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Gene Sementilli GRI, SRS, CRS, PSA, ePRO, MRP, ABR,RENE
301-807-7797

Leonardtown MD Real Estate & Homes for Sale

38 Properties Found

The median home value in Leonardtown, MD is $581,500. This is higher than the county median home value of $325,000. The national median home value is $308,980. The average price of homes sold in Leonardtown, MD is $581,500. Approximately 60% of Leonardtown homes are owned, compared to 33% rented, while 7% are vacant. Leonardtown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Leonardtown real estate agent to arrange a tour today!
Learn more about Leonardtown Real Estate.


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Beds:
5
Baths:
3 Full
Sq.Ft.:
3,500
Status:
NEW LISTING
MLS#:
MDSM2024896
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTNUT HILLS
Lot size:
4.97 Acres
Year built:
2001
Courtesy: RE/MAX One
View additional info

Move Right In and Start Living the Leonardtown Lifestyle! Welcome to 20620 Laurel Court - where modern luxury meets small town charm on nearly 5 private acres in sought-after Leonardtown, Maryland. Nestled in a peaceful cul-de-sac, this thoughtfully reimagined home offers over 3,000 sq ft of exceptional living space with 5 bedrooms and 3 full baths - including a convenient main level bedroom and full bath, perfect for guests or multi-generational living. The heart of the home is the fully renovated and reconfigured main level (2024), featuring a true chefs kitchen with custom shaker-style cabinetry loaded with innovative storage solutions - even space for your pets kennel! Premium finishes include wide-plank luxury vinyl plank flooring, quartz countertops, high-end Samsung and GE Profile appliances, Kraus Kore undermount sink system, Moen smart faucet with voice control, and an oversized center island induction cooktop that makes entertaining effortless. Every detail was carefully chosen for beauty, efficiency, and durability. Designed for versatility, this home features two separate staircases leading to the upper level, offering convenience, privacy, and a natural flow between spaces. Upstairs, youll find a spacious loft, convenient laundry room (with new stackable washer/dryer), and the luxurious owners retreat, complete with sitting area, gas stove, walk-in closet, and spa-like en-suite bath. The large loft adds flexible space for work or play, and the conveniently located upstairs laundry (with new stackable washer and dryer) keeps everyday chores simple. This home is fully equipped with state-of-the-art smart home features - including Lutron Caseta voice-activated lighting, Ring doorbell and camera system, Schlage digital locks, Rain Bird 11-zone WiFi irrigation, and a fully pre-wired 5.2 surround sound family room. Additional features include: 4-year-old roof / Tankless water heater / Garage door WiFi controls / New well pressure tank / ERV basement ventilation system for radon control / New LED lighting and ceiling fans throughout / Outdoor fire pit pad wired for a hot tub. Why Leonardtown? Living here means enjoying the perfect blend of historic charm, waterfront beauty, and modern conveniences. Leonardtowns picturesque downtown offers boutique shops, award-winning restaurants, local art galleries, and year-round community events that bring neighbors and visitors together. Parents of school aged students appreciate the highly rated St. Marys County schools, while commuters value the easy access to PAX River Naval Air Station and nearby shopping and dining options in California, MD. This is your rare opportunity to own a turn-key home offering peace, privacy, and convenience - all just minutes from the heart of Leonardtown. Don't miss your chance - schedule your private showing today and experience all that 20620 Laurel Court has to offer!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,488
Status:
NEW LISTING
MLS#:
MDSM2025300
Type:
Single Family, Single Family-Detached
Subdivision:
MAYDEL MANOR
Lot size:
1.05 Acres
Year built:
1955
Courtesy: CENTURY 21 New Millennium
View additional info

A rare opportunity on the shores of Breton Bay, presents a canvas for transformation. This expansive 1.05 acre waterfront boast 164 feet of private shoreline and delivers breathtaking sunset panoramas. This classic 1955 construction offers endless renovation potential. With 1468 square feet of main living space and a 1247 square foot basement, this 3 bedroom 2 bathroom home shows potential for amazing views and waterfront living. The well has a recent water quality certification. The owner will make repairs to the septic system including replacing the tank with a BAT septic system and replacing the distribution box due to its age. The Grant application has been submitted. The exceptional waterfront property presents a canvas for transformation. Whether you're an investor seeking development potential, a builder looking for your next signature project, or a homeowner ready to craft your personal waterfront sanctuary, this rare offering delivers a combination of acreage, shoreline and sunset exposure on Breton Bay. This property is being sold as is.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,379
Status:
NEW LISTING
MLS#:
MDSM2025460
Type:
Townhouse
Subdivision:
CLARK'S REST
Lot size:
0.05 Acres
Year built:
2022
Courtesy: RE/MAX Realty Group
View additional info

