83

Homes for Sale near Leonardtown Middle School

Section Image Section Image
  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect 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

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 376-2980

    20798 Waterside Dr, Leonardtown, MD 20650
  • 24140 Wheatherby Dr, Hollywood, MD 20636
    24140 Wheatherby Dr, Hollywood, MD 20636
    24140 Wheatherby Dr, Hollywood, MD 20636
    /10

    $549,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    24140 Wheatherby Dr, Hollywood, MD 20636

    You could be the best of the neighborhood in this beautiful well kept home on one of the largest lots (1.3acres) in the subdivision. Seller is replacing the carpet and doing some touch up painting to make this property prestine and move in ready. Cozy up in the Family Room with the gas fireplace or use as ambience with your beautiful kitchen. 4 Bedrooms, 2.5 Baths, 2 Car Garage with plenty of

    Agent Photo

    Jimmy Hayden

    RE/MAX Realty Group

    (240) 226-1475

    24140 Wheatherby Dr, Hollywood, MD 20636
  • 24554 Pin Cushion Rd, Leonardtown, MD 20650
    24554 Pin Cushion Rd, Leonardtown, MD 20650
    /2

    $355,000 Open House 6/07

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    24554 Pin Cushion Rd, Leonardtown, MD 20650

    Welcome to your next adventure! This almost all brick rambler sits on 1.26 acres with NO HOA — giving you the freedom to live how you want. Inside, you’ll find 3 bedrooms, 2 full baths, and a private primary suite ready to be your personal retreat. Outside, enjoy a detached carport, a storage shed for all your gear, and a super convenient U-shaped driveway. The location can’t be beat — minutes to

    Agent Photo

    Connie Fitzgerald

    RE/MAX Closers

    (240) 571-2982

    24554 Pin Cushion Rd, Leonardtown, MD 20650
  • 25102 Three Notch Rd, Hollywood, MD 20636
    25102 Three Notch Rd, Hollywood, MD 20636
    25102 Three Notch Rd, Hollywood, MD 20636
    /56

    $465,000

    • 3 Beds
    • 3 Baths
    • 1,968 Sq Ft

    25102 Three Notch Rd, Hollywood, MD 20636

    Welcome to this charming and beautifully maintained single-story home in SOUGHT after Hollywood. This inviting property features a spacious porch perfect for relaxing or entertaining, adorned with hanging flower baskets and classic railing. The home boasts a light-colored exterior with new roof (2022), skylights for added natural light, and attractive landscaping along the front yard.This 3

    Agent Photo

    Connie Gunn

    CENTURY 21 New Millennium

    (240) 387-9369

    25102 Three Notch Rd, Hollywood, MD 20636
  • 40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    /75

    $460,000

    • 4 Beds
    • 2 Baths
    • 2,524 Sq Ft

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    Have you been searching for a home with the PERFECT Water Views!! Without; the Water view price??This home may be what your heart Desires!! Walk your kayaks right down the SAME block to the community beach access spot. The "walking beach" as they call it. This home has water views from BOTH levels. There are wood burning stoves on BOTH levels. The main beach access with playground and

    Agent Photo

    Connie Gunn

    CENTURY 21 New Millennium

    (240) 808-7689

    40827 Lake and Breton View Dr, Leonardtown, MD 20650
  • 24083 Woodmore Dr, Hollywood, MD 20636
    24083 Woodmore Dr, Hollywood, MD 20636
    24083 Woodmore Dr, Hollywood, MD 20636
    /68

    $669,000

    • 4 Beds
    • 2.5 Baths
    • 3,055 Sq Ft

    24083 Woodmore Dr, Hollywood, MD 20636

    This home is 2 years young, featuring an open floor plan, dedicated office, LVL flooring through the main level and the upstairs hall and owners suite. The back yard has a custom paver patio and a fully fenced. The home features a gourmet kitchen, wall oven, large island and tile backsplash with a pot filler. Home sits at the end of the street and encounters little through traffic.

