Port Tobacco Real Estate

Port Tobacco Real Estate

Welcome to Port Tobacco, Maryland—a hidden gem nestled in the heart of Charles County. This quaint town is steeped in rich history and offers a unique blend of serene rural charm and vibrant community spirit. Established in the 17th century, Port Tobacco was once a bustling port and the county seat, and remnants of its storied past can still be felt in the charming architecture and picturesque landscapes that adorn the area.

One of the standout features of Port Tobacco is its close-knit community, where neighbors become friends and local events create lasting memories. The town hosts various seasonal festivities, from farmers' markets to holiday celebrations, ensuring there’s always something happening to bring residents together. Nature enthusiasts will appreciate the lush greenery and scenic views that make up the surrounding countryside, perfect for hiking, biking, or simply enjoying a peaceful afternoon outdoors.

Port Tobacco is also conveniently located, providing easy access to nearby metropolitan areas while maintaining its tranquil atmosphere. This makes it an ideal spot for those seeking a quiet retreat without sacrificing the conveniences of modern living. Explore local shops, dine at cozy eateries, and immerse yourself in the vibrant culture that makes Port Tobacco a delightful place to call home.

Whether you're considering a move or simply looking for a weekend escape, Port Tobacco promises an enchanting experience filled with history, community, and natural beauty. Discover the charm of this remarkable town and see why so many are drawn to its welcoming embrace.

Newest Listings in Port Tobacco

$650,000
4 Beds ⋅ 4 Baths ⋅ MDCH2059304 MLS
Escape to your own private sanctuary on nearly 6 wooded acres with NO HOA — complete with ATV and hiking trails, a spring-fed stream, and abundant wildlife right outside your door. This secluded lifestyle property offers the best of both worlds: peaceful, private country living just a convenient drive to Washington, DC and multiple military installations, making it an ideal location. Truly an immaculate home, offered for sale for the first time by the original owners, it showcases true pride of ownership throughout. Step through the foyer entryway into a traditional floor plan built for easy main-level living. The enormous eat-in kitchen is a chef's dream, featuring a large island and abundant additional storage — plenty of room to cook, gather, and entertain. The formal dining room, living room, and cozy den/fourth bedroom offer flexible spaces for everyday living. The spacious primary suite offers a private retreat, complemented by two additional bedrooms and a second full bath, all conveniently located on the main level along with the laundry room with half bath and entry to the garage. The lower level expands your living options with a rec room featuring a pellet stove, a kitchenette offering potential multi generational living or potential rental income, a private den, a third full bath, a multipurpose room and abundant storage throughout. Outdoor living shines here with three distinct spaces to enjoy the property: a deck off the dining room overlooking your gorgeous wooded lot, an enormous covered patio off the lower-level rec room, and an additional patio tucked behind the garage. An oversized garage plus storage shed ensure there's room for all your vehicles, tools, toys, and outdoor gear. Peaceful, private, and move-in ready — with acreage to roam, trails to explore, and nature at your doorstep — this is secluded living without sacrificing convenience to the DC metro and regional military bases, plus shopping and restaurants close by.

7710 Walking Deer Pl, Port Tobacco
$412,500
3 Beds ⋅ 2 Baths ⋅ MDCH2058894 MLS
This distinctive 3-bedroom, 2-bath home delivers more than 2,000 square feet of living space on a full acre in Port Tobacco! A massive front porch welcomes you inside, where the dramatic great room immediately impresses with soaring two-story vaulted ceilings, a striking floor-to-ceiling brick fireplace with pellet stove, and plenty of room for gathering and entertaining. A separate sitting area and formal dining room provide additional flexibility, while the open kitchen features upgraded granite countertops and overlooks the main living space. The sunroom offers a bright place to relax and opens directly onto the expansive rear deck and large backyard—an inviting setting for cookouts, entertaining, gardening, or simply enjoying nature. Two generously sized bedrooms are conveniently located on the main level, along with a beautifully remodeled full bathroom featuring a dual-sink vanity and tiled shower. Upstairs, the private primary suite includes its own renovated bathroom with an impressive spa-inspired walk-in shower designed to make every day feel luxurious. An additional room offers the perfect space for a home office, creative studio, exercise room, or hobby area. Additional highlights include a dedicated laundry room, a large crawl space with potential for storage or workshop use, and an oversized driveway offering abundant parking. With its dramatic architecture, flexible layout, thoughtful updates, and expansive one-acre setting, 7595 Simms Landing Road is ready to welcome you home!

