41600 Miss Bessie Drive, Leonardtown, MD 20650 - Photo 1

1/1

$434,000

Sold
Closed
Single Family
3 Beds
2 Full Baths
1,910 Sq. Ft.
2 Car Garage
Updated 6 days ago

1/1

Property Description

Brick-front one-level rambler featuring 3 bedrooms, 2 full bathrooms, and over 1,900 finished square feet. A welcoming covered front porch leads to an open and spacious interior with hardwood flooring throughout the foyer, hallway, living room, and formal dining room. The living room features a gas fireplace, while the dining room offers cathedral ceilings and Palladian windows for abundant natural light. The kitchen opens to the living area and includes a breakfast area, center island, recessed lighting, built-in microwave, and new luxury vinyl plank flooring. The primary suite features a walk-in closet and an ensuite bathroom with dual vanities, a soaking tub, and a separate shower. All bedrooms have new carpeting, and the interior has been freshly painted throughout. Both bathrooms have been updated with new ceramic tile flooring, toilets, and light fixtures. Additional highlights include a laundry room conveniently located off the kitchen and garage, plus an oversized attached 2-car garage with a utility sink and side-yard access. Ideally located just minutes from Downtown Leonardtown, Leonardtown Wharf, shopping, restaurants, MedStar St. Mary's Hospital, and commuter routes to NAS Pax River. Enjoy nearby recreation and entertainment, including kayaking, paddle yoga, waterfront activities, and weekend concerts on the square.

Full Property Details

Full Property Details for 41600 Miss Bessie Dr

General

Sold For: $434,000
Taxes: $3,908 (2025)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDSM2031384
Added to Site: 51 day(s) ago

Interior

Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Foyer, Breakfast Room, Laundry, Primary Bathroom
Interior Features: Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Breakfast Area, Carpet, Ceiling Fan(s), Combination Kitchen/Living, Entry Level Bedroom, Formal/Separate Dining Room, Kitchen - Island, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Wood Floors
Fireplace: Yes
Number of Fireplaces: 1
Fireplace(s): Gas/Propane, Mantel(s), Marble
Appliances: Built-In Microwave, Dishwasher, Disposal, Exhaust Fan, Oven/Range - Electric, Refrigerator, Washer/Dryer Hookups Only
Flooring: Ceramic Tile, Carpet, Hardwood, Luxury Vinyl Plank

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2
Main Floor Baths: 2
Main - Full Baths: 2

Bedrooms

Total Bedrooms: 3
Bedrooms Main & Up: 3

Other Rooms

Laundry: Main Floor

Exterior

Exterior Features: Exterior Lighting, Satellite Dish, Sidewalks
Porch/Patio/Deck: Patio(s), Porch(es)

Parking

Garage: Yes
Garage Spaces: 2
Total Spaces: 4
Parking Features: Asphalt Driveway, Paved Parking
Parking Type: Attached Garage, Driveway
Garage Description: Garage Door Opener, Garage - Front Entry

Location

Municipality: Leonardtown
County: SAINT MARYS
Subdivision: LEONARDTOWN
Driving Directions: Route 5 (Point Lookout Road) to Hollywood Road to the right, Doctors Crossing Way to the right on Miss Bessie Drive to 41600 on the right
City Limits: Yes

School Information

School District: St. Mary's County Public Schools

Heating & Cooling

Central air: Yes
Cooling Type: Ceiling Fan(s), Central A/C
Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric, Propane - Owned
Water Heater: Electric

Utilities

Sewer: Public Sewer
Water: Public

Structural Information

Architectural Style: Ranch/Rambler
Structure Type: Detached
Construction: Brick Front, Vinyl Siding
Foundation: Crawl Space
Walls/Ceilings: Cathedral Ceilings
Windows: Double Pane, Screens, Palladian
Stories Description: Main
Square Feet: 1,910
Sq. Ft. Source: Assessor
Living Area: 1,910 Sq. Ft.
Finished Above Grnd: 1,910 Sq. Ft.
Year Built: 2004
Year Built Source: Assessor
Property Condition: Very Good

Lot Features

Lot Size (Acres): 0.36
Lot Size (Sq. Ft.): 15,681
Lot Size Source: Assessor
Zoning: R-SF

Financial Considerations

Price Per Sq. Ft.: $224.5
Assessment Year: 2026
City/TownTax: $435
City/TownTax Freq: Annually
County Tax: $3,473
County Tax Freq: Annually
Tax w/Assessment: $366,800
Tax Amount: $3,908
Tax Year: 2025
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 1910

Disclosures and Reports

Ownership: Fee Simple
Lot Number: 1

Listed by Long & Foster Real Estate, Inc., Michael P Mason
Sold by RE/MAX One, Sandra Foraci

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Listing agent

— 41600 Miss Bessie Dr —

Michael P Mason

Long & Foster Real Estate, Inc.

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Schools

Schools serving 41600 Miss Bessie Dr

School District:St. Marys County Public Schools

Name	Grades	Distance
Leonardtown Elementary School 22885 Duke Street, Leonardtown, MD 20650	PK-5	0.6 mi
Leonardtown Middle School 24015 Point Lookout Road, Leonardtown, MD 20650	6-8	2.5 mi
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650	9-12	2.9 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 41600 Miss Bessie Dr

Date

Details

Price

Change

Source

6/26/2026

Sold

$434,000

1.21%

MLS

5/22/2026

Listed

$428,799

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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41600 Miss Bessie Drive, Leonardtown, MD 20650 (MLS# MDSM2031384) is a Single Family property that was sold at $434,000 on June 26, 2026. Want to learn more about 41600 Miss Bessie Drive? Do you have questions about finding other Single Family real estate for sale in Leonardtown? You can browse all Leonardtown real estate or contact a Coldwell Banker agent to request more information.

41600 Miss Bessie Dr Leonardtown, MD 20650