Pending
Sale Pending at 21039 Woodmere Dr, Leonardtown, MD 20650 | MLS# MDSM2027164 | Listing updated on 2026-01-01
Photo 1 of Sale Pending at 21039 Woodmere Dr, Leonardtown, MD 20650 | MLS# MDSM2027164 | Listing updated on 2026-01-01
Photo 2 of Sale Pending at 21039 Woodmere Dr, Leonardtown, MD 20650 | MLS# MDSM2027164 | Listing updated on 2026-01-01
Photo 3 of Sale Pending at 21039 Woodmere Dr, Leonardtown, MD 20650 | MLS# MDSM2027164 | Listing updated on 2026-01-01
Photo 4 of Sale Pending at 21039 Woodmere Dr, Leonardtown, MD 20650 | MLS# MDSM2027164 | Listing updated on 2026-01-01
56+
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Street View

$580,000

Monthly Est:$2,887

  • Beds Icon5 Beds
  • Beds Icon
    3 Baths
  • Beds Icon4,112sqft

21039 Woodmere Dr, Leonardtown, MD 20650

$2,887/moEst:

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  • Single Family Residence

  • Built in 1999

  • $-- HOA

  • 1.17 acres lot

  • $141/sq.ft

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!

  • Houzeo last checked: 1 minute ago
  • Listing updated: January 1, 2026 at 8:07 pm
  • Listing Provided by: Wayne A Floyd (410) 610-8089 | RE/MAX Realty Group (301) 884-9493
  • Source: Bright MLS-NJ | MLS#: MDSM2027164 Bright MLS-NJ

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Saint Marys Md County

  • City

    Leonardtown

  • Neighborhood

    --

  • Year Built

    1999

  • HOA Fees

    -

  • Finished Area

    4,112 sqft

  • Lot Size

    1.17 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDSM2027164

  • MLS Status

    PENDING-BRIGHT

  • Days on Market

    50

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 3

Interior

  • Exterior Features

    Exterior Lighting, Flood Lights, Gutter System, Secure Storage, Sidewalks, Other

  • Window Features

    Casement, Double Pane Windows, Insulated, Screens, Sliding

  • Appliances

    Dishwasher, Disposal, Dryer, Exhaust Fan, Icemaker, Microwave, Oven/range Electric, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater

  • Cooling

    Central A/c, Ceiling Fan(s)

  • 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

  • Sewer

    Private Septic Tank

  • Heating

    Heat Pump(s)

  • Flooring

    Carpet, Hardwood, Vinyl

Construction

  • Year Built

    Year Built: 1999

  • Home type

    Single Family Residence

  • Foundation Details

    Slab

  • Architectural Style

    Colonial

  • Property Condition

    Very Good

  • Construction Materials

    Vinyl Siding

  • Roof

    Shingle

Utilities & Energy

  • Basement

    Connecting Stairway, Heated, Improved, Interior Access, Outside Entrance, Partially Finished, Side Entrance, Walkout Stairs

  • Water Source

    Public

  • Security Features

    Non Monitored, Security System, Smoke Detector

  • Parking Features

    Asphalt Driveway, Lighted Parking, Paved Driveway, Private

  • Fireplace Features

    Gas/propane, Heatilator, Mantel(s)

Other Features

  • Lot Features

    Backs To Trees, Private, Rear Yard, Secluded, Side Yard(s), Trees/wooded

  • Subdivision Name

    Wilderness Clust

Price History

DateEventPrice

12/18/2025

Source: mls_logoBright MLS-NJ #MDSM2027164

Pending

$580,000

$141/sqft

11/10/2025

Source: mls_logoBright MLS-NJ #MDSM2027164

Contingent (Active Under Contract)

$580,000

$141/sqft

09/29/2025

Source: mls_logoBright MLS-NJ #MDSM2027164

Price Decreased

$580,000 -2.52%

$141/sqft

09/22/2025

Source: mls_logoBright MLS-NJ #MDSM2027164

Price Increased

$595,000 +2.59%

$145/sqft

09/22/2025

Source: mls_logoBright MLS-NJ #MDSM2027164

Listed for Sale

$580,000

$141/sqft

Nearby Homes

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