Location is key.... Not just in Leonardtown but in the community itself. Through every window of the rear of this house is the picturesque setting of the wooded tree line and abundant privacy, not often found in Town Home living. Upgrades to this home from original build include: Level 4 LVP on main level, Window sill and molding surround on all windows, Custom blinds, Ceiling fan install on all bedrooms and Family Room, My Q garage openers controlled from app in your phone, Replacement of all commode's to elongated commode's, replaced half bath vanity sink, Lifetime warranty gutter guard install, Pulls and knob install on all cabinetry (Kitchen and baths), Rear deck installed, Replaced kitchen refrigerator, Primary bedroom closet organizer's, and landscaping in front. This home is just under three years old and comes with the peace of mind of a Builder's 2-10 Warranty that's valid for an additional seven years. Clarks Rest residents enjoy a range of community amenities, including the community pool, a baby/toddler pool, sports courts (basketball and tennis), a beautiful clubhouse, walking nature trails, playgrounds, and open green spaces for relaxation and play. Experience the best of Leonardtown living with the seasonal Leonardtown Trolley. Hop on right from your neighborhood sidewalk and enjoy the ride around town with stops at the local winery, restaurants, pubs, coffee shops, charming bakeries, and of course, the Leonardtown Wharf. Spend your free time at nearby parks, beaches, museums, boardwalks, and theaters. Located just a short drive from Patuxent Naval Air Station (PAX), this home also offers access to excellent Leonardtown schools: Leonardtown High, Leonardtown Middle, and Leonardtown Elementary. Clarks Rest is a "walkable" community providing sidewalks throughout that also lead to the charming downtown with many stops along the way, including the library, schools, parks, and more. Love where you live here in Leonardtown, a most convenient place!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,330
Status:
NEW LISTING
MLS#:
MDSM2025256
Type:
Single Family, Single Family-Detached
Subdivision:
ACADEMY HILLS
Lot size:
0.25 Acres
Year built:
2006
Courtesy: RE/MAX Realty Group
View additional info

Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn and shrubs in their pristine state or use as a workshop. Get your tour scheduled soon so you don't miss out.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,040
Status:
NEW LISTING
MLS#:
MDSM2025400
Type:
Single Family, Single Family-Detached
Subdivision:
CHAPPELEARS
Lot size:
0.34 Acres
Year built:
2005
Courtesy: RE/MAX One
View additional info

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

Open House:

Saturday, 6/21 1:00-2:00PM

Beds:
3
Baths:
2 Full
Sq.Ft.:
984
Status:
NEW LISTING
MLS#:
MDSM2023732
Type:
Single Family, Single Family-Detached
Subdivision:
HOLLY OAKS
Lot size:
0.6 Acres
Year built:
1978
Courtesy: Blackwell Real Estate, LLC
View additional info

Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location-all with no HOA. Inside, youll find a bright and open layout featuring wide plank flooring, recessed lighting, and an upgraded kitchen with granite countertops, stainless steel appliances, and stylish two tone cabinetry. Just off the kitchen, a back deck overlooks the large, fully fenced yard-perfect for relaxing, entertaining, or letting pets roam freely. The main level offers three bedrooms and two full bathrooms, both updated with bold, modern tile and clean finishes. Downstairs, the walk-out basement adds nearly 800 square feet of flexible space for a rec room, home gym, playroom, or storage. One of the standout features of this property is the oversized detached garage with room for four vehicles, tools, or workshop space. Additional recent upgrades include a new roof, new HVAC system, and a new deep well. Located just minutes from downtown Leonardtown, this home is close to local shops, restaurants, waterfront parks, and community events. Known for its small-town charm and strong sense of community, Leonardtown offers a relaxed lifestyle with easy access to everything Southern Maryland has to offer. This property also qualifies for special financing through the Maryland Mortgage Program. For more information, contact Natalie Miller with the Gary Pierpont & Team at First Home Mortgage.

