7,049

Homes in ZIP Code 20650

Section Image
  • Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $449,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***READY-NOW Builder Incentive, 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. Unit 105 Madison D2: Photos Coming Soon 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 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
  • 41577 Church St, Leonardtown, MD 20650
    41577 Church St, Leonardtown, MD 20650
    41577 Church St, Leonardtown, MD 20650
    /25

    $2,800 per month

    • 3 Beds
    • 2.5 Baths
    • 909 Sq Ft
    • House for Rent

    41577 Church St, Leonardtown, MD 20650

    Brand New Family Comfort Steps from the Waterfront! Give your family the "elevated" lifestyle they deserve in this thoughtfully crafted new home. Located near the heart of Leonardtown’s year-round community events and waterfront, this residence offers the perfect blend of safety and style. Guests will love the flexible bedroom layouts, while parents will appreciate the attached garage and

    Michelle Camaioni RE/MAX One

    41577 Church St, Leonardtown, MD 20650
  • 23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    /61

    $440,000 Sold Jun 16, 2025

    23445 Grovewood Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,379 Sq Ft
    • Built 2022

    Last Sold Summary

    • $185/SF
    • 46 Days On Market

    Current Estimated Value $448,794

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
    • 22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      22301 Bayside Rd, Leonardtown, MD 20650
      /28

      Est $540,697 Not Listed For Sale

      22301 Bayside Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft
      • Built 2012
      22301 Bayside Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 14% Above List Price
      • $201/SF
      • 63 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Chad Istvan EXP Realty, LLC

  • 21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    21060 Woodmere Dr, Leonardtown, MD 20650
    /90

    $565,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft

    21060 Woodmere Dr, Leonardtown, MD 20650

    Nestled on a beautifully maintained 1 acre lot, this 5 bedroom, 3.5 bathroom home is conveniently located in Leonardtown's Wilderness Run community. A welcoming foyer leads to a formal dining room and a charming country style kitchen which opens to a spacious family room. The kitchen features space for a table, a large pantry, stainless steel appliances, granite countertops, and direct access to

    Sharon Cox CENTURY 21 New Millennium

    21060 Woodmere Dr, Leonardtown, MD 20650
  • 41573 Church St, Leonardtown, MD 20650
    41573 Church St, Leonardtown, MD 20650
    41573 Church St, Leonardtown, MD 20650
    /27

    $2,800 per month

    • 3 Beds
    • 2.5 Baths
    • 909 Sq Ft
    • House for Rent

    41573 Church St, Leonardtown, MD 20650

    Effortless Elegance & Walkability in the Heart of Town! Trade the maintenance of a large estate for the refined ease of this never-lived-in luxury rental. Designed for those with a taste for the finer things, this home features sleek cabinetry, designer fixtures, and a spa-inspired bath. The dedicated garage provides "lock-and-leave" security for travelers, while the doorstep access to

    Michelle Camaioni RE/MAX One

    41573 Church St, Leonardtown, MD 20650
  • 23155 Greenstone Dr, 3, Leonardtown, MD 20650
    23155 Greenstone Dr, 3, Leonardtown, MD 20650
    23155 Greenstone Dr, 3, Leonardtown, MD 20650
    /96

    $1,300,000 Sold Nov 13, 2025

    23155 Greenstone Dr, 3, Leonardtown, MD 20650

    • 6 Beds
    • 3.5 Baths
    • 5,888 Sq Ft
    • Built 2020

    Last Sold Summary

    • $221/SF
    • 63 Days On Market

    Current Estimated Value $1,248,655

    Last Listing Agent Jimmy Hayden RE/MAX One

    23155 Greenstone Dr, 3, Leonardtown, MD 20650
    • 23567 Pine Bluff Way, Leonardtown, MD 20650
      23567 Pine Bluff Way, Leonardtown, MD 20650
      23567 Pine Bluff Way, Leonardtown, MD 20650
      /69

      Est $652,868 Not Listed For Sale

      23567 Pine Bluff Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,736 Sq Ft
      • Built 2013
      23567 Pine Bluff Way, Leonardtown, MD 20650

      Last Sold Summary

      • 7% Above List Price
      • $163/SF
      • 14 Days On Market

      Last Sold Price $610,000

      Last Listing Agent Kimberly Scott Remax 100

  • Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
    /30

    $479,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650

    Homesite 102 Oakley D1*** Late March Delivery***Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. New 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 Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of

