6,772

Leonardtown, MD Homes

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  • /34

    $439,900

    Under Contract
    • 4 Beds
    • 3 Baths
    • 1,624 Sq Ft

    40295 Busy Corner Rd, Leonardtown, MD 20650

    "NO HOA" This charming home offers 1,624 sq. ft. of living space, sits on a generous 3/4-acre lot, and features a new concrete stamped patio perfect for outdoor entertaining.. A true highlight of this property is the presence of Two Primary SuitesPrimary Suite 1, is an extremely large suite (24' x 19'—including the walk-in closet and attached bath) and features wood laminate floors, crown

    Agent Photo

    Kelly Niland

    Home Towne Real Estate

    (227) 997-7373

    40295 Busy Corner Rd, 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
  • /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
    • /46

      Est $945,858

      Not Listed For Sale

      22855 White Swan Way, Leonardtown, MD 20650

      • 5 Beds
      • 5.5 Baths
      • 6,762 Sq Ft
      • Built 2001
      22855 White Swan Way, Leonardtown, MD 20650

      Last Sold Summary

      • 30 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
  • /13

    $900

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • House for Rent

    41515 Singletree Dr, Leonardtown, MD 20650

    Large bedroom with walk in closet, can be furnished or unfinished and I can provide any other items needed for your comfort.Access to whole house with high speed internet House is walking distance to college of southern Maryland and St. Mary’s hospital in a very safe and quiet neighborhood.

    41515 Singletree Dr, 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
    • /36

      Est $481,297

      Not Listed For Sale

      22605 Calvert St, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,340 Sq Ft
      • Built 2018
      22605 Calvert St, Leonardtown, MD 20650

      Last Sold Summary

      • 62 Days On Market

  • /52

    $540,000

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

    21737 Pinehurst Ct, Leonardtown, MD 20650

    Seller is replacing roof ASAP..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

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 242-0241

    21737 Pinehurst Ct, 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. This home offers the rare combination of modern comfort and small-town charm, just steps from the waterfront, local restaurants, and year-round community events that make Leonardtown so special.*** Step outside and experience what sets this home apart: the ability to truly live local.

    Robin Lower Residential Plus Real Estate Services

    25365 Point Lookout Rd, 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
    • /72

      Est $680,155

      Not Listed For Sale

      23748 Coventry Dr, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 3,980 Sq Ft
      • Built 2013
      23748 Coventry Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • /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
  • /14

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,113 Sq Ft
    • Condo for Rent

    41820 Eastwick Ln Unit 3201, Leonardtown, MD 20650

    Beautiful condo for lease in the heart of Leonardtown...walk to everything downtown has to offer. Shopping, Restaurants, Ice Cream, Bars, and history! 2 Bedroom 2 bath and very well appointed with everything needed to live that condo life...This one won't last long so don't wait to come see!!

    Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    41820 Eastwick Ln Unit 3201, 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
    • /71

      Est $697,736

      Not Listed For Sale

      23287 Crestmar Ln, Leonardtown, MD 20650

      • 6 Beds
      • 4.5 Baths
      • 4,262 Sq Ft
      • Built 2019
      23287 Crestmar Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 26 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
  • /37

    $2,100 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,583 Sq Ft
    • House for Rent

    18937 McKays Cove Ln, Leonardtown, MD 20650

    Welcome to this charming water-access rambler! This inviting 3-bedroom, 1.5-bath home offers comfortable single-level living in a peaceful coastal setting.Inside, you’ll find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinet space, perfect for everyday living and entertaining. The functional open floor plan provides bright living areas, well-sized

    Erika Yowell EXP Realty, LLC

    18937 McKays Cove Ln, 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
    • /28

      Est $538,995

      Not Listed For Sale

      22301 Bayside Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,368 Sq Ft
      • Built 2012
      22301 Bayside Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 63 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
  • /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
    • /69

      Est $642,602

      Not Listed For Sale

      23567 Pine Bluff Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,736 Sq Ft
      • Built 2013
      23567 Pine Bluff Way, Leonardtown, MD 20650

      Last Sold Summary

      • 14 Days On Market

  • /64

    $635,000

    Under Contract
    • 5 Beds
    • 3 Baths
    • 3,030 Sq Ft

    41585 Austin Ct, Leonardtown, MD 20650

    Welcome to the completely unforgettable curb appeal of this home situated in the only culdesac of custom homes in the Estates at Singletree! Loved and beautifully maintained from the start by its current owners, they have personally curated, creative florals that surround this Southern Living traditional build, all the way to the perimeters of the property which provide abundant blueberries,

    Drema Ballengee-grunst EXP Realty, LLC

    41585 Austin Ct, Leonardtown, MD 20650
  • /36

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • House for Rent

    20503 Chestnut Ridge Dr, Leonardtown, MD 20650

    Located in the Chestnut Ridge Subdivision where peace and tranquility exist. 3 Bedroom 2 1/2 Bath, 2 Car Garage Cape Cod-style residence. Home has been Freshly painted and new carpet installed in all of the bedroom areas. Equipped with a new washer and dryer. Enjoy the country setting and sit on the Front porch or family gatherings on the rear large deck which is perfect for grilling. Any

    Jay Camp Coldwell Banker Premier

    20503 Chestnut Ridge 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
    • /30

      Est $774,580

      Not Listed For Sale

      40630 Breton Oaks Ln, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,736 Sq Ft
      • Built 2021
      40630 Breton Oaks Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 80 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
  • /54

    $2,695 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
    • /44

      Est $441,068

      Not Listed For Sale

      23380 Marview Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,306 Sq Ft
      • Built 2018
      23380 Marview Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 31 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
  • /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
    • /50

      Est $627,916

      Not Listed For Sale

      41442 Dauber Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,558 Sq Ft
      • Built 2013
      41442 Dauber Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 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
    • /58

      Est $694,170

      Not Listed For Sale

      23687 Coventry Dr, Leonardtown, MD 20650

      • 6 Beds
      • 4.5 Baths
      • 4,650 Sq Ft
      • Built 2012
      23687 Coventry Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 32 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
  • /61

    $440,000

    Sold Jun 16, 2025

    23445 Grovewood Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,379 Sq Ft
    • Built 2022

    Last Sold Summary

    • $185/SF
    • 46 Days On Market

    Current Estimated Value $448,201

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 18

Home Prices in Leonardtown, MD

Home Price Trends

Median Sale Price
$545,000
Median Single Family Sale Price
$586,500
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$340,000
Average Price Per Sq Ft
$194
Number of Homes for Sale
21
Last 12 months Home Sales
187
Months of Supply
1.30
Median List Price
$538,750
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
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