Beds:
6
Baths:
3 Full/1 Half
Sq.Ft.:
5,888
Status:
NEW LISTING
MLS#:
MDSM2025294
Type:
Single Family, Single Family-Detached
Subdivision:
BIG CHESTNUT
Lot size:
1.52 Acres
Year built:
2020
Courtesy: RE/MAX Realty Group
View additional info

Luxury, Space, and Sophistication - All in One Remarkable Property! Prepare to be impressed by this meticulously maintained almost 7,000 sq ft estate-a rare gem that blends luxury, comfort, and functionality in every detail. If your current home lacks character or space, this extraordinary residence will exceed all your expectations! Interior Highlights: � Gourmet Kitchen with oversized island, walk-in pantry featuring a second island and refrigerator � Wet bar/Coffee station and recessed lighting throughout � Main-level office with custom built-in desk and counters � Spacious dining room and large breakfast area perfect for gatherings � Stainless steel appliances and cozy propane fireplace � Cat 5 wiring throughout for seamless connectivity � Laundry rooms on all three levels for ultimate convenience � Two staircases provide easy access to the second floor Owners Retreat: � Expansive Owners Suite with a massive walk-in closet featuring an island with built-in cabinetry � Spa-like ensuite bath with rain showerhead, dual sprayers, and tiled ledge Bedroom Features: � 6 spacious bedrooms, 5 equipped with custom closet organizers Entertainment & Lifestyle: � Sunroom leading to a covered porch-perfect for year-round relaxation � Theatre room with projector and bar in the basement � 20 x 40 chlorinated pool with a 9� deep sundeck, automatic cover, and expansive patio � Blink security system with cameras and spotlights � Safe area under front porch � Stunning foyer chandelier that makes a grand first impression Garage & Storage: � Attached 3-car garage with remote door openers � Detached 42 x 38 garage/workshop-ideal for storage, hobbies, or a man cave Bonus Features: � Tankless water heater � Full 18-zone yard irrigation system � Gutters piped underground � Includes an additional 4+ acre lot-a rare opportunity to expand or enjoy added privacy This home truly has everything-and its all been immaculately maintained. Private showings available by appointment only with a minimum of one hour notice.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,697
Status:
NEW LISTING
MLS#:
MDSM2024680
Type:
Single Family, Single Family-Detached
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.3 Acres
Year built:
2005
Courtesy: RE/MAX One
View additional info

Welcome home to this beautifully updated Colonial located in a charming and quiet Leonardtown neighborhood-just minutes from local restaurants, shopping, and all the conveniences of town living. Freshly painted throughout and featuring brand-new carpet, this 4-bedroom, 2.5-bath gem is move-in ready and full of modern upgrades. The heart of the home is a gourmet kitchen with upgraded stainless steel appliances, granite countertops, and ample cabinet space-perfect for both everyday living and entertaining. Upstairs, youll find a HUGE primary suite complete with a en-suite bath and 2 closets, along with three additional spacious bedrooms and bathroom. The basement is unfinished but already roughed in! Finish, or not, to your liking! Step outside to enjoy a large, beautiful deck overlooking a fully fenced backyard. Added Bonus...Home has Hardwire Ethernet lines in every room of the house!! Dont miss your chance to own this well-maintained home in a sought-after location in Leonardtown. Schedule your private showing today!

Beds:
4
Baths:
4 Full
Sq.Ft.:
4,829
Status:
Active
MLS#:
MDSM2025060
Type:
Single Family, Single Family-Detached
Subdivision:
CLARK'S REST
Lot size:
0.19 Acres
Year built:
2024
Courtesy: EXP Realty, LLC
View additional info

Stunning 4 Bed / 4 Bath Ranch Rambler in Sought-After Clarks Rest Community Welcome to your dream home! Nestled in the highly desirable Clarks Rest community, this stunning 4-bedroom, 4-bath Ranch Rambler is only one year old and loaded with upgrades with exceptional curb appeal and luxurious features throughout, this is a rare find that wont last long. This modern home blends comfort, style, and convenience-all just minutes from downtown Leonardtown's shopping, dining, waterfront activities and entertainment. Enjoy main-level living at its finest with a spacious FIRST FLOOR MASTER complete with ensuite with soaking tub and walk in shower and additional nice sized bedroom with bay window, a dedicated office, and an open-concept kitchen that flows seamlessly into the dining area, family room with a beautiful 60-inch electric fireplace. The kitchen boasts stainless steel Energy Star appliances, and stove with built in Air fryer, granite counter tops, sleek finishes, and ample 42-inch cabinets, includes an extended 15x10 bonus morning room offering an abundance of natural light and perfect for relaxed gatherings. The entire home has Luxury Vinyl Plank except in the bedrooms. The fully finished basement offers incredible versatility with a large recreation room, a SOUNDPROOF theater room, a full bedroom and bathroom, and generous storage space. Upstairs, youll find a private loft area featuring another bedroom and full bath, along with a flex room ideal for a home office, game room, or a guest retreat. The backyard is fully fenced with Vinyl Fence perfect for your outdoor entertainment and privacy. Community amenities are top-notch and include a clubhouse, outdoor pool, tennis and basketball courts, and a playground-perfect for an active lifestyle and the kids This turn-key home offers everything you need and more-dont miss the opportunity to make it yours!

