7,080

Homes in ZIP Code 20650

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  • /3

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    18866 Russell Rd, Leonardtown, MD 20650

    ***Rare Waterfront Opportunity*** Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD, a truly exceptional waterfront property offering a private, peaceful setting on a premium lot with stunning views of the water. Currently a 3-bedroom, 1.5-bath home, this property presents the perfect opportunity to reimagine, renovate, or rebuild into your dream waterfront retreat. Surrounded by natural

    Agent Photo

    Shelly Hibbert

    KW Metro Center

    (227) 997-7054

    18866 Russell Rd, Leonardtown, MD 20650
  • /18

    $2,050 Per Month

    • 3 Beds
    • 1 Bath
    • 2,952 Sq Ft
    • House for Rent

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Charming Home !!!Welcome to in-town Leonardtown living—where everything you love is just a short walk away. ***Located just minutes from Leonardtown Wharf, award-winning restaurants, charming boutique shops, local wineries, and scenic parks, you’ll experience the best of what St. Mary’s County has to offer. Commuting is easy with quick access to major routes and PAX River Naval Air Station. This

    Robin Lower Residential Plus Real Estate Services

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • /83

    $655,000

    Sold Apr 24, 2026

    41497 Affirmed Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,934 Sq Ft
    • Built 2008

    Last Sold Summary

    • $166/SF
    • 2 Days On Market

    Current Estimated Value $653,153

    Last Listing Agent Heather Foster RE/MAX One

    41497 Affirmed Way, Leonardtown, MD 20650
    • /65

      Est $600,709

      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

  • /33

    $450,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    (227) 230-6008

    20798 Waterside Dr, Leonardtown, MD 20650
  • /32

    Starting at $2,250 Per Month

    • 2 - 3 Beds

    44980 Hamptons Blvd, Leonardtown, MD 20650

    The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE

    The Hamptons at Leonardtown

    (443) 342-9476

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • /86

    $633,000

    Sold Sep 19, 2025

    22272 Orchard Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,745 Sq Ft
    • Built 2004

    Last Sold Summary

    • $169/SF
    • 1 Day On Market

    Current Estimated Value $637,348

    Last Listing Agent Christina Reed RE/MAX One

    22272 Orchard Ct, Leonardtown, MD 20650
    • /75

      Est $466,471

      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

  • /42

    $650,000

    $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    40461 Old Breton Beach Rd, Leonardtown, MD 20650

    Experience waterfront living at its best with this beautifully maintained 2-bedroom, 2.5-bath home with a loft, perfectly positioned along the Potomac River just minutes from historic Leonardtown. Whether you’re looking for a full-time residence or a relaxing getaway, this property delivers the ideal blend of comfort, functionality, and breathtaking views. Designed for those who truly enjoy life

    Agent Photo

    Billy Rabbitt

    The Southside Group Real Estate

    (227) 239-0461

    40461 Old Breton Beach Rd, Leonardtown, MD 20650
  • /11

    $2,450 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,684 Sq Ft
    • House for Rent

    21113 Arbor Ct, Leonardtown, MD 20650

    Beautifully kept home nestled cozily off Rt. 5. Minutes away from local schools as well as downtown Leonardtown. Home was well kept and shows nicely. Lots of room at this property!Tenant pays METCOM, SMECO,Trash and lawncare are not included in the rental price

    Roland Mellies O'Brien Realty ERA Powered

    21113 Arbor Ct, Leonardtown, MD 20650
  • /2

    $1,100,000

    Sold May 15, 2026

    20045 Tower Hill Rd, Leonardtown, MD 20650

    • 5 Beds
    • 7 Baths
    • 7,376 Sq Ft
    • Built 1973

    Last Sold Summary

    • 24% Below List Price
    • $149/SF
    • 12 Days On Market

    Current Estimated Value $1,439,649

    Last Listing Agent Barbara Stellway KW Metro Center

    20045 Tower Hill Rd, Leonardtown, MD 20650
    • /41

      Est $576,477

      Not Listed For Sale

      23635 Abraham Dr, Leonardtown, MD 20650

      • 6 Beds
      • 4 Baths
      • 3,272 Sq Ft
      • Built 2004
      23635 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /27

    $329,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    22381 Cedar St, Leonardtown, MD 20650

    New pictures added! Back on the market due to buyer financing issues-no fault of the seller. Welcome to 23281 Cedar St in Leonardtown — where thoughtful updates meet easy coastal living in the sought-after St. Clements Shores community.This home was fully refreshed in 2021, offering today’s buyers the perfect blend of modern finishes and established reliability. Inside, you’ll find luxury

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    (227) 888-9336

    22381 Cedar St, Leonardtown, MD 20650
  • /10

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 4,112 Sq Ft
    • Townhouse for Rent

    44868 Blake Creek Rd, Leonardtown, MD 20650

    Small duplex apartment with Living Room, Den/Study, laundry room, eat-in kitchen, one bath and two bedrooms. Max two occupants. No pets allowed. Still waiting on a few repairs, but available for occupancy.Looking for good credit and background check. Off street parking. Total of four apartments in two building with two units per building. Freshly painted and new carpets.

