Homes For Sale in Leonardtown MD

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Leonardtown

MD
Average Sales Price
$813,380
Median Sales Price
$587,450
Population
14,156
Total Listings
70

About the Area Leonardtown Maryland

Leonardtown has a character that is different from many other communities in Southern Maryland. It is the county seat of St. Mary’s County and an incorporated town with a historic downtown centered around Leonardtown Square. The supplied local information describes a community with a town center, healthcare facilities, schools, restaurants, shopping, waterfront recreation, and a growing collection of locally owned businesses.

The town's history reaches back to Maryland's colonial period. Its historic buildings, traditional street layout, town square, museums, and older residences provide reminders of that history, while newer residential communities and continued downtown investment have expanded the housing and lifestyle options available today.

One of Leonardtown's defining geographic features is Breton Bay. Leonardtown Wharf provides public waterfront access close to downtown and supports activities such as kayaking and stand-up paddleboarding as well as community events and outdoor concerts.

Leonardtown's Arts & Entertainment District further distinguishes the community. Residents and visitors can explore galleries, attend workshops and performances, participate in arts programming, and attend events throughout the downtown area.

The community attracts a mix of households, including people working in county government, healthcare, education, local businesses, and throughout the larger Lexington Park–Patuxent River employment corridor. Buyers may also appreciate having restaurants, shops, parks, schools, county services, and recreational destinations relatively close together.

 

Demographics

Data provided by Attom Data
Population
Employment
Population
14.2K
14.2K in 2020
Density
134.5
per square mile
Households
5K
40 With Children
Gender
49% / 51%
Men Vs Women
Occupancy
77% / 23%
Owned Vs Rented
Age Median: Years
Education Level

Homes for Sale in Leonardtown Maryland

Buyers searching for Leonardtown Maryland homes for sale may encounter everything from older properties near the historic town center to established subdivisions, newer communities, custom homes, and properties near the water.Housing varies considerably depending on whether buyers are searching inside the incorporated town, in a planned community, or in the broader Leonardtown mailing area. Lot size, utilities, homeowners association requirements, water access, school assignment, commute routes, and proximity to downtown should all be evaluated property by property.

Real Estate in Leonardtown
Leonardtown real estate includes detached single-family homes in a variety of architectural styles and ages. The supplied information identifies historical homes, renovation opportunities, newer homes, and waterfront properties as part of the local housing mix.

Buyers may also encounter newer residential development and planned communities. Townhomes and other attached properties can appear in the broader Leonardtown market as well, although inventory depends on current market conditions. Buyers seeking larger or higher-end homes can also find custom residences and properties with additional acreage in portions of the Leonardtown area.

Waterfront and water-oriented real estate is another important part of the market. The supplied source specifically identifies Foxwell Point as an area where buyers may encounter waterfront homes. Buyers considering a waterfront property should investigate flood-zone information, shoreline conditions, insurance requirements, water depth and boating access where applicable, and any permitting or Critical Area considerations affecting the individual parcel.





The Southside Group Real Estate

Leonardtown Communities & Neighborhoods

Leonardtown Hamptons

Overview: Leonardtown Hamptons is an established residential community in the Leonardtown area. Its neighborhood setting provides an option for buyers who want to remain close to Leonardtown's shopping, schools, services, and downtown destinations.

Property Types: Residential properties, primarily detached homes depending on current inventory.

Chestnut Ridge

Overview: Chestnut Hills is an established Leonardtown residential area characterized by a suburban neighborhood setting and convenient access to the broader town.

Property Types: Residential single-family properties.

Hood Lane Area

Overview: The Hood Lane area provides another residential setting within Leonardtown, with convenient access to local amenities and surrounding St. Mary’s County destinations.

Property Types: Residential properties; styles and lot configurations vary.

Clarks Rest

Overview: Clarks Rest is an established residential community in Leonardtown with neighborhood streets and access to shopping, dining, recreation, and other town amenities.

Property Types: Primarily residential homes, with individual styles depending on the section and property.

Fenwick Street Area

Overview: Fenwick Street is closely connected to Leonardtown's historic downtown environment. It can appeal to buyers interested in living near restaurants, shops, arts destinations, community events, and the town square.

Property Types: A mix of residential properties associated with the older town environment.

Foxwell Point

Overview: Foxwell Point is particularly relevant to buyers searching for waterfront or water-oriented Leonardtown real estate. The supplied local information specifically identifies this area as a location where waterfront homes may be available.

