Homes for Sale near Leonardtown Middle School

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  /8

  $330,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  24861 Three Notch Rd, Hollywood, MD 20636

  Welcome home to 24861 Three Notch Road! This beautifully updated rambler offers seamless one-level living, modern upgrades, and the perfect blend of convenience and country charm. Step inside to discover a bright and inviting layout featuring a fully renovated kitchen equipped with updated cabinetry, sleek countertops, and modern finishes—ideal for daily living and entertaining. The functional

  Stefanie Odom Home Towne Real Estate

  24861 Three Notch Rd, Hollywood, MD 20636
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  /10

  $190,000

  • Land
  • 5 Acres
  • $38,000 per Acre

  43488 Medleys Neck Rd, Leonardtown, MD 20650

  PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location.The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone

  Bill Oosterink CENTURY 21 New Millennium

  43488 Medleys Neck Rd, Leonardtown, MD 20650
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  /56

  $749,000

  $26K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,097 Sq Ft

  22393 Saint Clements Ave, Leonardtown, MD 20650

  Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the breathtaking water views, this light-filled home features an open-concept floor plan that seamlessly blends comfortable everyday living with exceptional entertaining space.Offering 4 bedrooms, 2 full baths, and 2 half baths, the home has been extensively

  Alyson Anderson Allfirst Realty, Inc.

  22393 Saint Clements Ave, Leonardtown, MD 20650
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  /72

  $609,900

  New Construction Open Thu 11:30AM - 3:30PM

  • 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

  Laura Lee Hefley RE/MAX One

  42102 Wildflower Dr, Leonardtown, MD 20650
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  /9

  $454,900

  New Construction Open Thu 11:15AM - 3:30PM $5K PRICE INCREASE

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

  Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

  ****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 townhome offering 2,554 sq ft of beautifully finished living space. This interior unit

  Laura Lee Hefley RE/MAX One

  Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
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  /37

  $85,000

  $9K PRICE DROP

  • Land
  • 4.11 Acres
  • $20,681 per Acre

  0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

  Nestled in the countryside of Leonardtown in St. Mary's County, this 4.11± acre wooded parcel on St. Andrews Church Road is a rare chance to build, invest, or settle into your own recreational retreat. The property already has a previous perc site in place for a conventional septic system. Soil stability testing will be required, but preliminary work points to favorable conditions. Buyers are

  Casey Kennedy Whitetail Properties Real Estate, LLC

  0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
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  /63

  $598,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,226 Sq Ft

  43732 Raspberry Ln, Hollywood, MD 20636

  Premier Waterfront Retreat with Unrivaled Patuxent River ViewsThis extraordinary residence rises above all other waterfront offerings—an exceptional retreat that delivers the best of both worlds with awe inspiring views of the water and the surrounding wooded landscape. From its commanding position, the home offers sweeping 180 degree vistas of the Patuxent River, creating a true “top of the

  Man Ngo Pearson Smith Realty, LLC

  43732 Raspberry Ln, Hollywood, MD 20636
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  /4

  $150,000

  • Land
  • 1.11 Acres
  • $135,135 per Acre

  25611 Clover Hill Rd, Hollywood, MD 20636

  Over an acre that has been perced at the intersection of Clover Hill Rd. and McIntosh Rd. Call listing agent with questions. Photos to be posted soon.

  Gloria Abell Coldwell Banker Premier

  25611 Clover Hill Rd, Hollywood, MD 20636
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  /2

  $290,000

  $10K PRICE DROP

  • Land
  • 15 Acres
  • $19,333 per Acre

  42700 Moll Dyer Rd, Leonardtown, MD 20650

  Discover a prime 15-acre parcel of land, offering a unique investment opportunity with significant potential returns. This property features a serene backdrop of trees and wooded areas, providing a tranquil setting while ensuring privacy. The sloping terrain enhances the natural beauty and could be ideal for various development projects, from residential homes to recreational retreats. The wooded

  Paul Fenton Coldwell Banker Premier

  42700 Moll Dyer Rd, Leonardtown, MD 20650
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  /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
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  /3

  $175,000

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

  22501 Bull Rd, Leonardtown, MD 20650

  One of only two lots remaining! 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

