Leonardtown MD Real Estate & Homes for Sale

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Beds:
5
Baths:
4.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
MDSM2028266
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality. The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your morning coffee in peace. The main-level primary suite features a sitting area and a large bathroom with dual vanities, offering a private retreat from the rest of the home. Upstairs, you’ll find a versatile loft area and three generously sized bedrooms. The fully finished basement adds even more living space, complete with a large rec room and an additional bedroom and unfinished storage. Enjoy all the amenities Leonard’s Grant has to offer, just steps away from the community pool, tennis courts, and more!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,920
Status:
Active
MLS#:
MDSM2027998
Type:
Single Family-Detached
Subdivision:
Redgate
Lot size:
1.25 Acres
Year built:
1997
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Classic Private Colonial offers the perfect blend of tranquility and convenience, nestled on a generous 1.25-acre lot that backs to mature trees for ultimate shade and privacy. Outdoor Living: Enjoy entertaining or quiet mornings on the large vinyl deck, overlooking a great yard. The circular paved driveway provides easy access and added convenience. The Home: Featuring a traditional layout, you can enter through the covered front porch or the attached 2-car garage that features plenty of built-in shelves. The main level is designed for living with a family room, kitchen, a separate dining room, and a cozy living room with a gas fireplace. A half bath on the main level adds convenience. Primary Suite: Retreat to the primary bedroom, boasting a high ceiling, a walk-in closet, and an attached primary bathroom. This spa-like space features double sinks, a separate shower stall, and a soaking tub with a gorgeous picture window offering serene nature views. Worry-Free Ownership: Major components are taken care of with a new Roof installed in 2025, a conditioned crawlspace with a dehumidifier, and some freshly painted walls. The property also includes a shed for extra storage and, best of all, NO HOA, NO front-foot fee, and NO deferred water/sewer bill! Prime Location: Located in the desirable Wilderness Woods Neighborhood (Redgate), you are in the most popular and sought-after city of Historic Leonardtown. Enjoy close proximity to NAVAIR Pax River Base, shopping, museums, restaurants, hospital, music venues, historic places, boat ramps, marinas, fishing piers, a winery, watersport rentals, and SO MUCH more! Don't delay, schedule a tour today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,888
Status:
Active
MLS#:
MDSM2027792
Type:
Single Family-Detached
Subdivision:
Meadows At Town Run
Lot size:
0.25 Acres
Year built:
2019
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite features a large walk-in closet and a luxury bathroom featuring a soaking tub, huge shower, and two vanities featuring gorgeous decorative tile. The kitchen and family room on the main floor offer a large welcoming space for family and friends with a sliding glass door that goes out to the patio to enjoy the firepit and fenced in back yard. The additional dining room and living room spaces allow you to spread out for large family gatherings. The mudroom joins the garage and is a great space to welcome you home. The basement has a finished studio room for your crafts or hobbies and a large unfinished area for you finish and make it your own.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,527
Status:
Active
MLS#:
MDSM2027122
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.28 Acres
Year built:
1970
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family room with wood stove insert, large laundry room, and accessory area on the lower level. Also has a 2 Car Detached garage built in 2008. Roof of garage and house was re-shingled in 2020 with 50 year shingles. The HVAC was regularly serviced.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,291
Status:
Active
MLS#:
MDSM2027316
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.55 Acres
Year built:
2018
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,291 sq. ft. of comfortable living space, 4 bedrooms, and 2.5 bathrooms, perfectly situated on a .55-acre lot in Leonardtown. Inside, you’ll find a bright and spacious layout designed for both everyday living and entertaining. The heart of the home features an eat-in kitchen with stainless steel appliances, a center island, and plenty of natural light, opening to a warm and welcoming family room. Step right out onto the deck off the kitchen, ideal for morning coffee, grilling, or hosting gatherings that flow easily into the fenced backyard. Upstairs, the generously sized bedrooms include a relaxing primary suite, while the additional bedrooms offer flexibility for family, guests, or a home office. With its combination of classic Colonial style, modern updates, and an outdoor space ready for fun and relaxation, this home provides the perfect setting to make lasting memories. Located close to schools, shopping, dining, and all the charm of Leonardtown, it’s ready to welcome its next owner.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,018
Status:
Active
MLS#:
MDSM2027780
Type:
Single Family-Detached
Subdivision:
Brubachers
Lot size:
0.18 Acres
Year built:
1950
Courtesy: RE/MAX One 410-535-6291
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ADDITIONAL INFORMATION

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 crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiast’s paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include: ? Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide ? Seawall refurbished in 2020 for added shoreline protection ? Private pier with an electric boat lift—perfect for boating adventures Don’t miss this rare chance to own a piece of paradise with endless potential. Whether you’re looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,308
Status:
Active
MLS#:
MDSM2027022
Type:
Single Family-Detached
Subdivision:
Clark's Rest
Lot size:
0.15 Acres
Year built:
2024
Courtesy: RE/MAX Realty Group 301-843-5100
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ADDITIONAL INFORMATION

Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage includes an EV charger for your convenience. Step through the front door into a two-story foyer, where natural light floods the space and sets the tone for an elegant yet welcoming home. To your right, the formal living room offers a perfect place for quiet gatherings, while the formal dining room to your left is ideal for hosting holidays and dinner parties. Continue into the heart of the home is an open-concept family room with a cozy fireplace, seamlessly connected to the morning room and a truly spectacular gourmet kitchen. At the center is an impressive long kitchen island, offering abundant seating and serving as the perfect gathering space for family and guests alike. surrounding it, you'll find 42" upgraded cabinetry, quartz countertops, a stylish tile backsplash, stainless steel appliances, gas stove, and a generous walk-in pantry- a chef's dream and an entertainer's delight. Tucked away on the main level, you'll also find a private library perfect for a home office, a flex room ideal as a playroom or guest space, and a convenient separate laundry room just steps from the garage. Upstairs, the oversized primary suite is a true retreat. Unwind in the spa-like en suite bath, complete with dual walk-in closets, a 5x5 tile shower with dual showerheads, a soaking tub, dual vanities, and a private water closet. Three additional bedrooms offer ample space for family, and guests, one includes its own private full bath, while the other two share a beautifully appointed hall bath. The unfinished walkout basement offers tall windows and a 3-piece bathroom rough-in, giving you a blank canvas to create even more living space tailored to your needs. Whether it's a home gym, media room, or guest suite, the possibilities are endless. Outside, enjoy the level backyard-perfect for play, pets, or outdoor entertaining. Throughout the home, you'll find luxury vinyl plank flooring, upgraded lighting, and ceiling fans, adding style and comfort to every room. This is more than a house-it's a place to live, grow, and make lasting memories. Come see why life in Clark's Rest, with community amenities including a pool, clubhouse, and walking trails, is the perfect place to call home.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,026
Status:
Active
MLS#:
MDSM2026838
Type:
Single Family-Detached
Subdivision:
St Marys
Lot size:
2.02 Acres
Year built:
1961
Courtesy: Keller Williams Legacy 443-660-9229
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ADDITIONAL INFORMATION

A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some well-deserved TLC. This single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space and is situated on a 2.02-acre lot. This home also includes a detached garage with space for two vehicles. For investors, the property's sizable lot and ranch-style design may offer potential for renovation or expansion. The absence of a homeowner’s association (HOA) could also provide additional flexibility for property modifications. Nearby schools include Piney Point Elementary School, Leonardtown Middle School, and Leonardtown High School.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,472
Status:
Active
MLS#:
MDSM2027150
Type:
Single Family-Detached
Subdivision:
Kingston
Lot size:
1.02 Acres
Year built:
2004
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has a bright and cheery interior with four spacious bedrooms on the upper level. Generous closets. Convenient upper level laundry. The main floor features an oversized great room, a kitchen with solid surface counters, and a garden window over the kitchen sink to grow fresh herbs. A front sitting room makes for a sizable home office, opposite a formal DR. The unfinished basement has a full walkout and a finished 3-piece full bath. Enjoy the outdoors, whether on the back deck and patio, the traditional front porch, or garden and play on the 1+ acre lawn. No rear neighbors, this property backs to a conservation area. Kingston is situated off beautiful Medley's Neck Rd., flanked by vast farms. It is a community in which everyone enjoys decorating for the seasons! Kids have plenty of room to play at the neighborhood soccer field and baseball diamond, complete with a great picnic pavilion, tables and grill for group gatherings. Located just minutes from thriving Leonardtown, Easy commute to NAS Pax River.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,526
Status:
Active
MLS#:
MDSM2027750
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.38 Acres
Year built:
2003
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

