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Leonardtown MD Real Estate & Homes for Sale

53 Properties Found

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$395,000

20161 Tower Hill Road Leonardtown, MD 20650

MLS: MDSM2023878 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,661
Status:
Active
MLS#:
MDSM2023878
Type:
Residential
Subdivision:
Tower Hill
Lot size:
3.32 Acres
Year built:
1990
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 410-535-6291
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ADDITIONAL INFORMATION

This contemporary cape cod style home is it's own private retreat on over 3 acres. The main floor gives you a formal living room with vaulted celing and 2 sided woodstove/fireplace while also providing an additional family room that could easily be converted to a 3rd bedroom. The kitchen has been updated with granite counter tops, subway tiled backsplash, new appliances and more. Dining room surrounded by windows to enjoy the view of the woods and a mud room with washer/dryer and ample storage. Upstairs you'll find 2 large bedrooms with a loft room in between accessing a 2nd level deck. Full bathrooms on each floor, the upper one remodeled to give a spa like feel. Plan your summer parties with the 9600 gallon heated pool, hot tub, and screened gazebo on extensive decking. Shed also included for additional storage. Community has a lake that is an easy walk from the house.

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$519,000

23433 Grovewood Court Leonardtown, MD 20650

MLS: MDSM2023900 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
2,804
Status:
Active
MLS#:
MDSM2023900
Type:
Residential
Subdivision:
Clark's Rest
Lot size:
0.08 Acres
Year built:
2022
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX Realty Group 301-884-9493
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ADDITIONAL INFORMATION

Stunning Townhome in Clarks Rest Community. *OPEN HOUSE* Saturday, May 3rd from 11-2. Welcome to this beautifully maintained, "nearly-new" end-unit townhome in the desirable Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views. The chef-inspired kitchen is a dream, showcasing granite countertops, a designer tile backsplash, 42" cabinetry with modern pulls, and a separate coffee bar station. You'll also enjoy the convenience of a pantry and separate appliance closet, as well as a breakfast bar, table space, disposer, built-in microwave, and recessed lighting. The stainless steel appliances complete the sleek, contemporary design. A sliding glass door leads to your rear deck with composite floor boards, offering a peaceful escape with beautiful nature views. The spacious family room, just off the kitchen, features recessed lighting, a ceiling fan, and windows providing natural light and serene views, making it the perfect spot for relaxation and gatherings. Also on the main level, you will find a formal Dining Room and Living Room. Upstairs, you'll find three generously-sized bedrooms, two full bathrooms, and the laundry for added convenience. The owner's suite is a true retreat with a generous walk-in closet with custom closet system with built-in wardrobe featuring customized drawers, shelves and hanging rods. The luxurious spa-like bath features a large dual sink vanity, a separate soaking tub, and an expansive glass walk-in shower with beautiful ceramic tile. The lower level offers even more space, with a recreation room, an additional guest bedroom, a full bath, and a walkout to your two-car garage. A bonus feature of this home is the extra large storage closets on all three levels! Elevator Ready Home: Home includes three vertically stacked closets on each floor (3X5) lined directly above one another. This space is currently used for storage but is there for future installation of a residential elevator. This home is just under three years old and comes with the peace of mind of a Builder's 2-10 Warranty that's valid for an additional seven years. Clarks Rest residents enjoy a range of community amenities, including the community pool, a baby/toddler pool, sports courts (basketball and tennis), a beautiful clubhouse, walking nature trails, playgrounds, and open green spaces for relaxation and play. Experience the best of Leonardtown living with the seasonal Leonardtown Trolley. Hop on right from your neighborhood sidewalk and enjoy the ride around town with stops at the local winery, restaurants, pubs, coffee shops, charming bakeries, and of course, the Leonardtown Wharf. Spend your free time at nearby parks, beaches, museums, boardwalks, and theaters. Located just a short drive from Patuxent Naval Air Station (PAX), this home also offers access to excellent Leonardtown schools: Leonardtown High, Leonardtown Middle, and Leonardtown Elementary. Clarks Rest is a "walkable" community providing sidewalks throughout that also lead to the charming downtown with many stops along the way, including the library, schools, parks, and more. Love where you live here in Leonardtown, a most convenient place! VA Assumable Loan at 4.75% (Veteran Only with Eligibility Certificate)

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$785,000

40801 Kiskadee Lane Leonardtown, MD 20650

MLS: MDSM2023638 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
6,064
Status:
Active
MLS#:
MDSM2023638
Type:
Residential
Subdivision:
Avenmar
Lot size:
3.18 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 410-535-6291
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ADDITIONAL INFORMATION