7595 Simms Landing Rd, Port Tobacco
$645,900
4 Beds ⋅ 3 Baths ⋅ MDCH2058682 MLS
Motivated seller - bring all offers!!! Beautifully maintained and situated on 2.9 acres in Historic Port Tobacco, this spacious home offers nearly 3,700 finished square feet, a versatile floor plan, and thoughtfully designed accessibility features. The main and upper levels provide approximately 3,338 square feet, with an additional 350 square feet of finished living space in the walkout lower level. The main level features hardwood flooring in the foyer, crown molding, a den that could easily serve as an additional bedroom or private home office, and an updated full bath designed for accessibility. A wheelchair lift in the two-car garage provides convenient access into the home. Upstairs you'll find four generously sized bedrooms, including a spacious primary suite with three closets and an updated private bath. Two additional bedrooms feature walk-in closets, providing plenty of storage. In addition, the crawl has been updated with new insulation and vapor barrier. Enjoy the peaceful 2.9-acre setting from the deck, while the finished walkout lower level provides additional space for relaxing, entertaining, hobbies, or recreation. New carpet installed in basement. Two heat pumps provide efficient heating and cooling. Located in Historic Port Tobacco, this home offers a peaceful setting while still providing convenient commuter access to Indian Head Naval Support Facility, Joint Base Andrews, Washington, D.C., and surrounding employment centers. Exceptionally well maintained and move-in ready, this home offers a wonderful combination of space, acreage, accessibility features, abundant storage, and a flexible floor plan.

7740 Chapel Point Rd, Port Tobacco
$625,000
4 Beds ⋅ 3 Baths ⋅ MDCH2058738 MLS
ESTATE LIVING… QUIET COMMUNITY… WATER VIEWS BY THE COMMUNITY GAZEBO… FRESH AIR TO BREATHE. Welcome to 7975 Deepwater View Drive, where spacious estate-style living meets peaceful natural surroundings in the beautiful Port Tobacco area. Set within a distinctive community where homes are situated on approximately one-acre or larger homesites, this property offers the space, privacy, and tranquility that are increasingly hard to find. Just beyond your front door, residents can enjoy the community gazebo while taking in views of the Port Tobacco River—a peaceful setting to relax, gather with family and friends, or simply enjoy the beauty of nature. Take a walk along the community trail and enjoy views of the water along the way. This charming brick-front Colonial is situated on a beautifully maintained, spacious homesite surrounded by mature trees and generous open green space. A long driveway leads to the attached 2-car garage, while the expansive lawn offers plenty of room for entertaining, recreation, gardening, or simply enjoying your own private outdoor space. Inside, the home features 4 bedrooms and 2.5 bathrooms with a traditional Colonial floor plan and comfortable living spaces throughout. The unfinished basement offers tremendous potential for future expansion—imagine a recreation room, home theater, gym, home office, additional living area, or all the storage space you have been looking for. The lifestyle here offers a wonderful balance—the privacy and space of estate-style living combined with the warmth of a welcoming community. Whether relaxing on your own spacious grounds, walking the community trail, or sitting at the gazebo overlooking the Port Tobacco River, there are plenty of opportunities to slow down and enjoy your surroundings. Port Tobacco Marina is just a short drive away, adding nearby waterfront scenery and dining opportunities. With its acre-plus community setting, classic brick-front design, spacious yard, 2-car garage, unfinished basement with expansion potential, and beautiful natural surroundings, 7975 Deepwater View Drive offers something increasingly difficult to find—room to breathe while remaining connected to the DMV. You may just pinch yourself and wonder, “Am I really still in the DMV?”

7975 Deepwater View Dr, Port Tobacco
$400,000
3 Beds ⋅ 2 Baths ⋅ MDCH2058666 MLS
This peaceful retreat offers an exceptional opportunity to own 2.25 lush, beautifully maintained acres surrounded by expansive properties and natural beauty. Mature landscaping creates a private, park-like setting, with towering holly trees, a graceful Japanese maple, and a stately magnolia bringing new character to the landscape with every season. A distinctive teardrop-shaped driveway leads to the welcoming entrance and sets the tone for a home filled with possibility. Inside, inviting spaces are ready for a buyer’s personal vision and thoughtful updates, offering the opportunity to transform the property into a home that reflects their own style. Step outside to a fully fenced backyard designed for privacy, pets, outdoor enjoyment, and peaceful moments surrounded by nature. Two storage sheds provide valuable space for tools, equipment, and hobbies, while the Japanese maple creates a striking focal point with brilliant seasonal color. Whether gathering by the fireplace in the cozy front room or unwinding in the garden, this property offers a wonderful balance of comfort and tranquility. Additional highlights include a brand-new heating, ventilation, and air conditioning system, propane service, and a two-car garage. Conveniently located near La Plata’s seasonal events, shopping, everyday conveniences, and the College of Southern Maryland, this property pairs a serene setting with easy access to local amenities. With beautiful acreage, mature landscaping, valuable updates, and exciting potential, this is an opportunity to create something truly special. ** Photos have been virtually staged"

