Hollywood Homes for Sale

Hollywood Homes for Sale

Welcome to Hollywood, Maryland – a charming community nestled in the heart of St. Mary’s County, where the warmth of small-town living meets the beauty of the Chesapeake Bay. This picturesque area is known for its friendly atmosphere, stunning waterfront views, and a rich history that dates back to the early 1600s. With its serene landscapes and close-knit community, Hollywood is the perfect place to call home.

As you explore the homes for sale in Hollywood, you’ll discover a delightful array of properties that cater to various lifestyles and preferences. From cozy single-family homes to spacious waterfront estates, there’s something for everyone in this enchanting town. Many of these homes boast modern amenities while retaining their classic charm, ensuring a comfortable living experience for families and individuals alike.

Hollywood’s prime location offers residents easy access to outdoor activities, including boating, fishing, and hiking in nearby parks. The town is also just a short drive from the vibrant cities of Lexington Park and California, providing a perfect blend of tranquility and accessibility to shopping, dining, and entertainment.

In addition to its natural beauty, Hollywood is home to a strong sense of community. Local events, farmers' markets, and festivals are frequent, allowing residents to connect and build lasting friendships. With its welcoming spirit and stunning surroundings, Hollywood, MD, is a hidden gem waiting for you to discover. Explore the homes for sale today and take the first step toward your dream life in this idyllic town!

Newest Hollywood Homes for Sale

$629,900
4 Beds ⋅ 4 Baths
Stunning QBH Preston Model with nearly 4,100 finished square feet! This pristine Colonial offers exceptional space, quality finishes, and thoughtful upgrades throughout. The main level features beautiful hardwood flooring, a formal sitting room with elegant picture-frame molding, a formal dining room accented by crown and chair-rail molding, and a convenient half bath. The upgraded gourmet kitchen boasts an oversized center island, stainless steel appliances, and gas cooktop, opening to an inviting family room with a cozy gas fireplace. Upstairs, you'll find four spacious bedrooms and two full baths, including an impressive primary suite with a luxurious bath featuring dual sinks, a soaking tub, and a massive tiled shower. The finished lower level provides even more living space with a dedicated theater room, recreation room, and full bath. Outside, enjoy a private backyard with a deck, wrought-iron fencing, and storage shed, along with an irrigation system and convenient two-car side-load garage. Ideally located just minutes from PAX NAS and close to schools, shopping, restaurants, and everyday conveniences. An added opportunity for qualified buyers: the seller is open to discussions regarding the assumption of the existing VA loan at an attractive 3.5% interest rate. Buyers should consult with their lender regarding eligibility, assumption requirements, and available terms.

24318 Miley Dr, Hollywood

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$384,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 2-bath home offering 1,316 square feet of comfortable living space on nearly half an acre in Hollywood. Originally built in 1955, the home blends classic character with extensive modern improvements. The renovated kitchen features quartz countertops, stainless steel appliances, and updated finishes. The laundry room and all three bedrooms have also been refreshed, creating a clean, move-in-ready feel. The spacious primary bedroom includes a large custom closet organizer designed to provide convenient storage for clothing, shoes, handbags, and accessories. The beautifully renovated primary bathroom features a tiled shower, modern fixtures, and stylish finishes. A new enclosed propane fireplace and chimney, installed in 2024, create a warm and inviting gathering space. Additional improvements include a remediated and sealed crawlspace with a new weather barrier, French drains, and a sump pump completed in 2024. Enjoy the outdoors from the composite rear deck, updated in 2022, or the newly updated composite front deck completed in 2026. A spacious 12-by-20 utility shed provides excellent storage for lawn equipment, tools, hobbies, and recreational gear. Conveniently located approximately 10 minutes from the local hospital, Naval Air Station Patuxent River, shopping, dining, and everyday conveniences, with easy access to Leonardtown, California, parks, and other popular Southern Maryland destinations. This thoughtfully updated property offers modern amenities, generous storage, useful outdoor space, and a convenient location. Schedule your showing and see everything this Hollywood home has to offer!

