6,717

Leonardtown, MD Homes

Section Image
  • Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
    /46

    $447,400 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650

    ***MOVE IN READY***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 88 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison D2,

    Laura Bernth RE/MAX One

    Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650
  • 43840 Tarrywyle Way, Leonardtown, MD 20650
    43840 Tarrywyle Way, Leonardtown, MD 20650
    43840 Tarrywyle Way, Leonardtown, MD 20650
    /42

    $5,000 per month

    • 6 Beds
    • 5 Baths
    • 5,278 Sq Ft
    • House for Rent

    43840 Tarrywyle Way, Leonardtown, MD 20650

    Tatiana Bell Quasar Property Management And Real Estate LLC

    43840 Tarrywyle Way, Leonardtown, MD 20650
  • 41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    41130 Cryer Ct, Leonardtown, MD 20650
    /15

    $485,000 Sold Nov 14, 2025

    • 1,488 Sq Ft
    • $326/SF
    • 115 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    41130 Cryer Ct, Leonardtown, MD 20650

    This property is back on the market. This is your gain. A rare opportunity on the shores of Breton Bay, presents a canvas for transformation. This expansive 1.05 acre waterfront boast 164 feet of private shoreline and delivers breathtaking sunset panoramas. This classic 1955 construction offers endless renovation potential. With 1468 square feet of main living space and a 1247 square foot

    Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, Leonardtown, MD 20650
    • 41408 W Citation St, Leonardtown, MD 20650
      41408 W Citation St, Leonardtown, MD 20650
      41408 W Citation St, Leonardtown, MD 20650
      /87

      Est $749,844 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,960 Sq Ft

      41408 W Citation St, Leonardtown, MD 20650

      41408 W Citation St, Leonardtown, MD 20650
  • 25895 Point Lookout Rd, Leonardtown, MD 20650
    25895 Point Lookout Rd, Leonardtown, MD 20650
    25895 Point Lookout Rd, Leonardtown, MD 20650
    /20

    $249,000

    • Land
    • 1 Acre
    • $249,000 per Acre

    25895 Point Lookout Rd, Leonardtown, MD 20650

    Position your business for success with this 1.00-acre commercial lot in Leonardtown, MD, zoned Commercial Highway (C-H). Located next to PNC Bank and across from a storage facility, this property boasts great visibility and easy access, making it ideal for a variety of commercial uses.Zoning allows for flexible development options such as: Retail and Business Establishments

    Krista Depenthal Lands2Love

    25895 Point Lookout Rd, Leonardtown, MD 20650
  • 41650 Matthew Ct, Leonardtown, MD 20650
    41650 Matthew Ct, Leonardtown, MD 20650
    41650 Matthew Ct, Leonardtown, MD 20650
    /15

    $475,000 Sold Nov 14, 2025

    • 2,230 Sq Ft
    • $213/SF
    • 47 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    41650 Matthew Ct, Leonardtown, MD 20650

    This home features 4 spacious Bedrooms, an open Kitchen & great room w/built-in TV Niche over the gas Fireplace. There is a full basement w/rough-in. A Walk-in jetted tub and electric stair chair have been added. The property has a large, level fenced back yard with raised garden beds and is at the end of a cul-de-sac! The back deck provides space for cooking out and private entertaining. Located

    Paula Turner Pax River Realty LLC

    41650 Matthew Ct, Leonardtown, MD 20650
    • 22765 Duke St, Leonardtown, MD 20650
      22765 Duke St, Leonardtown, MD 20650
      22765 Duke St, Leonardtown, MD 20650
      /10

      Est $267,093 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 862 Sq Ft

      22765 Duke St, Leonardtown, MD 20650

      22765 Duke St, Leonardtown, MD 20650
  • 23581 Gallent Fox Way, Leonardtown, MD 20650
    23581 Gallent Fox Way, Leonardtown, MD 20650
    23581 Gallent Fox Way, Leonardtown, MD 20650
    /53

    $645,900 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft

    23581 Gallent Fox Way, Leonardtown, MD 20650

    Welcome to 23581 Gallent Fox Way, a beautifully maintained and thoughtfully upgraded home nestled in the heart of highly desirable Leonard’s Grant. Situated in one of Leonardtown’s most sought-after communities, this 4-bedroom, 3.5-bath 3,933 sq ft residence combines comfort, convenience, and a true sense of community living. Perfectly positioned directly across from the community pool and

