****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!
Sold for $580,000
$580,000
21039 Woodmere Dr, Leonardtown, MD 20650
5beds
4,112sqft
Single Family Residence
Built in 1999
1.17 Acres Lot
$588,700 Zestimate®
$141/sqft
$3,065 Estimated rent
Home value
$588,700
$542,000 - $642,000
$3,065/mo
Zestimate® history
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$3,502/mo
Est. payment
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List your homeWhat's special
Home officeGas fireplaceAutomatic openersFinished lower levelPrivate bath roomTwo-car front-load garageRenovated ensuite bathroom
Zillow last checked:
Listing updated:
Listed by:
Wayne Floyd 410-610-8089,
RE/MAX Realty Group,
Listing Team: Floyd Home Team With Re/Max 100
Bought with:
Steve Carroll, 0225267528
Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS,MLS#: MDSM2027164
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
- Main level bedrooms: 1
Basement
- Area: 1324
Heating
- Heat Pump, Central, Electric
Cooling
- Central Air, Ceiling Fan(s), Electric
Appliances
- Included: Dishwasher, Disposal, Dryer, Exhaust Fan, Ice Maker, Microwave, Oven/Range - Electric, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Electric Water Heater
- Laundry: Has Laundry
Features
- Attic, Soaking Tub, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Ceiling Fan(s), Chair Railings, Crown Molding, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Traditional, Formal/Separate Dining Room, Eat-in Kitchen, Kitchen - Country, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Other, 9'+ Ceilings, Dry Wall
- Flooring: Carpet, Hardwood, Vinyl, Wood
- Windows: Casement, Double Pane Windows, Insulated Windows, Screens, Sliding, Window Treatments
- Basement: Connecting Stairway,Heated,Improved,Interior Entry,Exterior Entry,Partially Finished,Side Entrance,Walk-Out Access
- Number of fireplaces: 1
- Fireplace features: Gas/Propane, Heatilator, Mantel(s)
Interior area
- Total structure area: 4,112
- Total interior livable area: 4,112 sqft
- Finished area above ground: 2,788
- Finished area below ground: 1,324
Property
Parking
- Total spaces: 8
- Parking features: Garage Faces Front, Garage Door Opener, Inside Entrance, Asphalt, Lighted, Driveway, Private, Attached
- Attached garage spaces: 2
- Uncovered spaces: 6
Accessibility
- Accessibility features: 2+ Access Exits
Features
- Levels: Three
- Stories: 3
- Exterior features: Lighting, Flood Lights, Rain Gutters, Storage, Sidewalks, Other
- Pool features: None
- Fencing: Partial,Back Yard
Lot
- Size: 1.17 Acres
- Features: Backs to Trees, Private, Rear Yard, Secluded, SideYard(s), Wooded
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1903050122
- Zoning: RNC
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Slab
- Roof: Shingle
Condition
- Very Good
- New construction: No
- Year built: 1999
Utilities & green energy
- Sewer: Private Septic Tank
- Water: Public
Community & HOA
Community
- Security: Non-Monitored, Security System, Smoke Detector(s)
- Subdivision: Wilderness Clust
HOA
- Has HOA: No
Location
- Region: Leonardtown
Financial & listing details
- Price per square foot: $141/sqft
- Tax assessed value: $445,900
- Annual tax amount: $4,054
- Date on market: 9/22/2025
- Listing agreement: Exclusive Right To Sell
- Listing terms: Assumable,Cash,Conventional,FHA,Negotiable,VA Loan,Other
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 1/8/2026 | Sold | $580,000$141/sqft |
Source:  Bright MLS #MDSM2027164 Report a problem | ||
| 12/18/2025 | Pending sale | $580,000$141/sqft |
Source: Bright MLS #MDSM2027164 Report a problem | ||
| 11/10/2025 | Contingent | $580,000$141/sqft |
Source: Bright MLS #MDSM2027164 Report a problem | ||
| 9/29/2025 | Price change | $580,000-2.5%$141/sqft |
Source: Bright MLS #MDSM2027164 Report a problem | ||
| 9/22/2025 | Listed for sale | $595,000+169.8%$145/sqft |
Source: Bright MLS #MDSM2027164 Report a problem | ||
| 2/26/1999 | Sold | $220,500$54/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,564 +12.6% | $445,900 +5.6% |
| 2024 | $4,054 +5.9% | $422,367 +5.9% |
| 2023 | $3,828 +6.3% | $398,833 +6.3% |
| 2022 | $3,602 +1.1% | $375,300 +1.1% |
| 2021 | $3,563 +1.1% | $371,200 +1.1% |
| 2020 | $3,523 +1.1% | $367,100 +1.1% |
| 2019 | $3,484 | $363,000 |
| 2018 | $3,484 -0.9% | $363,000 |
| 2017 | $3,517 +3.6% | $363,000 -2.5% |
| 2016 | $3,396 | $372,200 +2.5% |
| 2015 | $3,396 | $363,233 +2.5% |
| 2014 | $3,396 | $354,267 +2.6% |
| 2013 | -- | $345,300 |
| 2012 | -- | $345,300 |
| 2011 | -- | $345,300 -11.7% |
| 2010 | -- | $391,230 +6.6% |
| 2009 | -- | $366,872 +7.1% |
| 2008 | -- | $342,516 +7.7% |
| 2007 | -- | $318,160 +10% |
| 2006 | -- | $289,230 +11.1% |
| 2005 | -- | $260,300 +12.5% |
| 2004 | -- | $231,370 +1.4% |
| 2003 | -- | $228,122 +1.4% |
| 2002 | -- | $224,876 +1.5% |
| 2001 | -- | $221,630 |
Find assessor info on the county website
Neighborhood: 20650
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Nearby schools
GreatSchools rating
- 7/10Leonardtown Elementary SchoolGrades: PK-5Distance: 3.9 mi
- 8/10Leonardtown Middle SchoolGrades: 6-8Distance: 1.9 mi
- 5/10Leonardtown High SchoolGrades: 9-12Distance: 1.6 mi
Schools provided by the listing agent
- Middle: Leonardtown
- High: Leonardtown
- District: St. Marys County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$588,700
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Estimated market value
$588,700
- Maryland
- Saint Marys County
- Leonardtown
- 20650
- 21039 Woodmere Dr
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