Hollywood MD Homes For Sale

Fixer-upper opportunity featuring 3 bedrooms, 2 bathrooms, and a 2-car garage. Set on a desirable, level wooded lot, this property offers a quiet, tree-lined backdrop and plenty of room to roam. Bring your contractor, your design vision, and your imagination to transform this diamond in the rough into a stunning showcase. Sold as-is—bring all offers!

45261 Cuckold Creek Ln, Hollywood

Listing courtesy of Home Towne Real Estate. Contact:

$584,900

4 Beds ⋅ 4 Baths

Welcome to 43618 Albatross Street in the desirable Broad Creek community of Hollywood, MD! This spacious 4-bedroom, 3.5-bath home offers a great blend of comfortable living spaces, attractive finishes, and a private outdoor setting. The main level features a welcoming formal sitting room, a separate dining room for special occasions, and a spacious family room with a cozy gas fireplace. The gourmet kitchen is the heart of the home, offering an oversized center island, plenty of cabinetry, generous counter space, walk in pantry, and an open layout that flows into the family room. Whether you're preparing dinner, hosting friends, or enjoying a quiet night at home, this layout makes it easy to stay connected. Upstairs, the spacious primary suite offers a relaxing retreat, complete with an en-suite bathroom featuring dual vanities, a soaking tub, a large tiled walk-in shower, and ample closet space. The additional bedrooms offer flexibility for family, guests, or a home office. The finished lower level provides even more room to spread out, with a large recreation room featuring new carpet and fresh paint, a full bathroom, and a versatile bonus room that can serve as an office, workout room, hobby space, or guest area. Step outside to enjoy the screened-in deck overlooking the peaceful, wooded backyard. The vinyl privacy fence and mature trees create a private setting for morning coffee, outdoor dining, or relaxing at the end of the day. With generous living space, a flexible floor plan, and a private outdoor retreat, this home has plenty to offer. Broad Creek is conveniently located near schools, shopping, restaurants, and local amenities, with easy access to PAX NAS. Come see all that 43618 Albatross Street has to offer and imagine making it your next home!

43618 Albatross St, Hollywood

Listing courtesy of EXP Realty, LLC. Contact:

$499,999

3 Beds ⋅ 3 Baths

Under Construction. Expected completing date is Nov 30. NO School Excise Tax! Floor Plans have been uploaded. All finishes for this unique home have already been selected. Professional Photos coming soon. Front of the home will showcase Board & Batten vinyl siding, black framed Double-Hung, Low-E windows, a 6x24' covered front porch with black metal roofing. Rear and sides of the home with Vinyl Lap Siding and 6x8' patio. 30 Year Architectural Shingle Roof. Interior of the home will include Luxury Vinyl Plank on the entire main level which includes 9ft ceilings, foyer with coat closet, an expansive eat-in gourmet kitchen with high quality cabinetry, SS appliances, upgraded countertops, center island and designated pantry, dining area, nearby living room, laundry room, half bath and access to the 2 car garage. The second level includes a spacious Primary Bedroom with Tray Ceiling, carpet flooring and Ensuite that includes LVP flooring, dual vanities, a walk-in shower with tile surround, plus a walk-in closet. Two additional bedrooms will have carpet flooring and a second full bath with LVP flooring, tub/shower combo and custom tile surround. Builder warranties include: 10 Year Structural Warranty, 2 Year Manufacturer Warranty

24931 Sotterley Rd, Hollywood

Listing courtesy of RE/MAX One. Contact:

$44,900

DISCOVER THIS .71 ACRE LOT AVAILABLE IN SOUGHT AFTER FENWICK MANOR COMMUNITY WITHIN SAINT MARY'S COUNTY. ZONING RNC. DRIVE BY TODAY TO DETERMINE FOR YOURSELF HOW IT CAN WORK FOR YOUR NEEDS! OWNER FINANCING AVAILABLE.

