Leonardtown, MD Homes

• 

  

  

  /28

  Est $345,712

  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

  Last Listing Agent Kimberly Bannister T&G Real Estate Advisors, Inc.
• 

  

  

  /45

  $619,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft

  42096 Wildflower Dr, Leonardtown, MD 20650

  Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is

  Laura Lee Hefley RE/MAX One

  42096 Wildflower Dr, 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 $602,337

  Last Listing Agent Christi Turman-Rojas Fairfax Realty Premier

  23348 Lindsay Dr, Leonardtown, MD 20650
• 

  

  

  /37

  Est $635,816

  Not Listed For Sale

  41625 Ferber Ct, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths
  • 4,524 Sq Ft
  • Built 2005

  41625 Ferber Ct, Leonardtown, MD 20650

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Jonnie Jamison J2 Real Estate
• 

  

  

  /13

  $399,000

  • Land
  • 10,890 Sq Ft
  • $1,596,000 per Acre

  Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650

  Build your dream home in one of Leonardtown's most desirable locations! Welcome to Parcel 323, Tract 2, a newly created homesite just moments from the heart of historic downtown Leonardtown. Perfectly positioned to take advantage of beautiful water views of Breton Bay, this exceptional parcel offers the opportunity to enjoy the best of small-town coastal living. Imagine strolling to Leonardtown's

  Charlotte Long EXP Realty, LLC

  Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650
• 

  

  /65

  $600,000

  Sold Jun 30, 2026

  43430 Browns Ln, Leonardtown, MD 20650

  • 5 Beds
  • 5 Baths
  • 2,756 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Below List Price
  • $218/SF
  • 18 Days On Market

  Current Estimated Value $600,416

  Last Listing Agent Juliet Brown Residential Plus Real Estate Services

  43430 Browns Ln, Leonardtown, MD 20650
• 

  

  /41

  Est $483,163

  Not Listed For Sale

  41997 Loker Ct, Leonardtown, MD 20650

  • 4 Beds
  • 2.5 Baths
  • 2,330 Sq Ft
  • Built 2006

  41997 Loker Ct, Leonardtown, MD 20650

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jimmy Hayden RE/MAX One
• 

  

  /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
• 

  

  /35

  $449,900

  Sold Apr 16, 2026

  Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths

  Last Sold Summary

  Last Listing Agent Laura Lee Hefley RE/MAX One

  Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650
• 

  

  /67

  Est $596,164

  Not Listed For Sale

  23626 Abraham Dr, Leonardtown, MD 20650

  • 5 Beds
  • 3.5 Baths
  • 3,916 Sq Ft
  • Built 2005

  23626 Abraham Dr, Leonardtown, MD 20650

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Dawn Wood O'Brien Realty ERA Powered
• 

  

  /10

  $299,000

  • Land
  • 5.8 Acres
  • $51,552 per Acre

  21365 Bogies Ln, Leonardtown, MD 20650

  Looking for land to build your dream home....well wait no more! This 5.8 acre parcel has been perc tested, recorded, surveyed and even has builder specs for a future home site and floor plans. You can also pick your own builder and get construction started on your new home. Property is currently registered and enrolled in an Agricultural program. Close to schools, shopping and area amenities.

  Kelly Padgett Century 21 Redwood Realty

  21365 Bogies Ln, Leonardtown, MD 20650
• 

  

  /86

  $595,000

  Sold Apr 14, 2026

  21749 Pinehurst Ct, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths
  • 3,410 Sq Ft
  • Built 1993

  Last Sold Summary

  • 4% Above List Price
  • $174/SF
  • 2 Days On Market

  Current Estimated Value $591,574

  Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

  21749 Pinehurst Ct, Leonardtown, MD 20650
• 

  

  /88

  Est $608,692

  Not Listed For Sale

  23689 Jm Gough Ct, Leonardtown, MD 20650

  • 5 Beds
  • 4 Baths
  • 3,828 Sq Ft
  • Built 2005

  23689 Jm Gough Ct, Leonardtown, MD 20650

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Bill Oosterink CENTURY 21 New Millennium
• 

  

  /36

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  23898 Speith Rd, Leonardtown, MD 20650

  **Seller offering $10,000 in Closing Help** Step into this ONE level, completely renovated home that was stripped down to the studs and everything was replaced from the roof to the floor, new well, and connected to public sewer in 2022. Expand without having to worry about where the septic or septic reserve area is. See and feel the craftsmanship that was put in with wood flooring, stainless

  Jimmy Hayden RE/MAX One

  23898 Speith Rd, Leonardtown, MD 20650
• 

  

  /45

  $449,900

  Sold Jun 25, 2026

  Lot 115 - 23708 Weeping Willow Way, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths

