159

Recently Sold Leonardtown, MD Homes

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  • 22542 Landing Way, Leonardtown, MD 20650
    22542 Landing Way, Leonardtown, MD 20650
    22542 Landing Way, Leonardtown, MD 20650
    /42

    $517,000 Sold Aug 27, 2025

    • 2,752 Sq Ft
    • $188/SF
    • 21 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2005

    22542 Landing Way, Leonardtown, MD 20650

    End Unit Townhome with Coastal Charm & Waterfront LivinEnd Unit Townhome with Coastal Charm & Waterfront Living This stunning 3-story end-unit townhome blends spacious living with coastal serenity in a picturesque waterfront community on Breton Bay. Just a short stroll from Leonardtown Square, you’ll enjoy easy access to shops, dining, and festive community events at the

    Trish Brow EXP Realty, LLC

    22542 Landing Way, Leonardtown, MD 20650
  • 40972 Mollies Way, Leonardtown, MD 20650
    40972 Mollies Way, Leonardtown, MD 20650
    40972 Mollies Way, Leonardtown, MD 20650
    /83

    $1,700,000 Sold Aug 21, 2025

    • 3,459 Sq Ft
    • $491/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1995

    40972 Mollies Way, Leonardtown, MD 20650

    Once in a Lifetime Potomac River Estate on 20+ AcresAt the end of a long, private drive, discover this breathtaking custom-built Potomac River waterfront 3459SQFT Colonial, nestled on 20.35 acres of pristine land with sweeping river views and a private pond. Built in 1995 by its original owners, this stunning 4-bedroom, 2.5-bath estate redefines timeless craftsmanship, luxurious design,

    Mark Frisco CENTURY 21 New Millennium

    40972 Mollies Way, Leonardtown, MD 20650
  • 41460 Challedon Way, Leonardtown, MD 20650
    41460 Challedon Way, Leonardtown, MD 20650
    /2

    $630,000 Sold Aug 20, 2025

    • 3,252 Sq Ft
    • $194/SF
    • 2 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2010

    41460 Challedon Way, Leonardtown, MD 20650

    Pride of ownership shines throughout this beautifully maintained Hayden model located in Leonard’s Grant community. From the moment you step inside, you'll be welcomed by neutral paint, beautiful flooring—including gleaming hardwoods, brand-new carpet, and luxury vinyl plank in the finished basement.The gourmet kitchen is truly the heart of the home, featuring updated appliances including a

    Heather Foster RE/MAX One

    41460 Challedon Way, Leonardtown, MD 20650
  • 22190 Bull Rd, Leonardtown, MD 20650
    22190 Bull Rd, Leonardtown, MD 20650
    /2

    $400,000 Sold Aug 18, 2025

    • 1,380 Sq Ft
    • $290/SF
    • 3 Beds
    • 2 Baths
    • Built 1987

    22190 Bull Rd, Leonardtown, MD 20650

    Adorable three-bedroom 2-bathroom rambler in Breton Bay Community. Sunroom out of the primary suite and deck. New HVAC system installed on August 23. New water heater installed in 2021. Updated kitchen with granite countertops. There is a two-car garage door, but the inside of the garage has been modified, and an additional storage room has been added. Large shed with electricity and storage

    Gabriela Agostinelli RE/MAX Realty Group

    22190 Bull Rd, Leonardtown, MD 20650
  • 23888 Hollywood Rd, Leonardtown, MD 20650
    23888 Hollywood Rd, Leonardtown, MD 20650
    23888 Hollywood Rd, Leonardtown, MD 20650
    /25

    $400,000 Sold Aug 15, 2025

    • 1,450 Sq Ft
    • $276/SF
    • 3 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1972

    23888 Hollywood Rd, Leonardtown, MD 20650

    Modern Charm Meets Country! Welcome to your private retreat in the heart of Leonardtown! This completely updated 4-bedroom, 2-bath rambler sits on 1.3 acres of peace and privacy—tucked off the road and surrounded by nature. Inside, you'll fall in love with the wide-open layout, fresh neutral tones, and stunning luxury vinyl flooring that flows seamlessly throughout.The

