6,717

Leonardtown, MD Homes

Section Image
  • /40

    $434,900 Sold Sep 30, 2025

    • 2,306 Sq Ft
    • $189/SF
    • 28 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2018

    23392 Marview Ct, Leonardtown, MD 20650

    Compton Model Townhome in Clark’s Rest- Offering over 1,900 square feet of living space, this spacious 3-bedroom, 3.5-bath home blends style, function, and comfort — all just minutes from historic downtown Leonardtown.Step inside to find a bright, open-concept floor plan with gleaming hardwood on the main level, and abundant natural light. The rear kitchen design is a true showstopper,

    Ana Galvan CENTURY 21 New Millennium

    23392 Marview Ct, Leonardtown, MD 20650
    • /65

      Est $849,279 Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 4,873 Sq Ft

      22265 Orchard Ct, Leonardtown, MD 20650

      22265 Orchard Ct, Leonardtown, MD 20650
  • /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
  • /74

    $660,000 Sold Sep 29, 2025

    • 3,194 Sq Ft
    • $207/SF
    • 12 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2010

    23647 Hansel Ct, Leonardtown, MD 20650

    GORGEOUS HOME ON A CUL DE SAC! HIGHLIGHTS: 2 NEW HVAC UNITS, RADON MITIGATION SYSTEM, IN GROUND SPRINKLERS, 2 TIER COMPOSITE DECK WITH PAVER PATIO, FENCE, ETC...This beautifully maintained QBH Newport model located in the sought-after Leonards Grant community is move in ready! Walk in to a welcoming entryway that opens to a few spacious rooms and a gourmet kitchen. The kitchen has

    Heather Foster RE/MAX One

    23647 Hansel Ct, Leonardtown, MD 20650
    • /45

      Est $382,968 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,308 Sq Ft

      19137 Lake Dr, Leonardtown, MD 20650

      19137 Lake Dr, Leonardtown, MD 20650
  • /66

    $550,000

    • 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
  • /42

    $555,000 Sold Sep 26, 2025

    • 2,382 Sq Ft
    • $233/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2003

    21137 Marigold St, Leonardtown, MD 20650

    Imagine this: a spacious, thoughtfully designed home where bright natural light fills oversized rooms while still offering the privacy you crave. Hardwood floors, crown molding, and 9-foot ceilings creating an inviting atmosphere, and a full walk-out basement plus a laundry room with built-in cabinetry add practical living space. The master suite features a soaking tub and separate shower, and

    Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
    • /50

      Est $291,723 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,008 Sq Ft

      22204 Nomoni St, Leonardtown, MD 20650

      22204 Nomoni St, 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
  • /48

    $360,000 Sold Sep 26, 2025

    • 1,884 Sq Ft
    • $191/SF
    • 35 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1974

    40480 Parsons Mill Rd, Leonardtown, MD 20650

    Experience country living at its finest in this expansive rambler, nestled amidst picturesque farmlands. This charming home offers three generously sized bedrooms and one well-appointed bathroom, epitomizing the timeless appeal of rural living. Rich hardwood floors flow seamlessly throughout the entire residence, adding warmth and character.Each bedroom is designed for comfort, offering

    John Gatton CENTURY 21 New Millennium

    40480 Parsons Mill Rd, Leonardtown, MD 20650
    • /23

      Est $332,568 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      23028 Hopton Ln, Leonardtown, MD 20650

      23028 Hopton Ln, Leonardtown, MD 20650
  • /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
  • /61

    $545,000 Sold Sep 26, 2025

    • 2,102 Sq Ft
    • $259/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2004

    23220 Brandon Ct, Leonardtown, MD 20650

    Welcome home to this beautifully maintained one-level brick front residence, offering a thoughtfully designed split-bedroom floorplan ideal for both comfort and privacy. With 3 bedrooms and 2 full baths, this home features a welcoming foyer entry that leads to a spacious formal dining area, perfect for gatherings and special occasions.The family room boasts vaulted ceilings and a cozy gas