Open House:

Friday, 6/20 4:00-6:00PM

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,500
Status:
Active
MLS#:
MDSM2025004
Type:
Single Family, Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.22 Acres
Year built:
2010
Courtesy: RE/MAX One
View additional info
Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,686
Status:
Active
MLS#:
MDSM2024976
Type:
Single Family, Single Family-Detached
Subdivision:
CLARK'S REST
Lot size:
0.16 Acres
Year built:
2019
Courtesy: RE/MAX United Real Estate
View additional info

Welcome to your dream home in highly sought-after Clarks Rest, just minutes from all the charm and dining of Leonardtown Square. This vibrant community features sidewalks, a community pool, and that perfect neighborhood feel youve been looking for. Step inside to find real hardwood floors in the entryway and luxury vinyl plank flooring throughout the main living areas, including the spacious living room, dining room, and kitchen. The kitchen is a true highlight of the home, complete with granite countertops, stainless steel appliances, and a convenient eat-at bar, making it ideal for everyday living. Head to your backyard featuring a large stamped concrete patio, perfect for summer barbecues, cozy fire pits, or outdoor entertaining. Upstairs, the flexible floor plan offers 3 bedrooms with the potential for a 4th. The owners suite showcases a tray ceiling, dual walk-in closets, soaking tub, dual vanities, and a versatile sitting room (that other potential 4th bedroom) - ideal for a home office, additional closet space, or lounge area. Need more space? The fully finished basement includes another full bathroom, offering endless possibilities for a guest suite, media room, or home gym. Additional features include blinds on all windows and the lifestyle benefits of living in a community that feels like home from day one.

Beds:
4
Baths:
5 Full/1 Half
Sq.Ft.:
6,116
Status:
Active
MLS#:
MDSM2025074
Type:
Single Family, Single Family-Detached
Subdivision:
PAW PAW HOLLOW
Lot size:
1.8 Acres
Year built:
1997
Courtesy: CENTURY 21 New Millennium
View additional info

Stunning Brick Front Colonial in Paw Paw Hollow - 1.8 Acres of Private Luxury Welcome to this well maintained and beautifully designed brick front Colonial in the highly sought-after Paw Paw Hollow. This spacious 4-bedroom, 5.5-bathroom home offers over 5,000 square feet of living space on a generous 1.8-acre lot, providing the perfect blend of comfort, elegance, and privacy. Main Level Features Include: Inviting formal living and dining rooms, perfect for entertaining. Expansive two-story family room with plenty of natural light. Chef's kitchen with a center island, ample cabinetry, and modern appliances. Convenient main level bedroom and full bath for guests or in-laws. Upper Level Features: 3 large bedrooms with 3 full baths for ultimate comfort and privacy. A cozy den for reading or office space or use as upper level play room. Lower Level Features: Spacious finished basement with a rec room and additional family room, ideal for recreation and relaxation. Full bath for added convenience. Additional Features: Enjoy year-round fitness with your own indoor exercise pool. Attached garage and 3-car carport, offering plenty of parking and plus attached heated storage area with garage door.. Paved circular driveway ensures ease of access and adds curb appeal. Beautifully landscaped yard with a private outdoor patio, perfect for outdoor living and relaxation. Has inground sprinkler system and invisible fence to help keep your furry friends from wandering off. This home has been wonderfully maintained inside and out, offering the ideal combination of luxury and comfort in a private, serene setting. Don't miss out on this exceptional property. Schedule your private tour today!