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, giving you over 6.5 acres of tranquil privacy and future investment potential. (Seller prefers to sell together) As you enter this elegant home, you are immediately welcomed by the soaring ceilings and abundant natural light of the two-story family room, creating an open and inviting atmosphere. The gourmet kitchen is a chef’s delight, featuring rich cherry cabinetry, granite countertops, custom serving station and desk area, and newer stainless steel appliances — all designed for both everyday living and effortless entertaining. The formal dining room comfortably accommodates a table for 12 and includes space for a hutch and serving buffet, perfect for hosting holidays and gatherings. Adjacent, a formal living room leads seamlessly into a bright and airy sunroom, ideal for morning coffee or afternoon reading. A unique highlight of the main level is a bonus bedroom or office tucked beside a full bath — perfect for guests, multi-generational living, or working from home. Upstairs, retreat to your luxurious primary suite, a true sanctuary featuring a large private sitting room, two walk-in closets, and an expansive spa-inspired ensuite bath with dual vanities, soaking tub, and walk-in shower. Three additional bedrooms and a full bath complete the upper level. The fully finished lower level offers flexible space for entertaining, hobbies, or guest quarters, and includes a large storage area and separate workshop. Outside, the stunning landscaping and private wooded setting offer peaceful views and a sense of serenity, all while being just steps away from Avenmar’s unmatched amenities — water access, community pool, clubhouse, equestrian facilities, and more. Set back on a private lane, this property combines the best of luxury, privacy, and community living. Don’t miss this rare opportunity to own a legacy home with additional land in one of Southern Maryland’s most coveted neighborhoods. *Whole house generator * Irrigation system *Easy Maintenance Trex Deck (2022)

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$659,900

41430 Challedon Way Leonardtown, MD 20650

MLS: MDSM2023910 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
MDSM2023910
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

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 level features a primary suite with a private bath, hardwood floors, a cozy family room with gas fireplace, and a flexible living room that doubles as a home office. Upstairs offers a large loft area and three generously sized bedrooms, perfect for family or guests. The fully finished basement adds even more living space, including a 5th bedroom, full bathroom, rec room, media room, and two large storage rooms. Outdoor living is just as inviting, with a covered front porch, brick patio, and concrete patio for relaxing or entertaining. This energy-efficient home is equipped with solar panels, helping keep electric bills low. Plus, you’ll love the unbeatable location—steps from community amenities and minutes to everything Leonardtown has to offer.

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$574,000

23075 Hollywood Road Leonardtown, MD 20650

MLS: MDSM2023778 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
3,238
Status:
Active
MLS#:
MDSM2023778
Type:
Residential
Subdivision:
None Available
Lot size:
0.5 Acres
Year built:
1942
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Built in 1942, this 5-bedroom, 2.5-bath home offers over 3,200 square feet of character-filled living space Original hardwood floors, arched openings, detailed trim work, and vintage glass door knobs are just a few of the timeless details that give this home its warmth and soul—while updates like a newer heating system, domestic hot water, roof, and refreshed bathrooms bring you everyday comfort. With natural light in all the right places highlighting the home’s spacious layout and warm, welcoming feel. A deep front porch sets the tone for quiet mornings, while the fenced backyard and two-car garage—with workshop space—add function to match the charm. And with coffee shops, restaurants, and Leonardtown Wharf just blocks away, it offers a walkable lifestyle. Lovingly cared for by just two families since it was built, this home is ready for its third chapter.

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$649,999

41430 Whimsical Court Leonardtown, MD 20650

MLS: MDSM2023560 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,907
Status:
Active
MLS#:
MDSM2023560
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.2 Acres
Year built:
2011
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Realty Navigator 443-256-3773
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ADDITIONAL INFORMATION

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 living, or anyone seeking flexible, functional space. Step inside to find a warm, welcoming layout , a spacious eat-in kitchen, and a cozy family room ideal for relaxing or entertaining. One of the standout features is the highly desirable first-floor large primary suite with an en-suite bath and ample closet space. Upstairs, you’ll find three large additional bedrooms with ample closet space and a full bath. The fully finished basement is a true bonus, offering even more living space with a fifth bedroom, full bathroom, and a custom theatre room—perfect for movie nights, game days, or casual entertaining. Additional highlights include: 3.5 well-appointed bathrooms First-floor laundry Two-car garage with additional driveway parking Spacious backyard with room to relax, play, or entertain Located in a friendly, established neighborhood with top-rated schools, parks, and easy access to shopping, dining, and Pax River Naval Base Captain Walter Francis Duke Elementary School This home checks all the boxes—space, location, and versatile living options. Don’t miss your opportunity to make it yours!

