# 20798 WATERSIDE Drive, Leonardtown, MD 20650

> **TL;DR:** 2bd/1ba single family, $450,000 ($442/sqft), built 1950, 1,018 sqft.
> Waterfront. Est. $2,406/mo. Listed 232 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $450,000 |
| Price/sqft | $442 |
| Bedrooms | 2 |
| Bathrooms | 1 full |
| Square Feet | 1,018 |
| Year Built | 1950 |
| Lot Size | 7,893 sqft (0.18 acres) |
| Stories | 1 |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 232 |

## Why This Home Stands Out

- **Waterfront** - Waterfront location listed

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $2,275 |
| Estimated Insurance | $131 |
| **Total** | **$2,406** |

## Nearby Schools

- **Middle:** LEONARDTOWN
- **High:** LEONARDTOWN

## Key Amenities

- Waterfront

## Property Highlights

- Built in 1950
- 0.18 acre lot
- Waterfront

## Description

### Agent 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 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.

## Location

- **Address:** 20798 WATERSIDE Drive, Leonardtown, MD 20650
- **County:** SAINT MARYS
- **Neighborhood:** BRUBACHERS
- **Coordinates:** 38.23896, -76.68673
- **Google Maps:** https://www.google.com/maps?q=38.23896,-76.68673

## Listing Agent

- **Name:** Connie M. Fitzgerald · **License:** 589189
- **Brokerage:** RE/MAX One
- **Broker Phone:** (410) 535-6291
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/20798-Waterside-Dr_Leonardtown_MD_20650_M68793-11642?f=listhub&s=TRENDPA&m=MDSM2029666&c=propsimple)

## Photos

![20798 WATERSIDE Drive - Photo 1](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3073422867r.jpg)

![20798 WATERSIDE Drive - Photo 2](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1877985515r.jpg)

![20798 WATERSIDE Drive - Photo 3](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1317121053r.jpg)

![20798 WATERSIDE Drive - Photo 4](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3877320656r.jpg)

![20798 WATERSIDE Drive - Photo 5](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1120524298r.jpg)

![20798 WATERSIDE Drive - Photo 6](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1388510976r.jpg)

![20798 WATERSIDE Drive - Photo 7](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f792070749r.jpg)

![20798 WATERSIDE Drive - Photo 8](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1628425460r.jpg)

![20798 WATERSIDE Drive - Photo 9](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3087979555r.jpg)

![20798 WATERSIDE Drive - Photo 10](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f110176080r.jpg)

![20798 WATERSIDE Drive - Photo 11](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3940072648r.jpg)

![20798 WATERSIDE Drive - Photo 12](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1121822712r.jpg)

![20798 WATERSIDE Drive - Photo 13](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3200403560r.jpg)

![20798 WATERSIDE Drive - Photo 14](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f2505095763r.jpg)

![20798 WATERSIDE Drive - Photo 15](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f2445316909r.jpg)

![20798 WATERSIDE Drive - Photo 16](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f2407622006r.jpg)

![20798 WATERSIDE Drive - Photo 17](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1091572462r.jpg)

![20798 WATERSIDE Drive - Photo 18](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1984930150r.jpg)

![20798 WATERSIDE Drive - Photo 19](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3651174297r.jpg)

![20798 WATERSIDE Drive - Photo 20](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f787455582r.jpg)

![20798 WATERSIDE Drive - Photo 21](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f138302081r.jpg)

![20798 WATERSIDE Drive - Photo 22](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f6705104r.jpg)

![20798 WATERSIDE Drive - Photo 23](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1285399570r.jpg)

![20798 WATERSIDE Drive - Photo 24](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f2519837921r.jpg)

![20798 WATERSIDE Drive - Photo 25](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1870643287r.jpg)

![20798 WATERSIDE Drive - Photo 26](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f3383133995r.jpg)

![20798 WATERSIDE Drive - Photo 27](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f2399544921r.jpg)

![20798 WATERSIDE Drive - Photo 28](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f4209583495r.jpg)

![20798 WATERSIDE Drive - Photo 29](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1529553254r.jpg)

![20798 WATERSIDE Drive - Photo 30](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f600873979r.jpg)

![20798 WATERSIDE Drive - Photo 31](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f1419686321r.jpg)

![20798 WATERSIDE Drive - Photo 32](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f4285814814r.jpg)

![20798 WATERSIDE Drive - Photo 33](http://lh.rdcpix.com/0ced8e47f09a31fb0a2a10e8c67b6398l-f2324765787r.jpg)

---

**MLS#:** MDSM2029666 | **Updated:** 2026-10-29
**Source:** listhub

*Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/20798-waterside-drive-leonardtown-md-20650-d41441db28c0475699af2d8691b30cea)

---

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