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

Welcome to 40801 Kiskadee Lane - a truly exceptional residence nestled on over 3 private acres in the prestigious waterfront community of Avenmar. This grand colonial home is an entertainers dream, offering over 6,000 square feet of beautifully designed living space, and is specially offered with the last available building lot in the community - an additional 3.5+ acre parcel for $200,000, giving you over 6.5 acres of tranquil privacy and future investment potential. (Seller prefers to sell together) As you enter this elegant home, you are immediately welcomed by the soaring ceilings and abundant natural light of the two-story family room, creating an open and inviting atmosphere. The gourmet kitchen is a chefs delight, featuring rich cherry cabinetry, granite countertops, custom serving station and desk area, and newer stainless steel appliances - all designed for both everyday living and effortless entertaining. The formal dining room comfortably accommodates a table for 12 and includes space for a hutch and serving buffet, perfect for hosting holidays and gatherings. Adjacent, a formal living room leads seamlessly into a bright and airy sunroom, ideal for morning coffee or afternoon reading. A unique highlight of the main level is a bonus bedroom or office tucked beside a full bath - perfect for guests, multi-generational living, or working from home. Upstairs, retreat to your luxurious primary suite, a true sanctuary featuring a large private sitting room, two walk-in closets, and an expansive spa-inspired ensuite bath with dual vanities, soaking tub, and walk-in shower. Three additional bedrooms and a full bath complete the upper level. The fully finished lower level offers flexible space for entertaining, hobbies, or guest quarters, and includes a large storage area and separate workshop. Outside, the stunning landscaping and private wooded setting offer peaceful views and a sense of serenity, all while being just steps away from Avenmars unmatched amenities - water access, community pool, clubhouse, equestrian facilities, and more. Set back on a private lane, this property combines the best of luxury, privacy, and community living. Dont miss this rare opportunity to own a legacy home with additional land in one of Southern Marylands most coveted neighborhoods. *Whole house generator * Irrigation system *Easy Maintenance Trex Deck (2022)

Beds:
3
Baths:
1 Full
Sq.Ft.:
924
Status:
Active
MLS#:
MDSM2024652
Type:
Manufactured Home
Subdivision:
NONE AVAILABLE
Lot size:
1 Acres
Year built:
1999
Courtesy: Home Towne Real Estate
View additional info

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

Beds:
5
Baths:
6 Full/2 Half
Sq.Ft.:
12,113
Status:
Active
MLS#:
MDSM2023270
Type:
Single Family, Single Family-Detached
Subdivision:
PROSPECT HILL
Lot size:
17.87 Acres
Year built:
2012
Courtesy: Engel & Volkers Annapolis, (443) 292-6767
View additional info

Stunning. Welcome to a world of unparalleled luxury and breathtaking beauty. Nestled along the tranquil waters off of the Potomac River, this custom-built four level waterfront estate on almost 18 acres, is a testament to architectural brilliance and sophisticated design. As you approach the grand entrance, you are greeted by a circular driveway, detached 3-car garage, attached 2-car garage, lush landscaping and a sense of serenity. Step inside and you'll be captivated by the focal point of the home, a striking spiral staircase that ascends to the four levels, adding a touch of drama and splendor. A private elevator also awaits to effortlessly transport you through each level of this palatial residence. The expansive living space is adorned with floor-to-ceiling windows, offering panoramic views of the shimmering waters that stretch beyond the horizon. The soul of this home is undoubtedly the gourmet kitchen, a culinary masterpiece featuring top-of-the-line appliances, custom cabinetry, a massive center island and a breakfast room with a groin vault ceiling that doubles as a gathering place for friends and family. Enjoy seamless indoor-outdoor living with access to an expansive terrace with retractable screens, perfect for al fresco dining or simply soaking in the astounding landscape. The flawless design of the main level seamlessly connects the formal living, dining, main living, full bathroom, butlers pantry, study, half bathroom, additional office, laundry room, mudroom and kitchen areas, creating an atmosphere of effortless grandeur. One of the standout features of this estate is the luxurious study, a haven for those seeking a refined space for work or contemplation. The custom-built cabinetry, rich wood paneling, and expansive views create an atmosphere of insight and productivity. As you ascend the spiral staircase within it, you'll discover an additional upstairs library space and doors that connect to the primary suite that redefines luxury living. Wake up to wondrous views of the water, and unwind in the evenings in a recently renovated spa-like en-suite bathroom complete with a soaking tub and a walk-in steam shower that can reach 105 degrees. The primary suite also boasts a private terrace overlooking the pool, creating a serene sanctuary within your own home. The walk-in closet is a haven for the fashion connoisseur, providing two wings with ample space for two curated wardrobes. As you continue on the second level, discover additional well-appointed bedrooms, each with its own en-suite bathroom. The fourth level offers a luxurious guest suite with its own bathroom fully handicapped accessible, a wet bar and a rooftop terrace commanding awe-inspiring views of the surrounding waters, creating an unrivaled setting for sunset cocktails or stargazing. The lower level is a crowning jewel, featuring a generous and versatile space that unveils a recreation area, guest or au pair suite, and a vast amount of storage. The outdoor living space is a true oasis, featuring a sparkling saltwater pool that seems to merge seamlessly with the grounds and bay beyond. There is an inground timed sprinkler system providing a green and luscious lawn year round. The pier has been resurfaced and the mean low water is 8 feet, ensuring that priceless maritime adventures begin just steps from your doorstep. In the sought after Leonardtown school district, the property possesses a Silver Leed certification and can withstand a Category 3 hurricane with a reinforced roof. While you will feel miles away from it all, you will be enamored by the charm, history and convenience of the area. DC is 90 minutes away, St. Marys Airport is 20 minutes away and a five minute boat ride to the wharf and lovely downtown Leonardtown. The Breton Bay Country Club is just two miles away or visit nearby Solomons Island, the Patuxent Naval Air Station or enjoy a quick kayak ride to a nearby winery or a summer sea plane ride. Welcome home.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,948
Status:
Active
MLS#:
MDSM2024686
Type:
Single Family, Single Family-Detached
Subdivision:
AVENMAR
Lot size:
2 Acres
Year built:
2002
Courtesy: JPAR Real Estate Professionals
View additional info