25106 Pinto Dr, Hollywood

Listing courtesy of Taylor Properties. Contact:

$499,000

3 Beds ⋅ 3 Baths

Coming soon to the market

24407 Three Notch Rd, Hollywood

Listing courtesy of The Southside Group Real Estate. Contact:

$745,000

5 Beds ⋅ 4 Baths

Modern Colonial on 3.8 wooded acres minutes to NAS Pax River with easy access north! Built 2004, this 5BR/3.5BA home features a finished walk-out basement with full bath & 5th bedroom. Updated kitchen with new appliances, LVT flooring, granite countertops & gas range. Updated HVAC, new deck, and upgraded Pella windows and Patio doors. Insulated 36'x28' detached garage/workshop with water & electric and plenty of exterior parking for RV's, tractors, etc. Whole-house generator hookup with transfer switch & integrated breaker panel. 240 ft of road frontage with two driveway entrances and a large private backyard. Leonardtown school system. Just 7 minutes to St. Mary's Hospital, 4 miles to Southern Maryland College, and 0.2 miles to Hollywood Fire Rescue. Convenient to shopping, dining & fishing from Solomons Island. Near Amish farms with fresh produce year-round. Well-maintained property located in quiet neighborhood—seller downsizing to travel more.

25125 Pappys Way, Hollywood

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$429,900

3 Beds ⋅ 2 Baths

Investor opportunity situated on approximately 3 acres in Hollywood, Maryland. Detached one-level ranch-style dwelling offering approximately 1,288 square feet of living area, with additional exterior improvements and outbuildings. Property is being sold strictly AS-IS, WHERE-IS, with seller making no repairs or representations regarding condition. Interior access has not been available, and property characteristics have not been independently verified. Buyer responsible for all due diligence. DO NOT DISTURB OCCUPANTS. NO TRESPASSING OR UNAUTHORIZED ACCESS TO THE PROPERTY. No interior inspections or showings permitted at this time. All offers subject to seller approval.

24948 Sotterley Rd, Hollywood

Listing courtesy of Metro DMV Realty. Contact:

$110,000

0.72-Acre Wooded Lot for Sale in Hollywood, MD. Explore the possibilities with this 0.72-acre vacant lot located on Raspberry Lane in Hollywood, St. Mary's County, Maryland. Offering approximately 31,363 square feet of land and 103 feet of road frontage, this property presents an opportunity for buyers and investors looking to secure land in Southern Maryland. The property is zoned RPD and features a wooded, sloping landscape with natural surroundings. Well and septic systems will be needed, allowing prospective buyers to investigate suitable options based on site conditions and local requirements. Whether you're considering a future homesite or looking for a land investment, this parcel provides space to explore your plans in the Hollywood area.

Raspberry Ln, Hollywood

Listing courtesy of Beycome Brokerage Realty LLC. Contact:

$749,000

4 Beds ⋅ 4 Baths

Nestled in the sought after Forrest Farm community, this exquisite brick front Colonial home offers a harmonious blend of luxury and comfort. Spanning over 5,196 square feet, this residence is designed for both entertaining and everyday living. Hardwood flooring welcomes you home and flows throughout much of the first floor. The open floor plan invites you into a sun-drenched family room, complete with a cozy gas fireplace, perfect for intimate gatherings or quiet evenings at home. The gourmet kitchen is a chef's delight, featuring an expansive island, ample table space, and a convenient pantry, ensuring culinary adventures are both enjoyable and effortless. Adjacent to the kitchen, the formal dining room, with elegant crown moldings, sets the stage for memorable holiday meals. Retreat to the primary suite, where a spa-like bathroom awaits. Newly renovated, this luxury space boasts a beautiful tiled shower, new dual vanities and a large soaking tub with tile surround. The primary bedroom is generously sized with additional sitting space. A walk-in closet rounds out this large private owners getaway. Each additional bedroom is thoughtfully designed with generous closets, providing comfort and privacy for all. The fully finished walkout basement offers endless possibilities, whether as a recreation area, a private retreat with ample storage or flexible living space. The backyard is home to a large maintenance free deck, cozy fire pit, garden boxes and a handy storage shed--all backing to woods for privacy and tranquility. Outside, the community amenities, including a pool, tennis courts, and basketball courts, enhance the lifestyle of leisure, recreation and convenience. With a side-entry garage and a sprawling 2.2-acre lot, this home combines elegance with practicality. Experience the perfect blend of luxury living and community charm in this remarkable property. Updates include fresh paint throughout, updated lighting and fixtures, kitchen counters and refreshed bathrooms including the fully updated primary bath. Additionally, the yard also has been equipped with an invisible dog fence. The hvac was recently serviced and provides additional peace of mind. Don't miss the opportunity to make this lovely turn-key home your own!