    Jan Barnes CENTURY 21 New Millennium

    44868 Blake Creek Rd, Leonardtown, MD 20650
  • /21

    $731,084

    Sold Dec 04, 2025

    40744 Fawns Rest Way, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,313 Sq Ft
    • Built 2025

    Last Sold Summary

    • $221/SF
    • 0 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    40744 Fawns Rest Way, Leonardtown, MD 20650
    • /25

      Est $446,135

      Not Listed For Sale

      21684 Potomac View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft
      • Built 2002
      21684 Potomac View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 48 Days On Market

  • /52

    $540,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 3,014 Sq Ft

    21737 Pinehurst Ct, Leonardtown, MD 20650

    BRAND NEW ROOF! Built as a model for the neighborhood, this 3-bedroom, 2-bath Rambler will have you checking off your search boxes! Located on a quiet-cul-de-sac street in desirable Breton Bay, this lovely home includes more than 3,000 sq ft of living space and plenty of storage, too. Attractive landscaping greets you on your way to the welcoming front porch. A custom-glass front door leads into

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 242-0241

    21737 Pinehurst Ct, Leonardtown, MD 20650
  • /77

    $4,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 4,961 Sq Ft
    • House for Rent

    23687 Coventry Dr, Leonardtown, MD 20650

    Spacious rental home in the sought-after Leonard’s Grant community! This 6-bedroom, 4.5-bath home offers over 5,500 finished square feet with plenty of room to live, work, relax, and entertain. The main level features a gourmet kitchen with granite countertops, oversized island, double ovens, gas cooking, butler’s pantry, and breakfast room. The private main-level primary suite includes dual

    Robin Errington CENTURY 21 New Millennium

    23687 Coventry Dr, Leonardtown, MD 20650
  • /56

    $961,000

    Sold May 28, 2026

    40003 Tippit Rd, Leonardtown, MD 20650

    • 3 Beds
    • 3 Baths
    • 2,490 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $386/SF
    • 23 Days On Market

    Current Estimated Value $962,599

    Last Listing Agent Charlotte Long EXP Realty, LLC

    40003 Tippit Rd, Leonardtown, MD 20650
    • /6

      Est $321,644

      Not Listed For Sale

      44662 Blake Creek Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,344 Sq Ft
      • Built 1963
      44662 Blake Creek Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /48

    $449,900

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

    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650

    ***AVAILABLE NOW*** RECIEVE $12,500 in CLOSING HELP! (with use of Builder's Preferred Lender & Title) 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 one-car garage and

    Laura Hefley RE/MAX One

    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650
  • /74

    $3,200 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    22373 Enoch Rd, Leonardtown, MD 20650

    Gorgeous, Classy, Completely Remodeled Colonial on a Beautiful Premium Lot Backing to Trees in the Sought After Neighborhood of Breton Bay/Society Hill. A Welcoming Covered Front Porch is the perfect spot for enjoying the array of birds that live around the property. Open Floor Plan with Upgraded, Luxury Vinyl Plank (LVP) Flooring. Stylish Living Room with Wood Burning Fireplace, Charming Dining

    Jenny Norris EXP Realty, LLC

    22373 Enoch Rd, Leonardtown, MD 20650
  • /74

    $475,000

    Sold Jul 15, 2025

    43985 Main Way Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1973

    Last Sold Summary

    • $198/SF
    • 1 Day On Market

    Current Estimated Value $486,075

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, Leonardtown, MD 20650
    • /76

      Est $474,416

      Not Listed For Sale

      40827 Lake and Breton View Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 2,524 Sq Ft
      • Built 1969
      40827 Lake and Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 61 Days On Market

  • /34

    $449,900

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

    Lot 131 - 23703 Weeping Willow Way, Leonardtown, MD 20650

    ***PENDING***** Homesite # 131 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 one-car garage and an entry-level flex space that includes built-in cubbies

    Laura Hefley RE/MAX One

    Lot 131 - 23703 Weeping Willow Way, Leonardtown, MD 20650
  • /43

    $2,700 Per Month

    • 3 Beds
    • 3 Baths
    • 2,331 Sq Ft
    • House for Rent

    22397 Armstrong Dr, Leonardtown, MD 20650

    Just 7 minutes from the Leonardtown Square & Wharf, St. Mary's Hospital. 10 minutes from the beaches & trails of Newtowne Neck State Park. Armstrong Drive is located in the charming Breton Bay community. This delightful split-level home offers a perfect blend of comfort and convenience. Students are served by Benjamin Banneker Elementary School and Leonardtown Middle & High School. If you would