    Laura Bernth RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
  • 23242 Clarks Rest Rd, Leonardtown, MD 20650
    23242 Clarks Rest Rd, Leonardtown, MD 20650
    23242 Clarks Rest Rd, Leonardtown, MD 20650
    /52

    $589,000 Sold Nov 03, 2025

    • 3,296 Sq Ft
    • $179/SF
    • 69 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2017

    23242 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Clark’s Rest community of Leonardtown! Boasting nearly 3,300 square feet with an open floor plan filled with natural light, this home offers a perfect blend of comfort and functionality. The main level features spacious living and dining areas that flow effortlessly into a modern kitchen—ideal for

    Matthew Burgan Infinitas Realty Group

    23242 Clarks Rest Rd, Leonardtown, MD 20650
    • 20102 Whippoorwill Ln, Leonardtown, MD 20650
      20102 Whippoorwill Ln, Leonardtown, MD 20650
      20102 Whippoorwill Ln, Leonardtown, MD 20650
      /76

      Est $726,674 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,785 Sq Ft

      20102 Whippoorwill Ln, Leonardtown, MD 20650

      20102 Whippoorwill Ln, Leonardtown, MD 20650
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /79

    $639,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality.The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your

    Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • 23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    /25

    $402,000 Sold Oct 31, 2025

    • 1,992 Sq Ft
    • $202/SF
    • 49 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    23730 Hicks Dr, Leonardtown, MD 20650

    Back on market at a new price — the buyer’s loss is your gain! This is one of only five single-family homes in Leonardtown currently listed under $500,000 — and it’s move-in ready with major updates already done. Renovated just 3 years ago, this charming 3-bedroom, 2-bath rambler sits on a spacious half-acre lot with a walk-out basement and no HOA, giving you flexibility to bring your vision to

    Kimberlee Randall Group EXP Realty, LLC

    23730 Hicks Dr, Leonardtown, MD 20650
    • 28845 Point Lookout Rd, Leonardtown, MD 20650
      28845 Point Lookout Rd, Leonardtown, MD 20650
      28845 Point Lookout Rd, Leonardtown, MD 20650
      /20

      Est $362,061 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,520 Sq Ft

      28845 Point Lookout Rd, Leonardtown, MD 20650

      28845 Point Lookout Rd, Leonardtown, MD 20650
  • 41492 Charismatic Way, Leonardtown, MD 20650
    41492 Charismatic Way, Leonardtown, MD 20650
    41492 Charismatic Way, Leonardtown, MD 20650
    /49

    $639,900

    • 4 Beds
    • 3.5 Baths
    • 3,322 Sq Ft

    41492 Charismatic Way, Leonardtown, MD 20650

    Welcome home to 41492 Charismatic Way, the stunning Fenwick model by Quality Built Homes in the highly sought-after Leonard’s Grant community in Leonardtown! With 4 spacious bedrooms, 3.5 baths, and nearly 4,000 finished sq ft, this well-appointed home blends elevated design, thoughtful functionality, and timeless comfort in every detail. A welcoming foyer opens to formal living and dining rooms,

    Laura Bernth RE/MAX One

    41492 Charismatic Way, Leonardtown, MD 20650
  • 41474 Charismatic Way, Leonardtown, MD 20650
    41474 Charismatic Way, Leonardtown, MD 20650
    41474 Charismatic Way, Leonardtown, MD 20650
    /79

    $639,000 Sold Oct 30, 2025

    • 3,647 Sq Ft
    • $175/SF
    • 57 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2015

    41474 Charismatic Way, Leonardtown, MD 20650

    Welcome to 41474 Charismatic Way in the highly sought-after Leonard’s Grant community of Leonardtown, Maryland. This beautifully maintained 5-bedroom, 3.5-bath home offers over 3,600 square feet of finished living space and combines elegance, comfort, and function in every detail. From the charming large front porch to the professionally landscaped yard, the curb appeal is undeniable. Step inside

    Laura Bernth RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
    • 23920 Susies Ln, Leonardtown, MD 20650
      23920 Susies Ln, Leonardtown, MD 20650
      23920 Susies Ln, Leonardtown, MD 20650
      /7