    Mark Frisco CENTURY 21 New Millennium

    23888 Hollywood Rd, Leonardtown, MD 20650
  • 20755 Deer Wood Park Dr, Leonardtown, MD 20650
    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    20755 Deer Wood Park Dr, Leonardtown, MD 20650
    /27

    $515,000 Sold Aug 15, 2025

    • 2,538 Sq Ft
    • $203/SF
    • 10 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1996

    20755 Deer Wood Park Dr, Leonardtown, MD 20650

    Welcome to your dream home in the desirable Chestnut Hills community of Leonardtown, Maryland! This charming 4-bedroom, 2.5-bathroom single-family home offers a perfect blend of space, comfort, and privacy, all set on an impressive 4.24 acres. With 2,538 square feet of living space, this residence features beautiful hardwood floors throughout, adding a warm and inviting touch.The heart of

    Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
  • 41115 Paw Hollow Ln, Leonardtown, MD 20650
    41115 Paw Hollow Ln, Leonardtown, MD 20650
    41115 Paw Hollow Ln, Leonardtown, MD 20650
    /140

    $750,000 Sold Aug 15, 2025

    • 6,116 Sq Ft
    • $123/SF
    • 49 Days On Market
    • 4 Beds
    • 5.5 Baths
    • Built 1997

    41115 Paw Hollow Ln, Leonardtown, MD 20650

    Stunning Brick Front Colonial in Paw Paw Hollow - 1.8 Acres of Private LuxuryWelcome to this well maintained and beautifully designed brick front Colonial in the highly sought-after Paw Paw Hollow. This spacious 4-bedroom, 5.5-bathroom home offers over 5,000 square feet of living space on a generous 1.8-acre lot, providing the perfect blend of comfort, elegance, and privacy.Main Level

    Jennifer Goddard CENTURY 21 New Millennium

    41115 Paw Hollow Ln, Leonardtown, MD 20650
  • 44074 Medleys Neck Rd, Leonardtown, MD 20650
    44074 Medleys Neck Rd, Leonardtown, MD 20650
    44074 Medleys Neck Rd, Leonardtown, MD 20650
    /82

    $675,000 Sold Aug 14, 2025

    • 3,830 Sq Ft
    • $176/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2006

    44074 Medleys Neck Rd, Leonardtown, MD 20650

    Lovely rambler sitting on over 2 private acres in Leonardtown is looking for new owners. Main level has 4 bedrooms, 2 full baths, open kitchen/dining area with stone gas fireplace, laundry room and spacious family room. Primary bedroom has vaulted ceiling, walk in closet and large en-suite bath with separate tiled shower and soaking tub. Lower level is finished with rec area, wet bar, rough-in

    Cynthia Ballard CENTURY 21 New Millennium

    44074 Medleys Neck Rd, Leonardtown, MD 20650
  • 23275 Jenifer Ct, Leonardtown, MD 20650
    23275 Jenifer Ct, Leonardtown, MD 20650
    23275 Jenifer Ct, Leonardtown, MD 20650
    /113

    $638,000 Sold Aug 12, 2025

    • 6,311 Sq Ft
    • $101/SF
    • 86 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2005

    23275 Jenifer Ct, Leonardtown, MD 20650

    Welcome to this three-level home located in the Single Tree community, just a short walk from vibrant downtown. Boasting over 6,700 square feet of beautifully designed living space, this home offers 6 bedrooms, 4.5 bathrooms, and a thoughtfully crafted layout perfect for both everyday living and entertaining.The main level features gleaming hardwood floors, a soaring two-story family room

    Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
  • 20837 Camp Cosoma Rd, Leonardtown, MD 20650
    20837 Camp Cosoma Rd, Leonardtown, MD 20650
    20837 Camp Cosoma Rd, Leonardtown, MD 20650
    /3

    $212,000 Sold Aug 11, 2025

    • 1,016 Sq Ft
    • $209/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1950

