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Homes for Sale near Leonard Hall Junior Naval Academy

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  • /75

    $784,990

    • 5 Beds
    • 3 Baths
    • 6,064 Sq Ft

    40801 Kiskadee Ln, Leonardtown, MD 20650

    Welcome to 40801 Kiskadee Lane — a truly exceptional residence nestled on over 3 private acres in the prestigious waterfront community of Avenmar. This grand colonial home is an entertainer’s dream, offering over 6,000 square feet of beautifully designed living space, and is specially offered with the last available building lot in the community — an additional 3.5+ acre parcel for $200,000,

    Pattee McInerney Scott McInerney RE/MAX One

    40801 Kiskadee Ln, Leonardtown, MD 20650
  • /67

    $799,900

    • Land
    • 3.56 Acres
    • $224,691 per Acre

    39645 Sweetpea Ln, Leonardtown, MD 20650

    UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless

    Sandi Denny CENTURY 21 New Millennium

    39645 Sweetpea Ln, Leonardtown, MD 20650
  • /49

    $499,900

    • 4 Beds
    • 3.5 Baths
    • 3,087 Sq Ft

    22950 Wintergreen Ln, California, MD 20619

    Nestled in the sought-after Wildewood neighborhood, this exquisite 4-bedroom, 3.5-bathroom home at 22950 Wintergreen Ln offers luxury and functionality. Spanning three levels, this residence boasts a finished basement with a stylish bar, billiard room, media area, full bathroom, and convenient walk-out access—perfect for entertaining or relaxation.The main floor welcomes you with a

    Matthew Burgan Infinitas Realty Group

    22950 Wintergreen Ln, California, MD 20619
  • /126

    $5,950,000

    • 5 Beds
    • 8 Baths
    • 12,113 Sq Ft

    41505 Knight Rd, Leonardtown, MD 20650

    Stunning. Welcome to a world of unparalleled luxury and breathtaking beauty. Nestled along the tranquil waters off of the Potomac River, this custom-built four level waterfront estate on almost 18 acres, is a testament to architectural brilliance and sophisticated design. As you approach the grand entrance, you are greeted by a circular driveway, detached 3-car garage, attached 2-car garage,

    Travis Gray Engel & Völkers Annapolis

    41505 Knight Rd, Leonardtown, MD 20650
  • /80

    $524,900

    • 4 Beds
    • 3.5 Baths
    • 2,990 Sq Ft

    23371 Hosta Ln, California, MD 20619

    Beautifully maintained 4-bedroom, 3.5-bath home offering nearly 3,000 sq ft of living space in the sought-after Wildewood community. Built in 2006, this residence features a finished basement with workshop space, a versatile 4th-floor loft, and a 2-car rear-entry garage. Recent updates include a brand-new water heater replaced in 2025 and a roof that’s less than 3 years old. The seller is also

    Katy Galloway CENTURY 21 New Millennium

    23371 Hosta Ln, California, MD 20619
  • /59

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 3,014 Sq Ft

    41998 Pleasant Valley Ct, Hollywood, MD 20636

    This exceptional one-level rambler sits on 17 acres of peaceful, picturesque land, offering a rare blend of upscale living and rural charm. From the moment you arrive, you'll appreciate the serenity of the surroundings complete with scenic pond views, a circular paved driveway, and ample space for both leisure and purpose. Step inside to find an open-concept layout designed for both comfort and

    Deanna Havenner CENTURY 21 New Millennium

    41998 Pleasant Valley Ct, Hollywood, MD 20636
  • /39

    $411,000

    • 4 Beds
    • 4 Baths
    • 2,016 Sq Ft

    43651 Marguerite St, California, MD 20619

    This stunning end-unit townhome boasts an abundance of natural light and offers 4 bedrooms, 2 full baths, 2 half baths, and just had a new roof put on! Meticulously maintained & move-in ready, the home features new carpeting in the bedrooms and stairways, fresh paint, and a new AC unit installed in 2021.The main level includes a versatile 4th bedroom and a convenient half bath. The second

