6,736

Leonardtown, MD Homes

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  • /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 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is 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
  • /23

    $285,000 Sold Mar 20, 2025

    22239 Point Lookout Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,669 Sq Ft
    • Built 1966

    Last Sold Summary

    • $171/SF
    • 3 Days On Market

    Current Estimated Value $320,186

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    22239 Point Lookout Rd, Leonardtown, MD 20650
    • /39

      Est $657,128 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,748 Sq Ft

      21136 Catnip Way, Leonardtown, MD 20650

      21136 Catnip Way, Leonardtown, MD 20650
  • /6

    $159,900

    • Land
    • 1.49 Acres
    • $107,315 per Acre

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Charming Cul-de-Sac Lot in Breton Oaks – No HOA!Discover the perfect place to build your dream home on this beautiful, private lot located in the peaceful cul-de-sac of Breton Oaks. This small, custom-built subdivision offers a tranquil setting, with all homes in the neighborhood uniquely designed by St. Maries Builders. You can choose to build with them or bring your own builder to bring

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /2

    $825,000 Sold Jul 31, 2025

    40738 Bobwhite Ln, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 4,648 Sq Ft
    • Built 2000

    Last Sold Summary

    • $177/SF
    • 14 Days On Market

    Current Estimated Value $822,684

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    40738 Bobwhite Ln, Leonardtown, MD 20650
    • /19

      Est $366,518 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,412 Sq Ft

      43950 Blake Creek Rd, Leonardtown, MD 20650

      43950 Blake Creek Rd, Leonardtown, MD 20650
  • /60

    $529,900 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,482 Sq Ft

    41895 Tomey Ct, Leonardtown, MD 20650

    Well-maintained home in desirable Academy Hills, situated on a level corner lot within walking distance to Downtown Leonardtown. This home features an open floor plan with generously sized rooms and abundant natural light from extra windows throughout. The family room offers a cozy gas fireplace and flows seamlessly into the breakfast room and kitchen with breakfast bar, plus a separate formal

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    41895 Tomey Ct, Leonardtown, MD 20650
  • /76

    $460,000 Sold Jun 12, 2025

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,524 Sq Ft
    • Built 1969

    Last Sold Summary

    • $182/SF
    • 61 Days On Market

    Current Estimated Value $470,294

    Last Listing Agent Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    • /59

      Est $441,479 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft

      40781 Center 40 Cir, Leonardtown, MD 20650

      40781 Center 40 Cir, Leonardtown, MD 20650
  • /41

    $479,900 Pending

    • 4 Beds
    • 3.5 Baths

    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650

    UNDER CONTRACT***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

    Laura Bernth RE/MAX One

    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650
  • /82

    $701,650 Sold Sep 11, 2025

    22064 Daffodil Ct, Leonardtown, MD 20650

    • 6 Beds
    • 4.5 Baths
    • 5,012 Sq Ft
    • Built 2022

    Last Sold Summary

    • $140/SF
    • 43 Days On Market

    Current Estimated Value $701,886

    Last Listing Agent Laura Bernth RE/MAX One

    22064 Daffodil Ct, Leonardtown, MD 20650
    • /60

      Est $568,153 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,288 Sq Ft

      42055 Starlight Dr, Leonardtown, MD 20650

      42055 Starlight Dr, Leonardtown, MD 20650
  • /10

    $205,000

    • Land
    • 5 Acres
    • $41,000 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
  • /55

    $464,900 Sold Oct 07, 2025

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650

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

    Last Sold Summary

    • $157/SF
    • 54 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    • /39

      Est $689,100 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 5,488 Sq Ft

      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      21885 Newtowne Neck Rd, Leonardtown, MD 20650
  • /57

    $510,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,291 Sq Ft

    21920 Newtowne Neck Rd, Leonardtown, MD 20650

    Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,291 sq. ft. of comfortable living space, 4 bedrooms, and 2.5 bathrooms, perfectly situated on a .55-acre lot in Leonardtown. Inside, you’ll find a bright and spacious layout designed for both everyday living and entertaining. The heart of the home features an eat-in kitchen with stainless steel appliances, a

    Katherine Dean RE/MAX One

    21920 Newtowne Neck Rd, Leonardtown, MD 20650
  • /31

    $480,000 Sold Nov 24, 2025

    40534 Miss Ettas Way, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 82 Days On Market

    Last Listing Agent Connie Fitzgerald RE/MAX One

    40534 Miss Ettas Way, Leonardtown, MD 20650
    • /57

      Est $446,765 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,821 Sq Ft

      22106 Society Hill Rd, Leonardtown, MD 20650

      22106 Society Hill Rd, Leonardtown, MD 20650
  • /61

    $640,000

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    43018 Bluejay Ln, Leonardtown, MD 20650

    Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite

    Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
  • /37

    $540,000 Sold Apr 30, 2025

    40222 Breton Beach Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • Built 1976

    Last Sold Summary

    • $417/SF
    • 207 Days On Market

    Current Estimated Value $539,669

    Last Listing Agent Jake Grier Baldus Real Estate, Inc.

