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$695,000
5 Beds 4 Baths
Welcome Home! A covered front entry and separate covered sitting porch create a charming first impression. Step inside to a two-story foyer with hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room is ideal for a home office, library, study, or playroom. The dining room flows through the butler's pantry and adjoining walk-in pantry before opening to the kitchen. A large center island anchors the kitchen, featuring granite countertops, abundant cabinetry, a gas cooktop, and double wall ovens. The kitchen opens to the family room, where a gas fireplace creates a warm and inviting gathering space. Upstairs, the owner's suite features a spacious bedroom, two walk-in closets with custom closet systems, and a private bath with a double vanity, a soaking tub with a tile surround, and a beautifully tiled walk-in shower with dual shower heads. Three additional bedrooms, a full hall bath, and a conveniently located upper-level laundry room complete the upper level. The finished walk-out lower level is designed for entertaining, featuring a spacious recreation room with easy access to the patio and backyard. A fifth bedroom with a walk-in closet, currently outfitted as a fitness room, is complemented by a full bath, offering excellent flexibility for guests, multigenerational living, or a private retreat. An unfinished storage room provides valuable additional storage. As the day winds down, the composite deck offers a peaceful place to relax and enjoy the changing colors of the evening sky. The fully fenced backyard features raised garden beds and generous open space for outdoor enjoyment. Located in the sought-after community of Clark’s Rest, residents enjoy an exceptional lifestyle with amenities that include a pool, clubhouse, playgrounds, tennis courts, sidewalks, jogging trails, and more. Just minutes from downtown Leonardtown, shopping, dining, and the Leonardtown Wharf, this home offers the perfect blend of comfort, convenience, and community. Schedule your private tour today!

23214 Dairy Barn Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$459,900
4 Beds 4 Baths
IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2- Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf, restaurants, boutique shopping, parks, award-winning schools, and an easy commute to NAS Patuxent River, this home combines modern living with an unbeatable location. Featuring three spacious bedrooms, two and a half bathrooms on the upper level, and a versatile lower level currently configured as a fourth bedroom with its own full bathroom, this home offers exceptional flexibility for guests, a home office, fitness room, or additional living space. The open-concept main level is filled with natural light thanks to the desirable end-unit location. The gourmet kitchen showcases quartz countertops, abundant cabinetry, a large center island, gas cooking, and seamless flow into the dining and living areas, making it ideal for both everyday living and entertaining. The upgraded gas fireplace serves as a beautiful focal point, creating a warm and inviting atmosphere. Retreat to the spacious primary suite featuring a tray ceiling, generous walk-in closet, and an ensuite bath complete with dual vanities, a soaking tub, separate shower, and ceramic tile flooring. The additional bedrooms are generously sized, while the thoughtfully designed laundry room includes a convenient utility sink. Additional features include efficient natural gas heat, central air conditioning, a tankless gas instant hot water heater, ceramic tile bathrooms, an attached two-car garage with a professionally finished epoxy floor, and a large screened porch perfect for enjoying your morning coffee or relaxing at the end of the day. Residents of Clark's Rest enjoy beautifully maintained sidewalks, walking trails, playgrounds, community amenities, and a welcoming neighborhood atmosphere, all within one of Southern Maryland's most desirable communities. This exceptional home offers the perfect combination of style, functionality, and location—an opportunity you won't want to miss.

41379 Margrove Cir, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$699,900
3 Beds 2 Baths
If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for entertaining guests or creating lasting memories with family and friends. This move-in-ready home features a new HVAC system, beautifully updated bathrooms, brand-new flooring throughout, an encapsulated crawl space, and countless additional upgrades that offer both comfort and peace of mind. Opportunities like this don't come around often—schedule your showing today before it's gone!

