Leonardtown MD Real Estate

Leonardtown is quaint Maryland community with a vibrant history. Located about 20 mins apart, the homes for sale Leonardtown is located on beautiful, rural lots and in welcoming suburban neighborhoods. Local vineyards and farms are scattered across the rolling landscape and there are many hiking/walking trails and parks, perfect for those who enjoy an active lifestyle.

Maryland Homes For Sale

Search homes for sale in Mechanicsville and Leonardtown area.  Contact us if you have questions or would like to schedule a showing. You might also be interested in St. Mary's County Real Estate.

40425 Breton View Drive Leonardtown MD 20650
For Rent

MLS Number MDSM2010742

  • Rental
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,288
  • Subdivision Breton Bay Pud

Nice end unit in Breton Bay with tranquil water views! Breton Bay golf course is close by as well. This end unit has Two Primary sized bedrooms with cathedral ceilings with new carpet and private ensuite bathrooms. There is exceptional amounts of closet and storage space in the unit. Large open living room and dining areas with a wood burning fireplace and a deck to enjoy the view. Large kitchen with island has eat in area as well. Lower Level is fully finished and has a large recreation room area and another full bathroom for convenience. Outside the lower level recreation room is nice size patio for sitting and enjoying the view. Entry to the 1 car garage is on this level as well.

Listed by Mary Healey of Wilkinson PM INC

$
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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41420 Silver Charm Court Leonardtown MD 20650
For Rent

MLS Number MDSM2010746

  • Rental
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,565
  • Subdivision Leonards Grant

****Short Term Rental Only**** Available until June 2023. Beautiful Belmont Model in the Leonard's Grant Community. Situated on a quiet cul-de-sac street with woods behind. This home offers hardwood floors throughout main level and grand staircase. The Gourmet Kitchen boasts Gas cooktop, Double Wall Ovens, 42" maple cabinetry, Granite Countertops, "Newer" appliances, Center island, large pantry and table space. The Family room features recessed lighting and a gas fireplace with mantel. The formal dining room is off of the kitchen and there is also the formal living room/home office, powder room, and laundry/mud room. Upper level boasts a spacious primary bedroom with two large walk-in closets, luxury primary bath with soaking tub, walk-in shower, and separate vanities. Three very generous sized bedrooms and full bath complete the upper level. The fully finished lower level is complete with extra living space as well as a 5th bedroom and full bath and walks out to backyard. Community amenities include club house, playgrounds, swimming pool, exercise field, side walks, ponds, tennis and basketball courts and green space. Close to Historic Leonardtown Square and the Leonardtown Wharf which offers shops, restaurants, and waterfront park. Walk or bike to the Elementary School and the Library. Great location and close to Pax River Naval Air Station. This home has so much to offer and won't last long!

Listed by Christine T Floyd of EXP Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22676 Chickadee Lane Leonardtown MD 20650
For Rent

MLS Number MDSM2010508

  • Rental
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,000
  • Subdivision Avenmar

INCLUDES UTILITIES, upper 2 levels of home and 1 garage bay. Basement is occupied by owner. No shared space between basement apartment and upper levels. Situated on a large wooded lot, this beautiful brick colonial is located in the neighborhood of Avenmar, near Breton Bay. You'll find upgrades throughout including a gourmet kitchen, butlers pantry and tons of cabinets space, granite counters, upgraded appliances, detailed wood flooring, large well appointed rooms and a fireplace. HOA amenities include dock, boat launch, clubhouse, pool, trails, volleyball and tennis courts, horse boarding (additional cost). Owner(s) request a minimum credit score of 725. Pets allowed are on a case by case basis with additional non-refundable deposit and must be friendly with other pets and invisible fence trained/trainable.

Listed by Susan Sokoloff of Leonard Realty,Inc.

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$
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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41608 Briarwood Circle Leonardtown MD 20650

MLS Number MDSM2010712

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,376
  • Acreage 0.05

Immediate Delivery Home with a $25,000 Incentive! Can be used towards closing, rate buy down, or options! Purchase with $0 out of pocket!! Why would you buy a re-sale home and have to worry about repairs/maintenance when you could own a brand new home for the same price! This 3 bedroom 3.5 bathroom townhome feels like a single family with almost 2400 finished sqft. Notable features include granite countertops, 9' ceilings, open floorplan, tile shower/tub surround in the primary bedroom, a large walk in closet in the primary bedroom, LVP flooring & more! All of the rooms are spacious! The 2-car garage is oversized! The private driveway fits 4 cars! Clark's Rest offers the largest townhomes with the most parking and open space! All units back to trees and common area! Neighborhood includes a village green, clubhouse/pool & a playground! Live the Leonardtown Lifestyle and use the Trolly to head into town and enjoy all of the shopping/dining/entertainment! This sizeable home partnered with all that the neighborhood and surrounding area has to offer is definitely worth a look! 5 additional units to choose from!