23381 Tara Ln, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact:

$405,000

2 Beds ⋅ 2 Baths

Discover the charm of this delightful ranch-style home nestled in the sought-after Hollywood community. Less then 10 miles from Patuxant Navel Air Station, and Leonardtown, With 2 spacious bedrooms and 2 full bathrooms, this residence offers a perfect blend of comfort and functionality. Step inside to find an inviting layout adorned with engineered wood floors, crown moldings, and recessed lighting that create a warm ambiance throughout. The eat-in kitchen features an island, ideal for casual dining, while the formal dining room sets the stage for memorable gatherings. Cozy up by the propane fireplace in the living area, framed by a brick hearthand a classic mantel, perfect for those chilly evenings. Set on a generous 1.03-acre lot, this property backs onto an open common area, providing a serene backdrop of trees and woods. Enjoy the tranquility of nature right in your backyard, complemented by a detached garage and ample off-street parking. The Hollywood community is renowned for its friendly atmosphere and convenient access to local amenities. Residents benefit from nearby parks, excellent schools, and public services that enhance the quality of life. With an airport less than 2 miles away, travel is a breeze. This home is not just a place to live; it's a lifestyle choice that offers peace, community, and the beauty of nature. Don't miss the opportunity to make this charming residence your own!

44372 Clarkes Landing Rd, Hollywood

Listing courtesy of Taylor Properties. Contact:

$669,000

4 Beds ⋅ 3 Baths

Discover the perfect blend of comfort and tranquility in this stunning, custom built split-level home nestled in Hollywood. With 4 spacious bedrooms and 2.5 bathrooms, this residence offers ample space for relaxation and entertainment. The kitchen is equipped with modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven/range, and brand new LG Thin Q series refrigerator that makes craft ice! Step into the inviting living space complemented by vaulted ceilings. The fourth bedroom and half bath help round out the main level. The primary suite boasts a remodeled bathroom featuring a luxurious tiled shower and a generous walk-in closet, providing a private retreat. Two additional bedrooms upstairs share another beautifully renovated bathroom. Set on a sprawling 3.69-acre lot that backs to lush trees and features a 30x36 barn, this property provides a peaceful escape from the hustle and bustle of everyday life. Enjoy the beauty of nature right from your backyard, perfect for outdoor activities or simply unwinding in a tranquil setting. The side-entry garage and expansive driveway offer plenty of parking for guests, and includes a 50 amp hookup for an RV. This home combines the charm of country living with convenient access to nearby amenities. Experience the perfect balance of space, comfort, and nature. Don't miss your chance to make this lovely home yours!

25255 Vista Rd, Hollywood

Listing courtesy of O'Brien Realty ERA Powered. Contact:

