55 properties for sale in Chaptico, District 4 Chaptico St Mary's County Maryland

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Opportunity meets lifestyle in this charming water-view rambler overlooking the Wicomico River, located in the desirable Mill Point Shores community. Positioned just across the street from waterfront homes, this property offers the feel of waterfront living without the premium pricean ideal opportunity for buyers looking to invest, create a weekend retreat, or customize a home to their vision. This home is being sold strictly AS IS and is priced to reflect the need for updating, making it especially appealing for buyers looking to build sweat equity and add personal touches over time. The layout is simple and functional, featuring an eat-in kitchen with electric stove and refrigerator that flows directly into a spacious sunken family room additionan inviting space perfect for relaxing, entertaining, or unwinding after a day on the water. 3 bedrooms and 1 full hall bath provide comfortable everyday living. Set on a generous lot, the outdoor space adds versatility and appeal. A detached

Welcome to 36061 Roosevelt Boulevard, a solid brick raised rambler nestled in the established Mill Point Shores community of Chaptico, Maryland. This three-bedroom, two-full-bath home offers 1,780 square feet of above-grade living space and sits on a quarter-acre lot, providing a peaceful setting with room to personalize and add value. Built in 1945, the home features classic brick construction, a functional one-level layout, and a spacious interior footprint that is increasingly hard to find at this price point. The living area is anchored by a brick fireplace, creating a warm focal point, while the home’s generous room sizes allow for flexible use—whether as a primary residence, second home, or investment opportunity. Central air conditioning and electric heating are already in place, and the property is serviced by a private well and septic system. The exterior includes a deck overlooking the yard, offering outdoor living potential for entertaining or quiet relaxation. The lot provi

Just reduced! This home is located in the tucked-away community of Longview Beach at 36797 Ricardo Drive, Bushwood, Maryland, and is currently priced at $340,000.00. Sitting on 10,500 sf. Is just under 1u002F4 acre. This recently updated home with great features for winter is the perfect location for the summer. A new metal roof with lighting rods was installed in 2019, including upgrading installation in the atticu002Fceiling and exterior walls. Home features a renovated eat-in kitchen with custom cabinets, a large kitchen counter area for breakfast, and new lighting that opens into the family room. The kitchen has access to the rear yard, and a covered carport or front porch area completes the living space. This gem is awaiting a new owner to enjoy all the benefits of just a short a quiet haven for all nature lovers to sip your morning coffee and watch the wildlife that passes by. In the early morning, you can take a walk down less than half a mile to the shoreline for some early mor

Welcome to the Longview Beach community! This single-level ranch home sits on approximately 0.23 acres and offers a great opportunity for buyers looking to renovate and make it their own. Enjoy access to the Potomac River with nearby community amenities including beach, pier, and boat ramp. Property being sold as is

Back on the market and now financing available! Imagine waking up each day to breathtaking sunrises over Saint Clements Bay! This delightful cottage offers a tranquil, vacation-like lifestyle with no HOA and prime waterfront access. It also presents income potential as it can sleep six. Meticulous planning has crafted this stunning home, which exudes the elegance of a high-end interior designer. Inside, you'll find a bright and airy living area that effortlessly merges indoor and outdoor spaces, showcasing captivating water views. The cottage boasts 12-foot ceilings, unique metal roof with cupola and weathervane, an upgraded well pressure tank, robust 200-amp service, full-sized washer and dryer, and a beautifully tiled bathroom with walk-in shower. Designer-inspired kitchen is adorned with quartz countertops, Verona gas range, stainless steel appliances, and a stunning tiled backsplash that frames amazing river views. The loft offers a 5-foot clearance at the center, a closet, and add

New Construction in Chaptico! Adorable Cape Cod situation on over one acre, surrounded by mature trees, creek, gorgeous pastoral views and beautiful Chaptico Sunsets! This Cape Cod welcomes you home from your hectic day to a serene surrounding with a convenient location to all amenities. You are only minutes away from Leonardtown shopping /entertainment and Pax River /Dalgren. The main level boasts a large open kitchen, dining area, and huge open den. The main level also offers an office that could be utilized as a 4th bedroom. Upstairs there are 3 large bedrooms, 2 full baths, and a sitting/flex area with stunning views! Luxury vinyl plank flooring flows through every room in this bright home. The back deck is off the heart of the home, kitchen, and is tucked in between mature woods with creek. The front porch is the place to be for'cocktail hour' to catch stunning Chaptico sunsets! This is a must see, one of kind home located in the best hidden gem of St. Mary's County; a rare opport

