328

Recently Sold Homes near Leonardtown Middle School

Section Image
  • 23849 Point Lookout Rd, Leonardtown, MD 20650
    23849 Point Lookout Rd, Leonardtown, MD 20650
    23849 Point Lookout Rd, Leonardtown, MD 20650
    /37

    $355,000 Sold Oct 17, 2025

    • 1,092 Sq Ft
    • $325/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    23849 Point Lookout Rd, Leonardtown, MD 20650

    Excellent one level living in Leonardtown just past the high school, NO HOA, and sits on 1.5 acres of land. Front door was replaced in 2018; the rest of the doors and windows were replaced in 2025. Newer shingles replaced in 2015, the hall bathroom updated in 2024. Kitchen features a center island, which leads to a large outdoor deck for grilling and entertaining. Washer and dryer is being " sold

    Perry Hayden CENTURY 21 New Millennium

    23849 Point Lookout Rd, Leonardtown, MD 20650
  • 22323 Saint Clements Ave, Leonardtown, MD 20650
    22323 Saint Clements Ave, Leonardtown, MD 20650
    22323 Saint Clements Ave, Leonardtown, MD 20650
    /25

    $300,000 Sold Oct 15, 2025

    • 1,200 Sq Ft
    • $250/SF
    • 0 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1955

    22323 Saint Clements Ave, Leonardtown, MD 20650

    Welcome to 22323 Saint Clements Avenue, a rare and exciting opportunity to create your dream waterfront retreat or a lucrative investment property. Nestled on the serene shores of the Potomac River, this charming 2-bedroom, 2-bath cottage offers stunning water views, a private pier, and a detached garage—all on a generous lot in one of Southern Maryland’s most desirable waterfront

    Matthew Burgan Infinitas Realty Group

    22323 Saint Clements Ave, Leonardtown, MD 20650
  • 41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    /30

    $645,000 Sold Oct 15, 2025

    • 3,907 Sq Ft
    • $165/SF
    • 26 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2011

    41430 Whimsical Ct, Leonardtown, MD 20650

    Price Improvement!!!! This home is a MUST SEE!!!!Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful updates throughout, this home is perfect for

    Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
  • 23348 Lindsay Dr, Leonardtown, MD 20650
    23348 Lindsay Dr, Leonardtown, MD 20650
    23348 Lindsay Dr, Leonardtown, MD 20650
    /33

    $570,000 Sold Oct 15, 2025

    • 3,540 Sq Ft
    • $161/SF
    • 129 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2022

    23348 Lindsay Dr, Leonardtown, MD 20650

    Seller is offering 3% closing help!Welcome to 23348 Lindsay Drive — where space, style, and comfort come together in the heart of Leonardtown’s sought-after Clark’s Rest community. This nearly new 5-bedroom, 4-bath home offers over 3,500 sq ft of beautifully designed living space with thoughtful upgrades and a flexible floor plan perfect for modern living.Step inside to a

    Christi Turman-Rojas Fairfax Realty Premier

    23348 Lindsay Dr, Leonardtown, MD 20650
  • 23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    /76

    $619,000 Sold Oct 10, 2025

    • 3,806 Sq Ft
    • $163/SF
    • 32 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2023

    23092 Town Run Dr, Leonardtown, MD 20650

    Welcome home to The Meadows of Town Run, and this Montross floorplan built by QBHI. The Montross is an efficient floorplan with no wasted space. With 2600 sq ft of above grade living area, 4 bedrooms and 2.5 baths, this home lives comfortably for any family. The beautiful kitchen opens generously to both the living room and an extended morning room. The cozy deck, just off the morning room

    Robin Errington CENTURY 21 New Millennium

    23092 Town Run Dr, Leonardtown, MD 20650
  • 42264 Ridge Rd, Mechanicsville, MD 20659
    42264 Ridge Rd, Mechanicsville, MD 20659
    42264 Ridge Rd, Mechanicsville, MD 20659
    /33

    $195,000 Sold Oct 10, 2025

    • 2,020 Sq Ft
    • $97/SF
    • 106 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1950

    42264 Ridge Rd, Mechanicsville, MD 20659

    Investor alert! Great fix and flip! 4 bedroom (possibly 5) 2 bath SFH with detached garage and a guest house with 2 rooms, nice sized lot. Property sold AS-IS, CASH or HARD MONEY LOAN.