$1,450,000

3 Beds ⋅ 3 Baths

Welcome to this stunning custom waterfront home, situated high on Half Pone Point, offering elegant living on the St. Mary’s side of the Patuxent River. Built in 2014, this well-maintained property features quality workmanship throughout its approximately 4,500 square feet of above-grade living space. The bright and open interior features a first-floor owner's suite, spacious secondary bedrooms upstairs, and a large upper-level craft/media room. The main level offers 9' ceilings, hardwood floors, a dedicated office, dining room, and an inviting family room with a coffered ceiling, adjacent to a tile-floored sunroom to capture coastal scenery all year, complete with an indoor porch swing. The main-level primary suite boasts elegant tray ceilings and three expansive walk-in closets. The spa-like primary bath features a heated floor, a separate walk-in shower, dual vanities, a private water closet, and a luxurious two-person whirlpool tub, with convenient direct access to the spacious laundry room. The chef-inspired gourmet kitchen features stunning granite counters, custom 42" cabinetry, and a full suite of professional stainless steel appliances. Culinary enthusiasts will appreciate the gas cooktop with a dedicated pot filler and the large corner pantry. Transition seamlessly to the unparalleled outdoor oasis, designed for grand entertaining. The 14x20 composite deck features sleek glass railing panels for unobstructed views and a retractable awning for shade. Below, a hardscape patio defines a comfortable conversation area centered around a remote-controlled gas fire pit—ideal for enjoying cool coastal evenings. This is the epitome of coastal living, defined by exceptional waterfront amenities: 100 feet of private Patuxent River frontage, complete with a 290-foot pier and boat lift, providing effortless deep-water access to the Chesapeake Bay and stunning, direct views of the iconic Solomons Island Bridge. Ample storage and flex space abound, including an oversized 3-car garage, a dedicated RV pad, and a 16x10 Amish-built shed. The unfinished walk-up basement offers vast potential, complete with built-in shelving, a workbench, a convenient half bath, and an exterior entrance. Modern systems ensure year-round comfort and peace of mind, including a dual-zone HVAC system (heat pump with gas furnace backup) and a ready-to-use home generator. Built for enduring resilience and convenience, the home features durable HardiePlank siding and 30-year Timberline architectural shingles. Short commute to NAS Pax River, home of the US Naval Test Pilot School. Embrace the Southern Maryland lifestyle with immediate access to recreational boating, fishing, and crabbing. Explore nearby historic towns—Solomons, St. Mary’s City, and Leonardtown—offering fine dining, seasonal concerts, and festivals. It's your turn to claim this luxury retreat and coastal charm, entertaining friends and family along the picturesque shores of the Patuxent River.

24814 Half Pone Point Rd, Hollywood

Listing courtesy of RE/MAX One. Contact:

$59,000

BUILD YOUR FUTURE IN HOLLYWOOD! 🌳 Opportunity awaits on this 1-acre vacant lot on Lawrence Hayden Road in Hollywood, St. Mary’s County, Maryland. Whether you're looking to build your dream home, create a private retreat, or secure land for future investment, this property offers an opportunity to own a piece of Southern Maryland in an established residential area. Located along Lawrence Hayden Road, the property offers a convenient location with easy access to surrounding communities, shopping, dining, schools, employment centers, and major routes throughout St. Mary’s County. The area includes established residential properties on 1-acre parcels, creating a desirable setting for those looking for space and privacy while remaining close to everyday conveniences. Public records for nearby properties in the Lawrence Hayden Road area indicate private sewer service, and residential parcels in the immediate area include properties with RPD — Rural Preservation District zoning. Buyer should independently verify the exact zoning, permitted uses, sewer availability, road access, and development requirements for this specific parcel with St. Mary’s County. PROPERTY HIGHLIGHTS: • Approximately 1 Acre • Vacant Land • Lawrence Hayden Road location • Hollywood, St. Mary’s County, MD • Residential setting • Convenient access to major routes and area amenities • Opportunity for a custom home or land investment • Buyer to verify utilities and development potential Bring your builder and explore the possibilities! Whether you're ready to build now or looking for land to hold for the future, this property deserves a closer look.

Lawrence Hayden Road, Hollywood

Listing courtesy of Samson Properties. Contact:

$295,000

3 Beds ⋅ 2 Baths

Updates abound! This home has a new 2 year old roof, 1 year old hot water heater, and 1 year old oil HVAC system. And the updates don't stop there. New carpet, fresh paint and beautiful primary bath. Nestled on a generous 0.88-acre lot and offering a wonderful combination of comfort, space, and recent updates. Step inside to find a thoughtfully designed split-bedroom layout featuring three well-appointed bedrooms and two full bathrooms, providing ample space for both relaxation and privacy. The heart of the home is a welcoming living area that invites you to unwind and create lasting memories. The interior offers a blank canvas with plenty of possibilities for personalization, allowing you to bring your own style and vision to the space. The exterior of the property is equally appealing, with a detached garage approximately 24' x 27' and a shed approximately 12' x 24'. Plenty of additional storage space for tools, outdoor equipment, and seasonal items. The expansive 0.88-acre lot offers plenty of room for outdoor activities, gardening, entertaining, or simply enjoying the peaceful surroundings. Whether you envision summer barbecues, a garden retreat, or simply having room to spread out, the possibilities are plentiful. Conveniently located with easy access to local amenities while still offering a sense of seclusion, this property provides the freedom to enjoy your home and land without association fees or restrictive community rules. This home offers a wonderful opportunity to make it your own.