    Rachel Hutton JPAR Real Estate Professionals

    43651 Marguerite St, California, MD 20619
  • /82

    $714,900

    • 4 Beds
    • 4.5 Baths
    • 4,399 Sq Ft

    22951 Cattail Ln, California, MD 20619

    Welcome to 22951 Cattail Ln, a beautifully maintained custom brick home in the sought-after Redwood subdivision of Wildewood. Perfectly situated near top-rated schools, shopping, and PAX River NAS, this home offers a blend of elegance, functionality, and modern updates. Step inside to find grand-scale living with 4 spacious bedrooms and 3 full baths upstairs, plus a flex room and full bath in the

    Charlotte Long EXP Realty, LLC

    22951 Cattail Ln, California, MD 20619
  • /59

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 3,014 Sq Ft

    41998 Pleasant Valley Ct, Hollywood, MD 20636

    This stunning and beautifully maintained Rambler sits on 17 picturesque acres, offering a rare opportunity for those seeking space, serenity, and unlimited potential. Whether you're envisioning a small vineyard, an events or wedding venue, a horse farm, farmette, or a thriving home-based business, this property is ready to accommodate your vision. The home features a well-designed floorplan, an

    Deanna Havenner CENTURY 21 New Millennium

    41998 Pleasant Valley Ct, Hollywood, MD 20636
  • /3

    $95,000

    • Land
    • 0.84 Acre
    • $113,095 per Acre

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Prime Build-Ready Lot – Bring Your Dream Home to Life!Discover the perfect canvas for your dream home on this beautiful [size] acre lot in [location]! This perc-tested property is ready for construction, offering the flexibility to bring your own builder or partner with Graham & Co Custom Creations to design and build a custom home tailored to your vision.Located in a serene

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • /32

    $429,900

    • 3 Beds
    • 3 Baths
    • 2,028 Sq Ft

    22362 Armstrong Dr, Leonardtown, MD 20650

    Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MDNestled in the desirable Society Hill neighborhood of Leonardtown, this one-of-a-kind property offers a rare opportunity with its expansive double lot—a true gem in the community. While the home retains a timeless charm, it presents an exciting chance to add your personal touch and modern updates.Inside, you'll

    Chris Hill CENTURY 21 New Millennium

    22362 Armstrong Dr, Leonardtown, MD 20650
  • /13

    $299,999

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft

    20959 Redgate Ln, Leonardtown, MD 20650

    A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space

    Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
  • /91

    $699,900 Open Sat 11AM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 3,478 Sq Ft

    23773 Meredith Ct, Hollywood, MD 20636

    Spacious home in desirable Hollywood location. (Abell's Ridge) The main level greets you with hardwood flooring in the Foyer. Large owners suite with two walk in closets. The owner's full bath features tile flooring, a double jetted soaking tub, separate shower.Four car garage with work area of garage heated. New HVAC in 2023. Fireplace has wood stove insert. Unfinished basement .

    Gloria Abell Coldwell Banker Jay Lilly Real Estate

    23773 Meredith Ct, Hollywood, MD 20636
  • /6

    $159,900

    • Land
    • 1.49 Acres
    • $107,315 per Acre

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Charming Cul-de-Sac Lot in Breton Oaks – No HOA!Discover the perfect place to build your dream home on this beautiful, private lot located in the peaceful cul-de-sac of Breton Oaks. This small, custom-built subdivision offers a tranquil setting, with all homes in the neighborhood uniquely designed by St. Maries Builders. You can choose to build with them or bring your own builder to bring

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • /29

    $999,900

    • Land
    • 10 Acres
    • $98,029 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this breathtaking 10.2-acre waterfront lot overlooking the serene Breton Bay. This rare gem is not just a piece of land; it's an invitation to create a life of adventure, tranquility, and natural beauty.Endless Possibilities:With perc approval already in place, this stunning property is ready for your dream home. Imagine waking up to stunning views

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • /5

    $245,000

    • 2,160 Sq Ft

    23706 Three Notch Rd, Hollywood, MD 20636

    LOWER PRICE! DO NOT ATTEMPT TO ENTER THE HOUSE! Owner is unsure of structural condition. Said home was vandalized and stripped of most everything. It is at best, a Major Rehab. No one is to enter the Property without special permission and having signed a Waiver. If your Client wants to see the interior, it can be arranged after signing Waivers. Anyone entering the home would have had to sign

    Don Wares Long & Foster Real Estate, Inc.

