Hollywood Homes for Sale

Are you in search of Hollywood, Maryland homes for sale? Look no further! Hollywood MD boasts a charming array of real estate options. With its scenic landscapes and friendly atmosphere, Hollywood MD is the perfect place to call home. Whether you're a first-time buyer or looking to invest in property, our extensive property listings feature a diverse range of residential properties to suit every taste and budget. From quaint houses nestled in quiet neighborhoods to luxurious estates with breathtaking views, Hollywood MD offers something for everyone. Trust THE SOUTHSIDE GROUP, your local realtors to guide you through the home buying process and help you find the perfect investment property in this idyllic Maryland locale.

Included below are homes for sale in Hollywood. If you would like more information on any of these Hollywood real estate listings, just click the "Request More Information" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

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Hollywood Maryland 

Living In Hollywood Maryland

Hollywood Maryland ZIP Code 20636 is a community from Patuxent River to Leonardtown with Highway 235 running north and south through the center of this community intersecting at the heart of the intersection of Highway 245 and 235. There are several smaller communities including winter seat and Land O Lakes, just north of the intersection as well as the Greenwell State Park on the Patuxent River.

This unincorporated community is part of St. Mary's County and was founded back in 1867 when a store owner at Thompson's general store near the Uniontown section of Hollywood required a name for the post office inside the store. No, it's not named for the celebrity-packed Mecca of California, but the gigantic Holly tree planted in front of the store, thus the community was named Hollywood.

Things to do in Hollywood Maryland

This isn't just a little blip on the map; Hollywood Maryland has a variety of fun things to do, places to see, and sites to explore. The Greenwell State Park is one of the premier destinations for anyone in the St. Mary's County area. Nestled on the Patuxent River, a great place to bring your dog. Whether you're hiking, enjoying the river, or just relaxing, this state park is a great destination.

The Cow and the Fish is a local dining favorite located at 251883 Notch Rd. in Hollywood. This unique dining establishment offers fantastic local seafood such as scallops and shrimp. Whether it's a special occasion or a casual lunch, this is one of our favorite places to eat dinner.

The Sotterley Historic Plantation is a unique destination located at 44300 Sotterley Ln. It features an 18th-century house sitting on a high bluff with beautiful views of the river. This is a great destination for learning about the area's history and a fantastic venue for events, weddings, and any occasion. This plantation sits on the hillside overlooking the Patuxent River, originally a 2000 acre property built in 1703.

Hollywood Real Estate

Because this is an unincorporated community, houses are spread out throughout the region but also carry a Hollywood address. Homes are typically priced from $125,000-$800,000 with the median home price being right around $400,000. Whether you looking for acreage, larger homes, fixer-upper's, waterfront property, or homes close to town, you'll find a variety of styles, designs, and ages of homes in Hollywood.

Hollywood Schools

Hollywood is part of the St. Mary's County public school district however, the Hollywood elementary school is located right in town. School-age children are assigned to this elementary school, the Esperanza middle school, and the Leonardtown high school, about 2 to 5 miles from most homes in Hollywood. The high school receives excellent ratings from parents and students alike. Both the elementary and the middle school also received high marks.

"Absolutely love everything about this school. The staff is amazing and the learning environment is above par. Absolutely thrilled my children attend this school" - Niche.com on Hollywood Elementary

Meta Description: Explore Hollywood, MD homes for sale, acreage, waterfront property, Route 235 access, nearby communities and practical buyer guidance.

Is Hollywood, Maryland the right fit for your home search?

Hollywood is worth a hard look if you want to stay close to the California, Lexington Park and Leonardtown corridor but don't necessarily want the more developed setting that comes with living right along the busiest parts of Route 235.

The housing is a big part of the appeal. Current Hollywood real estate can include established single-family homes, newer properties, homes on larger parcels, custom residences and waterfront property. Some roads feel residential. Turn onto another road and you're looking at woods, acreage or tidal water.

That's also why we'd avoid treating "Hollywood, MD" as one type of housing market. Two homes with the same 20636 ZIP code can give you very different lots, road access, utility setups and daily drives.

Trying to decide if Hollywood fits better than California or Leonardtown?

Tell us what you actually want around the house. More land? Waterfront? A subdivision? Quick access to Route 235? A shorter drive toward Leonardtown or NAS Patuxent River?

The Southside Group can help you compare Hollywood with nearby St. Mary's County communities before you start chasing listings that don't fit the way you want to live.

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Quick answers for buyers considering Hollywood, MD

Where is Hollywood, Maryland?

Hollywood is an unincorporated community in St. Mary's County centered around the intersection of Maryland Route 235, also known as Three Notch Road, and Maryland Route 245, or Hollywood Road.

Route 235 connects south toward California and Lexington Park. Route 245 runs west toward Leonardtown and east toward the Patuxent River side of Hollywood.

Is Hollywood close to NAS Patuxent River?

Hollywood sits north of California and Lexington Park, so it regularly comes up in home searches for buyers who need access to NAS Patuxent River but want to look beyond the neighborhoods immediately surrounding the installation.