    Jennifer Goddard CENTURY 21 New Millennium

    23220 Brandon Ct, Leonardtown, MD 20650
    • /76

      Est $674,015 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,992 Sq Ft

      41488 Pensive St, Leonardtown, MD 20650

      41488 Pensive St, 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

    $971,725 Sold Sep 24, 2025

    • 4,000 Sq Ft
    • $243/SF
    • 764 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2025

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    To Be Built - A Breton Knolls exclusive offering. Be the first to call this to-be-built custom-crafted home yours! Located in the heart of Leonardtown on oversized lots, this new 24-lot subdivision offers an elegantly crafted home by well-known local builder, Litz Custom Homes. The Jackson floor plan perfectly combines the essence of a Colonial Farmhouse with a modern twist to include over 3,000

    Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
    • /70

      Est $677,503 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft

      21380 Fairwood Ct, Leonardtown, MD 20650

      21380 Fairwood Ct, Leonardtown, MD 20650
  • /5

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • /78

    $709,000 Sold Sep 24, 2025

    • 3,970 Sq Ft
    • $179/SF
    • 24 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2011

    21385 Fairwood Ct, Leonardtown, MD 20650

    ENTERTAINERS DREAM! Expansive Living, 4-CAR GARAGE(S), & Heated Pool - Now PRICED TO SELL! Seize this incredible opportunity to own a meticulously maintained, stunning home with an exquisite outdoor entertaining space. This significant adjustment reflects the seller's response to market feedback and motivation to find the perfect buyer quickly, ensuring you can enjoy an unparalleled lifestyle and

    Dawn Bell RE/MAX One

    21385 Fairwood Ct, Leonardtown, MD 20650
    • /44

      Est $471,271 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,204 Sq Ft

      22480 Sparrow Ct, Leonardtown, MD 20650

      22480 Sparrow Ct, Leonardtown, MD 20650
  • /2

    $225,000

    • Land
    • 7.5 Acres
    • $30,000 per Acre

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen. The

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, Leonardtown, MD 20650
  • /86

    $633,000 Sold Sep 19, 2025

    • 3,745 Sq Ft
    • $169/SF
    • 1 Day On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2004

    22272 Orchard Ct, Leonardtown, MD 20650

    Welcome to Hanover Farms in Breton Bay, a sought-after private water-access community in Leonardtown offering a neighborhood pier and beach. This charming rambler with a full basement sits on nearly an acre at the end of a quiet cul-de-sac, featuring a flat, fenced lot for both privacy and function.Inside, the split floor plan provides the perfect balance of comfort and convenience, with the

    Christina Reed RE/MAX One

    22272 Orchard Ct, Leonardtown, MD 20650
    • /42

      Est $586,946 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft

      21120 Someday Farm Ln, Leonardtown, MD 20650

      21120 Someday Farm Ln, Leonardtown, MD 20650
  • /3

    $175,000

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

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 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
  • /73

    $520,000 Sold Sep 19, 2025

    • 2,649 Sq Ft
    • $196/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    21158 Marigold St, Leonardtown, MD 20650

    Welcome to 21158 Marigold St, a beautifully maintained Colonial in the sought-after Kingston Estates community. This spacious home offers over 2,600 sq ft of living space on more than an acre, blending comfort, functionality, and privacy. It features 4 generously sized bedrooms, 2.5 bathrooms, a finished basement, and an updated kitchen with stainless steel appliances. Step outside to a peaceful,

    Jarred Green Real Broker, LLC

    21158 Marigold St, Leonardtown, MD 20650
    • /34

      Est $385,160 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft

      20440 Chingville Rd, Leonardtown, MD 20650

      20440 Chingville Rd, Leonardtown, MD 20650
  • /3

    $175,000

    • 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
  • /46

    $350,000 Sold Sep 19, 2025

    • 1,160 Sq Ft
    • $302/SF
    • 28 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1978

    22798 Lawrence Ave, Leonardtown, MD 20650

    Looking to be within walking distance to all of the amenities that Leonardtown Square has to offer? Look no further than this updated turn key townhome. You can stroll on the sidewalks to all of the local shops, restaurants, post office, and the waterfront park. Conveniently close to St. Mary's Hospital, Patuxent River Naval Air Station, and Solomons Island. No HOA, public water and public