Welcome to your new home in the lovely Avenmar Community! Upon entering your new home youre greeted by a stunningly adorned 2 story foyer. As you make your way around the lower level you will find a formal living and dining room with a timeless trim work design. Walking into the kitchen you have an open concept flowing seamlessly into your family room where you will find a gas fireplace to keep you and your family cozy all winter long. As you go out the back door to your beautiful stamped concrete patio that was made for entertaining and youll find a walkway to your outdoor fire pit and be able to take in the views of your wooded 2 acre lot. Heading back inside and moving upstairs youll find 4 large bedrooms. The primary suite is a true escape with a walk in closet that provides an abundance of room and en-suite bathroom featuring a separate toilet room and a large soaking tub perfect for relaxing after a long day! You can have peace at mind with a new roof installed in 2023, sump pump with battery back up (2022), washing machine (2024), dryer (2023). Other upgrades include NEW HVAC unit upstairs, main level LVP (2022) and the stamped concrete patio was done in 2023. Community amenities are abound, with access to a clubhouse, tennis and volleyball courts, an equestrian center, scenic walking paths, and a community pier on Breton Bay with a kayak launch. Immerse yourself in the convenience of living just moments from Breton Bay Golf Club and the lively Leonardtown square. Youll be able to find fine dining, pubs, charming shops and more that are all locally owned and operated, giving you a sense of true community! ***The sellers will be replacing the carpet upstair in the primary bedroom, hallway and the fourth bedroom. Buyer to choose the color they would like!

Beds:
5
Baths:
2 Full/1 Half
Sq.Ft.:
3,238
Status:
Active
MLS#:
MDSM2023778
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.5 Acres
Year built:
1942
Courtesy: CENTURY 21 New Millennium
View additional info

Built in 1942, this 5-bedroom, 2.5-bath home offers over 3,200 square feet of character-filled living space Original hardwood floors, arched openings, detailed trim work, and vintage glass door knobs are just a few of the timeless details that give this home its warmth and soul-while updates like a newer heating system, domestic hot water, roof, and refreshed bathrooms bring you everyday comfort. With natural light in all the right places highlighting the homes spacious layout and warm, welcoming feel. A deep front porch sets the tone for quiet mornings, while the fenced backyard and two-car garage-with workshop space-add function to match the charm. And with coffee shops, restaurants, and Leonardtown Wharf just blocks away, it offers a walkable lifestyle. Lovingly cared for by just two families since it was built, this home is ready for its third chapter.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
3,907
Status:
Active
MLS#:
MDSM2023560
Type:
Single Family, Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.2 Acres
Year built:
2011
Courtesy: Realty Navigator
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This home is a MUST SEE!!!! Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful updates throughout, this home is perfect for growing families, multi-generational living, or anyone seeking flexible, functional space. Step inside to find a warm, welcoming layout , a spacious eat-in kitchen, and a cozy family room ideal for relaxing or entertaining. One of the standout features is the highly desirable first-floor large primary suite with an en-suite bath and ample closet space. Upstairs, youll find three large additional bedrooms with ample closet space and a full bath. The fully finished basement is a true bonus, offering even more living space with a fifth bedroom, full bathroom, and a custom theatre room-perfect for movie nights, game days, or casual entertaining. Additional highlights include: 3.5 well-appointed bathrooms First-floor laundry Two-car garage with additional driveway parking Spacious backyard with room to relax, play, or entertain Located in a friendly, established neighborhood with top-rated schools, parks, and easy access to shopping, dining, and Pax River Naval Base Captain Walter Francis Duke Elementary School This home checks all the boxes-space, location, and versatile living options. Dont miss your opportunity to make it yours!