      Est $192,066 Not Listed For Sale

      23920 Susies Ln, Leonardtown, MD 20650

      23920 Susies Ln, Leonardtown, MD 20650
  • 23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    /59

    $599,000

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    PRICE IMPROVEMENT! **Custom Floorplan** Front Load Garage with expanded guest parking on driveway, upgraded cabinets, Countertops, and custom Primary suite walk in frameless glass shower. Built on an oversized premium corner lot with extra large fenced backyard. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • 20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    20919 Ridge Path Way, Leonardtown, MD 20650
    /56

    $549,000 Sold Oct 30, 2025

    • 3,465 Sq Ft
    • $158/SF
    • 69 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1992

    20919 Ridge Path Way, Leonardtown, MD 20650

    Nestled on a serene and private 3.29-acre lot—plus an additional 0.5-acre parcel—20919 Ridge Path Way offers the perfect balance of seclusion and convenience in the heart of Leonardtown. This professionally upgraded 4-bedroom, 3.5-bath home delivers both peace of mind and high-end comfort with all major systems and appliances less than 5 years old. Step inside and experience a beautifully

    Matthew Burgan Infinitas Realty Group

    20919 Ridge Path Way, Leonardtown, MD 20650
    • 19661 Hickory Hills Ln, Leonardtown, MD 20650
      19661 Hickory Hills Ln, Leonardtown, MD 20650
      19661 Hickory Hills Ln, Leonardtown, MD 20650
      /76

      Est $562,290 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,342 Sq Ft

      19661 Hickory Hills Ln, Leonardtown, MD 20650

      19661 Hickory Hills Ln, Leonardtown, MD 20650
  • 43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    /66

    $655,000

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    43018 Bluejay Ln, Leonardtown, MD 20650

    Beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite features a large

    Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
  • 20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    /41

    $599,900 Sold Oct 30, 2025

    • 3,061 Sq Ft
    • $196/SF
    • 94 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1995

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    Welcome to this well-built colonial on a corner lot in the picturesque corner Chestnut Ridge neighborhood! With over 3,000 finished square feet, 5 bedrooms, and 3.5 bathrooms, this home is full of charm, character, and thoughtful craftsmanship. Situated on 2.11 acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the main level,

    Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    • 18822 McKays Beach Rd, Leonardtown, MD 20650
      18822 McKays Beach Rd, Leonardtown, MD 20650
      18822 McKays Beach Rd, Leonardtown, MD 20650
      /79

      Est $670,118 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,962 Sq Ft

      18822 McKays Beach Rd, Leonardtown, MD 20650

      18822 McKays Beach Rd, Leonardtown, MD 20650
  • 21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    21117 Catnip Ct, Leonardtown, MD 20650
    /49

    $610,000

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft

    21117 Catnip Ct, Leonardtown, MD 20650

    Seller is offering a $4,000 concession with an accepted full-price offer!Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees and plenty of

    Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • 41900 Nazareth Ct, Leonardtown, MD 20650
    41900 Nazareth Ct, Leonardtown, MD 20650
    41900 Nazareth Ct, Leonardtown, MD 20650
    /26

    $460,000 Sold Oct 29, 2025

    • 2,528 Sq Ft
    • $182/SF
    • 76 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    41900 Nazareth Ct, Leonardtown, MD 20650

    Welcome to the Academy Hills of Leonardtown. The main level features a traditional floor plan, recent upgrades including new carpet August 2025, stainless steel kitchen appliances, plenty of cabinet space, a formal dining room, and a convenient powder room. Major system updates include a brand-new Roof and a new HVAC system for added peace of mind.Upstairs, newly installed banisters, the

    Marizel Brewington RE/MAX One

    41900 Nazareth Ct, Leonardtown, MD 20650
    • 41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      41419 Whimsical Ct, Leonardtown, MD 20650
      /39

      Est $626,321 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,993 Sq Ft

      41419 Whimsical Ct, Leonardtown, MD 20650

      41419 Whimsical Ct, Leonardtown, MD 20650
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /32

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    Are you dreaming of living on the water? This is your perfect opportunity! Well maintained rambler featuring waterfront, shared pier with boatlift, sunroom, 2-car attached garage, 1-car detached garage, 2-car carport. Gorgeous back yard, perfect for entertaining and spending those summer nights with friends and family. Get on your boat whenever the mood strikes you. This is the perfect home to