    Laura Bernth RE/MAX One

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
  • 43840 Tarrywyle Way, Leonardtown, MD 20650
    43840 Tarrywyle Way, Leonardtown, MD 20650
    43840 Tarrywyle Way, Leonardtown, MD 20650
    /42

    $5,000 per month

    • 6 Beds
    • 5 Baths
    • 5,278 Sq Ft
    • House for Rent

    43840 Tarrywyle Way, Leonardtown, MD 20650

    Tatiana Bell Quasar Property Management And Real Estate LLC

    43840 Tarrywyle Way, Leonardtown, MD 20650
  • 43012 Bluejay Ln, Leonardtown, MD 20650
    43012 Bluejay Ln, Leonardtown, MD 20650
    43012 Bluejay Ln, Leonardtown, MD 20650
    /9

    $740,500 Sold Mar 27, 2025

    43012 Bluejay Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,440 Sq Ft
    • Built 2021

    Last Sold Summary

    • $215/SF
    • 0 Days On Market

    Current Estimated Value $742,326

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    43012 Bluejay Ln, Leonardtown, MD 20650
    • 40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      40630 Breton Oaks Ln, Leonardtown, MD 20650
      /30

      Est $791,386 Not Listed For Sale

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft
      • Built 2021
      40630 Breton Oaks Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Above List Price
      • $201/SF
      • 80 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Helen Wernecke BHHS PenFed (actual)

  • Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    /40

    $479,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT********* 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 Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and

    Laura Bernth RE/MAX One

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
  • 41910 Nazareth Ct, Leonardtown, MD 20650
    41910 Nazareth Ct, Leonardtown, MD 20650
    /2

    $3,200 per month

    • 5 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • House for Rent

    41910 Nazareth Ct, Leonardtown, MD 20650

    5 bedroom, 3.5 bath home for rent in Leonardtown, MD. Close to shops, schools, parks and more. Property has main floor kitchen with large pantry space, beautiful new countertops, island style with optional dining area or formal dining room. Living/family room off of kitchen. The basement can double as an in-law suite with its own kitchen, bathroom, bedroom and living space. 2 car garage with

    Courtney Phipps Hooper & Associates

    41910 Nazareth Ct, Leonardtown, MD 20650
  • 42500 Saint Margarets Dr, Leonardtown, MD 20650
    42500 Saint Margarets Dr, Leonardtown, MD 20650
    42500 Saint Margarets Dr, Leonardtown, MD 20650
    /12

    $135,000 Sold May 09, 2025

    42500 Saint Margarets Dr, Leonardtown, MD 20650

    • Land
    • 4.8 Acres
    • $28,125 per Acre

    Last Sold Summary

    • 76 Days On Market

    Current Estimated Value $135,064

    Last Listing Agent Kalee Kelly Infinitas Realty Group

    42500 Saint Margarets Dr, Leonardtown, MD 20650
    • 23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      23380 Marview Ct, Leonardtown, MD 20650
      /44

      Est $454,143 Not Listed For Sale

      23380 Marview Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft
      • Built 2018
      23380 Marview Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 8% Above List Price
      • $183/SF
      • 31 Days On Market

      Last Sold Price $422,000

      Last Listing Agent Diana Washabaugh Century 21 New Millennium

  • Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
    /46

    $489,900 Pending

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

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650

    ***UNDER CONTRACT********* Lot 117 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 Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural

    Laura Bernth RE/MAX One

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
  • 21620 Coves End Ct, Leonardtown, MD 20650
    21620 Coves End Ct, Leonardtown, MD 20650
    21620 Coves End Ct, Leonardtown, MD 20650
    /67

    $691,000 Sold May 09, 2025

    21620 Coves End Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,541 Sq Ft
    • Built 2001

    Last Sold Summary

    • $195/SF
    • 33 Days On Market

    Current Estimated Value $703,431

    Last Listing Agent Hannah Cole Real Broker, LLC

    21620 Coves End Ct, Leonardtown, MD 20650
    • 40840 Greenwood Ln, Leonardtown, MD 20650
      40840 Greenwood Ln, Leonardtown, MD 20650
      40840 Greenwood Ln, Leonardtown, MD 20650
      /70

      Est $786,524 Not Listed For Sale

      40840 Greenwood Ln, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,320 Sq Ft
      • Built 2012
      40840 Greenwood Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5% Above List Price
      • $226/SF
      • 40 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

  • 23593 Mitchell Dr, Leonardtown, MD 20650
    23593 Mitchell Dr, Leonardtown, MD 20650
    23593 Mitchell Dr, Leonardtown, MD 20650
    /76

