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21039 WOODMERE DRIVE, Leonardtown, MD 20650


Sold For: 580000

Sold on: Jan 8th, 2026
$ Per Square Foot: $141.05
Beds: 5
Baths: 2 full 1 partial

Comments for 21039 WOODMERE DRIVE, Leonardtown, MD 20650

****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!

Accessibility: Above Grade, Below Grade Heating: Heat Pump(s)
Additional Structures: 2+ Access Exits Interior: 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-
Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Icemaker, Microwave, Oven/Range - Electric, Range Hood, Refrigerator, Stainless Steel Appliances, Washer, Water Heater Lot Description: Backs to Trees, Private, Rear Yard, Secluded, SideYard(s), Trees/Wooded
Basement: Connecting Stairway, Heated, Improved, Interior Access, Outside Entrance, Partially Finished, Side Entrance, Walkout Stairs Lot Dimensions: 1.17 Acre(S)
Basement: Yes Lot Features: Backs to Trees, Private, Rear Yard, Secluded, SideYard(s), Trees/Wooded
Cooling: Central A/C, Ceiling Fan(s) Lot Size: 1.17 Acres
Days on Market: 108 Parking Notes: Asphalt Driveway, Lighted Parking, Paved Driveway, Pr
Exterior: Exterior Lighting, Flood Lights, Gutter System, Secure Storage, Sidewalks, Other Roof Type: Shingle
Exterior: Vinyl Siding Sewer: Private Septic Tank
Fencing Description: Partially, Rear Taxes: $4,054
Fireplace: Gas/Propane, Heatilator, Mantel(s) Water: Public
Fireplaces: 1 Windows: Casement, Double Pane, Insulated, Screens, Sliding
Flooring: Carpet, Hardwood, Vinyl Wooded: Yes
Fuel Type: Central, Electric Year Built: 1999
Garage: 2  
High School: LEONARDTOWN
Middle School: LEONARDTOWN
School District: ST MARYS COUNTY PUBLIC SCHOOLS

Listed By

Agency Name: RE/MAX Realty Group
Agency Phone: 3018849493

Shown By

Agent Name: The Rick Shaffer Team
Agent Phone: (717) 455-7425
Agency Title: Berkshire Hathaway HomeServices Homesale Realty

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/01/2026. The listing information on this page last changed on 04/01/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 04/01/2026 12:00:28 AM EST) or Bright MLS (last updated Tue 03/31/2026 11:49:52 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agent License Information: 
Licensed in Pennsylvania
The Rick Shaffer Team
Rickey Shaffer, Travis Shaffer, Austin Shaffer, Richard Vangel, Amanda Croumer, Alexis Moore  

1680 Kenneth Road, York, PA 17408
717-757-7811

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