18937 Hodges Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$375,000
3 Beds 2 Baths
Owned by the same family since the 1960s, this 3-bedroom, 2-bath rambler has been lovingly maintained and is ready for its next chapter. This one already has the space, setting, and major improvements to make the possibilities exciting. The larger updates have already been taken care of, including a newer roof, siding, windows, new septic (early 2000's) and a 21x15 composite deck overlooking the backyard. The HVAC and furnace have also been serviced annually, allowing the next owner to focus on fresh paint, personal touches, and making the home their own. Inside, the oversized 25x12 owner’s suite includes a private bath and plenty of room for a king-size bed and sitting area. A spacious 35x12.5 addition with two separate entrances offers incredible flexibility for a family room, home office, playroom, guest space, in-law setup, studio, or hobby area. The layout also provides an opportunity to expand the kitchen and create an even larger gathering space. Original HARDWOOD flooring is under the carpet in all three bedrooms, just waiting to be uncovered and restored. Situated on a level, fully fenced lot just under half an acre, nearly every inch of the property is usable. There is plenty of room for pets, gardening, entertaining, outdoor play, or even a future pool. A storage shed and driveway parking for at least five vehicles add even more convenience. Two private community beaches with sweeping view of the Potomac River are just a short walk from the front door, and there is no HOA. Bring your fishing poles, beach chairs, and imagination. This one feels like home!

43927 Lanedon Dr, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$674,000
4 Beds 4 Baths
Nestled in the serene community of Chestnut Hills of Leonardtown, this charming Colonial-style home offers a perfect blend of comfort and privacy. With 4 spacious bedrooms and 3.5 bathrooms, this residence spans an impressive 3,381 square feet, providing ample space for both relaxation and entertaining. Step inside to discover a warm and inviting interior. The open floor plan seamlessly connects the kitchen, dining area, and living spaces, making it ideal for gatherings. The kitchen is a chef's dream, complete with a butcher block island, modern appliances, generous cabinetry and plenty of counter space for meal prep. Crown moldings and chair rail add a touch of sophistication to the ambiance. The cozy family room, highlighted by a woodburning fireplace with glass doors and a mantel, creates a perfect spot for unwinding after a long winters day. The primary suite offers a very spacious private retreat with, large walk in closet and an en-suite bath, ensuring comfort and convenience. Venture outside to enjoy the expansive 2.89-acre lot, where nature surrounds you. The rear of the property boasts a beautiful retaining wall, a fire pit and backs up to Forest Retention Area providing a sense of continual privacy and tranquility. The outdoor space is perfect for entertaining or simply enjoying the peaceful views of the woods. Relax on the front porch, rear screened porch or deck, ideal for morning coffee or evening gatherings. The home also features a fully finished basement with both interior and outside entrances, offering additional living space, private gym area, private office, craft room or storage options. Create you own movie nights in the full theater room with projector and surround sound, which the equipment conveys. With an attached two-car garage and driveway, parking is a breeze. New roof and HVAC unit replaced in 2019. New water heater replaced in 2020. New insulated garage door 2026. Insulated crawl space and attic. French drainage system installed the home's perimeter. Additional features include a main floor laundry area and a security system for added peace of mind. As part of the Chestnut Hills community, residents have access to amenities, including rec field, basketball court, playground, and picnic areas, making it a wonderful place to call home. This property is not just a house; it’s a place where memories are made, and comfort is found. Experience the perfect blend of indoor and outdoor living in this delightful home.

20750 Deer Wood Park Dr, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

$350,000
5 Beds 2 Baths
Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant room for outdoor recreation, gardening, equipment storage, animals or creating your own private retreat. The property may also appeal to builders, investors or buyers exploring potential subdivision or development opportunities, subject to county zoning, approvals, utilities and feasibility studies. Inside, the home offers a flexible five-bedroom layout with space for home offices, guest rooms, multigenerational living or hobby areas. Its rambler-style design provides convenient everyday living with minimal stairs. Located near historic Leonardtown, local shopping, dining, schools, medical facilities and Southern Maryland commuter routes, this property is ideal for buyers seeking acreage without sacrificing access to nearby amenities. Bring your vision and discover the potential of this distinctive Leonardtown property.

23011 Newtowne Neck Rd, Leonardtown

Listing courtesy of Samson Properties. Contact: (703) 378-8810

$680,000
4 Beds 2 Baths
Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2018, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers four well-appointed bedrooms, including a convenient entry-level bedroom, perfect for guests or those seeking single-level living. The primary suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, providing a serene retreat at the end of the day. Additional interior highlights include plush carpeting, elegant hardwood floors, and ceiling fans that enhance comfort throughout the seasons. For those who appreciate technology, the home is equipped with a sound system, ensuring that your favorite tunes accompany you in every room. Outside, the property features a screened in porch, perfect for outdoor relaxation while enjoying the tranquility of your surroundings. The oversized detached garage offers ample space for vehicles and storage and has heat/ac, electricity and plumbing while complemented by a paved driveway for easy access. There is ample parking space for vehicles, campers, and more! Enjoy the peace of country living while being just a short drive from local amenities, shopping, and dining options. Don't miss the opportunity to make this beautiful residence your forever home!