Listed by Mark A Frisco Jr. of CENTURY 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41435 Osborne Lane Leonardtown MD 20650

Leonardtown, MD41435 Osborne Lane

Price$645,000

Est. Mortgage: $/month

MLS Number MDSM2010698

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,145
  • Acreage 0.18

This beautiful 2018 Lexington model has a 2 car rear load garage with a 12' extension, and was built to impress. You cannot help but notice the beautiful lawn when you drive up. The grass is lush and the home shows pride of ownership. Lovely hardwood flooring throughout the entire main level, with the exception of vinyl flooring in the half bath. The great room is huge and provides the coziness and warmth of a gas fireplace. The expansive kitchen with upgraded cabinetry will not disappoint. Graphite appliances, granite counters, gas cooktop, a beautiful deep farm sink and a huge island make this lovely kitchen a chef's delight. Enjoy the benefit of the separate coffee bar and very large pantry just around the corner. The guest suite with private bath on the main level offer the perfect spot for your in-law suite or private study. The upstairs is home to four bedrooms and a hall full bath with two sinks. The primary bedroom has its own sitting area. The primary bath is large with a rounded wall of glass at the shower. Two sinks and a large walk in closet are the finishing touches on this great space. No need to lug laundry up and down the steps, as the oversize laundry room is on the bedroom level, and includes a laundry sink. All bedrooms are prewired for fans and the home has a central vacuum system. There is loads of room in the basement to spread out and enjoy the large family room. The sixth and final bedroom and full bath are located in the basement as well. 9' ceilings on the 1st and 2nd floors with 8' ceilings in the basement. The mechanical room provides additional great overflow storage. The maintenance free deck with vinyl railings is host to the ideal entertainment area. This home's fully fenced backyard adds both privacy and safety for children and pets alike. The stamped concrete patio under the deck is yet another great outside spot to enjoy. To the right of the driveway you will find the storage shed wired with electric. Know the home has also had a generator switch installed and is prewired for a hot-tub, should you choose. There is simply not much these owners have left undone. Why wait for new construction when this lovely home can be yours before the new year is rung in! Community center with pool, playgrounds and basketball hoops make this an ideal family destination! Come give us a look!

Listed by Robin Poe Errington of CENTURY 21 New Millennium

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21715 Pebble Beach Court Leonardtown MD 20650

MLS Number MDSM2010650

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,437
  • Acreage 0.7

Here's a chance to live in popular Breton Bay - across the street from the Breton Bay golf course/country club, just steps away from the community association beach/pier ($75/year) and around the corner from a private marina. Wonderful corner lot with mature weeping willow & crape myrtle trees, seasonal water view of Cherry Cove, and a stately brick front colonial with plenty of room to spread out. The home features 5 bedrooms/5 full baths (5th bedroom on main level optionally used as private library/study), finished walk-out basement, Trex deck off kitchen w/hot tub, wood and new carpet flooring, and spacious main level living space. You'll find the family, living, dining rooms + remodeled eat-in kitchen, 5th bedroom/study, full bath and laundry on main level. Upper level features an enormous primary en Suite bedroom plus 3 additional large bedrooms and 2 full baths. The lower level has large a rec/game room, additional flex room and full bath, and sliders opening to the back yard with shed. HSA Home Warranty. This is a great place to call home!