8965 Poorhouse Rd, Port Tobacco
$535,000
4 Beds ⋅ 3 Baths ⋅ MDCH2057286 MLS
Experience Southern Maryland waterfront living at its finest. This uniquely inviting, superbly maintained home sits on .84 private acreage bordering on 200 feet of navigable Port Tobacco River frontage. Owned throughout its history by one family, this well cared for and stately, all-brick, 2,442 square foot Home features 4 bedrooms, 2.5 fully renovated bathrooms, formal dining room, separate living room and sun-filled family room w/ fireplace located just off the modern kitchen w/ granite counters, high-end cabinetry and breakfast-for-two seating with your own exclusive view of the river. Additional features include hardwood floors throughout the majority of the home with ceramic tile and newly installed LVP making up the rest. The primary bedroom boasts a spacious walk-in closet and direct access to private deck overlooking the backyard and its festive 16’ octagonal gazebo, fire pit, mature trees, Of particular significance is the Home’s ultra efficient, energy-independent profile. Thanks to the 15.91 kW Solar System (OWNED) and integrated energy-saving features, including but not limited to a high efficiency HVAC system and tankless/on-demand water heater (both electric), the cost for electricity is consistently ZERO DOLLARS (potentially income producing). Furthermore, the home has been upgraded to a 350-amp electrical service, perfect for EV charging, a hot tub, fully-equipped work shop and more. Additional items of interest include two 14-ft tandem kayaks with built-in storage racks, front porch chair swings,, active chicken coop , private parking for 10+ vehicles, full-sized freezer, 12' x 28' workshop/storage building, separate 4' x 8' shed, rain water collection barrels, shaded riverside pergola and so much more. Well-priced and move-in ready. Hope to see you soon.

7349 Mary Dr, Port Tobacco
$749,999
5 Beds ⋅ 6 Baths ⋅ MDCH2056602 MLS
7980 Norwich Court, Port Tobacco, MD Nestled on 3.8 private wooded acres in the sought-after Port Tobacco area, this exceptional custom residence offers over 5,200 finished square feet, 5 bedrooms, 5 full bathrooms, and 1 half bath, blending timeless architecture, multigenerational flexibility, and luxury living in a serene natural setting. From the moment you arrive, the expansive homesite, mature trees, and stately brick front elevation create an impressive first impression. Inside, a dramatic dual-access waterfall staircase anchors the grand foyer and connects seamlessly to both the formal living spaces and the heart of the home. Rich hardwood flooring, crown molding, chair rail detailing, soaring ceilings, and oversized windows create a warm yet elegant atmosphere throughout. Designed for both everyday living and entertaining, the main level features a spacious living room, formal dining room, private home office, and a stunning great room with wooded views, highlighted by a floor-to-ceiling stone gas fireplace and abundant natural light. The adjoining morning room offers skylights, panoramic views of the surrounding landscape, and a secondary sink and prep area perfect for hosting gatherings and holiday celebrations. A rare and highly desirable feature, the main-level primary suite provides convenience and privacy with an en suite bath and walk-in closet, making this home ideal for multigenerational living, aging-in-place, or accommodating long-term guests. Upstairs, discover a spectacular owner's retreat designed as a private sanctuary. This luxurious primary suite features a tray ceiling, ceiling fan, hardwood flooring, and a cozy gas fireplace with custom TV inset. Double doors lead to the spa-inspired en suite bathroom complete with an oversized walk-in shower, relaxing soaking tub, separate dual vanities, private water closet, and tranquil wooded views. The suite also boasts an impressive 10+ foot walk-in closet and a private sitting room featuring built-in shelving, sink, beverage cooler, and flexible space ideal for a dressing lounge, reading room, wellness retreat, or executive workspace. The upper level also includes a spacious secondary suite perfect for a prince or princess retreat, complete with its own en suite bathroom, step-in closet, and peaceful wooded views, providing privacy and comfort for family members or guests. Bedrooms three and four are thoughtfully designed with a shared Jack-and-Jill bathroom, creating an ideal layout for siblings or overnight guests. Hardwood flooring extends throughout the upper-level hallway, which also features a double-door linen closet and an additional oversized storage closet that offers excellent space for seasonal décor, luggage, household storage, or the potential conversion to an upper-level laundry area. Combining luxury, functionality, and flexibility, the upper level offers accommodations for a variety of lifestyles, including multigenerational living, extended guest stays, work-from-home needs, and growing households. The finished lower level provides additional living and entertaining space, offering flexibility for recreation, media, fitness, hobbies, or extended-stay guests. Outside, the nearly four-acre homesite offers endless opportunities for outdoor enjoyment, future enhancements, gardening, recreation, or simply enjoying the tranquility and privacy of Southern Maryland living. Located just minutes from shopping, dining, commuter routes, military installations, and the waterfront charm of historic Port Tobacco, this extraordinary property delivers the perfect balance of luxury, privacy, convenience, and space. Property Highlights: * 5 Bedrooms | 5 Full Baths | 1 Half Bath * Over 5,200 Finished Square Feet * 3.8 Private Wooded Acres * Main-Level Primary Suite * Additional Upper-Level Luxury Primary Retreat * Home Office * Formal Living & Dining Rooms * Crown Molding & Chair Rail Details * Dual-Access Waterfall Staircase * Great Room with Stone Gas Fi

