165

Recently Sold Homes in 20650

Section Image
  • 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
  • 23635 Abraham Dr, Leonardtown, MD 20650
    23635 Abraham Dr, Leonardtown, MD 20650
    23635 Abraham Dr, Leonardtown, MD 20650
    /41

    $572,000 Sold Jun 09, 2025

    • 3,272 Sq Ft
    • $175/SF
    • 2 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 2004

    23635 Abraham Dr, Leonardtown, MD 20650

    Welcome Home to Comfort, Charm, and SpaceThis stunning Colonial is nestled in a peaceful, sought-after community — the perfect retreat with 6 bedrooms and 4 full baths. Just minutes from downtown Leonardtown, you’ll have easy access to charming shops, popular restaurants, and scenic waterfront views at the Wharf.From the moment you enter, you’ll feel right at home. The warm and inviting family

    Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
  • 39880 Lady Baltimore Ave, Leonardtown, MD 20650
    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    /51

    $415,000 Sold Jun 09, 2025

    • 1,348 Sq Ft
    • $308/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new vinyl flooring throughout, the Roof was replaced in 2019, the appliances are less than 2 years old, the Heat Pump was replaced in 2020, and much much more!This home features a huge pantry in the kitchen, a huge laundry room with even more cabinets for storage, a beautiful

    Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
  • 21684 Potomac View Dr, Leonardtown, MD 20650
    21684 Potomac View Dr, Leonardtown, MD 20650
    21684 Potomac View Dr, Leonardtown, MD 20650
    /25

    $447,000 Sold Jun 04, 2025

    • 1,504 Sq Ft
    • $297/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    21684 Potomac View Dr, Leonardtown, MD 20650

    3BR, 2Bath rancher with Front and Rear covered porches. Rear yard is ready for outdoor entertainment. Large side load garage with storage area over. Living Room with fireplace, dining area, open kitchen. No mandatory HOA, however the civic association is an optional fee.HVAC replaced a year ago.

    Terry Tenney Atlantic Southern Realty INC

    21684 Potomac View Dr, Leonardtown, MD 20650
  • 20161 Tower Hill Rd, Leonardtown, MD 20650
    20161 Tower Hill Rd, Leonardtown, MD 20650
    20161 Tower Hill Rd, Leonardtown, MD 20650
    /56

    $395,000 Sold Jun 02, 2025

    • 1,661 Sq Ft
    • $238/SF
    • 2 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1990

    20161 Tower Hill Rd, Leonardtown, MD 20650

    This contemporary cape cod style home is it's own private retreat on over 3 acres. The main floor gives you a formal living room with vaulted celing and 2 sided woodstove/fireplace while also providing an additional family room that could easily be converted to a 3rd bedroom. The kitchen has been updated with granite counter tops, subway tiled backsplash, new appliances and more. Dining room

    Trish Wallmark RE/MAX One

    20161 Tower Hill Rd, Leonardtown, MD 20650
  • 41918 Sara Ann Ct, Leonardtown, MD 20650
    41918 Sara Ann Ct, Leonardtown, MD 20650
    41918 Sara Ann Ct, Leonardtown, MD 20650
    /33

    $505,000 Sold Jun 02, 2025

    • 3,392 Sq Ft
    • $149/SF
    • 12 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2005

    41918 Sara Ann Ct, Leonardtown, MD 20650

    This beautiful two-story Colonial with a finished basement is perfectly situated in a prime location just minutes from downtown Leonardtown, offering easy access to quaint shops, restaurants, the wharf, and vibrant community events. With a traditional floor plan, the main level features durable vinyl plank flooring, a welcoming living room with a cozy gas fireplace, and a functional kitchen with

    Tracey Summers CENTURY 21 New Millennium

    41918 Sara Ann Ct, Leonardtown, MD 20650
  • 22855 White Swan Way, Leonardtown, MD 20650
    22855 White Swan Way, Leonardtown, MD 20650
    22855 White Swan Way, Leonardtown, MD 20650
    /46