24570 Moran Rd, Hollywood

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$724,900
3 Beds ⋅ 4 Baths
WATERFRONT WITH A PRIVATE PIER on 0.56 acres in Hollywood. One level living at its best: an oversized primary suite stretching nearly 26 feet with private bath and dual closets, two more main level bedrooms, and 3 full baths. A fireplace anchors the living room, and the island kitchen opens to a sunny breakfast nook. Host in the 20 foot dining room, slow down in the spacious sunroom, and spread out on the patio built for crab feasts and long summer evenings. The finished lower level adds two generous flex rooms, a 14x14 laundry room, and real storage, plus an attached carport. Covered front porch out front, water out back. Sold as-is and priced accordingly, this one is great for anyone with vision and a chance to build instant equity in a setting you simply cannot recreate. Waterfront with a private pier does not come along often in St. Mary's County. Come see it before someone else does

24740 Marva Point Way, Hollywood

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$799,000
5 Beds ⋅ 3 Baths
Welcome to Hickory Landing Waterfront property. The tree-filled private and quiet 17+ acre property is located on a cove off of Cuckold Creek. Experience breathtaking views from both the living room and the upper level, offering a perfect backdrop for daily living and relaxation. Chef's kitchen features custom solid maple painted cabinets, providing timeless elegance and ample storage space for the discerning cook. This property was built in 1983 and expanded in 1990. This is a rare parcel of land offering privacy and natural beauty. The home has views of the water and abundant wildlife. The 17+ acres and house are on mostly level land, the rest of the land is wooded with walnut, poplar,oak, maple and cypress trees which you can view down the long driveway to the house. There is a pier on the property that is private for the neighbors use. There is 1 boat slip open. This water is good for a pontoon boat , Canoe, shallow drafted boats. The pier is being redone in August 2026. The home is approximately 2,727Sq.Ft. with 5 bedrooms and 3 baths. 2 outbuildings. NO HOA. Text listing agent for more information.

44908 Hickory Landing Way, Hollywood

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990
$334,900
3 Beds ⋅ 1 Baths

26260 Skyview Dr, Hollywood

Listing courtesy of Home Towne Real Estate. Contact: 8882252736
$764,987
3 Beds ⋅ 3 Baths
Experience timeless English Tudor character paired with sweeping, unobstructed views of the Patuxent River. From the moment you step inside, the home’s expansive windows frame miles of serene waterfront, filling each room with natural light and a sense of calm that only riverside living can offer. With three bedrooms plus a dedicated office, the layout balances comfort and functionality—ideal for a full‑time residence or a peaceful weekend retreat. The original portion of the home features a classic kitchen, while the thoughtfully renovated section adds a second kitchen, offering flexibility for entertaining, multigenerational living, or reimagining the space to suit your vision. A two‑car garage and an unfinished basement currently used as a workshop provide abundant storage and room for hobbies, projects, or future expansion. Whether you dream of crafting the perfect waterfront getaway or designing a year‑round sanctuary, this property is ready to become your canvas. Beyond the walls of the home, the property invites you to fully embrace the natural beauty and recreation the Patuxent River is known for. Hunt for age‑old shark teeth along the shoreline, harvest oysters straight from the water, and enjoy crabbing during warm Maryland seasons. Whether you’re an outdoor enthusiast or simply love the idea of stepping into a slower, more peaceful rhythm, this location offers experiences you won’t find anywhere else. Waterfront living is within reach. Come experience the view, feel the tranquility, and imagine the possibilities waiting for you here.

43816 Raspberry Ln, Hollywood

Listing courtesy of O'Brien Realty ERA Powered. Contact: 3018632400
$1,350,000
4 Beds ⋅ 3 Baths
Nestled along the shores of the Patuxent River is this very private, custom-built, all brick home with beautiful hardwood floors throughout, modern kitchen and baths situated on 5 sprawling acres. Riprapped shoreline, professionally landscaped yard, 4 stall horse barn, dog run and more. Enjoy nature's beauty on the water; conveniently located for a D.C. commute. A great get-away for enjoying peace and tranquility in the Country.