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
6,311
Status:
Active
MLS#:
MDSM2023552
Type:
Single Family, Single Family-Detached
Subdivision:
ESTATES AT SINGLETREE
Lot size:
0.34 Acres
Year built:
2005
Courtesy: CENTURY 21 New Millennium
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Welcome to this three-level home located in the Single Tree community, just a short walk from vibrant downtown. Boasting over 6,700 square feet of beautifully designed living space, this home offers 6 bedrooms, 4.5 bathrooms, and a thoughtfully crafted layout perfect for both everyday living and entertaining. The main level features gleaming hardwood floors, a soaring two-story family room filled with natural light and gas fireplace, a formal dining room, and two dedicated home offices. The heart of the home is the gourmet kitchen, complete with 42-inch white cabinetry, granite countertops, and stainless steel appliances-perfectly positioned off the family room for effortless flow. The spacious primary suite is also located on the main level and includes a luxurious en-suite bath. A mudroom with laundry hookups sits just off the garage for added convenience. Upstairs, youll find four generously sized bedrooms and two full bathrooms, including a Jack-and-Jill bath ideal for families. The fully finished lower level is a dream retreat with a home theater, large second primary suite, gym, a second laundry area, and a charming wine closet tucked beneath the stairs. Situated on a .34-acre lot in a quiet cul-de-sac, this exceptional property offers the perfect blend of privacy and accessibility-just moments from shops, restaurants, and local events downtown.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,834
Status:
Active
MLS#:
MDSM2023654
Type:
Single Family, Single Family-Detached
Subdivision:
HERRING CREEK ESTATES
Lot size:
0.84 Acres
Year built:
1970
Courtesy: CENTURY 21 New Millennium
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Are you dreaming of living on the water? This is your perfect opportunity! Well maintained rambler featuring waterfront, shared pier with boatlift, sunroom, 2-car attached garage, 1-car detached garage, 2-car carport. Gorgeous back yard, perfect for entertaining and spending those summer nights with friends and family. Get on your boat whenever the mood strikes you. This is the perfect home to just relax and enjoy life. Come and check it out!