    20837 Camp Cosoma Rd, Leonardtown, MD 20650

    Charming 2-bedroom, 1-bath home nestled on 2.31 acres just a short walk from St. Mary's Lake. Enjoy one-level living with a spacious living room, large eat-in kitchen, large mudroom and separate utility room, plus a relaxing screened porch and equally relaxing and peaceful, tree-lined backyard. The home offers a generous front yard with ample space for gardening and outdoor activities. Make sure

    Jennifer Goddard CENTURY 21 New Millennium

    20837 Camp Cosoma Rd, Leonardtown, MD 20650
  • 23265 Lindsay Dr, Leonardtown, MD 20650
    23265 Lindsay Dr, Leonardtown, MD 20650
    23265 Lindsay Dr, Leonardtown, MD 20650
    /59

    $435,000 Sold Aug 07, 2025

    • 2,306 Sq Ft
    • $189/SF
    • 3 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2017

    23265 Lindsay Dr, Leonardtown, MD 20650

    Welcome Home to this stunning 3 Bedroom, 3.5 Bath Townhome in the vibrant community of Clarks Rest in the heart of Leonardtown! Step inside this bright and open floorplan featuring 9 foot ceilings and gleaming hardwood floors throughout the main level. The dining room moves effortlessly to the well-appointed kitchen boasting gourmet Stainless Steel appliances, granite countertops, a large

    Wayne & Christine Floyd RE/MAX Realty Group

    23265 Lindsay Dr, Leonardtown, MD 20650
  • 41554 Briarwood Cir, Leonardtown, MD 20650
    41554 Briarwood Cir, Leonardtown, MD 20650
    41554 Briarwood Cir, Leonardtown, MD 20650
    /72

    $449,900 Sold Jul 31, 2025

    • 2,379 Sq Ft
    • $189/SF
    • 12 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    41554 Briarwood Cir, Leonardtown, MD 20650

    Location is key.... Not just in Leonardtown, but in the community itself. Through every window of the rear of this house is the picturesque setting of the wooded tree line and abundant privacy, not often found in Townhome living. This home is tucked back from main road on an open green in front and woods in the rear. Upgrades to this home from original build include: Premium COREtec Pro Plus

    Wayne & Christine Floyd RE/MAX Realty Group

    41554 Briarwood Cir, Leonardtown, MD 20650
  • 41997 Loker Ct, Leonardtown, MD 20650
    41997 Loker Ct, Leonardtown, MD 20650
    41997 Loker Ct, Leonardtown, MD 20650
    /41

    $479,900 Sold Jul 31, 2025

    • 2,330 Sq Ft
    • $206/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    41997 Loker Ct, Leonardtown, MD 20650

    Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn

    Jimmy Hayden RE/MAX Realty Group

    41997 Loker Ct, Leonardtown, MD 20650
  • 23745 Hicks Dr, Leonardtown, MD 20650
    23745 Hicks Dr, Leonardtown, MD 20650
    23745 Hicks Dr, Leonardtown, MD 20650
    /50

    $406,000 Sold Jul 25, 2025

    • 984 Sq Ft
    • $413/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    23745 Hicks Dr, Leonardtown, MD 20650

    Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location—all with no HOA.Inside, you’ll find a bright and open layout featuring wide plank flooring, recessed

    Neil Smith Blackwell Real Estate, LLC

    23745 Hicks Dr, Leonardtown, MD 20650
  • 21549 Point Lookout Rd, Leonardtown, MD 20650
    21549 Point Lookout Rd, Leonardtown, MD 20650
    21549 Point Lookout Rd, Leonardtown, MD 20650
    /43

    $710,000 Sold Jul 24, 2025

    • 3,153 Sq Ft
    • $225/SF
    • 6 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2001

    21549 Point Lookout Rd, Leonardtown, MD 20650

    Contemporary Farmhouse Living on over 24 acres! Drive down the lane past some of your pasture acreage on the left to your 3,000+ sf home backing to mature trees and wooded trails. A small pond is also located on the property. Possibilities abound with the level acreage in front! The property is located between Leonardtown and Callaway close to the Saint Mary's Rive State Park area. Close to

    MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
  • 23075 Hollywood Rd, Leonardtown, MD 20650
    23075 Hollywood Rd, Leonardtown, MD 20650
    23075 Hollywood Rd, Leonardtown, MD 20650
    /82

    $574,000 Sold Jul 24, 2025

    • 3,238 Sq Ft
    • $177/SF
    • 55 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1942

    23075 Hollywood Rd, Leonardtown, MD 20650

    Seller offering up to 3% in Closing assistance - Close in July, just in time for summer in Leonardtown! Built in 1942, this 5-bedroom, 2.5-bath home offers over 3,200 square feet of character-filled living space Original hardwood floors, arched openings, detailed trim work, and vintage glass door knobs are just a few of the timeless details that give this home its warmth and soul—while

    Katy Galloway CENTURY 21 New Millennium

    23075 Hollywood Rd, Leonardtown, MD 20650
  • 21143 Catnip Ct, Leonardtown, MD 20650
    21143 Catnip Ct, Leonardtown, MD 20650
    21143 Catnip Ct, Leonardtown, MD 20650
    /69

    $622,500 Sold Jul 21, 2025

    • 2,642 Sq Ft
    • $236/SF
    • 16 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2003

    21143 Catnip Ct, Leonardtown, MD 20650

    Welcome to this stunning 4-bedroom, 2.5-bath home in the desirable Kingston Estatesneighborhood of Leonardtown. Lovingly maintained by the original owners, this homesits on a beautifully landscaped lot of nearly an acre, and is nestled in a quiet cul-de-sacthat offers both privacy and convenience.As you step inside, you’ll be greeted by the stunning Acacia wood floors that

    Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, Leonardtown, MD 20650
  • 42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    42239 Riverwinds Dr, Leonardtown, MD 20650
    /42

    $906,500 Sold Jul 18, 2025

    • 2,167 Sq Ft
    • $418/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    42239 Riverwinds Dr, Leonardtown, MD 20650

    Welcome to your waterfront retreat on the Potomac River! This well-maintained 3-bedroom, 2.5-bath rambler is perfectly situated on a level 1-acre lot with stunning panoramic water views from every rear-facing room, including all bedrooms. The spacious kitchen opens to a cozy family room with a wood-burning fireplace, ideal for relaxing or entertaining. Step out to the screened-in porch or

    Connie Fitzgerald RE/MAX One

    42239 Riverwinds Dr, Leonardtown, MD 20650
  • 41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    41699 Courthouse Dr, Leonardtown, MD 20650
    /54

    $531,000 Sold Jul 18, 2025

    • 2,420 Sq Ft
    • $219/SF
    • 5 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2012

    41699 Courthouse Dr, Leonardtown, MD 20650

    Welcome to 41699 Courthouse Drive, a well-maintained home tucked away on a private lot in the heart of historic Leonardtown. Offering comfort, space, and small-town charm, this property is perfectly positioned with no HOA, public water and sewer, and easy access to everything Leonardtown has to offer.Inside, you’ll find a bright kitchen with plenty of cabinetry, an inviting dining area,

    Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, Leonardtown, MD 20650
  • 43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    43985 Main Way Rd, Leonardtown, MD 20650
    /74

    $475,000 Sold Jul 15, 2025

    • 2,400 Sq Ft
    • $198/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    43985 Main Way Rd, Leonardtown, MD 20650

    HUGE COVERED FRONT PORCH (12X18) INVITES YOU TO THIS AMAZINGLY WELL MAINTAINED RAMBLER IN DESIRABLE LANEDON NEIGHBORHOOD WITH DEEDED WATER ACCESS! 3/4 BEDROOMS; 4TH BEDROOM/CRAFT ROOM HAS ACCESS TO UNFINISHED SPACE FOR STORAGE. HARDWOOD FLOORS IN ALL ROOMS EXCEPT KITCHEN AND FAMILY ROOM. FORMAL LIVING ROOM AND SEPARATE DINING ROOM; PERFECT FOR THOSE FAMILY GATHERINGS AND HOLIDAY DINNERS. GOOD

    Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way Rd, Leonardtown, MD 20650
  • 23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    23278 Applewood Ln, Leonardtown, MD 20650
    /47

    $660,000 Sold Jul 14, 2025

    • 4,306 Sq Ft
    • $153/SF
    • 10 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23278 Applewood Ln, Leonardtown, MD 20650

    Absolutely stunning home in a premier location! Welcome to 23278 Applewood Ln in the sought-after Clark’s Rest community, directly across from the pool, sports courts, and clubhouse! All 4,000 sqft of living space is in pristine condition. From the moment you enter, you will love all of the natural light throughout. The jewel of the home is the expansive kitchen, curated with upgrades for your

    Jonathan Benya EXP Realty, LLC

    23278 Applewood Ln, Leonardtown, MD 20650
  • 23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    /75

    $595,000 Sold Jul 11, 2025

    • 3,188 Sq Ft
    • $187/SF
    • 29 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2011

    23578 Pine Bluff Way, Leonardtown, MD 20650

    LOCATION...LOCATION...LOCATION! THIS LOVELY HAYDEN MODEL IS NESTLED RIGHT AT THE HEAD OF THE VILLAGE GREEN IN DESIRABLE LEONARD'S GRANT NEIGHBORHOOD. 3 BEDROOMS AND 2 FULL BATHS ON SECOND LEVEL AND A PARTIALLY FINISHED BASEMENT TO INCLUDE REC ROOM AND FULL BATH. UNFINISHED SPACE COULD BE FINISHED FOR THE 4TH BEDROOM OR GREAT STORAGE. OPEN FLOOR PLAN FEATURES HARDWOOD FLOORS, GRANITE

    Jennifer Mullennix CENTURY 21 New Millennium

    23578 Pine Bluff Way, Leonardtown, MD 20650
  • 23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    /88

    $685,000 Sold Jul 10, 2025

    • 4,267 Sq Ft
    • $161/SF
    • 6 Beds
    • 3.5 Baths
    • Built 2008

    23558 Belmar Dr, Leonardtown, MD 20650

    Beautiful house in the desired neighborhood of Leonard’s Grand in Leonardtown! This house has many unique characteristics! All new carpet! As you walk in to the hardwood entryway, you’ll notice the gorgeous staircase. This level includes a dining room, custom butler’s pantry and a large, upgraded kitchen. The transom windows are gorgeous and bring in a ton of natural light. These cabinets

    Heather Foster RE/MAX One

    23558 Belmar Dr, Leonardtown, MD 20650
  • 40905 Knight Rd, Leonardtown, MD 20650
    40905 Knight Rd, Leonardtown, MD 20650
    40905 Knight Rd, Leonardtown, MD 20650
    /43

    $445,000 Sold Jul 08, 2025

    • 1,820 Sq Ft
    • $245/SF
    • 82 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    40905 Knight Rd, Leonardtown, MD 20650

    Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland!This charming home blends comfort and functionality with three spacious bedrooms, 2.5 baths, and a layout that’s perfect for both everyday living and entertaining.Set on a generous half-acre lot, the fully fenced backyard offers plenty of room to enjoy the outdoors. Whether you're hosting a summer barbecue or winding

    Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
  • 23055 Town Run Dr, Leonardtown, MD 20650
    23055 Town Run Dr, Leonardtown, MD 20650
    23055 Town Run Dr, Leonardtown, MD 20650
    /85

    $695,000 Sold Jul 02, 2025

    • 4,019 Sq Ft
    • $173/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    23055 Town Run Dr, Leonardtown, MD 20650

    Stunning Clarke Model by Quality Built HomesLocated in the desirable Meadows at Town Run, this 4-bedroom, 3.5-bath home offers over 4,000 square feet of living space, including a finished lower level. Built in 2021, this home is just a few years old and has been meticulously maintained.Enjoy a prime location with Duke Elementary and the library within walking distance, Downtown

