Leonardtown

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Leonardtown, MD Area Guide

Enjoy small-town charm in a Most Convenient Place

Family-Friendly • Coastal • Scenic • Historic • Charming • Quaint • Active • Military-Friendly • Close-Knit • Convenient •

Located in southern Maryland, Leonardtown is the charming county seat of Saint Mary’s County sitting on the coast of Breton Bay. Regarded for its central locale, Leonardtown is widely known as a "Most Convenient Place” within close proximity to a variety of dining, shopping, and recreation as well as Patuxent River Naval Air Station and the Washington DC area.

Leonardtown offers residents and visitors access to numerous attractions like the Port of Leonardtown Winery, Leonardtown Wharf Park, and the Old Jail Museum. The quaint town square contains an array of eclectic shops, restaurants, galleries, government buildings, and historical sites. Outdoor activities abound at nearby Newtowne Neck State Park and Saint Mary’s River State Park. Leonardtown’s community is drawn together for lively events such as Leonardtown First Fridays and the annual U.S. Oyster Festival.

Rent Trends

As of March 2026, the average apartment rent in Leonardtown, MD is $1,535 for one bedroom, $2,183 for two bedrooms, and $2,575 for three bedrooms. Apartment rent in Leonardtown has increased by 2.6% in the past year.

Property Type
Average Rent
Average Sq Ft
Apartment
$1,535/month
700 Sq Ft
See Rental Market Trends in Leonardtown, MD

Getting Around

Explore how walkable, bikeable, drivable, and transit-friendly Leonardtown, MD is for everyday living.

Car-Dependent

38 / 100

This area is considered a car-dependent area and most errands will require a car.

Somewhat Bikeable

31 / 100

You might be able to find places to ride your bike in this area, but you’ll most likely want your car for most errands.

Scores provided by Walk Score

Schools

Captain Walter Francis Duke Elementary

Public

Grades PK-5

9/10

Leonardtown Elementary

Public

Grades PK-5

7/10

Leonardtown Middle

Public

Grades 6-8

8/10

Leonardtown High

Public

Grades 9-12

5/10
School data provided by http://www.greatschools.org The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process. View GreatSchools Rating Methodology Data provided by GreatSchools.org © 2026. All rights reserved.

Points of Interest

Shopping Centers

Parks and Recreation

  • Bowles Farms
  • Greenwell State Park
  • St. Mary's River State Park
  • St. Clements Island State Park
  • St. Clement's Island Museum

Military Bases

Colleges

Top Apartments in Leonardtown

The Hamptons at Leonardtown

The Hamptons at Leonardtown

44980 Hamptons Blvd,
Leonardtown, MD 20650

$2,175 - $2,575

2-3 Beds

Seymour Apartments

Seymour Apartments

22645 Washington St,
Leonardtown, MD 20650

$1,750 - $1,950

1-2 Beds

18937 McKays Cove Ln

18937 McKays Cove Ln

18937 McKays Cove Ln,
Leonardtown, MD 20650

$2,300

3 Beds

20503 Chestnut Ridge Dr

20503 Chestnut Ridge Dr

20503 Chestnut Ridge Dr,
Leonardtown, MD 20650

$2,700

3 Beds

Abberly Crest Apartment Homes

Abberly Crest Apartment Homes

46850 Abberly Crest Ln,
Lexington Park, MD 20653

$1,836 - $3,727

1-3 Beds

St. Marys Landing Apartments and Townhomes

St. Marys Landing Apartments and Townhomes

21590 Pacific Dr,
Lexington Park, MD 20653

$1,270 - $5,228

Studio - 3 Beds

Apartments of Wildewood

Apartments of Wildewood

23314 Surrey Way,
California, MD 20619

$1,605 - $2,495 Total Monthly Price

1-3 Beds

Settler's Landing

Settler's Landing

45086 Voyage Path,
California, MD 20619

$1,706 - $2,640 Total Monthly Price

1-3 Beds | 12 Month Lease

Villas at Greenview West

Villas at Greenview West

45660 Jillian Ct,
Great Mills, MD 20634

$2,100 - $2,369

2-3 Beds

Houses for Rent in Leonardtown

18937 McKays Cove Ln

18937 McKays Cove Ln,
Leonardtown, MD 20650

$2,300

3 Beds | 1.5 Baths

20503 Chestnut Ridge Dr

20503 Chestnut Ridge Dr,
Leonardtown, MD 20650

$2,700

3 Beds | 2.5 Baths

7986 Benjamin Stoddert Ct

7986 Benjamin Stoddert Ct,
La Plata, MD 20646

$1,100 Total Monthly Price

1 Bed | 2 Baths | 12 Month Lease

21323 Foxglove Ct

21323 Foxglove Ct,
Lexington Park, MD 20653

$3,200 Total Monthly Price

4 Beds | 3 Baths

42278 Allison Dr

42278 Allison Dr,
Mechanicsville, MD 20659

$2,800 Total Monthly Price

3 Beds | 3 Baths

18610 Three Notch Rd

18610 Three Notch Rd,
Lexington Park, MD 20653

$1,050

1 Bed | 1 Bath

View More Houses for Rent in Leonardtown

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Methodology

† Our analysis of utilities, groceries, transportation, healthcare, home prices, and other goods and services is sourced from the Cost of Living Index, a respected benchmark published by the Council for Community and Economic Research (C2ER) that provides a thorough overview of living expenses across different regions.

Rent data is provided by CoStar Group’s Market Trend reports. As the industry leader in commercial real estate information, analytics, and news, CoStar conducts extensive research to produce and maintain a comprehensive database of commercial real estate information. We combine this data with public record to provide the most up-to-date rental information available.

Consumer goods, services, and home prices are sourced from the Cost of Living Index published by the Council for Community and Economic Research (C2ER). The data on this page is updated quarterly. It was last published in February 2026.