    $580,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    23593 Mitchell Dr, Leonardtown, MD 20650

    Welcome to your new home! This impressive 5-bedroom, 3.5-bathroom residence is a masterpiece of design, offering a spacious and well-thought-out layout. Nestled in a prime location with access to top-rated schools, this property caters to both practicality and beauty. Both HVAC systems have been replaced, roof has recently been replaced and a new BEAUTIFUL patio!!Key Features: **5 Bedrooms**:

    Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650
  • 41535 Singletree Dr, Leonardtown, MD 20650
    41535 Singletree Dr, Leonardtown, MD 20650
    41535 Singletree Dr, Leonardtown, MD 20650
    /54

    $510,000 Sold Dec 22, 2025

    41535 Singletree Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft
    • Built 2002

    Last Sold Summary

    • $225/SF
    • 44 Days On Market

    Current Estimated Value $533,020

    Last Listing Agent Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
    • 41408 W Citation St, Leonardtown, MD 20650
      41408 W Citation St, Leonardtown, MD 20650
      41408 W Citation St, Leonardtown, MD 20650
      /87

      Est $744,617 Not Listed For Sale

      41408 W Citation St, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft
      • Built 2013
      41408 W Citation St, Leonardtown, MD 20650

      Last Sold Summary

      • 1% Above List Price
      • $149/SF
      • 3 Days On Market

      Last Sold Price $740,000

      Last Listing Agent Heather Foster RE/MAX

  • 41438 Silver Charm Ct, Leonardtown, MD 20650
    41438 Silver Charm Ct, Leonardtown, MD 20650
    41438 Silver Charm Ct, Leonardtown, MD 20650
    /105

    $690,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft

    41438 Silver Charm Ct, Leonardtown, MD 20650

    Tucked away at the end of a quiet cul-de-sac in sought-after Leonard’s Grant, this stately brick-front home offers space, upgrades, and an exceptional setting on nearly half an acre.Step inside to a spacious, well-designed layout featuring a private first-floor office—ideal for working from home. The upgraded kitchen serves as the centerpiece of the home. There is ample cabinetry, a double

    Heather Foster RE/MAX One

    41438 Silver Charm Ct, Leonardtown, MD 20650
  • Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    /48

    $447,400 Sold Oct 09, 2025

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft
    • Built 2025

    Last Sold Summary

    • $175/SF
    • 58 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    • 22765 Duke St, Leonardtown, MD 20650
      22765 Duke St, Leonardtown, MD 20650
      22765 Duke St, Leonardtown, MD 20650
      /10

      Est $277,912 Not Listed For Sale

      22765 Duke St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft
      • Built 1949
      22765 Duke St, Leonardtown, MD 20650

      Last Sold Summary

      • 7% Above List Price
      • $302/SF
      • 6 Days On Market

      Last Sold Price $259,950

      Last Listing Agent Ronald Watson Flag Real Estate Inc.

  • Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
    /38

    $487,400 Pending

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

    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650

    ***UNDER CONTRACT*** 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 Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and the

    Laura Bernth RE/MAX One

    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
  • 42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    /71

    $599,900 Sold Jun 25, 2025

    42261 Bird Haven Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,233 Sq Ft
    • Built 2002

    Last Sold Summary

    • $186/SF
    • 18 Days On Market

    Current Estimated Value $599,756

    Last Listing Agent Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
    • 20102 Whippoorwill Ln, Leonardtown, MD 20650
      20102 Whippoorwill Ln, Leonardtown, MD 20650
      20102 Whippoorwill Ln, Leonardtown, MD 20650
      /76

      Est $719,164 Not Listed For Sale

      20102 Whippoorwill Ln, Leonardtown, MD 20650

      • 4 Beds
      • 4.5 Baths
      • 3,785 Sq Ft
      • Built 2002
      20102 Whippoorwill Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 11% Above List Price
      • $171/SF
      • 5 Days On Market

      Last Sold Price $648,000

      Last Listing Agent Robin Errington Century 21 New Millennium

  • 20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    /29

    $599,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
  • 28590 Point Lookout Rd, Loveville, MD 20656
    28590 Point Lookout Rd, Loveville, MD 20656
    /2