    Heidi Heiderman Samson Properties

    42264 Ridge Rd, Mechanicsville, MD 20659
  • Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
    /48

    $447,400 Sold Oct 09, 2025

    • 2,554 Sq Ft
    • $175/SF
    • 58 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650

    SOLD & SETTLED***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plus $12,500 in Closing Help OR $6,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company.Unit 87 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the

    Laura Bernth RE/MAX One

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
  • 41505 Knight Rd, Leonardtown, MD 20650
    41505 Knight Rd, Leonardtown, MD 20650
    41505 Knight Rd, Leonardtown, MD 20650
    /126

    $4,995,000 Sold Oct 08, 2025

    • 12,113 Sq Ft
    • $412/SF
    • 124 Days On Market
    • 5 Beds
    • 8 Baths
    • Built 2012

    41505 Knight Rd, Leonardtown, MD 20650

    Stunning. Welcome to a world of unparalleled luxury and breathtaking beauty. Nestled along the tranquil waters off of the Potomac River, this custom-built four level waterfront estate on almost 18 acres, is a testament to architectural brilliance and sophisticated design. As you approach the grand entrance, you are greeted by a circular driveway, detached 3-car garage, attached 2-car garage,

    Travis Gray Engel & Völkers Annapolis

    41505 Knight Rd, Leonardtown, MD 20650
  • Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    /55

    $464,900 Sold Oct 07, 2025

    • 2,966 Sq Ft
    • $157/SF
    • 54 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650

    ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 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. Unit 89 Oakley D1New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious

    Laura Bernth RE/MAX One

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
  • 24549 Fwd Dr, Hollywood, MD 20636
    24549 Fwd Dr, Hollywood, MD 20636
    24549 Fwd Dr, Hollywood, MD 20636
    /43

    $575,000 Sold Oct 03, 2025

    • 2,632 Sq Ft
    • $218/SF
    • 72 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1997

    24549 Fwd Dr, Hollywood, MD 20636

    Welcome to this beautiful 4-bedroom, 2.5-bath home that blends comfort, style, and functionality. Step inside to find a formal living room and a separate formal dining room—perfect for entertaining. Spacious kitchen features Cambria stone countertops and Porcelanosa tile flooring, combining beauty and durability. A cozy family room with a fireplace offers the ideal space to unwind, while a

    Florentina Killian CENTURY 21 New Millennium

    24549 Fwd Dr, Hollywood, MD 20636
  • 23080 Town Run Dr, Leonardtown, MD 20650
    23080 Town Run Dr, Leonardtown, MD 20650
    23080 Town Run Dr, Leonardtown, MD 20650
    /89

    $686,000 Sold Oct 02, 2025

    • 3,794 Sq Ft
    • $181/SF
    • 36 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2023

    23080 Town Run Dr, Leonardtown, MD 20650

    Welcome to this exceptionally upgraded Quality Built Homes Adelina model in the highly desirable Meadows at Town Run community in Leonardtown, Maryland. Built with nearly every available upgrade, this stunning home offers 5 bedrooms, 3.5 bathrooms, and nearly 3,800 square feet of finished living space, thoughtfully designed for comfort, function, and style.You’ll immediately appreciate

    Laura Bernth RE/MAX One

    23080 Town Run Dr, Leonardtown, MD 20650
  • 24424 Broad Creek Dr, Hollywood, MD 20636
    24424 Broad Creek Dr, Hollywood, MD 20636
    24424 Broad Creek Dr, Hollywood, MD 20636
    /65

    $532,000 Sold Oct 01, 2025

    • 2,522 Sq Ft
    • $211/SF
    • 49 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2010

    24424 Broad Creek Dr, Hollywood, MD 20636

    Welcome to 24424 Broad Creek Drive, a beautifully maintained 4-bedroom, 3.5-bath home offering 3,596 sq ft of living space! The main level showcases gleaming hardwood floors, a spacious eat-in kitchen that opens to the family room, and a separate dining room perfect for gatherings. Upstairs, you'll find a convenient laundry room and a luxurious primary suite featuring a walk-in closet and

    Katherine Dean RE/MAX One

    24424 Broad Creek Dr, Hollywood, MD 20636
  • 43571 Bayberry Ct, Leonardtown, MD 20650
    43571 Bayberry Ct, Leonardtown, MD 20650
    43571 Bayberry Ct, Leonardtown, MD 20650
    /59

    $600,000 Sold Oct 01, 2025

    • 2,946 Sq Ft
    • $204/SF
    • 22 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1993

