Hollywood Real Estate

Hollywood Real Estate

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Newest Listings in Hollywood

3 Beds ⋅ 3 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

4 Beds ⋅ 4 Baths

Welcome to your own private paradise in the highly sought-after Hollywood area, tucked away off peaceful McIntosh Road. Set on nearly 16 scenic acres, this exceptional property offers the perfect blend of luxury, privacy, recreation, and modern convenience. A beautifully landscaped entrance welcomes you home with River Birch, Japanese maples, butterfly bushes, roses, azaleas, hostas, and manicured boxwoods, creating breathtaking curb appeal from the moment you arrive. A spacious paved circular driveway provides effortless access for RVs, boats, trailers, and additional vehicles, making entertaining and everyday living equally convenient. The 3,400-square-foot home features 4 bedrooms, 3.5 bathrooms, an attached two-car garage, and a thoughtfully designed open floor plan enhanced with extensive Apple HomeKit smart home automation. Ring security cameras, lighting, HVAC controls, and garage doors can all be monitored and controlled remotely from your smartphone, offering exceptional comfort, convenience, and peace of mind. The main level is designed for easy living and entertaining, featuring a spacious living room with a cozy gas fireplace, a dedicated home office, powder room, and a luxurious primary suite complete with a walk-in closet with custom built-ins and an en-suite bath featuring dual vanities and a walk-in shower. The gourmet kitchen is the heart of the home, showcasing granite countertops, abundant cabinetry, under-cabinet lighting, a six-seat center island, breakfast area, newer French-door refrigerator, dishwasher, five-burner propane cooktop, and wall oven. The fully finished walk-out lower level expands the home's versatility with three additional bedrooms, two full bathrooms, a large family room/man cave, and a second office—ideal for guests, multi-generational living, or working from home. Outdoor living is equally impressive. A paver walkway leads to a stamped concrete patio that flows seamlessly onto an expansive deck, creating the perfect space for grilling, outdoor dining, and entertaining family and friends. The impressive 40' x 36' (1,440 sq. ft.) Amish-built pole barn, completed in 2022, is a standout feature. Offering two oversized 12' x 12' garage bays with Wi-Fi-enabled openers, it easily accommodates vehicles, boats, small RVs, tractors, or recreational equipment. The barn also includes a built-in workbench, storage racking, and a ceiling lift system for Jeep or Bronco hardtop removal and storage—all conveying with the property. Dedicated RV parking with 50-amp electrical service adds even more convenience. An additional storage shed, built in 2020, provides ample space for lawn equipment and outdoor tools. The property itself is a nature lover's dream. Once part of a historic farmette, it offers established ATV trails, wooded privacy, and stretches nearly to McIntosh Run. Wildlife is abundant, with deer, wild turkey, and other native species frequently visiting, making this an ideal retreat for sportsmen, outdoor enthusiasts, or anyone seeking peaceful country living without sacrificing modern amenities. Additional highlights include a new high-efficiency HVAC system installed in 2026, featuring a 20-SEER heat pump, new indoor coil, and propane furnace for supplemental and emergency heating. Whether you're searching for a private family retreat, an outdoor recreation haven, or a property with exceptional space for hobbies and equipment, this one-of-a-kind estate offers endless possibilities. Opportunities like this are rare—schedule your private showing today and experience everything this extraordinary property has to offer.

42000 Pleasant Valley Ct, Hollywood

Listing courtesy of RE/MAX One. Contact: 4437718009

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

Vacant parcel around 1/4 acre in size in Hollywood Shores. Call Listing Agent with questions. Photos to be posted soon.

26457 Peninsular Dr, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500

Over an acre that has been perced at the intersection of Clover Hill Rd. and McIntosh Rd. Call listing agent with questions. Photos to be posted soon.

25611 Clover Hill Rd, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500

4 Beds ⋅ 3 Baths

Coming Soon! Nestled on over 3 private acres in the heart of Hollywood, Maryland, this beautifully maintained 4-bedroom, 3-bath rambler offers the perfect combination of peaceful country living and modern convenience. Enjoy the ease of one-level living with a thoughtfully designed floor plan featuring main-level laundry, a spacious open-concept layout, and a large kitchen complete with granite countertops, stainless steel appliances, and abundant cabinet space. The fully finished basement significantly expands the home's living space and has been recently updated with new luxury vinyl plank flooring and fresh paint, creating the perfect area for entertaining, a recreation room, home office, or guest accommodations. Recent updates throughout the home, combined with the exceptional level of care it has received over the years, make this property truly move-in ready. Outside, you'll appreciate the expansive yard, mature trees, and private setting that provide plenty of space to relax, entertain, or simply enjoy the outdoors. Despite its tranquil rural atmosphere, this home is located just minutes from downtown Leonardtown, offering convenient access to shopping, restaurants, schools, parks, and local events. If you've been searching for a spacious, meticulously maintained home with acreage, privacy, and an unbeatable Southern Maryland location, this one is not to be missed. Professional photos and additional details coming soon!

24490 Oak Valley Ln, Hollywood

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636

3 Beds ⋅ 1 Baths

26260 Skyview Dr, Hollywood

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

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

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

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 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

The lot is located in a well-established, sought-after area of Hollywood, a quiet, secluded, wooded lot. walking distance to Greenwell State Park.Great for the person who likes to walk and jog. Across from a currently farmed field. Conveniently located near the County's Forrest Landing boat ramp to Cuckel Creek, launch your boat or kayaks There is an approved perk for the site. Approximately 15 minutes to Wildewood, quick trip to the base.

45025 Nolan Court, Hollywood

Listing courtesy of Franzen Realtors, Inc.. Contact:

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