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$615,000

20540 Deer Wood Park Drive Leonardtown, MD 20650

MLS: MDSM2023400 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,850
Status:
Active
MLS#:
MDSM2023400
Type:
Residential
Subdivision:
Chestnut Hills
Lot size:
2.22 Acres
Year built:
1995
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

Welcome to this beautiful contemporary colonial situated on over two private acres in the desirable community of Chestnut Hills. As you step inside, you will be greeted by three fully finished levels of warmth and comfort to include a soaring great room with walls of windows and a main level office. This thoughtfully designed home has been meticulously maintained and offers four generously sized bedrooms on the upper level, three and a half baths and a fabulous fully finished lower level that could be used as an in-law suite or a fantastic entertaining space for guests or children! The light filled main level offers a formal living and dining room and large gourmet kitchen that flows seamlessly into the great room with a gas fireplace. The open chef's kitchen has stainless steel appliances, a large island and oversized cabinetry-perfect for family gatherings! And for those upcoming spring nights, enjoy the sights and sounds of nature while dining on your private deck situated right off the dining room! The spacious primary suite features a large walk-in closet and an updated ensuite bathroom with an inviting soaking tub and separate shower. The fully finished basement boasts marble flooring, a delightful kitchen with granite countertops, a bonus room that could be used for a home gym, bedroom or playroom, an extra storage room and access to a wooded , private backyard oasis! Roof was replaced in 2019 and home has 3 seperate HVAC units 2 of which were replaced in 2020 and 2018, hot water heater replaced in 2022. Enjoy the wonderful community amenities to include a large playing field, wooded trails and a beautiful gazebo- all in time for summer!

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$599,900

23578 Pine Bluff Way Leonardtown, MD 20650

MLS: MDSM2023102 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
3,188
Status:
Active
MLS#:
MDSM2023102
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.18 Acres
Year built:
2011
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

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 COUNTERS, GAS FIREPLACE, 9' CEILINGS, FENCED BACKYARD, COVERED FRONT PORCH, STAMPLED CONCRETE PATIO....JUST BEAUTIFUL. NEW CARPET AND PAINT IS COMING APRIL 1ST. STILL TIME FOR YOU TO CHOOSE YOUR COLORS!!!!

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$649,900

23275 Jenifer Court Leonardtown, MD 20650

MLS: MDSM2023552 Photos
Beds:
6
Baths:
5.00
Sq.Ft.:
6,311
Status:
Active
MLS#:
MDSM2023552
Type:
Residential
Subdivision:
Estates At Singletree
Lot size:
0.34 Acres
Year built:
2005
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

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 filled with natural light and gas fireplace, a formal dining room, and two dedicated home offices. The heart of the home is the gourmet kitchen, complete with 42-inch white cabinetry, granite countertops, and stainless steel appliances—perfectly positioned off the family room for effortless flow. The spacious primary suite is also located on the main level and includes a luxurious en-suite bath. A mudroom with laundry hookups sits just off the garage for added convenience. Upstairs, you’ll find four generously sized bedrooms and two full bathrooms, including a Jack-and-Jill bath ideal for families. The fully finished lower level is a dream retreat with a home theater, large second primary suite, gym, a second laundry area, and a charming wine closet tucked beneath the stairs. Situated on a .34-acre lot in a quiet cul-de-sac, this exceptional property offers the perfect blend of privacy and accessibility—just moments from shops, restaurants, and local events downtown.

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$699,900

18937 Hodges Lane Leonardtown, MD 20650

MLS: MDSM2023654 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,834
Status:
Active
MLS#:
MDSM2023654
Type:
Residential
Subdivision:
Herring Creek Estates
Lot size:
0.84 Acres
Year built:
1970
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-609-9000
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ADDITIONAL INFORMATION

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 just relax and enjoy life. Come and check it out!

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$699,900

41402 Silver Charm Court Leonardtown, MD 20650

MLS: MDSM2023568 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,046
Status:
Active
MLS#:
MDSM2023568
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.21 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

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 through the main level which includes an office with glass doors, formal dining room, great room w/gas fireplace, and gourmet kitchen. The kitchen has granite counters, island with bar style seating, upgraded cabinets, gas cooktop, wall ovens, and built in microwave. This floor plan is perfect for entertaining and gatherings or hosting events. The breakfast nook has sliders leading out to the back deck and fully fenced back yard. Sit, relax and enjoy a beverage as you fire up your grill this Spring and Summer. The primary bedroom has plenty of space to create your own private retreat and a walk in closet. The primary bathroom has tile floors, soaking tub, deluxe shower and dual vanities. Three additional bedrooms, a full bathroom, and laundry room complete the top level of this home. And if that's not enough there is more....the finished basement with rec room, theatre room and additional storage will blow you away. Walk out access to the back yard from the basement. Two car garage with garage openers. Community amenities include a swimming pool, tennis/basketball courts, sidewalks and open space for activities. Close to schools, shopping, restaurants and area amenities. Enjoy downtown Leonardtown's town square, yearly activities and the scenic waterfront wharf. Schedule your online appointment today.

