101

Hollywood, MD Homes for Sale

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  • /43

    $385,000

    • 4 Beds
    • 3.5 Baths
    • 2,165 Sq Ft

    43640 Winterberry Way, California, MD 20619

    Nestled in the highly desirable Evergreen Park section of Wildwood, this 4-bedroom, 3.5-bath townhome is the perfect blend of comfort, convenience, and community charm. From the moment you step inside, you’re greeted with a bright and open foyer. On the entry level, you’ll find a thoughtfully designed large walkout bedroom with its own full bath, walk-in closet, and private sliding glass door

    Diana Washabaugh CENTURY 21 New Millennium

    43640 Winterberry Way, California, MD 20619
  • /49

    $459,000 Open Sun 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 2,104 Sq Ft

    43915 Honeysuckle Way, California, MD 20619

    Beautiful Single family home with 2-car garage in the charming Sycamore Hollow section of Wildewood! Step inside to a classic colonial floor plan with living room and dining room plus separate (large!) family room with gas fireplace open to kitchen with breakfast nook. Kitchen features gas cooking, upgraded stainless steel appliances, and large breakfast bar. Family room leads out to a great

    Christina Fischer Coldwell Banker Jay Lilly Real Estate

    43915 Honeysuckle Way, California, MD 20619
  • /36

    $439,000

    • 3 Beds
    • 2 Baths
    • 1,523 Sq Ft

    23125 Winterberry Ln, California, MD 20619

    Charming Corner-Lot Gem in Wildewood with Modern Upgrades! Step into comfort and convenience with this beautifully maintained home nestled on a spacious corner lot. Featuring a 2-car garage and paved driveway, this property offers curb appeal and functionality from the moment you arrive. Recent Updates Include a New roof (2024),New HVAC system (2024) and Newer gas on-demand hot water tankless

    Jan Kleponis O'Brien Realty ERA Powered

    23125 Winterberry Ln, California, MD 20619
  • /34

    $489,990 Open Sat 12PM - 5PM

    • 5 Beds
    • 4.5 Baths
    • 3,455 Sq Ft

    44018 Bellflower Way, California, MD 20619

    Price Reduction! Motivated Seller! Welcome to a wonderfully updated and maintained 5-bedroom, 4.5-bathroom colonial home in the highly sought-after Dahlia Park of Wildewood community. This spacious oasis has been restored to new-like condition with new paint and carpet throughout, new bathroom updates on all four levels of living. The main level features a open-concept layout (no doors) which

    Christina Proctor HomeSmart

    44018 Bellflower Way, California, MD 20619
  • /35

    $489,990 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,553 Sq Ft

    44014 Silverwood Ln, California, MD 20619

    Welcome to 44014 Silverwood Lane, a stunning Colonial home nestled in the highly sought-after Wildewood community. This exquisite property boasts four spacious bedrooms, two and a half well-appointed bathrooms, and a suite of modern amenities that blend seamlessly with its timeless architectural charm.As you approach the residence, you are greeted by the inviting ambiance of the covered front

    Shelia Kuhfahl CENTURY 21 New Millennium

    44014 Silverwood Ln, California, MD 20619
  • /51

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 3,118 Sq Ft

    23185 Piney Wood Cir, California, MD 20619

    Beautifully Updated Colonial on One Acre in WildwoodThis stunning colonial home sits on a spacious one-acre lot in Wildwood and features numerous high-end updates throughout. The heart of the home is the beautifully remodeled kitchen (2022), showcasing new cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining.The main

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23185 Piney Wood Cir, California, MD 20619
  • /3

    $299,999

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    24992 Sotterley Rd, Hollywood, MD 20636

    Welcome to your charming retreat in the heart of Hollywood, MD! This delightful property features a cozy front porch that invites you to unwind and enjoy the serene surroundings. Nestled on over an acre of lush, level land, this home provides a picturesque view of nature's beauty. Imagine sipping your morning coffee while deer occasionally grace the yard with their presence. The tranquility and