25375 Loveville Rd, Leonardtown

Listing courtesy of RMG Realty. Contact: 5407091011

$924,999
4 Beds 3 Baths
Discover the charm of this lovely waterfront ranch-style home, located in the Mulberrys on Breton Bay neighborhood. With 2,550 sq. ft. of living space, this home features four spacious bedrooms and 2.5 bathrooms, ensuring comfort for all. Open concept living on the main floor includes spacious family/dining area, primary bedroom and updated kitchen with custom Woodburn soft close cabinetry, under cabinet lighting, stainless appliances, bar seating and large pantry. Step into the large and inviting main level primary bedroom, where panoramic bay sunrise views greet you each morning. The primary bath is updated with ceramic tiled walk-in shower and large walk-in closet.. Enjoy cozy winter evenings by the gas fireplace in the open living area adorned with recessed lighting, custom built-in bench seat cabinetry and solid hardwood floors. Outside, the half-acre lot offers deep water direct access to your private dock with water, electric and boat lift, perfect for boating, fishing, crabbing, or simply soaking in the breathtaking water views. The deck and patio provide additional outdoor living space, ideal for summer barbecues or quiet evenings under the stars. An attached garage and circular driveway add convenience at your fingertips. A quick boat ride brings you to the Leonardtown Wharf where you can enjoy the public park events or go into Historic Downtown Leonardtown to enjoy the many shops and restaurants. Breton Bay Golf and Country Club is just a short drive away which has a beautiful 18 hole public course. There is also a swimming pool and tennis courts with memberships available. Located in a vibrant neighborhood of custom built homes, amenities like basketball and tennis/pickleball courts and boat storage area makes this home a true retreat. Embrace the lifestyle you’ve always dreamed of in this beautiful bayfront haven.

41402 Philip Ln, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

$359,777
4 Beds 2 Baths
Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished lower level expands the living space with an additional family room, two more bedrooms, and a second full bathroom—ideal for guests, a home office, or multi-generational living. With great bones and endless possibilities, this home is ready for your personal touches and updates. Fantastic location just minutes from shops, restaurants, schools, and waterfront amenities on Brenton Bay. Don't miss this rare opportunity to invest in one of Leonardtown's most desirable neighborhoods and create lasting value. Property is being sold strictly as-is. Schedule a showing today!

40743 Magee Dr, Leonardtown

Listing courtesy of Real of Pennsylvania. Contact: 8554500442

$575,000
4 Beds 3 Baths
Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area and into the kitchen. The kitchen was completely renovated in 2025 and features quartz counters, soft close cabinetry, tile floors, and stainless appliances. There's plenty of storage and counter space for easy meal prep and entertaining. For the grilling enthusiasts, a screened porch is a few steps away from the kitchen making it convenient for grilling and outdoor dining. As you progress down the hall, you're greeted with two spacious bedrooms, and a hall bathroom that was renovated in 2024 with a timeless design. At the end of the hall is the generous sized owners bedroom, complete with multiple closets, a dressing area, and an ensuite bathroom that was also renovated in 2024 with a sleek, modern motif. The owners suite features a private covered deck overlooking the back yard and farm land, making it a quiet retreat for relaxing after a long day. The lower level is partially finished with a 4th bedroom, 3rd full bathroom, and spacious second family room. The family room enjoys a bar for entertaining, as well as access to the two car garage. The remaining lower level contains laundry, built-in storage cabinets, and tons of storage space! The heat pump was replaced in 2024, and the roof was replaced with 40 year shingles in 2010. A Mini Fridge in the basement bar and a refrigerator in the garage convey. This home is uniquely located in Breton Bay, and enjoys views of the golf course, and views of the farmland behind the home. It's also within walking distance to the Breton Bay Clubhouse, and a mere 7 minutes to downtown Leonardtown. The community enjoys a beach area and playground for a minimal annual fee. Membership to the Breton Bay Country Club grants access to the pool and tennis courts. Welcome Home!