    $950,000 Sold Jun 02, 2025

    • 6,762 Sq Ft
    • $140/SF
    • 30 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2001

    22855 White Swan Way, Leonardtown, MD 20650

    Move right in! Tucked away on 3.59 acres, everything has been upgraded. Main level offers stunning hardwood flooring throughout, great room with 2 story ceilings and walls of windows letting nature and light in. Formal living room with custom, built-in bar and formal dining make this an exceptional home for entertaining and large gatherings. Kitchen for the gourmet cook offers natural quartzite

    Barbara Stellway KW Metro Center

    22855 White Swan Way, Leonardtown, MD 20650
  • 21940 Maranatha Way, Leonardtown, MD 20650
    21940 Maranatha Way, Leonardtown, MD 20650
    21940 Maranatha Way, Leonardtown, MD 20650
    /55

    $925,000 Sold May 30, 2025

    • 2,814 Sq Ft
    • $329/SF
    • 23 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1993

    21940 Maranatha Way, Leonardtown, MD 20650

    Beautifully maintained and thoughtfully updated, this 3-bedroom, 2.5-bathroom rambler with a separate 1-bedroom, 1-bathroom apartment above the garage offers the perfect combination of comfort, style, and stunning waterfront living. Conveniently located on a private road, enjoy peaceful privacy while being just minutes from shops, dining, and all that Leonardtown has to offer.Inside the main

    Adam Chambers JPAR Real Estate Professionals

    21940 Maranatha Way, Leonardtown, MD 20650
  • 23687 Coventry Dr, Leonardtown, MD 20650
    23687 Coventry Dr, Leonardtown, MD 20650
    23687 Coventry Dr, Leonardtown, MD 20650
    /58

    $665,000 Sold May 30, 2025

    • 4,650 Sq Ft
    • $143/SF
    • 32 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2012

    23687 Coventry Dr, Leonardtown, MD 20650

    Significant Price Adjustment – Now Priced Below Market Value!Seize the opportunity to make this stunning, move-in-ready 6-bedroom, 4.5-bath home your own. Situated on a prime corner lot in the sought-after Leonard's Grant community, this home offers over 5,500 square feet of beautifully finished space designed for comfort, entertaining, and everyday living.Highlights include a Gourmet Kitchen

    Lesa Clark Redfin Corp

    23687 Coventry Dr, Leonardtown, MD 20650
  • 40449 Breton View Dr, Leonardtown, MD 20650
    40449 Breton View Dr, Leonardtown, MD 20650
    40449 Breton View Dr, Leonardtown, MD 20650
    /29

    $408,000 Sold May 23, 2025

    • 2,288 Sq Ft
    • $178/SF
    • 33 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1995

    40449 Breton View Dr, Leonardtown, MD 20650

    Experience the serene lifestyle of Breton Bay, where charm and convenience come together! Just steps away from the Breton Bay Country Club—offering pool, tennis, and golf amenities—and a short drive to the historic downtown Leonardtown for dining, shopping, and local events, this townhome is your ideal retreat.This captivating 3-level, three-bedroom, 3.5-bath townhome features vinyl flooring

    Edward Tully RE/MAX One

    40449 Breton View Dr, Leonardtown, MD 20650
  • 44195 Jessica Ln, Leonardtown, MD 20650
    44195 Jessica Ln, Leonardtown, MD 20650
    44195 Jessica Ln, Leonardtown, MD 20650
    /49

    $591,000 Sold May 22, 2025

    • 2,918 Sq Ft
    • $203/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    44195 Jessica Ln, Leonardtown, MD 20650

    Stunning Cape Cod on 3+ Acres in Leonardtown!Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial offering 2,918 sq ft of spacious living, nestled on 3.13 acres in the heart of Leonardtown. From the moment you arrive, you’ll feel the charm—this home stands out with its impressive curb appeal and serene setting.The wide, well-manicured driveway leads to a side-load garage, providing

