6,774

Leonardtown, MD Homes

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  • /57

    $653,000

    $3K PRICE INCREASE Under Contract
    • 5 Beds
    • 3.5 Baths
    • 4,340 Sq Ft

    42032 Starlight Dr, Leonardtown, MD 20650

    Welcome to 42032 Starlight Drive in Leonardtown, MD, a spacious and beautifully updated home offering comfort, flexibility, and thoughtful upgrades throughout. This beautiful property backs to woods, providing a peaceful and private setting to enjoy year-round. Inside, fresh new paint throughout, new carpet upstairs, and new vinyl plank flooring in the basement give the home a clean,

    Bill Oosterink CENTURY 21 New Millennium

    42032 Starlight Dr, Leonardtown, MD 20650
  • /39

    $469,900

    Sold Dec 02, 2025

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    • /48

      Est $596,424

      Not Listed For Sale

      23244 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,357 Sq Ft
      • Built 2004
      23244 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 24 Days On Market

  • /3

    $779,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,745 Sq Ft

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Welcome to Breton Oaks—one of Leonardtown’s most sought-after communities—where this beautifully designed to-be-built home by Mednick Construction offers the perfect blend of modern farmhouse style and peaceful, wooded surroundings. Tucked away on a private, wooded lot on a quiet cul-de-sac, this thoughtfully crafted residence delivers timeless curb appeal paired with today’s most desirable

    Charlotte Long EXP Realty, LLC

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /60

    $599,000

    Sold Sep 18, 2025

    23650 Rocky Ridge Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,914 Sq Ft
    • Built 1993

    Last Sold Summary

    • $153/SF
    • 20 Days On Market

    Current Estimated Value $602,913

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    • /86

      Est $423,316

      Not Listed For Sale

      40427 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 4.5 Baths
      • 2,676 Sq Ft
      • Built 1994
      40427 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

  • /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • /51

    $415,000

    Sold Jun 09, 2025

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,348 Sq Ft
    • Built 1994

    Last Sold Summary

    • $308/SF
    • 48 Days On Market

    Current Estimated Value $405,842

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    • /64

      Est $498,970

      Not Listed For Sale

      42705 Redgate Farm Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 2,243 Sq Ft
      • Built 1995
      42705 Redgate Farm Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 36 Days On Market

  • /2

    $659,000

    Coming Soon
    • 5 Beds
    • 2.5 Baths
    • 2,601 Sq Ft

    40751 Merlin Way, Leonardtown, MD 20650

    **Stunning 5-Bedroom Colonial on Over 3 Private Acres in Leonardtown** Welcome to 40751 Merlin Way, a beautifully maintained brick-front Colonial tucked away on a private, secluded road in sought-after Leonardtown, Maryland. Situated on over 3 acres, this impressive 5-bedroom, 2.5-bath home offers the perfect blend of privacy, comfort, space, and convenience — all just minutes from local schools,

    Timothy Plummer Keller Williams Preferred Properties

    40751 Merlin Way, Leonardtown, MD 20650
  • /82

    $610,000

    Sold Nov 21, 2025

    21745 Pinehurst Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,860 Sq Ft
    • Built 1991

    Last Sold Summary

    • $213/SF
    • 3 Days On Market

    Current Estimated Value $612,982

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21745 Pinehurst Ct, Leonardtown, MD 20650
    • /9

      Est $536,319

      Not Listed For Sale

      20995 Chestnut Ridge Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,149 Sq Ft
      • Built 1996
      20995 Chestnut Ridge Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /10

    $190,000

    • Land
    • 5 Acres
    • $38,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • /5

    $664,900

    Sold Mar 20, 2026

    41515 Risen Star Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,136 Sq Ft
    • Built 2015

    Last Sold Summary

    • 1% Above List Price
    • $161/SF
    • 0 Days On Market

    Current Estimated Value $662,615

    Last Listing Agent Cynthia Crispell Century 21 Redwood Realty

    41515 Risen Star Ln, Leonardtown, MD 20650
    • /43

      Est $440,359

      Not Listed For Sale

      22292 White Oak Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,716 Sq Ft
      • Built 1978
      22292 White Oak Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 24 Days On Market

  • /78

    $550,000

    Pending
    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft

    40855 Spring House Ln, Leonardtown, MD 20650

    Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven

    Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • /37

    $355,000

    Sold Oct 17, 2025

    23849 Point Lookout Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1980

    Last Sold Summary

    • $325/SF
    • 4 Days On Market

    Current Estimated Value $350,950

    Last Listing Agent Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
    • /81

      Est $706,054

      Not Listed For Sale

      43164 Gum Spring Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,000 Sq Ft
      • Built 1999
      43164 Gum Spring Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /7

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

    ***** Hurry in! Secure your new home now and personalize it with your choice of interior colors. December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level

    Laura Hefley RE/MAX One

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
  • /43

    $715,000

    Sold Feb 20, 2026

    41832 Foxwell Point Ln, Leonardtown, MD 20650

    • 3 Beds
    • 4 Baths
    • 3,683 Sq Ft
    • Built 1991

    Last Sold Summary

    • $194/SF
    • 80 Days On Market

    Current Estimated Value $774,222

    Last Listing Agent Connie Fitzgerald RE/MAX One

    41832 Foxwell Point Ln, Leonardtown, MD 20650
    • /56

      Est $710,394

      Not Listed For Sale

      40688 Clearfields Ct, Leonardtown, MD 20650

      • 4 Beds
      • 4.5 Baths
      • 3,524 Sq Ft
      • Built 2003
      40688 Clearfields Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /41