    Laura Bernth RE/MAX One

    23055 Town Run Dr, Leonardtown, MD 20650
  • 21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    /70

    $625,000 Sold Jul 02, 2025

    • 3,664 Sq Ft
    • $171/SF
    • 69 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1997

    21897 Fairway Dr, Leonardtown, MD 20650

    Qualified VA buyers using their own entitlement can assume the current 2.25% VA loan.Custom-Built Beauty Overlooking Breton Bay Golf Course! Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunning 5-bedroom, 2.5-bath custom-built home in the desirable Breton Bay community. This home is in impeccable condition with numerous upgrades—simply move right in and start enjoying luxury

    Matthew Burgan Infinitas Realty Group

    21897 Fairway Dr, Leonardtown, MD 20650
  • 23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    /64

    $1,100,000 Sold Jul 01, 2025

    • 6,508 Sq Ft
    • $169/SF
    • 7 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2009

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650

    Exceptional Private Estate with Detached Efficiency Apartment, Greenhouse, & Extensive Upgrades.Beautifully maintained and thoughtfully updated, this 5 BR, 6.5 BA custom estate offers space, privacy, and versatility in a stunning setting. A long, private farm lane leads to a solar-powered gated entry and professionally landscaped grounds, including wooden and wire fencing designed with

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
  • 23433 Grovewood Ct, Leonardtown, MD 20650
    23433 Grovewood Ct, Leonardtown, MD 20650
    23433 Grovewood Ct, Leonardtown, MD 20650
    /78

    $519,000 Sold Jul 01, 2025

    • 2,804 Sq Ft
    • $185/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23433 Grovewood Ct, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest Community. *OPEN HOUSE* Saturday, May 3rd from 11-2.Welcome to this beautifully maintained, "nearly-new" end-unit townhome in the desirable Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views. The chef-inspired kitchen is a dream, showcasing granite countertops, a

    Wayne & Christine Floyd RE/MAX Realty Group

    23433 Grovewood Ct, Leonardtown, MD 20650
  • 41572 Briarwood Cir, Leonardtown, MD 20650
    41572 Briarwood Cir, Leonardtown, MD 20650
    41572 Briarwood Cir, Leonardtown, MD 20650
    /80

    $505,000 Sold Jun 30, 2025

    • 2,850 Sq Ft
    • $177/SF
    • 55 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    41572 Briarwood Cir, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest. Welcome to this beautifully maintained, nearly-new end-unit townhome in the sought-after Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views from both the rear and side.Step inside to a spacious main level featuring luxury vinyl plank flooring and a convenient bonus

    Wayne & Christine Floyd RE/MAX Realty Group

    41572 Briarwood Cir, Leonardtown, MD 20650
  • 44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    /97

    $640,000 Sold Jun 29, 2025

    • 3,635 Sq Ft
    • $176/SF
    • 10 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1999

    44114 Woodmont Dr, Leonardtown, MD 20650

    NO SHOWINGS UNTILL THE OPEN HOUSE MAY 24, SAT 11-2.Exceptional 5-Bedroom Home on 2 Acres. Welcome to this gorgeous 5-bedroom, 3.5-bath custom home, perfectly situated on a beautifully landscaped 2-acre lot. Impeccably maintained and thoughtfully designed, this property offers an ideal blend of luxury, comfort, and practicality. All five bedrooms are located on the upper level, including a

    Lori Jean Buongiovanni (Hethmon) RE/MAX Realty Group

    44114 Woodmont Dr, Leonardtown, MD 20650
  • 20540 Deer Wood Park Dr, Leonardtown, MD 20650
    20540 Deer Wood Park Dr, Leonardtown, MD 20650
    20540 Deer Wood Park Dr, Leonardtown, MD 20650
    /34

    $615,000 Sold Jun 27, 2025

    • 3,850 Sq Ft
    • $160/SF
    • 9 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1995