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$599,999

42279 Bird Haven Drive Leonardtown, MD 20650

MLS: MDSM2023598 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,139
Status:
Active
MLS#:
MDSM2023598
Type:
Residential
Subdivision:
Kingston
Lot size:
1.05 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Beautiful home located in the desirable Leonardtown neighborhood of Kingston, this home features 5 bedrooms and 3.5 Baths . The main level features a large kitchen with granite counter tops and stainless steel appliances, spacious family room with wood burning fireplace, a home office with built-in storage, and formal dining room. The primary suite located on the second level features a large walk-in closet and primary bath has a large soaking tub and separate vanities. The basement has a wet bar, large flex area , and a fifth bedroom and full bath . The unfinished portion of the basement is perfect for storage . Walkout the basement to your private backyard surrounded by trees. There is plenty of space to entertain including a patio, deck, garden area, and large shed. Community space with pavilion. Roof was replaced in 2023 and HVAC in 2022. Enjoy the benefits of a quiet neighborhood setting while still being minutes to all that Downtown Leonardtown has to offer.

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$425,750

23730 Hicks Drive Leonardtown, MD 20650

MLS: MDSM2023542 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,992
Status:
Active
MLS#:
MDSM2023542
Type:
Residential
Subdivision:
Holly Oaks
Lot size:
0.6 Acres
Year built:
1975
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: EXP Realty, LLC 833-335-7433
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ADDITIONAL INFORMATION

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 updated kitchen boasts quartz countertops, a tiled backsplash, center island, and a gas range—perfect for home chefs. A front-load washer and dryer are also included. Ceiling fans offer added comfort, and a U-shaped/circle driveway provides plenty of parking. With no HOA, there's flexibility to add a detached garage, pool, or screened porch—bring YOUR vision! ***VA assumable loan at a 4.75% interest rate available for qualified buyers! Additionally, this home is located in a USDA-eligible area, offering potential for 100% financing.*** Only 30 minutes from PAX River Naval Base and Solomons Island, where you can enjoy boating, jet skiing, and waterfront dining at favorites like The Island Hideaway, Clarke’s Landing, and The Pier. Outdoor lovers will also appreciate nearby St. Mary’s River State Park. Enjoy peaceful country living with modern updates and exciting possibilities—schedule your showing today!

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$305,000

20483 White Point Road Leonardtown, MD 20650

MLS: MDSM2023508 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
1,160
Status:
Active
MLS#:
MDSM2023508
Type:
Residential
Subdivision:
None Available
Lot size:
1 Acres
Year built:
1953
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Welcome to 20483 White Point Road! Nestled on a beautiful 1-acre lot in Leonardtown, this charming 3-bedroom, 1-bath cottage-style rambler offers the perfect blend of comfort and character. Built in 1953, the home features a cozy, single-level layout that’s easy to maintain and full of potential. Enjoy peaceful country living surrounded by nature, all while being just a short drive to the heart of Leonardtown, shopping, and waterfront attractions. Whether you're looking for a starter home, a weekend retreat, or a place to make your own, this property is a wonderful opportunity you won’t want to miss!

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$950,000

21940 Maranatha Way Leonardtown, MD 20650

MLS: MDSM2023512 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
2,814
Status:
Active
MLS#:
MDSM2023512
Type:
Residential
Subdivision:
None Available
Lot size:
1.75 Acres
Year built:
1993
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: JPAR Real Estate Professionals 301-684-4895
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ADDITIONAL INFORMATION

Beautifully maintained and thoughtfully updated, this 3-bedroom, 2.5-bathroom rambler with a separate 1-bedroom, 1-bathroom apartment above the garage offers the perfect combination of comfort, style, and stunning waterfront living. Conveniently located on a private road, enjoy peaceful privacy while being just minutes from shops, dining, and all that Leonardtown has to offer. Inside the main house, you'll find a spacious layout designed for both relaxation and entertaining. The open living room flows into a bright and airy sunroom filled with natural light and breathtaking water views. The kitchen is a chef’s dream, featuring abundant cabinetry, a large island, and a nice-sized pantry. The primary bedroom is a true retreat, featuring a spacious walk-in closet and a beautifully updated en suite bath with tile flooring, a granite-topped vanity, and a walk-in tile shower. Two additional bedrooms share an updated full bath, while an updated half bath is conveniently located for guests. A dedicated home office at the front of the house provides a quiet space for remote work or study. Step outside to enjoy two expansive composite decks, one off the dining area and another directly accessible from the primary bedroom, both overlooking serene water views. The private 56-ft pier features a 22x16-ft platform at the end and is equipped with a 10,000 lb boat lift. Nice deep water, the current owner has comfortably kept a 35-ft boat in the slip at the end of the pier, making it easy to enjoy time on the water at a moment's notice. The level yard offers plenty of space for recreation, gardening, or simply soaking in the peaceful surroundings. A storage shed provides additional convenience for outdoor tools and gear. Above the oversized, conditioned garage, the separate apartment is perfect for guests, potential rental income, or extended family. It includes a full kitchen, generous living space, a large bedroom, and a private balcony with spectacular water views. Recent updates include: new driveway, garage door, two composite decks (2020), hallway full bath, half bath and new sliding doors throughout the home (2021), new carpet, hot water heater, gas fireplace, downstairs blinds, apartment dishwasher & range, and oil fired water heater/back up heat (2022), upstairs blinds and new washer and dryer (2023), and a new cold water tank (2024). This property has been well-loved and meticulously cared for over the years, and it truly shows. Schedule an appointment today to see for yourself!