Listed by Lucy L Barbour of CENTURY 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21126 Arbor Court Leonardtown MD 20650

Leonardtown, MD21126 Arbor Court

Price$395,000

Est. Mortgage: $/month

MLS Number MDSM2010696

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,728
  • Acreage 0.47

Welcome to 21126 Arbor Ct! This home is located in the quiet Wilderness Run subdivision, only a few minutes away from Leonardtown schools, the Square, Wharf, hospital, shopping and dining! Freshly painted and with all new carpet, this property awaits its new owners! On the main level, you will find an office to your right and dining room to the left as you come through the front door. The family room is spacious, with a propane fireplace that can be hooked up just in time for the winter months. With a traditional floorplan, the kitchen is a separate space, with island, breakfast nook and stainless steel appliances. The deck outside is perfect for entertaining, overlooking the large backyard with almost half an acre. As you come up the stairs, you'll see one bedroom on each side and the hallway full bath. Tucked in the back, the master bedroom has a walk-in closet and its own en-suite bathroom with double vanities, soaking tub and separate shower. Come enjoy these beautiful fall days in your new home, outside on your quiet yard. This subdivision also has no HOA! What else could you ask for? Schedule your showing today!

Listed by RE/MAX 100

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41429 Challedon Way Leonardtown MD 20650

Leonardtown, MD41429 Challedon Way

Price$610,000

Est. Mortgage: $/month

MLS Number MDSM2010510

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,660
  • Acreage 0.22

Beautiful new listing in Leonard's Grant! You're not going to want to miss this home with a fabulous layout, on the corner lot! Location is a prime spot! This house has an extremely large, first floor primary bedroom that is located off of the kitchen. The bathroom is equipped with two separate sinks, a garden tub and a large, upgraded shower with glass doors. This gourmet kitchen is one that people dream of…Upgraded stainless steel appliances, including a Bosch dishwasher! Take your food to eat at the bar, the patio, right off the kitchen or the dining room! Dining room is spacious with gorgeous pillars. The main floor also boasts a study surrounded by two sets of double French doors, head out of the study and you'll see the powder room and the first floor laundry. The second floor of this home has another living area and three bedrooms. In between two of the bedrooms, you will see the buddy bathroom. The basement of this home is absolutely enormous and has unlimited potential! It is currently unfinished, but has a rough in for a bathroom. This can easily be finished with a bedroom, bathroom, hang out area and still has room for an unfinished storage area!

Listed by Heather Leigh Foster of RE/MAX One

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41810 Eastwick Lane Leonardtown MD 20650
For Rent

MLS Number MDSM2010614

  • Rental
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,134
  • Subdivision Foxwell Condominiums

Welcome to Foxwell Condominiums in Leonardtown. Location, Location, Location!!! These condos are just a short walk to everything in the Leonardtown Square....Restaurants, Coffee shops, shopping, waterfront Wharf and Leonardtown life. The unit consists of 2 bedrooms and 2 full baths. Both bedrooms have walk in closets with built-ins. The kitchen boasts granite counter tops with center island and pendant lights, table space, pantry, and Stainless Steel appliances to include dishwasher, refrigerator, microwave, and disposal. Off the kitchen is the separate laundry room with washer and dryer included. Open floorplan with spacious family room and a walk-out to ground level rear covered porch with private views. Did we mention LOCATION? Patuxent Naval air station, local beaches, parks, waterways, and museums are all just a short drive away. Looking for a minimum of a one year lease and must have a credit score of 700 or higher to apply. Pets accepted case by case and weight restrictions apply. EASY LIVING... HOA covers all maintenance with trash removal and snow removal included.

Listed by Wayne Floyd and Christine T Floyd of EXP Realty,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22475 Armstrong Drive Leonardtown MD 20650
Pending

MLS Number MDSM2010636

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,890
  • Acreage 0.64

Custom CHARM! This 1740 Sqft ALL BRICK 4 Bedroom 2 Bathroom Rambler w/ a 2 Car Attached Garage & a Partially Finished Basement is FULL of CHARM & Character! From the Street, the FLAT 2/3 of an Acre Corner Lot is the first thing you notice! The large, paved driveway leads you to sidewalks that flank the driveway and lead you to either the front or rear entrances. Around front a unique patio area is surrounded by a decorative brick barrier which also encloses a small courtyard/garden area. Just inside you enter into the warm & inviting great room which has vaulted ceilings, custom built-ins, a brick fireplace, crown molding, & gorgeous pine flooring. To the right is the bright and airy kitchen/breakfast area. The breakfast area has ample table space & a large double window overlooking the back yard. The kitchen has custom white/glass cabinetry, butcher block countertops, gourmet stainless steel appliances, & recessed lighting. Located just off the great room is a screened porch that leads to two separate patio areas & the fenced in back yard. To the left of the family room is the main floor hallway leading to the hall bathroom, a primary bedroom w/ a full bathroom, & 3 additional bedrooms. The primary bedroom is large enough to fit a king bed. The large primary bathroom is equipped with a ceramic tile floor & shower as well as a custom vanity & mirror. A walk-in closet with custom built-ins completes the primary suite. The basement begins with a large, finished laundry room and that spills into an L-shaped unfinished area perfect for storage. Outside the back yard is truly one of a kind w/ plenty of fenced in area for your pets, a built-in chicken coop, & a shed that triples as a greenhouse, potting, and/or storage shed! This home is a must see!

