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Leonardtown, MD Homes for Sale under $700,000

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  • /33

    $450,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    20798 Waterside Dr, Leonardtown, MD 20650
  • /44

    $635,000

    $15K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,601 Sq Ft

    40751 Merlin Way, Leonardtown, MD 20650

    Welcome to this beautiful brick-front home in the highly sought-after Avenmar Community of historic Leonardtown, Maryland. Situated on over 3 private acres and tucked away on a secluded road shared by only three other homes, this property offers the perfect balance of privacy, nature, and convenience.Freshly updated with a new roof, new carpet throughout, and fresh paint, this

    Agent Photo

    Tracy Trammell

    Metro City Realty

    40751 Merlin Way, Leonardtown, MD 20650
  • /21

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ALMOST READY***Estimated Late October Delivery****Under Construction***Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or

    Laura Lee Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • /60

    $435,000

    • 4 Beds
    • 2.5 Baths
    • 2,624 Sq Ft

    40717 Lake and Breton View Dr, Leonardtown, MD 20650

    Breton Bay/Society Hill! Steps away and within view of the golf course. Desirable location within a sought after school zone. This community has water access to Breton Bay via community association (voluntary dues, No HOA). Affordability within a desirable location is hard to find so here's your change. This 2 story colonial style home has a large addition off the back of the home that features a

    Farrah Fuchs Redfin Corp

    40717 Lake and Breton View Dr, Leonardtown, MD 20650
  • /41

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23684 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersNatural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe Shower

    Quality Built Homes Builder
    23684 Dragonfly Ln, Leonardtown, MD 20650
  • /13

    $454,900

    New Construction Open Thu 11:30AM - 3:30PM
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    **** December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting!Homesite 157 Madison D1: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit

    Laura Lee Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • /85

    $610,000

    Open Sun 1PM - 3PM $69K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    Steal this house! Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • /74

    $699,900

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

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • /40

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23672 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSandstone Beige Carolina Bead SidingMusket Brown ShuttersBronze Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsWhite Ice Granite CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23672 Weeping Willow Way, Leonardtown, MD 20650
  • /42

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650

    ***** October Delivery *********** Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #139 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space.

    Laura Lee Hefley RE/MAX One

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
  • /94

    $680,000

    • 4 Beds
    • 2 Baths
    • 2,388 Sq Ft

    25375 Loveville Rd, Leonardtown, MD 20650

    Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2018, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers

    Kandy Moore RMG Realty

    25375 Loveville Rd, Leonardtown, MD 20650
  • /77

    $524,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    NEW PRICE — $524,900! If you’ve been waiting for the right opportunity to make your move to Breton Bay, this could be the one.There’s something special about living in Breton Bay. It’s the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /60

    $649,900

    Coming Soon Sep 18
    • 4 Beds
    • 2.5 Baths
    • 3,314 Sq Ft

    22157 Monterey Place, Leonardtown, MD 20650

    Nestled in the charming sought after Clearfields community, this stunning Colonial blends modern luxury with everyday comfort. Set on a beautifully landscaped 1.22-acre lot, this 4-bedroom, 2.5-bathroom home provides ample space for both relaxation and entertaining.At the heart of the home is a chef's dream kitchen, featuring custom cabinetry, gorgeous quartz countertops, a designer

    Tracey Summers CENTURY 21 New Millennium

    22157 Monterey Place, Leonardtown, MD 20650
  • /75

    $635,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside.The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • /56

    $615,000

    • 5 Beds
    • 4 Baths
    • 4,346 Sq Ft

    23620 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so

    Tyler Mattingly Coldwell Banker Premier

    23620 Gunnell Dr, Leonardtown, MD 20650
  • /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, Leonardtown, MD 20650
  • /45

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    22010 Society Hill Rd, Leonardtown, MD 20650

    Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area

    Fran Slade Compass

    22010 Society Hill Rd, Leonardtown, MD 20650
  • /77

    $695,000

    • 5 Beds
    • 2.5 Baths
    • 2,953 Sq Ft

    44450 Schumann Way, Leonardtown, MD 20650

    Welcome to this beautiful custom-built home situated on over 4 acres, offering an incredible combination of space, privacy, and versatility. A welcoming covered front porch and mature landscaping create beautiful curb appeal and the perfect place to sit back and enjoy the peaceful surroundings. Inside, you’ll find a thoughtfully designed floor plan featuring a main-level primary suite, spacious

    Jesieryl Hartzer CENTURY 21 New Millennium

    44450 Schumann Way, Leonardtown, MD 20650
  • /6

    $639,900

    Open Sat 11AM - 1PM Coming Soon Sep 10
    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft

