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Hollywood, MD Homes for Sale with Acreage

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  • 23660 Pine View Ln, Hollywood, MD 20636
    23660 Pine View Ln, Hollywood, MD 20636
    23660 Pine View Ln, Hollywood, MD 20636
    /9

    $800,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 3,744 Sq Ft

    23660 Pine View Ln, Hollywood, MD 20636

    This property is located in a rapidly developing area of central St. Mary’s County very close to the expanding county airport, offering strong potential for future growth and investment.The parcel is currently zoned RL (Residential Low Density), which allows for one dwelling unit per acre, with the potential for up to five homes per acre under the current zoning ordinance. Additionally,

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 230-6304

    23660 Pine View Ln, Hollywood, MD 20636
  • 23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    /2

    $464,900 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,634 Sq Ft

    23801 Mcintosh Rd, Hollywood, MD 20636

    Well-maintained home located in the sought-after Leonardtown school district- Duke Elementary, Leonardtown Middle, Leonardtown High School. More details and professional photos coming soon.

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 770-1422

    23801 Mcintosh Rd, Hollywood, MD 20636
  • 44731 Smiths Nursery Rd, Hollywood, MD 20636
    44731 Smiths Nursery Rd, Hollywood, MD 20636
    44731 Smiths Nursery Rd, Hollywood, MD 20636
    /87

    $995,000

    • 4 Beds
    • 3 Baths
    • 2,466 Sq Ft

    44731 Smiths Nursery Rd, Hollywood, MD 20636

    Deep water Colonial on desirable Cuckold Creek! Enjoy water views, and waterfront living, in this charming 4-bedroom, 3-bath home. Have your coffee as you watch the morning sun shimmer on the water, and then end the day on the back deck for a glorious sunset. Situated on the protected waters of Forrest Landing Cove, you can head down to the dock for a relaxing paddle or gentle sail. Minutes from

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 205-2068

    44731 Smiths Nursery 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

    $104,900

    • Land
    • 4.11 Acres
    • $25,523 per Acre

    000 Saint Andrews Church Rd, Leonardtown, MD 20650

    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 conditions; buyers to

    Casey Kennedy Whitetail Properties Real Estate

    000 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 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

    • 3 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 3BR 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
  • 25890 Whiskey Creek Rd, Hollywood, MD 20636
    25890 Whiskey Creek Rd, Hollywood, MD 20636
    25890 Whiskey Creek Rd, Hollywood, MD 20636
    /95

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,671 Sq Ft

    25890 Whiskey Creek Rd, Hollywood, MD 20636

    Welcome to your waterfront sanctuary and entertainers dream home! The custom craftmanship in this home will amaze you. This 4 bedroom 2 1/2 bathroom home has everything at your fingertips. Family room w/fireplace and exposed beams. Built in bar and entertainment space off family room and kitchen. Large gourmet kitchen and formal dining room. Upper level with primary bedroom and primary bathroom.

    Edna Wentworth CENTURY 21 New Millennium

    25890 Whiskey Creek Rd, Hollywood, MD 20636
  • 0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    /18

    $20,000

    • Land
    • 1.23 Acres
    • $16,260 per Acre

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636

    Rarely does a parcel this clean, this well-located, and this perfectly positioned for long-term appreciation come to market — and this 1.23-acre lot on Hollywood Road in Hollywood, Maryland is exactly that. Gently rolling terrain, paved road frontage, power already at the street, zero flood zone, zero wetlands, and zero floodway make this a compelling land hold in St. Mary's County today. Zoned

    Joseph Hawkins Hawkins Real Estate Company

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
  • 25815 Three Notch Rd, Hollywood, MD 20636
    25815 Three Notch Rd, Hollywood, MD 20636
    25815 Three Notch Rd, Hollywood, MD 20636
    /6

    $125,000

    • Land
    • 6 Acres
    • $20,833 per Acre

    25815 Three Notch Rd, Hollywood, MD 20636

    6 Acre Lot in Hollywood

    Gloria Abell Coldwell Banker Premier

    25815 Three Notch 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

    • 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
  • Lot 2 Ewell Ln, Hollywood, MD 20636
    Lot 2 Ewell Ln, Hollywood, MD 20636
    Lot 2 Ewell Ln, Hollywood, MD 20636
    /9

    $200,000

    • Land
    • 3.16 Acres
    • $63,291 per Acre

    Lot 2 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

    Lot 2 Ewell 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
  • 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
  • 44405 5 LOTS K & R Way, Hollywood, MD 20636
    44405 5 LOTS K & R Way, Hollywood, MD 20636
    /2

