26

Hollywood, MD Homes for Sale with Acreage

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  • 44015 Sandy Bottom Rd, Hollywood, MD 20636
    44015 Sandy Bottom Rd, Hollywood, MD 20636
    44015 Sandy Bottom Rd, Hollywood, MD 20636
    /35

    $475,000

    • 5 Beds
    • 3 Baths
    • 1,752 Sq Ft

    44015 Sandy Bottom Rd, Hollywood, MD 20636

    You want large? You want one level? You want some land? You want to be rural? You want to be close to everything? This probably checked most or all your boxes. Stainless appliances, granite counter tops, hardwood flooring, etc. to take it to the top of your list. OVersized 2 car garage too. 5 BR, 3 BA single family rambler in sought after Hollywood.

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 229-3043

    44015 Sandy Bottom Rd, Hollywood, MD 20636
  • 23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    /42

    $464,900

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3 Baths
    • 1,634 Sq Ft

    23801 Mcintosh Rd, Hollywood, MD 20636

    OPEN HOUSE SUNDAY 1PM-3PM. Leonardtown schools, NO HOA or Leonardtown taxes! 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 also provides easy access to

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 770-1422

    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

    $950,000

    Open Sat 1PM - 3PM
    • 6 Beds
    • 4.5 Baths
    • 5,179 Sq Ft

    42625 Richly Ln, Hollywood, MD 20636

    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 yard—ideal for outdoor

    Dorothy Bistransin Redfin Corp

    42625 Richly Ln, Hollywood, MD 20636
  • 43530 Drum Cliff Rd, Hollywood, MD 20636
    43530 Drum Cliff Rd, Hollywood, MD 20636
    43530 Drum Cliff Rd, Hollywood, MD 20636
    /21

    $550,000

    Open Sun 12PM - 2PM
    • 4 Beds
    • 2 Baths
    • 1,959 Sq Ft

    43530 Drum Cliff Rd, Hollywood, MD 20636

    Impeccably maintained, energy efficient, and located in a neighborhood of pristine, old-growth forest, this right-sized home is perfect for a young family or an older family with visiting guests. Drum Cliff is nestled between the headwaters of St Thomas Creek and the Patuxent River, and the neighborhood offers safe walking on its quiet, dead-end streets. Thoroughly updated in 2017 with a new

    Dorothy Bistransin Redfin Corp

    43530 Drum Cliff Rd, Hollywood, MD 20636
  • 000 Saint Andrews Church Rd, Leonardtown, MD 20650
    000 Saint Andrews Church Rd, Leonardtown, MD 20650
    000 Saint Andrews Church Rd, Leonardtown, MD 20650
    /36

    $98,900

    $6K PRICE DROP
    • Land
    • 4.11 Acres
    • $24,063 per Acre

    000 Saint Andrews Church Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!! Located in Leonardtown in St. Marys County, this 4.11 acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable

    Casey Kennedy Whitetail Properties Real Estate

    000 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 43063 Hugh Dr, Hollywood, MD 20636
    43063 Hugh Dr, Hollywood, MD 20636
    43063 Hugh Dr, Hollywood, MD 20636
    /32

    $693,000

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

    43063 Hugh Dr, Hollywood, MD 20636

    Nestled on 29.5 acres of serene, wooded privacy, this exceptional estate offers a rare blend of character, modern updates, and endless potential. Inside the 2,700+ sq ft home, you’re welcomed by distinctive features like a striking cedar beam and dual staircases that add warmth and architectural charm. The spacious kitchen is a standout, featuring granite countertops, stainless steel appliances,

    Billy Rabbitt The Southside Group Real Estate

    43063 Hugh Dr, Hollywood, MD 20636
  • 24065 Pappys Way, Hollywood, MD 20636
    24065 Pappys Way, Hollywood, MD 20636
    24065 Pappys Way, Hollywood, MD 20636
    /101

    $675,000

    • 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 Redwood Realty

    24065 Pappys Way, Hollywood, MD 20636
  • 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
  • 43075 Joy Ln, Hollywood, MD 20636
    43075 Joy Ln, Hollywood, MD 20636
    43075 Joy Ln, Hollywood, MD 20636
    /61

    $520,000

    • 3 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    43075 Joy Ln, Hollywood, MD 20636