7980 Norwich Ct, Port Tobacco
$298,000
MDCH2056748 MLS
This 15.09+/- residential zoned parcel has 4 approved perc sites and 2 potential lots. The rolling terrain and open space create an ideal setting for custom homes, or long-term land investment. Conveniently located with easy access to major roadways, shopping, dining, and local amenities, this property combines the tranquility of a rural setting with the convenience of nearby services. Whether you're a builder, developer, investor, or future homeowner, this 15.09-acre parcel presents a rare opportunity to secure a versatile piece of land with outstanding potential.

Locust Grove Dr, Port Tobacco
$250,000
MDCH2056560 MLS
Unrivaled privacy meets exceptional strategic value with this premier 10.6-acre wooded tract in historic Port Tobacco. This expansive acreage is zoned Rural Conservation (RC), making it a ideal canvas for buyers envisioning a private custom estate, a secluded compound, or a long-term land investment footprint in Charles County. An additional adjoining 3 acres is available for purchase (MLS: MDCH2056558). A standout feature of this property is its verified building potential. In 2018, three percs were officially recorded, providing essential peace of mind and significantly accelerating the timeline for your custom construction plans. A portion of this land is currently protected under a permanent Forest Conservation Easement. Far from a limitation, this easement provides immediate and lasting advantages to the future property owner. It guarantees that a significant section of your land will remain a beautifully preserved, mature wooded sanctuary, establishing a permanent natural privacy buffer that can never be cleared by future neighbors. This environmental protection also ensures an abundance of local wildlife, preserves pristine air and water quality, and shields the property from local soil erosion. Furthermore, land encumbered by a conservation easement qualifies for favorable local tax assessments, lowering your ongoing holding costs while maintaining a peaceful, deep-green canopy backdrop for your new home. While the property delivers a profound sense of absolute wilderness and quiet isolation, it keeps you closely tied to major regional hubs and commuter infrastructure. The property is situated just about 7 miles from the bustling commercial and shopping corridors of Crain Highway (MD-301) in La Plata, and approximately 10 miles from Indian Head Highway (MD-210), providing a straightforward, reliable commute directly into the Washington D.C. metropolitan area, local military installations, and regional employment centers. Whether you are a custom home builder looking for a high-end lot with established utility potential, or an individual searching for a quiet acreage sanctuary to secure your family legacy, 8710 Poorhouse Road delivers space, natural beauty, and a highly accessible location. Complete perc mapping and detailed easement boundary documentation are available under the listing documents. Bring your builder, bring your blueprints, and explore the immense development flexibility of this premier Charles County land asset today!

