7,080

Homes in ZIP Code 20650

Section Image
  • /3

    $175,000

    $50K PRICE DROP
    • Land
    • 7.58 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, 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 $934,282

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40557 Breton Knolls Ct, Leonardtown, MD 20650
    • /39

      Est $611,281

      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

      • 49 Days On Market

  • /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 Hefley RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, 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 $465,703

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
    • /76

      Est $652,811

      Not Listed For Sale

      41474 Affirmed Way, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,050 Sq Ft
      • Built 2010
      41474 Affirmed Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /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 Hefley RE/MAX One

    Lot 138 - 23671 Dragonfly Ln, Leonardtown, MD 20650
  • /43

    $710,000

    Sold Jul 24, 2025

    21549 Point Lookout Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $721,048

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
    • /4

      Est $646,875

      Not Listed For Sale

      41443 Whimsical Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,400 Sq Ft
      • Built 2010
      41443 Whimsical Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

  • /54

    $485,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,019 Sq Ft

    21807 Potomac View Dr, Leonardtown, MD 20650

    Welcome home to the sought after community of Breton Bay in Leonardtown, where thoughtful updates, flexible living space, and an unbeatable location come together beautifully. This property offers the rare opportunity to enjoy all that Breton Bay has to offer, while still benefiting from no HOA restrictions. For a minimal optional annual fee, residents can enjoy private beach access at two

    Diana Washabaugh CENTURY 21 New Millennium

    21807 Potomac View Dr, 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 Hefley RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
    • /10

      Est $663,751

      Not Listed For Sale

      23598 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,758 Sq Ft
      • Built 2010
      23598 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 16 Days On Market

  • /10

    $1,100,000

    Coming Soon
    • 5 Beds
    • 4.5 Baths
    • 5,410 Sq Ft

    22856 White Swan Way, Leonardtown, MD 20650

    This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled with natural light

    Barbara Stellway KW Metro Center

    22856 White Swan Way, Leonardtown, MD 20650
  • /18

    $11,500

    Sold Apr 20, 2026

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636

    • Land
    • 1.23 Acres
    • $9,350 per Acre

    Last Sold Summary

    • 77% Below List Price
    • 57 Days On Market

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
    • /74

      Est $628,364

      Not Listed For Sale

      23546 Belmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,548 Sq Ft
      • Built 2009
      23546 Belmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

  • /7

    $772,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    44798 Medleys Neck Rd, Leonardtown, MD 20650

    Other lots in the area, call us to discussTBB - Custom Home - Many other floor plans and locations - call to discuss

    Marie Jozwik RE/MAX Realty Group

    44798 Medleys Neck Rd, 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 Hefley RE/MAX One

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
    • /25

      Est $290,117

      Not Listed For Sale

      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 2008
      41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /89

    $599,900

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    40704 Chance Way, Leonardtown, MD 20650

    Beautiful 4 bedroom, 2 1/2 bathroom colonial located in Leonardtown. Just mins from downtown Leonardtown amenities, shopping, restaurants, schools and more. This home has hardwood floors throughout. Spacious formal living and dining rooms. Kitchen with lots of cabinets and island with seating. Breakfast area and sliding doors that open to the back yard and patio. Family room w/gas fireplace off

    Kelly Padgett Century 21 Redwood Realty

    40704 Chance Way, 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 Hefley RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
    • /56

      Est $654,257

      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

  • /33

    $428,799

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,910 Sq Ft

    41600 Miss Bessie Dr, Leonardtown, MD 20650

    Brick-front one-level rambler featuring 3 bedrooms, 2 full bathrooms, and over 1,900 finished square feet. A welcoming covered front porch leads to an open and spacious interior with hardwood flooring throughout the foyer, hallway, living room, and formal dining room. The living room features a gas fireplace, while the dining room offers cathedral ceilings and Palladian windows for abundant

    Mike Mason Long & Foster Real Estate, Inc.

    41600 Miss Bessie Dr, 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 $1,027,170

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
    • /80

      Est $696,846

      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

  • /2

    $670,000

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Photos coming soon

    Heather Foster RE/MAX One

    23591 Margrave Dr, 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 $335,513

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
    • /29

      Est $576,972

      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

  • /32

    $395,900

    $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot.This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been

    Natalya Ford RE/MAX One

    21983 Point Lookout Rd, 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 $543,005

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    • /38

      Est $491,624

      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

  • /16

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 130 - 23709 Weeping Willow Way, Leonardtown, MD 20650

    ***PENDING***** ***Late August Delivery*** Homesite 130 Madison D1: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that

    Laura Hefley RE/MAX One

    Lot 130 - 23709 Weeping Willow Way, 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 $643,261

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
    • /60

      Est $768,667

      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

  • /28

    $99,000

    • Land
    • 2.28 Acres
    • $43,421 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, 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 $644,187

    Last Listing Agent Laura Hefley RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
    • /68

      Est $1,209,577

      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

  • /72

    $605,000

    Under Contract
    • 5 Beds
    • 5 Baths
    • 2,756 Sq Ft

    43430 Browns Ln, Leonardtown, MD 20650

    This 5 BR, 3 full BA, 2 half BA home offers nearly 3,000 square feet of comfortable living, but what truly sets it apart is everything beyond the main house. Step outside to your own backyard oasis featuring an in-ground saltwater pool, gazebo, and expansive entertaining space—perfect for summer gatherings or quiet evenings under the stars.Need room to grow, work, or host? The 28x40 detached

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns Ln, Leonardtown, MD 20650
  • /82

    $574,000

    Sold Jul 24, 2025

    23075 Hollywood Rd, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,238 Sq Ft
    • Built 1942

    Last Sold Summary

    • $177/SF
    • 55 Days On Market

    Current Estimated Value $570,745

    Last Listing Agent Katy Galloway Century 21 Redwood Realty

    23075 Hollywood Rd, Leonardtown, MD 20650
    • /45

      Est $260,710

      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

  • /45

    $449,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths

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

Showing Results 81 - 120, Page 3 of 18

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