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$669,500 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,500 Sq. Ft.
  • 2 Car Garage
  • Updated 11 hours ago
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Country Living at it's best!!! NO HOA in a minor subdivision of only 7 houses within a couples of miles of downtown Leonardtown. Two primary suites or one in-law ADA approved apartment on main level, includes gas fireplace in living area, pocket doors, walk in shower, coffee bar with small refrigerator, three season porch and direct access to laundry facilities/garage w/ADA approved ramp. Year round heated sunroom. Oh by the way, insulated inside walls with six inch exterior walls. Main house upgraded kitchen, built in refrigerator, eat at counter with bar stools. Granite counter tops. Butler's pantry w/wine refrigerator. Recessed lights through out, Cali Bamboo flooring. Dining room and a study with built in desk and ample storage. Upstairs second primary suite, walk-in closet, tub with shower. Additional two bedrooms feature a Jack and Jill bath. Take a walk on the deck walkway to the Pavilion and enjoy the view of the 20 plus raised bed garden of vegetables or walk over to the chicken coup and have fresh eggs for breakfast. Summer and fall will treat you to the many eatible fruit, fig and berry bushes and trees that enhance the landscaping of this private 2.29 acre lot. Many additional features like a small fenced area for pets, garden shed, second refrigerator, upright freezer, utility sink, extra cabinets, custom drapes, French doors, extra large TV, propane free standing stove, 9 foot ceilings, to mention a few. Detailed list and manuals will be provided.

Full Property Details for 21390 Little St Annes Ln

General

  • Price: $669,500
  • Taxes: $4,967 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2031120
  • Updated: Today (5/12/2026)
  • Added to Site: Today

Interior

  • Interior Features: Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Butlers Pantry, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Table Space, Pantry, Recessed Lighting, Store/Office, Upgraded Countertops, Walk-in Closet(s), Window Treatments, Wine Storage
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Free Standing, Gas/Propane, Mantel(s)
  • Appliances: Built-In Microwave, Built-In Range, Dishwasher, Dryer, Extra Refrigerator/Freezer, Freezer, Oven/Range - Gas, Refrigerator, Stove, Washer, Water Heater - Tankless, Water Heater
  • Flooring: Bamboo, Carpet, Ceramic Tile, Partially Carpeted

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 3
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Security/Safety: Carbon Monoxide Detector(s), Smoke Detector

Exterior

  • Exterior Features: Extensive Hardscape, Flood Lights, Outbuilding(s), Play Area
  • Porch/Patio/Deck: Porch(es), Patio(s)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 5
  • Parking Features: Asphalt Driveway, Paved Driveway, Private
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Additional Storage Area, Built In, Garage - Front Entry, Garage Door Opener, Inside Access

Location

  • County: SAINT MARYS
  • Subdivision: LITTLE ST ANNES
  • Driving Directions: (Rt 5) Point Lookout Rd to Medley's Neck Road (Rt 244) to left on Little Saint Anne's Lane. Follow directional signs to house

School Information

  • School District: St. Mary's County Public Schools
  • Elementary School: Leonardtown
  • Middle School: Leonardtown
  • High School: Leonardtown

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C, Geothermal, Heat Pump(s), Multi Units
  • Cooling Fuel: Geothermal, Electric
  • Heating Type: Heat Pump(s), Heat Pump - Gas BackUp, Other
  • Heating Fuel: Geo-thermal, Natural Gas, Propane - Leased
  • Water Heater: Electric

Utilities

  • Sewer: On Site Septic
  • Water: Well
  • Utility Description: Cable TV Available, Propane

Structural Information

  • Architectural Style: Traditional, Other
  • Structure Type: Detached
  • Construction: Combination, HardiPlank Type, Stone, Stick Built, Vinyl Siding
  • Foundation: Crawl Space, Other
  • Walls/Ceilings: 2 Story Ceilings, High
  • Windows: Casement, Double Hung, Double Pane, Screens
  • Doors: French
  • Stories Description: Main, Upper 1
  • Square Feet: 3,500
  • Sq. Ft. Source: Estimated
  • Living Area: 3,500 Sq. Ft.
  • Finished Above Grnd: 3,500 Sq. Ft.
  • Year Built: 2003
  • Year Built Source: Assessor
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Poultry House, Shed

Lot Features

  • Property View: Garden/Lawn, Panoramic
  • Lot Size (Acres): 2.29
  • Lot Size (Sq. Ft.): 99,752
  • Lot Size Source: Assessor
  • Zoning: RPD
  • Lot Description: Backs to Trees, Front Yard, Landscaping, Level, No Thru Street, Rear Yard, Rural
  • Fencing (Description): Partially, Rear

Green Features

  • RFactor - Walls: 6"

Financial Considerations

  • Price Per Sq. Ft.: $191.29
  • Assessment Year: 2026
  • County Tax: $4,967
  • County Tax Freq: Annually
  • Tax w/Assessment: $522,533
  • Tax Amount: $4,967
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 4C

Listed by CENTURY 21 New Millennium, Jan N Barnes

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Listing agent

— 21390 Little St Annes Ln —

  • Jan N Barnes

    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 21390 Little St Annes Ln

School District:St. Marys County Public Schools
NameGradesDistance
Leonardtown Elementary School
22885 Duke Street, Leonardtown, MD 20650
PK-53 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-81.4 mi
Leonardtown High School
23995 Point Lookout Road, Leonardtown, MD 20650
9-121.1 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 21390 Little St Annes Ln Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/12/2026
Listed
$669,500
1095.54%
MLS
4/16/2003
Sold
$56,000
—
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 21390 Little St Annes Ln

Year
Property Taxes
Change
Tax Assessment
Change
2023
$4,869
—
$517,500
6%
2023
$4,869
—
$490,300
6%
2023
$4,869
16%
$463,100
6%
2022
$4,184
47%
$435,900
44%
2019
$2,847
-10%
$302,000
2%
2021
$3,161
2%
$295,700
2%
2020
$3,095
—
$289,400
—
2019
$3,094
1%
$289,400
—
2018
$3,075
-1%
$289,400
-1%
2017
$3,117
2%
$292,300
1%
2016
$3,062
4%
$290,333
1%
2015
$2,936
-3%
$288,367
1%
2014
$3,035
—
$286,400
—
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 21390 Little St Annes Ln

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

Be ready to buy your new home!

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NMLS#: 1598647

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Listed by CENTURY 21 New Millennium, Jan N Barnes

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21390 Little Saint Annes Lane, Leonardtown, MD 20650 (MLS# MDSM2031120) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 21390 Little Saint Annes Lane is currently listed for $669,500 and was received on May 12, 2026. Want to learn more about 21390 Little Saint Annes Lane? 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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