Preston MD Real Estate & Homes for Sale

Set on 8.6 private, fully fenced acres just across the Dover Bridge, this Eastern Shore property offers endless possibilities with scenic surroundings, expansive land, and close proximity to the Choptank River, just minutes from Easton. The single-level home features three bedrooms and two full bathrooms, a country kitchen, and an open-concept layout highlighted by a massive brick fireplace with insert and beamed cathedral ceilings in the great room, creating a warm and inviting living space. The roof is approximately two years old. The property includes a large patio with an outdoor bar, a chicken coop, and a separate partially built structure ready for customization. Toward the rear of the property is an additional structure featuring one bedroom, a full bathroom, and storage, as well as another separate structure with six bathrooms, offering flexibility for events, gatherings, or agricultural use. A detached two-story barn adds significant value and includes one room, a walk-in closet, and a kitchen with a gas stove, providing potential for guest space, studio, or workshop use. Additional features include a run-in stable, pasture, pond, and expansive open land suitable for farming, homesteading, recreation, or hunting. The nearby Choptank River enhances the appeal for outdoor enthusiasts and waterfowl hunting. The home does need cosmetic updates, and the price reflects its current condition. A rare opportunity to own fully fenced acreage with multiple structures and flexible-use potential on Maryland's Eastern Shore.

Two Johns - Charming Home in a Sought-After Waterfront Community Nestled between Preston and Denton in the desirable Two Johns subdivision, this beautifully maintained 4-bedroom, 2.5-bath home offers a rare blend of comfort, style, and location. Just a few houses away from the public boat landing, residents enjoy easy water access for boating, kayaking, or fishing. Take in serene water views from the second floor, adding a peaceful touch to everyday living. Since 2022, this home has received a long list of thoughtful upgrades, including: New roof Paved driveway Modern kitchen appliances Granite countertops Laminate flooring (2nd floor) Fresh interior paint Ceiling fans throughout New rear sliding door Insulated garage doors Storage shed Professional landscaping Whether you're looking for a full-time residence or a weekend retreat, this home offers the perfect mix of function, beauty, and access to the Eastern Shore lifestyle. Don't miss this opportunity to own in a water-privileged community! The owner has pets and needs notice to accommodate.

Tucked away just outside of town, this charming 3-bedroom, 2-bathroom home offers the perfect blend of privacy and space on a beautiful 4-acre property. The land features a mix of open, cleared yard and mature woods, providing both room to roam and a peaceful natural setting. Inside, the home offers a comfortable and functional layout, ideal for everyday living. One of the bedrooms includes a unique addition that was previously used as an art room, offering endless possibilities as a creative studio, home office, or private retreat. Outside, the property truly shines. A spacious 3-car garage provides plenty of room for vehicles, storage, or a workshop. The screened-in gazebo is the perfect spot for relaxing or hosting gatherings, whether you're enjoying summer evenings with family or spreading out a feast of steamed crabs with friends. With its quiet location, versatile spaces, and scenic surroundings, this property offers a rare opportunity to enjoy country living while still being within reach of town conveniences.

Welcome to this beautiful 3-bedroom, 2-bathroom home filled with wonderful updates throughout. As you arrive, you'll immediately notice the brand-new roof, offering peace of mind for years to come. Step inside to discover a stunning updated kitchen featuring quartz countertops and stainless steel appliances, perfect for both everyday living and entertaining. With spring just around the corner, imagine relaxing on the deck off the back of the home, overlooking the spacious backyard - an ideal setting for outdoor gatherings or quiet evenings. Down the hall, you'll find two comfortable bedrooms along with a full bathroom on the first floor. Upstairs, retreat to the spacious primary suite, complete with two walk-in closets and a private en-suite bathroom, creating the perfect place to unwind. This home combines modern updates with comfortable living - ready for its next owner to move right in.

