Discover Hollywood with
The Southside Group

Hollywood is a rural St. Mary's County community stretching from Route 235 east to the Patuxent River. Creeks, coves, and river frontage give many homes a water view or a pier, while inland roads offer wooded lots and farm land. Historic Sotterley and Greenwell State Park are both right here.

Local Insights

We help buyers compare Hollywood homes by water access, pier and shoreline details, flood zone, well and septic, and the drive to the base, so you can focus on the right homes before you tour.

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Homes for Sale in Hollywood, MD

  • About Hollywood, MD

    Aerial view of a creek winding into the Patuxent River in Hollywood, Maryland

    Hollywood is an unincorporated community in St. Mary's County, and addresses use ZIP code 20636. It sits between Route 235 and the Patuxent River, north of California and east of Leonardtown.

    The name dates to 1867. The post office inside Thompson's general store, near the Uniontown part of Hollywood, needed a name, and the community borrowed it from the large holly tree planted in front of the store. It has nothing to do with the movie town in California.

    Hollywood, MD is centered on the crossing of Routes 235 and 245, and smaller settlements such as Winter Seat and Land O' Lakes sit just north of it.


    Sotterley, a plantation site on the Patuxent dating to 1703, is now a museum that tells the full history of the people who lived and worked there, including those who were enslaved.

    Greenwell State Park, also on the river, offers trails, horseback riding, and river access. Many residents commute to Naval Air Station Patuxent River, a short drive south.


    Waterfront Homes
    Patuxent River
    Historic Sotterley
    Greenwell State Park
    Rural Lots
    Near Pax River NAS


    Hollywood Real Estate

    Hollywood offers a mix of waterfront and rural homes. Here is a general picture of what buyers usually find.



    Waterfront homes sit along the Patuxent River and creeks that feed it. Some have piers, boat lifts, or deep water, but every shoreline is different.


    Inland homes include ranchers, colonials, and custom homes on wooded lots, plus some subdivisions near Route 235.


    Farm properties and land come up for sale on the quieter back roads.


    Hollywood is unincorporated, so homes pay St. Mary's County and state property taxes only.


    Waterfront prices vary widely with frontage, water depth, and pier condition. Ask us for recent sales near the homes you like.

    Single-Family
    Homes
    Townhome
    Options
    Condominium
    Living
    Varied
    Home Styles
    Waterfront home with a private pier on a creek in Hollywood, Maryland


    Hollywood Residential Sections

    Patuxent Riverfront

    Homes with direct river frontage and wide views.

    PROPERTY TYPES
    Waterfront single family homes; check pier permits, water depth, shoreline, and flood zone.

    Creek and Cove Homes

    Homes along the creeks that feed the Patuxent, often with calmer water.

    PROPERTY TYPES
    Waterfront and water view homes; confirm water access and depth.

    Route 235 Area

    Subdivisions close to shopping and the drive to the base.

    PROPERTY TYPES
    Colonials, split levels, and ranchers; confirm HOA rules where they apply.

    Near Sotterley and Greenwell

    Rural roads close to the historic site and the state park.

    PROPERTY TYPES
    Single family homes and land; check well and septic.

    Farm and Wooded Lots

    Quiet back roads with farms and homes tucked into the trees.

    PROPERTY TYPES
    Farmhouses, homes on acreage, and land; check zoning and perc results.

    Residential section names, property types, and association requirements may vary by listing and legal subdivision. Buyers should confirm each property's subdivision, ownership structure, association documents, fees, and applicable restrictions before purchasing.


    Schools & Education in Hollywood

    Young students in a reading circle with their teacher in a St. Mary's County, Maryland classroom

    Public Schools

    St. Mary's County Public Schools runs the public schools for Hollywood.

    Hollywood Elementary School is in town on Joy Chapel Road, and the nearby middle and high schools are roughly 2 to 5 miles from most Hollywood homes.

    Schools in the Hollywood area include:

    ✓ Hollywood Elementary School
    ✓ Esperanza Middle School
    ✓ Chopticon High School

    The school board redistricted the Hollywood area from Leonardtown High School to Chopticon High School in March 2026, with some current students allowed to stay at Leonardtown. These schools are examples, not guaranteed assignments for every Hollywood address. Buyers should confirm the assigned schools for a specific property with St. Mary's County Public Schools before buying.