  Last Sold Summary

  Last Listing Agent Laura Lee Hefley RE/MAX One

  Lot 115 - 23708 Weeping Willow Way, Leonardtown, MD 20650
• 

  

  /65

  Est $607,147

  Not Listed For Sale

  42279 Bird Haven Dr, Leonardtown, MD 20650

  • 5 Beds
  • 3.5 Baths
  • 3,139 Sq Ft
  • Built 2002

  42279 Bird Haven Dr, Leonardtown, MD 20650

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Mike Jordan CENTURY 21 New Millennium
• 

  

  /139

  $15,000,000

  Open Sat 1PM - 3PM

  • 6 Beds
  • 4.5 Baths
  • 5,500 Sq Ft

  19700 Mulberry Fields Rd, Leonardtown, MD 20650

  LUXURY PROPERTY AUCTION: 13 August - 27 August.Accepting starting bids through 27 August.Listed for $20M.Earn an incentive by 13 August. OPEN HOUSES EVERY WEEKEND SATURDAY AND SUNDAY 1-3 PM. PLEASE COME AND TAKE A LOOK AT THIS MAGNIFICENT 500 ACRE ESTATE WHERE THE FOUNDING FATHER'S ONCE MINGLED! Mulberry Fields is one of those rare places where the land itself tells the story. The

  Kornelia Stuphan Long & Foster Real Estate, Inc.

  19700 Mulberry Fields Rd, Leonardtown, MD 20650
• 

  

  /82

  $675,000

  Sold Aug 14, 2025

  44074 Medleys Neck Rd, Leonardtown, MD 20650

  • 4 Beds
  • 3 Baths
  • 3,830 Sq Ft
  • Built 2006

  Last Sold Summary

  • $176/SF
  • 3 Days On Market

  Current Estimated Value $688,932

  Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

  44074 Medleys Neck Rd, Leonardtown, MD 20650
• 

  

  /43

  Est $581,220

  Not Listed For Sale

  21081 Rosebay St, Leonardtown, MD 20650

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft
  • Built 2002

  21081 Rosebay St, Leonardtown, MD 20650

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Melissa Rodriguez RE/MAX One
• 

  

  /87

  $924,999

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  41402 Philip Ln, Leonardtown, MD 20650

  Discover the charm of this lovely waterfront ranch-style home, located in the Mulberrys on Breton Bay neighborhood. With 2,550 sq. ft. of living space, this home features four spacious bedrooms and 2.5 bathrooms, ensuring comfort for all. Open concept living on the main floor includes spacious family/dining area, primary bedroom and updated kitchen with custom Woodburn soft close cabinetry, under

  Cynthia Ballard Century 21 Redwood Realty

  41402 Philip Ln, Leonardtown, MD 20650
• 

  /2

  $800,000

  Sold May 05, 2026

  40737 Bobwhite Ln, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths
  • 5,454 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 23 Days On Market

  Current Estimated Value $799,140

  Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  40737 Bobwhite Ln, Leonardtown, MD 20650
• 

  

  /82

  Est $590,417

  Not Listed For Sale

  22030 Cartwright Rd, Leonardtown, MD 20650

  • 5 Beds
  • 3.5 Baths
  • 2,475 Sq Ft
  • Built 2005

  22030 Cartwright Rd, Leonardtown, MD 20650

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Bill Oosterink CENTURY 21 New Millennium
• 

  

  /26

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,218 Sq Ft

  42163 Blacksmith Shop Rd, Leonardtown, MD 20650

  Welcome Home! This charming rambler offers approximately 1,200 square feet of comfortable one-level living situated on a level 0.60-acre lot. A covered front porch provides a welcoming entry, while inside, the home has a practical floor plan with new flooring throughout and new kitchen appliances. Outside, enjoy the deck for relaxing or entertaining. With no HOA, you’ll appreciate the added

  Wanda White CENTURY 21 New Millennium

  42163 Blacksmith Shop Rd, Leonardtown, MD 20650
• 

  

  /34

  $625,000

  Sold Sep 30, 2025

  23246 Lindsay Dr, Leonardtown, MD 20650

  • 5 Beds
  • 3.5 Baths
  • 3,876 Sq Ft
  • Built 2017

  Last Sold Summary

  • $161/SF
  • 55 Days On Market

  Current Estimated Value $649,703

  Last Listing Agent Wanda White CENTURY 21 New Millennium

  23246 Lindsay Dr, Leonardtown, MD 20650
• 

  

