Leonardtown MD Real Estate & Homes for Sale

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Beds:
5
Baths:
4.00
Sq.Ft.:
3,260
Status:
NEW LISTING
MLS#:
MDSM2031206
Type:
Single Family-Detached
Subdivision:
Academy Hills
Lot size:
0.25 Acres
Year built:
2006
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Classic Elegance in the Heart of Sought-After Leonardtown! Nestled at the end of a quiet cul-de-sac in the desirable Academy Hills community, this stunning 5-bedroom, 3.5-bath Colonial offers nearly 4,000 square feet of beautifully finished living space surrounded by peaceful wooded views and open pastureland. Step outside to enjoy the private, fenced backyard featuring split-rail fencing, a spacious composite deck with vinyl railings, and a patio perfect for entertaining or relaxing in a serene setting. Inside, the traditional floor plan is both timeless and functional, highlighted by a grand two-story foyer, formal living and dining rooms, and a spacious eat-in kitchen with open sightlines into the inviting family room. Upstairs, you’ll find four generously sized bedrooms, two full baths, and a conveniently located laundry room. The sun-filled primary suite is a true retreat, featuring vaulted ceilings, a custom walk-in closet system, and a luxurious en-suite bath complete with dual vanities, a newly updated shower, and a soaking tub. The fully finished walk-out basement offers exceptional versatility and previously served as an in-law suite. Complete with a private bedroom and full bath, French doors leading to the patio, separate stackable washer/dryer hookup, propane line for an additional fireplace, and abundant storage space with added shelving, it’s ideal for extended family, guests, or multi-generational living. This home has been thoughtfully updated with numerous improvements, including a new roof, newly renovated primary bathroom, new refrigerator and dishwasher, washer and dryer, updated second-floor bathroom vanity, new flooring in the basement bathroom, and a new HVAC system for the second floor installed in 2022. Fresh interior paint adds a bright, move-in-ready feel throughout. Conveniently located within walking distance to historic downtown Leonardtown and just 25 minutes to NAS Patuxent River, this home perfectly blends timeless charm, modern updates, and an unbeatable location.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,161
Status:
NEW LISTING
MLS#:
MDSM2030902
Type:
Single Family-Detached
Subdivision:
X
Lot size:
0.45 Acres
Year built:
1961
Courtesy: CENTURY 21 New Millennium 410-266-9005
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ADDITIONAL INFORMATION

The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the MLS. You may use the disclosure language below in lieu of the MLS task requirements issued through RESNET. Disclosure language must be entered in the Agent Private Remarks. If spacing is an issue, you may attach an Offer Instruction document to the MLS along with the First Look Notice of Interest document. No offers will be reviewed unless a buyer has submitted a First Look Notice to you. At a minimum, the first 3 sentences below as italicized should be entered to the Agent Private Remarks section of the MLS with further instruction to read the offer instructions attached in the MLS document section. An Offer Instruction document is attached for your convenience. If using this document insert the Seller’s name per the listing letter and add the RESNET offer fee and offer link from the RESNET MLS tasks prior to loading the document to the MLS. Charming and beautifully updated brick rancher located in the heart of Leonardtown! This single-level home offers 3 bedrooms and 1.5 bathrooms, making it ideal for easy, comfortable living. Recently remodeled, the property features fresh updates throughout, blending classic charm with modern touches. Enjoy a spacious, level lot perfect for outdoor entertaining, gardening, or simply relaxing. The solid brick construction provides timeless curb appeal and durability, while the interior improvements make this home move-in ready. Conveniently located near local shopping, dining, and amenities, this is a great opportunity to own a well maintained home in a desirable area. Don’t miss it!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,571
Status:
NEW LISTING
MLS#:
MDSM2031226
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! Homesite 157 Madison D1: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with white kitchen cabinets, Quartz countertops, subway tile backsplash, black fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard, perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,688
Status:
NEW LISTING
MLS#:
MDSM2031024
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.52 Acres
Year built:
1986
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