    Private and Alternative

    Private and faith based schools are located across St. Mary's County. Contact each school directly for admissions, tuition, and transportation details.


    Colleges

    College of Southern Maryland

    The College of Southern Maryland has a campus in nearby Leonardtown, offering associate degrees, certificates, and workforce training.

    Universities Within Driving Range

    St. Mary's College of Maryland is in southern St. Mary's County, and the University System of Maryland at Southern Maryland is nearby in California.


    Things to Do and Local Lifestyle

    Front porch of a country store in Hollywood, Maryland

    Shopping and Restaurants

    Hollywood has a country store feel, with local shops and restaurants near Route 235. Larger shopping is a short drive south in California and Lexington Park.

    For a sit-down meal, locals point to The Cow and the Fish on Three Notch Road, known for local seafood such as scallops and shrimp.


    Parks and Outdoor Recreation

    Greenwell State Park has trails for hiking, biking, and horseback riding, plus river access. The Patuxent and its creeks are popular for boating, kayaking, and fishing.

    Greenwell State Park covers about 596 acres along the Patuxent River, and it is a good spot to bring a dog.

    Riders on horseback along a wooded trail at Greenwell State Park in Hollywood, Maryland

    Families enjoying a hometown fair near Hollywood, Maryland

    Entertainment and Community Activities

    Sotterley hosts tours, programs, and seasonal events on the river. Local fairs, volunteer fire department events, and church gatherings keep the calendar full.

    Sotterley, at 44300 Sotterley Lane, centers on an 18th-century house on a high bluff over the river. The property dates to 1703 and began as a 2,000 acre plantation.



    Getting Around Hollywood

    Major Roads

    Route 235 (Three Notch Road) runs north toward Mechanicsville and south toward California and Lexington Park. Route 245 connects Hollywood with Leonardtown.

    The two routes cross at the center of Hollywood, MD. From there Route 245 runs west into Leonardtown and east toward the Patuxent River side of the community.


    Nearby Communities

    • California: Shopping and newer homes to the south.
    • Leonardtown: The county seat to the west.
    • Mechanicsville: Farm country to the north.
    • Lexington Park: The base town to the south.
    • Solomons: A waterfront town across the Patuxent.
    • Charlotte Hall: A northern crossroads with a farmers market.

    Commuting and Employment

    Naval Air Station Patuxent River is a common commute. Test your drive at the times you would really travel.

    Hollywood sits north of California and Lexington Park, so the drive to the base depends on which part of Hollywood, MD the house is in. Try the route from the actual address before you decide.


    Public Transportation and Airports

    St. Mary's Transit System (STS) runs local routes. St. Mary's County Regional Airport in California serves private planes. Reagan National, BWI Marshall, and Dulles are within driving range.


    Why Buy a Home in Hollywood?

    1. Patuxent River Living

    Many homes have river or creek frontage, and the Patuxent, Cuckold Creek and Broad Creek are all part of the local waterfront search.


    2. Room to Breathe

    Wooded lots and farm land fill the back roads. Compared with California, Hollywood, MD usually offers larger parcels and more rural roads, and buyers who want even more open land sometimes also look north in Mechanicsville.


    3. History Next Door

    Sotterley sits right on the river and dates to 1703. The community itself goes back to 1867, when it was named for a holly tree.


    4. State Park Trails

    Greenwell State Park offers hiking and horseback riding on about 596 acres along the Patuxent.


    5. Close to the Base

    Naval Air Station Patuxent River is a short drive away. Lexington Park sits closer to the base gates, so Hollywood, MD trades a longer commute for less dense surroundings.


    6. Small Community Feel

    Local stores and events keep it close knit. Leonardtown has a defined town center, while Hollywood, MD is more spread out around Routes 235 and 245.


    Frequently Asked Questions About Hollywood, MD

    What county is Hollywood, MD in?

    Hollywood is in St. Mary's County. The name goes back to 1867, when the post office inside Thompson's general store needed a name and the community took it from the large holly tree planted in front of the store.

    What ZIP code does Hollywood use?

    What public schools serve Hollywood?

    Are there waterfront homes in Hollywood?

    What should I check on a waterfront home?

    Do Hollywood homes use well and septic?

    What is Sotterley?

    What is Greenwell State Park?

    How far is Hollywood from Naval Air Station Patuxent River?

    How do I get more information on a Hollywood listing?