    $385,000 Sold Jun 12, 2025

    28590 Point Lookout Rd, Loveville, MD 20656

    • 4 Beds
    • 1.5 Baths
    • 1,816 Sq Ft
    • Built 1963

    Last Sold Summary

    • $212/SF
    • 0 Days On Market

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    28590 Point Lookout Rd, Loveville, MD 20656
    • 28845 Point Lookout Rd, Leonardtown, MD 20650
      28845 Point Lookout Rd, Leonardtown, MD 20650
      28845 Point Lookout Rd, Leonardtown, MD 20650
      /20

      Est $383,552 Not Listed For Sale

      28845 Point Lookout Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft
      • Built 1969
      28845 Point Lookout Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 10% Above List Price
      • $139/SF
      • 12 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Beverly Moody Remax 100

  • 23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    /57

    $599,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    PRICE IMPROVEMENT! **Custom Floorplan** Front Load Garage with expanded guest parking on driveway, upgraded cabinets, Countertops, and custom Primary suite walk in frameless glass shower. Built on an oversized premium corner lot with extra large fenced backyard. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • 22190 Bull Rd, Leonardtown, MD 20650
    22190 Bull Rd, Leonardtown, MD 20650
    /2

    $400,000 Sold Aug 18, 2025

    22190 Bull Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 1987

    Last Sold Summary

    • $290/SF

    Current Estimated Value $398,581

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    22190 Bull Rd, Leonardtown, MD 20650
    • 19661 Hickory Hills Ln, Leonardtown, MD 20650
      19661 Hickory Hills Ln, Leonardtown, MD 20650
      19661 Hickory Hills Ln, Leonardtown, MD 20650
      /76

      Est $562,018 Not Listed For Sale

      19661 Hickory Hills Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,342 Sq Ft
      • Built 1987
      19661 Hickory Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 7% Above List Price
      • $224/SF
      • 8 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Katy Galloway Century 21 New Millennium

  • 41515 Risen Star Ln, Leonardtown, MD 20650
    41515 Risen Star Ln, Leonardtown, MD 20650
    41515 Risen Star Ln, Leonardtown, MD 20650
    /5

    $659,900 Pending

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

    41515 Risen Star Ln, Leonardtown, MD 20650

    Welcome to the perfect blend of elegance, comfort, and location—this gorgeous Leonard's Grant home truly has it all and shows like a model. Meticulously maintained and move-in ready, this home offers 5 full bedrooms and 3.5 baths with a thoughtfully designed floor plan with plenty of room at 3,824 sq ft of finished space. The gourmet kitchen features a wall oven, gas cooktop, gorgeous cabinetry,

    Cynthia Crispell CENTURY 21 New Millennium

    41515 Risen Star Ln, Leonardtown, MD 20650
  • 43658 Redmond Rd, Leonardtown, MD 20650
    43658 Redmond Rd, Leonardtown, MD 20650
    43658 Redmond Rd, Leonardtown, MD 20650
    /16

    $281,650 Sold Sep 30, 2025

    43658 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 1.5 Baths
    • 2,078 Sq Ft
    • Built 1959

    Last Sold Summary

    • $136/SF
    • 12 Days On Market

    Current Estimated Value $292,175

    Last Listing Agent Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
    • 18822 McKays Beach Rd, Leonardtown, MD 20650
      18822 McKays Beach Rd, Leonardtown, MD 20650
      18822 McKays Beach Rd, Leonardtown, MD 20650
      /79

      Est $648,223 Not Listed For Sale

      18822 McKays Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft
      • Built 1998
      18822 McKays Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 6% Below List Price
      • $352/SF
      • 9 Days On Market

      Last Sold Price $690,000

      Last Listing Agent Ron Leonard Leonard Realty, Inc.

  • 22615 Washington St, Leonardtown, MD 20650
    22615 Washington St, Leonardtown, MD 20650
    22615 Washington St, Leonardtown, MD 20650
    /4

    $599,950 Under Contract

    • 1,691 Sq Ft

    22615 Washington St, Leonardtown, MD 20650

    Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts &

    Caitlin Vallandingham Infinitas Realty Group

    22615 Washington St, Leonardtown, MD 20650
  • Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    /49

    $447,400 Sold Dec 11, 2025

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
    • 41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      /39

      Est $626,719 Not Listed For Sale

      41419 Whimsical Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,993 Sq Ft
      • Built 2010
      41419 Whimsical Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 14% Above List Price
      • $184/SF
      • 49 Days On Market

      Last Sold Price $549,900

      Last Listing Agent John Gatton Century 21 New Millennium

Showing Results 41 - 80, Page 2 of 18

Maryland St Marys County Leonardtown 20650

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group