Property Types: Residential properties, including waterfront homes depending on current inventory.

Schools & Education in Leonardtown Maryland

Leonardtown is served by St. Mary’s County Public Schools (SMCPS). The supplied information identifies Leonardtown Elementary School, Leonardtown Middle School, Leonardtown High School, and Captain Walter Francis Duke Elementary School
among schools located in the Leonardtown area.

A Leonardtown mailing address does not guarantee assignment to a particular school.
St. Mary’s County Public Schools maintains individual attendance-boundary maps for
its elementary, middle, and high schools, including Leonardtown Middle and Leonardtown High. Buyers should verify the assignment for a specific property directly with SMCPS
because school boundaries can change.

St. Mary’s County Public Schools boundary maps. Private education is available locally
as well. The supplied information identifies Father Andrew White, S.J. School and
St. Mary’s Ryken High School in Leonardtown. Families should verify current grade
levels, enrollment policies, tuition, and programs directly with each school.

Higher education is available at the College of Southern Maryland's Leonardtown
Campus, located on Hollywood Road. St. Mary’s College of Maryland is another
higher-educationoption within St. Mary’s County.

 

Elementary Schools (4)Middle Schools (3)High Schools (3)
Name
Category
Grades
Library
Ratio
7/10
Leonardtown Elementary School
22885 Duke St, Leonardtown, MD 20650
Public
PK - 5
No
18:1 STUDENTS/TEACHERS
5/10
Benjamin Banneker Elementary School
27180 Point Lookout Rd, Loveville, MD 20656
Public
PK - 5
No
16:1 STUDENTS/TEACHERS
0/10
Father Andrew White Sj School
22850 Washington Street, Leonardtown, MD 20650
Private
PK - 8
Yes
14:1 STUDENTS/TEACHERS
0/10
Little Seedlings Christian Preschool & Kindergarden
25550 Point Lookout Road, Leonardtown, MD 20650
Private
PK - KG
Yes
8:1 STUDENTS/TEACHERS
Name
Category
Grades
Library
Ratio
8/10
Leonardtown Middle School
24015 Point Lookout Rd, Leonardtown, MD 20650
Public
6 - 8
No
19:1 STUDENTS/TEACHERS
0/10
Father Andrew White Sj School
22850 Washington Street, Leonardtown, MD 20650
Private
PK - 8
Yes
14:1 STUDENTS/TEACHERS
0/10
Leonard Hall Jr Naval Academy
41740 Baldridge St, Leonardtown, MD 20650
Private
6 - 12
Yes
6:1 STUDENTS/TEACHERS
Name
Category
Grades
Library
Ratio
8/10
Leonardtown High School
23995 Point Lookout Rd, Leonardtown, MD 20650
Public
9 - 12
No
21:1 STUDENTS/TEACHERS
0/10
Dr. James A. Forrest Career and Technology Center
24005 Point Lookout Rd, Leonardtown, MD 20650
Public
9 - 12
No
STUDENTS/TEACHERS
0/10
Leonard Hall Jr Naval Academy
41740 Baldridge St, Leonardtown, MD 20650
Private
6 - 12
Yes
6:1 STUDENTS/TEACHERS

Things to Do Leonardtown MD

Leonardtown Maryland Real EstateLeonardtown's downtown, waterfront, arts community, shops, restaurants, and events give the town a lifestyle that is relatively distinctive within Southern Maryland. Leonardtown Wharf is one of the town's signature destinations. Located along Breton Bay, the waterfront park supports kayaking, stand-up paddleboarding, community gatherings, and outdoor events. The town also hosts music and arts programming at the Wharf.

The Port of Leonardtown Winery and surrounding park provide another local destination. Visitors can enjoy the winery while the adjacent outdoor environment connects with the McIntosh Run water trail toward Leonardtown Wharf. Local tourism information describes the paddle route as nearly three miles.Downtown Leonardtown also offers a growing mix of independent shops and restaurants. The supplied information highlights destinations such as Shepherd's Old Field Market, Salted Scoop, Heritage Chocolates, Botanic Coffee Shop & Deli, and Crazy for Ewe Yarns.