    Barbara Click O'Brien Realty ERA Powered

    22798 Lawrence Ave, Leonardtown, MD 20650
    • /39

      Est $455,727 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft

      41464 Helen Marie Ct, Leonardtown, MD 20650

      41464 Helen Marie Ct, Leonardtown, MD 20650
  • /10

    $1,999,999

    • 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
  • /30

    $510,000 Sold Sep 19, 2025

    • 2,935 Sq Ft
    • $174/SF
    • 54 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1975

    22186 Monterey Place, Leonardtown, MD 20650

    Beautiful brick rambler is almost 3,000 SF overlooking lake and golf course on full, walk-out basement (2,059 SF) w/ attached 2 car garage. Kitchen boasts brand new stainless appliances, pantry and lovely lake view! Lots of table space in the kitchen area or the formal dining area. Both family room and rec room have wood burning fireplaces. This Mid-century/Modern open floorplan is a delight with

    Barbara Stellway KW Metro Center

    22186 Monterey Place, Leonardtown, MD 20650
    • /90

      Est $693,754 Not Listed For Sale

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

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      20746 Deer Wood Park Dr, 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
  • /48

    $469,900 Sold Sep 18, 2025

    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths

    23664 Dragonfly Ln, Leonardtown, MD 20650

    ***UNDER CONTRACT***Unit 86 Cumberland D1New 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,

    Laura Bernth RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
    • /55

      Est $556,710 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,546 Sq Ft

      23285 Joanne Dr, Leonardtown, MD 20650

      23285 Joanne Dr, Leonardtown, MD 20650
  • /40

    $449,900 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths

    lot 106-23683 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Builder to honor promotional pricing for contracts that close by 12/31/25. Unit 106 Madison D3: Welcome to Meadows at Town Run....Leonardtown’s

    Laura Bernth RE/MAX One

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

    $599,000 Sold Sep 18, 2025

    • 3,914 Sq Ft
    • $153/SF
    • 20 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1993

    23650 Rocky Ridge Ct, Leonardtown, MD 20650

    TWO HOUSES FOR THE PRICE OF ONE!** Perfect for a multi-family (in-laws, grown kids) or generating significant rental income. **MAIN HOUSE** offers 2,000 sq ft of single-story living with 3 bedrooms, 2 baths, expansive living & dining areas, hardwood floors, and tons of natural light. Laundry/mud room with a half bath and pantry off the 2-car garage is a bonus. **TWO-STORY GARAGE APARTMENT**

    Joseph Hawkins Hawkins Real Estate Company

    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    • /50

      Est $678,611 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,540 Sq Ft

      39994 Ben Morgan Rd, Leonardtown, MD 20650

      39994 Ben Morgan Rd, Leonardtown, MD 20650
  • /40

    $449,900 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths

    Lot 104- 23695 Dragonfly Ln, Leonardtown, MD 20650

    ***Immediate Delivery***Builder Incentive, BE HOME IN TIME FOR THE HOLIDAYS, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Builder to honor promotional pricing for contracts that close by 12/31/25. Unit 104 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s

    Laura Bernth RE/MAX One

    Lot 104- 23695 Dragonfly Ln, Leonardtown, MD 20650
  • /72

    $740,000 Sold Sep 18, 2025

    • 6,064 Sq Ft
    • $122/SF
    • 8 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2002

    40801 Kiskadee Ln, Leonardtown, MD 20650

    Welcome to 40801 Kiskadee Lane — a truly exceptional residence nestled on over 3 private acres in the prestigious waterfront community of Avenmar. This grand colonial home is an entertainer’s dream, offering over 6,000 square feet of beautifully designed living space, and is specially offered with the last available building lot in the community — an additional 3.5+ acre parcel for $200,000,

    Pattee McInerney Scott McInerney RE/MAX One

    40801 Kiskadee Ln, Leonardtown, MD 20650

Showing Results 121 - 160, Page 4 of 18

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