    43571 Bayberry Ct, Leonardtown, MD 20650

    Gorgeous Colonial on a Beautifully Landscaped 4.26 Acre Premium Lot in the Sought After, Well-Established Neighborhood of Chestnut Ridge. A Welcoming Covered Front Porch leads to an Open Floor Plan with 9 Foot Ceilings and New Luxury Vinyl Plank (LVP) Flooring. Stylish Large Living Room with a Wood Burning Fireplace. Bright Kitchen with 48” Cabinetry, Gleaming Granite, and a Large Pantry. The

    Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
  • 21851 Peters Ct, California, MD 20619
    21851 Peters Ct, California, MD 20619
    21851 Peters Ct, California, MD 20619
    /40

    $375,000 Sold Sep 30, 2025

    • 1,300 Sq Ft
    • $288/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1981

    21851 Peters Ct, California, MD 20619

    Nestled away on a quiet cul-de-sac in California, this 1.5 acre well maintained rambler can be yours to start your new adventure! New septic and well '21, new roof '23, hvac in Dec '24, hot water heater '25 and appliances less than 5 years old all taking the worry out of this purchase. The full bath was more recently renovated and fresh paint throughout most of the home provide a clean updated

    Robin Errington CENTURY 21 New Millennium

    21851 Peters Ct, California, MD 20619
  • 23392 Marview Ct, Leonardtown, MD 20650
    23392 Marview Ct, Leonardtown, MD 20650
    23392 Marview Ct, Leonardtown, MD 20650
    /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
  • 43658 Redmond Rd, Leonardtown, MD 20650
    43658 Redmond Rd, Leonardtown, MD 20650
    43658 Redmond Rd, Leonardtown, MD 20650
    /16

    $281,650 Sold Sep 30, 2025

    • 2,078 Sq Ft
    • $136/SF
    • 12 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1959

    43658 Redmond Rd, Leonardtown, MD 20650

    DON'T MISS THIS FABULOUS OPPORTUNITY***FANTASTIC BRICK RAMBLER***4 BEDROOMS***2 CAR GARAGE***FORMAL DINING ROOM***HARDWOOD FLOORS***BRICK FIREPLACE***CHAINLINK FENCE***CEILING FANS***2 CAR CARPORT***ENJOY THE PEAR TREE***CENTRAL AIR***THIS HOME IS BEING SOLD COMPLETELY AS-IS***HURRY THIS PROPERTY WON'T LAST LONG**

    Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
  • 23246 Lindsay Dr, Leonardtown, MD 20650
    23246 Lindsay Dr, Leonardtown, MD 20650
    23246 Lindsay Dr, Leonardtown, MD 20650
    /34

    $625,000 Sold Sep 30, 2025

    • 3,876 Sq Ft
    • $161/SF
    • 55 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2017

    23246 Lindsay Dr, Leonardtown, MD 20650

    Clark's Rest Community:Welcome to this stunning 5-bedroom, 3.5-bath home with over 3,800 square feet of finished living space.Fully owned solar panels—no lease, no monthly payments—drastically reducing electric bills and increasing your home’s efficiency and value. Additional features include convenient attic access located above the 2-car garage, ideal for extra

    Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
  • 23674 Jm Gough Ct, Leonardtown, MD 20650
    23674 Jm Gough Ct, Leonardtown, MD 20650
    23674 Jm Gough Ct, Leonardtown, MD 20650
    /72

    $537,500 Sold Sep 30, 2025

    • 2,697 Sq Ft
    • $199/SF
    • 96 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    23674 Jm Gough Ct, Leonardtown, MD 20650

    Welcome home to this beautifully updated Colonial located in a charming and quiet Leonardtown neighborhood—just minutes from local restaurants, shopping, and all the conveniences of town living.Freshly painted throughout and featuring brand-new carpet, this 4-bedroom, 2.5-bath gem is move-in ready and full of modern upgrades. The heart of the home is a gourmet kitchen with upgraded stainless

    Heather Foster RE/MAX One

    23674 Jm Gough Ct, Leonardtown, MD 20650
  • 23647 Hansel Ct, Leonardtown, MD 20650
    23647 Hansel Ct, Leonardtown, MD 20650
    23647 Hansel Ct, Leonardtown, MD 20650
    /74

    $660,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,194 Sq Ft

    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
  • 23220 Brandon Ct, Leonardtown, MD 20650
    23220 Brandon Ct, Leonardtown, MD 20650
    23220 Brandon Ct, 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
  • 25371 Allston Ln, Hollywood, MD 20636
    25371 Allston Ln, Hollywood, MD 20636
    25371 Allston Ln, Hollywood, MD 20636
    /34