43410 Old Wharf Ln, Hollywood

Listing courtesy of KW Metro Center. Contact: (703) 535-3610
$679,900
5 Beds ⋅ 4 Baths
From its inviting curb appeal to its spacious, thoughtfully designed interior, this stunning brick-front Colonial offers nearly 4,500 square feet of finished living space and is perfectly situated on a private 1-acre corner lot in the sought-after Forrest Farm community. Featuring 5 bedrooms and 3.5 baths, this exceptional home is designed for both comfortable everyday living and effortless entertaining. The main level welcomes you with an inviting foyer, elegant formal dining room, spacious sitting room/formal living room, and a private home office. The impressive two-story great room features a cozy gas fireplace and flows seamlessly into the gourmet kitchen, complete with recently replaced stainless steel appliances, abundant cabinetry, and generous prep space. Upstairs, you'll find spacious bedrooms, including a luxurious primary suite with vaulted ceilings designed as a private retreat. The fully finished lower level adds incredible versatility with a large recreation room, fifth bedroom, and full bath - perfect for guests, multigenerational living, or additional entertaining space. Step outside to enjoy the expansive deck overlooking the fully fenced backyard, offering plenty of room for outdoor gatherings, pets, and play. Additional highlights include a shed, side-load two-car garage, beautiful curb appeal, and an unbeatable corner-lot setting. Minutes to PAX NAS! Close to Restaurants, Schools, and Shopping!

23017 Holloway Ct, Hollywood

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,450,000
1 Beds ⋅ 1 Baths
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 buildings, including two stick-built structures, one featuring a second-floor one-bedroom, one-bath apartment with beautiful water views. Two metal buildings and an impressive airplane hangar-style garage with two oversized roll-up doors provide exceptional space for vehicle collections, RVs, boats, equipment, workshops, or storage. An additional A-frame building adds even more flexibility. Designed for convenience and functionality, the property features multiple 60-amp RV hookups, along with plumbing and electric throughout the buildings, making it ideal for a variety of residential, recreational, or commercial-style uses. This property is exceptional on its own, but when assembled with the waterfront estate across the street, it creates one of Southern Maryland's most remarkable legacy properties. Whether you're seeking privacy, expansive acreage, unmatched storage, or the opportunity to create a one-of-a-kind estate, this offering is truly unlike any other.

24715 Half Pone Point Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$4,595,000
4 Beds ⋅ 7 Baths
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 craftsmanship are evident throughout, blending timeless elegance with modern luxury. Designed for both grand-scale entertaining and comfortable everyday living, the estate features a private elevator, state-of-the-art theater room, wine room, game room, custom entertaining bar, and resort-style amenities including a spectacular infinity-edge pool and expansive outdoor living spaces. The property is further enhanced by advanced whole-home automation, integrated smart-home technology, comprehensive high-definition surveillance systems, a secure safe room, and numerous additional proprietary security features. For sport and recreation, the residence also includes a private indoor commercial-grade shooting range—a rare amenity seldom found in residential properties. Just minutes by boat from Solomons Island and the Chesapeake Bay, this remarkable property delivers an unparalleled waterfront lifestyle where privacy, sophistication, and natural beauty converge. Created for those who value discretion as much as luxury, certain features and specifications of the estate are intentionally withheld from public marketing materials. Qualified purchasers only. Private showings are available by appointment for financially qualified buyers. Proof of funds or lender pre-approval may be required prior to touring the property. Due to the nature of certain security, technology, and infrastructure systems, prospective purchasers may be asked to execute a confidentiality agreement before receiving access to selected property information and features.

24730 Half Pone Point Rd, Hollywood

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$499,000
3 Beds ⋅ 2 Baths
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 with french drains, centrally located in Hollywood close to park. Close to downtown Leonardtown, hospital, shopping, and schools.

24301 Old Hollywood Rd, Hollywood

Listing courtesy of RE/MAX One. Contact: 4437718009
$355,000
3 Beds ⋅ 2 Baths
Located on a beautiful corner lot in Hollywood, this charming ranch-style home is ready to welcome its next owner. Set on a flat .60-acre lot backing to trees, the property offers mature landscaping, a peaceful setting, and plenty of outdoor space to enjoy. Inside, you’ll find three bedrooms, one and a half baths, and a built-in bonus room off the back—perfect for a hobby space, library, art studio, home office, or anything your imagination can dream up. Conveniently located close to Historic Sotterley, just 8 miles from Patuxent River Naval Air Station, approximately 6.5 miles from Downtown Leonardtown, and only minutes from shopping, restaurants, a movie theater, and grocery stores, this home offers both comfort and convenience in a desirable Hollywood location. **Home is currently tenant occupied, please give as much notice as possible for showings**

25287 Pinto Dr, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
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