Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiast’s paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include: ✔ Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide ✔ Seawall refurbished in 2020 for added shoreline protection ✔ Private pier with an electric boat lift—perfect for boating adventures Includes additional lot across the street .177 acres, If you decide to not include it in the sale %50,000 price reduction will be given by sellers. Don’t miss this rare chance to own a piece of paradise with endless potential. Whether you’re looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see! Currently listed on Air B&B and VRBO.
For sale
$500,000
20798 Waterside Dr, Leonardtown, MD 20650
2beds
1,018sqft
Est.:
Single Family Residence
Built in 1950
7,893 Square Feet Lot
$393,200 Zestimate®
$491/sqft
$-- HOA
What's special
- 2 days |
- 378 |
- 4 |
Zillow last checked: 7 hours ago
Listing updated: March 12, 2026 at 05:16pm
Listed by:
Connie Fitzgerald 301-672-1634,
RE/MAX One 4105356291,
Co-Listing Agent: Michael Fitzgerald, Ii 301-672-0765,
RE/MAX One
Source: Bright MLS,MLS#: MDSM2029666
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
- Main level bathrooms: 1
- Main level bedrooms: 2
Rooms
- Room types: Living Room, Dining Room, Bedroom 2, Kitchen, Bedroom 1, Sun/Florida Room, Laundry
Bedroom 1
- Features: Flooring - HardWood
- Level: Main
Bedroom 2
- Features: Flooring - HardWood
- Level: Main
Dining room
- Features: Flooring - HardWood
- Level: Main
Kitchen
- Level: Main
Laundry
- Level: Main
Living room
- Features: Flooring - HardWood
- Level: Main
Other
- Features: Flooring - Vinyl
- Level: Main
Heating
- Forced Air, Other, Oil, Propane
Cooling
- Wall Unit(s), Electric
Appliances
- Included: Refrigerator, Cooktop, Washer, Dryer, Electric Water Heater
- Laundry: Laundry Room
Features
- Floor Plan - Traditional, Entry Level Bedroom, Combination Kitchen/Living
- Flooring: Hardwood, Vinyl, Wood
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,018
- Total interior livable area: 1,018 sqft
- Finished area above ground: 1,018
- Finished area below ground: 0
Property
Parking
- Parking features: Driveway
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: One
- Stories: 1
- Pool features: None
- Has view: Yes
- View description: River
- Has water view: Yes
- Water view: River
- Waterfront features: Boat - Powered, Fishing Allowed, Personal Watercraft (PWC), Private Access, Swimming Allowed, Waterski/Wakeboard, River
- Body of water: Potomac River
- Frontage length: Water Frontage Ft: 50
Lot
- Size: 7,893 Square Feet
- Features: Cleared, No Thru Street
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1903021165
- Zoning: RPD
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Bungalow
- Property subtype: Single Family Residence
Materials
- Stucco
- Foundation: Slab
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1950
Utilities & green energy
- Sewer: Septic Exists
- Water: Well
- Utilities for property: Cable Available
Community & HOA
Community
- Subdivision: Brubachers
HOA
- Has HOA: No
Location
- Region: Leonardtown
Financial & listing details
- Price per square foot: $491/sqft
- Tax assessed value: $341,067
- Annual tax amount: $3,220
- Date on market: 3/13/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
Estimated market value
$393,200
$334,000 - $452,000
$1,584/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/13/2026 | Listed for sale | $500,000+11.1%$491/sqft |
Source:  Bright MLS #MDSM2029666 Report a problem | ||
| 12/8/2025 | Listing removed | $450,000$442/sqft |
Source: Bright MLS #MDSM2027780 Report a problem | ||
| 10/17/2025 | Listed for sale | $450,000$442/sqft |
