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.

40095 Greentree Leonardtown MD 20650

Leonardtown, MD40095 Greentree

Price$950,000

Est. Mortgage: $/month

Coming Soon

MLS Number MDSM2020340

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,416
  • Acreage 6.7

Why wait for new construction? This like-new modern farmhouse is move-in ready and loaded with upgrades! Built by the highly requested Medneck Construction, this sale includes two lots totaling nearly 7 acres, offering ample space and privacy just outside downtown Leonardtown. With over 4,000 finished square feet of living space, a fabulous layout, and incredible potential in the huge unfinished walk-out basement, ready to be transformed into a private apartment, home theater, or gaming area-this home has it ALL! Perfectly situated on a cul-de-sac, this home has amazing curb appeal! Don't worry about keeping your lawn looking fresh and green during the hot summer months; a lawn irrigation system is included! Step inside to a bright, airy, and perfect floor plan! Beaming with natural. light, you can relax in a cozy family room with a stone gas fireplace and a stunning coffered ceiling, offering breathtaking views of the expansive front yard and fenced private backyard. The modern gourmet kitchen sets the stage for culinary creations, featuring gas cooking, double wall ovens, custom cabinetry, and a huge walk-in pantry! Working from home or studying is a breeze in the private main floor office! The main-floor owner's suite features a en suite bath, a massive walk-in closet, its own private laundry room, and private access to the back porch! Bring your furry friends and all the backpacks, because this home features a massive mudroom with custom cabinetry, a doggie shower, a built-in kennel, and a laundry hookup! Upstairs, you'll find three additional bedrooms, two of which share a Jack-and-Jill bath, while the third has its own bathroom. A loft area provides the perfect space for a playroom, teen hangout, or additional home office, while the FROG room (family room over the garage) offers endless possibilities as a second primary suite, game room, or massive home office. A huge 3-car attached garage provides ample space for all your toys, storage, and parking needs. This home also features a total of 3 laundry hookups, ensuring convenience on every level! The outdoor space is equally impressive, with an expansive front porch, a huge screened-in rear porch, a custom brick patio with a fire pit, accented with landscape lighting, and a fenced rear yard! Don't miss out-this home is filled with so much natural light, you'll be happy every day you spend here! You can't build this home for this price today-this is an incredible opportunity! The assumable VA loan at 5% and the numerous beautiful upgrades added by the current owners make this property truly exceptional. Schedule your private tour today!

Listed by Sarah M. Mulford-Martin of EXP Realty,LLC

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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21790 Cove Lane Leonardtown MD 20650

Leonardtown, MD21790 Cove Lane

Price$874,900

Est. Mortgage: $/month

Open House

MLS Number MDSM2022356

  • Single Family
  • Next Open House: Wed 01/22 4:00 pm. to 6:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,150

Welcome to your dream waterfront retreat on Cherry Cove Creek! This stunning 3-bedroom, 3-bathroom rambler sits on 2.79 picturesque acres in Hollywood, offering over 3,150 square feet of thoughtfully designed living space. As the seller is in the process of moving, professional interior photos are on the way, but you don't have to wait to explore the incredible features of this home. The home's centerpiece is the custom kitchen, featuring cherry cabinets, granite countertops, a Sub-Zero refrigerator, Dacor double ovens, a Miele dishwasher, a Thermador induction cooktop, and a Thermador range hood. A spacious pantry room connects to the laundry/utility area, making it as functional as it is stylish. The large family room on the left wing of the house provides ample space for relaxation or entertaining, while the formal dining room with a wood-burning fireplace creates the perfect ambiance for hosting dinner parties. The right wing of the home houses three bedrooms including the primary bed/bath and a hall bath, along with a cozy library nook. The expansive primary suite includes a double closet that's twice as deep as standard closets and a primary bath with a separate soaking tub & shower is ready to shine with a touch of personalization. Throughout the home, thoughtful features like storm windows and hot water baseboard heat paired with central air conditioning ensure year-round comfort. Step outside to discover your private outdoor oasis. The property boasts a gunnite pool with an 8-foot diving depth, surrounded by extensive hardscape patio and decking, ideal for summer gatherings. For boating enthusiasts, the 110-foot pier offers water and electric service, a floating dock, a 40x20 slip, and a 50x16 slip, providing sail boat depth water access to Cherry Cove Creek. A spacious shed with attic storage and electric service, along with an oversized 4-car attached garage, ensures all your storage needs are met. The 2.79 Acre lot is waiting for the perfect buyer to manicure it and bring it back to life. It is mostly flat with a previous garden and fruit trees throughout. The home is constructed with durable Hardie board siding, and recent updates include a newer roof and AC system. With a blend of modern amenities and classic charm, this property is perfect for those seeking a waterfront lifestyle with room to customize and make it their own. Schedule a tour today to see the potential of this incredible home!

