20798 Waterside Drive

Leonardtown, MD
$ 450,000 Beds 2 Baths 1 Sq 1,018
Monthly Estimate* How much can I afford?

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 livingwhether its crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiasts 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 liftperfect for boating adventures Dont miss this rare chance to own a piece of paradise with endless potential. Whether youre 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.

ACTIVE

  • Price
  • $ 450,000
  • City
  • Leonardtown
  • Bedrooms
  • 2
  • Full Bathrooms
  • 1
  • County
  • SAINT MARYS
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 0.18 Acres
  • Zip
  • 20650
  • Sqr Footage
  • 1,018
  • Year Built
  • 1950
  • Taxes
  • $ 3220
  • Style
  • Bungalow
  • MLS#
  • MDSM2029666
Listed By: Connie M. Fitzgerald with RE/MAX One - 4105356291;
Data Source: Bright MLS

Features

General

Living Area 1018
Sewer Septic Exists
Heating Forced Air,Other
Cooling Wall Unit
Utilities Cable TV Available
Possession 31-60 Days CD
Roof Asphalt
Appliances Refrigerator,Stove,Washer,Dryer
Zoning RPD
Architectural Style Bungalow
Construction Materials Stucco
School District ST. MARYS COUNTY PUBLIC SCHOOLS
Year Built 1950
View River
Levels 1
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County SAINT MARYS
New Construction No
Property Type Residential
HOA No
Subdivision Name BRUBACHERS
Garage Y/N No
Water Access Y/N Yes
Other Structures Above Grade,Below Grade
Full Baths 1
Status ACTIVE
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
City LEONARDTOWN
Body of Water Potomac River
Disclosures Prop Disclaimer
Senior Community Y/N No
Lot Size Units Square Feet
Lot Size Square Feet 7893.00
Tax Assessed Value 341067.0
Tax Annual Amount 3220.0
Home Warranty Y/N No
Structure Type Detached
Condo/Coop Association fee Y/N No
Bathrooms Full Main Level 1
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 442.04
Acceptable Financing Cash,Conventional
Historic Y/N No
Lease Considered Y/N No
Vacation Rental Y/N Yes
Total SQFT 1018
Standard Status Active
Year Built Source Assessor
Legal Subdivision BRUBACHERS SUBDIVISION
Tax Lot 2
Association Recreation Fee No

Interior Features

Interior Amenities Floor Plan - Traditional,Entry Level Bedroom,Combination Kitchen/Living
Heating Fuel Oil,Propane - Owned
Flooring Hardwood,Vinyl,Wood
Hot Water Electric
Basement (Y/N) No
Heating Y/N Yes
Fireplace Y/N No
Above Grade Finished Area 1018
Central Air Y/N No
Total Bedrooms 2
Room Type Living Room,Dining Room,Bedroom 2,Kitchen,Bedroom 1,Sun/Florida Room,Laundry
Main Level Bedrooms 2
Below Grade Finished Area Unit Type Square Feet
LivingAreaSource Estimated
Below Grade Unfin Area Units Square Feet
Below Grade Unfin SQFT Source Assessor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 1

Exterior Features

Pool No Pool
Lot Features Cleared,No Thru Street
Water Source Well
Type of Parking Driveway
Land Use Code R
Foundation Details Slab
Water View Y/N Yes
Lot Size Acres 0.18
Water Body Type River
Lot Size Source Assessor
Waterfront Y/N Yes
Water Access Features Boat - Powered,Fishing Allowed,Personal Watercraft (PWC),Private Access,Swimming Allowed,Waterski/Wakeboard
Land Assessed Value 293000.00
Navigable Water Y/N Yes
Water Oriented Y/N Yes

Room Details

Bedroom 1 Main Flooring - HardWood
Bedroom 2 Main Flooring - HardWood
Dining Room Main Flooring - HardWood
Kitchen Main
Laundry Main
Living Room Main Flooring - HardWood
Sun/Florida Room Main Flooring - Vinyl

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Martinsburg, WV office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Unknown Elementary School
Middle School Leonardtown Middle School
High School Leonardtown High School

Price History

2/28/2026 Listed $500,000
4/22/2026 10% - $450,000

Property vs Zip Code Average in 20650

Price
AVG $1.09M
$450K
Taxes
AVG $46,320
$3,220
Year Built
AVG 1994
1950
Visits
AVG 424
355
Data Provided by Inside Real Estate®

Areas That We Cover

20798 Waterside Drive Leonardtown, MD is a Single Family Home for sale at $450000 with 1018 sqft and a lot size of 0.18 Acres Acre(s). 20798 Waterside Drive Leonardtown has 2 bedrooms, 1 baths and was built in 1950. The property's zip code is 20650 which is in Leonardtown, MD

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.