    Ron Lord Home Towne Real Estate

    24992 Sotterley Rd, Hollywood, MD 20636
  • /4

    $150,000

    • Land
    • 4.2 Acres
    • $35,714 per Acre

    43245 Joy Ln, Hollywood, MD 20636

    Discover the perfect blend of privacy, convenience, and opportunity with this beautifully wooded 4-acre lot. Tucked away in a peaceful setting, this property offers endless possibilities. Whether you’re looking to build your dream home, explore development potential, or secure a smart investment for the future.The land features a level build site perched on a ridge, providing a stunning

    Michael Fitzgerald, II RE/MAX Closers

    43245 Joy Ln, Hollywood, MD 20636
  • /35

    $450,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    45429 Englewood Way, California, MD 20619

    Luxury Living in Style describes this stunning end unit townhome with 2,548 finished sq ft in a premium location close to schools, shopping, restaurants and commuter routes in California, Maryland. This beautifully maintained 3-level end-unit of superb living space including a fully finished basement. With 3 spacious bedrooms, 3 full bathrooms, and a convenient half bath, there’s room for

    Mary Chambers JPAR Real Estate Professionals

    45429 Englewood Way, California, MD 20619
  • /137

    $1,799,000

    • 5 Beds
    • 5 Baths
    • 4,857 Sq Ft

    24754 Half Pone Point Rd, Hollywood, MD 20636

    Waterfront Craftsman on the Patuxent River – Built for Coastal LivingExperience the perfect blend of luxury and lifestyle in this stunning 2015 waterfront Craftsman home nestled on the Patuxent River. Designed for comfort and entertaining, the home showcases panoramic water views, a flowing open floor plan, and high-end finishes throughout.The heart of the home is the gourmet kitchen,

    Jennifer Goddard CENTURY 21 New Millennium

    24754 Half Pone Point Rd, Hollywood, MD 20636
  • /65

    $609,900

    • 4 Beds
    • 3.5 Baths
    • 3,234 Sq Ft

    44628 Cedar Ct, California, MD 20619

    This is the story of a charming home in Wildewood's premier neighborhood. Situated on a 1.21 acre lot on a peaceful cul-de-sac, with a lush green lawn dappled with shade trees, where the scenery is beautiful all year round. Gorgeous hardscape patio out back with a stone fire pit, complete with a seasoned woodpile, is ideal for outdoor gatherings. A large 2-car garage includes a utility

    Kimberly St. Laurent RE/MAX One

    44628 Cedar Ct, California, MD 20619
  • /99

    $649,000

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft

    41402 Silver Charm Ct, Leonardtown, MD 20650

    Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of Leonard's Grant community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field. Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches.

    Kelly Padgett CENTURY 21 New Millennium

    41402 Silver Charm Ct, Leonardtown, MD 20650
  • /35

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 3,416 Sq Ft

    23920 Druid Hills Dr, California, MD 20619

    House includes a $30K solar systems where future homeowners will enjoy for a long time. Installed only couple years ago

    nugent nguyen Westgate Realty Group, Inc.

    23920 Druid Hills Dr, California, MD 20619
  • /33

    $485,000

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    24735 Red Hill Ct, Hollywood, MD 20636

    Welcome to this beautiful and spacious single-story home located in a very peaceful community. Perfectly designed for comfort and convenience, this property offers the ideal balance of modern living and serene surroundings. The open floor plan is thoughtfully designed, providing plenty of space to entertain and enjoy family gatherings. Every corner of this home feels inviting and expansive. The

    John Gatton CENTURY 21 New Millennium

    24735 Red Hill Ct, Hollywood, MD 20636
  • /52

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,296 Sq Ft

    23242 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Clark’s Rest community of Leonardtown! Boasting nearly 3,300 square feet with an open floor plan filled with natural light, this home offers a perfect blend of comfort and functionality.The main level features spacious living and dining areas that flow effortlessly into a modern

    Matthew Burgan Infinitas Realty Group

    23242 Clarks Rest Rd, Leonardtown, MD 20650
  • /26

    $470,000

    • 4 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    41900 Nazareth Ct, Leonardtown, MD 20650