Welcome to this exceptional Compton Model by Quality Built Homes, ideally situated in the sought-after Grandview Haven community of Mechanicsville, Maryland. Located on a beautiful 1-acre lot backing to mature trees, this impressive property offers the perfect combination of privacy, comfort, and community amenities including a tennis court and playground. Boasting 4 bedrooms, 3.5 bathrooms, and a spacious side-load 2-car garage, this thoughtfully upgraded home is designed for both everyday living and effortless entertaining. The inviting open-concept floor plan features a gourmet kitchen complete with deluxe maple cabinetry, granite countertops, double wall ovens, gas cooktop, and abundant prep and storage space. The kitchen flows seamlessly into the expansive living area filled with natural light and views of the private backyard setting. Outdoor living is just as impressive with a large 16x16 wood deck overlooking the beautifully landscaped and fully fenced backyard. Perfect for gat

Custom Home with In-Law Suite, Private Backyard, and Dual Garages in Grandview Haven! This beautifully maintained home offers the perfect combination of comfortable everyday living, entertaining space, and flexibility for multi-generational living. With 4 bedrooms, 4.5 bathrooms, and thoughtfully designed living areas, there's room for everyone to spread out and enjoy. At the heart of the home is a two-story family room, flooded with natural light from oversized windows surrounding a gas fireplace. The spacious Eat-In Kitchen features upgraded cabinetry, granite countertops, a center island, range, 2nd wall oven, built-in microwave, and ample workspace for preparing meals. There is a separate room off of the kitchen which can easily serve as a formal dining room, sitting room, home office, or flex space. The Main-Level Primary Suite offers a peaceful retreat with a tray ceiling, dual walk-in closets, and a luxurious en-suite bath featuring dual vanities, a soaking tub, and a separate f

Stunning Custom Home with Spacious Living, Energy Savings & Room to Grow Welcome to this beautifully maintained 3,800-square-foot home in the desirable Grand View Haven community. Thoughtfully designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces, quality finishes, and exceptional value. The bright, open floor plan features spacious gathering areas, a kitchen with double ovens, granite countertops, abundant cabinetry and workspace, and large windows that fill the home with natural light. Whether hosting family and friends or enjoying a quiet evening at home, this layout offers the perfect balance of openness and comfort. One of the homes standout upgrades is the beautiful hardwood flooring throughout the entire 4-bedroom upper level, adding warmth, elegance, and lasting value while providing a carpet-free living space thats both stylish and easy to maintain. This is a definite plus for allergy sufferers. The finished lower level p

Welcome to this truly one-of-a-kind Mechanicsville property offering an incredible combination of space, style, and functionality! Situated on a beautiful 1.6-acre lot, this impressive home features 8 bedrooms and has been thoughtfully updated to create the perfect blend of modern luxury and comfortable living. The heart of the home is the stunning, fully renovation, highlighted by an expansive open-concept design that's perfect for entertaining. The gourmet kitchen is a showstopper, featuring a massive center island, custom cabinetry, stylish finishes, abundant counter space, huge walk in pantry and an effortless flow into the living and dining areas. Whether you're hosting holiday gatherings or everyday family meals, this space was designed to bring people together. The spacious primary suite offers a private retreat with a luxurious spa-inspired bathroom, complete with a freestanding soaking tub, oversized custom tile shower, elegant finishes, and a large walk-in closet. Throughout

Well if you blinked you did miss it BUT now you have a chance to get it again because buyers financing did not happen. Don't blink because this beauty will be swept up quickly. Property is in excellent condition and is ready for its new owner. House is kept in immaculate condition. No painting, flooring, etc. Needed. Just move right in. Less than half mile to Wicomico River

Just reduced! This home is located in the tucked-away community of Longview Beach at 36797 Ricardo Drive, Bushwood, Maryland, and is currently priced at $340,000.00. Sitting on 10,500 sf. Is just under 1/4 acre. This recently updated home with great features for winter is the perfect location for the summer. A new metal roof with lighting rods was installed in 2019, including upgrading installation in the attic/ceiling and exterior walls. Home features a renovated eat-in kitchen with custom cabinets, a large kitchen counter area for breakfast, and new lighting that opens into the family room. The kitchen has access to the rear yard, and a covered carport or front porch area completes the living space. This gem is awaiting a new owner to enjoy all the benefits of just a short a quiet haven for all nature lovers to sip your morning coffee and watch the wildlife that passes by. In the early morning, you can take a walk down less than half a mile to the shoreline for some early morning fis