    23706 Three Notch Rd, Hollywood, MD 20636
  • /2

    $45,900

    • Land
    • 0.71 Acre
    • $64,648 per Acre

    25106 Pinto Dr, Hollywood, MD 20636

    DISCOVER THIS .71 ACRE LOT AVAILABLE IN SOUGHT AFTER FENWICK MANOR COMMUNITY WITHIN SAINT MARY'S COUNTY. ZONING RNC. DRIVE BY TODAY TO DETERMINE FOR YOURSELF HOW IT CAN WORK FOR YOUR NEEDS! OWNER FINANCING AVAILABLE.

    Jennifer Drennan Taylor Properties

    25106 Pinto Dr, Hollywood, MD 20636
  • /2

    $225,000

    • Land
    • 8 Acres
    • $30,000 per Acre

    0 Wathen Rd, Leonardtown, MD 20650

    NEW CONSTRUCTION TO BE BUILT. This stunning lot is co-marketed with Caruso Homes, featuring the impressive DEERFIELD model—a four-bedroom floor plan with the option to include a convenient In-Law suite on the main level. Embrace the joy of gathering with loved ones in this thoughtfully designed open-concept home, highlighted by a spacious great room seamlessly connected to the kitchen. The

    Amber Williams Amber & Company Real Estate

    0 Wathen Rd, Leonardtown, MD 20650
  • /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2012646, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2012646, Leonardtown, MD 20650
  • /3

    $175,000

    • Land
    • 8 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, Leonardtown, MD 20650
  • /3

    $180,000

    • Land
    • 1.87 Acres
    • $96,257 per Acre

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left in Breton Knolls. Breton Knolls is a 24 lot subdivision in Leonardtown with 1 - 7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • /2

    $229,991

    • 4 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    24399 Morgan Rd, Hollywood, MD 20636

    Diamond in the rough! Solid vintage home on large corner lot is ready for one lucky owners sweat equity or for easy renovation financing. Completed improvements are in; new roof, economical oil fired boiler for wonderful radiant hot water baseboard heat, replacement thermopane windows, environmentally sound mound septic system and more! List price reflects being sold AS IS. Visit soon and see

    Juan Aranda CENTURY 21 New Millennium

    24399 Morgan Rd, Hollywood, MD 20636
  • /5

    $750,000

    • Land
    • 83 Acres
    • $9,065 per Acre

    0 Saint Andrews Church Rd, California, MD 20619

    Mike Jordan CENTURY 21 New Millennium

    0 Saint Andrews Church Rd, California, MD 20619
  • /7

    $675,000 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
  • /3

    $530,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft

    41815 Chelsey Faye Ln, Leonardtown, MD 20650

    Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home is a modestly sized one story design that is loaded with all the necessities. Beautiful white siding and stained timber accents are perfect material choices for the farmhouse style. Offering an open main level with one large space for living and dining. The family room has a high ceiling. Enjoy the cozy ambiance of this home

    Jessica Ascenzo JPAR Real Estate Professionals

    41815 Chelsey Faye Ln, Leonardtown, MD 20650
  • /36

    $859,900 New Construction

    • 4 Beds
    • 2.5 Baths

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 square feet of luxury living. As you step inside, you are greeted by an open layout that radiates warmth and spaciousness. The heart of the home, a two-story family room with fireplace, is bathed in natural light, creating an inviting atmosphere for entertaining and relaxation. Cook gourmet

    Michele Posey RE/MAX Realty Group

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • /38

    $884,900 New Construction

    • 5 Beds
    • 2.5 Baths
    • 3,127 Sq Ft

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    To Be Built - A Breton Knolls exclusive offering. Be the first to call this to-be-built custom-crafted home yours! Located in the heart of Leonardtown on oversized lots, this new 24-lot subdivision offers an elegantly crafted home by well-known local builder, Litz Custom Homes. The Jackson floor plan perfectly combines the essence of a Colonial Farmhouse with a modern twist to include over 3,000

    Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
  • /49

    $395,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,638 Sq Ft

    44219 Beaver Creek Dr, California, MD 20619

    Welcome to Wildewood one of Saint Mary's sought after neighborhoods. This beautiful end unit townhome offers 3 levels of living. Main level living offers a dining or office area, gourmet kitchen with center island, and a combination kitchen / living room for all your gatherings. The middle level offers 3 generous bedrooms with walk in closets, new carpeting, and recessed lighting. The 2 bedrooms

    Chris Coughlan RE/MAX One

    44219 Beaver Creek Dr, California, MD 20619
  • /45

    $425,000 Open House 7/26

    • 3 Beds
    • 4 Baths
    • 2,168 Sq Ft

    23307 Sugar Pine Ln, California, MD 20619

    Take a look at this like-new townhome built in 2023. This spacious and modern home features an open-concept layout perfect for entertaining, with abundant natural light and high-end finishes throughout. The heart of the home is a beautifully appointed kitchen with a large island, stainless steel appliances, sleek cabinetry, and plenty of counter space. Upstairs you'll find generously sized

    Jesieryl Hartzer CENTURY 21 New Millennium

    23307 Sugar Pine Ln, California, MD 20619
  • /2

    $495,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    41900 Nazareth Ct, Leonardtown, MD 20650

    Welcome to the Academy Hills of Leonardtown. Just minutes from historic downtown Leonardtown, this impeccably maintained Colonial blends timeless charm with modern upgrades. The main level features a traditional floor plan, recent upgrades including stainless steel appliances—highlighted by a brand-new refrigerator—plenty of cabinet space, a formal dining room, and a convenient powder room.

    Marizel Brewington RE/MAX One

    41900 Nazareth Ct, Leonardtown, MD 20650
  • /2

    $474,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,545 Sq Ft

    44313 Poplar Wood Dr, California, MD 20619

    Welcome to 44313 Poplar Wood Dr, a spacious 4-bedroom, 2.5-bath home nestled on a serene, wooded lot in the heart of the highly sought-after Wildewood community. Perched atop a gentle hill, this home offers exceptional privacy and beautiful views of the surrounding landscape.Step inside to discover a sun-filled interior with generously sized rooms and an open layout perfect for

    Matthew Burgan Infinitas Realty Group

    44313 Poplar Wood Dr, California, MD 20619
  • /2

    $355,000 Open House 8/09

    • 4 Beds
    • 3.5 Baths
    • 1,924 Sq Ft

    23175 Mountain Laurel Ln, California, MD 20619

    Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom inner townhome offering spacious, stylish living in the heart of Wildewood. The main level features an open-concept kitchen with granite countertops, a large island, stainless steel appliances, tile backsplash, and a cozy dining area that opens to a balcony deck—perfect for entertaining or relaxing.Retreat to the spacious primary

    Laura Holley O'Brien Realty ERA Powered

    23175 Mountain Laurel Ln, California, MD 20619
  • /37

    $384,000

    • 3 Beds
    • 1.5 Baths
    • 1,626 Sq Ft

    24313 Mervell Dean Rd, Hollywood, MD 20636

    TAKE ADVANTAGE OF THE PRICE REDUCTION FOR THIS HIDDEN GEM!!Are you interested in fine living with a bit of seclusion? This fully renovated, all brick, custom-built, late 1950s era home could be your dream home! Featuring 3 bedrooms, a brick fireplace, and separate living and dining rooms, the property includes central air, brand new water heater and furnace, and newer kitchen cabinetry.

    Suzette Hampton Samson Properties

    24313 Mervell Dean Rd, Hollywood, MD 20636
  • /24

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft

    22405 Indian Bridge Rd, California, MD 20619

    Sited on a one-acre level lot, this spacious ranch-style home is waiting for you to make it yours. It has over 1800 sqft of living space, a large entertainment room, and a formal living room. The home has hardwood floors and ceramic tile, and it has a pool house with a large inground deep pool. Conveniently located

    Pennie Platt Home Towne Real Estate

    22405 Indian Bridge Rd, California, MD 20619

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