    James Dick Long & Foster Real Estate, Inc.

    24083 Woodmore Dr, Hollywood, MD 20636
  • 24643 Maple Valley Ln, Hollywood, MD 20636
    24643 Maple Valley Ln, Hollywood, MD 20636
    24643 Maple Valley Ln, Hollywood, MD 20636
    /39

    $614,900

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    24643 Maple Valley Ln, Hollywood, MD 20636

    Welcome to your serene retreat in Hollywood, MD! This impressive 2424 sq ft home boasts 4 spacious bedrooms and 2.5 well-appointed bathrooms. The modern kitchen is a highlight, featuring stainless steel appliances, granite countertops, and a custom tiled backsplash, with plenty of counter space making it perfect for culinary enthusiasts. The primary suite is spacious with a large walk-in closet

    Leah Hounshell Home Towne Real Estate

    24643 Maple Valley Ln, Hollywood, MD 20636
  • 42439 Dean Forest Ct, Leonardtown, MD 20650
    42439 Dean Forest Ct, Leonardtown, MD 20650
    42439 Dean Forest Ct, Leonardtown, MD 20650
    /31

    $574,000

    • 5 Beds
    • 3.5 Baths
    • 2,519 Sq Ft

    42439 Dean Forest Ct, Leonardtown, MD 20650

    Welcome home to this beautiful 5 Bedroom 3.5 Bath Colonial in Leonardtown!! You will not want to miss this one! This home features a fully renovated kitchen done in 2024, includes a massive kitchen island, tons of counter space, all granite with a quartz back splash, new SS appliances, cabinets, recessed lighting. and new Porcelain kitchen floors. Beautiful Hand Scraped Hickory engineered wood

    DJ Brady EXP Realty, LLC

    42439 Dean Forest Ct, Leonardtown, MD 20650
  • 42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    42261 Bird Haven Dr, Leonardtown, MD 20650
    /79

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 2,358 Sq Ft

    42261 Bird Haven Dr, Leonardtown, MD 20650

    Welcome to this charming 4-bedroom, 2.5-bathroom home in the sought-after Kingston Estates in Leonardtown. Lovingly maintained by its original owners, this home offers a perfect blend of comfort, style, and tranquility.As soon as you step inside, you’ll be greeted by bright, airy living spaces that create a warm, inviting atmosphere. The kitchen shines with its thoughtful design, featuring

    Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
  • 40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    /61

    $785,000

    • 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
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /48

    $659,900

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

    41430 Challedon Way, Leonardtown, MD 20650

    Colonial Home in Leonard's Grant – Prime Corner Lot Across from Amenities!Welcome to this spacious and well-appointed home in the sought-after Leonard's Grant community, ideally situated on a desirable corner lot directly across from the neighborhood pool, playground, and clubhouse. Enjoy views of open green space and an easy walk to downtown Leonardtown's charming restaurants and shops.The main

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    41430 Challedon Way, Leonardtown, MD 20650
  • 27273 Holly Ln, Mechanicsville, MD 20659
    27273 Holly Ln, Mechanicsville, MD 20659
    27273 Holly Ln, Mechanicsville, MD 20659
    /40

    $650,000

    • 3 Beds
    • 2 Baths
    • 1,940 Sq Ft

    27273 Holly Ln, Mechanicsville, MD 20659

    Welcome to 27273 Holly Lane, a beautifully renovated water view home in the Sandgates community of Mechanicsville. Situated on scenic Cat Creek, just off the Patuxent River, this property offers a unique opportunity to enjoy the best of Maryland’s lifestyle.The home features over 2,000 sq ft, including 3 bedrooms, 2 full baths, a dedicated office, and a light-filled living room with large bay

    Rudy Carrico Baldus Real Estate, Inc.