22010 Society Hill Rd, Leonardtown

Listing courtesy of Compass. Contact: (703) 229-8935

$750,000
3 Beds 3 Baths
Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally generous 37' x 8' rear porch, where you can relax and take in the peaceful waterfront scenery. Recent updates include new siding, a new roof, and a new gutter system. The side-load garage includes a staircase leading to a large upper-level storage area. Perfectly situated next to the neighborhood beach and pier, this property offers easy access to the waterfront and outdoor recreation. It's also within walking distance of the Breton Bay Golf & Country Club, where memberships are available for golf, swimming, and dining at the clubhouse restaurant. Whether you're looking for a year-round residence or a weekend retreat, this exceptional home combines stunning views, thoughtful updates, and an unbeatable location in one of Breton Bay's most desirable settings.

40579 Port Pl, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

$615,000
5 Beds 4 Baths
Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so much more just inside the walls! Outside the walls of the home, features a shed, fenced in backyard, a beautifully manicured lawn watered by an in-ground irrigation system and several flower beds for all a plant enthusiast could ever ask for! Situated in the subdivision known as The Villages at Leonardtown, we are only minutes from all the shops, dining, and attractions Leonardtown has to offer, with a further drive to all the shops, attractions, dining near Pax River Naval Base and the surrounding area offers. Come take a look as this one won't last for long!

23620 Gunnell Dr, Leonardtown

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500

$700,000
4 Beds 4 Baths
Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the cul-de-sac. From the moment you arrive, you'll appreciate the welcoming community—where neighbors gather for evening walks, children ride bikes, and the sense of home extends well beyond the property lines. Inside, the updated kitchen serves as the heart of the home, featuring a large center island with a built-in beverage refrigerator, beautiful finishes, and durable tile flooring that flows into the bright, bumped-out breakfast area overlooking the backyard. Multiple living and entertaining spaces provide the flexibility today's buyers are looking for, whether hosting family gatherings or enjoying everyday life. Step outside to your private backyard retreat. The fully fenced, level yard offers plenty of room for children, pets, gardening, or outdoor games, while the expansive deck and covered patio beneath a pergola create the perfect spaces for entertaining or relaxing. A large storage shed provides additional room for lawn equipment, tools, and seasonal storage. Upstairs, the oversized primary suite is a true retreat, complete with a spacious walk-in closet featuring laundry hookups for added convenience. Three additional generously sized bedrooms, each with ample closet space, complete the upper level. The finished basement expands the home's versatility with a spacious recreation area, full bathroom, and a bonus room—ideal for a home office, fitness room, playroom, hobby space, or guest accommodations. An unfinished storage area ensures you'll have room for everything. Completing the home is a generously sized side-load two-car garage. Offering the space to grow, the updates buyers appreciate, and a location that's consistently in demand, 21395 Fairwood Ct. delivers the ideal combination of comfort, functionality, and community. If you've been searching for a home that offers room to spread out without sacrificing convenience, this Leonardtown property is one you won't want to miss.

21395 Fairwood Ct, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$469,900
3 Beds 3 Baths
Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features hardwood flooring throughout most of the space, installed in 2019. The kitchen is appointed with cherry cathedral-style cabinetry, Corian countertops, an L-shaped center island, an Americast sink, and indirect lighting above and below the cabinets. The full suite of stainless-steel appliances includes a refrigerator with ice and water in the door, range, dishwasher, and built-in microwave. Hardwood stairs with white risers and balusters connect the home’s two levels. The foyer welcomes guests with 12-by-12-inch ceramic-marble tile and a fiberglass front door featuring sidelights and decorative leaded glass. The spacious primary bedroom includes a walk-in closet with a distinctive cedar ceiling. Its private bathroom offers a jetted soaking tub and separate shower. The second bedroom features luxury vinyl plank flooring, the third bedroom is carpeted, and the hall bathroom includes a tub-and-shower combination. Downstairs, the finished living area offers luxury vinyl plank flooring and a wood-burning fireplace surrounded by brick painted a stylish red. This level also includes a full bathroom with a tub-and-shower combination, a newer washer and dryer, and flexible space for relaxing, entertaining, working, or accommodating guests. The home is also wired for an alarm system. Outdoor living is a standout feature. A composite deck with vinyl pickets and handrails overlooks the fully fenced backyard, while the patio beneath the deck provides additional covered entertaining space. The backyard also includes a tiki-style entertainment area, a three-year-old 12-by-24-foot Intex above-ground pool, and a very large storage shed offering plenty of room for lawn equipment, tools, recreational gear, and seasonal items. Major improvements include the roof and hardwood flooring in 2019, HVAC in 2017, and water heater in 2015. Only two people have occupied the home since 2015, reflecting the light use and care it has received. With **NO HOA**, a level corner lot, an oversized garage, a blacktop driveway, abundant storage, extensive outdoor amenities, and a glimpse of the Potomac River, this home delivers the space and freedom to enjoy your property your way.