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$625,000

23259 Jenifer Court Leonardtown, MD 20650

MLS: MDSM2023516 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,078
Status:
Active
MLS#:
MDSM2023516
Type:
Residential
Subdivision:
Estates At Singletree
Lot size:
0.31 Acres
Year built:
2005
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Rory S. Coakley Realty, Inc. 301-340-8700
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ADDITIONAL INFORMATION

DRIVE BY AT NIGHT TO SEE ALL THE EXTERIOR LIGHTING AROUND THE HOME. Stunning 5BR/3.5BA colonial with stone accents and two-car garage located in Estates at Singletree. This model features an open floor plan spanning approximately 4,000 square feet on three levels and offers a great sense of light and spaciousness with 9-foot. ceilings and floor-to-ceiling windows on the main level. Designer décor with custom painting; elaborate three-piece chair rail, crown, and shadow box molding; luxury vinyl wide-plank flooring on the main level; custom window treatments, upgraded and recessed lighting, surround sound, and brushed nickel door hardware and hinges throughout. Gourmet kitchen with granite countertops, tile backsplash, and oversized granite center island/breakfast bar. Remodeled bathrooms throughout with ceramic tile flooring and tub/shower wall surround.  Private resort-like outdoor space with exterior lighting throughout, two-level composite and vinyl deck, pergola, two brick paver patios, firepit, putting green, custom outdoor bar structure with granite countertops and shed-like storage area, and outdoor speakers. Professional landscaping features custom hardscape, specimen trees, ornamental shrubs, and uplighting to complete your slice of paradise.  Inviting entryway with front door, upper & side transom windows, and storm door leading to two-story foyer; glass French door entry to study/music room with ceiling fan; living room with recessed lighting and floor-to ceiling bay window; dining room with recessed lighting, double window, and chandelier; gourmet kitchen with 42-inch raised-panel cabinets with under cabinet lighting, granite countertops, designer tile backsplash, upgraded Samsung stainless appliances, oversized granite center island/breakfast bar, desk/workstation, recessed lighting, and pantry closet; breakfast area with chandelier and glass slider to private backyard oasis; family room off of kitchen with a wall of windows, recessed lighting, and a floor-to-ceiling stone fireplace with electric insert; main level laundry area off of garage and powder room with ceramic tile flooring, vanity and wainscotting; hardwood staircase to upper level landing with two closets; primary bedroom suite with tray ceiling, private sitting area, massive walk-in closet with custom shelving; primary bath with double-door entry, designer ceramic tile flooring, vanity with dual undermount sinks, quartz countertops, linen closet, two-person Jacuzzi whirlpool tub with ceramic tile tub deck, and separate walk-in ceramic tiled shower with glass enclosure; three additional bedrooms on this same level with double-door closets and ceiling fans; remodeled hall bathroom with wood-like tile flooring, vanity with quartz countertops and dual sinks, upgraded lighting and bath fixtures, and tub/shower with tile surround and frameless glass enclosure.  Fully-finished walk-out lower-level recreation room/game room with carpet and ceramic tile, wet bar with cherry cabinets and two under counter beverage centers, recessed lighting, storage closet under stairs; bedroom with full window, and ceiling fan; remodeled full bathroom with walk-in shower; den with double-door entry, recessed lighting, and custom built-in shelving; BONUS movie theater/media room with surround sound pre-wiring. The Estates at Singletree is approximately one mile to quaint downtown Leonardtown to enjoy restaurants, bakeries, coffee shops, and live music on the square. The Library, Elementary School, and Senior Center are all nearby.  Or head down to Breton Bay and Leonardtown Wharf to enjoy the park, playground, fishing, free boat dock, ice cream, and gorgeous sunsets. **Family Pool memberships are available at the nearby Breton Bay Country Club.