24625 Hollywood Rd, Hollywood

Listing courtesy of Leonard Realty, Inc.. Contact:

$459,900

3 Beds ⋅ 2 Baths

Discover the charm of this beautifully maintained split foyer home in the desirable Gillens Grove community. Built in 1978, this residence offers a perfect blend of classic design and modern comfort, featuring 1,664 sq. ft. of finished living space. With three spacious bedrooms and two full bathrooms, this home is designed for both relaxation and functionality. The fully finished basement provides additional living space, ideal for a family room, home office, or recreational area. The brick and combination exterior not only enhances curb appeal but also ensures durability. Enjoy the convenience of an attached front-entry garage with space for two vehicles, complemented by a paved driveway that accommodates up to four additional cars. Set on a generous 0.72-acre lot, the property offers ample outdoor space for gardening, entertaining, or simply enjoying the tranquility of your surroundings. This home is perfect for those seeking a peaceful retreat while remaining close to local conveniences. Close to PAX River work sites, shopping and great schools in the area. Don’t miss the opportunity to make this charming property your own! Schedule a showing today and envision the possibilities that await in this inviting space. Home Warranty Provided with the sale of the home.

42544 Anne Ct, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact:

$989,000

4 Beds ⋅ 6 Baths

Some properties are defined by the home, others by the land, and some by the water... 44742 Three Coves Road is one of those rare places where you truly get it ALL. Set on 3.4+ acres of flat and private land with 256 ft of deep-water frontage on a protected cove off Cuckold Creek, this custom brick estate offers over 5,800 sqft of living space, a 2-stall horse stable, multiple garages, and a private pier with electric and plumbing. Just minutes by boat to the Patuxent River, Chesapeake Bay, Solomons, and the surrounding area, this is Southern Maryland waterfront living at its best. Inside, a spacious foyer welcomes you before opening to the family room, where panoramic water views through the sunroom immediately steal your attention. Fireplaces on every level give this expansive home a special sense of warmth and character. The oversized kitchen was designed for real life with dual wall ovens, cooktop, indoor grill, spacious pantry, and seemingly endless counter and storage space. A bright breakfast nook is perfect for casual meals, while the nearby mudroom and full bath add rarely found functionality. Formal living and dining rooms provide plenty of space for hosting holidays and special gatherings. The main-level primary suite creates a private retreat with walk-in closets, full ensuite, and its own balcony overlooking the water. Upstairs, an additional gathering room connects the spacious bedrooms. A second primary suite features another walk-in closet and private ensuite, while the hall bath offers dual vanities for streamlined mornings. Notice all of the incredible storage rooms as you continue through the den before reaching the private in-law apartment above the garage (complete with its own bedroom, full bath, kitchen, and living space... perfect for extended family or guests). Downstairs, wide-open spaces are ready for entertaining, game nights, celebrations, or simply spreading out. A full bathroom, storage cellar, dedicated workshop, and additional storage complete the level, while the walkout leads directly to your patio and backyard. Outside is where this property truly becomes something special. Multiple decks and gathering spaces overlook the cove, including a "party platform" already wired for a hot tub. Follow the steps or path toward the shoreline to your private pier and small sandy area tucked along the water. Deep-water access allows you to keep most any boat right at home while enjoying the protection and tranquility of the cove. Spend your days lounging on the pier, tubing or waterskiing, cruising the Patuxent and Chesapeake, catching a sunset, or simply hopping in the boat and heading to dinner. Back on land, the 3.4+ acres are flat, private, and incredibly usable. The horse stable offers generous additional storage spaces, garages, workshop, large driveway, and flexible living spaces make this estate as functional as it is impressive. 44742 Three Coves Road isn't simply a waterfront home. It's a place for horses and boats, holidays and summer weekends, extended family and overnight guests, quiet mornings overlooking the cove, and long evenings spent on the water. This is your opportunity to create a truly one-of-a-kind Southern Maryland waterfront retreat. *Well maintained * Generator to convey