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

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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40315 Wathen Road Leonardtown MD 20650

Leonardtown, MD40315 Wathen Road

Price$295,000

Est. Mortgage: $/month

Coming Soon

MLS Number MDSM2022328

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,040
  • Acreage 0.65

This recently renovated rambler features three spacious bedrooms and one modern bathroom. Set on a flat half-acre lot, the property offers ample outdoor space for recreation, gardening, or however you see fit. The new septic tank ensures efficient waste management, enhancing the home's overall functionality. With its updated interiors and generous lot size, this residence combines comfort and convenience in a desirable location.

Listed by Brian L Mayer of EXP Realty,LLC

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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41386 Margrove Circle Leonardtown MD 20650
Coming Soon

MLS Number MDSM2022236

  • Rental
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,195
  • Subdivision Clark's Rest

Discover modern living in this 4-bedroom, 3.5-bath end-unit townhome located in the highly desirable Clark's Rest community. This spacious rental boasts an abundance of natural light, an attached garage, and a fully finished basement for all your living and storage needs. The large balcony off the kitchen is perfect for enjoying your morning coffee or entertaining guests. Pet-friendly on a case-by-case basis, this home offers comfort, convenience, and flexibility. Located near local amenities, dining, and entertainment options, this is the ideal place to call home. Schedule your showing today!

Listed by Matthew A Burgan and Kristen Fratz of Infinitas Realty Group

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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42798 Saint Andrews Church Road Leonardtown MD 20650
For Rent

MLS Number MDSM2022262

  • Rental
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 1,846
  • Subdivision None Available

Charming 1-bedroom, 1 bath lower level apartment in a prime location offers the perfect balance of comfort and convenience. Featuring a large den/office space, it's ideal for remote work or as a cozy study area, plus a large eat-in kitchen. The separate living area creates a comfortable space to unwind. Easy tenant access with just a few stairs down to the entrance from parking area. Lots of storage space! A washer and dryer will be included in a separate storage area by 2/1/2025. Approx. 1700sf, internet, electric, water included **Please do not drive up driveway without an appointment**

Listed by RE/MAX Realty Group

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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40751 Merlin Way Leonardtown MD 20650

Leonardtown, MD40751 Merlin Way

Price$618,500

Est. Mortgage: $/month

MLS Number MDSM2022082

  • Single Family
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,251
  • Acreage 3.21

Stunning 5-Bedroom Colonial on Over 3 Acres in Leonardtown, MD Welcome to this beautifully maintained 5-bedroom, 2.5-bathroom brick-front Colonial, nestled on a private, secluded road in Leonardtown, Maryland. Situated on over 3 acres of land, this charming home offers both peace and privacy while being just minutes away from local schools, shopping, and attractions. Route 5 connects you to nearby areas in Maryland, and commuting to DC and Virginia is a breeze. As you approach this inviting home, you'll be greeted by its exceptional curb appeal, with a large front yard and a picturesque brick exterior. Step inside to discover an open and spacious floor plan that blends comfort and functionality. The large master suite features a luxurious jacuzzi tub, a fireplace, and ample space for a relaxing retreat. The upstairs floor also boasts a conveniently located laundry room and three well-sized additional bedrooms ensuring plenty of room for family and guests. The main level offers a versatile bedroom that could easily be transformed into a den or home office, ideal for remote work or quiet study. And an additional fireplace creating a tranquil ambience for the home. The unfinished walk-out basement presents a blank canvas with endless potential for expansion, whether you envision a home theater, gym, or additional living space. Step outside onto the large deck, where you can entertain guests or simply enjoy serene views of your expansive private backyard and acres of lush, natural surroundings. The property is located in a vibrant community with access to incredible amenities, including the Breton Bay, private pier, resident-only pool with lifeguards, swim lessons, canoe storage and use, playgrounds, tennis courts, a clubhouse, and even horse stables. This home has been meticulously maintained by the current owners, and it's ready for you to ring in the new year in a beautiful new space. Don't miss the opportunity to make this stunning property your own-priced perfectly for its location and features!

