For Sale
Single family home for sale at 20798 Waterside Dr, Leonardtown, MD 20650 | MLS# MDSM2029666 | Listing updated on 2026-09-23
Photo 1 of Single family home for sale at 20798 Waterside Dr, Leonardtown, MD 20650 | MLS# MDSM2029666 | Listing updated on 2026-09-23
Photo 2 of Single family home for sale at 20798 Waterside Dr, Leonardtown, MD 20650 | MLS# MDSM2029666 | Listing updated on 2026-09-23
Photo 3 of Single family home for sale at 20798 Waterside Dr, Leonardtown, MD 20650 | MLS# MDSM2029666 | Listing updated on 2026-09-23
Photo 4 of Single family home for sale at 20798 Waterside Dr, Leonardtown, MD 20650 | MLS# MDSM2029666 | Listing updated on 2026-09-23
29+
Beds Icon

Street View

$450,000

Monthly Est:$2,240

  • Beds Icon2 Beds
  • Beds Icon
    1 Bath
  • Beds Icon1,018sqft

20798 Waterside Dr, Leonardtown, MD 20650

$2,240/moEst:

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  • Single Family Residence

  • Built in 1950

  • $-- HOA

  • 7,893 sqft lot

  • $442/sq.ft

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 refur
bished in 2020 for added shoreline protection
✔ Private pier with an electric boat lift—perfect for boating adventures
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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: September 23, 2026 at 3:33 pm
  • Listing Provided by: Connie M. Fitzgerald (301) 672-1634 , Michael Fitzgerald, II (301) 672-0765 | RE/MAX One (410) 535-6291
  • Source: Bright MLS-NJ | MLS#: MDSM2029666 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Saint Marys Md County

  • City

    Leonardtown

  • Neighborhood

    --

  • Year Built

    1950

  • HOA Fees

    -

  • Finished Area

    1,018 sqft

  • Lot Size

    7,893 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDSM2029666

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    195

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 2

    Bathroom: 1

Interior

  • Cooling

    Wall Unit

  • Appliances

    Refrigerator, Stove, Washer, Dryer

  • Flooring

    Hardwood, Vinyl, Wood

  • Sewer

    Septic Exists

  • Heating

    Forced Air, Other

  • Interior Features

    Floor Plan Traditional, Entry Level Bedroom, Combination Kitchen/living

Construction

  • Year Built

    Year Built: 1950

  • Home type

    Single Family Residence

  • Architectural Style

    Bungalow

  • Construction Materials

    Stucco

  • Foundation Details

    Slab

  • Roof

    Asphalt

Utilities & Energy

  • Water Source

    Well

  • Utilities

    Cable Tv Available

Other Features

  • Subdivision Name

    Brubachers

  • Lot Features

    Cleared, No Thru Street

Price History

DateEventPrice

03/13/2026

Source: mls_logoBright MLS-NJ #MDSM2029666

Listed for Sale

$450,000 -10.00%

$442/sqft

03/13/2026

Source: mls_logoBright MLS-NJ #MDSM2029666

Price Increased

$500,000 +4.28%

$491/sqft

06/21/2024

Source: mls_logoBright MLS-NJ #MDSM2019518

Off Market

$479,500

$471/sqft

Nearby Homes

Based on information from Bright MLS through Nov 02, 2026, 02:00PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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