    Welcome to the Academy Hills of Leonardtown. The main level features a traditional floor plan, recent upgrades including new carpet August 2025, stainless steel kitchen appliances, plenty of cabinet space, a formal dining room, and a convenient powder room. Major system updates include a brand-new Roof and a new HVAC system for added peace of mind.Upstairs, newly installed banisters, the

    Marizel Brewington RE/MAX One

    41900 Nazareth Ct, Leonardtown, MD 20650
  • /27

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    24675 Blackistone Rd, Hollywood, MD 20636

    FABULOUS ONE LEVEL LIVING WITH RAMP TO THE FRONT DOOR***3 BEDROOM***2 BATH RAMBLER***DOUBLE HUNG WINDOWS***LARGE EAT-IN KITCHEN***HARDWOOD FLOORS***FRESHLY PAINTED***UPDATED SEPTIC***2 CAR DETACHED GARAGE***SUN ROOM PORCH***WORKSHOP***1 CAR CARPORT***GENERATOR***METICULOUSLY MAINTAINED LAWN***PANTRY***HEAT PUMP WITH OIL BACK UP***FRONT DOOR RAMP***UPDATED METAL ROOF***2025 NEW DEHUMIDIFIER IN THE

    Candide Rayle CENTURY 21 New Millennium

    24675 Blackistone Rd, Hollywood, MD 20636
  • /33

    $219,900

    • 3 Beds
    • 2 Baths
    • 2,020 Sq Ft

    42264 Ridge Rd, Mechanicsville, MD 20659

    Investor alert! Great fix and flip! 4 bedroom (possibly 5) 2 bath SFH with detached garage and a guest house with 2 rooms, nice sized lot. Property sold AS-IS, CASH or HARD MONEY LOAN.

    Heidi Heiderman Samson Properties

    42264 Ridge Rd, Mechanicsville, MD 20659
  • /79

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality.The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your

    Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • /59

    $610,000

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

    23264 Lindsay Dr, Leonardtown, MD 20650

    **Custom Floorplan** Front Load Garage with expanded guest parking on driveway, Upgraded cabinets, Countertops, and custom Primary suite walk in frameless glass shower. Built on an oversized premium corner lot. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which transfers to the new homeowner. VA assumable

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • /4

    $799,000

    • Land
    • 4.7 Acres
    • $170,000 per Acre

    0 Cottonwood Pkwy, Wildewood, MD 20619

    Elevate your investment portfolio with the remarkable opportunity presented by Cottonwood Parkway Outparcel C in the esteemed Wildewood Technology Park, California, MD. This prime plot, meticulously zoned for Office Business Park, offers an unparalleled canvas for visionary investors seeking to shape the commercial landscape. Positioned to cater to the evolving demands of office space in the

    Thomas McKay Berkshire Hathaway HomeServices PenFed Realty

    0 Cottonwood Pkwy, Wildewood, MD 20619
  • /50

    $995,000

    • 5 Beds
    • 7 Baths
    • 8,640 Sq Ft

    44605 Old Saint Andrews Church Rd, California, MD 20619

    Endless Possibilities on 20+ Private Acres in the Heart of California, MD!Discover a unique opportunity with this marvelous estate home set on over 20 secluded acres—offering the perfect blend of privacy and convenience. Located just minutes from PAX River NAS, Solomons Island, shopping, dining, theaters, and more, this property is a rare gem in Southern Maryland.Whether you're

    Conor Loughran CENTURY 21 New Millennium

    44605 Old Saint Andrews Church Rd, California, MD 20619
  • /81

    $1,775,000

    • 6 Beds
    • 5.5 Baths
    • 6,646 Sq Ft

    45216 Clarkes Landing Rd, Hollywood, MD 20636

    VERY PRIVATE POINT of land with all-brick sprawling residence was designed to take full advantage of the waterfront lifestyle at this unique site. Cuckold Creek is highly sought after for boating and watersports, depth of water, surrounding value. This point has a unique private beach, a deep water private pier, and a beautiful elevation. Catch your own blue crabs at the pier and have summer