    Mark Frisco CENTURY 21 New Millennium

    44195 Jessica Ln, Leonardtown, MD 20650
  • 41500 Margrove Cir, Leonardtown, MD 20650
    41500 Margrove Cir, Leonardtown, MD 20650
    41500 Margrove Cir, Leonardtown, MD 20650
    /73

    $435,000 Sold May 21, 2025

    • 2,306 Sq Ft
    • $189/SF
    • 3 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2019

    41500 Margrove Cir, Leonardtown, MD 20650

    Welcome home to this meticulously maintained Compton model townhome, with rear kitchen, in the sought after community of Clark's Rest. Nestled on a quiet street near the heart of Leonardtown, this home offers the tranquility and privacy you deserve after the hustle and bustle of a busy day. Luxury vinyl plank flooring flows throughout the main level, providing both continuity and style. The

    Robin Errington CENTURY 21 New Millennium

    41500 Margrove Cir, Leonardtown, MD 20650
  • 20483 White Point Rd, Leonardtown, MD 20650
    20483 White Point Rd, Leonardtown, MD 20650
    20483 White Point Rd, Leonardtown, MD 20650
    /22

    $300,000 Sold May 20, 2025

    • 1,160 Sq Ft
    • $259/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1953

    20483 White Point Rd, Leonardtown, MD 20650

    Welcome to 20483 White Point Road!Nestled on a beautiful 1-acre lot in Leonardtown, this charming 3-bedroom, 1-bath cottage-style rambler offers the perfect blend of comfort and character. Built in 1953, the home features a cozy, single-level layout that’s easy to maintain and full of potential. Enjoy peaceful country living surrounded by nature, all while being just a short drive to the heart of

    Theresa Shoptaw Redfin Corp

    20483 White Point Rd, Leonardtown, MD 20650
  • 41403 Heritage Ln, Leonardtown, MD 20650
    41403 Heritage Ln, Leonardtown, MD 20650
    41403 Heritage Ln, Leonardtown, MD 20650
    /53

    $605,000 Sold May 16, 2025

    • 3,340 Sq Ft
    • $181/SF
    • 6 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2016

    41403 Heritage Ln, Leonardtown, MD 20650

    This beautiful home, situated on a desirable corner lot, exudes warmth and timeless charm. Hardwood flooring greets you upon entry, complemented by crown molding, chair rail accents, and recessed wall niches, all adding to the home’s classic appeal.The formal dining room, highlighted by stately columns and a tray ceiling, provides a sophisticated space for gatherings. The island kitchen features

    Wanda White CENTURY 21 New Millennium

    41403 Heritage Ln, Leonardtown, MD 20650
  • 41434 Margrove Cir, Leonardtown, MD 20650
    41434 Margrove Cir, Leonardtown, MD 20650
    41434 Margrove Cir, Leonardtown, MD 20650
    /29

    $435,000 Sold May 16, 2025

    • 2,356 Sq Ft
    • $185/SF
    • 30 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2020

    41434 Margrove Cir, Leonardtown, MD 20650

    Stunning 3-Bedroom, 3.5-Bath Townhome in Clarks Rest, Leonardtown, MDWelcome to this beautiful and spacious 3-bedroom, 3.5-bath townhome nestled in the highly sought-after Clarks Rest neighborhood of Leonardtown, Maryland. With over 1,900, this meticulously maintained home offers a perfect blend of modern living and comfort. Step inside to discover a bright and open floor plan featuring a large

    Jonathan Boss RE/MAX One

    41434 Margrove Cir, Leonardtown, MD 20650
  • 41326 Margrove Cir, Leonardtown, MD 20650
    41326 Margrove Cir, Leonardtown, MD 20650
    41326 Margrove Cir, Leonardtown, MD 20650
    /77