The tradeoff is property-specific. A Hollywood house may give you a larger lot or a more rural setting, but you'll be driving farther than you would from some Lexington Park or California addresses. Test the route from the actual house before deciding that the extra distance works for you.

What kinds of homes can you find in Hollywood?

Hollywood's current housing mix includes detached single-family homes, established neighborhoods, newer homes, custom properties, acreage and waterfront residences. The live listings also show a pretty broad spread in home size and lot size.

Single-family detached homes make up a significant part of the local inventory. Buyers looking for large condo or townhome selections may find more choices by expanding south toward California and Lexington Park.

Can you find homes with acreage in Hollywood?

Yes. Larger parcels are part of the Hollywood housing mix, and current listings can include properties with several acres. Acreage still needs to be evaluated property by property. More land can mean more maintenance, different driveway access, outbuildings, private utilities or simply more ground than you want to take care of.

Buy the land because you'll use it, not because the listing photo looks good from a drone.

Hollywood gives you several different versions of St. Mary's County living

There isn't a compact Hollywood downtown that defines the whole community. The area spreads from the Route 235 corridor toward wooded residential roads, farms, creeks and the Patuxent River.

That makes the street and lot unusually important here.

Closer to Routes 235 and 245

Living near the main intersection can make it easier to move between Leonardtown, California and the larger Route 235 commercial corridor.

St. Mary's County uses the intersection of Routes 235 and 245 as a major Hollywood reference point in its own driving directions. From there, Route 245 connects directly into Leonardtown, while Route 235 continues toward California and Lexington Park.

If most of your week involves those places, that central access is worth considering.

Farther east toward the Patuxent River

Head east from Route 235 and Hollywood starts feeling different.

Roads around Sotterley, Steer Horn Neck, Clarke's Landing and the surrounding creeks move the search toward larger parcels, wooded settings and water-oriented property.

Greenwell State Park sits in Hollywood along the Patuxent River. Maryland's Department of Natural Resources identifies it as a 596-acre park with trails, paddling, fishing, picnicking and river access. You can review current park information through Maryland DNR.

St. Mary's County also operates Clarke's Landing in Hollywood, with a public boat-launch area and pier facilities. Current launch information is available through the St. Mary's County public landings directory.

Buying waterfront property in Hollywood

Hollywood is one of the St. Mary's County areas where the waterfront search can get interesting.

Properties around the Patuxent River, Cuckold Creek, Broad Creek and other tidal waterways can come onto the market with shoreline frontage, piers or boating access. Current listings show just how different these properties can be, from smaller homes on creek frontage to larger custom properties with acreage.

Waterfront buyers should slow down here.

We'd want to verify:

• actual shoreline frontage
• pier or dock ownership and permits
• water depth and boating access if that matters to you
• shoreline condition
• flood-zone information
• insurance requirements
• septic, well or other private utility details
• Maryland Critical Area considerations that apply to the property

"Waterfront" gets the click. Those details determine what you're actually buying.

Looking for land or waterfront in Hollywood?

Those searches need more than a bedroom and price filter. Tell us how much land you want, whether boating matters, what kind of water access you're expecting and how far you're willing to drive for it.

Ask The Southside Group

Hollywood vs. nearby St. Mary's County communities

Hollywood vs. California

California puts buyers closer to the largest concentration of shopping and commercial services along Route 235. Hollywood generally opens the search up to more rural roads, larger parcels and water-oriented areas while still keeping Route 235 within reach.

If you're deciding between them, don't start with the town name. Start with how much land you want and how often you need to be in the California-Lexington Park corridor.

Hollywood vs. Lexington Park

Lexington Park sits directly beside NAS Patuxent River and puts buyers closer to the base entrances. Hollywood is farther north and spreads into less densely developed areas.

Buyers working around Pax River often include both until they decide how much commute they're willing to trade for the type of property they want.

Hollywood vs. Leonardtown

Leonardtown has a defined town center and serves as the St. Mary's County seat. Hollywood is much more spread out.

If having shops, restaurants and town activity concentrated around a recognizable center matters, Leonardtown deserves a closer look. If your search keeps drifting toward acreage, wooded roads or Patuxent River property, Hollywood may fit better.

Hollywood vs. Mechanicsville

Mechanicsville is farther north in St. Mary's County and also offers rural and larger-lot housing options. Buyers who like Hollywood but don't need to stay as close to California, Lexington Park or Leonardtown may want to push the search farther north and compare both.

Our Where to Live in Maryland guide can help you compare the larger Southern Maryland picture before narrowing the home search.

What should you check before buying a Hollywood home?

The big mistake here is assuming that two Hollywood properties are comparable because the mailing address is the same.

We'd look at the actual property setup:

• Lot and road access. A subdivision lot and a multi-acre rural property require different thinking.
• Well and septic. Confirm what serves the individual house and review the appropriate inspection information.
• Waterfront details. Verify frontage, access rights, piers, shoreline and insurance rather than relying on the listing headline.
• Outbuildings. Check permits, condition and intended use if garages, sheds, barns or other structures matter to you.
• Regular driving routes. Test the drive toward Leonardtown, California, Pax River or wherever you'll actually go.
• HOA requirements. Some Hollywood homes are within associations and others are not.
• School assignment. Confirm it using the exact address rather than an old listing.