Listed by Timothy Chris Plummer of Metro City Realty

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22355 White Oak Road Leonardtown MD 20650

Leonardtown, MD22355 White Oak Road

Price$465,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2022028

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,028
  • Acreage 0.5

COMING SOON! What you have been waiting for: A large colonial with a 1st floor bedroom. This house is located in Breton Bay Community which is a sought after neighborhood. Just move in and enjoy your privacy or choose to join into this active golf/waterfront community. Hoa is optional but with certain fees to you have access to the following (clubhouse, neighborhood beach, pool, playground, kayak launch, picnic area, firepit/grill area, golf course, community pool and also Ironwood grill overlooking Breton Bay. More information go to the Breton Bay web site. This beautiful house has 3 large bedrooms on the upstairs floor and the primary has a En suite. There is a 1st floor bedroom with a closet and window that can be used as a in-law, guest room or study. The very large back yard is fully fenced with a private deck as well as a hot tub (included). The roof was replaced 5 years ago and the A/c 4 years ago. If your looking for parking space, there is plenty here as the driveway has been enlarged.

Listed by Donna M Thomas of O'Brien Realty ERA Powered

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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41820 Eastwick Lane Leonardtown MD 20650
For Rent

MLS Number MDSM2022220

  • Rental
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 868
  • Subdivision Foxwell Condominiums

This 1 bedroom, 1 bath condo is just a short walk to downtown Leonardtown. Condo is being rented fully furnished. Kitchen w/granite counters, stainless appliances, washer/dryer, pantry, bar style seating and eating area. Foyer, kitchen, and eating area have beautiful hardwood floors. Large bedroom w/walk in closet and full bathroom in hallway. Living room with sliders that open to the balcony. In just a few minutes you can enjoy local shops, restaurants, and area amenities. Close to schools, hospital and easy drive to PAX Naval Air station. Rent includes water, sewer and trash service. Tenant responsible for electric and cable/internet. Make your appointment today.

Listed by Kelly D Padgett of CENTURY 21 New Millennium

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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41474 Marwood Circle Leonardtown MD 20650

Leonardtown, MD41474 Marwood Circle

Price$430,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2021914

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,522
  • Acreage 0.05

Offer deadline 1/6/2025 at noon. Welcome Home to this beautiful townhome located in Clarks Rest. Unit is less than 3 years young and is in immaculate condition. There is open space out of the front of the home and unit backs to trees in the rear for additional privacy. Open concept main level with all LVP flooring. Upgraded kitchen to include granite countertops and cabinets with soft close drawers and stainless appliances. Off the kitchen is a nice all composite 19.6' X 12' deck overlooking the woods. The primary bedroom is spacious with two closets (one walk-in) and an attached en-suite bath. Bathroom has soaking tub, dual sinks and separate shower with upgraded ceramic tile. Two other generous sized bedrooms, hall bath and laundry room round out the upper level. Lower level is finished with rec room/office/craft room and full finished bath. The 2 car garage is oversized and plenty of extra parking on the driveway. Community amenities include a community center, swimming pool, tennis and basketball courts and tot lot. Short drive to historic downtown Leonardtown where you will find numerous shops and restaurants to explore. There is also a free trolley in the summer and for special downtown events with a trolley stop right in the neighborhood! Nothing to do here but move right on in and unpack!