Listed by Mark A Frisco Jr. of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41614 Briarwood Circle Leonardtown MD 20650

MLS Number MDSM2010628

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,849
  • Acreage 0.11

RARE End unit! This house is loaded with options!!! Theater room and finished bedroom in the basement. Immediate Delivery Home with a $25,000 Incentive! Can be used towards closing, rate buy down, or options! Purchase with $0 out of pocket!! Why would you buy a re-sale home and have to worry about repairs/maintenance when you could own a brand new home for the same price! This 3 bedroom 3.5 bathroom townhome feels like a single family with almost 2400 finished sqft. Notable features include granite countertops, 9' ceilings, open floorplan, tile shower/tub surround in the primary bedroom, a large walk in closet in the primary bedroom, LVP flooring & more! All of the rooms are spacious! The 2-car garage is oversized! The private driveway fits 4 cars! Clark's Rest offers the largest townhomes with the most parking and open space! All units back to trees and common area! Neighborhood includes a village green, clubhouse/pool & a playground! Live the Leonardtown Lifestyle and use the Trolly to head into town and enjoy all of the shopping/dining/entertainment! This sizeable home partnered with all that the neighborhood and surrounding area has to offer is definitely worth a look! 6 additional units to choose from!

Listed by Christopher A Hill and Mark A Frisco Jr. of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41942 Kentucky Court Leonardtown MD 20650
For Rent

MLS Number MDSM2010630

  • Rental
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,124
  • Subdivision Academy Hills

Also listed for sale and was just reduced to 525,000.00 with MLS # MDSM2009350 Excellent Credit Required Drive up your private driveway to a home with over 4,000 square feet of living space. The eat in kitchen features a very spacious island with lots of storage underneath and plenty of seating. The dining area affords lots of room for even the largest of families. With its open floor plan you will feel relaxed as you move into a family room that allows everyone room to spread out and watch tv while enjoying the beautiful gas fireplace which will knock the chill off even the coolest of nights. As you move upstairs to the second floor you will find four bedrooms and two full baths. The primary bedroom has plenty of room for even the largest of bedroom suites. The primary bath has dual head shower, beautiful drop in tub, and separate water closest. Here you will also find a Walk in closet the size of another room which also offers an upstairs laundry without sacrificing closet space. This home boasts two covered and fully screened in deck/patio areas, with stairs leading down from above or access below through the French doors on the lower level you will find a five person hot tub to soak the long day away even during the middle of a cold and snowy night. Moving down to the lower level you will find a wet bar, full bath, home theatre/living area, gym and possible 5th bedroom. You will also find two additional unfinished rooms providing plenty of storage. Oversized two car garage fully insulated with an abundance of attic storage space with an easy to use pull down step system. This home is located right off of Route 5 with easy and walkable access to downtown Leonardtown and itâs dining and entertainment establishments, parks, wharf and more. A short commute to NAS PAX RIVER and Solomons Island. Convenient to D.C., Baltimore and Annapolis.

Listed by Terri Lynn Hamrick of O Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23086 Town Run Drive Leonardtown MD 20650

Leonardtown, MD23086 Town Run Drive

Price$641,171

Est. Mortgage: $/month

Pending

MLS Number MDSM2010540

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Acreage 0.21

Under Contract-To Be Built: Quality Built Homes, Inc, The Fairfax Fairfax A1 Model, , 16x12 Built-in porch, Additional windows through out, coffered ceiling, hardwood stairs, first floor in-law suite; full bath & walk-in closet, Upstairs 4 bedrooms, primary bedroom includes angle trayceling, sitting room, two walk-in closets, and large 7x4.5 tiled shower with two shower heads, recessed lights, seat, ledge & shelf. Huge laundry room. Hall bath has double vanities and tub/shower combo with rec'd light & addt'l window. Lower Level Finished Basement with LL Bedroom and large bathroom. ***Meadows at Town Run is in the Town of Leonardtown, Special Tax Rate***