This property represents the definition of "Pride of Ownership" and their move is bittersweet. To have everything they have built here is remarkable and you could be the lucky one to obtain this property. Everything has been taken care of like it was purchased yesterday, books and invoices for most included, with comfort and convenience in mind. From the blacktop driveway, manicured lawn, to the 2 car over sized (32'x28') detached garage, to the over sized "boat" (32'x26') garage with water and in floor drain and a man cave area above it, this property was built with a plan of ease of use. If it would make life easier & more comfortable (ie. O/S grills propane piped), it has been done. The kitchen has top of the line stainless appliances. Double wall oven, propane cook top, backsplash, and corian counter tops with plenty of cabinets. Main hall bath has ceramic flooring tub/shower, and vanity. Owners suite includes a double closet with organizer and owners bath with walkin shower. The "lower level" (basement does not fit the name for this property), has an egress window that may slow a very inexpensive option for another bedroom and consists of a walkout with no steps, large entertaining area, full bath with walkin shower, washer & dryer, and utility/mechanical area. Some of the upgrades to the property are: yard irrigation system, new roof (3-4 years old), entire house humidifier/de-humidifer, motion lights on house and garages, weather station with inside display, solar light on flagpole, gutter guards, sunsetter shade on back deck sliding door, gazebo with outside curtains to keep the sun out or the heat in for year round use, area for wood stove that now has a free standing propane stove, wall fans in boat garage, and a 12'x20' shed w/loft. All of this and a home generator as well to keep it all running.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,019
Status:
Active
MLS#:
MDSM2031452
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.48 Acres
Year built:
1965
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome home to the sought after community of Breton Bay in Leonardtown, where thoughtful updates, flexible living space, and an unbeatable location come together beautifully. This property offers the rare opportunity to enjoy all that Breton Bay has to offer, while still benefiting from no HOA restrictions. For a minimal optional annual fee, residents can enjoy private beach access at two separate waterfront locations, perfect for kayaking, relaxing by the water, swimming, or taking in the peaceful Bay lifestyle. Just in time for summer, the Breton Bay Golf Course, pool, tennis courts, and country club memberships are also available separately. Be sure to stop by the clubhouse, open to the public, for dinner, cocktails, or a casual dining experience after your showing. Inside, you are welcomed by a lovely entry leading into a spacious living room and formal dining area. The cozy kitchen offers rear deck access overlooking the fenced backyard, creating an easy flow for entertaining, outdoor dining, or everyday enjoyment. Upstairs, you will find a comfortable hall bathroom, two secondary bedrooms, and a primary suite complete with its own small private bath. The lower level offers additional flexibility with a full bathroom, additional bedroom, and a large family room. Continue through to the unfinished laundry area with direct garage access and an additional unfinished storage space offering plenty of room for organization and future possibilities. As an added bonus, the chicken coop and chickens can optionally convey with the property if desired. Ample parking and proximity to Leonardtown attractions offer easy living at its best.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,169
Status:
Active
MLS#:
MDSM2031394
Type:
Single Family-Detached
Subdivision:
The Woods At Bayside
Lot size:
0.46 Acres
Year built:
1997
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

***TEMP OFF WHILE REVIEWING OFFERS*** Welcome home! If you need space to spread out, this unique and cozy home on a quiet half-acre lot is just what you've been looking for. Two separate living areas means enjoying movies and gaming in one room while you enjoy peace in the other. This one-of-a-kind floor plan maximizes every square foot, and surprisingly roomier than it appears! With 5 bedrooms, 2 full and 1half bathrooms, there is plenty of personal space for a growing family, multi-generational living, a home office, or hobbies. The perfect blend of rural quiet and everyday functionality. Come take a look and see how this unique space fits your lifestyle!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,300
Status:
Active
MLS#:
MDSM2030700
Type:
Single Family-Detached
Subdivision:
Clearfields Of Breton Bay
Year built:
2003
Courtesy: Century 21 Redwood Realty 301-208-2288
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ADDITIONAL INFORMATION

