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$395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,657 Sq. Ft.
  • 2 Car Garage
  • Updated 6 hours ago
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Welcome home! If you need space to spread out, this unique and cozy home on a quiet half-acre lot is just what you've been looking for. Two separate living areas means enjoying movies and gaming in one room while you enjoy peace in the other. This one-of-a-kind floor plan maximizes every square foot, and surprisingly roomier than it appears! With 5 bedrooms, 2 full and 1half bathrooms, there is plenty of personal space for a growing family, multi-generational living, a home office, or hobbies. The perfect blend of rural quiet and everyday functionality. Come take a look and see how this unique space fits your lifestyle!

Full Property Details for 39944 Lady Baltimore Ave

General

  • Price: $395,000
  • Taxes: $3,289 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2031394
  • Updated: Today (5/23/2026)
  • Added to Site: Today

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Family Room, Laundry, Storage Room, Full Bath
  • Interior Features: Crown Moldings, Primary Bath(s), Upgraded Countertops, Walk-in Closet(s), Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Mantel(s), Gas/Propane
  • Appliances: Built-In Microwave, Dishwasher, Refrigerator, Oven/Range - Gas
  • Flooring: Hardwood, Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 5

Other Rooms

  • Laundry: Upper Floor

Exterior

  • Porch/Patio/Deck: Porch(es), Patio(s)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking Features: Gravel Driveway, Crushed Stone
  • Parking Type: Driveway, Attached Garage
  • Garage Description: Built In, Garage - Front Entry, Inside Access

Location

  • County: SAINT MARYS
  • Subdivision: THE WOODS AT BAYSIDE
  • Driving Directions: GPS Accurate

School Information

  • School District: St. Marys County Public Schools
  • Elementary School: Benjamin Banneker
  • Middle School: Leonardtown
  • High School: Chopticon

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Well

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Foundation: Slab
  • Stories Description: Main, Upper 1
  • Square Feet: 2,657
  • Sq. Ft. Source: Estimated
  • Living Area: 2,169 Sq. Ft.
  • Finished Above Grnd: 2,169 Sq. Ft.
  • Unfin. Above Grnd: 488 Sq. Ft.
  • Year Built: 1997
  • Year Built Source: Assessor
  • Property Condition: Good

Additional Structures

  • Other Structures: Shed

Lot Features

  • Lot Size (Acres): 0.46
  • Lot Size (Sq. Ft.): 20,000
  • Lot Size Source: Assessor
  • Zoning: RNC
  • Lot Description: Cleared, Front Yard, Landscaping, Level, Open, Rear Yard, SideYard(s)
  • Fencing (Description): Partially, Privacy

Financial Considerations

  • Price Per Sq. Ft.: $182.11
  • Assessment Year: 2026
  • City/TownTax Freq: Annually
  • County Tax: $3,289
  • County Tax Freq: Annually
  • Tax w/Assessment: $352,000
  • Tax Amount: $3,289
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2008

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 42

Listed by CENTURY 21 New Millennium, Kimberly Hayes

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Listing agent

— 39944 Lady Baltimore Ave —

  • Kimberly Hayes

    CENTURY 21 New Millennium

Listing Office Email: tommy.higgins@c21nm.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39944 Lady Baltimore Ave

School District:St. Marys County Public Schools
NameGradesDistance
Benjamin Banneker Elementary School
27180 Point Lookout Rd, Loveville, MD 20656
PK-53.7 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-84.5 mi
Chopticon High School
25390 Colton Point Rd, Morganza, MD 20660
9-125.6 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 39944 Lady Baltimore Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/23/2026
Listed
$395,000
29.51%
MLS
12/20/2019
Sold
$305,000
—
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 39944 Lady Baltimore Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,240
—
$342,700
5%
2023
$3,240
—
$325,733
5%
2023
$3,240
16%
$308,767
6%
2022
$2,801
6%
$291,800
3%
2019
$2,635
-9%
$283,800
3%
2021
$2,899
3%
$275,800
3%
2020
$2,816
2%
$267,800
2%
2019
$2,763
3%
$262,833
2%
2018
$2,694
1%
$257,867
2%
2017
$2,655
1%
$252,900
—
2016
$2,623
2%
$252,900
—
2015
$2,575
-6%
$252,900
-4%
2014
$2,744
—
$263,700
—
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.

Estimate the Cost for 39944 Lady Baltimore Ave

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by CENTURY 21 New Millennium, Kimberly Hayes

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39944 Lady Baltimore Avenue, Leonardtown, MD 20650 (MLS# MDSM2031394) is a Single Family property with 5 bedrooms, 2 full bathrooms and 1 partial bathroom. 39944 Lady Baltimore Avenue is currently listed for $395,000 and was received on May 23, 2026. Want to learn more about 39944 Lady Baltimore Avenue? 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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