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Hollywood, MD Homes for Sale with View

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  • /62

    $620,000

    • 5 Beds
    • 4 Baths
    • 3,724 Sq Ft

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    Price Improvement! This adjustment creates a fantastic opportunity for buyers to own a well-maintained home — one of the largest in the subdivision. Schedule your showing today before it’s gone. Welcome home! 41377 Doctors Crossing Rd is a well-maintained home located in the sought-after Clark’s Rest community — where comfortable living meets a vibrant neighborhood lifestyle, with a POND just

    Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
  • /3

    $764,987 Coming Soon

    • 3 Beds
    • 4 Baths
    • 2,551 Sq Ft

    43816 Raspberry Ln, Hollywood, MD 20636

    Coming soon. should be active next month. Call for more information

    Patrick Dugan O'Brien Realty ERA Powered

    43816 Raspberry Ln, Hollywood, MD 20636
  • /2

    $605,000 Coming Soon

    • 4 Beds
    • 4.5 Baths
    • 4,280 Sq Ft

    43675 Wild Iris St, California, MD 20619

    WELCOME TO 43675 WILD IRIS STREET. THIS SPACIOUS HOME FEATURES AN OPEN FLOOR PLAN WITH HUGE ROOMS AND A GREAT FLOW THROUGHOUT. YOU'LL ENTER ON THE COVERED PORCH TO AN INVITING FOYER WITH A FORMAL DINING ROOM AND A LIVING ROOM/OFFICE ON EITHER SIDE. NEXT YOU'LL NOTICE THE GENEROUS FAMILY ROOM WHICH FLOWS TO THE BREAKFAST AREA AND AMAZING KITCHEN WITH OVERSIZED ISLAND AND AMPLE CABINET AND COUNTER

    Jennifer Mullennix CENTURY 21 New Millennium

    43675 Wild Iris St, California, MD 20619
  • /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 New Millennium

    24065 Pappys Way, Hollywood, MD 20636
  • /80

    $599,900

    • 3 Beds
    • 2 Baths
    • 2,514 Sq Ft

    43088 Island View, Hollywood, MD 20636

    SPEND YOUR SUMMER HERE AND/OR EVERYDAY!! WATERFRONT - Completely Renovated Home - New Roof, New Well, New Windows, New HVAC, New Water Heater, New Attic Insulation, New doors, siding, and gutters, New Kitchen with stainless steel Appliances and Quartz Countertops, View of the water from the kitchen, Dining, Primary Bedroom, back Covered Deck Area, New Bathrooms with porcelain, New paint

    Donna Lacey CENTURY 21 New Millennium

    43088 Island View, Hollywood, MD 20636
  • /62

    $623,000

    • 2 Beds
    • 2 Baths
    • 1,226 Sq Ft

    43732 Raspberry Ln, Hollywood, MD 20636

    Premier Waterfront Retreat with Unrivaled Patuxent River ViewsThis extraordinary residence rises above all other waterfront offerings—an exceptional retreat that delivers the best of both worlds with awe inspiring views of the water and the surrounding wooded landscape. From its commanding position, the home offers sweeping 180 degree vistas of the Patuxent River, creating a true “top of the

    Man Ngo Pearson Smith Realty, LLC

    43732 Raspberry Ln, 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
  • /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
  • /5

    $72,500

    • Land
    • 27,442 Sq Ft
    • $115,079 per Acre

    42209 Ridge Rd, Mechanicsville, MD 20659

    Motivated seller! Bring all offers. Discover a rare opportunity to own a stunning 0.63-acre waterfront parcel in the coveted St. Marys Beach community. With an impressive stretch of ocean frontage, this land offers unparalleled access to the serene beauty of coastal living. Imagine waking up to the soothing sounds of waves and the gentle ocean breeze, creating a perfect backdrop for your dream

    Marvena Baird Samson Properties

    42209 Ridge Rd, Mechanicsville, MD 20659
  • /2

    $338,500 Open Sun 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 980 Sq Ft

    26412 Hillendale Rd, Hollywood, MD 20636

    Imagine life at 26412 Hillendale Road, a recently updated one level rambler tucked away in the desirable, water oriented Hollywood Shores community. This residence offers 3 bedrooms and 1 1/2 bathrooms with 980 square feet of move in ready living area offering the perfect blend of fresh modern finishes and relaxed Southern Maryland living, just moments from the water and quaint neighborhood

    Luke Pahel The Southside Group Real Estate

    26412 Hillendale Rd, Hollywood, MD 20636
  • /37

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,147 Sq Ft

    23104 Sweetbay Ln, California, MD 20619

    **Back on the market and a fresh opportunity to make it yours!** 4-bedroom, 2.5-bath home on a tree-lined corner lot in the desirable Wildewood community. Custom interior shutters, new luxury vinyl flooring, and freshly installed carpet (March 2026) add warmth and style throughout. The kitchen features updated stainless steel appliances, while thoughtful design details include a geometric accent

    Colin McHugh O'Brien Realty ERA Powered

    23104 Sweetbay Ln, California, MD 20619
  • /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
  • /2

    $539,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,003 Sq Ft

    23302 Misty Pond Ln, California, MD 20619

    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 fresh paint on the front door too 2026, Both HVAC system were replaced in 2022-2023. Home features open floor plan in the traditional colonial style. Kitchen island and deck overlooking a small pond in the

    James Dick Long & Foster Real Estate, Inc.

    23302 Misty Pond Ln, California, MD 20619
  • /56

    $959,900

    • 5 Beds
    • 3.5 Baths
    • 3,408 Sq Ft

    44760 Joy Chapel Rd, Hollywood, MD 20636

    Hollywood waterfront on Cuckold Creek—custom-built, one-owner home offering space, quality, and beautiful water views. The main level features hardwood floors throughout, a primary bedroom with full bath, and a well-appointed kitchen with granite countertops and custom cabinetry, open to the breakfast area and family room with a gas fireplace. A bright sunroom overlooks the creek and provides

    Carol Kalmus-Choporis Century 21 Redwood Realty

    44760 Joy Chapel Rd, Hollywood, MD 20636
  • /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
  • /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
  • /45

    $999,500 Open Sat 10AM - 12PM

    • 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
  • /34

    $98,900

    • 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
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    $499,000

    • 4 Beds
    • 3.5 Baths
    • 2,264 Sq Ft

    44965 Blackistone Cir, Hollywood, MD 20636

    Discover a captivating blend of comfort and nature in this stunning waterview home, nestled along the serene banks of Cuckhold Creek. With 2,264 sq. ft. of thoughtfully designed living space, this residence features four spacious bedrooms and three and a half bathrooms, perfect for both relaxation and entertaining. The inviting interior boasts a cozy gas fireplace, ideal for chilly evenings, and

    Mike Sweeney Taylor Properties

    44965 Blackistone Cir, Hollywood, MD 20636
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