Beautiful 4 bedroom, 2 1/2 bathroom colonial located in Leonardtown. Just mins from downtown Leonardtown amenities, shopping, restaurants, schools and more. This home has hardwood floors throughout. Spacious formal living and dining rooms. Kitchen with lots of cabinets and island with seating. Breakfast area and sliding doors that open to the back yard and patio. Family room w/gas fireplace off kitchen. The second level has an owners suite with walk in closet. Owners bathroom complete with soaking tub, separate and dual vanities. 3 additional bedrooms and a full bathroom complete the top floor. Unfinished basement w/laundry area. Back yard is flat with plenty of room to spread out and enjoy outdoor activities. Gazebo and firepit are perfect for summer entertaining. Schedule your online appointment today.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,910
Status:
Active
MLS#:
MDSM2031384
Type:
Single Family-Detached
Subdivision:
Leonardtown
Lot size:
0.36 Acres
Year built:
2004
Courtesy: Long & Foster Real Estate, Inc. 410-535-1000
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ADDITIONAL INFORMATION

Brick-front one-level rambler featuring 3 bedrooms, 2 full bathrooms, and over 1,900 finished square feet. A welcoming covered front porch leads to an open and spacious interior with hardwood flooring throughout the foyer, hallway, living room, and formal dining room. The living room features a gas fireplace, while the dining room offers cathedral ceilings and Palladian windows for abundant natural light. The kitchen opens to the living area and includes a breakfast area, center island, recessed lighting, built-in microwave, and new luxury vinyl plank flooring. The primary suite features a walk-in closet and an ensuite bathroom with dual vanities, a soaking tub, and a separate shower. All bedrooms have new carpeting, and the interior has been freshly painted throughout. Both bathrooms have been updated with new ceramic tile flooring, toilets, and light fixtures. Additional highlights include a laundry room conveniently located off the kitchen and garage, plus an oversized attached 2-car garage with a utility sink and side-yard access. Ideally located just minutes from Downtown Leonardtown, Leonardtown Wharf, shopping, restaurants, MedStar St. Mary’s Hospital, and commuter routes to NAS Pax River. Enjoy nearby recreation and entertainment, including kayaking, paddle yoga, waterfront activities, and weekend concerts on the square.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,367
Status:
Active
MLS#:
MDSM2031298
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.35 Acres
Year built:
2012
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

With a great layout, tons of living space, popular location, well-ranked schools, community amenities, and a corner, fenced, cul-de-sac lot, this Leonard's Grant "Frederick" model has it all! A 2' rear bump out gives this 5-bedroom, 3.5 bath Colonial more than 4,300 sq. ft of comfortable living space. Wave hi to the neighbors from the welcoming front porch, and then enter the soaring two-story foyer with lots of natural light. To the right, adjoined formal living and dining rooms allow for gracious entertaining. To the left, French doors provide a quiet space for the home office/study. 9' ceilings and attractive engineered hardwood flooring grace the entire main floor. Follow the hall w/ decorative wainscot into the heart of the home... the open eat-in kitchen and family room. With all the upgrades, any chef will delight in this kitchen's gas range, large island, tall Maple cabinets w/ ample storage, Granite counters, pantry closet, and stainless appliances featuring a 1-year fridge and dishwasher. Informal dining at the breakfast bar or table area. Take your coffee out to the Breakfast/Sun Room and enjoy the morning's early light. The family room includes a propane fireplace for chilly nights, built-in speakers, and plenty of space for large gatherings around the big game. On nice days, head out to wrap-around paver patio, gather round a fire pit, fire up the grill or relax in a comfy seating area. Plenty of room to play in the big backyard, and the vinyl privacy fence is great for keeping kids and pets in view. Highlights in the Primary ensuite include a sitting room/fitness area w / skylight, cathedral ceiling, shiplap accent wall, huge walk-in closet and attached bath with walk-in tiled shower, tile-surround soaking tub, and double sinks. Three more good-size bedrooms upstairs. New washer in convenient 2nd-floor laundry, too. Elevated ceilings continue in the lower-level's 945 sq. ft of finished space. The interior steps land in a big game room w/ chalkboard wall, built-in playhouse, and rock-climbing wall. Gamers and movie buffs will love the surround-sound media room. A legal 5th bedroom and full bath make a great space for guests or teen. LL has unfinished storage, and extra wide walk-up stairs to backyard. Shelving and work bench in the high-ceiling garage. A powder room and mudroom add convenience to the main floor layout. Never run out of hot water with the newer tankless water heater, and take comfort from the recently redone air conditioning system. Just steps away from the community pool, playgrounds, tennis, basketball, rec fields and jogging paths, this well-maintained home is also only minutes from downtown Leonardtown, its wharf, and major commuter routes to points both north and south. Don't miss your opportunity to view this extraordinary home. Schedule your showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,554
Status:
Active
MLS#:
MDSM2031220
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