Acreage buyers also need to look at the usable portion of the land. Five acres on paper doesn't tell you how the property lays out, where the septic area sits or how much of the land you'll realistically use.

Parks, boating and outdoor access around Hollywood

Hollywood has a genuine connection to the Patuxent River rather than simply being "near water."

Greenwell State Park occupies hundreds of acres along the river and supports hiking, paddling, fishing and other outdoor recreation. Clarke's Landing provides another public access point for boaters.

That doesn't mean every Hollywood house comes with easy waterfront recreation. Some homes sit much closer to these areas than others, and the community covers enough ground that location matters.

If outdoor access is high on your list, map the house against the places you'll actually use.

Schools and Hollywood, Maryland real estate

Hollywood is within St. Mary's County Public Schools, and Hollywood Elementary School is located on Joy Chapel Road.

Don't assume a Hollywood mailing address guarantees a particular elementary, middle or high school. The district operates multiple schools across this part of St. Mary's County, and assignments should be verified for the exact address.

Current district and school information is available directly from St. Mary's County Public Schools.

Selling a home in Hollywood, Maryland

Hollywood sellers have a comp problem if they aren't careful. The housing stock is simply too varied to grab a few nearby sales and call it done.

An acreage property shouldn't be valued like a subdivision house. Waterfront needs another set of comparisons. Outbuildings, pier access, lot utility, home condition and proximity to the main corridors can all change what buyers are willing to compare.

We'd start by separating the home into the right competitive group, then review recent sales and the properties buyers can choose from right now.

And if you own a home with acreage or waterfront, the marketing needs to explain the details buyers can't figure out from the front photo. Lot layout, access, shoreline, pier information and useful outbuildings matter when they're supported and documented.

Homeowners considering a sale can visit our Southern Maryland seller resources or contact The Southside Group Real Estate for a property-specific review.

Looking at Hollywood homes?

Billy Rabbitt and The Southside Group Real Estate are based right here in Hollywood. We can help you compare the Route 235 area, larger-lot properties, waterfront homes and nearby St. Mary's County alternatives based on what you actually want from the property.

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Frequently asked questions about Hollywood, Maryland real estate

Where is Hollywood, MD?

Hollywood is an unincorporated community in St. Mary's County centered around Maryland Routes 235 and 245. Route 235 connects toward California and Lexington Park, while Route 245 connects west toward Leonardtown and east toward the Patuxent River side of Hollywood.

What types of homes can I find in Hollywood, Maryland?

Hollywood real estate can include detached single-family homes, established neighborhood properties, newer homes, custom residences, acreage and waterfront property. Lot size, utility setup, HOA status and property condition vary considerably by location.

Can I find homes with acreage in Hollywood?

Yes. Larger parcels are part of the Hollywood housing market, and acreage properties appear in current inventory. Buyers should evaluate the usable land, access, well and septic setup, outbuildings and maintenance requirements rather than relying only on the acreage number.

Does Hollywood, Maryland have waterfront homes?

Yes. Waterfront and water-oriented properties can be found near the Patuxent River, Cuckold Creek, Broad Creek and other local waterways. Buyers should verify shoreline frontage, dock or pier rights, water access, flood considerations, insurance and applicable permitting for the specific property.

Is Hollywood close to NAS Patuxent River?

Hollywood is north of California and Lexington Park along the Route 235 corridor and is regularly included in searches for buyers who need access to NAS Patuxent River. The actual commute depends on the home's location, traffic and the destination or base gate being used.

How does Hollywood compare with California, MD?

California has a larger concentration of shopping and residential development along Route 235. Hollywood generally offers more opportunity to look at rural roads, larger parcels and water-oriented properties while remaining connected to the same St. Mary's County corridor.

How does Hollywood compare with Leonardtown?

Leonardtown has a defined town center and county-seat setting. Hollywood is more geographically spread out, with residential neighborhoods, wooded parcels, acreage and properties extending toward the Patuxent River.

Does Hollywood have public water access?

Yes. Greenwell State Park is located along the Patuxent River in Hollywood, and St. Mary's County operates Clarke's Landing with boat-launch and pier facilities. Access rules and facilities should be checked with the appropriate government agency before visiting.

What should I check before buying a rural Hollywood property?

Review the lot and access, well and septic information, property condition, outbuildings, easements or restrictions that apply, and the regular drive to the places you'll use. For larger parcels, look at how much of the land is actually useful for what you intend to do.

How do I know which schools serve a Hollywood home?

Hollywood is within St. Mary's County Public Schools, but assignments depend on the exact property address. Buyers should confirm current school zoning directly with the district before using school assignment as part of a housing decision.

Where can I see current Hollywood, MD homes for sale?

Current properties can be viewed directly on the Hollywood homes for sale page. Because inventory changes, live MLS listings are more useful than relying on older price ranges or historical availability.

For more information on Hollywood Maryland real estate, homes for sale, and waterfront property, contact me below. I'd love to help you find the perfect Hollywood MD property for your needs and your budget. Browse available listings above at any time.