6,740

Leonardtown, MD Homes

Section Image Section Image
  • 21137 Marigold St, Leonardtown, MD 20650
    21137 Marigold St, Leonardtown, MD 20650
    21137 Marigold St, Leonardtown, MD 20650
    /42

    $555,000

    Sold Sep 26, 2025

    21137 Marigold St, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,382 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 6 Days On Market

    Current Estimated Value $559,365

    Last Listing Agent Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
    • 23075 Hollywood Rd, Leonardtown, MD 20650
      23075 Hollywood Rd, Leonardtown, MD 20650
      23075 Hollywood Rd, Leonardtown, MD 20650
      /82

      Est $574,165

      Not Listed For Sale

      23075 Hollywood Rd, Leonardtown, MD 20650

      • 5 Beds
      • 2.5 Baths
      • 3,238 Sq Ft
      • Built 1942
      23075 Hollywood Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Katy Galloway Century 21 Redwood Realty

  • 42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    42520 Riverwinds Dr, Leonardtown, MD 20650
    /10

    $1,999,999

    $500K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 2,744 Sq Ft

    42520 Riverwinds Dr, Leonardtown, MD 20650

    Seller is entertaining offers now. Looking for elbow room? Look no further—this property offers plenty of land! It borders the Potomac River and Poplar Hill Creek, featuring expansive farmland and forested areas. Ideal for outdoor enthusiasts and nature lovers, this unique property offers breathtaking sunsets. Correct acreage is 165 acres. Don't miss out on this unique opportunity.

    John Gatton CENTURY 21 New Millennium

    42520 Riverwinds Dr, Leonardtown, MD 20650
  • 40557 Breton Knolls Ct, Leonardtown, MD 20650
    40557 Breton Knolls Ct, Leonardtown, MD 20650
    /2

    $959,600

    Sold Aug 13, 2025

    40557 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $282/SF

    Current Estimated Value $868,569

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40557 Breton Knolls Ct, Leonardtown, MD 20650
    • 21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      /56

      Est $652,553

      Not Listed For Sale

      21147 Catnip Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft
      • Built 2002
      21147 Catnip Ct, Leonardtown, MD 20650

      Last Sold Summary

      Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

  • 40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    /77

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • 39944 Lady Baltimore Ave, Leonardtown, MD 20650
    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    /2

    $400,000

    Sold Jun 15, 2026

    39944 Lady Baltimore Ave, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 2,169 Sq Ft
    • Built 1997

    Last Sold Summary

    • 1% Above List Price
    • $184/SF
    • 7 Days On Market

    Current Estimated Value $403,646

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    • 41503 Affirmed Way, Leonardtown, MD 20650
      41503 Affirmed Way, Leonardtown, MD 20650
      41503 Affirmed Way, Leonardtown, MD 20650
      /80

      Est $703,036

      Not Listed For Sale

      41503 Affirmed Way, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 5,065 Sq Ft
      • Built 2008
      41503 Affirmed Way, Leonardtown, MD 20650

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent John Gatton CENTURY 21 New Millennium

  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /64

    $700,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • 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

    $439,900

    Sold Mar 31, 2026

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 74 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    • 41650 Marie Ct, Leonardtown, MD 20650
      41650 Marie Ct, Leonardtown, MD 20650
      41650 Marie Ct, Leonardtown, MD 20650
      /29

      Est $572,993

      Not Listed For Sale

      41650 Marie Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,808 Sq Ft
      • Built 2007
      41650 Marie Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Deanna Rothstein RE/MAX One

  • 40579 Port Place, Leonardtown, MD 20650
    40579 Port Place, Leonardtown, MD 20650
    40579 Port Place, Leonardtown, MD 20650
    /17

    $750,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    40579 Port Place, Leonardtown, MD 20650

    Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally

    Carol Kalmus-Choporis Century 21 Redwood Realty

    40579 Port Place, Leonardtown, MD 20650
  • 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

    $485,900

    Sold Apr 28, 2026

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

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1% Above List Price

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    • 40772 Magee Dr, Leonardtown, MD 20650
      40772 Magee Dr, Leonardtown, MD 20650
      40772 Magee Dr, Leonardtown, MD 20650
      /38

      Est $486,688

      Not Listed For Sale

      40772 Magee Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,258 Sq Ft
      • Built 1973
      40772 Magee Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Becky King Home Towne Real Estate

  • Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

    New Construction Open Thu 11AM - 4PM Pending
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #116 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 townhome offering 2,554 sq ft of beautifully finished living space. This interior unit features an oversized

    Laura Lee Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
  • lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    /41

    $458,550

    Sold Feb 26, 2026

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 78 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    • 39653 Potomac Ave, Leonardtown, MD 20650
      39653 Potomac Ave, Leonardtown, MD 20650
      39653 Potomac Ave, Leonardtown, MD 20650
      /60

      Est $798,000

      Not Listed For Sale

      39653 Potomac Ave, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,150 Sq Ft
      • Built 1988
      39653 Potomac Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Coley Reed Long & Foster Real Estate, Inc.

  • 24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    One of only two lots remaining! Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 to 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • 22164 Miller Ct, Leonardtown, MD 20650
    22164 Miller Ct, Leonardtown, MD 20650
    22164 Miller Ct, Leonardtown, MD 20650
    /88

    $1,052,000

    Sold Feb 25, 2026

    22164 Miller Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Above List Price
    • $390/SF
    • 7 Days On Market

    Current Estimated Value $1,037,772

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
    • 40139 Combs Creek Way, Leonardtown, MD 20650
      40139 Combs Creek Way, Leonardtown, MD 20650
      40139 Combs Creek Way, Leonardtown, MD 20650
      /68

      Est $1,212,833

      Not Listed For Sale

      40139 Combs Creek Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,944 Sq Ft
      • Built 1995
      40139 Combs Creek Way, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Andy Schweigman Douglas Realty, LLC

  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /75

    $645,000

    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside.The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • 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
    /47

    $489,900

    Sold Jun 30, 2026

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

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

    Last Sold Summary

    • $158/SF

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
    • 22321 Leonard St, Leonardtown, MD 20650
      22321 Leonard St, Leonardtown, MD 20650
      22321 Leonard St, Leonardtown, MD 20650
      /45

      Est $260,711

      Not Listed For Sale

      22321 Leonard St, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1930
      22321 Leonard St, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Lesa Clark Redfin Corp

  • 23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    /56

    $615,000

    • 5 Beds
    • 4 Baths
    • 4,346 Sq Ft

    23620 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so

    Tyler Mattingly Coldwell Banker Premier

    23620 Gunnell Dr, Leonardtown, MD 20650
  • 22820 Duke St, Leonardtown, MD 20650
    22820 Duke St, Leonardtown, MD 20650
    22820 Duke St, Leonardtown, MD 20650
    /9

    $340,000

    Sold Feb 20, 2026

    22820 Duke St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1947

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 0 Days On Market

    Current Estimated Value $334,270

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
    • 42990 Baywood Place, Leonardtown, MD 20650
      42990 Baywood Place, Leonardtown, MD 20650
      42990 Baywood Place, Leonardtown, MD 20650
      /68

      Est $694,828

      Not Listed For Sale

      42990 Baywood Place, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,724 Sq Ft
      • Built 2009
      42990 Baywood Place, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Farrah Fuchs Redfin Corp

  • 43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, Leonardtown, MD 20650
  • 20755 Deer Wood Park Dr, Leonardtown, MD 20650
    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    /27

    $515,000

    Sold Aug 15, 2025

    20755 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,538 Sq Ft
    • Built 1996

    Last Sold Summary

    • $203/SF
    • 10 Days On Market

    Current Estimated Value $546,398

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    • 24606 Pin Cushion Rd, Leonardtown, MD 20650
      24606 Pin Cushion Rd, Leonardtown, MD 20650
      24606 Pin Cushion Rd, Leonardtown, MD 20650
      /79