    Chris McNelis Berkshire Hathaway HomeServices PenFed Realty

    45216 Clarkes Landing Rd, Hollywood, MD 20636
  • /59

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 3,014 Sq Ft

    41998 Pleasant Valley Ct, Hollywood, MD 20636

    This exceptional one-level rambler sits on 17 acres of peaceful, picturesque land, offering a rare blend of upscale living and rural charm. From the moment you arrive, you'll appreciate the serenity of the surroundings complete with scenic pond views, a circular paved driveway, and ample space for both leisure and purpose. Step inside to find an open-concept layout designed for both comfort and

    Deanna Havenner CENTURY 21 New Millennium

    41998 Pleasant Valley Ct, Hollywood, MD 20636
  • /82

    $685,000

    • 4 Beds
    • 4.5 Baths
    • 4,399 Sq Ft

    22951 Cattail Ln, California, MD 20619

    Welcome to 22951 Cattail Ln, a beautifully maintained custom brick home in the sought-after Redwood subdivision of Wildewood. Perfectly situated near top-rated schools, shopping, and PAX River NAS, this home offers a blend of elegance, functionality, and modern updates. Step inside to find grand-scale living with 4 spacious bedrooms and 3 full baths upstairs, plus a flex room and full bath in the

    Charlotte Long EXP Realty, LLC

    22951 Cattail Ln, California, MD 20619
  • /40

    $625,000

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    45352 Sypher Rd, California, MD 20619

    This adorable waterfront getaway is the perfect spot for you to fully unwind and relax. Located directly along Sam Abell Cove, you'll enjoy peace and serenity while only living a short 5 minute drive from shopping or take a short boat ride to Solomons Island and other locations along the Patuxent River for drinks and dinner. There is also a 99 acre park just down the road. This charming cottage

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    45352 Sypher Rd, California, MD 20619
  • /78

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft

    43088 Island View, Hollywood, MD 20636

    POSSIBLE OWNER FINANCING TO QUALIFIED BUYER - WATERFRONT - it is WAITING FOR YOU! Completely Renovated Home - New Roof, New Well, New Windows, New HVAC, New Water Heater, New Attic Insulation, New doors, siding, and gutters, New Kitchen and Appliances with Quartz Countertops, New Bathrooms with porcelain, New paint throughout, refinished hardwood floors, new paved driveway, new exterior

    Donna Lacey CENTURY 21 New Millennium

    43088 Island View, Hollywood, MD 20636
  • /3

    $95,000

    • Land
    • 0.84 Acre
    • $113,095 per Acre

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Prime Build-Ready Lot – Bring Your Dream Home to Life!Discover the perfect canvas for your dream home on this beautiful [size] acre lot in [location]! This perc-tested property is ready for construction, offering the flexibility to bring your own builder or partner with Graham & Co Custom Creations to design and build a custom home tailored to your vision.Located in a serene

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • /91

    $674,900 Open Sat 10AM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 3,478 Sq Ft

    23773 Meredith Ct, Hollywood, MD 20636

    Spacious home in desirable Hollywood location. (Abell's Ridge) The main level greets you with hardwood flooring in the Foyer. Large owners suite with two walk in closets. The owner's full bath features tile flooring, a double jetted soaking tub, separate shower.Four car garage with work area of garage heated. New HVAC in 2023. Fireplace has wood stove insert. Unfinished basement .