Listed by Cynthia J Ballard of CENTURY 21 New Millennium

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22680 Washington Street Leonardtown MD 20650
Active With Contract

MLS Number MDSM2022112

  • Rental
  • Bedrooms 2
  • Bathroom 3
  • Subdivision None Available
  • Year Built 2016

Beautiful apartments in beautifully renovated Seymour Building on the square in Leonardtown! 2 bedrooms and 2.5 baths along with all stainless steel appliances. Washer and dryer included. Rent includes water, sewer, trash .. Apartment # 4. No less than a700 credit score. No pets.

Listed by Karen M Alford-Brooks of CENTURY 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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40459 Breton View Drive Leonardtown MD 20650
Active With Contract

MLS Number MDSM2021936

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,286
  • Acreage 0.06

Welcome to this charming 3-level end-unit townhouse in Breton Bay! Step inside to an open floor plan and unwind by the cozy wood-burning fireplace. Enjoy the screened-in porch or host a BBQ on the deck. The home features two primary bedrooms, a dining area, and an island kitchen with a pantry. The lower level, currently used as a recreational room with a closet and full bath, could easily serve as a third bedroom. HVAV updated in 2022 and stove was updated in 2018. Located within walking distance to Breton Bay Golf & Country Club, as well as the community beach and pier. Schedule your showing today!

Listed by David C Norris Jr. of Topside Realty

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22395 Gore Street Leonardtown MD 20650

Leonardtown, MD22395 Gore Street

Price$370,000

Est. Mortgage: $/month

Open House

MLS Number MDSM2022038

  • Single Family
  • Next Open House: Sat 01/25 12:30 pm. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,456

Discover the charm of 22395 Gore St, nestled in the sought-after town of Leonardtown! This delightful home features a sunroom filled with natural light, offering the perfect space to relax or entertain year-round. The well-appointed kitchen boasts abundant storage, ideal for staying organized while inspiring your culinary creativity. Generously sized rooms provide endless flexibility for living, working, or hosting with ease. The flat, expansive yard invites outdoor fun, gardening, or peaceful evenings under the stars. Located just minutes from schools, picturesque parks, and vibrant shopping and dining options, this home delivers the perfect balance of comfort and convenience. Don't miss your chance to make this Leonardtown gem your own-schedule your tour today!

Listed by William Rabbitt of The Southside Group Real Estate

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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42151 Blacksmith Shop Road Leonardtown MD 20650
Active With Contract

MLS Number MDSM2021894

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 798
  • Acreage 0.5

Listed by Ron Lord of Home Towne Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22395 Hood Lane Leonardtown MD 20650

Leonardtown, MD22395 Hood Lane

Price$595,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2021944

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,120
  • Acreage 4.32

Over the creek and through the woods to your new house we go!! Welcome to ultimate privacy yet such an extremely convenient location. You are just minutes from shopping, restaurants, PAX Naval Base and more! Every time you travel back home it will feel like you are headed to a retreat! New full-length rear deck added in 2024- 900 finished square feet. New fencing in rear yard for pet containment. New custom amish built shed. New HVAC system with extra tech, info red bacterial light killer in 2023 to all levels of the house including indoor and outdoor and an aroma clean sent unit added in 2023. New water heater 2022. This custom built home has your primary bedroom on the main level complete with a very large sitting room and large walk in closet. The attached bath with ceramic tile flooring and large soaking tub will take all your stress away! Second bedroom with private full bath on the main as well at the other side of the house! Very thought out floor plan has a large open family room to the open kitchen with an island, large dining area and custom built cabinetry from Cords! Beautiful hardwood flooring in the kitchen, office, dining area, family room, foyers and hallway. The front porch is a dream! Full unfinished walkout basement is plumbed for a full bath. SO MUCH STORAGE!!!

