11

Leonardtown, MD Homes for Sale under $500,000

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  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /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
  • 21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    /31

    $479,000

    • 3 Beds
    • 2 Baths
    • 2,527 Sq Ft

    21925 Budds Creek Rd, Leonardtown, MD 20650

    This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family room with wood stove insert, large laundry room, and accessory area on the lower level. Also has a 2 Car Detached garage built in 2008. Roof of garage and house was re-shingled in 2020 with 50 year shingles. The HVAC was regularly serviced.

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (227) 230-5161

    21925 Budds Creek Rd, Leonardtown, MD 20650
  • Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $445,900 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650

    ***MOVE IN READY***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company.Unit 88 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison D2,

    Laura Bernth RE/MAX One

    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650
    Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650
    Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650
    /47

    $445,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company.Unit 92 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison

    Laura Bernth RE/MAX One

    Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650
    Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650
    Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650
    /57

    $469,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650

    ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Unit 97 Oakley D1New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious

    Laura Bernth RE/MAX One

    Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650
    Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650
    Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650
    /49

    $445,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. ***BACKS TO TREES***Unit 91 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the

    Laura Bernth RE/MAX One

    Lot 91-23694 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
    /50

    $445,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company.Unit 95 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior

    Laura Bernth RE/MAX One

    Lot 95-23718 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
    /49

    $479,900 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650

    ***Under Construction***Builder Incentive, Settle in 2025, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. ***November Delivery***Unit 103 Cumberland D1New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths |

    Laura Bernth RE/MAX One

    Lot 103-23701 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650
    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650
    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650
    /56

    $469,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650

    ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. November Delivery Unit 107 Oakley D1 *** Under Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car

    Laura Bernth RE/MAX One

    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
    Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
    Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
    /56

    $469,900 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650

    ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Unit 93 Oakley D1New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious

    Laura Bernth RE/MAX One

    Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
  • 25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    /5

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Real Estate & Homes in Leonardtown, MD under $500,000

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 36 days on the market compared to the national average of 52 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $540,000, down 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$592,500
Median Townhouse Sale Price
$445,900
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$197
Number of Homes for Sale
35
Last 12 months Home Sales
149
Months of Supply
2.80
Median List Price
$551,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
How to Buy a Home How to Finance a Home How to Sell a Home

In Leonardtown, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 11 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Leonardtown, MD and find the perfect fit for your homeownership goals.

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