NEW PRICE! Enjoy peace and space on two tranquil country acres with no deed restrictions adjacent to open farmland. The deep backyard features a large vinyl-fenced area ideal for kids and pets, an above-ground pool with deck perfect for summer fun. This lovely home offers 2,667 Square feet (estimated) of living space, new LVP flooring on the main floor, and a versitile loft upstairs. The spacious country kitchen and dining area look out over the backyard, and there is a primary suite on the main floor. Upstairs, a flexible loft is great for a study or recreation area. One bedroom occupies one end of the house with a nearby full bath, while another bedroom and full bath are found just beyond the loft, followed by a generous bonus room that could be used as a game room or man cave. Additional amenities include a wide paved driveway and a full-size two-car garage. With its extensive features and inviting atmosphere, this family home presents a compelling opportunity - schedule a viewing today!

Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture. There is even a storage shed on the property.

Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style. Enjoy the screened-in rear patio overlooking a generous 1.5-acre lot - perfect for relaxing, entertaining, or outdoor activities. Additional highlights include two well-maintained outbuildings, ideal for storage, workshop space, or hobbies. Whether you are seeking a primary residence, second home, or investment opportunity, this property presents tremendous potential in a desirable Eastern Shore location. Being sold strictly AS-IS as part of an estate sale. The home will require repairs and is best suited for buyers looking to renovate and bring their vision to life. Crawl Space mold remediation is being completed by the sellers.

A perfectly situated, water-oriented, turnkey, rancher with a piece of country is ready for your enjoyment. Produce your own vegetables, flowers or the like in the already established rear garden beds, collect your peaches, pears and other fruits from fruit bearing trees. Start your plants early in an enclosed greenhouse/produce stand. Complete your 4H projects. A second greenhouse area is framed and ready for a canopy. Utilize the two recently fenced in areas with separate gated access as needed. A large storage shed with electric could be your workshop. An additional outbuilding is available within the farm fencing for your gardening tools and has room for animals. Store your trailable boat under the carport when not using it on the navigable Choptank River from Ganey's Wharf waterfront park and boat launch. Ganey's Wharf is within 1/2 of a mile of your mini homestead! Relax on the front porch or rear landing to take in the views. Mature growth woods exist on the sides of the property and across the street. Within home is a primary bedroom suite with a jacuzzi, separate shower, and a walk-in closet. A second bathroom, located off the hallway to two bedrooms, divides bathing area from toilet area (water closet) and includes a linen closet. The two hallway bedrooms include lighted ceiling fans. Also, off of the hallway is a large utility room with a washer and dryer. A fourth bedroom/office contains built in cabinetry. The primary bedroom and the fourth bedroom/office are located on one side of home while the two other bedrooms are on the opposing side of home offering privacy with a central great room and eat-in kitchen between. The property is serviced by Choptank Electric and Fiber. A subscription ready security system is in place. All appliances, window treatments, runner, carpet, some furniture, some garden tools, and grills are included in this sale. Don't be late. It is time to prepare your gardens and get ready to take in the views from the waterfront park and all that you can experience from the scenic and bountiful Choptank River. Just minutes from Easton (20), Denton (15), Cambridge (35), and tax-free Delaware shopping by car. Annapolis is 1 hour by car.

Step back in time with this early 1900s home. This home is full of character, from the detail in the trim work to the upper level 'porch.' This home offers great potential to be returned to the early 1900s with a little TLC and vision. Located in the heart of Preston, it is 15 minutes from historic Easton with all its amenities. Come take a look and see the vision.

Totally renovated colonial offering nearly 2,000 sq ft of living space on a spacious 1/3-acre corner lot. Featuring 3, possibly 4 generous bedrooms and 2 full baths, this property showcases luxury vinyl plank flooring throughout. Enjoy privacy rear fencing and a large backyard - perfect for outdoor living. Ideal for a growing family and conveniently located close to Easton and Preston. This home is a must see!

This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential services.

VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXIMATELY 1/4 MILE AWAY. LARGE LIVING ROOM, KITCHEN-DINING ROOM COMBO, PANELED WALLS ARE ALL PAINTED, MOSTLY WOOD FLOORS. LARGE DECK AT REAR OF HOUSE. PATIO AREA WITH A NICE FIRE PIT FOR EVENING ENJOYMENT. MORE PICTURES TO COME SOON. ONLY 40 MILES TO WESTERN SHORE, LESS THAN 60 MILES TO THE BEACH

Set on a private, wooded 1.37 acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open to a spacious screened-in porch and adjoining deck overlooking the fenced backyard and mature trees. The spacious first-floor primary suite includes direct access to the screened porch, a private primary bathroom with two granite-topped vanities, a jetted soaking tub, a tiled walk-in shower, a private water closet, and a walk-in closet with attic access. Upstairs you'll find three additional bedrooms, a full bath, and a bright bonus room offering flexible use. A fully finished third-floor loft provides exceptional additional living space - ideal for a family room, game room, or creative studio. Fresh interior paint, newly painted exterior shutters, and a new roof add to the move-in-ready presentation. The home benefits from meaningful system updates, including a recently replaced HVAC unit and a new well pump. A peaceful setting convenient to both Easton and Denton, this property offers space, privacy, and a beautifully maintained home ready for its next owner.

Price Reduction! Well built and lovingly maintained by the original owner. This 3 bedroom, 2 bath rancher featuring oak floors, central air, a brick fireplace and is situated on 1 acre. This home is conveniently located and move in ready. A new roof was installed in 2024. Nice open yard with established shade trees around the house. Three season porch for casual entertaining or enjoying a crab feast with family and friends. Small barn with cement floor at rear of the property.

Welcome to this beautifully updated rancher that checks every box - and then some. Sitting on over half an acre, this home blends modern upgrades, spacious living, and incredible functionality, all wrapped into the perfect Eastern Shore retreat. Step inside to find new LVP floors, fresh siding, and a brand-new roof, giving the home a crisp, clean, move-in-ready feel. The heart of the home is the large family room, featuring soaring vaulted ceilings that flood the space with natural light and make every gathering feel special. With 4 generous bedrooms plus a dedicated office, this home offers the flexibility and layout today's buyers need, whether you work from home, need extra guest space, or want room for hobbies and play. Each bedroom is impressively sized, offering comfort and privacy for the whole household. The full basement adds even more possibilities, storage, workshop space, future finishing potential, or a rec area designed exactly the way you want it. Car enthusiasts, hobbyists, and anyone craving storage will fall in love with the 31' x 27' oversized detached garage. Complete with electric, it's the perfect space for vehicles, tools, equipment, a workshop, or the dream home gym you've been imagining. Outside, enjoy the peace and elbow room of a large lot with plenty of open space for entertaining, gardening, play areas, or simply relaxing in your own private slice of the Shore. Homes with this combination of updates, space, and functionality are incredibly rare. Do NOT pass this one up , this property is truly a MUST SEE!

Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you'll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or enjoying everyday meals with ease. Thoughtfully designed living spaces provide both comfort and functionality throughout. What truly sets this property apart is its incredible versatility. Just behind the home sits a large workshop that conveys with the sale, ideal for hobbies, storage, a small business, or creative projects. Whether you're an entrepreneur, craftsman, or simply need extra space, this shop offers endless possibilities. This is a unique opportunity to own a property in downtown Preston, MD, combining small-town charm with space and functionality. Schedule your showing today and discover all the possibilities this one-of-a-kind Preston property has to offer.

Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don't miss this beautifully completely renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of Choptank. Every inch of this home has been thoughtfully updated from top to bottom, blending modern finishes with classic Eastern Shore charm. Pella windows. Heat pump. Updated Septic. Previously used as a rental home, this home offers investment potential or the perfect retreat. Walking distance to Choptank Marina. Enjoy local crabbing, fishing, and boating nearby. Peaceful, small-town setting on Maryland's scenic Eastern Shore. Whether you're looking for a primary residence, weekend getaway, or income-producing property, this move-in-ready home offers it all.

Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates. Whether you're looking for a primary residence or an investment opportunity, this property offers great bones and endless potential. Enjoy the tranquility of rural living while still being just minutes from Easton conveniences and the Choptank River. With a little vision and creativity, this home could truly shine. Don't miss your chance to own a piece of Caroline County at an incredible value! This home is being sold as-is. At one time the garage was a finished inlaw apartment and could easily be converted back to include an additonal bedroom and bathroom with heat and air

Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County