Listed by Jessica D Raley of CENTURY 21 New Millennium

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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40778 S 40 Drive Leonardtown MD 20650

Leonardtown, MD40778 S 40 Drive

Price$414,980

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2021788

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,560
  • Acreage 0.46

Welcome to this beautiful Cape Cod home, offering 4 spacious bedrooms, 2 full baths, and a versatile flex room ideal as a home office or hobby space. Nestled in a sought-after water-access neighborhood, this home is perfect for enjoying both indoor and outdoor living. Inside, you'll find fresh paint, brand-new carpet, and new flooring throughout. The kitchen boasts of new appliances to include the dishwasher & stove, ensuring a move-in-ready experience. The home also features a newer roof and an oversized two-car garage, providing ample storage and convenience. Outside, the level lot is adorned with mature trees, offering shade and tranquility. Just a short stroll away, residents can join the voluntary Civic Association to enjoy the private community beach, pier, a kayak launch, and a picnic area. The community also offers access to a nearby public golf course and pool, adding even more recreational opportunities to this idyllic location. Your new home awaits!

Listed by Tracey L Summers of CENTURY 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22321 Leonard Street Leonardtown MD 20650

Leonardtown, MD22321 Leonard Street

Price$250,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2021896

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 768
  • Acreage 0.08

Charming Cottage in Water-Privileged St. Clements Bay Discover the serenity of life in this bright and airy cottage, nestled in the sought-after St. Clements Bay community. The home features tasteful updates to the kitchen and bath, blending modern convenience with cozy charm. The level lot includes a fully fenced backyard, perfect for relaxing or entertaining, with a handy shed for extra storage. Living here is more than just owning a home-it's embracing a lifestyle. Spend your days exploring the Bay, indulging in water activities, or unwinding at nearby parks and marinas. Whether you're seeking a peaceful retreat or a year-round residence, this gem offers a slice of paradise in Southern Maryland, all within convenient reach of DC, Annapolis, Baltimore, and Dahlgren.

Listed by Lesa K Clark of Redfin Corp

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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41610 Courthouse Drive Leonardtown MD 20650

MLS Number MDSM2021918

  • Commercial
  • Property SubType Office
  • Acreage 0.18

Prime second floor office space available at 41610 Courthouse Drive, ideally situated directly across from the St. Mary's Circuit Courthouse. This corner lot location offers a move-in ready professional office suite featuring five private offices with an existing buildout. The space includes private restrooms and is perfectly positioned in a highly walkable area in the heart of Leonardtown. This prime location is ideal for law firms, professional services, or government contractors, offering outstanding visibility and easy access to courthouse and supporting services. The space is well-appointed with window views and maintains an established professional environment. The central location provides excellent foot traffic and convenience for both clients and employees.

Listed by Nicholas Stellway of O'Brien Realty ERA Powered

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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41041 Knight Road Leonardtown MD 20650

Leonardtown, MD41041 Knight Road

Price$799,900

Est. Mortgage: $/month

Pending

MLS Number MDSM2021808

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 5,716
  • Acreage 2.04

This stunning estate is a true masterpiece, set on multiple acres of lush, meticulously landscaped grounds in one of the most sought-after neighborhoods. Boasting expansive living spaces both inside and out, this home offers unparalleled luxury and privacy. The sprawling property provides a sense of serenity and seclusion, yet remains conveniently close to top-tier schools, local beaches, and fine dining options. The residence itself is a breathtaking showcase of architectural excellence, featuring 6 bedrooms, 5 bathrooms, and an array of spacious living and entertaining areas. From the grand entryway to the soaring ceilings, every inch of this home exudes elegance and sophistication. Custom finishes, designer touches, and state-of-the-art amenities elevate every room, while large windows throughout allow for an abundance of natural light and breathtaking views of the surrounding landscape. Whether you're hosting a grand event or simply enjoying a quiet evening, this home provides the perfect setting for every occasion. The property also offers ample space for outdoor activities including gardening and bird watching. Mature fruit trees, and expensive planting have curated this space to be unlike any other. Two greenhouses will convey with this property. The size of this home is unparalleled to it's competitors. The open concept and the overall quality of construction is something that will leave you saying WOW! There is a FULL partially unfinished (fully framed) basement with a full bathroom, all electric and plumbing has been done to make the remaining pieces of having a finished basement space easy to conquer in the future! The basement also boasts stained concrete flooring throughout that looks very nice! The wood burning stove both on the main level AND in the basement are fully operational and a great secondary heat source.

