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Dashboard
- 5 Beds
- 2½ Baths
- 4,112 Sqft
- 1.17 Acres
21039 Woodmere Dr
****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!
Essential Information
- MLS® #MDSM2027164
- Price$580,000
- Bedrooms5
- Bathrooms2.50
- Full Baths2
- Half Baths1
- Square Footage4,112
- Acres1.17
- Year Built1999
- TypeResidential
- Sub-TypeDetached
- StyleColonial
- StatusActive Under Contract
Community Information
- Address21039 Woodmere Dr
- SubdivisionWILDERNESS CLUST
- CityLEONARDTOWN
- CountySAINT MARYS-MD
- StateMD
- Zip Code20650
Amenities
- # of Garages2
Amenities
Attic, Bathroom - Soaking Tub, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Carpet, Ceiling Fan(s), Chair Railings, Crown Moldings, Entry Level Bedroom, Formal/Separate Dining Room, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Window Treatments, Wood Floors
Parking
Asphalt Driveway, Lighted Parking, Paved Driveway, Private
Garages
Garage - Front Entry, Garage Door Opener, Inside Access
Interior
- Interior FeaturesFloor Plan - Traditional
- HeatingHeat Pump(s)
- CoolingCentral A/C, Ceiling Fan(s)
- Has BasementYes
- FireplaceYes
- # of Fireplaces1
- Stories3
Appliances
Dishwasher, Disposal, Dryer, Exhaust Fan, Icemaker, Microwave, Oven/Range - Electric, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
Basement
Connecting Stairway, Heated, Improved, Interior Access, Outside Entrance, Partially Finished, Side Entrance, Walkout Stairs
Fireplaces
Gas/Propane, Heatilator, Mantel(s)
Exterior
- ExteriorVinyl Siding
- RoofShingle
- ConstructionVinyl Siding
- FoundationSlab
Exterior Features
Exterior Lighting,Flood Lights,Gutter System,Secure Storage,Sidewalks,Other,Partially,Rear
Lot Description
Backs to Trees, Private, Rear Yard, Secluded, SideYard(s), Trees/Wooded
Windows
Casement, Double Pane, Insulated, Screens, Sliding
School Information
- MiddleLEONARDTOWN
- HighLEONARDTOWN
District
ST. MARYS COUNTY PUBLIC SCHOOLS
Additional Information
- Date ListedSeptember 22nd, 2025
- Days on Market50
- ZoningRNC
Listing Details
- OfficeRE/MAX Realty Group
Price Change History for 21039 Woodmere Dr, LEONARDTOWN, MD (MLS® #MDSM2027164)
| Date | Details | Price | Change |
|---|---|---|---|
| Active Under Contract (from Active) | – | – | |
| Price Reduced (from $595,000) | $580,000 | $15,000 (2.52%) |
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Listing information last updated on November 22nd, 2025 at 6:55pm CST.