    $1,300,000

    • 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 RE/MAX One

    44405 5 LOTS K & R Way, 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
  • 43275 Waverly Ct, Hollywood, MD 20636
    43275 Waverly Ct, Hollywood, MD 20636
    /2

    $719,900 Coming Soon

    • 5 Beds
    • 3 Baths
    • 4,252 Sq Ft

    43275 Waverly Ct, Hollywood, MD 20636

    Welcome to this stunning 5 Bedroom, 3 Full Bath Colonial in the desirable Forrest Farm Subdivision. This elegant home offers space, style and thoughtful updates throughout. The impressive Brick Front, Side-Load 2 Car Garage, and long blacktop drive way provide beautiful curb appeal. Located at the end of a quiet court, the property features a fully fenced back yard with a storage shed complete

    Tammy Travers CENTURY 21 New Millennium

    43275 Waverly Ct, 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

    $104,900

    • Land
    • 4.11 Acres
    • $25,523 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
  • 23012 S Pembrook Dr, Hollywood, MD 20636
    23012 S Pembrook Dr, Hollywood, MD 20636
    /2

    $655,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,274 Sq Ft

    23012 S Pembrook Dr, Hollywood, MD 20636

    SPECTACULAR COLONIAL IS SOUGHT AFTER FORREST FARMS. HOME HAS BEEN METICULOUSLY MAINTAINED AND MANY RECENT UPDATES INLUDES...NEW PRIMARY BATH, NEW APPLIANCES, LAUNDRY MOVED TO BEDROOM LEVEL FROM BASEMENT, FRESH LIGHT FIXTURES AND FRESHENED UP PAINT. GREAT FLOOR PLAN FEATURES LARGE OFFICE, OPEN KITCHEN TO FAMILY ROOM, HUGE DINING ROOM AND INCREDIBLE PRIMARY SUITE WITH GORGEOUS BATH. 3 OTHER

    Jennifer Mullennix CENTURY 21 New Millennium

    23012 S Pembrook Dr, Hollywood, MD 20636
  • 24850 Peaceful View Way Ct, Hollywood, MD 20636
    24850 Peaceful View Way Ct, Hollywood, MD 20636
    24850 Peaceful View Way Ct, Hollywood, MD 20636
    /49

    $699,000 New Construction

    • 4 Beds
    • 2.5 Baths

    24850 Peaceful View Way Ct, Hollywood, MD 20636

    Move in ready new construction coming this spring! Located at 24850 Peaceful View Way in Hollywood, MD, this 4-bedroom home sits on a private 1.5-acre cul-de-sac lot, offering space, privacy, and modern farmhouse-inspired design.The exterior features stone skirting, a front load garage, and a welcoming front porch. Inside, the home is designed with high ceilings, upgraded trim details, luxury

    Michele Posey RE/MAX Realty Group

    24850 Peaceful View Way Ct, Hollywood, MD 20636
  • 20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    /28

    $579,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • 24984 Forrest Cove Way, Hollywood, MD 20636
    24984 Forrest Cove Way, Hollywood, MD 20636
    24984 Forrest Cove Way, Hollywood, MD 20636
    /10

    $206,550

    • 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). EQUAL HOUSING OPPORTUNITY. GROUND RENT/HOA/CONDO FEES/FF Fees if any to be verified by purchaser. All offers submitted to HUDHOMESTORE for bid status and availability visit HUDHOMESTORE.

    Christopher White Classic Select Inc

    24984 Forrest Cove Way, Hollywood, MD 20636
  • 24072 Hollywood Rd, Hollywood, MD 20636
    24072 Hollywood Rd, Hollywood, MD 20636
    24072 Hollywood Rd, Hollywood, MD 20636
    /10

    $265,000

    • 5 Beds
    • 1 Bath
    • 1,791 Sq Ft

    24072 Hollywood Rd, Hollywood, MD 20636

    APPOINTMENT ONLY. NO DRIVEBYS. Welcome to endless potential. Situated on a private 2-acre lot, this spacious home features 5 bedrooms and 1 full bathroom, with excellent potential to easily add a second bath, creating even more functionality and value. The fenced yard provides a wonderful space for children or pets to play freely, offering both privacy and peace of mind while enjoying the open

    Taylor Sinclair Five Star Real Estate

    24072 Hollywood Rd, 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 23 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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