    $440,000 Sold Sep 26, 2025

    • 1,800 Sq Ft
    • $244/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1978

    25371 Allston Ln, Hollywood, MD 20636

    This charming two-story home is located in the Gillens Grove neighborhood and offers 4 bedrooms, 2.5 bathrooms, and a thoughtful blend of classic comfort with modern updates throughout the home.The main level features a foyer, formal living room, formal dining room, and a fully renovated kitchen. The newly renovated eat-in kitchen opens into a spacious den with built-in shelving and a cozy

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    25371 Allston Ln, Hollywood, MD 20636
  • 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

    • 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
  • 40480 Parsons Mill Rd, Leonardtown, MD 20650
    40480 Parsons Mill Rd, Leonardtown, MD 20650
    40480 Parsons Mill Rd, 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
  • 42346 Alan Ln, Mechanicsville, MD 20659
    42346 Alan Ln, Mechanicsville, MD 20659
    42346 Alan Ln, Mechanicsville, MD 20659
    /54

    $449,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    42346 Alan Ln, Mechanicsville, MD 20659

    Charming Rambler on Over 2 Acres - No HOA!Welcome home to this spacious 3-bedroom, 2-bath rambler offering the perfect blend of comfort, style, and convenience. The open floor plan featuring an updated kitchen with granite countertops, sleek stainless steel appliances, butler's pantry providing ample cabinetry for storage.A spacious primary bedroom, boasting a generous walk-in

    Tracey Summers CENTURY 21 New Millennium

    42346 Alan Ln, Mechanicsville, MD 20659
  • 21385 Fairwood Ct, Leonardtown, MD 20650
    21385 Fairwood Ct, Leonardtown, MD 20650
    21385 Fairwood Ct, 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
  • 40552 Breton Knolls Ct, Leonardtown, MD 20650
    40552 Breton Knolls Ct, Leonardtown, MD 20650
    40552 Breton Knolls Ct, Leonardtown, MD 20650
    /38

    $884,900 New Construction

    • 5 Beds
    • 2.5 Baths
    • 3,127 Sq Ft

    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
  • 26413 Hillendale Rd, Hollywood, MD 20636
    26413 Hillendale Rd, Hollywood, MD 20636
    26413 Hillendale Rd, Hollywood, MD 20636
    /42

    $359,900 Sold Sep 23, 2025

    • 1,152 Sq Ft
    • $312/SF
    • 44 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    26413 Hillendale Rd, Hollywood, MD 20636

    "Pride of Ownership" really shows in this Charming ,nicely landscaped, remodeled , energy efficient home with many recent modern upgrades! Don't miss this beautifully updated 3-bedroom, 2-full bath home featuring a brand-new roof, new heat pump, duct work, insulation, crawl space has new gravel and vapor barrier, fresh paint and stylish new vinyl plank flooring throughout. The spacious kitchen

    William Fitzgerald Fitzgerald Realty & Auctioneers

    26413 Hillendale Rd, Hollywood, MD 20636
  • 22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, Leonardtown, MD 20650
    22272 Orchard Ct, 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
  • 21158 Marigold St, Leonardtown, MD 20650
    21158 Marigold St, Leonardtown, MD 20650
    21158 Marigold St, 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
  • 22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, 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
  • 22186 Monterey Place, Leonardtown, MD 20650
    22186 Monterey Place, Leonardtown, MD 20650
    22186 Monterey Place, 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
  • 42190 Ridge Rd, Mechanicsville, MD 20659
    42190 Ridge Rd, Mechanicsville, MD 20659
    42190 Ridge Rd, Mechanicsville, MD 20659
    /35

    $299,999 Pending

    • 3 Beds
    • 1 Bath
    • 1,134 Sq Ft

    42190 Ridge Rd, Mechanicsville, MD 20659

    Adjusted to an unbelievable price. You won't find a house at this price that is practically brand new! Updated and cute as a button. Situated on a corner lot with a nice big yard, a shade tree and view of the woods across the street. This home has a new roof, vinyl plank flooring, appliances and HVAC. Freshly painted 3 bedrooms (one without a closet) living room, kitchen and bath. There's