    27273 Holly Ln, Mechanicsville, MD 20659
  • 41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    41430 Whimsical Ct, Leonardtown, MD 20650
    /30

    $649,999

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft

    41430 Whimsical Ct, Leonardtown, MD 20650

    This home is a MUST SEE!!!!Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful updates throughout, this home is perfect for growing families, multi-generational

    Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
  • 23293 Nicholson St, Hollywood, MD 20636
    23293 Nicholson St, Hollywood, MD 20636
    23293 Nicholson St, Hollywood, MD 20636
    /43

    $700,000

    • 5 Beds
    • 3 Baths
    • 3,036 Sq Ft

    23293 Nicholson St, Hollywood, MD 20636

    Step into this inviting home designed for a retreat that fulfills your every desire. This modern ranch rambler features an open-concept layout with three bedrooms and two full bathrooms conveniently located on the main level. Just off the entrance, you'll find a cozy library nook or separate sitting space, perfect for enjoying quality time reading or chatting with friends. The focal point of the

    Diana Charles Douglas Samson Properties

    23293 Nicholson St, Hollywood, MD 20636
  • 23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    23578 Pine Bluff Way, Leonardtown, MD 20650
    /75

    $599,900

    • 3 Beds
    • 3.5 Baths
    • 3,188 Sq Ft

    23578 Pine Bluff Way, Leonardtown, MD 20650

    LOCATION...LOCATION...LOCATION! THIS LOVELY HAYDEN MODEL IS NESTLED RIGHT AT THE HEAD OF THE VILLAGE GREEN IN DESIRABLE LEONARD'S GRANT NEIGHBORHOOD. 3 BEDROOMS AND 2 FULL BATHS ON SECOND LEVEL AND A PARTIALLY FINISHED BASEMENT TO INCLUDE REC ROOM AND FULL BATH. UNFINISHED SPACE COULD BE FINISHED FOR THE 4TH BEDROOM OR GREAT STORAGE. OPEN FLOOR PLAN FEATURES HARDWOOD FLOORS, GRANITE

    Jennifer Mullennix CENTURY 21 New Millennium

    23578 Pine Bluff Way, Leonardtown, MD 20650
  • 23275 Jenifer Ct, Leonardtown, MD 20650
    23275 Jenifer Ct, Leonardtown, MD 20650
    23275 Jenifer Ct, Leonardtown, MD 20650
    /113

    $649,900

    • 6 Beds
    • 4.5 Baths
    • 6,311 Sq Ft

    23275 Jenifer Ct, Leonardtown, MD 20650

    Welcome to this three-level home located in the Single Tree community, just a short walk from vibrant downtown. Boasting over 6,700 square feet of beautifully designed living space, this home offers 6 bedrooms, 4.5 bathrooms, and a thoughtfully crafted layout perfect for both everyday living and entertaining.The main level features gleaming hardwood floors, a soaring two-story family room

    Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
  • 22900 Camden Ct, Hollywood, MD 20636
    22900 Camden Ct, Hollywood, MD 20636
    22900 Camden Ct, Hollywood, MD 20636
    /59

    $739,000

    • 5 Beds
    • 3.5 Baths
    • 4,212 Sq Ft

    22900 Camden Ct, Hollywood, MD 20636

    Nestled in the sought-after Forrest Farm neighborhood, this stunning 5-bedroom, 3.5-bath colonial offers space, style, and functionality on a 1-acre corner lot. With over 3,100 finished sq ft above ground and an additional 1,100 finished sq ft in the basement, this home is ideal for those who crave room to grow, entertain, and unwind. Step inside to discover a gourmet kitchen, highlighted by an

    Cynthia Lisa RE/MAX One

    22900 Camden Ct, Hollywood, MD 20636
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /32

    $699,900

    • 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
  • 21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    21897 Fairway Dr, Leonardtown, MD 20650
    /70

    $649,000

    • 5 Beds
    • 2.5 Baths
    • 3,664 Sq Ft

    21897 Fairway Dr, Leonardtown, MD 20650

    Custom-Built Beauty Overlooking Breton Bay Golf Course! Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunning 5-bedroom, 2.5-bath custom-built home in the desirable Breton Bay community. This home is in impeccable condition with numerous upgrades—simply move right in and start enjoying luxury living! Main Level Highlights:9 ft. ceilings with elegant crown molding throughoutGleaming hardwood

