RE/MAX One

    24301 Old Hollywood Rd, Hollywood, MD 20636
  • 24249 Mcintosh Rd, Hollywood, MD 20636
    24249 Mcintosh Rd, Hollywood, MD 20636
    24249 Mcintosh Rd, Hollywood, MD 20636
    /65

    $950,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 2,934 Sq Ft

    24249 Mcintosh Rd, Hollywood, MD 20636

    Rare opportunity to own a breathtaking Horse Farm that features an exquisite custom farmhouse on 21.95 breathtaking acres just 2 miles from downtown Leonardtown! This unbelievable location offers the perfect balance of privacy and convenience with easy access to schools, shopping, restaurants, coffee shops, and commuter routes while enjoying the peace and tranquility of country living. The

    Mary Chambers JPAR Real Estate Professionals

    24249 Mcintosh Rd, Hollywood, MD 20636
  • 0 Cottonwood Pkwy, Wildewood, MD 20619
    0 Cottonwood Pkwy, Wildewood, MD 20619
    /2

    $775,000

    • Land
    • 4.7 Acres
    • $164,894 per Acre

    0 Cottonwood Pkwy, Wildewood, MD 20619

    4.7 Commercial Acres in Wildewood Technology ParkOne of the last available lots!Rare opportunity to purchase 4.7 commercial acres in the highly desirable Wildewood Technology Park, positioned in the heart of St. Mary’s County’s future growth corridor.This property aligns with the County’s Innovative District Master Plan surrounding the airport, placing it at the forefront of future

    Jessica Raley CENTURY 21 New Millennium

    0 Cottonwood Pkwy, Wildewood, MD 20619
  • 45410 Clarks Mill Rd, Hollywood, MD 20636
    45410 Clarks Mill Rd, Hollywood, MD 20636
    45410 Clarks Mill Rd, Hollywood, MD 20636
    /4

    $799,000

    • Land
    • 1.69 Acres
    • $472,781 per Acre

    45410 Clarks Mill Rd, Hollywood, MD 20636

    Discover an unparalleled opportunity to own a stunning 1.69-acre parcel of land nestled along the serene banks of Hickory Landing Creek. This exclusive waterfront property boasts an impressive 400 feet of pristine water frontage, offering breathtaking panoramic views that will captivate your senses and inspire your imagination. Imagine waking up to the gentle sounds of nature, with the shimmering

    Steve Lowe United Real Estate Premier

    45410 Clarks Mill Rd, Hollywood, MD 20636
  • 41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, Leonardtown, MD 20650
    41708 Fenwick St, 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
  • 20265 Hawks Way, Leonardtown, MD 20650
    20265 Hawks Way, 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
  • 24699 Hollywood Rd, Hollywood, MD 20636
    24699 Hollywood Rd, Hollywood, MD 20636
    24699 Hollywood Rd, Hollywood, MD 20636
    /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
  • 0 Ewell Ln, Hollywood, MD 20636
    0 Ewell Ln, Hollywood, MD 20636
    0 Ewell Ln, Hollywood, MD 20636
    /10

    $175,000

    • Land
    • 3.16 Acres
    • $55,380 per Acre

    0 Ewell Ln, Hollywood, MD 20636

    Tucked along the peaceful, navigable waters of Cuckold Creek, this waterfront lot ready to build offers the perfect blend of privacy and possibility! With a recent perc approval (April 2025), it’s ready for your dream home plans! Community pier borders the lot and a perfect spot for fishing, kayaking, or just enjoying the views. Neighboring homes feature piers—buyer to verify any desired water

    Cheryl Bare CENTURY 21 New Millennium

    0 Ewell Ln, Hollywood, MD 20636
  • 26350 Three Notch Rd, Mechanicsville, MD 20659
    26350 Three Notch Rd, Mechanicsville, MD 20659
    26350 Three Notch Rd, Mechanicsville, MD 20659
    /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
  • 24730 Half Pone Point Rd, Hollywood, MD 20636
    24730 Half Pone Point Rd, Hollywood, MD 20636
    24730 Half Pone Point Rd, Hollywood, MD 20636
    /40

    $4,595,000

    Coming Soon
    • 4 Beds
    • 7 Baths
    • 13,665 Sq Ft

    24730 Half Pone Point Rd, Hollywood, MD 20636

    A legacy waterfront estate at the tip of coveted Half Pone Point.Commanding one of the most prestigious waterfront settings in Southern Maryland, this extraordinary residence offers more than 14,000 square feet of meticulously crafted living space designed to capture breathtaking panoramic views of the Patuxent River from nearly every room. Architectural excellence and exceptional

    Christopher Carr HomeZu

    24730 Half Pone Point Rd, Hollywood, MD 20636
  • 25675 Southwell Ln, Hollywood, MD 20636
    25675 Southwell Ln, Hollywood, MD 20636
    25675 Southwell Ln, Hollywood, MD 20636
    /6

    $115,000

    $10K PRICE DROP
    • Land
    • 2.17 Acres
    • $52,995 per Acre

    25675 Southwell Ln, Hollywood, MD 20636

    Located in Saint Mary's county, where you will find lots of rolling hills and land. This 2.17 acre lot offered in the Sotterley Manor neighborhood could be just what you are looking for. Although it has it's bumps and bruises it offers the seclusion you desire the most. If you are looking to build a private oasis within a neighborhood of estate homes, this would be the spot to do so. Not far from

    Alicia Richardson AMR Elite Realtors, LLC

    25675 Southwell Ln, Hollywood, MD 20636
  • 0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    /37

    $93,500

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

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    ucked 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, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 44405 5 LOTS K & R Way, Hollywood, MD 20636
    44405 5 LOTS K & R Way, Hollywood, MD 20636
    /2

    $1,300,000

    $12M PRICE DROP
    • Land
    • 3.69 Acres
    • $352,304 per Acre

    44405 5 LOTS K & R Way, Hollywood, MD 20636

    Come join the BOOMING townhouse market in Southern Maryland with this prime parcel:3.69 acre parcel 1.6 miles from the St. Mary’s Regional Airport and Technology Park, 10miles from Patuxent River Naval Air Station/NAWCAD, less than one hour to DC/NorthernVirginia.The Villages at Clarks MillThe property currently has a Concept Plan for 18 townhome units approved by the

    Cathy Rose Samson Properties

    44405 5 LOTS K & R Way, Hollywood, MD 20636
  • 24984 Forrest Cove Way, Hollywood, MD 20636
    24984 Forrest Cove Way, Hollywood, MD 20636
    24984 Forrest Cove Way, Hollywood, MD 20636
    /10

    $185,000

    • 3 Beds
    • 2 Baths
    • 2,080 Sq Ft

    24984 Forrest Cove Way, Hollywood, MD 20636

    3 bedroom 2 bath detached single family home situated on a beautiful private lot (1.49 acre). HUD MAKES NO REPAIRS. HUD CASE#241-765957).Insurability: UNINSURABLE DUE TO CONDITION All bids to be submitted at: www.hudhomestore.gov. Bids may only be submittedby HUD registered Agents/Agencies. All properties built before 1978 will include a LBP. Agents can obtain copies of any disclosures at:

    Christopher White Classic Select Inc

    24984 Forrest Cove Way, Hollywood, MD 20636
Maryland St Marys County Hollywood

Homes for Sale with Acreage in Hollywood, MD

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In Hollywood, there are currently 24 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Hollywood, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Hollywood and discover the potential and freedom that comes with owning your own piece of property.

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