    $485,000 Sold May 15, 2025

    • 2,645 Sq Ft
    • $183/SF
    • 0 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2015

    41326 Margrove Cir, Leonardtown, MD 20650

    Stop the Car—This Is the One!Welcome to this stunning and expansive 3,290 sq. ft. end-unit townhome that offers the perfect blend of elegance, comfort, and unbeatable location. From the moment you step inside, you’ll be captivated by the rich hardwood flooring on the main level and the abundance of natural light that pours in through the oversized end-unit windows.The heart of the home is the

    Jessica Raley CENTURY 21 New Millennium

    41326 Margrove Cir, Leonardtown, MD 20650
  • 23259 Jenifer Ct, Leonardtown, MD 20650
    23259 Jenifer Ct, Leonardtown, MD 20650
    23259 Jenifer Ct, Leonardtown, MD 20650
    /80

    $655,000 Sold May 15, 2025

    • 4,078 Sq Ft
    • $161/SF
    • 6 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2005

    23259 Jenifer Ct, Leonardtown, MD 20650

    DRIVE BY AT NIGHT TO SEE ALL THE EXTERIOR LIGHTING AROUND THE HOME. Stunning 5BR/3.5BA colonial with stone accents and two-car garage located in Estates at Singletree. This model features an open floor plan spanning approximately 4,000 square feet on three levels and offers a great sense of light and spaciousness with 9-foot. ceilings and floor-to-ceiling windows on the main level. Designer décor

    Michael Rose Rory S. Coakley Realty, Inc.

    23259 Jenifer Ct, Leonardtown, MD 20650
  • 42921 Hungerford Ct, Hollywood, MD 20636
    42921 Hungerford Ct, Hollywood, MD 20636
    42921 Hungerford Ct, Hollywood, MD 20636
    /47

    $745,000 Sold May 15, 2025

    • 3,929 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    42921 Hungerford Ct, Hollywood, MD 20636

    Stunning Colonial Home on 2.7 AcresThis beautifully maintained Colonial home sits on a private 2.7-acre lot at the end of a cul-de-sac, offering both seclusion and easy access to trails in the woods. The main level features an open kitchen and family room with a gas fireplace. Hardwood floors throughout including living and dining areas. Enjoy entertaining in the 20x20 heated screened porch,

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    42921 Hungerford Ct, Hollywood, MD 20636
  • 23598 Belmar Dr, Leonardtown, MD 20650
    23598 Belmar Dr, Leonardtown, MD 20650
    23598 Belmar Dr, Leonardtown, MD 20650
    /10

    $660,000 Sold May 15, 2025

    • 3,758 Sq Ft
    • $176/SF
    • 16 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2010

    23598 Belmar Dr, Leonardtown, MD 20650

    Welcome to this beautifully upgraded 5-bedroom, 3.5-bathroom home, perfectly situated on one of the best lots in the neighborhood! Backing to trees for added privacy, this home offers both elegance and functionality.Step inside to find refinished hardwood floors throughout the main level, adding warmth and sophistication. The gourmet kitchen features sleek quartz countertops, a new backsplash,

    Heather Foster RE/MAX One

    23598 Belmar Dr, Leonardtown, MD 20650
  • 20235 Big Oak Ln, Leonardtown, MD 20650
    20235 Big Oak Ln, Leonardtown, MD 20650
    20235 Big Oak Ln, Leonardtown, MD 20650
    /23

    $295,000 Sold May 14, 2025

    • 1,036 Sq Ft
    • $285/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1934

    20235 Big Oak Ln, Leonardtown, MD 20650

    Water access home with 3 bedrooms and 1 bath with laundry closet. Laminate flooring for easy of cleaning and pet friendly throughout much of the home. Level yard with big shed in back with 2 sides to store kayaks or other fun equipment for warm weather use. Patio in back and large clear side yard for volleyball or bocce ball or even corn hole. Make your plans now to come and see and make it your