    20540 Deer Wood Park Dr, Leonardtown, MD 20650

    Welcome to this beautiful contemporary colonial situated on over two private acres in the desirable community of Chestnut Hills. As you step inside, you will be greeted by three fully finished levels of warmth and comfort to include a soaring great room with walls of windows and a main level office. This thoughtfully designed home has been meticulously maintained and offers four generously

    Kelly Parks Coldwell Banker Realty

    20540 Deer Wood Park Dr, Leonardtown, MD 20650
  • 42439 Dean Forest Ct, Leonardtown, MD 20650
    42439 Dean Forest Ct, Leonardtown, MD 20650
    42439 Dean Forest Ct, Leonardtown, MD 20650
    /31

    $579,000 Sold Jun 26, 2025

    • 2,519 Sq Ft
    • $230/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2003

    42439 Dean Forest Ct, Leonardtown, MD 20650

    Welcome home to this beautiful 5 Bedroom 3.5 Bath Colonial in Leonardtown!! You will not want to miss this one! This home features a fully renovated kitchen done in 2024, includes a massive kitchen island, tons of counter space, all granite with a quartz back splash, new SS appliances, cabinets, recessed lighting. and new Porcelain kitchen floors. Beautiful Hand Scraped Hickory engineered wood

    DJ Brady EXP Realty, LLC

    42439 Dean Forest Ct, Leonardtown, MD 20650
  • 42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    /71

    $599,900 Sold Jun 25, 2025

    • 3,233 Sq Ft
    • $186/SF
    • 18 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    42261 Bird Haven Dr, Leonardtown, MD 20650

    Welcome to this charming 4-bedroom, 3.5-bathroom home nestled in the sought-after Kingston Estates of Leonardtown. Lovingly maintained by its original owners, this house seamlessly blends comfort, convenience and tranquility.Upon entering, you're greeted by bright and airy living spaces adorned with gorgeous wood floors that flow throughout much of the main level. The heart of the home is

    Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
  • 21821 Cove Ln, Leonardtown, MD 20650
    21821 Cove Ln, Leonardtown, MD 20650
    21821 Cove Ln, Leonardtown, MD 20650
    /17

    $685,000 Sold Jun 20, 2025

    • 2,748 Sq Ft
    • $249/SF
    • 2 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1967

    21821 Cove Ln, Leonardtown, MD 20650

    Choice location, private point on Cherry Cove with outstanding views of Cherry Cove & Breton Bay. Solid brick rambler with lots of options; generous office could easily be converted into 3rd bedroom....sun room, family room and formal living room with fireplace. Home needs updating. A stunning, private, convenient location!

    Barbara Stellway KW Metro Center

    21821 Cove Ln, Leonardtown, MD 20650
  • 41925 Nazareth Ct, Leonardtown, MD 20650
    41925 Nazareth Ct, Leonardtown, MD 20650
    41925 Nazareth Ct, Leonardtown, MD 20650
    /75

    $465,000 Sold Jun 20, 2025

    • 2,512 Sq Ft
    • $185/SF
    • 56 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2005

    41925 Nazareth Ct, Leonardtown, MD 20650

    DESIRED SCHOOL DISTRICT, SUBDIVISION & TOWN! 3 LEVELS of SPACIOUS LIVING! This beautiful Colonial home is nestled in the highly sought-after Academy Hill subdivision of Historic Leonardtown. Sitting on an end lot that backs to trees on .27 acres, it boasts a fenced backyard with a durable 2-year-old vinyl privacy fence —an ideal setting for privacy and entertaining on your deck. The three-level

    Dawn Bell RE/MAX One

    41925 Nazareth Ct, Leonardtown, MD 20650
  • 42279 Bird Haven Dr, Leonardtown, MD 20650
    42279 Bird Haven Dr, Leonardtown, MD 20650
    42279 Bird Haven Dr, Leonardtown, MD 20650
    /65

    $600,000 Sold Jun 17, 2025

    • 3,139 Sq Ft
    • $191/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2002