    40222 Breton Beach Rd, Leonardtown, MD 20650
    • /53

      Est $645,735 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,564 Sq Ft

      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      20529 Deer Wood Park Dr, Leonardtown, MD 20650
  • /66

    $550,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,328 Sq Ft

    22338 White Oak Rd, Leonardtown, MD 20650

    COMING SOON! Beautiful 4 bedroom, 2 1/2 bathroom colonial on over half an acre lot in Breton Bay! This home has has everything you could want with formal living & dining rooms, kitchen w/upgraded counter tops and appliances. The kitchen has bar style seating, a breakfast nook with built in bench and a seating area perfect for morning coffee and enjoying views of the back yard and pool. The back

    Kelly Padgett CENTURY 21 New Millennium

    22338 White Oak Rd, Leonardtown, MD 20650
  • /113

    $638,000 Sold Aug 12, 2025

    23275 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 6,311 Sq Ft
    • Built 2005

    Last Sold Summary

    • $101/SF
    • 86 Days On Market

    Current Estimated Value $652,224

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
    • /31

      Est $429,886 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,055 Sq Ft

      40862 Spring House Ln, Leonardtown, MD 20650

      40862 Spring House Ln, Leonardtown, MD 20650
  • /6

    $5,000

    • Land
    • 0.14 Acre
    • $35,714 per Acre

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650

    Fully Available!Wonderful opportunity with a buyer that has vision. Nice lot to possibly build on. Call St Mary's county for details and confirm if suitable for your needs.

    Jan Kleponis O'Brien Realty ERA Powered

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
  • /27

    $375,000 Sold Mar 07, 2025

    22395 Gore St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1982

    Last Sold Summary

    • $258/SF
    • 53 Days On Market

    Current Estimated Value $374,070

    Last Listing Agent Billy Rabbitt The Southside Group Real Estate

    22395 Gore St, Leonardtown, MD 20650
    • /46

      Est $926,758 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,828 Sq Ft

      40472 Port Place, Leonardtown, MD 20650

      40472 Port Place, Leonardtown, MD 20650
  • /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
  • /60

    $625,000 Sold Nov 26, 2025

    43107 Gum Spring Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft
    • Built 1993

    Last Sold Summary

    • $228/SF
    • 11 Days On Market

    Last Listing Agent Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, Leonardtown, MD 20650
    • /22

      Est $431,808 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft

      42454 Wilderness Rd, Leonardtown, MD 20650

      42454 Wilderness Rd, Leonardtown, MD 20650
  • /2

    $80,000

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    44646 Medleys Neck Rd, Leonardtown, MD 20650

    Presenting an opportunity for creative redevelopment: a level lot equipped with a septic system and a driveway easement, along with a trailer that has microbiological growth. The property will require the removal of the existing trailer, with the option to proceed with new construction or secure a trailer replacement. Qualified buyers looking to customize and reimagine the site are encouraged to

    Ron Lord Home Towne Real Estate

    44646 Medleys Neck Rd, 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 Bernth RE/MAX One

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

      Est $416,775 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,692 Sq Ft

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650
  • /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
  • /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 $591,630

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    • /83

      Est $574,246 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,115 Sq Ft

      41936 Kentucky Ct, Leonardtown, MD 20650

      41936 Kentucky Ct, Leonardtown, MD 20650
  • /49

    $639,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,322 Sq Ft

    41492 Charismatic Way, Leonardtown, MD 20650

    Welcome home to 41492 Charismatic Way, the stunning Fenwick model by Quality Built Homes in the highly sought-after Leonard’s Grant community in Leonardtown! With 4 spacious bedrooms, 3.5 baths, and nearly 4,000 finished sq ft, this well-appointed home blends elevated design, thoughtful functionality, and timeless comfort in every detail. A welcoming foyer opens to formal living and dining rooms,

    Laura Bernth RE/MAX One

    41492 Charismatic Way, Leonardtown, MD 20650
  • /4

    $163,500 Sold Nov 20, 2025

    21983 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1960

    Last Sold Summary

    • $143/SF
    • 37 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, Leonardtown, MD 20650
    • /54

      Est $596,964 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,538 Sq Ft

      20370 Chingville Rd, Leonardtown, MD 20650

      20370 Chingville Rd, Leonardtown, MD 20650
  • /30

    $565,000

    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    41635 Ferber Ct, Leonardtown, MD 20650

    Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and laundry room. Main level consists of living room, dining room, family room

    Alvin Frazier Home Towne Real Estate

    41635 Ferber Ct, Leonardtown, MD 20650

Showing Results 161 - 200, Page 5 of 18

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