Listed by Laura Bernth of RE/MAX One

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27983 Point Lookout Road Leonardtown MD 20650

MLS Number MDSM2010518

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 944
  • Acreage 0.64

Sale of an older home in fair condition, perfect for an FHA k loan. Home needs a major rehabilitation. Located in the Business District of Loveville, with Farmer's Markets and Agricultural/Commercial uses nearby. This property is zoned VMX and has tremendous upside potential. No Warranties are either expressed or implied, this is an "AS IS" sale. Recent perc was approved. THERE IS NO WELL OR SEPTIC ON THE PROPERTY, BOTH NEED TO BE INSTALLED. Buyer to pay all closing costs and transfer taxes.

Listed by Gordon Stellway of O Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27983 Point Lookout Road Leonardtown MD 20650

MLS Number MDSM2010516

  • Commercial
  • Property SubType Mixed Use
  • Acreage 0.64

This is the sale of an older home that could be remodeled under the FHA program. Located in the VMX Business District of Loveville near Farmer's Markets and Agricultural/Commercial Products Businesses. Tremendous upside potential due to zoning! The land was recently perced and approved. Property is being sold in strict "AS IS" Condition with no Warranties or Disclosures. Buyer to pay all closing costs and transfer taxes. BUYER TO PAY FOR WELL AND SEPTIC SYSTEMS.

Listed by Gordon Stellway of O Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25265 Ledgewood Way Leonardtown MD 20650

Leonardtown, MD25265 Ledgewood Way

Price$774,900

Est. Mortgage: $/month

MLS Number MDSM2010408

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,500
  • Acreage 1.13

A Breton Knolls exclusive offering. Be the first to call this to-be-built custom-crafted home yours! Located in the heart of Leonardtown on oversized lots, this new 24-lot subdivision offers an elegantly crafted home by a well-known local builder. The Jackson floor plan perfectly combines the essence of a Colonial Farmhouse with a modern twist to include over 3,000 sqft of living space spread throughout four bedrooms and three levels - ideal for a busy lifestyle and entertaining. Sunlight, hardwood flooring, and coffered/tray ceilings fill the floor plan with endless options for customization available. Imagine filling your home with savory scents from the bump-out kitchen with cathedral ceilings and finishes of your choosing. The kitchen gives way to the larger-than-life living room with soaring two-story ceilings and a shiplap and stone surround fireplace with a show-stopping Amish mantle - the perfect spot for mementos. The Jackson floor plan also offers a sophisticated main-level primary suite designed to evoke utter tranquility with a walk-in closet and spa-like bathroom. Additional amenities included at the base price include a water table stone front exterior, black windows, black gutters, stone piers grounding the front porch, an 8-ft front door, and much more. The Jackson floor plan in Breton Knolls starts at $774,000, with a list of customizations and add-ons available upon request.

Listed by RE/MAX 100

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23445 Grovewood Court Leonardtown MD 20650
Pending

MLS Number MDSM2010410

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,451
  • Acreage 0.05

One of ONLY 7 Remaining New Construction Townhomes in Sought After Clark's Rest! Immediate Delivery Home with a $25,000 Incentive! Can be used towards closing, rate buy down, or options! Purchase with $0 out of pocket!! Why would you buy a re-sale home and have to worry about repairs/maintenance when you could own a brand new home for the same price! This 3 bedroom 3.5 bathroom townhome feels like a single family with almost 2400 finished sqft. Notable features include granite countertops, 9' ceilings, open floorplan, tile shower/tub surround in the primary bedroom, a large walk in closet in the primary bedroom, LVP flooring & more! All of the rooms are spacious! The 2-car garage is oversized! The private driveway fits 4 cars! Clark's Rest offers the largest townhomes with the most parking and open space! Neighborhood includes a village green, clubhouse/pool & a playground! Live the Leonardtown Lifestyle and use the Trolly to head into town and enjoy all of the shopping/dining/entertainment! This sizeable home partnered with all that the neighborhood and surrounding area has to offer is definitely worth a look! 6 additional units to choose from! Come and check them out at one of the open houses this weekend Saturday and Sunday from 11-2! Prices of other Units Range from $399,900 - $456,900 (End Unit)!