    23444 Lindsay Dr, Leonardtown, MD 20650

    Discover a luxurious lifestyle in this stunning 2023 Colonial home nestled in the desirable Clark's Rest community. This exquisite residence boasts four spacious bedrooms and three and a half elegantly appointed bathrooms, perfect for both relaxation and entertaining. The heart of the home features high-end appliances, including an ENERGY STAR refrigerator and built-in microwave, ensuring both

    Natalya Ford RE/MAX One

    23444 Lindsay Dr, Leonardtown, MD 20650
  • /58

    $624,990

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    40611 Merion Ct, Leonardtown, MD 20650

    Welcome to 40611 Merion Court, Leonardtown, MD 20650! This stunning three-level Colonial offers the perfect blend of elegance, comfort, and resort-style living, ideally positioned with beautiful views backing directly to Breton Bay golf course. Featuring 4 bedrooms, 3.5 baths, and a fully finished basement, this home provides exceptional space for both everyday living and entertaining. The

    Kalee Kelly Infinitas Realty Group

    40611 Merion Ct, Leonardtown, MD 20650
  • /74

    $649,000

    $21K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • /44

    $695,000

    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    Located in the sought-after Clark's Rest community, this home features Marrick’s Kensington floor plan with a covered front entry and separate sitting porch. Inside, the two-story foyer opens to a formal dining room and versatile office, library, or playroom. The kitchen features a large center island, granite countertops, gas cooktop, double wall ovens, abundant cabinetry, butler’s pantry, and

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn Dr, Leonardtown, MD 20650
  • /41

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    41888 Jenkins Ct, Leonardtown, MD 20650

    Interior Photos Coming Soon! Expected on market date is Sept 1, 2026Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown

    Wayne & Christine Floyd RE/MAX Realty Group

    41888 Jenkins Ct, Leonardtown, MD 20650
  • /2

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,736 Sq Ft

    23354 Lindsay Dr, Leonardtown, MD 20650

    Welcome to this stunning rambler in the highly sought-after community of Clark's Rest! Thoughtfully designed with 9' ceilings, quartz countertops, designer finishes, and upgrades throughout, this home offers the perfect blend of style, comfort, and functionality.The main level features three spacious bedrooms and two full bathrooms, including a beautiful owner's suite with dual vanities. The

    Dorothy Bistransin Redfin Corp

    23354 Lindsay Dr, Leonardtown, MD 20650
  • /40

    $559,900

    $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    23636 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath Colonial offers nearly 3,000 square feet of living space on a beautifully maintained 0.51-acre lot, combining comfortable everyday living with plenty of room to grow.Step inside to a bright, inviting interior featuring new carpet and luxury vinyl plank flooring, giving the home a fresh, move-in-ready feel.

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • /41

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23679 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D2 Natural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Taj Quartz CountertopsSplendur Cream BacksplashDeluxe Shower in Primary

    Quality Built Homes Builder
    23679 Weeping Willow Way, Leonardtown, MD 20650
  • /42

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

    *** November Delivery ******Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #143 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space.

    Laura Lee Hefley RE/MAX One

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
  • /74

    $690,000

    Open Sun 1:30PM - 3:30PM
    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown’s most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a finished basement, and a large, level backyard with room to truly enjoy.Inside, a bright and

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • /33

    $629,900

    New Construction Open Thu 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42084 Wildflower Dr, Leonardtown, MD 20650

    To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start.This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an

    Laura Lee Hefley RE/MAX One

    42084 Wildflower Dr, Leonardtown, MD 20650
  • /36

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23714 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSavannah Wicker Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe

    Quality Built Homes Builder
    23714 Weeping Willow Way, Leonardtown, MD 20650
  • /28

    $600,000

    • 4 Beds
    • 3 Baths
    • 3,793 Sq Ft

    41524 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality.The thoughtful layout

    Billy Rabbitt The Southside Group Real Estate

    41524 Fairwood Ct, Leonardtown, MD 20650
  • /54

    $449,500

    $26K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    40659 Klear Ct, Leonardtown, MD 20650

    Discover a prime investment opportunity in the charming VILLAGES AT LEONARDTOWN! This 4-bedroom, 2.5-bath Colonial home, built in 2004, boasts 2,774 sq. ft. of potential. With a spacious unfinished basement featuring walkout stairs and rough bath plumbing, you have the perfect canvas to create additional living space or rental units, maximizing your return on investment. The property sits on a

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 2

Home Price Trends

Median Sale Price
$532,500
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$190
Number of Homes for Sale
55
Last 12 months Home Sales
198
Months of Supply
3.30
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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