    Jan Kleponis O'Brien Realty ERA Powered

    20235 Big Oak Ln, Leonardtown, MD 20650
  • 22158 Monterey Place, Leonardtown, MD 20650
    22158 Monterey Place, Leonardtown, MD 20650
    22158 Monterey Place, Leonardtown, MD 20650
    /56

    $500,000 Sold May 09, 2025

    • 1,782 Sq Ft
    • $281/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    22158 Monterey Place, Leonardtown, MD 20650

    Rarely do you have this kind of water view from every room in the home. Enjoy waking to vacation type views everyday....This home has a unique design that affords itself to many buyers. Pride of ownership abounds. Many recent improvements, including windows and doors. Roof replaced approx. 5 years ago. Home shows very well. Come see this home quickly so you can make this your new home.

    C. Brandon Harrington PAX Real Estate

    22158 Monterey Place, Leonardtown, MD 20650
  • 21620 Coves End Ct, Leonardtown, MD 20650
    21620 Coves End Ct, Leonardtown, MD 20650
    21620 Coves End Ct, Leonardtown, MD 20650
    /67

    $691,000 Sold May 09, 2025

    • 3,541 Sq Ft
    • $195/SF
    • 33 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    21620 Coves End Ct, Leonardtown, MD 20650

    ASSUMABLE RATE MORTGAGE AVAILABLE AT 2.5%. Don't miss your chance to own property in the highly desirable Breton Bay Golf Community of Leonardtown. Here you'll enjoy stunning views of the beautiful golf course and the perks of living in a waterfront community with a nearby marina and access to a private beach area of the Bay! Situated on a small, quiet cul-de-sac street located directly across

    Hannah Cole Real Broker, LLC

    21620 Coves End Ct, Leonardtown, MD 20650
  • 42500 Saint Margarets Dr, Leonardtown, MD 20650
    42500 Saint Margarets Dr, Leonardtown, MD 20650
    42500 Saint Margarets Dr, Leonardtown, MD 20650
    /12

    $135,000 Sold May 09, 2025

    • Land
    • 4.8 Acres
    • $28,125 per Acre
    • 76 Days On Market

    42500 Saint Margarets Dr, Leonardtown, MD 20650

    Expansive 4.8-Acre lot in highly sought after location.RECORDED PERC! Ready to build! Located just minutes outside the heart of Leonardtown, MD, this beautiful 4.8-acre lot offers a rare opportunity to bring your dream home to life on almost 5 private acres. Please be advised lot lines drawn on listing photo are not exact; just approximate and for visual purposes only.

    Kalee Kelly Infinitas Realty Group

    42500 Saint Margarets Dr, Leonardtown, MD 20650
  • 41442 Dauber Way, Leonardtown, MD 20650
    41442 Dauber Way, Leonardtown, MD 20650
    41442 Dauber Way, Leonardtown, MD 20650
    /50

    $610,000 Sold May 08, 2025

    • 3,558 Sq Ft
    • $171/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2013

    41442 Dauber Way, Leonardtown, MD 20650

    Don’t miss this fantastic find in Leonard's Grant! This bright and airy home features an open floor plan, soaring ceilings, and abundant natural light. The spacious family room flows seamlessly into the kitchen and main living areas, creating an inviting space for everyday living.Upstairs, you’ll find three well-sized bedrooms and convenient bedroom-level laundry. The primary suite offers high

    Lesa Clark Redfin Corp

    41442 Dauber Way, Leonardtown, MD 20650
  • 21500 Point Lookout Rd, Callaway, MD 20620
    21500 Point Lookout Rd, Callaway, MD 20620
    21500 Point Lookout Rd, Callaway, MD 20620
    /97

    $600,000 Sold May 06, 2025

    • 3,605 Sq Ft
    • $166/SF
    • 253 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1955