?? Seller is offering a $4,000 concession with an accepted full-price offer! Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees and plenty of open yard space. Inside, the two-story foyer opens to a main level with newer flooring, real hardwood floors in the living room, and fresh paint throughout the home. A flexible room with French doors at the front of the house works perfectly as a home office or formal dining room. The eat-in kitchen features granite countertops, a tile backsplash, stainless GE appliances, a Kraus sink, center island, and a spacious pantry. It opens directly to a cozy family room with a wood-burning fireplace—great for gathering. Upstairs, you’ll find four generously sized bedrooms. The primary suite offers wooded views, a soaking tub, dual sinks, walk-in shower, and a large linen closet. Three additional bedrooms and a second full bathroom complete the upstairs. The fully finished walkout basement adds even more versatility with a fifth bedroom, full bath, wet bar, laundry area, and a fantastic flex room ideal for a gym, playroom, office, or media space. Outdoor living is another highlight. Enjoy the composite screened deck that overlooks a private backyard backing to a Forest Conservation Area. A small fenced section is perfect for pets, and the property includes two great sheds—one heated and cooled, ideal for hobbies or studio use, and a 20'×24' Amish-built structure with electric and lofts for storage or a workshop. Lovingly maintained by its original owners, the home also includes valuable big-ticket updates such as two high-efficiency HVAC systems (2023 & 2025), an architectural roof (2018), a rebuilt driveway, whole-home filtration system, sump pump with backup, chimney improvements, and updated bath fixtures. With more than 3,500 sq ft of finished space and a welcoming, flexible layout, this home offers comfort, privacy, and long-term value—just minutes to historic Leonardtown, dining, shopping, and an easy commute to PAX River Naval Base. You’ll feel right at home the moment you arrive. Come and take a look!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,040
Status:
Active
MLS#:
MDSM2027068
Type:
Single Family-Detached
Subdivision:
Chappelears
Lot size:
0.34 Acres
Year built:
2005
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream come true for boaters and anglers alike. Inside, you’ll find a spacious and inviting layout filled with natural light throughout. The highlight of the home is the Florida room with panoramic river views, offering the perfect spot to relax, entertain, or simply take in stunning sunsets over the water. The open loft adds flexible living space—ideal for a guest area, office, or hobby room. The kitchen and dining areas flow seamlessly for easy living, while two comfortable bedrooms provide restful retreats. With 2.5 baths, convenience is never in short supply. An oversized 3-car garage provides ample storage for your vehicles, water toys, tools, and more—making it easy to enjoy every aspect of the riverfront lifestyle. Whether you’re searching for a weekend getaway or a year-round residence, this home blends comfort, charm, and direct river access. Enjoy peaceful mornings, afternoons on the water, and evenings watching the river roll by—all from the comfort of your own home. Don’t miss this rare opportunity to own a piece of Potomac River paradise!

Beds:
3
Baths:
4.00
Sq.Ft.:
3,683
Status:
Active
MLS#:
MDSM2027714
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
3.39 Acres
Year built:
1991
Courtesy: RE/MAX One 410-535-6291
View additional info

ADDITIONAL INFORMATION

Discover this stunning cedar siding contemporary waterfront home offering a perfect blend of comfort and character. Enjoy water access with a private shared dock, ideal for relaxing days on the water. Freshly painted throughout with brand-new flooring in basement and two bedrooms, this home shines inside and out. The sunroom features beautiful slate floors and peaceful views of the surrounding landscape. The living room boasts soaring ceilings, a brick fireplace, while the dining room showcases hardwood floors. The primary bedroom includes a private full bath for added convenience. Additional highlights include a mudroom, 2-car garage, and fully finished basement. Experience the beauty of waterfront living in this one-of-a-kind home—don’t miss it!

Beds:
3
Baths:
1.00
Sq.Ft.:
924
Status:
Active
MLS#:
MDSM2024652
Type:
Single Family
Subdivision:
None Available
Lot size:
1 Acres
Year built:
1999
Courtesy: Home Towne Real Estate 301-862-4000
View additional info

ADDITIONAL INFORMATION

Presenting an opportunity for creative redevelopment: a level lot equipped with a septic system and a driveway easement, along with a trailer that has microbiological growth. The property will require the removal of the existing trailer, with the option to proceed with new construction or secure a trailer replacement. Qualified buyers looking to customize and reimagine the site are encouraged to inquire.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,824
Status:
Active
MLS#:
MDSM2024888
Type:
Single Family-Detached
Subdivision:
Clark's Rest Phase 2
Lot size:
0.25 Acres
Year built:
2020
Courtesy: RE/MAX Realty Group 301-884-9493
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ADDITIONAL INFORMATION

Main Level living at its finest in the heart of Leonardtown! Customized Lusby model built in 2020 situated on a spacious corner lot in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which transfers to the new homeowner. VA assumable loan available (to veteran only) at 2.75%. This exquisite home boasts an open floorplan that flows effortlessly. The generous-sized kitchen features 42 inch cabinetry along with space for floating shelves, upgraded granite counter tops, center island, coffee bar, walk in pantry with transom window, stainless steel appliances, and a formal dining area adjoined with the kitchen. The family room is off the kitchen for great entertaining and has a walk out to the rear covered patio, sun deck, and an additional patio all overlooking the fully fenced rear yard. The primary suite has its own access to the rear covered porch, along with a walk in closet, and a luxury bath with a walk-in shower and dual sink vanity. There are two additional rooms and a hall bath on the main level as well. The lower level has a media room/rec room, storage rooms, and an expansive additional unfinished space with windows where you could have two additional bedrooms. The lower level is built with a rough-in for future full bath, as well. Additional attributes to this home are built-in Wi-Fi extenders, active security system, two car front load garage, premium corner lot, deep covered front porch, and a gazebo and firepit for relaxing and entertaining. 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 (Trolly pickup and drop off location just steps from the front door). 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! ***** Correction**** previous remarks stated a whole home generator hook up and there is not one in place but the garage has a dedicated GFI for the truck and refrigerator.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,040
Status:
Active
MLS#:
MDSM2025400
Type:
Single Family-Detached
Subdivision:
Chappelears
Lot size:
0.34 Acres
Year built:
2005
Courtesy: RE/MAX One 410-535-6291
View additional info