Listed by Mark A Frisco Jr. of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41895 Tomey Court Leonardtown MD 20650

Leonardtown, MD41895 Tomey Court

Price$489,000

Est. Mortgage: $/month

Pending

MLS Number MDSM2010246

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,192
  • Acreage 0.21

Location, Location, Location....this house has it all! Great home centrally located in town limits of Leonardtown. Home has been well maintained and looking for new owners. Open floor plan on main level with spacious eat in kitchen which flows into the family room. Gas fireplace in family room for upcoming chilly nights. Large kitchen island with bar stool seating, granite counters, tile backsplash, stainless appliances, ample cabinetry storage and kitchen table space. Separate formal dining room, laundry room and powder room also on this level. Upper level has four bedrooms and two full baths. Very spacious primary bedroom with tray ceiling and two walk in closets. Primary en-suite bath has been recently renovated and includes soaking tub, walk in shower and dual vanities. Still need extra space? The lower level walk-out basement offers a finished rec room, full bath and large storage room. Inviting all composite deck for outdoor entertaining overlooks your fully fenced in rear yard. Conveniently located to restaurants, shopping, schools and walking distance to historic downtown Leonardtown. Call today for appointment.

Listed by Cynthia J Ballard of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22695 Washington Street Leonardtown MD 20650
For Rent

MLS Number MDSM2010166

  • Rental
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 11,686
  • Subdivision None Available

Small one bedroom one bath apartment in downtown Leonardtown. Great opportunity to be in the town with many restaurants and attractions within walking distance. Dumpster onsite for trash included in rent fee as well is water and sewer. Excellent credit required. No smoking. No Pets. Online application.

Listed by RE/MAX 100

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41596 Briarwood Circle Leonardtown MD 20650

MLS Number MDSM2010332

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,379
  • Acreage 0.05

Immediate Delivery Home with a $25,000 Incentive! Can be used towards closing, rate buy down, or options! Why would you buy a re-sale home and have to worry about repairs/maintenance when you could own a brand new home for the same price! This 3 bedroom 3.5 bathroom townhome feels like a single family with almost 2400 finished sqft. Notable features include granite countertops, 9ft ceilings, open floorplan, tile shower/tub surround in the primary bedroom, a large walk in closet in the primary bedroom, LVP flooring & more! All of the rooms are spacious! The 2-car garage is oversized! The private driveway fits 4 cars! Clark's Rest offers the largest townhomes with the most parking and open space! All units back to trees and common area! Neighborhood includes a village green, clubhouse/pool, & a playground! Live the Leonardtown Lifestyle and use the Trolly to head into town and enjoy all of the shopping/dining/entertainment! This size-able home partnered with all that the neighborhood and surrounding area has to offer is definitely worth a look! 6 additional units to choose from! Come and check them out at one of the open houses this weekend Saturday and Sunday from 11-2!

Listed by Christopher A Hill and Mark A Frisco Jr. of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25484 Point Lookout Road Leonardtown MD 20650

MLS Number MDSM2010318

  • Commercial
  • Property SubType Office
  • Acreage 0.04

1938 square feet of built-out space in Leonardtown. 1st and 2nd floor. Two conference rooms and 4 offices. The tenant pays CAM charges, water, sewer, trash and electricity.

Listed by Anne Cullins Davis of CENTURY 21 Commercial New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41471 Challedon Way Leonardtown MD 20650

Leonardtown, MD41471 Challedon Way

Price$635,000

Est. Mortgage: $/month

Pending

MLS Number MDSM2010288

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,552
  • Acreage 0.22

Welcome Home! Custom Built Clarke Model situated on a spacious corner lot in desirable Leonard's Grant. This home boasts 5 Bedrooms and 5 Full Bathrooms. All upper level Bedrooms feature their own private en-suite baths. The Primary en-suite includes 2 separate walk-in closets and a Luxury Bath with 2 separate vanities, a grand walk-in tile shower and a separate soaking tub. The laundry room is conveniently located on this upper level. The main level features wood laminate floors and it's own guest bedroom and full bath, along with a dedicated home office which could also be used as a 6th bedroom. The family room features a raised hearth marble surround gas fireplace with mantel, recessed lighting, and open concept into the expansive Kitchen for great entertaining! Granite countertops, 42 inch maple cabinetry, center island with gas cooktop, built-in pantries, recessed lighting, and soft close cabinets in the kitchen. Wrap around front porch with swing, rear stamped concrete patio for outdoor gatherings, and a fully fenced backyard. The lower level is complete with a Family/Rec Room, an additional Bonus Room currently used as a home gym, a separate living area featuring it's own family room, a 5th bedroom with walk-in closet, and full bath. Cute shed to match house and a full lawn irrigation system. 2-car Garage with New Smart Q with Cameras, and openers. This home is part of the Village Series Homes which includes full front and side lawn/garden maintenance through the HOA. Community offers sidewalks, clubhouse, pool, playgrounds, sports courts, greens, athletic field, and community events. Located in the heart of Leonardtown close to restaurants, shops, winery, and waterfront wharf. Walk or bike to Duke Elementary School and to the Leonardtown Library! A most convenient community!

