St. Mary's County · Southern Maryland
Hollywood, MD
Wooded lots, Patuxent River creeks, and a central St. Mary's location
- Median Price
- $450K
- Typical Range
- $325K – $950K
- Days on Market
- ~22
- To NAS Pax River
- 15 min
Living in Hollywood, MD
Hollywood sits in the center of St. Mary's County along Route 235 and Route 245, between Leonardtown and Patuxent River NAS. Known for wooded residential lots, protected creeks off the Patuxent River, and Greenwell State Park, it offers privacy and water without giving up convenience.
By the Numbers
Real Estate Market Snapshot
Approximate figures for Hollywood, MD, based on recent sales activity. Numbers move; call for a current read on your street.
Median Home Price
Approximately $450,000
Typical Price Range
$325,000 to $950,000
Common Home Styles
Colonials and ramblers on wooded lots, creekside waterfront
Average Days on Market
About 22 days
Annual Appreciation
Roughly 5 to 6 percent
Inventory
Limited; waterfront and larger lots rarely linger
The median home price in Hollywood, MD is approximately $450,000, with most sales between $325,000 and $950,000. Colonials and ramblers on one-acre or larger wooded lots make up the core of the market, while waterfront homes on Cuckold Creek, Mill Creek, and the Patuxent account for the upper end.
Homes typically sell in about 22 days. Appreciation has averaged roughly 5 to 6 percent per year, supported by the area's school assignment and central location. Inventory is limited, and properties with water access or larger private lots rarely stay on the market long.
Day to Day
Community & Lifestyle
What it actually feels like to live in Hollywood, MD, from errands and dinner to weekends on the water.
Shopping
Grocery and essentials at the Route 235 and Route 245 intersection, with the full California retail corridor about ten minutes south.
Dining
Long-standing local restaurants and seafood spots, with Leonardtown's square and California's options each within a short drive.
Parks & Recreation
Greenwell State Park on the Patuxent with trails, a beach, and equestrian access, plus Sotterley Plantation and Myrtle Point Park nearby.
Schools
Served by St. Mary's County Public Schools, with Hollywood Elementary in the community and Leonardtown High School as the typical assignment.
Commuting
About 15 minutes to Patuxent River NAS and roughly 10 minutes to Leonardtown, one of the most balanced locations in the county.
Water Access
Cuckold Creek, Mill Creek, and the Patuxent River provide protected waterfront, private piers, and public launches.
Hollywood feels established and settled. Many homes sit back from the road on wooded lots, and neighborhoods are quiet without being remote. Greenwell State Park offers trails, a river beach, and horseback riding, while Sotterley Plantation hosts farmers markets and events. Boaters appreciate the protected creeks that open onto the Patuxent River.
Shopping and dining are close, with essentials at the Route 235 and 245 intersection and both Leonardtown and California within ten to fifteen minutes. Schools are part of St. Mary's County Public Schools, and most of Hollywood feeds to Leonardtown High School, which is a meaningful draw for families.
For Buyers
Why Buyers Choose Hollywood
Buyers choose Hollywood for the balance it strikes. It offers privacy, trees, and water while staying within 15 minutes of the base and 10 minutes of Leonardtown. Families value the Leonardtown school assignment, boaters value the protected creeks, and move-up buyers find larger lots and waterfront homes that are rare closer to Route 235.
Wooded, private lots with a central location between Leonardtown and the base
Protected creek waterfront on Cuckold Creek, Mill Creek, and the Patuxent River
Leonardtown High School assignment for most of the community
Greenwell State Park, Sotterley, and Myrtle Point Park close to home
For Sellers
Why Sellers Benefit
Sellers in Hollywood benefit from strong demand for exactly what the area provides, larger private lots and creek waterfront within the Leonardtown school district. That combination is scarce, and buyers who want it are often willing to wait for the right property and act quickly when it appears. Well-presented homes here consistently attract serious, qualified interest and competitive pricing.
Scarce combination of acreage, water, and school district supports strong pricing
Appreciation of roughly 5 to 6 percent annually in recent years
Serious move-up and waterfront buyers act quickly when the right home appears
Days on market around 22 with limited competing inventory
Keep Exploring
More Southern Maryland Communities
Let's Talk
Thinking About Hollywood? Let's Talk.
Whether you're pricing a longtime family home, buying acreage, or just starting to look, you'll get a direct answer and a clear next step.
Jimmy Hayden, Realtor, serving Hollywood, MD and all of Southern Maryland.