    21500 Point Lookout Rd, Callaway, MD 20620

    All-Brick Rambler on a 6.11 acre lot along with a 9.58 acre separate lot with potential for additional homesite. This price includes both lots Welcome to 21500 Point Lookout Road, Leonardtown! This all-brick rambler sits on a large extensively landscaped lot and offers over 3,600 sq. ft. on the main level, plus 1,200 sq. ft. in the partially finished lower level. The home features 3 bedrooms

    Jennifer Goddard CENTURY 21 New Millennium

    21500 Point Lookout Rd, Callaway, MD 20620
  • 40222 Breton Beach Rd, Leonardtown, MD 20650
    40222 Breton Beach Rd, Leonardtown, MD 20650
    40222 Breton Beach Rd, Leonardtown, MD 20650
    /37

    $540,000 Sold Apr 30, 2025

    • 1,296 Sq Ft
    • $417/SF
    • 207 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1976

    40222 Breton Beach Rd, Leonardtown, MD 20650

    This dreamy waterfront getaway is the perfect spot for you to fully unwind and relax. Located directly along Breton Bay, you'll enjoy peace and serenity while only being a short 10 minute drive from downtown Leonardtown, or take a short boat ride across the bay to Fitzies for drinks and dinner. This charming cape cod offers amazing sunsets whether it's from the scenic deck, screened in porch or

    Jake Grier Baldus Real Estate, Inc.

    40222 Breton Beach Rd, Leonardtown, MD 20650
  • 23267 Clarks Rest Rd, Leonardtown, MD 20650
    23267 Clarks Rest Rd, Leonardtown, MD 20650
    23267 Clarks Rest Rd, Leonardtown, MD 20650
    /66

    $700,000 Sold Apr 25, 2025

    • 5,213 Sq Ft
    • $134/SF
    • 3 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 2015

    23267 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this impressive and elegant 5-bedroom, 4 full and 2 half-bath home, offering the perfect blend of luxury, comfort, and energy efficiency. Located in a highly desirable community with walking sidewalks, a community center, playgrounds, and a sparkling pool, this property provides an exceptional lifestyle. Plus, it's only a convenient trolley ride away from downtown Leonardtown, where

    Chris Hill CENTURY 21 New Millennium

    23267 Clarks Rest Rd, Leonardtown, MD 20650
  • 23749 Coventry Dr, Leonardtown, MD 20650
    23749 Coventry Dr, Leonardtown, MD 20650
    23749 Coventry Dr, Leonardtown, MD 20650
    /64

    $739,900 Sold Apr 25, 2025

    • 6,015 Sq Ft
    • $123/SF
    • 179 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2013

    23749 Coventry Dr, Leonardtown, MD 20650

    This exceptional home is designed with luxury and space in mind, featuring expansive rooms thanks to bump-outs on two sides. The main level is an entertainer's dream, boasting an open floor plan that seamlessly connects the gourmet kitchen, breakfast room, family room, dining area, and sunroom. A library or office adds a touch of versatility. Hardwood floors run throughout the first two levels,

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23749 Coventry Dr, Leonardtown, MD 20650
  • 41443 Whimsical Ct, Leonardtown, MD 20650
    41443 Whimsical Ct, Leonardtown, MD 20650
    41443 Whimsical Ct, Leonardtown, MD 20650
    /4

    $645,000 Sold Apr 22, 2025

    • 3,400 Sq Ft
    • $190/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2010

    41443 Whimsical Ct, Leonardtown, MD 20650

    Welcome to this beautifully updated 5-bedroom, 3.5-bath Colonial home, offering the perfect blend of modern updates and classic charm. Step inside to find refinished hardwood floors, fresh paint, and new carpet throughout, creating a bright and inviting atmosphere.The heart of the home extends outdoors, where you'll discover a serene, tree-lined backyard with an incredible outdoor living space.