43954 Main Way Rd, Leonardtown

Listing courtesy of Keller Williams Flagship. Contact:

$619,900
4 Beds 3 Baths
Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is designed for everyday living with comfortable gathering spaces, an open flow, and room to make the home your own. Meadows at Town Run II is one of Leonardtown’s newest opportunities, with only 12 single-family homes planned in this section. Enjoy convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Planned amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Estimated delivery for early 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. This is one of only 12 single-family homes to be built in Meadows at Town Run II, making it a rare opportunity in one of Leonardtown’s most convenient communities. Enjoy close proximity to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers use QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 5, available selections, incentives, and delivery timing. Photos may show a previously built Bell model or similar QBHI home and are for example purposes only. Actual home, features, finishes, options, and selections may vary.

42096 Wildflower Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

$609,900
4 Beds 3 Baths
New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s suite includes generous closet space and a private bath, with three additional bedrooms, a full bath, and convenient second-floor laundry. Estimated delivery for early 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers use QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 4, available selections, incentives, and delivery timing. Meadows at Town Run II is located in Leonardtown with convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. This section will include only 12 single-family homes. Planned community amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Former decorated Mattingly model shown for example purposes only. Photos do not represent the actual home on Lot 4. Actual home, features, finishes, options, selections, and pricing may vary.

42102 Wildflower Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

$614,900
4 Beds 3 Baths
New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing. The Fenwick offers a smart, comfortable layout with a spacious family room, kitchen and breakfast area, 9-foot ceilings, granite/quartz countertops, 42-inch cabinets, stainless steel appliances, and Quality Built Homes’ signature craftsmanship throughout. Upstairs, the primary suite features a private en suite bath with dual vanities, soaking tub, and QBHI’s Deluxe Shower. Two additional bedrooms, a full bath, and second-floor laundry complete the upper level. Meadows at Town Run II is one of Leonardtown’s newest opportunities, with only 12 single-family homes planned in this section. Planned amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Estimated delivery for early 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers choose QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II in Leonardtown is open Thursday through Sunday from 11 AM to 4 PM. Schedule your appointment today. Photos shown are of a previous Fenwick model home and are provided as an example of what can be built. Actual home, features, finishes, options, upgrades, selections, and layout may vary.

42108 Wildflower Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

$629,900
4 Beds 3 Baths
To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start. This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an inviting layout designed for everyday living and entertaining. The main level offers a spacious family room that flows seamlessly into the kitchen and breakfast area, along with a formal dining room and living room for added flexibility. Upstairs, the primary suite includes generous closet space and a private en suite bath. Three additional bedrooms, a full bath, and convenient second-floor laundry complete the upper level. Located in the desirable Meadows at Town Run II community in Leonardtown, this homesite offers convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Now is the perfect time to get in early! Buyers may still have the opportunity to select interior options, finishes, and personal selections depending on timing and construction milestones. Estimated delivery for for early 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers choose to work with QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II in Leonardtown is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about building in Meadows at Town Run II. ***Please note***Photos are of a previously built Clarke model home and are shown for illustrative purposes only. Photos do not represent the actual home on Lot 7. Actual home, features, finishes, colors, selections, landscaping, furnishings, and options may vary. Some items shown may be upgrades and are not included in the base price.