Opportunity meets lifestyle in this charming water-view rambler overlooking the Wicomico River, located in the desirable Mill Point Shores community. Positioned just across the street from waterfront homes, this property offers the feel of waterfront living without the premium price—an ideal opportunity for buyers looking to invest, create a weekend retreat, or customize a home to their vision. This home is being sold strictly AS IS and is priced to reflect the need for updating, making it especially appealing for buyers looking to build sweat equity and add personal touches over time. The layout is simple and functional, featuring an eat-in kitchen with electric stove and refrigerator that flows directly into a spacious sunken family room addition—an inviting space perfect for relaxing, entertaining, or unwinding after a day on the water. 3 bedrooms and 1 full hall bath provide comfortable everyday living. Set on a generous lot, the outdoor space adds versatility and appeal. A detache

Hunters Paradise-Nestled in the prestigious Shamrock Glenn Estates, this exquisite ranch-style residence offers a harmonious blend of luxury and comfort, set on a sprawling 7.18-acre lot that backs to serene trees and lush greenery. The property, built in 1998 and undergoing significant renovations in 2026, showcases a meticulous attention to detail and high-end finishes throughout. As you step inside, you are greeted by an inviting open floor plan that seamlessly connects the living spaces, perfect for both entertaining and everyday living. The interior features include elegant built-ins and a cozy fireplace adorned with glass doors and a classic mantel, creating a warm focal point in the living area. The country-style kitchen is a chef's dream, equipped with modern appliances including a self-cleaning oven, electric range, and a spacious refrigerator, all designed to elevate your culinary experiences. The dining area is perfectly positioned to enjoy views of the garden and trees, enh

This well-maintained 3-bedroom, 2-bath rambler features a comfortable one-level layout, including a primary bedroom with a private full bathroom. The kitchen offers quartz countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Major updates include an HVAC system installed in 2018, a roof replaced in 2020, and appliances updated in 2018. Additional highlights include an attached two-car garage with automatic opener and a dehumidifier in the crawlspace. Outside, enjoy a fully fenced backyard with plenty of room and two storage sheds

Your dream home, your way – to be built on 1 acre, please note the tax record is wrong. Why spend your weekends touring older homes that need 'just a little work' when you can build exactly what you want? Avoid the bidding wars and move into a masterpiece designed specifically for you. This 4-bedroom, 2.5-bathroom 'Ariana' floor plan by Litz Custom Homes is the perfect blend of luxury and functionality on a beautiful Mechanicsville lot. The Custom Experience: Unlike most builders, we don't limit you to a few 'packages. ' Bring your Pinterest boards! From the tile and flooring to the hardware and light fixtures, you are the designer. Want to move a wall, vault the ceilings, or add a sunroom? This is a full-service custom build where your ideas actually matter. Home Highlights: Stunning Curb Appeal: A stone facade and a charming wrap-around front porch made for rocking chairs and relaxation. Gourmet Heart of the Home: An open-concept kitchen featuring 42-inch cabinets, a center island wi

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Price improved! Shop and residence on 18+ acres. All brick rambler on 18.64 acres of wooded, private land offering exceptional craftsmanship and versatility. Geothermal heat pumps and Andersen windows, extensive power supply specs are just a couple of the steps taken by the owner to make this a long-lasting home. Three-bay garage and shop space in the lower level of the home AND a large shop building, separately located on the acreage for home privacy. The 4-bedroom, 4.5-bath brick residence features a massive central great room with vaulted ceilings and a striking masonry fireplace with custom wood elevator. The adjacent gourmet kitchen is designed for both function and style, featuring stainless steel appliances, custom backsplash, and a huge center island. The large main level owner's suite is large in scale with huge closet and bath. Owner's shower has body sprays, corner tub is jetted! This suite also enjoys access to the rear patio. Two more large bedrooms share a second full bat