ADDITIONAL INFORMATION

Welcome to 40461 Old Breton Beach Road—a breathtaking waterfront retreat on the shores of the Potomac River in Leonardtown, Maryland. Nestled in one of Southern Maryland’s most scenic and peaceful communities, this coastal-style home offers the perfect blend of charm, functionality, and panoramic water views that will leave you speechless. Perfect for a primary or rental. From the moment you arrive, you'll be captivated by the stunning setting and relaxed elegance. Step inside to discover an open floor plan featuring wood floors, and an abundance of natural light that pours through large windows and the glass-enclosed porch—perfect for soaking in the serene river views all year long. The heart of the home is the beautifully appointed kitchen, complete with granite countertops, a center island, and views that make meal prep a joy. A cozy loft adds flexible living space, ideal for a home office, guest quarters, or a quiet reading nook. The oversized 3-car garage provides ample space for vehicles, tools, and water toys. Outside, the private pier with a boat lift makes launching your adventures on the Potomac effortless—whether you're into fishing, crabbing, kayaking, or sunset cruising. Located just minutes from historic Leonardtown, you’ll enjoy easy access to local shops, restaurants, and wineries, while still feeling worlds away in your private waterfront oasis. Whether you’re looking for a weekend getaway or a full-time escape, this home offers the ultimate waterfront lifestyle.

Beds:
5
Baths:
3.00
Sq.Ft.:
6,064
Status:
Active
MLS#:
MDSM2025006
Type:
Single Family-Detached
Subdivision:
Avenmar
Lot size:
3.18 Acres
Year built:
2002
Courtesy: RE/MAX One 410-535-6291
View additional info

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)

Beds:
5
Baths:
4.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
MDSM2025004
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality. The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your morning coffee in peace. The main-level primary suite features a sitting area and a large bathroom with dual vanities, offering a private retreat from the rest of the home. Upstairs, you’ll find a versatile loft area and three generously sized bedrooms. The fully finished basement adds even more living space, complete with a large rec room and an additional bedroom and unfinished storage. Enjoy all the amenities Leonard’s Grant has to offer, just steps away from the community pool, tennis courts, and more!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,412
Status:
Active
MLS#:
MDSM2024842
Type:
Single Family-Detached
Subdivision:
Chestnut Hills
Lot size:
4.1 Acres
Year built:
1996
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy on a beautifully treed 4 acre lot. The first floor features a private office/den, formal living room, and elegant dining room. The large kitchen includes a cozy breakfast nook and opens to a step-down family room with a slider leading to a screened-in porch—ideal for indoor-outdoor living. Upstairs, the expansive primary suite includes a full en suite bathroom, accompanied by three additional generously sized bedrooms and another full bath. Full basement to finish as you would like. New paint and carpet thru out. Roof replaced in 2018, geothermal replaced in 2012 and windows replaced in 2022, A long driveway leads to a 2-car garage, and the property includes two storage sheds—perfect for hobbies or extra space. Don't miss the opportunity to own this serene retreat in one of the area's most desirable neighborhoods!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,046
Status:
Active
MLS#:
MDSM2026396
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.21 Acres
Year built:
2010
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of Leonard's Grant community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field. Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches. Freshly painted with Sherwin Williams exuding coastal ambiance with creamy accents. Gorgeous new carpet throughout. The premium deep ocean blue exterior greets you as you walk into your oasis. Fenced backyard with endless possibilities. Enjoy your massive deck with so many options whether grilling, gazing at the stars, or enjoying the evening breeze with family and friends overlooking the twinkling yard lights. As an added bonus, put your feet up while your automatic sprinklers do the work for you. Walk to your elementary school and library. Don’t miss out on paradise! Check out this hidden gem you won’t be disappointed!

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
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)

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
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.

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
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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,834
Status:
Active
MLS#:
MDSM2023654
Type:
Single Family-Detached
Subdivision:
Herring Creek Estates
Lot size:
0.84 Acres
Year built:
1970
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!

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
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

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.

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
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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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

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.



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

    $510,000
    12.7%
    change since last quarter
  • # Active listings

    90
    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