8710 Poorhouse Rd, Port Tobacco
$175,000
MDCH2056558 MLS
A rare blend of absolute rural seclusion and verified potential, this 3 acre wooded parcel in historic Port Tobacco offers an incredible canvas for your dream or strategic land investment. Zoned AC (Agricultural Conservation), this beautiful acreage is tailored for those seeking a peaceful, private sanctuary sitting on high wrapped in Southern Maryland’s deep natural beauty. A massive advantage for any buyer is the property's extensive, proven utility infrastructure. The land features an impressive six (6) percs, recorded in 2018, completely mapping out your future building footprint and providing total peace of mind before you even break ground. For detailed visual layouts of the property lines and soil sites, please reference the "Perc Map.pdf" file included in the listing documents. Adding immense value and privacy, this 3 acre parcel directly adjoins 8710 Poorhouse Road (MLS: MDCH2056560), a premier 10.6 acre listing with a Forest Conservation Easement. This proximity ensures your estate will be flanked by a mature wooded buffer with a feeling of a quiet tranquility, local wildlife views, and scenic natural screening. While the property feels like a deep wilderness escape, it maintains exceptional commuter and urban access. You are located just about 7 miles from the extensive shopping, dining, and commercial conveniences of Crain Highway (MD-301) in La Plata, and approximately 10 miles from Indian Head Highway (MD-210). This strategic placement delivers a smooth, direct commute into the Washington D.C. metro area and regional employment hubs while letting you return home to total peace. Bring your custom blueprints and your preferred builder to explore this ready-to-build Charles County gem today!

Poorhouse Rd, Port Tobacco
$774,900
6 Beds ⋅ 5 Baths ⋅ MDCH2056184 MLS
**Rare opportunity! Existing loan is assumable at an incredible 2.75% interest rate for qualified buyers. Buyer must meet lender qualifications and assumption requirements.** !!Price Improvement to $774,900!!! Nestled in the desirable Longmeade neighborhood, this stunning 6-bedroom, 4.5-bath home spans 3 finished levels of over 5500 square feet on a private 2.33-acre lot has just improved their price. The main level features an open floor plan with hardwood floors, a gourmet kitchen with granite countertops and stainless-steel appliances, a family room, sunroom, formal dining, library, and office space. Upstairs, you'll find 5 bedrooms, 3 updated bathrooms, and a versatile open space. The fully finished lower level includes a 6th bedroom, kitchenette, full bath, and entertainment area with a walkout to the yard. The beautifully landscaped lot boasts a koi pond, fenced garden, composite deck, and a 3-car garage with ample driveway space. New HV in January of 2023, New AC and Water Heater in July 2024, New Skylights in November of 2023, New Washer and Dryer in 2024, and New Dishwasher, Double Oven, and Cooktop in April of 2025. Conveniently located near shopping, dining, schools, and major highways for easy commuting. Don’t miss out on this beauty!

8085 Norwich Ct, Port Tobacco
$985,000
5 Beds ⋅ 6 Baths ⋅ MDCH2055860 MLS
Nestled on a quiet cul-de-sac in a private, picturesque setting, this impressive Colonial-inspired estate offers timeless grandeur, exceptional craftsmanship, and over 7,200 square feet of elegant living space designed for both entertaining and everyday comfort. A stately presence and grand entrance welcome you into a home filled with architectural details rarely found today. Ten-foot ceilings, extensive crown molding, chair rail, wainscoting, custom built-ins, and exquisite woodwork create warmth, character, and sophistication throughout. Designed for hosting on any scale, the formal living room and formal dining room each feature a working fireplace with custom mantels. The dining room is complemented by a true butler's pantry with floor-to-ceiling shelving nearly 10 feet high, creating a seamless connection to the beautifully updated kitchen. Home chefs will appreciate the expansive workspace, granite countertops, double ovens, abundant cabinetry, and effortless flow into the spacious family room with a gas fireplace and extensive built-in bookcases. Just off the family room is a private office, while a substantial addition offers incredible flexibility. Previously used as a successful home business, this space includes a full bath and office area and could easily serve as a main-level primary suite, guest quarters, or multi-generational living space. The second level is highlighted by an exceptional primary suite featuring its own wood-burning fireplace and an extraordinary walk-in closet with a footprint comparable to the three-car garage below. The spa-inspired en-suite bath offers a soaking tub, separate shower, dual vanities, and access to an adjoining room currently used as a dressing room, but equally suited as a private study, nursery, or additional bedroom. Two additional spacious bedrooms with custom built-ins share a well-appointed full bath, completing this thoughtfully designed level. The third floor provides even more living space with two additional bedrooms, individual mini-split HVAC systems for comfort and efficiency, and a shared full bath. The fully finished lower level is ideal for entertaining, extended family, an au pair suite, or in-law apartment. Complete with a full kitchen, recreation room, full bath, den or sleeping area, exercise room, and generous storage, the space opens directly to a large screened porch overlooking the gardens and outdoor entertaining areas. With four working fireplaces, a three-car garage, an extended driveway with ample parking, and endless possibilities for home business, multi-generational living, or gracious entertaining, this remarkable estate offers a rare combination of elegance, functionality, and enduring charm. Located in Northern Charles County, just minutes from major commuter routes to Washington DC.

9015 Katie Ct, Port Tobacco
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