**Highest & Best offer deadline of 10/29 at Noon!** RARE LEONARDTOWN INVESTMENT OPPORTUNITY ON 1.54 ACRES Bring your vision and unlock the incredible potential of this rare 1.54-acre property in one of Southern Maryland's most sought-after locations. The existing home sustained fire damage and is being sold as-is, presenting a unique opportunity for investors, builders, contractors, or buyers looking for the perfect place to renovate or build their dream home. Large parcels this close to the heart of Leonardtown are becoming increasingly difficult to find. With over an acre and a half of land, mature trees, and plenty of space for privacy, the possibilities are endless. Whether you choose to restore the existing home or start fresh, this property offers an exceptional canvas in a location where demand continues to grow. Just minutes from the charming streets of historic downtown Leonardtown, you'll enjoy locally owned restaurants, coffee shops, boutiques, wineries, breweries, waterfront parks, live music, festivals, and the scenic Leonardtown Wharf overlooking Breton Bay. Outdoor enthusiasts will appreciate nearby boating, fishing, kayaking, and hiking, while commuters will love the convenient access to NAS Patuxent River, MedStar St. Mary's Hospital, and the many employers throughout Southern Maryland. Properties with this combination of acreage, location, and investment potential rarely come to market. Whether you're looking for your next renovation project, a custom homesite, or a long-term investment in one of Southern Maryland's fastest-growing and most desirable communities, this is an opportunity you won't want to miss. Bring your imagination and transform this property into something truly exceptional. Seller prefers to use Interstate Title.
Pending
$79,900
21944 Point Lookout Rd, Leonardtown, MD 20650
0beds
0baths
1,542sqft
Single Family Residence
Built in 1930
1.54 Acres Lot
$-- Zestimate®
$52/sqft
$-- HOA
What's special
Mature trees
- 14 days
- 747
- 44
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Mark Frisco Jr. 443-532-8776,
CENTURY 21 New Millennium 4439689595
Source: Bright MLS,MLS#: MDSM2032976
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 0
- Bathrooms: 0
Basement
- Area: 276
Heating
- None
Cooling
- None
Features
- Has basement: No
- Number of fireplaces: 1
Interior area
- Total structure area: 1,818
- Total interior livable area: 1,542 sqft
- Finished area above ground: 1,542
- Finished area below ground: 0
Property
Parking
- Parking features: Driveway, Off Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: One and One Half
- Stories: 1.5
- Pool features: None
Lot
- Size: 1.54 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1902002604
- Zoning: RPD
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Other
- Foundation: Block
Condition
- New construction: No
- Year built: 1930
Utilities & green energy
- Sewer: Septic Exists
- Water: Well
- Utilities for property: Cable
Community & HOA
Community
- Subdivision: None Available
HOA
- Has HOA: No
Location
- Region: Leonardtown
Financial & listing details
- Price per square foot: $52/sqft
- Tax assessed value: $123,533
- Annual tax amount: $1,166
- Date on market: 10/23/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 10/31/2026 | Pending sale | $79,900$52/sqft |
Source: | ||
| 10/23/2026 | Listed for sale | $79,900-68.3%$52/sqft |
Source: | ||
| 6/15/2022 | Sold | $252,000+0.8%$163/sqft |
Source: | ||
| 5/26/2022 | Contingent | $249,900$162/sqft |
Source: | ||
| 4/26/2022 | Listing removed | $249,900$162/sqft |
Source: | ||
| 4/22/2022 | Pending sale | $249,900+56.2%$162/sqft |
Source: | ||
| 10/8/2014 | Sold | $160,000-3%$104/sqft |
Source: Public Record Report a problem | ||
| 7/16/2014 | Pending sale | $164,900$107/sqft |
Source: CENTURY 21 New Millennium #SM8362167 Report a problem | ||
| 7/1/2014 | Price change | $164,900-8.3%$107/sqft |
Source: CENTURY 21 New Millennium #SM8362167 Report a problem | ||
| 6/6/2014 | Listed for sale | $179,900-48.6%$117/sqft |
Source: CENTURY 21 New Millennium #SM8362167 Report a problem | ||
| 9/18/2013 | Listing removed | $349,900$227/sqft |
Source: CENTURY 21 New Millennium #SM8064814 Report a problem | ||
| 4/27/2013 | Listed for sale | $349,900$227/sqft |
Source: Century 21 New Millennium #SM8064814 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,378 -36.9% | $121,500 -46.6% |
| 2024 | $2,184 +14% | $227,500 +14% |
| 2023 | $1,915 +16.3% | $199,500 +16.3% |
| 2022 | $1,646 +1.1% | $171,500 +1.1% |
| 2021 | $1,628 +1.1% | $169,633 +1.1% |
| 2020 | $1,610 +1.1% | $167,767 +1.1% |
| 2019 | $1,592 | $165,900 |
| 2018 | $1,592 -0.9% | $165,900 |
| 2017 | $1,608 -14.6% | $165,900 -0.5% |
| 2016 | $1,883 | $166,700 |
| 2015 | $1,883 | $166,700 -0.5% |
| 2014 | $1,883 | $167,600 -2.7% |
| 2013 | -- | $172,200 -0.4% |
| 2012 | -- | $172,900 |
| 2011 | -- | $172,900 -22.9% |
| 2010 | -- | $224,250 +13.8% |
| 2009 | -- | $197,112 +16% |
| 2008 | -- | $169,976 +19% |
| 2007 | -- | $142,840 +11% |
| 2006 | -- | $128,702 +12.3% |
| 2005 | -- | $114,566 +14.1% |
| 2004 | -- | $100,430 +2.2% |
| 2003 | -- | $98,292 +2.2% |
| 2002 | -- | $96,156 +2.3% |
| 2001 | -- | $94,020 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 20650
Nearby schools
Schools provided by the listing agent
- Elementary: Leonardtown
- Middle: Leonardtown
- High: Leonardtown
- District: St. Mary's 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.