    Welcome home to this spacious and well maintained 3-bedroom, 2.5-bath rambler with 2 car garage offering 2,488 sq ft of comfortable living space plus a private 1-bedroom, 1-bath in-law suite with separate entrance! This home features generous living spaces, a functional layout, and plenty of room to spread out both inside and out. Enjoy spacious bedrooms, multiple gathering areas, and the ease of

    Katherine Dean RE/MAX One

    43075 Joy Ln, Hollywood, MD 20636
  • 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

    $350,000

    • 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
  • 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
  • 26200 Locust Grove Farm Ln, Hollywood, MD 20636
    26200 Locust Grove Farm Ln, Hollywood, MD 20636
    26200 Locust Grove Farm Ln, Hollywood, MD 20636
    /5

    $1,300,000

    • Land
    • 413.57 Acres
    • $3,143 per Acre

    26200 Locust Grove Farm Ln, Hollywood, MD 20636

    Incredible 400 plus acres in North Hollywood; 2 parcels, water frontage on Cole Creek connecting to the Patuxent River. Property is subject to Conservation Easement.

    Barbara Stellway KW Metro Center

    26200 Locust Grove Farm Ln, Hollywood, MD 20636
  • 45410 Clarks Mill Rd, Hollywood, MD 20636
    45410 Clarks Mill Rd, Hollywood, MD 20636
    45410 Clarks Mill Rd, Hollywood, MD 20636
    /4

    $899,000

    • Land
    • 1.69 Acres
    • $531,953 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
    /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
  • 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
  • 0 Ewell Ln, Hollywood, MD 20636
    0 Ewell Ln, Hollywood, MD 20636
    0 Ewell Ln, Hollywood, MD 20636
    /10

    $200,000

    • Land
    • 3.16 Acres
    • $63,291 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
  • 43671 Sunny Ridge Ln, Hollywood, MD 20636
    43671 Sunny Ridge Ln, Hollywood, MD 20636
    43671 Sunny Ridge Ln, Hollywood, MD 20636
    /45

    $960,000

    $40K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,465 Sq Ft

    43671 Sunny Ridge Ln, Hollywood, MD 20636

    Set on nearly 14 acres along St. Thomas Creek in Hollywood, this fully renovated all-brick rambler offers a rare combination of space, thoughtful updates, and waterfront living. Inside, the home was completely remodeled in 2023, delivering a clean, refreshed interior designed for everyday comfort and easy entertaining. Just beyond the main living area, a new Trex deck spans the rear of the home,

    Caitlin Vallandingham Infinitas Realty Group

    43671 Sunny Ridge 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
    /34

    $98,900

    $6K PRICE DROP
    • Land
    • 4.11 Acres
    • $24,063 per Acre

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    Located in Leonardtown in St. Mary’s County, this 4.11± acre wooded property on St. Andrews Church Road offers a unique opportunity to build, invest, or enjoy a recreational retreat. The property has previous perc sites for a conventional septic system, though it will require reevaluation, and soil stability testing will be required, with preliminary work indicating favorable conditions; buyers

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 26079 S Sandgates Rd, Mechanicsville, MD 20659
    26079 S Sandgates Rd, Mechanicsville, MD 20659
    26079 S Sandgates Rd, Mechanicsville, MD 20659
    /4

    $384,900

    Coming Soon
    • 4 Beds
    • 1.5 Baths
    • 960 Sq Ft

    26079 S Sandgates Rd, Mechanicsville, MD 20659

    You'll have to wait a little longer for this great home in Mechanicsville ! Keep checking back and get ready to make your appointment to see it in person! PROFESSIONAL PHOTOS COMING SOON. Mortgage savings may be available for buyers of this listing.

    Dawn Kane Redfin Corp

    26079 S Sandgates Rd, Mechanicsville, MD 20659
  • 25675 Southwell Ln, Hollywood, MD 20636
    25675 Southwell Ln, Hollywood, MD 20636
    25675 Southwell Ln, Hollywood, MD 20636
    /6

    $125,000

    • Land
    • 2.17 Acres
    • $57,604 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
  • 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
Maryland St Marys County Hollywood

Homes for Sale with Acreage in Hollywood, MD

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In Hollywood, there are currently 26 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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