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$665,000

23687 Coventry Drive Leonardtown, MD 20650

MLS: MDSM2023524 Photos
Beds:
6
Baths:
5.00
Sq.Ft.:
4,650
Status:
Active
MLS#:
MDSM2023524
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.27 Acres
Year built:
2012
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Seize the opportunity to make this stunning, move-in-ready 6-bedroom, 4.5-bath home your own! Nestled on a prime corner lot in the sought-after Leonard's Grant community, this home offers over 5500 square feet of luxurious living space and an impressive list of features. From the gourmet kitchen to the fully finished home theater, every inch of this home is designed for comfort, convenience, and entertainment. Whether you're relaxing in the sunroom, enjoying the patio with a fire pit, or hosting friends in the massive recreation room with a wet bar, this home is perfect for those who love to entertain. The enormous Gourmet Kitchen, with an attached Butler's Pantry and Breakfast Room, features beautiful granite countertops, an oversized island, gas cooking, double ovens, under-cabinet and pendant lighting, and plenty of cabinet space! The Main Floor Master Bedroom offers privacy and has access to a private balcony overlooking the community pond. It also features double walk-in closets. The spacious Master Bath includes separate sinks, a vanity, a jetted tub, an oversized shower with a bench, and a private toilet room. The main floor also includes a large Living Room with a gas fireplace, a formal Dining Room, a main-floor Laundry Room, and a heated & cooled Sunroom. The Sunroom, with 7 windows that can be opened to enjoy the breeze in any weather, is perfect for reading, crafting, dining, or relaxing with friends! The upper level offers a second set of laundry hookups, 2 full bathrooms, multiple linen closets, and 4 additional bedrooms—flexible enough to be used as a Game/Play Room, Home Office, or Guest/Nanny/In-Law Suite. The lower level is an entertainer’s dream, featuring a gigantic Recreation Room with a wet bar and built-in mini fridge. There’s plenty of space for a large workout area and multiple storage spaces (one with extra dedicated electrical). The fully finished Home Theater is an absolute highlight, with a 106-inch screen, projection system, and surround sound. The walk-out lower level leads to concrete patios and provides access to the 18x14 wood/workshop area and yard storage, complete with extra electrical for power tools. The attached 2-car garage includes the home’s central vacuum system, a laundry tub, storage shelving, and a dedicated 220V outlet, ideal for a home charging station for your electric vehicle. This corner-lot home also includes a spacious patio with a fire pit, alarm system, and security cameras, ensuring comfort and peace of mind. There’s even an additional concrete parking pad for extra vehicles. Located in the highly desirable Leonard's Grant community, you're just down the street from the community pool, clubhouse, sports courts, playgrounds, and parks. The new Leonardtown Library is nearby, and the home is only a short commute to Pax River NAS, with shopping and entertainment just minutes away. The home has been freshly painted throughout and is move-in ready! The neighborhood has a community feel like no other, with terrific neighbors who truly make this a special place to live. Don’t miss out—call to schedule your showing today!

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$675,000

23266 Clarks Rest Road Leonardtown, MD 20650

MLS: MDSM2022494 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,858
Status:
Active
MLS#:
MDSM2022494
Type:
Residential
Subdivision:
Clark's Rest Phase 1
Lot size:
0.27 Acres
Year built:
2016
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

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, with crown molding. There is a additional room off of the family room that could be used for a office or den .Owner's Suite has large walk in closets, soaking tub, upgraded tile and double vanities. All of the bedroom's are very spacious. The basement has finished rec room and full bath, a large work out room, with additional other rooms for storage, there is a 2 car garage with openers, Magnificent sunsets from your front porch , Community offers an outdoor pool, side walks, walking trails, playground, short walk to Leonardtown for fun shopping and dining.

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$435,000

23445 Grovewood Court Leonardtown, MD 20650

MLS: MDSM2023446 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
2,379
Status:
Active
MLS#:
MDSM2023446
Type:
Residential
Subdivision:
Clark's Rest
Lot size:
0.05 Acres
Year built:
2022
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

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 thoughtful craftsmanship throughout. Each bedroom provides an oasis of tranquility and privacy, while the elegant primary suite ensures a sanctuary of rest. The fully finished lower level—complete with a luxurious full bath—offers versatile space, ideal for guests, a home office, or an entertainment suite. Enjoy access to an array of exceptional amenities, including a sparkling swimming pool, inviting playground, tennis courts, and a stately community center, all tailored for both leisure and lively gatherings. Beyond the confines of this exclusive neighborhood, you'll find a world of refined conveniences: renowned restaurants, chic shopping, serene parks, and more—all just moments away. Downtown Leonardtown is just a short drive away, where history and modern charm beautifully collide. Stroll through the picturesque streets and immerse yourself in the town's rich heritage, with historic buildings, quaint shops, and inviting local eateries. Savor delectable meals at acclaimed restaurants, explore unique boutiques, and take in the art galleries that lend an air of sophistication to the town. With the added benefit of being mere minutes from Naval Air Station Patuxent River, this residence offers a coveted blend of luxury and location. Seize the opportunity to experience the finest in community living—schedule your private showing today.

