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$428,799 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,910 Sq. Ft.
  • 2 Car Garage
  • Updated 10 hours ago

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Open House: 1:00 PM - 4:00 PM

Saturday 5/23 1:00 PM - 4:00 PM

41600 Miss Bessie Drive,Leonardtown, MD 20650

41600 Miss Bessie DriveLeonardtownMD20650

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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 for 41600 Miss Bessie Dr

General

  • Price: $428,799
  • Taxes: $3,908 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2031384
  • Updated: Today (5/22/2026)
  • Added to Site: Today

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
  • 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

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Listing agent

— 41600 Miss Bessie Dr —

  • Michael P Mason

    Long & Foster Real Estate, Inc.

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 41600 Miss Bessie Dr

School District:St. Marys County Public Schools
NameGradesDistance
Leonardtown Elementary School
22885 Duke Street, Leonardtown, MD 20650
PK-50.6 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-82.5 mi
Leonardtown High School
23995 Point Lookout Road, Leonardtown, MD 20650
9-122.9 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/22/2026
Listed
$428,799
94.93%
MLS
6/03/2003
Sold
$219,980
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 41600 Miss Bessie Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,639
—
$361,800
5%
2023
$3,639
—
$343,533
6%
2023
$3,639
9%
$325,267
6%
2022
$3,335
18%
$307,000
2%
2019
$2,832
-8%
$300,633
2%
2021
$3,087
2%
$294,267
2%
2020
$3,020
2%
$287,900
2%
2019
$2,958
3%
$282,000
2%
2018
$2,879
2%
$276,100
2%
2017
$2,832
1%
$270,200
—
2016
$2,798
2%
$270,200
—
2015
$2,751
-12%
$270,200
-10%
2014
$3,130
—
$301,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Long & Foster Real Estate, Inc., Michael P Mason

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41600 Miss Bessie Drive, Leonardtown, MD 20650 (MLS# MDSM2031384) is a Single Family property with 3 bedrooms and 2 full bathrooms. 41600 Miss Bessie Drive is currently listed for $428,799 and was received on May 22, 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.

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