Date
Details
Price
Change
Source
2/27/2026
Listed
$500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$500,000 Coming Soon
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Property Description
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.
Full Property Details
Full Property Details for 20798 Waterside Dr
General
- Price: $500,000
- Taxes: $3,220 (2025)
- Status: Coming Soon
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDSM2029666
- Updated: 2/27/2026
- Added to Site: 1 day(s) ago
- Expected Market Date: 3/13/2026
Interior
- Rooms/Areas: Living Room, Dining Room, Bedroom 2, Kitchen, Bedroom 1, Sun/Florida Room, Laundry
- Interior Features: Floor Plan - Traditional, Entry Level Bedroom, Combination Kitchen/Living
- Appliances: Refrigerator, Stove, Washer, Dryer
- Flooring: Hardwood, Vinyl, Wood
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
- Main Floor Baths: 1
- Main - Full Baths: 1
Bedrooms
- Total Bedrooms: 2
- Bedrooms Main & Up: 2
Parking
- Parking Type: Driveway
Location
- County: SAINT MARYS
- Subdivision: BRUBACHERS
- Driving Directions: From Leonardtown, Turn onto Medleys Neck Rd, Turn (R) onto Breton Beach Rd, Turn (R) Waterside Dr, House is straight ahead. #20798 Waterside Dr
School Information
- School District: St. Marys County Public Schools
- Middle School: Leonardtown
- High School: Leonardtown
Community
- Pets Allowed: Yes
- Pets: Cats OK, Dogs OK
Heating & Cooling
- Cooling Type: Wall Unit
- Cooling Fuel: Electric
- Heating Type: Forced Air, Other
- Heating Fuel: Oil, Propane - Owned
- Water Heater: Electric
Utilities
- Sewer: Septic Exists
- Water: Well
- Utility Description: Cable TV Available
Structural Information
- Architectural Style: Bungalow
- Structure Type: Detached
- Construction: Stucco
- Foundation: Slab
- Roof: Asphalt
- Stories Description: Main
- Square Feet: 1,018
- Sq. Ft. Source: Estimated
- Living Area: 1,018 Sq. Ft.
- Finished Above Grnd: 1,018 Sq. Ft.
- Year Built: 1950
- Year Built Source: Assessor
Lot Features
- Property View: River
- Lot Size (Acres): 0.18
- Lot Size (Sq. Ft.): 7,893
- Lot Size Source: Assessor
- Zoning: RPD
- Lot Description: Cleared, No Thru Street
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Access Desc: Boat - Powered, Fishing Allowed, Personal Watercraft (PWC), Private Access, Swimming Allowed, Waterski/Wakeboard
- Water Front Type: River
- Water Front Name: Potomac River
Financial Considerations
- Price Per Sq. Ft.: $491.16
- Assessment Year: 2026
- County Tax: $3,220
- County Tax Freq: Annually
- Tax w/Assessment: $341,067
- Tax Amount: $3,220
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 816
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 2
Listed by RE/MAX One, Connie M. Fitzgerald and RE/MAX One, Michael Fitzgerald, II
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 20798 Waterside Dr —
Connie M. Fitzgerald
RE/MAX One
Michael Fitzgerald, II
RE/MAX One
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 20798 Waterside Dr
School District:St. Marys County Public Schools
| Name | Grades | Distance |
|---|---|---|
Leonardtown Elementary School 22885 Duke Street, Leonardtown, MD 20650 | PK-5 | 4.7 mi |
Leonardtown Middle School 24015 Point Lookout Road, Leonardtown, MD 20650 | 6-8 | 4.7 mi |
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650 | 9-12 | 4.7 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 20798 Waterside Dr
Tax History
Tax History for 20798 Waterside Dr
Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,478
—
$335,500
1%
2023
$3,478
—
$330,867
1%
2023
$3,478
13%
$326,233
1%
2022
$3,087
-2%
$321,600
—
2019
$3,157
-8%
$321,367
—
2021
$3,420
—
$321,133
—
2020
$3,416
—
$320,900
—
2019
$3,414
1%
$320,900
—
2018
$3,395
-1%
$320,900
—
2017
$3,419
1%
$321,800
—
2016
$3,381
3%
$321,800
—
2015
$3,276
-10%
$321,800
-6%
2014
$3,620
—
$343,900
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 20798 Waterside Dr
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 3Total Baths
- 2,448Sq. Ft.
- Single Family
- Active
- Updated 1 hour ago
- 2Beds
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- Single Family
- Active
- Updated 1 day ago
- 4Beds
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- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 2,587Sq. Ft.
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- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 4Total Baths
- 2,544Sq. Ft.
- Townhouse
- Active
- Updated 1 day ago
- 3Beds
- 3Total Baths
- 1,160Sq. Ft.
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- Single Family
- Closed
- Updated 15 hours ago
- 4Beds
- 3Total Baths
- 3,090Sq. Ft.
20798 Waterside Drive, Leonardtown, MD 20650 (MLS# MDSM2029666) is a Single Family property with 2 bedrooms and 1 full bathroom. 20798 Waterside Drive is currently listed for $500,000 and was received on February 27, 2026. Want to learn more about 20798 Waterside Drive? Do you have questions about finding other Single Family real estate for sale in Leonardtown? You can browse all Leonardtown real estate or contact a Coldwell Banker agent to request more information.