Mid St. Mary's County Hollywood & Leonardtown, Md

Welcome to Hollywood and Leonardtown, MD! These two waterfront towns in St. Mary’s County are Southern Maryland gems, offering a luxurious and easy Chesapeake Bay lifestyle. Whether you’re searching for your next home, a serene getaway, or an investment property, these communities provide an idyllic blend of waterfront beauty, small-town charm, and upscale living, all in easy reach of the Washington D.C. metro area.

Hollywood, MD is an unincorporated community spanning roughly 34 square miles with around 11,000 residents. It began as a farming community, with rolling landscapes and tight-knit neighborhoods. It has retained its quiet, pastoral charm over the years while gently incorporating modern residential developments.

Just a short drive away, Leonardtown, MD serves as the cultural and administrative heart of the county. Spanning just 4 square miles with a population of 5,000, this former port town has rich colonial roots, brick-lined streets, and a walkable downtown filled with art galleries and wine bars.

Both towns offer a relaxed pace of life. If you’re after a laid-back lifestyle in an idyllic setting while still having access to modern amenities, homes for sale in Hollywood, MD, and Leonardtown, MD real estate present an intriguing opportunity.

The homes for sale in Hollywood, MD, and Leonardtown, MD, appeal to a wide range of lifestyles, particularly those drawn to the Chesapeake Bay’s tranquil, nature-rich surroundings. This area specializes in:

• Waterfront properties with private docks, ideal for boaters and sailing enthusiasts.
• Luxury single-family homes with spacious acreage and mature landscaping.
• Estate-style residences and equestrian properties, offering acreage and privacy.
• Townhomes and condos, offering low-maintenance living near shops and dining.

The houses here feature a mix of architectural styles that reflect both tradition and modern living, blending with the region’s rural, waterfront setting while complementing its historic charm:

• Colonial: Symmetrical designs with brick or wood exteriors, multi-paned windows, and traditional layouts that fit with the preserved historical buildings of Leonardtown.
• Cape Cod: Compact and charming with steep roofs, dormers, and central chimneys, offering simplicity and classic American style.
• Craftsman: Low-pitched roofs, wide porches, and exposed woodwork fit well in Hollywood’s wooded areas, offering beautiful homes.

Life in Hollywood and Leonardtown blends quiet, rural charm with modern conveniences. Here you’ll find strong schools, outdoor recreation, vibrant events, and great local dining.

Getting Around

Though tranquil and rural in feel, Hollywood and Leonardtown are highly accessible. Key roads like Maryland Route 5 (MD 5), MD 245, and MD 235 connect these towns to the Washington D.C., metro area, which is under two hours away.

The nearest major airport is the Ronald Reagan Washington Memorial National Airport (DCA) in Washington, D.C., but you can catch flights within the region at St. Mary’s County Regional Airport (LTW), just 4 miles northeast of Leonardtown.

Schools

The St. Mary’s County Public Schools (SMCPS) district serves both towns with several high-performing schools, including Hollywood Elementary School and Leonardtown High School. There are also private schools available, such as St. Mary’s Ryken High School and King’s Christian Academy, which both offer college-preparatory education. For higher education, the College of Southern Maryland—Leonardtown Campus offers accessible, high-quality programs just minutes away.

Outdoor Recreation

Living in Southern Maryland means embracing the outdoors. With easy access to the Patuxent River and Breton Bay, boating, fishing, crabbing, and kayaking are part of everyday life. Residents also enjoy full-service marinas, public boat ramps, and private docks, perfect for weekend sailing trips or sunset cruises.

Dennis Point Marina & Campground, located south of Hollywood, MD, features 81 deep-water slips, a fueling station, and full-service boat maintenance. The grounds also offer 117 campsites, cabin rentals, a swimming pool, playgrounds, and a seafood restaurant with views of the Patuxent River.

Leonardtown Wharf provides a charming waterfront space with a public boat ramp, kayak launch, and scenic walking areas. It’s also a central location for community events, like the Leonardtown Wharf Fest and Leonardtown First Fridays.

St. Mary’s River State Park, just 10 minutes away from Leonardtown, includes a 7.5-mile trail loop around a peaceful lake, ideal for hiking, biking, and horseback riding. Anglers can enjoy fishing for bass and bluegill in a serene setting.

Breton Bay Golf & Country Club features an 18-hole championship course, private pool, and tennis facilities. The Ironwood Grill restaurant offers casual dining options with scenic views of Breton Bay.

Cultural Experiences

Leonardtown and Hollywood, MD, are rich in history. Visit Leonardtown Square and the Old Jail Museum for insights into the town’s colonial past, or explore Historic Sotterley, a preserved 18th-century estate near Hollywood that offers guided tours focused on plantation life and African-American history.

Dining

Food is central to life in Southern Maryland, combining coastal flavors with farm-fresh ingredients. Local favorites include Sweetbay Restaurant, known for its waterfront views and creative seafood dishes, The Front Porch, offering upscale Southern food in a charming historic home, and Social Coffeehouse, a go-to for artisan coffee, pastries, and light bites. Antoinette’s Garden, a wine bar and café, and Olde Town Pub, a lively gathering place for locals, round out Leonardtown’s welcoming and walkable food district.

Shopping

Leonardtown, MD, offers a walkable, vibrant shopping scene centered around the historic Leonardtown Square. Discover unique finds at Shepherd’s Old Field Market, North End Gallery, and Fenwick Street Used Books & Music. Frequent festivals, artisan boutiques, and cozy shops make downtown Leonardtown a favorite for locals and visitors.

Hollywood offers a more relaxed shopping experience. Browse floral arrangements at Anchored Roots Farm and handcrafted items at Keepin’ It Local. Small, creative businesses and custom boutiques reflect the town’s quiet charm and close-knit community.

Community Events

Leonardtown is known for its vibrant cultural calendar. The walkable downtown is full of galleries, cafes, and boutiques. Here are a few of the events you won’t want to miss:

• Leonardtown First Fridays – A lively monthly event that brings downtown Leonardtown to life with art exhibits, live music, and activities that showcase the local creative community.
• Leonardtown Summer Music Festival – This free concert series brings live jazz, country, and bluegrass to Leonardtown Square and the scenic Leonardtown Wharf, creating a vibrant atmosphere all summer long.
• St. Mary’s County Oyster Festival – This two-day annual event celebrates Chesapeake Bay seafood with oyster shucking contests, food stands, craft beer, live entertainment, and local vendors.

Hollywood complements this with a more relaxed, rural feel with local BBQ joints, hidden seafood gems, and scenic drives through farmland. The combination of lively community events with laid-back leisure activities makes for fun times with friends and family.

When you’re ready to explore homes for sale in Hollywood, MD, or Leonardtown, MD real estate, our team at McNelis & Associates of Berkshire Hathaway HomeServices PenFed Realty is here to help. Led by Chris McNelis, our team brings over 30 years of local experience and deep knowledge of the Chesapeake Bay lifestyle. Contact us at our email address: info(at)lovechesapeake(dotted)com to get started.