  22501 Bull Rd, Leonardtown, MD 20650
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  /4

  $10,000

  $12K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $31,250 per Acre

  0 Lot 12 Skyview Dr, Hollywood, MD 20636

  This vacant lot in Hollywood, MD offers a wonderful opportunity to build your dream home in a peaceful and scenic setting. Located just a short drive from NAS Patuxent River and Dahlgren Base, the property provides easy access to work and daily conveniences, while offering a serene environment for relaxation. The lot is surrounded by beautiful natural landscapes, including the nearby Patuxent

  Sarah Reynolds Keller Williams Realty

  0 Lot 12 Skyview Dr, Hollywood, MD 20636
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  /39

  $449,900

  New Construction

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

  23725 Dragonfly Ln, Leonardtown, MD 20650

  Interior Elevation D3 with DormersHerringbone Carolina Bead SidingMusket Brown ShuttersSedona Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorLVT in Bathrooms and Laundry RoomUpgraded Maple Kitchen CabinetsRoccoco Quartz CountertopsSplendur White BacksplashDeluxe Shower

  Quality Built Homes Builder

  23725 Dragonfly Ln, Leonardtown, MD 20650
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  /68

  $764,987

  • 3 Beds
  • 4 Baths
  • 2,551 Sq Ft

  43816 Raspberry Ln, Hollywood, MD 20636

  Experience timeless English Tudor character paired with sweeping, unobstructed views of the Patuxent River. From the moment you step inside, the home’s expansive windows frame miles of serene waterfront, filling each room with natural light and a sense of calm that only riverside living can offer. With three bedrooms plus a dedicated office, the layout balances comfort and functionality—ideal for

  Patrick Dugan O'Brien Realty ERA Powered

  43816 Raspberry Ln, Hollywood, MD 20636
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  /31

  $614,900

  New Construction Open Thu 11:30AM - 3:30PM

  • 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

  Laura Lee Hefley RE/MAX One

  42108 Wildflower Dr, Leonardtown, MD 20650
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  /4

  $444,900

  • 3 Beds
  • 2 Baths
  • 1,497 Sq Ft

  25397 Allston Ln, Hollywood, MD 20636

  Previous Deal Fell Through.Welcome home to this beautifully renovated rambler located in the desirable Gillens Grove community of Hollywood, Maryland! This charming 3-bedroom, 2-bath home has been thoughtfully updated and is move-in ready.Step inside to stunning hardwood floors that flow throughout the spacious, open-concept living area. The bright and inviting kitchen features gorgeous

  Gloria Abell Coldwell Banker Premier

  25397 Allston Ln, Hollywood, MD 20636
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  /2

  $130,000

  • Land
  • 4.08 Acres
  • $31,863 per Acre

  0 Cat Creek Rd Unit MDSM2029850, Mechanicsville, MD 20659

  Build Your Dream on 4.08 Acres in Riverwood Farms Mechanicsville, MD. Welcome to Cat Creek Road, nestled in the Riverwood Farms subdivision in Mechanicsville. This expansive 4.08-acre lot offers the perfect blend of privacy and convenience, providing an incredible opportunity to build your custom dream home in a peaceful, wooded setting. The property has already passed perc test, streamlining the

  Michael Fitzgerald, II RE/MAX One

  0 Cat Creek Rd Unit MDSM2029850, Mechanicsville, MD 20659
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  /47

  $599,900

  $50K 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

  Tracey Summers CENTURY 21 New Millennium

  41444 Osborne Ln, Leonardtown, MD 20650
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  /35

  $840,000

  • Land
  • 10.2 Acres
  • $82,353 per Acre

  0 Ferny Hills Ln, Leonardtown, MD 20650

  Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat.With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and

  Jennifer Goddard CENTURY 21 New Millennium

  0 Ferny Hills Ln, Leonardtown, MD 20650
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  /17

  $350,000

  • 5 Beds
  • 2 Baths
  • 1,552 Sq Ft

  23011 Newtowne Neck Rd, Leonardtown, MD 20650

  Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, manufactered two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant room for outdoor recreation, gardening, equipment storage,

  Kelly Jackson Samson Properties

  23011 Newtowne Neck Rd, Leonardtown, MD 20650

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