42084 Wildflower Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

$465,000
3 Beds 2 Baths
This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one in the community. Private Pier: Sturdy, deep-water access steps from your back door. New Rip Rap: Fresh shoreline reinforcement ensures long-term erosion protection. Large propane tank which is almost full for newly installed gas log fireplace & furnace. All supporting floor beams in the crawl space have been addressed. Blank Canvas Interior: Down-to-the-studs flexibility ready for your custom layout. Generous Footprint: Over 1,600 square feet of customizable living space facing a waterfront picturesque view. This home will be perfect for the generational waterman looking to be in the Potomac River within just a few minutes or the city resident who is looking to escape for the weekend. Several homes on the street have had a complete overhaul and the home next door is just about completed. Now is your turn to create your waterfront dream!

18800 Mckays Beach Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4432956123

$399,000
Build your dream home in one of Leonardtown's most desirable locations! Welcome to Parcel 323, Tract 2, a newly created homesite just moments from the heart of historic downtown Leonardtown. Perfectly positioned to take advantage of beautiful water views of Breton Bay, this exceptional parcel offers the opportunity to enjoy the best of small-town coastal living. Imagine strolling to Leonardtown's charming shops, restaurants, coffee houses, wineries, and waterfront Wharf, where you'll enjoy year-round events, live music, kayaking, and breathtaking sunsets. Whether you're looking to build your primary residence or a weekend retreat, this property offers an unbeatable combination of convenience, scenic surroundings, and walkable lifestyle. A recent survey has already been completed by the sellers and markers are present and visible. Buyers are responsible for verifying all building requirements, permitted uses, utility connection and development plans with the Town of Leonardtown and the St. Mary's County Permitting Office. Don't miss this rare opportunity to build in one of Southern Maryland's most sought-after waterfront communities while enjoying the charm, history, and vibrant atmosphere of downtown Leonardtown.

Parcel 323 Tract 2 Washington Street, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$599,900
4 Beds 4 Baths
Charming Home in Prime Leonardtown Location This inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room connects through a butler’s pantry to a full walk-in pantry and flows into a modern kitchen featuring granite counters, upgraded cabinetry, stylish subway tile backsplash, large center island, gas cooktop, double wall ovens, and a premium Samsung Bespoke 4-drawer refrigerator with beverage center. The kitchen flows to an eat-in area and a cozy family room with gas fireplace flanked by beautiful custom built-ins. A powder room completes the main level. Luxury vinyl plank flooring runs throughout the main level and upstairs hallway, with hardwood stairs. Upstairs, the spacious primary suite includes a deluxe bathroom with dual sinks, soaking tub, ceramic-tiled shower, and a large walk-in closet. Three additional generous bedrooms, another full bath, and a sizable laundry room round out the upper level. The finished lower level offers a flex room, family room, full bath, and excellent storage. Outside, enjoy a composite deck, fully fenced yard, and firepit — perfect for relaxing or entertaining. Additional highlights include a 2-car garage and owned solar panels that keep utility bills impressively low. Enjoy resort-style living with neighborhood amenities including a spacious clubhouse, a 3,500 sq ft pool with separate kiddie pool, tennis and basketball courts, playground, and walking trails. Ideal location, thoughtful layout, and move-in ready condition — this home checks every box.

41444 Osborne Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$485,000
4 Beds 3 Baths
Buyers, come take a look. The estate just dropped the price by $20,000 This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's bathroom shower has a leak and will probably need to be replaced. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and 2 full baths and the laundry room on the upper level. The main level features an eat in kitchen, formal dining room, separate living room and a family room and a half bath/powder room. The unfinished basement features a 3-piece rough-in for another full bathroom. On the outside, there's a deck off the kitchen and the backyard has a vinyl privacy fence. Out front, there's a covered wrap around front porch and a side entrance too.