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,046
Status:
Active
MLS#:
MDSM2023568
Type:
Single Family, Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.21 Acres
Year built:
2010
Courtesy: CENTURY 21 New Millennium
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Welcome to your new home -- this stunning Colonial with 5 bedrooms, 3 full bathrooms and 1 half bathroom, 3300+ square feet and a finished basement are move in ready! New carpet has been installed and the entire house has been painted and pressure washed. Brand new Hardie plank fiber cement siding in deep ocean blue was installed in 2019. As you enter the grand foyer, wood floors lead you through the main level which includes an office with glass doors, formal dining room, great room w/gas fireplace, and gourmet kitchen. The kitchen has granite counters, island with bar style seating, upgraded cabinets, gas cooktop, wall ovens, and built in microwave. This floor plan is perfect for entertaining and gatherings or hosting events. The breakfast nook has sliders leading out to the back deck and fully fenced back yard. Sit, relax and enjoy a beverage as you fire up your grill this Spring and Summer. The primary bedroom has plenty of space to create your own private retreat and a walk in closet. The primary bathroom has tile floors, soaking tub, deluxe shower and dual vanities. Three additional bedrooms, a full bathroom, and laundry room complete the top level of this home. And if that's not enough there is more....the finished basement with rec room, theatre room and additional storage will blow you away. Walk out access to the back yard from the basement. Two car garage with garage openers. Community amenities include a swimming pool, tennis/basketball courts, sidewalks and open space for activities. Close to schools, shopping, restaurants and area amenities. Enjoy downtown Leonardtown's town square, yearly activities and the scenic waterfront wharf. Schedule your online appointment today.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,992
Status:
Active
MLS#:
MDSM2023542
Type:
Single Family, Single Family-Detached
Subdivision:
HOLLY OAKS
Lot size:
0.6 Acres
Year built:
1975
Courtesy: EXP Realty, LLC
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*Pending Release..Buyer got cold feet* Come check out this charming, move-in ready rambler with room to grow that has been waiting for YOU! This beautifully updated 3-bedroom, 2-bath home sits on a spacious half-acre lot and features a walk-out basement, newer roof, windows, siding, gutters, and furnace. Inside, youll find brand new LVP flooring, recessed lighting in the kitchen, living room, and basement, and abundant natural light throughout. The updated kitchen boasts quartz countertops, a tiled backsplash, center island, and a gas range-perfect for home chefs. A front-load washer and dryer are also included. Ceiling fans offer added comfort, and a U-shaped/circle driveway provides plenty of parking. With no HOA, there's flexibility to add a detached garage, pool, or screened porch-bring YOUR vision! ***VA assumable loan at a 4.75% interest rate available for qualified buyers! Additionally, this home is located in a USDA-eligible area, offering potential for 100% financing.*** Only 30 minutes from PAX River Naval Base and Solomons Island, where you can enjoy boating, jet skiing, and waterfront dining at favorites like The Island Hideaway, Clarkes Landing, and The Pier. Outdoor lovers will also appreciate nearby St. Marys River State Park. Enjoy peaceful country living with modern updates and exciting possibilities-schedule your showing today!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,858
Status:
Active
MLS#:
MDSM2022494
Type:
Single Family, Single Family-Detached
Subdivision:
CLARK'S REST PHASE 1
Lot size:
0.27 Acres
Year built:
2016
Courtesy: CENTURY 21 New Millennium
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This gorgeous Pinehurst model in Clark's Rest community is not going to last long! This home has 4BR/3.5BA located on large corner home site, Open floor plan, with upgraded Kitchen appliances and gas cook-top and granite counter tops. Hardwood flooring throughout , upgraded lighting with recessed lighting in the kitchen, large walk-in Pantry, freshly painted walls, separate formal dining room, with crown molding. There is a additional room off of the family room that could be used for a office or den .Owner's Suite has large walk in closets, soaking tub, upgraded tile and double vanities. All of the bedroom's are very spacious. The basement has finished rec room and full bath, a large work out room, with additional other rooms for storage, there is a 2 car garage with openers, Magnificent sunsets from your front porch , Community offers an outdoor pool, side walks, walking trails, playground, short walk to Leonardtown for fun shopping and dining.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,738
Status:
Active
MLS#:
MDSM2022692
Type:
Single Family, Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.22 Acres
Year built:
2008
Courtesy: CENTURY 21 New Millennium
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**SIGNIFICANT PRICE REDUCTION!** Now offered at more than $16,000 below the original list price, 23534 Belmar Drive presents a rare opportunity to own a luxurious, move-in-ready home in the prestigious Leonards Grant community of Leonardtown, MD. With over 5,000 square feet of refined living space, this exceptional residence combines elegant design, modern upgrades, and unmatched comfort in one of St. Marys Countys most desirable neighborhoods. Inside, youll find an expansive open-concept layout flooded with natural light and enhanced by high-end finishes throughout. The home features five spacious bedrooms and 3.5 beautifully appointed baths, offering plenty of room for both everyday living and entertaining. Recent premium upgrades include brand-new HVAC systems (2023 and 2024), a 2024 tankless water heater, and a sump pump with battery backup for added protection. Low-cost solar panels provide energy efficiency and monthly savings, with excess power returned to the grid. The fully finished basement is an entertainers dream, complete with a built-in surround sound system-ideal for movie nights, game days, or immersive audio experiences. Step outside to the screened-in back porch, a peaceful space to enjoy your morning coffee or evening breeze. Residents of Leonards Grant enjoy access to exceptional community amenities, including a resort-style pool, clubhouse, tennis and basketball courts, walking trails, and multiple playgrounds-all within minutes of shopping, dining, and charming downtown Leonardtown. Commuters will appreciate the short drive to NAS Patuxent River, less than 20 minutes away. This thoughtfully maintained home now comes at a new, more attractive price & the owners will consider a flooring contribution with a great offer! Dont miss your chance to make 23534 Belmar Drive your own-schedule your private showing today!

Beds:
5
Baths:
4 Full
Sq.Ft.:
3,540
Status:
Active
MLS#:
MDSM2022602
Type:
Single Family, Single Family-Detached
Subdivision:
CLARK'S REST PHASE 1
Lot size:
0.15 Acres
Year built:
2022
Courtesy: Fairfax Realty Premier
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VA Assumable loan at 5.25% interest rate. Seller is also offering $10,000 in closing help! Welcome to 23348 Lindsay Drive - where space, style, and comfort come together in the heart of Leonardtowns sought-after Clarks Rest community. This nearly new 5-bedroom, 4-bath home offers over 3,500 sq ft of beautifully designed living space with thoughtful upgrades and a flexible floor plan perfect for modern living. Step inside to a sun-drenched open layout featuring luxury vinyl plank flooring, a spacious family room, and a gourmet kitchen with granite countertops, a large center island, and a walk-in pantry. A first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs, find four generously sized bedrooms - each with a walk-in closet - and a serene primary suite with dual vanities and a tiled shower. The partially finished basement offers even more room to grow with space for a rec room, home gym, or office. Enjoy community amenities including a pool, clubhouse, playgrounds, tennis courts, and walking trails - all just minutes from downtown Leonardtown, shopping, restaurants, and top-rated schools. Freshly priced to sell - this is your opportunity to own a move-in-ready home in one of Leonardtowns most desirable neighborhoods.

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