    Matthew Burgan Infinitas Realty Group

    21897 Fairway Dr, Leonardtown, MD 20650
  • 23348 Lindsay Dr, Leonardtown, MD 20650
    23348 Lindsay Dr, Leonardtown, MD 20650
    23348 Lindsay Dr, Leonardtown, MD 20650
    /33

    $635,000

    • 5 Beds
    • 4 Baths
    • 3,540 Sq Ft

    23348 Lindsay Dr, Leonardtown, MD 20650

    Seller is offering $10,000 in closing help! It can also be used to buy down the interest rate. Welcome to 23348 Lindsay Drive — where space, style, and comfort come together in the heart of Leonardtown’s sought-after Clark’s Rest community. This nearly new 5-bedroom, 4-bath home offers over 3,500 sq ft of beautifully designed living space with thoughtful upgrades and a flexible floor plan perfect

    Christi Turman-Rojas Fairfax Realty Premier

    23348 Lindsay Dr, Leonardtown, MD 20650
  • 41536 Fairwood Ct, Leonardtown, MD 20650
    41536 Fairwood Ct, Leonardtown, MD 20650
    41536 Fairwood Ct, Leonardtown, MD 20650
    /75

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 3,080 Sq Ft

    41536 Fairwood Ct, Leonardtown, MD 20650

    PRICE IMPROVEMENT! This home is less than 2 years young in the sought after, planned Clarks Rest community! Four (4) Bedrooms, Three (3) Full Baths, Powder Room Main Floor, and Two (2) Car Garage with EV Charger. When you enter the Two Story Foyer, you'll be welcome to the Formal Living Room on the right with the Formal Dining Room to the left and open to the Family Room with Gas Fireplace.

    Lynn Smithburger CENTURY 21 New Millennium

    41536 Fairwood Ct, Leonardtown, MD 20650
  • 22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    /58

    $650,000

    • 4 Beds
    • 3.5 Baths
    • 2,948 Sq Ft

    22626 Chickadee Ln, Leonardtown, MD 20650

    PRICE REDUCED!! Welcome to your new home in the lovely Avenmar Community! Upon entering your new home you’re greeted by a stunningly adorned 2 story foyer. As you make your way around the lower level you will find a formal living and dining room with a timeless trim work design and new LVP installed in 2022. Walking into the kitchen you have an open concept flowing seamlessly into your family

    Dillon Wise JPAR Real Estate Professionals

    22626 Chickadee Ln, Leonardtown, MD 20650
  • 26366 Mar A Lee Ct, Mechanicsville, MD 20659
    26366 Mar A Lee Ct, Mechanicsville, MD 20659
    26366 Mar A Lee Ct, Mechanicsville, MD 20659
    /22

    $569,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,280 Sq Ft

    26366 Mar A Lee Ct, Mechanicsville, MD 20659

    *** To Be Built with permit in hand**** Welcome to your dream home in the heart of Mechanicsville! Nestled on a quiet dead-end street, this stunning colonial boasts an abundance of space and breathtaking features. The main level is the perfect layout with a home office, the fabulous kitchen with granite countertops and stainless steel appliances will make meal preparation a pleasure, spacious

    Robin Cavallaro RE/MAX Realty Group

    26366 Mar A Lee Ct, Mechanicsville, MD 20659
  • 44114 Woodmont Dr, Leonardtown, MD 20650
    44114 Woodmont Dr, Leonardtown, MD 20650
    /2

    $615,000 Open House 5/24

    • 5 Beds
    • 3.5 Baths
    • 3,635 Sq Ft

    44114 Woodmont Dr, Leonardtown, MD 20650

    NO SHOWINGS UNTILL THE OPEN HOUSE MAY 24, SAT 11-2. PHOTOS WILL BE IN THE WEEK BEFOREGorgeous 5-bedroom home with 3.5 baths on 2 acres . All five bedrooms are conveniently located on the upper level. The main floor features a versatile flex den/office, a formal dining room, a parlor, and an open-concept kitchen and family room. The stunning kitchen features a center island with an eat-at counter,