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650

    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 Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The

    Laura Hefley RE/MAX One

    Lot 128 - 23721 Weeping Willow Way, Leonardtown, MD 20650
  • /30

    $519,900

    Sold Feb 27, 2026

    20250 Hawks Way, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,557 Sq Ft
    • Built 2025

    Last Sold Summary

    • $334/SF
    • 11 Days On Market

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    20250 Hawks Way, Leonardtown, MD 20650
    • /68

      Est $1,028,176

      Not Listed For Sale

      40741 Merlin Way, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 6,226 Sq Ft
      • Built 2003
      40741 Merlin Way, Leonardtown, MD 20650

      Last Sold Summary

      • 42 Days On Market

  • /33

    $459,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft

    41923 Sara Ann Ct, Leonardtown, MD 20650

    Sellers have outgrown this great Leonardtown location without the hustle and bustle of being in down town. Also offered at less than typical Leonardtown homes where the median sold price is $547,500. This 3 bedroom home has been upgraded with new deck/screened porch in 2023, upstairs vinyl flooring, kitchen quartz and new appliances in 2025 & backsplash & new roof. Be in and settled in this one

    Jimmy Hayden RE/MAX One

    41923 Sara Ann Ct, Leonardtown, MD 20650
  • /26

    $460,000

    Sold Oct 29, 2025

    41900 Nazareth Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,528 Sq Ft
    • Built 1999

    Last Sold Summary

    • $182/SF
    • 76 Days On Market

    Current Estimated Value $473,925

    Last Listing Agent Marizel Brewington JPAR Real Estate Professionals

    41900 Nazareth Ct, Leonardtown, MD 20650
    • /51

      Est $479,205

      Not Listed For Sale

      22152 Breton Woods Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,652 Sq Ft
      • Built 1987
      22152 Breton Woods Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /67

    $799,900

    • Land
    • 3.56 Acres
    • $224,691 per Acre

    39645 Sweetpea Ln, Leonardtown, MD 20650

    UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless

    Sandi Denny CENTURY 21 New Millennium

    39645 Sweetpea Ln, Leonardtown, MD 20650
  • /73

    $520,000

    Sold Sep 19, 2025

    21158 Marigold St, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,649 Sq Ft
    • Built 2001

    Last Sold Summary

    • $196/SF
    • 6 Days On Market

    Current Estimated Value $521,770

    Last Listing Agent Jarred Green Real Broker, LLC

    21158 Marigold St, Leonardtown, MD 20650
    • /72

      Est $578,919

      Not Listed For Sale

      23564 Gunnell Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,520 Sq Ft
      • Built 2003
      23564 Gunnell Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /30

    $485,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,507 Sq Ft

    22394 White Oak Rd, Leonardtown, MD 20650

    Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-bedroom, 3-bath split foyer offers space and comfort, and is move-in ready! The main level showcases stunning hardwood floors and a bright, inviting layout perfect for everyday living. The fully finished walk-out lower level features a spacious family room with a cozy fireplace, creating the ideal space for

    Barbara Stellway KW Metro Center

    22394 White Oak Rd, Leonardtown, MD 20650
  • /41

    $439,900

    Sold Mar 16, 2026

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 85 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650
    • /23

      Est $295,312

      Not Listed For Sale

      20235 Big Oak Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,036 Sq Ft
      • Built 1934
      20235 Big Oak Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /43

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650

    ***Available Now*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - 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, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town

    Laura Hefley RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
  • /2

    $565,000

    Sold Dec 05, 2025

    23261 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,575 Sq Ft
    • Built 2005

    Last Sold Summary

    • $158/SF
    • 15 Days On Market

    Current Estimated Value $578,060

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    23261 Jenifer Ct, Leonardtown, MD 20650
    • /6

      Est $732,796

      Not Listed For Sale

      41985 White Point Beach Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 2,222 Sq Ft
      • Built 1944
      41985 White Point Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • /85

    $569,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,308 Sq Ft

    41536 Fairwood Ct, Leonardtown, MD 20650

    Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage includes

    Teresa Klopfer RE/MAX Realty Group

    41536 Fairwood Ct, Leonardtown, MD 20650
  • /33

    $570,000

    Sold Oct 15, 2025

    23348 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,540 Sq Ft
    • Built 2022

    Last Sold Summary

    • $161/SF
    • 129 Days On Market

    Current Estimated Value $601,050

    Last Listing Agent Christi Turman-Rojas Fairfax Realty Premier

    23348 Lindsay Dr, Leonardtown, MD 20650
    • /28

      Est $348,347

      Not Listed For Sale

      22340 Gore St, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,292 Sq Ft
      • Built 1964
      22340 Gore St, Leonardtown, MD 20650

      Last Sold Summary

      • 76 Days On Market

  • /15

    $489,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***Estimated Late November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of

    Laura Hefley RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

Showing Results 201 - 240, Page 6 of 18

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