    Jonathan Powell Real Broker, LLC

    22397 Armstrong Dr, Leonardtown, MD 20650
  • /32

    $518,500

    Sold Dec 05, 2025

    22539 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft
    • Built 2005

    Last Sold Summary

    • $188/SF
    • 12 Days On Market

    Current Estimated Value $513,756

    Last Listing Agent Trish Brow O'Brien Realty ERA Powered

    22539 Landing Way, Leonardtown, MD 20650
    • /51

      Est $405,842

      Not Listed For Sale

      39880 Lady Baltimore Ave, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,348 Sq Ft
      • Built 1994
      39880 Lady Baltimore Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 48 Days On Market

  • /34

    $449,900

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

    Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650

    ****PENDING*** Homesite # 158 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 one-car garage and an entry-level flex space that includes built-in cubbies

    Laura Hefley RE/MAX One

    Lot 158 - 23646 Dragonfly Ln, Leonardtown, MD 20650
  • /54

    $2,490 Per Month

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • House for Rent

    23581 Belmar Dr, Leonardtown, MD 20650

    Recently Renovated Cabin on Over 2 Acres in Leonardtown! 3 Spacious Bedrooms; 2 Full Baths; Fully Renovated Kitchen with New Cabinets, Countertops, Appliances; New Flooring! See it Today! Walking Distance to Duke Elementary and Minutes to Leonardtown Middle School and Leonardtown High School! Close to Leonardtown Square, Shopping, Restaurants, Schools, and More! Application fee is $65 per adult

    Erika Yowell EXP Realty, LLC

    23581 Belmar Dr, Leonardtown, MD 20650
  • /79

    $639,000

    Sold Oct 30, 2025

    41474 Charismatic Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,647 Sq Ft
    • Built 2015

    Last Sold Summary

    • $175/SF
    • 57 Days On Market

    Current Estimated Value $645,659

    Last Listing Agent Laura Hefley RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
    • /17

      Est $692,643

      Not Listed For Sale

      21821 Cove Ln, Leonardtown, MD 20650

      • 2 Beds
      • 3 Baths
      • 2,748 Sq Ft
      • Built 1967
      21821 Cove Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • /19

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***Estimated Late October Delivery****To Be Built*** 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 Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • /90

    $575,000

    Sold Mar 05, 2026

    21060 Woodmere Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $187/SF
    • 18 Days On Market

    Current Estimated Value $571,306

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    21060 Woodmere Dr, Leonardtown, MD 20650
    • /46

      Est $483,215

      Not Listed For Sale

      40077 Big Chestnut Rd, Clements, MD 20624

      • 5 Beds
      • 3 Baths
      • 2,184 Sq Ft
      • Built 2008
      40077 Big Chestnut Rd, Clements, MD 20624

      Last Sold Summary

      • 32 Days On Market

  • /45

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650

    *****UNDER CONTRACT****** 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 Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full bath, perfect for a guest

    Laura Hefley RE/MAX One

    Lot 144 - 23635 Dragonfly Ln, Leonardtown, MD 20650
  • /50

    $459,900

    Sold Jun 17, 2026

    40810 Meadow Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • Built 1963

    Last Sold Summary

    • $336/SF
    • 14 Days On Market

    Current Estimated Value $452,661

    Last Listing Agent Cheryl Bare CENTURY 21 New Millennium

    40810 Meadow Dr, Leonardtown, MD 20650
    • /36

      Est $675,431

      Not Listed For Sale

      18914 Russell Rd, Valley Lee, MD 20692

      • 3 Beds
      • 2.5 Baths
      • 2,020 Sq Ft
      • Built 1999
      18914 Russell Rd, Valley Lee, MD 20692

      Last Sold Summary

      • 66 Days On Market

  • /48

    $610,000

    $30K PRICE DROP Under Contract
    • 5 Beds
    • 4 Baths
    • 3,724 Sq Ft

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    *Get up to $3,000 with use of preferred lender for closing cost assistance or use funds for a rate buy-down. This is your chance to own one of the LARGEST homes in the community, offering space, flexibility, and a lifestyle buyers are actively searching for. A compelling opportunity in CLARK'S REST. Welcome to 41377 Doctors Crossing Rd — a WELL-MAINTAINED home in the sought-after Clark’s Rest

    Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
  • /59

    $600,000

    Sold Oct 01, 2025

    43571 Bayberry Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 1993

    Last Sold Summary

    • $204/SF
    • 22 Days On Market

    Current Estimated Value $608,963

    Last Listing Agent Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 18

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