    Lori Jean Buongiovanni (Hethmon) RE/MAX Realty Group

    44114 Woodmont Dr, Leonardtown, MD 20650
  • 41998 Pleasant Valley Ct, Hollywood, MD 20636
    41998 Pleasant Valley Ct, Hollywood, MD 20636
    41998 Pleasant Valley Ct, Hollywood, MD 20636
    /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
  • 42190 Ridge Rd, Mechanicsville, MD 20659
    42190 Ridge Rd, Mechanicsville, MD 20659
    42190 Ridge Rd, Mechanicsville, MD 20659
    /33

    $340,000

    • 3 Beds
    • 1 Bath
    • 1,134 Sq Ft

    42190 Ridge Rd, Mechanicsville, MD 20659

    Updated and cute as a button. Situated on a corner lot with a nice big yard, a shade tree and view of the woods across the street. This home has a new roof, vinyl plank flooring, appliances and HVAC. Freshly painted 3 bedrooms (one without a closet) living room, kitchen and bath. There's also a laundry room with storage space. The shed has electric and plenty of parking in the driveway.

    Trish Wallmark RE/MAX One

    42190 Ridge Rd, Mechanicsville, MD 20659
  • 27175 Cleveland St, Mechanicsville, MD 20659
    27175 Cleveland St, Mechanicsville, MD 20659
    27175 Cleveland St, Mechanicsville, MD 20659
    /14

    $189,000

    • 2 Beds
    • 1 Bath
    • 984 Sq Ft

    27175 Cleveland St, Mechanicsville, MD 20659

    Situated on two combined lots totaling nearly half an acre, this charming 2 bed 1 bath fixer-upper presents a unique opportunity for investors or DIY enthusiasts! Constructed with durable cinder block walls and featuring slab-on-grade construction beneath laminate flooring, this home offers a solid foundation for your vision. The cozy interior includes ceiling heights of 6'9" in the main living

    Katherine Dean RE/MAX One

    27175 Cleveland St, Mechanicsville, MD 20659
  • 11800 Point Lookout Rd, Scotland, MD 20687
    11800 Point Lookout Rd, Scotland, MD 20687
    11800 Point Lookout Rd, Scotland, MD 20687
    /7

    $50,000

    • Land
    • 0.87 Acre
    • $57,471 per Acre

    11800 Point Lookout Rd, Scotland, MD 20687

    Check out this lot in Scotland just around the corner from the Point Lookout State Park. Use it to build a house, garage, or park your camper or boat. Views of one of Scotland's beloved farms in the back and woods in the front. Existing structure is not livable

    Trish Wallmark RE/MAX One

    11800 Point Lookout Rd, Scotland, MD 20687
  • 44889 Mallard Place, Callaway, MD 20620
    44889 Mallard Place, Callaway, MD 20620
    44889 Mallard Place, Callaway, MD 20620
    /37

    $469,900

    • 4 Beds
    • 3 Baths
    • 2,154 Sq Ft

    44889 Mallard Place, Callaway, MD 20620

    Welcome to this stunning home in Callaway, Maryland, located in a cul-de-sac. This spacious 4-bedroom home offers an open floor plan filled with natural light and tons of character. The lower level features large bay windows that flood the living area with sunshine, creating a bright and inviting space for gatherings or quiet relaxation.The luxurious primary suite includes a beautiful primary

    Jesieryl Hartzer CENTURY 21 New Millennium

    44889 Mallard Place, Callaway, MD 20620
  • 41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    /93

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft

    41402 Silver Charm Ct, Leonardtown, MD 20650

    Welcome to your new home -- this stunning Colonial with 5 bedrooms, 3 full bathrooms and 1 half bathroom, 3300+ square feet and a finished basement are move in ready! New carpet has been installed and the entire house has been painted and pressure washed. Brand new Hardie plank fiber cement siding in deep ocean blue was installed in 2019. As you enter the grand foyer, wood floors lead you