***** Hurry in! Secure your new home now and personalize it with your choice of interior colors. December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, brushed nickel fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard—perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,604
Status:
Active
MLS#:
MDSM2031072
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

***Estimated Late October Delivery****To Be Built*** Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full bath, perfect for a guest suite or home office. Upstairs, enjoy 9’ ceilings, luxury vinyl plank flooring, and an open-concept kitchen featuring 42" upgraded maple cabinets, upgraded granite countertops, a large center island, walk-in pantry, and stainless steel GE appliances. The kitchen flows seamlessly into the dining area and oversized family room, with access to a 14x12 maintenance-free deck overlooking your private, fenced-in backyard. The upper level boasts a spacious owner’s suite with tray ceiling, walk-in closet, and a luxurious ensuite bath with dual vanities and QBHI’s signature deluxe tiled shower. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the top floor. Additional features include: Oversized 1-car garage and 2-car wide driveway, finished and painted garage with drywall, smart home technology with IQ Pro command center, Skybell camera doorbell, and smart thermostat Low-maintenance exterior with stone-to-grade front (per elevation), sodded yard, vinyl fencing, and landscaping package. Community amenities include sidewalks, recreation center, pool, playground, pickleball, and tennis courts, all in the heart of charming Leonardtown. Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,095
Status:
Active
MLS#:
MDSM2030268
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.08 Acres
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

***TO BE BUILT*** ***Estimated Late November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The main level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your backyard—ideal for guests, a private office, or a second living space. The oversized one-car garage and wide driveway provide ample parking and storage options. Upstairs, you'll find 9’ ceilings, luxury vinyl plank flooring, and a beautifully appointed kitchen with 42” upgraded maple cabinetry, slide-out dovetail drawers, soft-close features, and granite countertops. The large center island, walk-in pantry, stainless steel GE appliances, and open-concept layout make this a true entertainer’s dream. The adjoining dining and family rooms lead out to a 14x12 maintenance-free deck overlooking your vinyl-fenced backyard. The upper level includes a luxurious owner’s suite with a tray ceiling, walk-in closet, and ensuite bath featuring dual vanities and QBHI’s signature deluxe tiled shower with bench, dual showerheads, and recessed lighting. Two additional bedrooms, a full hall bath, and a separate laundry room complete the top floor. Additional highlights include: finished and painted oversized garage, smart home technology with touchscreen IQ Pro command center, Skybell video doorbell, and smart thermostat, sodded and landscaped yard, stone-to-grade front (per elevation), concrete front porch, and seamless gutters, 6’ vinyl fenced backyard with gate. Community amenities include clubhouse, pool, playground, tennis courts, and pickleball courts. Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
5
Baths:
5.00
Sq.Ft.:
2,756
Status:
Active
MLS#:
MDSM2031286
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.36 Acres
Year built:
2007
Courtesy: Residential Plus Real Estate Services 301-934-9985
View additional info