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • 20413 Scarlet Tanager Way, Leonardtown, MD 20650
    20413 Scarlet Tanager Way, Leonardtown, MD 20650
    20413 Scarlet Tanager Way, Leonardtown, MD 20650
    /34

    $575,000 Sold Oct 29, 2025

    • 3,094 Sq Ft
    • $186/SF
    • 1 Day On Market
    • 4 Beds
    • 3 Baths
    • Built 1990

    20413 Scarlet Tanager Way, Leonardtown, MD 20650

    Spacious 4-Bedroom, 3-Bath Home on Private 7-Acre Setting! Welcome to your peaceful retreat! This home sits on a secluded 7-acre lot and offers room to relax, entertain, and enjoy nature.Inside, the living room features an arched ceiling, while the remodeled kitchen (2013) has granite countertops and new stainless steel appliances (2024). The cozy family room includes a fireplace with wood

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    20413 Scarlet Tanager Way, Leonardtown, MD 20650
    • 41474 Affirmed Way, Leonardtown, MD 20650
      41474 Affirmed Way, Leonardtown, MD 20650
      41474 Affirmed Way, Leonardtown, MD 20650
      /76

      Est $650,613 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,050 Sq Ft

      41474 Affirmed Way, Leonardtown, MD 20650

      41474 Affirmed Way, Leonardtown, MD 20650
  • 41810 Chelsey Faye Ln, Leonardtown, MD 20650
    41810 Chelsey Faye Ln, Leonardtown, MD 20650
    41810 Chelsey Faye Ln, Leonardtown, MD 20650
    /7

    $720,000 New Construction

    • 4 Beds
    • 4 Baths
    • 2,650 Sq Ft

    41810 Chelsey Faye Ln, Leonardtown, MD 20650

    Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom Creations. Building a custom home allows you to choose between the standard home on a crawl space or opt for a basement foundation for an additional cost, giving you the opportunity to personalize this beautiful dwelling to your exact needs. If there is some other

    Jessica Ascenzo JPAR Real Estate Professionals

    41810 Chelsey Faye Ln, Leonardtown, MD 20650
  • 23745 Bayside Rd, Leonardtown, MD 20650
    23745 Bayside Rd, Leonardtown, MD 20650
    23745 Bayside Rd, Leonardtown, MD 20650
    /36

    $415,000 Sold Oct 24, 2025

    • 1,344 Sq Ft
    • $309/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1975

    23745 Bayside Rd, Leonardtown, MD 20650

    *Offer Deadline for Friday, September 12th, no later than 6PM.* Privacy, peace and pristine are all words that describe 23745 Bayside Road. This three bedroom, two bath rambler has been fully updated with today's modern finishes and custom features like wood pantry shelving & other great features, giving you style in every room. Nestled on one acre of extremely private land with a long winding

    Delaney Burgess RE/MAX United Real Estate

    23745 Bayside Rd, Leonardtown, MD 20650
    • 23546 Belmar Dr, Leonardtown, MD 20650
      23546 Belmar Dr, Leonardtown, MD 20650
      23546 Belmar Dr, Leonardtown, MD 20650
      /74

      Est $622,193 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,548 Sq Ft

      23546 Belmar Dr, Leonardtown, MD 20650

      23546 Belmar Dr, Leonardtown, MD 20650
  • 39825 Sweetpea Ln, Leonardtown, MD 20650
    39825 Sweetpea Ln, Leonardtown, MD 20650
    39825 Sweetpea Ln, Leonardtown, MD 20650
    /80

    $730,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft

    39825 Sweetpea Ln, Leonardtown, MD 20650

    Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 feet of water frontage, this 4-bedroom, 3.5-bath home offers peace, privacy, and panoramic views. Inside, you'll find 2,408 square feet of comfortable living space featuring a cozy fireplace, wood stove, and large windows that invite the beauty of the outdoors in. The expansive deck is perfect for entertaining

    Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • 41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    /53

    $680,000 Sold Oct 24, 2025

    • 3,825 Sq Ft
    • $178/SF
    • 32 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2010