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$599,900

41403 Heritage Lane Leonardtown, MD 20650

MLS: MDSM2023344 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,340
Status:
Active
MLS#:
MDSM2023344
Type:
Residential
Subdivision:
Clark's Rest Phase 1
Lot size:
0.18 Acres
Year built:
2016
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

This beautiful home, situated on a desirable corner lot, exudes warmth and timeless charm. Hardwood flooring greets you upon entry, complemented by crown molding, chair rail accents, and recessed wall niches, all adding to the home’s classic appeal. The formal dining room, highlighted by stately columns and a tray ceiling, provides a sophisticated space for gatherings. The island kitchen features granite countertops, a tile backsplash, built-in microwave, recessed lighting, and a pantry. The adjacent family room stands out with a coffered ceiling and decorative columns, enhancing the home’s inviting atmosphere. The spacious owner’s suite includes a sitting area, tray ceiling, two walk-in closets, and a luxurious bath with a soaking tub and separate shower. The secondary bedrooms are well-sized, with one offering a walk-in closet. The fully finished basement adds valuable living space, including a fourth bedroom—equipped with surround sound and perfect for a media room or other uses—a full bathroom, and recreational room with a wet bar rough-in. The side-entry garage features a two-foot extension and an extended driveway for additional convenience. Enjoy outdoor living on the covered front porch or the composite deck, complete with a gazebo—perfect for relaxing or entertaining. The fenced-in backyard provides privacy and includes a storage shed for added convenience. The property also includes an in-ground irrigation system for easy lawn maintenance. Residents of Clark’s Rest enjoy access to community amenities such as a clubhouse, swimming pool, playground, sidewalks, and jogging trails. Conveniently located near local services, schools, shopping, and recreational options, this home is a must-see! Schedule your private showing today!

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$499,900

22158 Monterey Place Leonardtown, MD 20650

MLS: MDSM2023316 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,782
Status:
Active
MLS#:
MDSM2023316
Type:
Residential
Subdivision:
Breton Bay Estates
Lot size:
0.61 Acres
Year built:
1975
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: PAX Real Estate 410-535-3332
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ADDITIONAL INFORMATION

Rarely do you have this kind of water view from every room in the home. Enjoy waking to vacation type views everyday....This home has a unique design that affords itself to many buyers. Pride of ownership abounds. Many recent improvements, including windows and doors. Roof replaced approx. 5 years ago. Home shows very well. Come see this home quickly so you can make this your new home. Located off the 16th hole of Breton Bay Golf course; allows sports enthusiasts and those wanting beautiful Lake view vistas a view to love...Special home with a premier location.

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$405,000

40449 Breton View Drive Leonardtown, MD 20650

MLS: MDSM2023244 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
2,288
Status:
Active
MLS#:
MDSM2023244
Type:
Residential
Subdivision:
Breton Bay Pud
Lot size:
0.06 Acres
Year built:
1995
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Experience the serene lifestyle of Breton Bay, where charm and convenience come together! Just steps away from the Breton Bay Country Club—offering pool, tennis, and golf amenities—and a short drive to the historic downtown Leonardtown for dining, shopping, and local events, this townhome is your ideal retreat. This captivating 3-level, three-bedroom, 3.5-bath townhome features vinyl flooring throughout the main level. The bright living and dining areas flow together, complemented by a stylish kitchen outfitted with modern stainless steel appliances. Gather around the cozy gas-burning fireplace that adds a warm touch to the living space. Retreat to the master suite, which includes a soaking tub, a spacious double vanity, and a separate shower—providing the perfect escape after a long day. The lower level boasts an additional bedroom and a full bathroom, making it perfect for guests or extended family. Step outside to enjoy the outdoor patio, a wonderful space for hosting gatherings or simply relaxing in the fresh air.

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$685,000

23558 Belmar Drive Leonardtown, MD 20650

MLS: MDSM2023238 Photos
Beds:
6
Baths:
4.00
Sq.Ft.:
4,267
Status:
Active
MLS#:
MDSM2023238
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.2 Acres
Year built:
2008
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Beautiful house in the desired neighborhood of Leonard’s Grand in Leonardtown! This house has many unique characteristics! All new carpet! As you walk in to the hardwood entryway, you’ll notice the gorgeous staircase. This level includes a dining room, custom butler’s pantry and a large, upgraded kitchen. The transom windows are gorgeous and bring in a ton of natural light. These cabinets are an absolute beautiful wood! The island is large and the eat in kitchen can easily fit a 6 to 8 person table. Off of the great room , with very high ceilings, is the main level primary suite. The bedroom has two walk-in closets and a gorgeous tiled bathroom. The bathroom has custom sinks, a claw bathtub and also includes an enormous shower. Upstairs you’ll find three nice sized bedrooms and another full bathroom. The basement has so much to offer! The luxury vinyl planks cover the entire basement floor. The fifth bedroom in the basement has an en suite bathroom. The sixth bedroom is any kid’s dream! There are four built in, twin size bunkbeds. Off of this room is another great room equipped with a fireplace. The laundry is also in the basement along with some unfinished storage. I would also be remiss if I did not mention the mud room with custom built-ins right off of the garage. Come see you this unique Leonard’s grant house today!