Multiple offers received! Please submit highest and best offer by 8pm on 7/8! Welcome home to this beautifully updated 4-bedroom, 2-bathroom home, perfectly situated on a 1.14 acre lot in the heart of Mechanicsville. Thoughtfully upgraded throughout, this home features a stunning kitchen with quartz countertops, stylish two-tone cabinetry, a farmhouse sink, newer appliances, and a spacious center island thats perfect for entertaining or everyday living. The oversized primary suite offers a peaceful retreat with its own private deck. The luxurious en-suite bathroom showcases beautiful tile work, a double vanity, and a custom walk-in shower with a glass door. Step outside to enjoy the large backyard that backs to trees, offering both privacy and tranquility. Two oversized sheds provide plenty of room for storage, hobbies, or a workshop. Conveniently located close to shopping, dining, schools, and commuter routes, this move-in-ready home combines modern updates with the space and privacy

This beautiful home is an entertainer's dream in the desirable Ben Oaks neighborhood. With 2 acres outside and 5000 square feet of finished space inside, there is plenty of room for everyone! Enjoy peaceful mornings rocking on your front porch and relaxing evenings on the amazing screened in back porch. Main level features a fabulous gourmet eat-in kitchen, dining room, a bright and sunny sitting room, generously sized family room, a mudroom, and a guest bathroom. When you're ready to relax, head on upstairs to the large primary suite with two walk-in closets, additional sitting room, and spacious bathroom. Three additional bedrooms, a shared full bathroom, and a laundry room have all the space you need upstairs. Finished basement has a large living area, a fifth bedroom, full bathroom and a bonus room that is perfect for a gym or office space. Looking for extra garage space? This home has not just one but (2) two-car garages! One is perfect for entertaining, and the other for all of y

See Interactive 3D Tour! Solar panels are owned. Electric bills for April $15.16, May $15.64, & June $15.64 Discover this spacious 4-bedroom, 3-bath home in the desirable Wicomico Shores waterfront community in St. Marys County. Offering the perfect blend of comfort, efficiency, and recreation, this property is ideal for those who love boating, golfing, and outdoor entertaining. The home features fully owned solar panels (not leased) that deliver exceptional energy efficiency and remarkably low electric bills. Additional comfort comes from a pellet stove in the family room and a whole-house fan system that efficiently distributes heat throughout the home, including the basement. An oversized garage provides ample space for vehicles, storage, or a workshop. Step outside to your private above-ground pool with deck the perfect setup for summer gatherings, relaxation, and creating lasting memories with family and friends. Wicomico Shores offers a true waterfront lifestyle with easy access

A grand double-door entrance welcomes you into the foyer then head up to main level featuring hardwood floors, a spacious living room, a formal dining room perfect for gatherings, and kitchen with ample cabinet space, and room to expand. The main level also includes primary suite with a private bath alongside two additional bedrooms and a hall bath. The expansive lower level features a recreation room anchored by a cozy wood-burning insert fireplace, a huge fourth bedroom, a third full bath, dedicated laundry, storage, and an ideal workspace. Entertain effortlessly on the massive deck spanning the entire width of the home, or relax below on the full-width covered patio providing perfect shade. Additional Amenities: Attached two-car garage plus plenty of driveway parking. Detached outbuilding equipped with electricity, perfect for a workshop or extra storage. Exceptional storage solutions with two separate attics. All of this and more at a prime location situated on a lush lot directly

Offer deadline. WEDNESDAY 7/1/2026 12:00PM Come join us this Sunday, June 28th, from 10 AM to 12 PM for an open house at this beautiful, turnkey Cape Cod in the highly desirable Wicomico Shores community! This well-maintained home offers comfortable living with thoughtful updates throughout. Upstairs youll find three bedrooms and a full bath, plus the convenient laundry area. The main level features a bright, spacious open-concept layout with a stunning built-in shiplap accent wall, electric fireplace, and mantel shelf perfect for displaying your favorite decor. The updated kitchen boasts stainless steel appliances, a large pantry, and a generous island with storage and stools that convey with the home. Additional highlights include: Premium Sonos surround sound system in the living room and primary bedroom, Private primary bedroom on the main level with an ensuite full bath featuring double sinks and a spacious vanity, convenient half bath on the main level, walk-out access from the d

Located in the desirable Wicomico Shores community, residents enjoy access to the public golf course, beach, and water access, making it easy to embrace the Southern Maryland lifestyle. This charming 3 bedroom, 2 bath home is tucked away at the end of a quiet cul-de-sac. Inside, you'll find luxury vinyl plank flooring throughout, a cozy wood-burning fireplace, and a functional layout ready for its next owners. Recent updates include a new roof. Relax on the covered front porch or entertain in the open backyard featuring a spacious deck. The attached garage offers excellent storage and flexible space for a workshop, home gym, motorcycle parking, or lawn equipment