40659 Klear Ct, Leonardtown

Listing courtesy of Baldus Real Estate, Inc.. Contact:

$629,000
4 Beds 3 Baths
CREDIT FOR REPAIRS!! New Lower Price!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious office area, a flexible bonus room, and a fascinating secret room hidden away for ultimate privacy or storage. Basement bathroom rough in ready for your unique finishes. Enjoy peace of mind with a brand-new tankless hot water heater installed at the end of 2025. Outside, the premium, fully fenced backyard boasts a 6-foot white vinyl privacy fence, offering a pristine and secure oasis for pets, play, or relaxing. Don't miss this one-of-a-kind home in a fantastic location! Situated in the highly sought after Leonards Grant neighborhood with tennis court, basketball court, community pool, large green, multiple playgrounds and recreation center. Within walking distance to Elementary School and very close to the amazing Leonardtown Square with restaurants, water views , and shops

23636 Hansel Ct, Leonardtown

Listing courtesy of Taylor Properties. Contact:

$1,700,000
5 Beds 4 Baths
Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. Enjoy 1,545 feet of bay-front water life. Kayakers, yachters, dolphin enthusiasts, fishers, crabbers, and star-gazers are just a few who may find interest in this exemplary waterfront gem. The centerpiece of the outdoor living experience is the spectacular saltwater pool, thoughtfully designed for both relaxation and entertaining. The saltwater pool is finished with premium Wet Edge Premier Stone and Artistic Paver tiles, (featuring embedded seashells sourced from Miami). The tanning ledge measures approximately 8x16' providing the perfect place to lounge and enjoy waterfront views, while a diving board adds to the fun. A dedicated pool pump house and separate dual pool storage unit with its own half bath supports the pool operation. Water enthusiasts will appreciate the exceptional marine amenities. Walking down the hill from the residence leads to a private boathouse and pier system designed with serious boaters in mind. The pier features new stringers, updated power and water service, two slips including the boathouse, and one open slip, a fish cleaning station, and kayak launch area. Low water depth at the end of the pier averages approximately eight feet, making this deep-water location highly desirable for larger vessels and year-round boating. The boathouse, along with the pier, pool house, and detached garage, are all serviced through a dedicated electrical panel system. Water is also available on the pier. Inside, the home has undergone substantial improvements over the years, including a complete transformation of the kitchen and dining areas, creating a stunning gourmet gathering space that serves as the heart of the home. Updated Andersen windows, updated flooring, fresh interior paint, and a beautifully finished laundry and utility room further enhance the home’s appeal. The impressive enclosed sunroom, encompassing approximately 440 square feet, offers year-round enjoyment and flexible living space while showcasing the property’s incredible waterfront views in all seasons. Additional improvements include HardiePlank fiber cement siding, a whole-house generator capable of operating the kitchen and well systems during outages, and a detached 2.5-car garage with a raised floor to improve site grading. The garage offers exceptional storage and future potential for additional finished space should a buyer desire to build up. The well is approximately eight years old. When drilled, the well and pump were upgraded to provide for the additional water needs of the pool, pier and future lawn irrigation. The laundry and utility area features a Navien boiler installed in 2016, providing domestic hot water as well as support for the home’s heating systems. For added value and future convenience, the sellers are in the process of connecting the property to public sewer, which is available within the property. We cannot wait for you to come see the lifestyle that Combs Creek Way has to offer you.

40115 Combs Creek Way, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

$288,900
Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or creating the family compound you've all been dreaming of. This beautiful land is conveniently positioned just off Rt. 5, in a prime location between St. Mary's State Park and the charming St. Mary's County seat, Leonardtown. Note that the location is not actually ON Whirlwind Rd; it is best accessed at the end of Redgate Ln. Future potential to create access from both Rt. 5 and Redgate Ln. Call for more details!

Whirlwind Rd, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

$539,900
4 Beds 3 Baths
Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access, Leonardtown Square, restaurants, shopping, and PAX River Naval Air Station. This home features a new roof installed in 2026, a high-efficiency oil furnace/hot water system approximately two years old, endless hot water capability, and a transferable warranty on the furnace system. The insulated 2-car garage adds excellent flexibility with its own mini-split system for year-round heating and cooling, a large attic storage area above the garage, and 50-amp RV electrical service. Spacious outdoor living areas provide the perfect setting for relaxing, entertaining, and enjoying the mature landscaping of this established neighborhood. With no HOA, a sought-after golf community location, nearby beach and pier access, and the privacy of cul-de-sac living, this property offers a wonderful opportunity to enjoy the Breton Bay lifestyle. More photos and details coming soon!

40777 Center 40 Cir, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169