ADDITIONAL INFORMATION

This 5 BR, 3 full BA, 2 half BA home offers nearly 3,000 square feet of comfortable living, but what truly sets it apart is everything beyond the main house. Step outside to your own backyard oasis featuring an in-ground saltwater pool, gazebo, and expansive entertaining space—perfect for summer gatherings or quiet evenings under the stars. Need room to grow, work, or host? The 28x40 detached garage with finished upper-level suite opens the door to endless possibilities—ideal for multi-generational living, guest quarters, home office, or turn into a recreation room w/wet bar. Set on 1.36 acres, this property offers the privacy and freedom you’ve been looking for, with space for hobbies, storage, or simply enjoying the outdoors—without the restrictions of an HOA. Located just minutes from Leonardtown and an easy commute to Naval Air Station Patuxent River, this home delivers the perfect balance of convenience and seclusion. If you’ve been searching for a property that offers more than just a house—something with versatility, function, and lifestyle built in—this is it.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,144
Status:
Active
MLS#:
MDSM2031060
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.92 Acres
Year built:
1960
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot. This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been thoughtfully updated with a brand new roof, new windows, new flooring throughout, a fully renovated kitchen with new appliances, and beautifully updated bathrooms, new water heater providing both style and peace of mind. Additional improvements include a new HVAC system to be installed, ensuring comfort and efficiency for the new owner. Enjoy easy single-level living with plenty of outdoor space, ideal for relaxing, entertaining, or future expansion. No HOA. Conveniently located near Leonardtown amenities, shopping, dining, and schools.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,726
Status:
Active
MLS#:
MDSM2031224
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.18 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome Home! This beautifully maintained home in Leonard's Grant backs up to trees, a rainwater pond and lots of wildlife! Enjoy watching the deer, bunnies and squirrels in the privacy of your fenced in back yard and large deck. The home features 4 spacious bedrooms, 3.5 baths, a finished basement, new (2022) luxury vinyl plank flooring throughout all levels, new energy efficient sliders (2022), build in custom Amish built bookshelves (2022). The primary bedroom features a walk-in custom-built closet, and a primary bath with large shower. A new roof was put on in 2024. The kitchen has an abundance of large, warm brown cabinets, a pantry cabinet, granite countertops, and stainless appliances. The details in this house are amazing, columns separating the dining room from the kitchen and the built-in bookcase in the living room make this home special. The open floor plan of the bumped-out kitchen, large breakfast area and spacious family room is amazing, roomy, and yet cozy. This house is never ending in its charm, character and spaciousness. Make it yours!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,340
Status:
Active
MLS#:
MDSM2030894
Type:
Single Family-Detached
Subdivision:
Kingston Estates
Lot size:
0.73 Acres
Year built:
2004
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to 42032 Starlight Drive in Leonardtown, MD, a spacious and beautifully updated home offering comfort, flexibility, and thoughtful upgrades throughout. This beautiful property backs to woods, providing a peaceful and private setting to enjoy year-round. Inside, fresh new paint throughout, new carpet upstairs, and new vinyl plank flooring in the basement give the home a clean, move-in-ready feel. The main level features generous living spaces, including a large office with glass French doors, perfect for working from home, studying, or creating a quiet flex space. The living room is warm and inviting with a new propane fireplace, accented by a striking floor-to-ceiling brick backdrop and mantle. The gourmet kitchen offers stainless steel appliances, abundant cabinet space, and a large pantry, making it ideal for everyday cooking and entertaining. Upstairs, you’ll find comfortable bedrooms and refreshed finishes, while the lower level adds incredible versatility. The basement includes another potential bedroom, a full kitchen, a full bath, and a stackable washer and dryer that convey, making it an excellent option for an in-law suite, guest space, or potential income-producing area. There is also plenty of storage throughout the home, giving you room for everything. Outdoor living is a major highlight, with a maintenance-free deck featuring storage underneath, plus a professionally installed paver patio with firepit—perfect for relaxing evenings or entertaining guests while enjoying the wooded backdrop. The driveway provides extra parking alongside the garage, adding everyday convenience. Additional valuable features include a newer roof, dual-zone HVAC with units replaced in 2010 and 2021, an emergency backup generator, and a fully paid-for solar system with warranty, offering peace of mind and energy efficiency. This home combines space, updates, privacy, flexibility, and long-term value in a desirable Leonardtown location.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,014
Status:
Active
MLS#:
MDSM2031122
Type:
Single Family-Detached
Subdivision:
Breton Bay Landing
Lot size:
0.42 Acres
Year built:
1990
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