    Trish Wallmark RE/MAX One

    42190 Ridge Rd, Mechanicsville, MD 20659
  • 23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, Leonardtown, MD 20650
    23664 Dragonfly Ln, 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
  • 40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee 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
  • 23650 Rocky Ridge Ct, Leonardtown, MD 20650
    23650 Rocky Ridge Ct, Leonardtown, MD 20650
    23650 Rocky Ridge Ct, 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
  • 23280 Hollywood Rd, Leonardtown, MD 20650
    23280 Hollywood Rd, Leonardtown, MD 20650
    23280 Hollywood Rd, Leonardtown, MD 20650
    /20

    $330,000 Sold Sep 16, 2025

    • 1,402 Sq Ft
    • $235/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    23280 Hollywood Rd, Leonardtown, MD 20650

    Charming Brick Home in Downtown Leonardtown!All-brick 3BR, 1,400 sq ft home on a 1/2-acre lot with public water and sewer. Features new windows, roof, and gutters, plus a spacious living/dining combo and family room.Walk to restaurants & shops—prime location in the heart of town! Estate sale. Subject to Orphan's court approval.

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23280 Hollywood Rd, Leonardtown, MD 20650
  • 21784 Potomac View Dr, Leonardtown, MD 20650
    21784 Potomac View Dr, Leonardtown, MD 20650
    /2

    $287,000 Sold Sep 15, 2025

    • 1,056 Sq Ft
    • $272/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1962

    21784 Potomac View Dr, Leonardtown, MD 20650

    Society Hill fixer-upper: 3 BR, 1 BA, approx. 1,100 sq ft, attached 1-car garage. Ready for updates—great potential to renovate and make it your own! Optional Breton Bay Community Association membership offers beach, pool, tennis, and golf access (membership/fees apply). Property details are estimated; buyer to verify all information. Just a short walk to the neighborhood beach, pier, and picnic

    Mike Benton Home Towne Real Estate

    21784 Potomac View Dr, Leonardtown, MD 20650
  • 20903 Jo Marie Way, Callaway, MD 20620
    20903 Jo Marie Way, Callaway, MD 20620
    20903 Jo Marie Way, Callaway, MD 20620
    /29

    $289,900 Sold Sep 15, 2025

    • 1,320 Sq Ft
    • $220/SF
    • 2 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1998

    20903 Jo Marie Way, Callaway, MD 20620

    Welcome home to this stunning 3 bedroom, 2.5 bath end unit townhome that has been thoughtfully updated throughout. Step inside to find brand-new LVP flooring throughout, fresh paint, and a recently upgraded master bath. The kitchen shines with new granite countertops, stainless steel appliances, and plenty of space for cooking. Other updates include a newer roof for peace of mind and much

    DJ Brady EXP Realty, LLC

    20903 Jo Marie Way, Callaway, MD 20620
  • 22530 Bull Rd, Leonardtown, MD 20650
    22530 Bull Rd, Leonardtown, MD 20650
    22530 Bull Rd, Leonardtown, MD 20650
    /27

    $575,000 Sold Sep 12, 2025

    • 1,976 Sq Ft
    • $291/SF
    • 3 Beds
    • 3 Baths
    • Built 1971

    22530 Bull Rd, Leonardtown, MD 20650

    Beautiful park-like setting on 8 acres featuring a family home and the unique Three Bears House! The main residence, built and lovingly cared for by the original owner, offers 3 bedrooms with hardwood floors and 2 full baths on the main level. A walk-out lower level includes a 3rd full bath, kitchenette, and spacious family room with a woodstove—ideal for gatherings or separate living

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    22530 Bull Rd, Leonardtown, MD 20650
  • 23330 Lindsay Dr, Leonardtown, MD 20650
    23330 Lindsay Dr, Leonardtown, MD 20650
    23330 Lindsay Dr, Leonardtown, MD 20650
    /26

    $584,000 Sold Sep 12, 2025

    • 1,926 Sq Ft
    • $303/SF
    • 0 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2022

    23330 Lindsay Dr, Leonardtown, MD 20650

    COMING SOON!!!! Rare opportunity in Clark's Rest. This beautiful home was built in 2022 and still looks and feels brand new!! This rear load garage home features 3 bedrooms/2 baths on the main level with just over 1880 sq feet of finished living space to enjoy. Basement is unfinished but does have a finished full bath and a window well perfect for a future bedroom opportunity. This

    Kristen Quinn Realty Navigator

    23330 Lindsay Dr, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 9

Maryland St Marys County Leonardtown Leonardtown Middle School

Recently Sold Real Estate & Homes near Leonardtown Middle School

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 © 2025 CoStar Group