    Kelly Padgett CENTURY 21 New Millennium

    41402 Silver Charm Ct, Leonardtown, MD 20650
  • 23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    /27

    $425,750

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft

    23730 Hicks Dr, Leonardtown, MD 20650

    Welcome to 23730 Hicks Drive – a charming, move-in ready rambler with room to grow! This beautifully updated 3-bedroom, 2-bath home sits on a spacious half-acre lot and features a walk-out basement, newer roof, windows, siding, gutters, and furnace. Inside, you’ll find brand new LVP flooring, recessed lighting in the kitchen, living room, and basement, and abundant natural light throughout.The

    Kimberlee Randall Group EXP Realty, LLC

    23730 Hicks Dr, Leonardtown, MD 20650
  • 42544 Anne Ct, Hollywood, MD 20636
    42544 Anne Ct, Hollywood, MD 20636
    42544 Anne Ct, Hollywood, MD 20636
    /33

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    42544 Anne Ct, Hollywood, MD 20636

    Discover the potential of 42544 Anne Ct, a solid brick home nestled in the desirable Hollywood, MD community. Featuring 3 bedrooms and 2 bathrooms plus living and entertaining spaces upstairs and down, this home offers a flexible layout perfect for a variety of lifestyles. Enjoy stainless steel appliances, an attached 2-car garage, and upper and lower decks for relaxing or entertaining. With a

    William Rabbitt The Southside Group Real Estate

    42544 Anne Ct, Hollywood, MD 20636
  • 23687 Coventry Dr, Leonardtown, MD 20650
    23687 Coventry Dr, Leonardtown, MD 20650
    23687 Coventry Dr, Leonardtown, MD 20650
    /58

    $665,000

    • 6 Beds
    • 4.5 Baths
    • 4,650 Sq Ft

    23687 Coventry Dr, Leonardtown, MD 20650

    Significant Price Adjustment – Now Priced Below Market Value!Seize the opportunity to make this stunning, move-in-ready 6-bedroom, 4.5-bath home your own. Situated on a prime corner lot in the sought-after Leonard's Grant community, this home offers over 5,500 square feet of beautifully finished space designed for comfort, entertaining, and everyday living.Highlights include a Gourmet Kitchen

    Lesa Clark Redfin Corp

    23687 Coventry Dr, Leonardtown, MD 20650
  • 23266 Clarks Rest Rd, Leonardtown, MD 20650
    23266 Clarks Rest Rd, Leonardtown, MD 20650
    23266 Clarks Rest Rd, Leonardtown, MD 20650
    /31

    $675,000

    • 4 Beds
    • 3.5 Baths
    • 3,858 Sq Ft

    23266 Clarks Rest Rd, Leonardtown, MD 20650

    This gorgeous Pinehurst model in Clark's Rest community is not going to last long! This home has 4BR/3.5BA located on large corner home site, Open floor plan, with upgraded Kitchen appliances and gas cook-top and granite counter tops. Hardwood flooring throughout , upgraded lighting with recessed lighting in the kitchen, large walk-in Pantry, freshly painted walls, separate formal dining room,

    Kelly Padgett CENTURY 21 New Millennium

    23266 Clarks Rest Rd, Leonardtown, MD 20650
  • 23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    23445 Grovewood Ct, Leonardtown, MD 20650
    /61

    $435,000

    • 3 Beds
    • 3.5 Baths
    • 2,379 Sq Ft

    23445 Grovewood Ct, Leonardtown, MD 20650

    Welcome to 23445 Grovewood Court, an exquisitely maintained residence in the esteemed Clark's Rest community, where sophistication and serenity converge. This splendid 3-bedroom, 3.5-bath townhome offers an elevated living experience, combining impeccable design with unparalleled comfort. Step inside to discover an expansive and luminous open-concept floor plan, enhanced by refined finishes and

