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$580,000
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Property Description
****Under Contract with a HOME SALE contingency**** Nestled on a beautiful 1.17 acre lot in the Leonardtown neighborhood of Wilderness Run. This spacious and well-maintained Colonial style home offers privacy and convenience, surrounded by trees with an open yard and a fully fenced side and backyard. Enjoy outdoor living on the rear deck and the ease of a two-car front-load garage with automatic openers, plus a gutter guard system for low-maintenance living. Inside, the main level features a welcoming foyer, formal dining room, and a formal living room with gas fireplace and mantle. The expansive family room opens to a country-style kitchen with table space, a pantry, granite countertops, breakfast bar, stainless steel appliances, and access to the rear deck and fenced rear yard-perfect for entertaining. There is also a main-level flex room perfect for home office or guest bedroom and it is located off the center hall with pocket door entry along with the guest powder room. Upstairs, the spacious primary suite includes multiple closets, including a walk-in, and a beautifully renovated ensuite bathroom with a frameless glass walk-in tile shower with beautiful picture window, a dual-sink vanity, and natural light. Additionally, the primary boasts a separate sitting room for relaxation. Three additional generously-sized bedrooms share the full central hallway bath with spacious dual-sink vanity along with a private bath room with shower/soaking tub combo. For added convenience, the laundry room is also located in this upper level near the bedrooms. The finished lower level includes an oversized rec room with built-ins, a large storage room, and a versatile flex space. A covered walk-up provides access to the side and rear yards with a separate dog play yard. Recent upgrades include.... New Roof shingles installed Dec. 2022, New A/C and Heat Pump installed September 2023, New 73 Gallon HWH installed in 2017, and Septic pumped in 2023. Additionally, this home comes with the GENERAC whole home auto- generator system. This neighborhood is conveniently located just minutes from downtown Leonardtown, and offers easy access to shopping, dining, nightlife, and the waterfront at Leonardtown Wharf. Nearby attractions include parks, beaches, trails, boardwalks, wineries, theaters, museums, and all that beautiful historic St. Mary's County has to offer. NO HOA!
Full Property Details
Full Property Details for 21039 Woodmere Dr
General
- Sold For: $580,000
- Taxes: $4,054 (2024)
- Status: Closed
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDSM2027164
- Added to Site: 117 day(s) ago
Interior
- Interior Features: Attic, Bathroom - Soaking Tub, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Carpet, Ceiling Fan(s), Chair Railings, Crown Moldings, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Country, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Window Treatments, Wood Floors, Other
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Gas/Propane, Heatilator, Mantel(s)
- Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Icemaker, Microwave, Oven/Range - Electric, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
- Flooring: Carpet, Hardwood, Vinyl
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: 4
- Bedrooms Main & Up: 1
Other Rooms
- Laundry: Has Laundry
Additional Information
- Security/Safety: Non-Monitored, Security System, Smoke Detector
Exterior
- Exterior Features: Exterior Lighting, Flood Lights, Gutter System, Secure Storage, Sidewalks, Other
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 8
- Parking Features: Asphalt Driveway, Lighted Parking, Paved Driveway, Private
- Parking Type: Attached Garage, Driveway
- Garage Description: Garage - Front Entry, Garage Door Opener, Inside Access
Location
- County: SAINT MARYS
- Subdivision: WILDERNESS CLUST
- Driving Directions: From MD Rt 5 South Turn onto Wilderness Road to a left onto Woodmere Dr. to driveway on right at 21039 Woodmere Dr.
School Information
- School District: St. Marys County Public Schools
- Middle School: Leonardtown
- High School: Leonardtown
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C, Ceiling Fan(s)
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Central, Electric
- Water Heater: Electric, 60+ Gallon Tank
Utilities
- Sewer: Private Septic Tank
- Water: Public
Structural Information
- Architectural Style: Colonial
- Structure Type: Detached
- Construction: Vinyl Siding
- Basement: Yes
- Basement Entrance: Yes
- Basement Desc.: Connecting Stairway, Heated, Improved, Interior Access, Outside Entrance, Partially Finished, Side Entrance, Walkout Stairs
- Foundation: Slab
- Roof: Shingle
- Walls/Ceilings: 9'+ Ceilings, Dry Wall
- Windows: Casement, Double Pane, Insulated, Screens, Sliding
- Stories Description: Main, Upper 1
- Square Feet: 4,112
- Sq. Ft. Source: Estimated
- Living Area: 4,112 Sq. Ft.
- Finished Above Grnd: 2,788 Sq. Ft.
- Finished Below Grnd: 1,324 Sq. Ft.
- Year Built: 1999
- Year Built Source: Assessor
- Property Condition: Very Good
Additional Structures
- Other Structures: Shed
Lot Features
- Lot Size (Acres): 1.17
- Lot Size (Sq. Ft.): 50,965
- Lot Size Source: Assessor
- Zoning: RNC
- Lot Description: Backs to Trees, Private, Rear Yard, Secluded, SideYard(s), Trees/Wooded
- Fencing (Description): Partially, Rear
Financial Considerations
- Price Per Sq. Ft.: $208.03
- Assessment Year: 2025
- County Tax: $4,054
- County Tax Freq: Annually
- Tax w/Assessment: $445,900
- Tax Amount: $4,054
- Tax Year: 2024
- Terms: Standard Sale
- Tax Total Finished Sq. Ft.: 2788
Disclosures and Reports
- Ownership: Fee Simple
- Section: 3
- Lot Number: 64
Listed by RE/MAX Realty Group, Wayne A Floyd
Sold by Berkshire Hathaway HomeServices PenFed Realty, Steven M Carroll
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Schools
Schools serving 21039 Woodmere Dr
School District:St. Marys County Public Schools
| Name | Grades | Distance |
|---|---|---|
Leonardtown Elementary School 22885 Duke Street, Leonardtown, MD 20650 | PK-5 | 3.9 mi |
Leonardtown Middle School 24015 Point Lookout Road, Leonardtown, MD 20650 | 6-8 | 1.9 mi |
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650 | 9-12 | 1.6 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 21039 Woodmere Dr
Date
Details
Price
Change
Source
1/08/2026
Sold
$580,000
—
MLS
9/29/2025
Price Reduced
$580,000
-2.52%
MLS
9/22/2025
Listed
$595,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
21039 Woodmere Drive, Leonardtown, MD 20650 (MLS# MDSM2027164) is a Single Family property that was sold at $580,000 on January 08, 2026. Want to learn more about 21039 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.

