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Leonardtown, MD 1-Story Homes for Sale

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  • /33

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect 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

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • /37

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft

    23849 Point Lookout Rd, Leonardtown, MD 20650

    Excellent one level living in Leonardtown just past the high school, NO HOA, and sits on 1.5 acres of land. Front door was replaced in 2018; the rest of the doors and windows were replaced in 2025. Newer shingles replaced in 2015, the hall bathroom updated in 2024. Kitchen features a center island, which leads to a large outdoor deck for grilling and entertaining. Washer and dryer is being " sold

    Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
  • /13

    $239,000

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some well-deserved TLC.This

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • /80

    $790,000

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft

    39825 Sweetpea Ln, Leonardtown, MD 20650

    Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 feet of water frontage, this 4-bedroom, 3.5-bath home offers peace, privacy, and panoramic views. Inside, you'll find 2,408 square feet of comfortable living space featuring a cozy fireplace, wood stove, and large windows that invite the beauty of the outdoors in. The expansive deck is perfect for entertaining

    Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • /15

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    41130 Cryer Ct, Leonardtown, MD 20650

    This property is back on the market. This is your gain. A rare opportunity on the shores of Breton Bay, presents a canvas for transformation. This expansive 1.05 acre waterfront boast 164 feet of private shoreline and delivers breathtaking sunset panoramas. This classic 1955 construction offers endless renovation potential. With 1468 square feet of main living space and a 1247 square

    Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, Leonardtown, MD 20650
  • /32

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    Are you dreaming of living on the water? This is your perfect opportunity! Well maintained rambler featuring waterfront, pier with boatlift, sunroom, 2-car attached garage, 1-car detached garage, 2-car carport. Gorgeous back yard, perfect for entertaining and spending those summer nights with friends and family. Get on your boat whenever the mood strikes you. This is the perfect home to just

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • /3

    $530,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home is a modestly sized one story design that is loaded with all the necessities. Beautiful white siding and stained timber accents are perfect material choices for the farmhouse style. Offering an open main level with one large space for living and dining. The family room has a high ceiling. Enjoy the cozy ambiance of this home

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • /4

    $70,000

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    ONLINE AUCTION: Bidding begins 10/07/2025 @ 10:00 AM. Bidding ends 10/09/2025 @ 12:25 PM. List Price is Suggested Opening Bid. Deposit: $15,000.Single Family Home located in the Belvidere Woodland area. Located on +/- 40,000 SF of land, this property is JUST MINUTES to the St. Mary's State Park. Easy access to major traffic artery St. Andrew's Church Rd.

    Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, Leonardtown, MD 20650

Home Trends in Leonardtown, MD

Housing Trends

Median Sale Price
$544,950
Median Single Family Sale Price
$589,950
Median Townhouse Sale Price
$437,500
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$199
Number of Homes for Sale
32
Last 12 months Home Sales
140
Months of Supply
2.70
Median List Price
$556,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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