      Est $652,477

      Not Listed For Sale

      24606 Pin Cushion Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,466 Sq Ft
      • Built 1987
      24606 Pin Cushion Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Kimberly Scott RE/MAX Realty Group

  • Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
    /11

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650

    **TO BE BUILT**** Homesite 141 - Oakley D1 End Unit ***October Delivery**** ***Choose your color scheme from of our available options** Photos shown are representative and intended to illustrate a similar finished townhouse. 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

    Laura Lee Hefley RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
  • 22216 Hanover Dr, Leonardtown, MD 20650
    22216 Hanover Dr, Leonardtown, MD 20650
    22216 Hanover Dr, Leonardtown, MD 20650
    /75

    $640,000

    Sold Dec 01, 2025

    22216 Hanover Dr, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 4,206 Sq Ft
    • Built 2005

    Last Sold Summary

    • $152/SF
    • 1 Day On Market

    Current Estimated Value $646,383

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
    • 40539 Port Place, Leonardtown, MD 20650
      40539 Port Place, Leonardtown, MD 20650
      40539 Port Place, Leonardtown, MD 20650
      /92

      Est $1,137,328

      Not Listed For Sale

      40539 Port Place, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 3,371 Sq Ft
      • Built 1986
      40539 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium

  • 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

    New Construction 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 Lee Hefley RE/MAX One

    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
  • 23581 Gallent Fox Way, Leonardtown, MD 20650
    23581 Gallent Fox Way, Leonardtown, MD 20650
    23581 Gallent Fox Way, Leonardtown, MD 20650
    /53

    $645,900

    Sold Feb 26, 2026

    23581 Gallent Fox Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft
    • Built 2009

    Last Sold Summary

    • $173/SF
    • 42 Days On Market

    Current Estimated Value $647,141

    Last Listing Agent Laura Lee Hefley RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
    • 23558 Belmar Dr, Leonardtown, MD 20650
      23558 Belmar Dr, Leonardtown, MD 20650
      23558 Belmar Dr, Leonardtown, MD 20650
      /88

      Est $690,323

      Not Listed For Sale

      23558 Belmar Dr, Leonardtown, MD 20650

      • 6 Beds
      • 3.5 Baths
      • 4,267 Sq Ft
      • Built 2008
      23558 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      Last Listing Agent Heather Foster RE/MAX One

  • 20697 Chingville Rd, Leonardtown, MD 20650
    20697 Chingville Rd, Leonardtown, MD 20650
    20697 Chingville Rd, Leonardtown, MD 20650
    /87

    $475,203

    Sold Mar 02, 2026

    20697 Chingville Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $478,611

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
    • 21084 Rosebay St, Leonardtown, MD 20650
      21084 Rosebay St, Leonardtown, MD 20650
      21084 Rosebay St, Leonardtown, MD 20650
      /31

      Est $595,777

      Not Listed For Sale

      21084 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,505 Sq Ft
      • Built 2003
      21084 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Josh Yowell EXP Realty, LLC

  • 22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    /45

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    22010 Society Hill Rd, Leonardtown, MD 20650

    Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area

    Fran Slade Compass

    22010 Society Hill Rd, Leonardtown, MD 20650
  • 21335 Fairwood Ct, Leonardtown, MD 20650
    21335 Fairwood Ct, Leonardtown, MD 20650
    21335 Fairwood Ct, Leonardtown, MD 20650
    /39

    $720,000

    Sold May 11, 2026

    21335 Fairwood Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,533 Sq Ft
    • Built 2011

    Last Sold Summary

    • 1% Above List Price
    • $159/SF
    • 3 Days On Market

    Current Estimated Value $715,769

    Last Listing Agent Deanna Rothstein RE/MAX One

    21335 Fairwood Ct, Leonardtown, MD 20650

Showing Results 81 - 120, Page 3 of 18

Maryland St Marys County

Real Estate & Homes

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

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