Shepherd's Old Field Market is especially notable as a repurposed historic commercial building that
now functions as an indoor marketplace and community gathering space with shops, food and
beverage options, and services.Additional destinations identified in the supplied information include Leonardtown Maryland Real EstateOlde Town Pub, North End Gallery, The Front Porch, Antoinette's Garden, Sweetbay Restaurant & Bar, SOCIAL Coffeehouse & Cocktail Bar, Mac's Tap & Table, Leonardtown Arts Center, andthe Old Jail Museum and Visitor Center.

Leonardtown's designation as Southern Maryland's only Arts & Entertainment District supports galleries, art workshops, creative businesses, live music, and cultural programming. The town's event calendar also includes recurring community activities such as First Fridays and seasonal programming. For residents who enjoy outdoor recreation, the Leonardtown area offers kayaking, paddleboarding, walking, fishing, and easy access to additional St. Mary’s County parks and waterways.


Restaurants
Home Services
Health & Medical
Local Services
Shopping
Recreation
Arts & Entertainment
Food
Beauty
Nightlife
Event Planning & Services
Automotive
Religious Organizations
Financial Services
Professional Services
Travel
Pets
Education
Public Services & Government

  • Hot Diggity Dog!

    Point Lookout Rd, Great Mills, MD 20634

    Food Stands Phone: 301-672-0076

  • Arby’s

    40874 Merchants Ln, Leonardtown, MD 20650

    Fast Food

  • Pizza Hut

    40955 Merchants Ln Unit 5, Leonardtown, MD 20650

    Italian Phone: 301-475-2700

  • KFC

    26501 Point Lookout Road, Leonardtown, MD 20650

    Chicken Wings Phone: 301-997-1401

  • Pho Saigon

    40874 Merchant Ln, Leonardtown, MD 20650

    Vietnamese Phone: 240-309-4044

  • Guenthers Bistro

    25470 Point Lookout Rd, Leonardtown, MD 20650

    Internet Cafes Phone: 301-475-8989

  • Happy Dragon Restaurant

    40955 Merchants Ln, Leonardtown, MD 20650

    Chinese Phone: 301-475-9695

  • Salsa’s Mexican Cafe

    25470 Point Lookout Rd, Leonardtown, MD 20650

    Mexican Phone: 301-997-0442

  • Hong Kong Buffet

    40865 Merchants Ln, Leonardtown, MD 20650

    Chinese Phone: 301-475-8608

  • McDonald’s

    40950 Merchants Ln, Leonardtown, MD 20650

    Burgers

Getting Around in Leonardtown MD
Driving remains the primary transportation method for many Leonardtown residents.Maryland Route 5 / Point Lookout Road is one of the principal routes through the area and connects Leonardtown with communities to the north and south. Nearby road connections provide access toward Hollywood, California, Lexington Park, and Naval Air Station Patuxent River.Leonardtown's central St. Mary’s County location makes it practical for people who regularly travel to California, Lexington Park, Hollywood, Mechanicsville, and other county communities. NAS Patuxent River is also an important regional employment destination for residents throughout this part of the county.Public transportation is available through the St. Mary’s Transit System (STS). Current county schedules include Route 1 between Leonardtown and Lexington Park via California, Route 2 between Leonardtown and Charlotte Hall via Loveville, Route 3 between Lexington Park and Leonardtown via Great Mills, and Route 12 between California and Charlotte Hall via Leonardtown.STS has operated fare-free since July 1, 2025, according to the county's current transit information.St. Mary’s Transit System routes and schedulesFor aviation, the St. Mary’s County Regional Airport is located in the California area and supports general and regional aviation. Travelers requiring scheduled commercial airline service generally use airports in the Washington–Baltimore region, including Ronald Reagan Washington National Airport, Baltimore/Washington International Thurgood Marshall Airport, and Washington Dulles International Airport.

Frequently Asked Questions

Is Leonardtown a good place to live?

Leonardtown can appeal to buyers looking for small-town character combined with restaurants, shops, parks, schools, arts, community events, and waterfront recreation. Its central St. Mary’s County location can also be useful for people working throughout Leonardtown, California, Lexington Park, or the NAS Patuxent River employment corridor. Whether it is the right location depends on a buyer's budget, commute, housing preferences, school needs, and desired proximity to downtown or the water.

 

Are there homes for sale in Leonardtown?

How is the Leonardtown real estate market?

What is Leonardtown, Maryland known for?

What outdoor activities are available in Leonardtown?

Is Leonardtown close to NAS Patuxent River?

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