BRAND NEW ROOF! Built as a model for the neighborhood, this 3-bedroom, 2-bath Rambler will have you checking off your search boxes! Located on a quiet-cul-de-sac street in desirable Breton Bay, this lovely home includes more than 3,000 sq ft of living space and plenty of storage, too. Attractive landscaping greets you on your way to the welcoming front porch. A custom-glass front door leads into a spacious foyer, and main floor that features solid Oak hardwood flooring. New windows flood the the roomy formal living room with natural light, and the space centers on the warm hearth & wood-burning fireplace. Serve guests in the formal dining room, or head to the open kitchen/family room for more informal gatherings. Soft-close-Oak cabinets and drawers, Granite counters, wine rack, pull-out shelves, an island w/ breakfast bar, and NEW refrigerator make this kitchen any cook's delight! When the temp is right, head out the back door and enjoy meals on the screened porch. The flat yard backs up to trees, and is perfect for fun & games with plenty of room to play! Let Fido play, too, as the property is surrounded by an invisible fence. Three spacious bedrooms on the main floor make one-level living easy. The Primary suite includes double walk-in closets, and an updated bath with warm Cork flooring, soaking tub and tiled shower. An updated hall bath w/ tiled tub & shower, and convenient laundry/mud room complete the main floor. Head down to the lower level, and envision how you will use the large rec room! Natural light from two large windows shines on a space that can fit game tables, big screen TVS w/ seating, fitness equipment, or all three! An additional bonus room makes for a quiet retreat, a great home office, or gamer/media room. Unfinished space allows for all your storage needs. A 2-car garage keeps the cars clean, and a backyard shed helps keep it tidy. There are generator & RV hookups, and for added peace-of-mind, the HVAC system & water heater are 5-years young! The Breton Bay community features a waterfront park with beach, fishing/crabbing dock, picnic areas and playground. A public 18-hole golf course w/clubhouse offers memberships that include tennis and pool. Great amenities, Leonardtown schools, near shopping, restaurants, and main commuter routes... this home is one that you will not want to miss. Request a showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,554
Status:
Active
MLS#:
MDSM2031006
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

***AVAILABLE NOW*** RECIEVE $12,500 in CLOSING HELP! (with use of Builder's Preferred Lender & Title) Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, brushed nickel fixtures, a center island (photos shown are representative), large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard—perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,507
Status:
Active
MLS#:
MDSM2030988
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.58 Acres
Year built:
1974
Courtesy: KW Metro Center 703-535-3610
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ADDITIONAL INFORMATION

Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-bedroom, 3-bath split foyer offers space and comfort, and is move-in ready! The main level showcases stunning hardwood floors and a bright, inviting layout perfect for everyday living. The fully finished walk-out lower level features a spacious family room with a cozy fireplace, creating the ideal space for relaxing or entertaining. A large mudroom and laundry area provides excellent functionality and storage. Mudroom has epoxy flooring, laundry sink and oversized washer; washer & dryer are 1 year old. Kitchen & all 3 baths have tiled flooring. Set on a private half-acre lot, the home also offers a rear deck, two-car garage, and generous storage throughout. Leaf Filter brand gutter guards have transferable warranty. Residents enjoy optional membership to the Breton Bay Golf Course, pool, and tennis facilities, along with access to the community beach park and pier—making it easy to embrace the best of Southern Maryland living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,636
Status:
Active
MLS#:
MDSM2030794
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.46 Acres
Year built:
1927
Courtesy: Franzen Realtors, Inc. 301-862-2222
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ADDITIONAL INFORMATION

Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still exhibiting original craftmanship and renovations throughout the years. Livable preserved charm but perfect for an updating to make it your own. Roomy kitchen opens to great room with 9 ft. beamed ceilings, bay window, and a brick fireplace with woodstove all open to expansive sunroom. Master bedroom with large bath with soaking tub, 6’ x 9’ walk in closet and even a bidet. Entrance foyer with laundry area. Second floor 15’ x 7’ loft perfect for extra sleep or rec room. Over 1,600 sq. ft. of finished area plus a newly constructed detached 480 sq. ft. 2 car garage with 2nd level partly finished coach house apartment and 6’ x 10’ covered porch with waterfront views. Apartment is under roof, sided with electrical and plumbing rough-in with over 400 sq. ft. Fully permitted (that’s important). Combined square footage when completed will be over 2,000. Coach House perfect for guests, family, or rental income. Over 100 feet of protected shoreline with 80 ft. pier plus 10’ x 20’ L platform, power boat lift and 1 slip. Nice sized 10 ‘x 21’ deck accessing pier on shoreline. Wooded lot at the end of a dead-end street!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,604
Status:
Active
MLS#:
MDSM2030032
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

***Available Now*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full bath, perfect for a guest suite or home office. Upstairs, enjoy 9’ ceilings, luxury vinyl plank flooring, and an open-concept kitchen featuring 42" upgraded maple cabinets, upgraded granite countertops, a large center island, walk-in pantry, and stainless steel GE appliances. The kitchen flows seamlessly into the dining area and oversized family room, with access to a 14x12 maintenance-free deck overlooking your private, fenced-in backyard. The upper level boasts a spacious owner’s suite with tray ceiling, walk-in closet, and a luxurious ensuite bath with dual vanities and QBHI’s signature deluxe tiled shower. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the top floor. Additional features include: Oversized 1-car garage and 2-car wide driveway, finished and painted garage with drywall, smart home technology with IQ Pro command center, Skybell camera doorbell, and smart thermostat Low-maintenance exterior with stone-to-grade front (per elevation), sodded yard, vinyl fencing, and landscaping package. Community amenities include sidewalks, recreation center, pool, playground, pickleball, and tennis courts, all in the heart of charming Leonardtown. Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,122
Status:
Active
MLS#:
MDSM2030588
Type:
Single Family-Detached
Subdivision:
Schumacher Subd.
Lot size:
11.08 Acres
Year built:
2011
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

MULTIPLE OFFERS RECEIVED! ALL OFFER DUE BY MONDAY MAY 4th at NOON Welcome Home to Your Private Rural Retreat. Nestled on 11 serene, private acres and just steps from St. Mary's River State Park, this stunning 5-bedroom, 2.5-bath Cape Cod offers the perfect blend of country living and modern convenience, all within 15 minutes of Patuxent River Naval Air Station and the charming wharf and dining of Leonardtown. A long gravel driveway with freshly installed bluestone chip leads you to a welcoming front porch. The main floor features an owner's suite with a brand new en-suite bath, two additional bedrooms sharing an updated full bath, a fantastic kitchen with ample storage, and an open family room with a pellet stove. Also on the main level are a dedicated office, a large mudroom/laundry room, and a half bath just off the attached 2-car garage. Upstairs above the garage, two massive additional bedrooms offer incredible flexibility, complete with their own dedicated HVAC system, ideal for guests, teens, or a private home office suite. All HVAC units throughout the home are newer, offering year-round comfort and peace of mind. Step outside to your screened-in back porch and unwind in the hot tub as you take in the tranquil surroundings. When you're ready for more adventure, miles of trails for hiking, fishing, boating, and even hunting are practically at your doorstep. Car enthusiasts and hobbyists will love the detached 2-car garage, currently set up as the ultimate man cave complete with a theater area and gaming space, easily convertible to a workshop. Bonus storage can be found in the attic above the detached garage. The property also features a barn with potential for horse stalls, making it a dream for equestrian enthusiasts or hobby farmers. Whether you're seeking peaceful acreage, outdoor adventure, or a home that truly has it all, this one checks every box. For qualified VA buyers, this home has an assumable VA loan at 2.25%, a rare opportunity in today's market that could mean significant savings on your monthly payment. Don't miss your chance to make it yours.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,624
Status:
Active
MLS#:
MDSM2030516
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.75 Acres
Year built:
2002
Courtesy: Home Towne Real Estate 410-286-9632
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ADDITIONAL INFORMATION