    Heather Foster RE/MAX One

    41443 Whimsical Ct, Leonardtown, MD 20650
  • 22925 Downs Cir, Leonardtown, MD 20650
    22925 Downs Cir, Leonardtown, MD 20650
    22925 Downs Cir, Leonardtown, MD 20650
    /38

    $387,000 Sold Apr 21, 2025

    • 1,904 Sq Ft
    • $203/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1977

    22925 Downs Cir, Leonardtown, MD 20650

    Convenient, central location walkable to downtown Leonardtown! Tucked away on a quiet cul-de-sac, this house was beautifully renovated. ! Enjoy evenings on the generously oversized deck with pergola. Huge yard backs to trees. Great use of space throughout - master features walk-in closet and full master bath, finished basement offers lots of extra room!

    Ross Simone RE/MAX Realty Group

    22925 Downs Cir, Leonardtown, MD 20650
  • 20503 Deer Wood Park Dr, Leonardtown, MD 20650
    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    /117

    $725,000 Sold Apr 17, 2025

    • 5,862 Sq Ft
    • $124/SF
    • 19 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1997

    20503 Deer Wood Park Dr, Leonardtown, MD 20650

    Discover this expansive, custom-designed brick Colonial situated on 2 pristine acres in the highly sought-after Chestnut Hills subdivision. Meticulously maintained, this stunning home offers a grand 2-story foyer and a soaring family room with a cozy propane fireplace, all complemented by 9-foot ceilings throughout the main level.The open-concept kitchen is a chef’s dream, featuring a center

    Tracey Summers CENTURY 21 New Millennium

    20503 Deer Wood Park Dr, Leonardtown, MD 20650
  • 19710 Tower Hill Rd, Leonardtown, MD 20650
    19710 Tower Hill Rd, Leonardtown, MD 20650
    19710 Tower Hill Rd, Leonardtown, MD 20650
    /3

    $1,225,000 Sold Mar 31, 2025

    • 5,690 Sq Ft
    • $215/SF
    • 5 Beds
    • 6.5 Baths
    • Built 1984

    19710 Tower Hill Rd, Leonardtown, MD 20650

    Private 3.31 acre lot with beautiful views across the Potomac River. Home is almost 6000 square feet with close to 200 feet of rip rapped water frontage. 6 bedrooms and 5.5 baths including a private in law suite. Main level formal living room with doors leading to sunroom, formal dining room, private office with custom built ins, large family room off kitchen with wood burning fireplace and

    Jennifer Goddard CENTURY 21 New Millennium

    19710 Tower Hill Rd, Leonardtown, MD 20650
  • 43012 Bluejay Ln, Leonardtown, MD 20650
    43012 Bluejay Ln, Leonardtown, MD 20650
    43012 Bluejay Ln, Leonardtown, MD 20650
    /9

    $740,500 Sold Mar 27, 2025

    • 3,440 Sq Ft
    • $215/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2021

    43012 Bluejay Ln, Leonardtown, MD 20650

    Come visit this lovely Fairfax model home in the desirable community of The Meadows at Town Run. Built in 2021 by Quality Built Homes, this beauty will not disappoint. Nestled on a corner lot at the end of a quiet cul-de-sac and backing to trees add to the charm and privacy of this immaculately kept beauty. Inside the home you will find well thought-out appointments, to include 5 bedrooms and

    Robin Errington CENTURY 21 New Millennium

    43012 Bluejay Ln, Leonardtown, MD 20650
  • 42297 Riverwinds Dr, Leonardtown, MD 20650
    42297 Riverwinds Dr, Leonardtown, MD 20650
    42297 Riverwinds Dr, Leonardtown, MD 20650
    /56

    $1,450,000 Sold Mar 26, 2025

    • 3,709 Sq Ft
    • $391/SF
    • 4 Days On Market
    • 4 Beds
    • 7 Baths
    • Built 1983