    42279 Bird Haven Dr, Leonardtown, MD 20650

    Beautiful home located in the desirable Leonardtown neighborhood of Kingston, this home features 5 bedrooms and 3.5 Baths . The main level features a large kitchen with granite counter tops and stainless steel appliances, spacious family room with wood burning fireplace, a home office with built-in storage, and formal dining room. The primary suite located on the second level features a large

    Mike Jordan CENTURY 21 New Millennium

    42279 Bird Haven Dr, Leonardtown, MD 20650
  • 20640 Laurel Ct, Leonardtown, MD 20650
    20640 Laurel Ct, Leonardtown, MD 20650
    20640 Laurel Ct, Leonardtown, MD 20650
    /54

    $635,000 Sold Jun 16, 2025

    • 2,692 Sq Ft
    • $236/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    20640 Laurel Ct, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY MONDAY MAY 19th at NOON! Welcome to your own private retreat with a sparkling in-ground pool! This beautifully maintained 4-bedroom, 3.5-bath rambler is nestled on just under 3 serene acres in popular Chestnut Hills. With a sprawling main level and a massive 2,700+ sq ft unfinished walk-out basement, this home has the potential to offer over 5,500 total square feet of

    Sarah Mulford-Martin EXP Realty, LLC

    20640 Laurel Ct, Leonardtown, MD 20650
  • 23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    /61

    $440,000 Sold Jun 16, 2025

    • 2,379 Sq Ft
    • $185/SF
    • 46 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    23445 Grovewood Ct, Leonardtown, MD 20650

    Welcome to 23445 Grovewood Court, an exquisitely maintained residence in the esteemed Clark's Rest community, where sophistication and serenity converge. This splendid 3-bedroom, 3.5-bath townhome offers an elevated living experience, combining impeccable design with unparalleled comfort. Step inside to discover an expansive and luminous open-concept floor plan, enhanced by refined finishes and

    John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
  • 44662 Blake Creek Rd, Leonardtown, MD 20650
    44662 Blake Creek Rd, Leonardtown, MD 20650
    44662 Blake Creek Rd, Leonardtown, MD 20650
    /6

    $320,500 Sold Jun 13, 2025

    • 1,344 Sq Ft
    • $238/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1963

    44662 Blake Creek Rd, Leonardtown, MD 20650

    This cozy cottage is located in a beautiful, peaceful setting with over an acre of mature fruit trees and flowers. This solid home, with its good bones, awaits a refreshing touch, making it an ideal project for investors or enthusiastic DIY buyers looking to create their dream space. Offered as is, this cottage holds great potential to become a truly special retreat.

    Ruth Mudd RE/MAX One

    44662 Blake Creek Rd, Leonardtown, MD 20650
  • 40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    /76

    $460,000 Sold Jun 12, 2025

    • 2,524 Sq Ft
    • $182/SF
    • 61 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    Have you been searching for a home with the PERFECT Water Views!! Without; the Water view price??This home may be what your heart Desires!! Walk your kayaks right down the SAME block to the community beach access spot. The "walking beach" as they call it. This home has water views from BOTH levels. There are wood burning stoves on BOTH levels. The main beach access with playground and pavilion

    Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 4

Maryland St Marys County Leonardtown

Recently Sold Real Estate & Homes in Leonardtown, MD

Frequently Asked Questions

What is the average home price in Leonardtown, MD?
Homes for sale in Leonardtown, MD have an average home price of $603,396.
What is the average time to sell a house in Leonardtown, MD?
The houses for sale in Leonardtown, MD spend an average of 29 days on the market.
What is the number of active homes for sale in Leonardtown, MD?
There are 26 active homes for sale in Leonardtown, MD.
How many homes have sold over the last 12 months in Leonardtown, MD?
135 homes have sold in Leonardtown, MD over the last 12 months.

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 29 days on the market compared to the national average of 52 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $549,900, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$549,900
Median Single Family Sale Price
$597,000
Median Townhouse Sale Price
$439,900
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$190
Number of Homes for Sale
26
Last 12 months Home Sales
135
Months of Supply
2.30
Median List Price
$552,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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