    41480 Whimsical Ct, Leonardtown, MD 20650

    Welcome home to this stunning and spacious colonial in sought after Leonards Grant. This home enjoys over 3,800 square feet and is situated on .46 acre at the end of the cul-de-sac making it a private oasis. Upon entering, you're greeted by a two story foyer that is filled with natural sunlight. You'll instantly notice the pristine hard wood floors that flow throughout the home, along with the

    Fran Slade Compass

    41480 Whimsical Ct, Leonardtown, MD 20650
    • 41429 Challedon Way, Leonardtown, MD 20650
      41429 Challedon Way, Leonardtown, MD 20650
      41429 Challedon Way, Leonardtown, MD 20650
      /60

      Est $676,283 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,660 Sq Ft

      41429 Challedon Way, Leonardtown, MD 20650

      41429 Challedon Way, Leonardtown, MD 20650
  • 23261 Jenifer Ct, Leonardtown, MD 20650
    23261 Jenifer Ct, Leonardtown, MD 20650
    23261 Jenifer Ct, Leonardtown, MD 20650
    /42

    $580,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,575 Sq Ft

    23261 Jenifer Ct, Leonardtown, MD 20650

    This Colonial in the sought-after Estates at Singletree offers 5 bedrooms, 3.5 baths, and three finished levels in one of Leonardtown’s most convenient locations are just behind St. Mary’s Hospital. The fully finished basement is a highlight, featuring a home theater room, a rec room, a large bedroom with a walk-in closet, and a full bath. Upstairs, you will find four additional bedrooms,

    Gabriela Montgomery RE/MAX Realty Group

    23261 Jenifer Ct, Leonardtown, MD 20650
  • 21056 Woodmere Dr, Leonardtown, MD 20650
    21056 Woodmere Dr, Leonardtown, MD 20650
    21056 Woodmere Dr, Leonardtown, MD 20650
    /56

    $500,000 Sold Oct 23, 2025

    • 2,205 Sq Ft
    • $227/SF
    • 108 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    21056 Woodmere Dr, Leonardtown, MD 20650

    Nice Colonial with Covered Front Porch with concrete, Brick paver sidewalk and step, front load two car garage with exterior door to back yard. Storm Front Door with Side lights, Formal Living Room with Crown Molding, Dining Room Crown and Chair Molding, Hardwood Flooring in Foyer, Hall and Powder Room. Nice Kitchen with Center Island granite countertops, ceramic backsplash, Ceiling Light, New

    Kathryn Mausen Coldwell Banker Premier

    21056 Woodmere Dr, Leonardtown, MD 20650
    • 41895 Tomey Ct, Leonardtown, MD 20650
      41895 Tomey Ct, Leonardtown, MD 20650
      41895 Tomey Ct, Leonardtown, MD 20650
      /83

      Est $541,274 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,192 Sq Ft

      41895 Tomey Ct, Leonardtown, MD 20650

      41895 Tomey Ct, Leonardtown, MD 20650
  • Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
    Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
    Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650
    /43

    $469,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 93-23706 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 93 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 93-23706 Dragonfly Ln, Leonardtown, MD 20650
  • 20814 Deer Wood Park Dr, Leonardtown, MD 20650
    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    /53

    $560,000 Sold Oct 23, 2025

    • 3,412 Sq Ft
    • $164/SF
    • 22 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1996

    20814 Deer Wood Park Dr, Leonardtown, MD 20650

    This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy on a beautifully treed 4 acre lot. The first floor features a private office/den, formal living room, and elegant dining room. The large kitchen includes a cozy breakfast nook and opens to a step-down family room with a slider leading to a screened-in porch—ideal for indoor-outdoor living.Upstairs,

    Cynthia Crispell CENTURY 21 New Millennium

    20814 Deer Wood Park Dr, Leonardtown, MD 20650
    • 21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      21147 Catnip Ct, Leonardtown, MD 20650
      /56

      Est $687,940 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,296 Sq Ft

      21147 Catnip Ct, Leonardtown, MD 20650

      21147 Catnip Ct, Leonardtown, MD 20650

Showing Results 41 - 80, Page 2 of 18

Maryland St Marys County Leonardtown

Real Estate & Homes

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

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