Source: Bright MLS #MDSM2027780 Report a problem | ||
| 10/1/2025 | Listing removed | $450,000$442/sqft |
Source: Bright MLS #MDSM2022922 Report a problem | ||
| 3/6/2025 | Listed for sale | $450,000-6.2%$442/sqft |
Source: Bright MLS #MDSM2022922 Report a problem | ||
| 8/23/2024 | Listing removed | $479,500$471/sqft |
Source: Bright MLS #MDSM2019518 Report a problem | ||
| 7/23/2024 | Price change | $479,500-4.1%$471/sqft |
Source: Bright MLS #MDSM2019518 Report a problem | ||
| 6/21/2024 | Listed for sale | $500,000+5.3%$491/sqft |
Source: Bright MLS #MDSM2019518 Report a problem | ||
| 1/1/2024 | Listing removed | -- |
Source: Bright MLS #MDSM2012020 Report a problem | ||
| 9/15/2023 | Listed for sale | $475,000$467/sqft |
Source: Bright MLS #MDSM2012020 Report a problem | ||
| 9/1/2023 | Listing removed | $475,000$467/sqft |
Source: Bright MLS #MDSM2012020 Report a problem | ||
| 5/6/2023 | Price change | $475,000-0.8%$467/sqft |
Source: Bright MLS #MDSM2012020 Report a problem | ||
| 3/3/2023 | Listed for sale | $479,000$471/sqft |
Source: Bright MLS #MDSM2012020 Report a problem | ||
| 12/2/2022 | Listing removed | -- |
Source:  RE/MAX International Report a problem | ||
| 8/13/2022 | Price change | $479,000-11.1%$471/sqft |
Source: Bright MLS #MDSM2007786 Report a problem | ||
| 6/10/2022 | Price change | $539,000+12.5%$529/sqft |
Source: Bright MLS #MDSM2007786 Report a problem | ||
| 3/16/2022 | Price change | $479,000+9.1%$471/sqft |
Source: Bright MLS #MDSM2001640 Report a problem | ||
| 2/10/2022 | Price change | $439,000+0.9%$431/sqft |
Source: Bright MLS #MDSM2001640 Report a problem | ||
| 2/9/2022 | Price change | $435,000+2.4%$427/sqft |
Source: Bright MLS #MDSM2001640 Report a problem | ||
| 8/27/2021 | Price change | $425,000+9.3%$417/sqft |
Source: Bright MLS #MDSM2001640 Report a problem | ||
| 6/16/2021 | Price change | $389,000-8.5%$382/sqft |
Source: Owner Report a problem | ||
| 6/8/2021 | Price change | $425,000+9.3%$417/sqft |
Source: Owner Report a problem | ||
| 6/2/2021 | Price change | $389,000-18.6%$382/sqft |
Source: Owner Report a problem | ||
| 5/24/2021 | Listed for sale | $478,000+705%$470/sqft |
Source: Bright MLS #MDSM176578 Report a problem | ||
| 5/7/2021 | Listing removed | -- |
Source:  Berkshire Hathaway HomeServices Report a problem | ||
| 9/30/2002 | Sold | $59,378$58/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,754 +18.2% | $335,500 +1.4% |
| 2024 | $3,176 +1.4% | $330,867 +1.4% |
| 2023 | $3,131 +1.4% | $326,233 +1.4% |
| 2022 | $3,087 +0.1% | $321,600 +0.1% |
| 2021 | $3,084 +0.1% | $321,367 +0.1% |
| 2020 | $3,082 +0.1% | $321,133 +0.1% |
| 2019 | $3,080 | $320,900 |
| 2018 | $3,080 -0.9% | $320,900 |
| 2017 | $3,110 -13.4% | $320,900 -0.3% |
| 2016 | $3,591 | $321,800 |
| 2015 | $3,591 | $321,800 |
| 2014 | $3,591 | $321,800 -6.4% |
| 2013 | -- | $343,900 |
| 2012 | -- | $343,900 |
| 2011 | -- | $343,900 -19.7% |
| 2010 | -- | $428,110 +19.6% |
| 2009 | -- | $358,072 +24.3% |
| 2008 | -- | $288,036 +32.1% |
| 2007 | -- | $218,000 +16.2% |
| 2006 | -- | $187,630 +19.3% |
| 2005 | -- | $157,260 +23.9% |
| 2004 | -- | $126,890 +2.6% |
| 2003 | -- | $123,706 +2.6% |
| 2002 | -- | $120,523 +2.7% |
| 2001 | -- | $117,340 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,763/mo
Principal & interest
$2430
Property taxes
$333
More affordability tools
Climate risks
Neighborhood: 20650
Nearby schools
GreatSchools rating
- 7/10Leonardtown Elementary SchoolGrades: PK-5Distance: 4.7 mi
- 8/10Leonardtown Middle SchoolGrades: 6-8Distance: 4.7 mi
- 5/10Leonardtown High SchoolGrades: 9-12Distance: 4.6 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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