Listed by Connie Gunn of CENTURY 21 New Millennium

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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23246 Clarks Rest Road Leonardtown MD 20650
Active With Contract

MLS Number MDSM2021836

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,024
  • Acreage 0.16

Welcome to this beautiful home nestled in the highly sought-after Clark Rest Subdivision in Leonardtown, Maryland. This charming neighborhood offers a wealth of amenities, including a pool, playground, basketball court, tennis court, and a community center. Additionally, the Leonardtown Trolley conveniently runs through the neighborhood during the summer and holiday seasons, providing easy access to local attractions and events. This spacious 5-bedroom home boasts over 3,000 square feet of finished living space, offering ample room for all your needs. The main level features gleaming hardwood floors throughout, providing a warm and inviting atmosphere. The fully finished basement offers additional living space, ideal for a home theater, gym, or playroom. The convenience of an upstairs laundry room makes daily tasks a breeze, and the thoughtfully designed layout ensures privacy and comfort for everyone. Don't miss the opportunity to make this wonderful home yours-offering both a prime location and incredible amenities, it truly provides the best of both worlds in Leonardtown.

Listed by Jesieryl U Hartzer of CENTURY 21 New Millennium

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22750 Washington Street Leonardtown MD 20650

MLS Number MDSM2021820

  • Commercial
  • Acreage 0.19

Commercial pad site approved for mixed use. Acceptable uses to include office, retail, restaurant and residential. Located in the heart of leonardtown.

Listed by John M Jordan of CENTURY 21 New Millennium

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22780 Washington Street Leonardtown MD 20650

MLS Number MDSM2021798

  • Commercial
  • Acreage 0.46

Commercial pad site located in historic leonardtown approved for mixed use. Pad site would accommodate 7800 square foot office building or 4500 square foot residential dwelling. Site plan available for review.

Listed by John M Jordan of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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 Chelsey Faye Lane Leonardtown MD 20650

MLS Number MDSM2021276

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,566
  • Acreage 0.58

Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom Creations. This remarkable property is shown with numerous upgrades and showcases exquisite craftsmanship throughout. Offering spacious living areas, this home provides the perfect blend of comfort and luxury. Building a custom home allows you to choose between the standard home on a crawl space or opt for a basement foundation for an additional cost, giving you the opportunity to personalize this beautiful dwelling to your exact needs. If there is some other details you want to add or change you have the ability to do so! Don't miss this opportunity to own a truly unique home that combines style, functionality, and future potential. v. df **Price reflects standard builder features.

Listed by Jessica Lynn Ascenzo of JPAR Real Estate Professionals

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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22380 White Oak Road Leonardtown MD 20650

Leonardtown, MD22380 White Oak Road

Price$455,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2021666

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,680
  • Acreage 0.63

Welcome to your dream home in the highly sought-after Breton Bay community of Leonardtown, Maryland! This property is a true standout, with major repairs and thoughtful upgrades already done to provide ultimate comfort and peace of mind. At the top of the list are a brand-new septic system and a new roof, alongside a host of enhancements including a fenced rear yard, leaf guards, a new roof on the shed, a new pellet stove, and new lower-level carpet. You'll also find updated bathroom elements, an extended parking pad, a new electrical panel with RV 50-amp install, a water filtration system, updated stainless appliances, and an exterior French drain system. Sold as-is. NO HOA - with an optional private beach membership that unlocks access to a playground, pier, sandy beach, kayak launch, picnic area, fire pit/cooking station, and a spacious gazebo for gatherings. Plus, you're just steps away from the public community pool, golf course, and tennis courts, with memberships available for purchase. After your showing, treat yourself to a meal at the Ironwood Grill overlooking the stunning bay views at the top of the golf course-open to the public! Bonus flooring detail: Hardwood floors rest beneath the upper-level carpet, (which has just been deep steam cleaned), waiting to be restored to their full glory if desired. The current carpet upstairs has been left intentionally, allowing a new owner the flexibility to refinish the floors without removing brand-new carpet. Don't miss this rare opportunity to own a beautifully updated home with unmatched amenities in an exceptional location! Fence note & yard note: New septic system was just installed. Septic company wants the soil to settle, and will return to get the yard prepped for new owners. Fence on side will be put back.