Listed by Wayne Floyd and Christine T Floyd of EXP Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41080 Paw Paw Hollow Lane Leonardtown MD 20650
Pending

MLS Number MDSM2010280

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,156
  • Acreage 3.81

Beautifully maintained contemporary home on a beautiful wooded private lot just under 4 acres!!!! Upper level has 2 bedrooms & 2 baths. Kitchen has granite counters, hardwood floors & stainless appliances along with a brick woodburning fireplace for those winter mornings. Lower level has 3rd bedroom & bathroom. Family room with second woodburning fireplace for the winter evenings!!! HVAC was replaced in 2019, roof is less than 10 years old. Unfinished lower level is a great storage area or shop. No HOA. Can join Breton Bay Community Civic association and use pier, beach & picnic pavillion.

Listed by Carolyn A Kalmus-Choporis and Cynthia M Crispell of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41554 Briarwood Circle Leonardtown MD 20650
Pending

MLS Number MDSM2010256

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,379
  • Acreage 0.05

Immediate Delivery Home with a $25,000 Incentive! Can be used towards closing, rate buy down, or options! Purchase with $0 out of pocket!! Why would you buy a re-sale home and have to worry about repairs/maintenance when you could own a brand new home for the same price! This 3 bedroom 3.5 bathroom townhome feels like a single family with almost 2400 finished sqft. Notable features include granite countertops, 9' ceilings, open floorplan, tile shower/tub surround in the primary bedroom, a large walk in closet in the primary bedroom, LVP flooring & more! All of the rooms are spacious! The 2-car garage is oversized! The private driveway fits 4 cars! Clark's Rest offers the largest townhomes with the most parking and open space! All units back to trees and common area! Neighborhood includes a village green, clubhouse/pool & a playground! Live the Leonardtown Lifestyle and use the Trolly to head into town and enjoy all of the shopping/dining/entertainment! This sizeable home partnered with all that the neighborhood and surrounding area has to offer is definitely worth a look! 6 additional units to choose from!

Listed by Mark A Frisco Jr. and Christopher A Hill of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21820 Hazeltine Court Leonardtown MD 20650
Active With Contract

MLS Number MDSM2010270

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,358
  • Acreage 0.36

Elegance and charm in Breton Bay Landing! This cul-de-sac rambler offers one-level living at its finest. Gorgeous hardwoods throughout main level. 3,300+ sq ft of finished space includes three main floor bedrooms w/ primary en-suite, three full baths and a multi-room lower level. Designer gourmet kitchen with custom cabinetry, granite counters and large accent island w/breakfast bar. Spacious eating and sitting area w/ window bump out. French doors lead out to the inviting screened porch. Living room with cozy propane fireplace, lots of natural light and surround sound system. The formal dining room also makes a great home office or music room. Downstairs, rack 'em up in the huge game room with pool table that conveys. Fitness room, office/study, playroom or teen hangout, the two lower-level bonus rooms fulfill any needs for extra space. Full bath w/shower and lots of unfinished storage, too. Enjoy the park-like setting out back on the brick patio, digging in the raised garden or taking in the beauty of the landscaped yard with underground sprinkler and invisible fence. Convenient mudroom, 2-car garage and 50-year roof installed in 2017. Golf course community convenient to shopping, PAX and Rt 5. Leonardtown schools. Waterfront community park just minutes away. Don't miss this your opportunity, request a showing today! Sellers are looking for timing flexibility and desire a rent-back until after the Holidays.

Listed by Andrew Shemeta and Susan B Stachelczyk of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Copyright 2022 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. 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 RE/MAX Realty Group/100 participates, and is provided by BRIGHT through a licensing agreement. 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.Data last updated December 7, 2022. 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.