44742 Three Coves Rd, Hollywood

Listing courtesy of RE/MAX One. Contact:

$319,900

3 Beds ⋅ 1 Baths

Welcome home to 24861 Three Notch Road! This beautifully updated rambler offers seamless one-level living, modern upgrades, and the perfect blend of convenience and country charm. Step inside to discover a bright and inviting layout featuring a fully renovated kitchen equipped with updated cabinetry, sleek countertops, and modern finishes—ideal for daily living and entertaining. The functional floor plan includes three bedrooms and an updated full bathroom. Outside, enjoy the expansive 1-acre lot offering endless space for outdoor activities, gardening, or relaxing in your own private sanctuary. Unbeatably located in Hollywood, MD, you are just minutes from NAS Patuxent River, local shopping, dining, parks, and major commuter routes. Move-in ready —schedule your private tour today!

24861 Three Notch Rd, Hollywood

Listing courtesy of Home Towne Real Estate. Contact:

$169,990

VERY Nice Lot - Ready for you! Build your dream home. Lot has been perced and ready for you. Buyer responsible for verifying and checking all information on the lot. Do Not Wait.

42262 Broyhill Ln, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact:

$799,000

5 Beds ⋅ 3 Baths

17.5 Acres on Cuckold Creek. Rare large waterfront property of 17.5+ acres to provide you peace, quiet and privacy on highly desired Cuckold Creek. The 17.5 acres are mostly level and heavily wooded with walnut, Cypress, Maple, Oak and pine . Wildlife abounds. The Hickory Landing community dock on the property will have your own boat slip. A large garden plot is right on Hickory Landing Way, but tucked way down a beautiful long and winding driveway, you find the house on the water. Originally built in 1983, the house takes full advantage of the extraordinary water view of Cuckold creek with soaring cathedral ceilings of exposed beams and 2"x4" tongue and groove. The addition from mid 90's also takes full advantage of the extraordinary water views with dozens of Anderson window casement windows in excellent condition. The property contains a solid one room cabin with wood stove for you to use your imagination with. New standing seam metal roof put on the cabin in 2022. New 10'x14' outbuilding with 8'doors placed on the property this summer. Property sold as-is, however numerous improvements made this year, You could be waiting a very long time before another property like this comes to market. Please call listing agent for more information.

44908 Hickory Landing Way, Hollywood

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$144,900

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

25611 Clover Hill Rd, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact:

$29,900

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:

$724,986

3 Beds ⋅ 4 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:

$1,299,000

4 Beds ⋅ 3 Baths

Nestled on the shores of the Patuxent River is this very private, custom-built, all brick home. Beautiful hardwood flooring throughout, modern kitchen and baths, a family room with fireplace and built-ins all situated on 5 sprawling acres. The property boasts 402 feet of riprapped shoreline. Old growth trees grace the circular driveway. The grounds have been professionally landscaped with a sprinkler system installed. For the outdoorsman, there is a 4 stall horse barn, an enclosed dog run and more. Enjoy nature's beauty on the water; conveniently located in North Hollywood 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:

$434,900

3 Beds ⋅ 2 Baths

Welcome home to this beautifully renovated rambler located in the desirable Gillens Grove community of Hollywood, Maryland! This charming 3-bedroom, 2-bath home has been thoughtfully updated! Step inside to stunning hardwood floors that flow throughout the spacious, open-concept living area. The bright and inviting kitchen features gorgeous 42-inch cabinetry, stainless steel appliances, ample counter space, and a beautiful bay window that fills the home with natural light. The recent renovations throughout the home provide modern comfort while maintaining timeless charm. Don't miss your opportunity to own this exceptional home—priced to sell and expected to go quickly. Schedule your private showing today before it's gone! The roof was upgraded in 2020, offering added peace of mind for years to come. HOME IS BEING SOLD AS-IS. SELLER TO PAY SOME CLOSING COSTS.