    Gloria Abell Coldwell Banker Jay Lilly Real Estate

    23773 Meredith Ct, Hollywood, MD 20636
  • /4

    $139,900

    • Land
    • 1.61 Acres
    • $86,894 per Acre

    44459 Marymax Ln, Hollywood, MD 20636

    Nothing left to do! The lot is perc'd, cleared and prepped. A building permit is in hand for the house you see pictured here. Even the impact fee has been paid. Electric has been brought to the end of the street. So much value here! Dreaming of building your perfect home but feeling overwhelmed by the process and permit delays? This exceptional lot in the heart of Hollywood eliminates the

    Michelle Camaioni RE/MAX One

    44459 Marymax Ln, Hollywood, MD 20636
  • /5

    $245,000

    • 2,160 Sq Ft

    23706 Three Notch Rd, Hollywood, MD 20636

    LOWER PRICE! DO NOT ATTEMPT TO ENTER THE HOUSE! Owner is unsure of structural condition. Said home was vandalized and stripped of most everything. It is at best, a Major Rehab. No one is to enter the Property without special permission and having signed a Waiver. If your Client wants to see the interior, it can be arranged after signing Waivers. Anyone entering the home would have had to sign

    Don Wares Long & Foster Real Estate, Inc.

    23706 Three Notch Rd, Hollywood, MD 20636
  • /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

    Jessica Raley CENTURY 21 New Millennium

    26350 Three Notch Rd, Mechanicsville, MD 20659
  • /6

    $899,000

    • Land
    • 1.29 Acres
    • $696,899 per Acre

    45410 Clarks Mill Rd, Hollywood, MD 20636

    DEEP WATER Don't miss this opportunity on some of the best waterfront you can find in Southern Maryland .Minutes from Solomons Island and the Chesapeake Bay. Close to shopping, restaurants,and entertainment. Build your waterfront oasis here. 4 lots totaling 2.5 acres on Hickory Landing Creek . There is only one address assigned to one of the lots , but the parcels included are parcels

    Steve Lowe United Real Estate Premier

    45410 Clarks Mill Rd, Hollywood, MD 20636
  • /2

    $44,900

    • Land
    • 0.71 Acre
    • $63,239 per Acre

    25106 Pinto Dr, Hollywood, MD 20636

    0.71 Acres of Land for Sale: Hollywood, Maryland 2063625106 Pinto Dr, Hollywood, MD 20636Features:Land is Approximately 5.34 Miles Away from Patuxent River (See Aerial Map.)Land is Approx. a 39 Minute Drive to King George, Virginia.Zoning:Residential

    Anjie Deonauth Rise Real Estate, LLC

    25106 Pinto Dr, 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

    Catherine Rose RE/MAX One

    44405 5 LOTS K & R Way, 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
  • /2

    $125,000

    • Land
    • 1.19 Acres
    • $105,042 per Acre

    24984 Sotterley Rd, Hollywood, MD 20636

    Emphasizing Key Features and Land Details: Discover the opportunity to own an expansive lot with an artisanal well on-site, offering over an acre of prime potential without HOA constraints. This level lot, previously home to a house, presents a clean canvas for your dream build. Adjacent property house is also available for sale, offering an extraordinary option for increased land ownership or

    Ron Lord Home Towne Real Estate

    24984 Sotterley Rd, Hollywood, MD 20636
  • /2

    $29,000

    • Land
    • 0.37 Acre
    • $78,378 per Acre

    0 Holly Ln Unit MDSM2023572, Mechanicsville, MD 20659

    Welcome to your future haven on this expansive 16,117 square foot lot, perfectly positioned near the Cape St Mary's Marina at the end of the street. This prime location offers a harmonious blend of tranquility and convenience, with nearby attractions such as Seabreeze Restaurant, Snow Hill Park, Budds Creek Motocross Park, Potomac Speedway, and the breathtaking Chesapeake Bay. Enjoy seamless

    Samara Dinnius JPAR Real Estate Professionals

    0 Holly Ln Unit MDSM2023572, Mechanicsville, MD 20659
  • /5

    $485,000

    • 3 Beds
    • 2.5 Baths
    • 2,448 Sq Ft

    44947 Blackistone Cir, Hollywood, MD 20636

    Dawn Popham Samson Properties

    44947 Blackistone Cir, Hollywood, MD 20636
  • /5

    $750,000

    • Land
    • 82.74 Acres
    • $9,065 per Acre

    0 Saint Andrews Church Rd, California, MD 20619

    Mike Jordan CENTURY 21 New Millennium

    0 Saint Andrews Church Rd, California, MD 20619

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