Preston MD Real Estate & Homes for Sale

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.

Nestled in Dover Bridge Mobile Home Park-formerly Prettyman Manor-this double-wide manufactured home sits on one of the largest lots in this peaceful community. The property offers plenty of space and potential, with a few upcoming improvements to help set the stage for its next owner. While it could use a bit of attention, its a wonderful opportunity to make this home your own in a quiet, welcoming setting. Conveniently close to Easton, 40 minutes to Bay Bridge.

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. The seller is offering up to $15,000 toward the buyers closing costs with an acceptable offer. This property is being sold As-Is and presents a rare opportunity to own fully fenced acreage with multiple structures and flexible-use potential on Marylands Eastern Shore.

Charming Eastern Shore property set on a peaceful stretch of Seamans Road in Preston, MD. Enjoy the tranquility of country living with convenient access to nearby towns, outdoor recreation, and local amenities. A great opportunity for those seeking space, privacy, and small-town charm.

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

Price Reduction! Well built and lovingly maintained 3 bedroom, 2 bath rancher on 1 acre. New roof installed 2024. Nice open yard with established shade trees around the house. Small barn at rear of the property.

A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind property. The main residence spans over 9,364 square feet and is thoughtfully designed for refined living and grand-scale entertaining. A dramatic two-story foyer with sweeping double staircases opens to richly appointed formal and informal living spaces accented by custom millwork, crown moldings, hardwood flooring, and four fireplaces. At the heart of the home, the chefs kitchen impresses with coffered ceilings, expansive island, commercial-grade range, double wall ovens, and premier Viking, Sub-Zero, and Wolf appliances, along with an induction cooktop and icemaker. A well-appointed butlers pantry ensures seamless entertaining, while the adjoining Grill Room-featuring an infrared grill, Viking beverage cooler, and Sub-Zero icemaker-offers a relaxed gathering space. The primary suite is a private retreat with fireplace, mood lighting, generous walk-in closets, and dual doors leading to a private balcony overlooking the grounds. The spa-inspired bath includes double vanities, a tiled shower, and soaking tub. All additional bedrooms in the main residence are ensuite, offering comfort and privacy for family and guests. Outdoor living rivals a private resort, highlighted by a 40 x 20 heated saltwater infinity pool with swim ledge, hot tub, outdoor kitchen, covered porch, expansive patios, and firepit-perfect for year-round enjoyment amid mature landscaping, a tranquil pond, and sweeping rural views. Automobile collectors will appreciate the estates unparalleled garage facilities. A detached brick automotive gallery features a nine-bay, climate-controlled showcase garage with CHI aluminum tinted glass doors, polished concrete floors, and premium climate control-ideal for preserving and displaying a museum-quality collection. Above, a fully appointed three-bedroom, two-bath guest residence offers a kitchen and multiple living spaces. Two additional fully insulated, climate-controlled 50 x 75 garages with 12-foot overhead doors and professional-grade lifts provide exceptional flexibility. An oversized storage building and run-in to the rear further enhances the propertys versatility. Hobbyists, from automobile collectors to equestrian enthusiasts, will be delighted to make use of the many large accessory structures on the property. Additional features include a comprehensive security and surveillance system, private gated entrance, 60-zone irrigation system, whole-property surround sound, & Comcast fiber internet. This is more than a home-it is a destination estate offering an elevated lifestyle for those who value privacy, craftsmanship, and automotive excellence in a refined Eastern Shore setting. IMPORTANT NOTES: Property consists of three parcels with separate addresses/taxes, portions of which are leased for agricultural use through December 2025. The irrigation system has a mainline break beneath a garage and will not be repaired by the seller. Quotes for repair or replacement are available for review.in documents. Property sold AS-IS/WHERE-IS with all faults. ***Please do not enter lane to home without a confirmed appointment.

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 todays 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, its the perfect space for vehicles, tools, equipment, a workshop, or the dream home gym youve 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!

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 youll 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.

***Unique Opportunity*** Welcome to this spacious and well-cared-for property located in the peaceful town of Preston. The main home offers 5 generously sized bedrooms and 3 full bathrooms, providing ample space for comfortable family living or multi-generational needs. A large eat-in kitchen serves as the heart of the home, perfect for everyday meals or entertaining guests. This property shines with its versatility. Behind the home, you'll find a large workshop that conveys with the sale. Its an ideal space for hobbies, storage, or small business use. Whether you're looking for extra utility space or a place to grow your passion projects, this shop offers endless potential. Included in the sale are three total parcels. In addition to the main residence, the property next door - previously used as a pet grooming operation - opens the door to commercial opportunities, rental income, or conversion into a guest suite, studio, or office. Behind that is a third parcel, offering even more room to expand, garden, or invest. Dont miss this rare chance to own a truly versatile property with both residential charm and business potential. Call today to make this one-of-a-kind opportunity yours!

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. Dont 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