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$660,000

23598 Belmar Drive Leonardtown, MD 20650

MLS: MDSM2023240 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,758
Status:
Active
MLS#:
MDSM2023240
Type:
Residential
Subdivision:
Leonards Grant
Lot size:
0.29 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to this beautifully upgraded 5-bedroom, 3.5-bathroom home, perfectly situated on one of the best lots in the neighborhood! Backing to trees for added privacy, this home offers both elegance and functionality. Step inside to find refinished hardwood floors throughout the main level, adding warmth and sophistication. The gourmet kitchen features sleek quartz countertops, a new backsplash, and an open-concept layout that flows seamlessly into the great room—perfect for entertaining. A large dining room provides ample space for gatherings. Upstairs, the primary suite is a true retreat with an oversized bedroom, huge walk-in closet, and a spa-like ensuite featuring dual vanities, a corner soaking tub, and a large shower. Four additional bedrooms offer plenty of space for family, guests, or a home office. The finished basement is built for entertainment, complete with a wet bar, built-in features, and plenty of space to host guests. Step outside to enjoy the composite deck, which leads down to a custom patio with a fire pit and built-in cocktail table—ideal for relaxing evenings. Don’t miss this opportunity to own a home in Leonard’s Grant with incredible outdoor space, premium upgrades, and newly refinished wood floors!

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$490,000

21684 Potomac View Drive Leonardtown, MD 20650

MLS: MDSM2023184 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,504
Status:
Active
MLS#:
MDSM2023184
Type:
Residential
Subdivision:
Breton Bay Estates
Lot size:
0.46 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Atlantic Southern Realty INC 301-475-8575
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ADDITIONAL INFORMATION

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.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Leonardtown 20650 Real Estate

Leonardtown is located in Maryland. Leonardtown, Maryland 20650has a population of 4,445. Leonardtown 20650 is more family-centric than the surrounding county with 40.08% of the households containing married families with children. The county average for households married with children is 35.05%.

The median household income in Leonardtown, Maryland 20650 is $126,472. The median household income for the surrounding county is $102,859 compared to the national median of $69,021. The median age of people living in Leonardtown 20650 is 32.3 years.

Leonardtown Weather

The average high temperature in July is 87.8 degrees, with an average low temperature in January of 28.4 degrees. The average rainfall is approximately 45.5 inches per year, with 14.3 inches of snow per year.

Leonardtown Map

Leonardtown Real Estate Market Conditions

  • Median sales price

    N/A

  • # Active listings

    75
    30-day change

Leonardtown Schools and Demographics

Education near Leonardtown, MD

City County
High School Graduates 86.69 91.67
College Degree - 2 year 4.14 7.83
College Degree - 4 year 43.83 33.03
Graduate Degree 20.41 11.79
Expenditures per Student 15,242 15,242
Students per Teacher 15.9 15.9

Elementary Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Benjamin Banneker Elementary School PK - 05 683 15 20656
Chesapeake Charter School KG - 08 360 14.1 20653
Dynard Elementary School PK - 05 478 19.2 20621
Evergreen Elementary School PK - 05 795 19.3 20619
George Washington Carver Elementary School PK - 05 644 17 20634
Green Holly Elementary School PK - 05 602 14.6 20653
Greenview Knolls Elementary School PK - 05 408 17.9 20634
Hollywood Elementary School PK - 05 550 18.2 20636
Leonardtown Elementary School PK - 05 789 18.6 20650
Lettie Marshall Dent Elementary School PK - 05 648 19.9 20659
Lexington Park Elementary School PK - 05 540 17.6 20653
Mechanicsville Elementary School PK - 05 384 21.4 20659
Oakville Elementary School PK - 05 304 17.9 20659
Park Hall Elementary School PK - 05 670 17.7 20667
Piney Point Elementary School PK - 05 529 18.7 20690
Ridge Elementary School PK - 05 285 16.5 20680
Town Creek Elementary School KG - 05 234 14.2 20653
White Marsh Elementary School KG - 05 244 16.9 20659

Middle Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Esperanza Middle School 06 - 08 818 16 20653
Leonardtown Middle School 06 - 08 933 15.9 20650
Margaret Brent Middle School 06 - 08 992 17.4 20659
Spring Ridge Middle School 06 - 08 989 16.6 20653

High Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Chopticon High School 09 - 12 1,628 21.6 20660
Great Mills High School 09 - 12 1,549 17.8 20634
Leonardtown High School 09 - 12 1,831 20.8 20650

Ungraded Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Dr. James A. Forrest Career and Technology Center UG - UG 0 0 20650
St. Mary's County Evening High UG - UG 0 20650

Demographics near Leonardtown, MD 20650

Zip Code City
Neighborhood Type Small town
Population 4,445 113,209
Population Density 1,169 316
Median Age 32.3 36.7
People per Household 2.8 2.8
Median Household Income 126,472 102,859
Average Income per Capita 41,923 44,208

Real estate near Leonardtown

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