    John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
  • 41998 Pleasant Valley Ct, Hollywood, MD 20636
    41998 Pleasant Valley Ct, Hollywood, MD 20636
    41998 Pleasant Valley Ct, Hollywood, MD 20636
    /59

    $1,100,000

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

    41998 Pleasant Valley Ct, Hollywood, MD 20636

    Welcome to 41998 Pleasant Valley Dr! This stunning one-level rambler is situated on 17 acres of serene land, offering the perfect blend of comfort and luxury. Enjoy spacious living with a 2-car attached garage and beautiful views of a peaceful pond. The open concept floor plan features a large living room with vaulted ceilings and a cozy gas fireplace, perfect for relaxation. Step outside to a

    Deanna Havenner CENTURY 21 New Millennium

    41998 Pleasant Valley Ct, Hollywood, MD 20636
  • 27149 Barton St, Mechanicsville, MD 20659
    27149 Barton St, Mechanicsville, MD 20659
    27149 Barton St, Mechanicsville, MD 20659
    /53

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    27149 Barton St, Mechanicsville, MD 20659

    Discover the perfect blend of charm and modern updates in this beautifully renovated home situated on a spacious double lot. All major renovations completed just 5 years ago! Roof, siding, heat pump, water heater, porch, kitchen, bathrooms, etc. Enter the door to a cozy screened in porch… perfect for peaceful mornings! Head in the main door to an entryway and family room with vinyl wood flooring

    Cheryl Bare CENTURY 21 New Millennium

    27149 Barton St, Mechanicsville, MD 20659
  • 23273 Nicholson St, Hollywood, MD 20636
    23273 Nicholson St, Hollywood, MD 20636
    23273 Nicholson St, Hollywood, MD 20636
    /54

    $699,999

    • 4 Beds
    • 4 Baths
    • 4,124 Sq Ft

    23273 Nicholson St, Hollywood, MD 20636

    Motivated sellers are offering up to $10k in closing costs to a qualified buyer with a full price offer. This stunning home offers 4 bedrooms with multiple walk-in closets, 4 full baths, and a partially finished basement. Recent updates include fresh paint, a new roof in April 2025, new garage doors April 2025, high efficiency HVAC upgrades on lower level in 2023 and the upper level in 2018.

    Mary Helen Wiley Daly RE/MAX One

    23273 Nicholson St, Hollywood, MD 20636
  • 43088 Island View, Hollywood, MD 20636
    43088 Island View, Hollywood, MD 20636
    43088 Island View, Hollywood, MD 20636
    /78

    $679,900

    • 3 Beds
    • 2 Baths
    • 1,372 Sq Ft

    43088 Island View, Hollywood, MD 20636

    WATERFRONT - WAITING FOR YOU! Completely Renovated Home - New Roof, New Well, New Windows, New HVAC, New Water Heater, New Attic Insulation, New doors, siding, and gutters, New Kitchen and Appliances with Quartz Countertops, New Bathrooms with porcelain, New paint throughout, refinished hardwood floors, new paved driveway, new exterior steps to the waters edge and so much more. Sit on the

    Donna Lacey CENTURY 21 New Millennium

    43088 Island View, Hollywood, MD 20636
  • 21684 Potomac View Dr, Leonardtown, MD 20650
    21684 Potomac View Dr, Leonardtown, MD 20650
    21684 Potomac View Dr, Leonardtown, MD 20650
    /25

    $490,000

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    21684 Potomac View Dr, Leonardtown, MD 20650

    3BR, 2Bath rancher with Front and Rear covered porches. Rear yard is ready for outdoor entertainment. Large side load garage with storage area over. Living Room with fireplace, dining area, open kitchen. No mandatory HOA, however the civic association is an optional fee.HVAC replaced a year ago.

    Terry Tenney Atlantic Southern Realty INC

    21684 Potomac View Dr, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 3

Maryland Leonardtown Leonardtown Middle School

Real Estate & Homes for Sale near Leonardtown Middle School

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

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