    42297 Riverwinds Dr, Leonardtown, MD 20650

    Custom waterfront home on the Potomac River with breathtaking panoramic views. Designed for both family living and entertaining, this spacious residence boasts a thoughtfully remodeled gourmet kitchen by St. Maries Builders, a family room, sunroom, living room, and a large den with a full bath on the main level. Expansive windows maximize natural light and showcase stunning sunsets.The

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    42297 Riverwinds Dr, Leonardtown, MD 20650
  • 22380 White Oak Rd, Leonardtown, MD 20650
    22380 White Oak Rd, Leonardtown, MD 20650
    22380 White Oak Rd, Leonardtown, MD 20650
    /53

    $442,500 Sold Mar 25, 2025

    • 2,680 Sq Ft
    • $165/SF
    • 30 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1975

    22380 White Oak Rd, Leonardtown, MD 20650

    Welcome to your dream home in the highly sought-after Breton Bay community of Leonardtown, Maryland! This property is a true standout, with major repairs and thoughtful upgrades already done to provide ultimate comfort and peace of mind. At the top of the list are a brand-new septic system and a new roof, alongside a host of enhancements including a fenced rear yard, leaf guards, a new roof on

    Diana Washabaugh CENTURY 21 New Millennium

    22380 White Oak Rd, Leonardtown, MD 20650
  • 41482 Margrove Cir, Leonardtown, MD 20650
    41482 Margrove Cir, Leonardtown, MD 20650
    41482 Margrove Cir, Leonardtown, MD 20650
    /4

    $483,000 Sold Mar 24, 2025

    • 2,645 Sq Ft
    • $183/SF
    • 4 Beds
    • 3.5 Baths
    • Built 2019

    41482 Margrove Cir, Leonardtown, MD 20650

    This home is the perfect choice in Clarks Rest! It features the expansive Callaway floor plan and offers a beautiful pond view. This end-unit townhome includes a 2-car rear-load garage, gas heating, a tankless water heater, and gas cooking. With 4 bedrooms and 3.5 baths, you will enjoy granite countertops in the kitchen, stainless steel appliances, and upgraded cabinetry. The spacious living area

    Chris Norris JR. Topside Realty

    41482 Margrove Cir, Leonardtown, MD 20650
  • 22239 Point Lookout Rd, Leonardtown, MD 20650
    22239 Point Lookout Rd, Leonardtown, MD 20650
    22239 Point Lookout Rd, Leonardtown, MD 20650
    /23

    $285,000 Sold Mar 20, 2025

    • 1,669 Sq Ft
    • $171/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1966

    22239 Point Lookout Rd, Leonardtown, MD 20650

    Such a convenient location. Minutes from downtown Leonardtown, minutes from NAS Patuxent River. This property is has lots of space and a garage that offers so much. Relax on your front porch or back deck. High ceiling with skylights in super big family room. Primary bedroom exists to large rear deck. Garage has work space and air lines already in place. Oil heat keeps you warm on cold

    John Gatton CENTURY 21 New Millennium

    22239 Point Lookout Rd, Leonardtown, MD 20650
  • 21717 Meadow Ct, Leonardtown, MD 20650
    21717 Meadow Ct, Leonardtown, MD 20650
    21717 Meadow Ct, Leonardtown, MD 20650
    /41

    $449,900 Sold Mar 14, 2025

    • 1,488 Sq Ft
    • $302/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1981

    21717 Meadow Ct, Leonardtown, MD 20650

    Custom passive solar home designed for energy efficiency and comfort. This thoughtfully updated home features a newly remodeled kitchen with new cabinets, countertops, and appliances, plus LVT flooring throughout. The primary and half baths have been completely renovated.An open floor plan enhances natural light, with a solarium featuring a tiled floor. Additional highlights include a

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    21717 Meadow Ct, Leonardtown, MD 20650

Showing Results 41 - 80, Page 2 of 5

Maryland St Marys County Leonardtown 20650

Recently Sold Real Estate & Homes in 20650

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