25397 Allston Ln, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact:

$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:

$149,900

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 Ct, Hollywood

Listing courtesy of Franzen Realtors, Inc.. Contact:

$4,295,000

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:

$175,000

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 access or improvements with the county.

Ewell Lane, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact:

$459,900

3 Beds ⋅ 2 Baths

Rate reduction potential! Motivated seller! 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 main ONE level living, this may be what you're looking for. Unfinished walk up/out basement with french drains, centrally located in Hollywood less than 1500 feet from Dorsey Park. Close proximity to downtown walkable Leonardtown, hospital, shopping, and schools.

24301 Old Hollywood Rd, Hollywood

Listing courtesy of RE/MAX One. Contact:

$275,000

3 Beds ⋅ 2 Baths

23955 Hollywood Rd, Hollywood

Listing courtesy of Real Broker, LLC. Contact:

$100,000

Located in Saint Mary's county, where you will find lots of rolling hills and land. This 2.17 acre lot offered in the Sotterley Manor neighborhood could be just what you are looking for. Although it has it's bumps and bruises it offers the seclusion you desire the most. If you are looking to build a private oasis within a neighborhood of estate homes, this would be the spot to do so. Not far from shopping, schools and everything you may desire for entertainment. Find your custom builder and start planning. Electricity already available.

25675 Southwell Ln, Hollywood

Listing courtesy of AMR Elite Realtors, LLC. Contact:

$1,300,000

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, 10 miles from Patuxent River Naval Air Station/NAWCAD, less than one hour to DC/Northern Virginia. The Villages at Clarks Mill The property currently has a Concept Plan for 18 townhome units approved by the St. Mary’s County Planning Commission and public water and sewer category update completed to include this parcel. The project includes a playspace, additional parking and landscaping. There is an available .5 acre adjoining lot for consideration to expand the project. Build the first townhome subdivision in the Hollywood Town Center. This carefully planned community is innovative for the area and uniquely offers close proximity to amenities with easy access onto Mervell Dean Rd. (a County road with no traffic improvements required), is a refreshing break from the larger subdivisions and retains plenty of green space. Documentation, which is available for public download in the DOCUMENTS TAB, contains: SDAT reports for each of the 5 addresses within the parcel 613, an economic information fact sheet for the area, property plat and site plan drawings, the Concept Development Plan and pertinent County documents. A private meeting with the current owner/developer to discuss many options and available insights into the potential build-out can be scheduled with qualified purchaser parties. In addition, a Comparable Sales Package is available to support sales prices for these units in the $400-500K price range.

44405 K & R Way, Hollywood

Listing courtesy of Samson Properties. Contact:

$306,900

3 Beds ⋅ 1 Baths

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.

24040 Hollywood Rd, Hollywood

Listing courtesy of Coldwell Banker Premier. Contact:

$175,000

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, residential dwelling, garage, pole barn, day care facility, medical office, or church—this versatile property invites creativity and investment. Its convenient location provides quick access to the airport and commuter services, making it perfect for both personal and commercial needs. Don’t miss this unique chance to secure well-situated land in a rapidly growing area of St. Mary’s County!

Saint Johns Road, Hollywood

Listing courtesy of CENTURY 21 New Millennium. Contact:

$125,000

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 development. Buyers are encouraged to explore septic possibilities for seamless construction.

24984 Sotterley Rd, Hollywood

Listing courtesy of Home Towne Real Estate. Contact:

$399,000

3 Beds ⋅ 2 Baths

JUST REDUCED $100,000.00 WHAT A DEAL = HOME NEEDS SOME WORK = IT'S AN INVESTORS DREAM REMODLE AND SELL IT AND MAKE SOME MONEY= VACANT = WATERFRONT ON COLES CREEK.

26188 Skyview Dr, Hollywood

Listing courtesy of Elrod & Associates Real Estate, Inc. Contact:

Hollywood MD Homes For Sale

Hollywood MD Homes For Sale

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