  /30

  Est $333,123

  Not Listed For Sale

  39790 Lady Baltimore Ave, Leonardtown, MD 20650

  • 4 Beds
  • 3 Baths
  • 1,344 Sq Ft
  • Built 1991

  39790 Lady Baltimore Ave, Leonardtown, MD 20650

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Chris Craddock EXP Realty, LLC
• 

  $614,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,785 Sq Ft

  The Fenwick Plan at Meadows at Town Run - Single Family Homes, Leonardtown, MD 20650

  Quality Built Homes Builder

  23731 Dragonfly Ln Unit 41509703, Leonardtown, MD 20650
• 

  

  /79

  $649,900

  Sold Jul 06, 2026

  23642 Hansel Ct, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths
  • 3,726 Sq Ft
  • Built 2010

  Last Sold Summary

  • $174/SF
  • 17 Days On Market

  Current Estimated Value $648,474

  Last Listing Agent Diane Fenwick RE/MAX One

  23642 Hansel Ct, Leonardtown, MD 20650
• 

  

  /42

  Est $663,756

  Not Listed For Sale

  20708 Waterside Dr, Leonardtown, MD 20650

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1925

  20708 Waterside Dr, Leonardtown, MD 20650

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jenny Norris EXP Realty, LLC
• 

  

  /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
• 

  

  /43

  $459,900

  Sold Dec 02, 2025

  Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650

  • 4 Beds
  • 3.5 Baths
  • 2,966 Sq Ft
  • Built 2025

  Last Sold Summary

  • $155/SF
  • 29 Days On Market

  Last Listing Agent Laura Lee Hefley RE/MAX One

  Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
• 

  

  /75

  Est $464,913

  Not Listed For Sale

  41925 Nazareth Ct, Leonardtown, MD 20650

  • 3 Beds
  • 3 Baths
  • 2,512 Sq Ft
  • Built 2005

  41925 Nazareth Ct, Leonardtown, MD 20650

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Dawn Bell RE/MAX One
• 

  

  /56

  $749,000

  $26K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,097 Sq Ft

  22393 Saint Clements Ave, Leonardtown, MD 20650

  Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the breathtaking water views, this light-filled home features an open-concept floor plan that seamlessly blends comfortable everyday living with exceptional entertaining space. Offering 4 bedrooms, 2 full baths, and 2 half baths, the home has been extensively

  Alyson Anderson Allfirst Realty, Inc.

  22393 Saint Clements Ave, Leonardtown, MD 20650
• 

  

  /43

  $449,900

  Sold Jul 31, 2026

  Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650

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

  Last Sold Summary

  • $176/SF
  • 99 Days On Market

  Last Listing Agent Laura Lee Hefley RE/MAX One

  Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
• 

  

  /18

  Est $402,195

  Not Listed For Sale

  40443 Breton View Dr, Leonardtown, MD 20650

  • 3 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Built 1994

  40443 Breton View Dr, Leonardtown, MD 20650

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Anne Davis CENTURY 21 New Millennium
• 

  

  /72

  $609,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,701 Sq Ft

  42102 Wildflower Dr, Leonardtown, MD 20650

  New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s suite

  Laura Lee Hefley RE/MAX One

  42102 Wildflower Dr, Leonardtown, MD 20650
• 

  $300,000

  Sold Oct 15, 2025

  22323 Saint Clements Ave, Leonardtown, MD 20650

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1955

  Last Sold Summary

  • $250/SF
  • 0 Days On Market

  Current Estimated Value $301,230

  Last Listing Agent Matthew Burgan Infinitas Realty Group

  22323 Saint Clements Ave, Leonardtown, MD 20650
• 

  

  /55

  Est $556,232

  Not Listed For Sale

  41935 Green Hills Ln, Leonardtown, MD 20650

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1998

  41935 Green Hills Ln, Leonardtown, MD 20650

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Mike Jordan CENTURY 21 New Millennium
• 

  

  /7

  $454,900

  New Construction $5K PRICE INCREASE

  • 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 Lee Hefley RE/MAX One

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

  

  /48

  $360,000

  Sold Sep 26, 2025

  40480 Parsons Mill Rd, Leonardtown, MD 20650

  • 3 Beds
  • 1 Bath
  • 1,884 Sq Ft
  • Built 1974

  Last Sold Summary

  • $191/SF
  • 35 Days On Market

  Current Estimated Value $374,261

  Last Listing Agent John Gatton CENTURY 21 New Millennium

  40480 Parsons Mill Rd, Leonardtown, MD 20650
• 

  

  /41

  Est $445,250

  Not Listed For Sale

  21717 Meadow Ct, Leonardtown, MD 20650

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft
  • Built 1981

  21717 Meadow Ct, Leonardtown, MD 20650

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

Showing Results 241 - 280, Page 7 of 18