Listed by Diana Washabaugh of KW Metro Center

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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41640 Courthouse Drive Leonardtown MD 20650

MLS Number MDSM2021618

  • Commercial
  • Property SubType Office
  • Acreage 0.03

Listed by John M Jordan of CENTURY 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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23245 Jenifer Court Leonardtown MD 20650

Leonardtown, MD23245 Jenifer Court

Price$584,850

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM2021420

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,841
  • Acreage 0.3

Beautiful 4 bedroom home in the convenient and established Single Tree neighborhood feels like your “forever home” the minute you walk in the front door! This house makes a statement with the large 2 story foyer with cathedral window and chandelier. The spacious main floor has it all! A great room featuring gas fireplace is open to the large kitchen with bar seating at island and separate dining area for big gatherings. Formal living room open to formal dining room with bay windows, and convenient half bath. Informal dining area has sliding glass doors to small deck and garden patio and back yard. The tiled sunroom overlooking the back yard is a retreat in and of itself, with windows galore, cathedral ceiling, fan, and french doors. Dedicated large office with antiqued paned door for privacy is an oasis for the work from home professional. **4 bedrooms and 2 full bathrooms on the upper lever. The Master Suite has hardwood floors, and a divided his/hers walk in closet. The Master Bath has a shower, large whirlpool garden tub, double sink, and separate toilet room. Kids' shared bathroom also has double sink. Owners have lovingly taken great pride of ownership of this home, and it shows! **Huge recently finished basement with new carpet is light and airy with oversized rec/family room and half bath. Oversized bonus room with ceiling fan and ample closet space can easily serve guests or be a second office or craft room. A third of the basement is a large unfinished storage area. Beautifully landscaped corner lot with mature trees and shrubs, bulbs, flowers, and lawn. Enjoy the afternoon breeze in hammock, or BBQ on the patio in private back yard. Decorative metal fence protects pets or small children. The backyard faces a wooded common area for privacy and a park like feel. Leased Tesla solar panels lowers electric bill by average of 50%! **Community: Singletree Neighborhood has low annual POA fee of only $175, underground utilities, decorative lamp posts, and community gazebo. Can walk or bike to adjacent neighborhoods without getting on major roads. Hospital and medical/dental offices within walking distance. **Short 1 mile stroll to quaint downtown Leonardtown to enjoy restaurants, bakeries, coffee shops and live music on the square. Or head down to Breton Bay and Leonardtown Wharf to enjoy the park, playground, fishing, free boat dock, ice cream and gorgeous sunsets. St. Mary's county is a haven for boaters and fishermen with water and boat access to Potomac River, Patuxent River and Chesapeake Bay surrounding this unique peninsular county. **Family Pool membership for only $400/year at nearby Breton Bay Country Club. The Library, Elementary School, and Senior Center are all within walking distance. The Shopping Center is just a mile away with all the basics (groceries, pharmacy, gas, banks, etc.) right here in town. Just 12 miles from Solomon's Island for live weekend entertainment, wonderful restaurants, shopping, boat rentals, boardwalk, etc. A Nature lover's dream- local State Parks include Point Lookout, Newtowne Neck, Myrtle Point, and more. ****ENVIRONMENTALLY FRIENDLY! Home comes equipped with a Tesla leased rooftop solar system. Tesla handles 100% of the maintenance at no cost to the home-owner. Transferring the existing lease to the new owner is simple.

Listed by Thomas S Hennerty of NetRealtyNow.com,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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 2025 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 January 21, 2025. 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.