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$565,000

  • For Sale
  • Under Contract
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,625 Sq. Ft.
  • 2 Car Garage
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Nestled on a beautifully maintained 1 acre lot, this 5 bedroom, 3.5 bathroom home is conveniently located in Leonardtown's Wilderness Run community. A welcoming foyer leads to a formal dining room and a charming country style kitchen which opens to a spacious family room. The kitchen features space for a table, a large pantry, stainless steel appliances, granite countertops, and direct access to the expansive rear deck overlooking the large private backyard with firepit area and mature trees adding natural privacy. The door off the family room leads to a cozy nook, great for drinking your morning coffee as you watch the birds and abundant wildlife. A convenient flex room off the foyer is perfect for a home office or quiet sitting room. Upstairs, the large primary suite has an en suite bathroom with soaking tub and a generous walk-in closet. Three additional bedrooms are comfortably sized with nice closets. The second floor has a laundry area for everyday convenience. The fully finished basement provides exceptional versatility. It includes a well-appointed kitchenette with abundant cabinetry and granite countertops with subway tile backsplash. A large recreation room with built-ins gives plenty of room for entertaining. A full bath has dual access points for the additional bedroom, office or home gym. This room is complete with a generous closet and stackable washer and dryer and multiple windows for natural light and an exterior ground level exit door. The basement also has a large storage area with shelving to complete the lower level. The neighborhood is located within minutes of Downtown Leonardtown with restaurants, shopping, nightlife, the winery, and seasonal events. The wharf offers a boardwalk, playground, and beautiful water views.

Full Property Details for 21060 Woodmere Dr

General

  • Price: $565,000
  • Taxes: $4,348 (2025)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2028504
  • Updated: 12/30/2025
  • Added to Site: 35 day(s) ago

Interior

  • Rooms/Areas: Bedroom 5
  • Interior Features: Attic, 2nd Kitchen, Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Breakfast Area, Built-Ins, Carpet, Ceiling Fan(s), Dining Area, Family Room Off Kitchen, Kitchen - Table Space, Wood Floors
  • Appliances: Built-In Microwave, Dishwasher, Dryer - Electric, Extra Refrigerator/Freezer, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Stove, Washer
  • Flooring: Carpet, Hardwood, Luxury Vinyl Tile, Vinyl

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 4
  • Bedrooms Lower: 1

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Front Entry, Garage Door Opener

Location

  • County: SAINT MARYS
  • Subdivision: WILDERNESS RUN
  • Driving Directions: From Point Lookout Road turn into Wilderness Run, 0.6 of a mile take a left onto Woodmere Drive, 0.1 of a mile take a left onto 21060 Woodmere Drive. The driveway is not obvious. Look for 2 mailboxes together and the drive is the very next left. If you cross over Woodbury Place you have gone too far. Turn around and look for the unmarked driveway. Will have a for sale sign there,

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

Utilities

  • Sewer: On Site Septic
  • Water: Public
  • Utility Description: Water Available

Structural Information

  • Architectural Style: Transitional
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Full, Heated, Daylight, Partial, Fully Finished, Outside Entrance, Rear Entrance, Shelving, Walkout Level, Windows
  • Foundation: Block
  • Roof: Composite
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,625
  • Sq. Ft. Source: Assessor
  • Living Area: 3,075 Sq. Ft.
  • Finished Above Grnd: 2,525 Sq. Ft.
  • Finished Below Grnd: 550 Sq. Ft.
  • Year Built: 2001
  • Year Built Source: Assessor
  • Property Condition: Excellent

Unit Information

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 1

Lot Features

  • Lot Size (Acres): 0.99
  • Lot Size (Sq. Ft.): 43,124
  • Lot Size Source: Assessor
  • Zoning: RNC
  • Lot Description: Backs to Trees, Cleared, No Thru Street, Rear Yard, Secluded, Trees/Wooded

Financial Considerations

  • Price Per Sq. Ft.: $223.76
  • Assessment Year: 2025
  • County Tax: $4,348
  • County Tax Freq: Annually
  • Tax w/Assessment: $453,000
  • Tax Amount: $4,348
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 3075

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: televisions
  • Inclusions: Ceiling fans, washer and dryer in hallway on the second floor and stackable washer and dryer in the basement, shelving in storage room in the basement off of the recreation room/ movie room.
  • Section: 3
  • Lot Number: 108

Listed by CENTURY 21 New Millennium, Sharon L Cox

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Listing agent

— 21060 Woodmere Dr —

  • Sharon L Cox

    CENTURY 21 New Millennium

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 21060 Woodmere Dr

School District:St. Marys County Public Schools
NameGradesDistance
Leonardtown Elementary School
22885 Duke Street, Leonardtown, MD 20650
PK-54 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-81.9 mi
Leonardtown High School
23995 Point Lookout Road, Leonardtown, MD 20650
9-121.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 21060 Woodmere Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/12/2025
Listed
$565,000
73.85%
MLS
3/04/2004
Sold
$325,000
—
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 21060 Woodmere Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$4,216
—
$453,000
6%
2023
$4,216
—
$428,900
6%
2023
$4,216
15%
$404,800
6%
2022
$3,654
3%
$380,700
2%
2019
$3,554
-7%
$374,233
2%
2021
$3,834
2%
$367,767
2%
2020
$3,767
—
$361,300
—
2019
$3,765
1%
$361,300
—
2018
$3,746
-3%
$361,300
-2%
2017
$3,856
4%
$370,500
3%
2016
$3,701
4%
$359,367
3%
2015
$3,545
2%
$348,233
3%
2014
$3,491
—
$337,100
—
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 CENTURY 21 New Millennium, Sharon L Cox

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21060 Woodmere Drive, Leonardtown, MD 20650 (MLS# MDSM2028504) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 21060 Woodmere Drive is currently listed for $565,000 and was received on December 12, 2025. Want to learn more about 21060 Woodmere 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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