25

Leonardtown, MD Homes for Sale under $700,000

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  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /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
  • Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    /19

    $449,900

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

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***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 4th bedroom with a

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    /12

    $454,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected 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

    Laura Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • 23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    /85

    $629,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    CREDIT FOR REPAIRS!! New Lower Price!!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

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • 40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    /77

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /64

    $700,000

    Open Sat 3PM - 5PM
    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

    New Construction Open Fri 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #116 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. This interior unit features an oversized

    Laura Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /75

    $645,000

    • 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
  • 23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    /2

    $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
  • 43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, 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
  • 22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    /34

    $575,000

    Open Sat 12PM - 3PM
    • 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
  • 23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, 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
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /54

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    40659 Klear Ct, Leonardtown, MD 20650

    Buyers, come take a look. The estate just dropped the price by $20,000 This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's bathroom shower has a leak and will probably need to be replaced. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650
  • 42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    /57

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    42195 White Point Beach Rd, Leonardtown, MD 20650

    Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still

    Carl Franzen Franzen Realtors, Inc.

    42195 White Point Beach Rd, Leonardtown, MD 20650
  • 23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    /37

    $590,000

    $10K 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 comfortable living space on a beautifully maintained 0.51-acre lot.Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • 42084 Wildflower Dr, Leonardtown, MD 20650
    42084 Wildflower Dr, Leonardtown, MD 20650
    42084 Wildflower Dr, Leonardtown, MD 20650
    /33

    $629,900

    New Construction
    • 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 inviting

    Laura Hefley RE/MAX One

    42084 Wildflower Dr, Leonardtown, MD 20650
  • 18800 McKays Beach Rd, Leonardtown, MD 20650
    18800 McKays Beach Rd, Leonardtown, MD 20650
    18800 McKays Beach Rd, Leonardtown, MD 20650
    /16

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    18800 McKays Beach Rd, Leonardtown, MD 20650

    This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one

    Chris Coughlan RE/MAX One

    18800 McKays Beach Rd, Leonardtown, MD 20650
  • Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ** Homesite #114 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. This interior unit features an oversized

    Laura Hefley RE/MAX One

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
  • 42096 Wildflower Dr, Leonardtown, MD 20650
    42096 Wildflower Dr, Leonardtown, MD 20650
    42096 Wildflower Dr, Leonardtown, MD 20650
    /45

    $619,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,976 Sq Ft

    42096 Wildflower Dr, Leonardtown, MD 20650

    Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is

    Laura Hefley RE/MAX One

    42096 Wildflower Dr, Leonardtown, MD 20650
  • 23898 Speith Rd, Leonardtown, MD 20650
    23898 Speith Rd, Leonardtown, MD 20650
    23898 Speith Rd, Leonardtown, MD 20650
    /36

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft

    23898 Speith Rd, Leonardtown, MD 20650

    **Seller offering $10,000 in Closing Help** Step into this ONE level, completely renovated home that was stripped down to the studs and everything was replaced from the roof to the floor, new well, and connected to public sewer in 2022. Expand without having to worry about where the septic or septic reserve area is. See and feel the craftsmanship that was put in with wood flooring, stainless

    Jimmy Hayden RE/MAX One

    23898 Speith Rd, Leonardtown, MD 20650
  • 42102 Wildflower Dr, Leonardtown, MD 20650
    42102 Wildflower Dr, Leonardtown, MD 20650
    42102 Wildflower Dr, Leonardtown, MD 20650
    /72

    $609,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,701 Sq Ft

    42102 Wildflower Dr, Leonardtown, MD 20650

    New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s suite

    Laura Hefley RE/MAX One

    42102 Wildflower Dr, Leonardtown, MD 20650
  • Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    /7

    $454,900

    New Construction $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

    ***** Hurry in! Secure your new home now and personalize it with your choice of interior colors. December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 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

    Laura Hefley RE/MAX One

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
  • 42108 Wildflower Dr, Leonardtown, MD 20650
    42108 Wildflower Dr, Leonardtown, MD 20650
    42108 Wildflower Dr, Leonardtown, MD 20650
    /31

    $614,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42108 Wildflower Dr, Leonardtown, MD 20650

    New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing. The Fenwick offers a smart, comfortable layout with a spacious family

    Laura Hefley RE/MAX One

    42108 Wildflower Dr, Leonardtown, MD 20650
  • 22503 Sparrow Ct, Leonardtown, MD 20650
    22503 Sparrow Ct, Leonardtown, MD 20650
    22503 Sparrow Ct, Leonardtown, MD 20650
    /43

    $575,000

    • 3 Beds
    • 3.5 Baths
    • 3,422 Sq Ft

    22503 Sparrow Ct, Leonardtown, MD 20650

    If you’re seeking a peaceful place with the ease of popping out to every convenience Leonardtown has to offer within a couple of minutes, without sacrificing being tucked away on a serene and sizeable landscape, this former custom builder’s home offers the perfect setting to settle into before summer ends. Sparrow Court is situated beautifully surrounded by just enough woods to offer both shade

    Melinda Brown EXP Realty, LLC

    22503 Sparrow Ct, Leonardtown, MD 20650
  • 41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    /47

    $624,900

    Open Sat 11AM - 2PM $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,690 Sq Ft

    41444 Osborne Ln, Leonardtown, MD 20650

    Charming Home in Prime Leonardtown LocationThis inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room

    Tracey Summers CENTURY 21 New Millennium

    41444 Osborne Ln, Leonardtown, MD 20650
Maryland St Marys County

Real Estate & Homes in Leonardtown, MD under $700,000

Home Prices in Leonardtown, MD

The median home sale price in Leonardtown, MD is $545,000, down 1% year-over-year. Homes in Leonardtown sell in 41 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$545,000
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$191
Number of Homes for Sale
33
Last 12 months Home Sales
197
Months of Supply
2.00
Median List Price
$555,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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