"NO HOA" This charming home offers 1,624 sq. ft. of living space, sits on a generous 3/4-acre lot, and features a new concrete stamped patio perfect for outdoor entertaining.. A true highlight of this property is the presence of Two Primary Suites Primary Suite 1, is an extremely large suite (24' x 19'—including the walk-in closet and attached bath) and features wood laminate floors, crown molding, and a ceiling fan. Attached bath boasts a linen closet, a shower/tub combo, and a nice vanity. Primary Suite 2, offers an attached bath with a tub/shower combo, a ceiling fan, and wood laminate floors. The other two bedrooms are bright and comfortable, featuring ceiling fans and wood laminate floors. The updated hall/guest full bathroom includes a beautiful vanity with ample storage space. The exterior of the property is built for entertainment and practical storage: Large Backyard: Workshop Space: A 12' x 16' metal roof shed is equipped with electric, providing a perfect spot for hobbies or extra storage. Ample Parking: An extended paved driveway ensures plenty of room for guests or multiple vehicles.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,300
Status:
Active
MLS#:
MDSM2030772
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.24 Acres
Year built:
2008
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are greeted by mature landscaping, a large concrete driveway and a sidewalk that takes you to the front porch. Upon entry you are greeted by a nicely sized 2-story foyer. To the right of the center hall, a living room with a formal dining room situated just in behind it. The kitchen, breakfast area, and large family room encompass the entire back portion of the main floor making this the perfect home for entertaining. A nicely finished hall bath and a large mudroom/laundry room complete the main floor. Upstairs, a very large primary suite is home to a huge walk-in closet and an en-suite bath. The bath has dual vanities, a separate water closet, a soaking tub, and a good sized stand up shower. The bathroom once had a water leak at the tub, which has since been mitigated, however was never built back. The bath will require new flooring and a little bit of tile work around the tub. 3 more large bedrooms and a hall bathroom with a double-sink vanity complete the upstairs. The lower level is in good shape with newer vinyl plank flooring, a small wet bar, a recently updated full bath, and a large 5th bedroom. The rec area is also large with two separate areas which creates the ability to have multiple functions. The back yard is large, flat, and it backs to trees allowing for some built-in privacy. Just down the street are all of the community amenities including a village green w/ a gazebo, a large playground, pickleball court, basketball court, and a community center w/ a large community pool! A little paint, some flooring and a few tasteful updates would bring this home back to life! Take advantage now so that you can enjoy all that Leonard's Grant has to offer! Set up a showing ASAP before this one is GONE!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,034
Status:
Active
MLS#:
MDSM2030524
Type:
Single Family-Detached
Subdivision:
Academy Hills
Lot size:
0.2 Acres
Year built:
2004
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Sellers have outgrown this great Leonardtown location without the hustle and bustle of being in down town. Also offered at less than typical Leonardtown homes where the median sold price is $547,500. This 3 bedroom home has been upgraded with new deck/screened porch in 2023, upstairs vinyl flooring, kitchen quartz and new appliances in 2025 & backsplash & new roof. Be in and settled in this one before the next school year. American Home Shield Home Warranty offered too, to make your purchase a sound decision. Come check this one out.

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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

    $537,500
    12.7%
    change since last quarter
  • # Active listings

    51
    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