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.
Step into this absolutely beautiful 2-story home with a basement, where pride of ownership shines from the moment you walk through the front door. Offering approximately 3,900 finished square feet, this home features stylish LVP flooring and cozy carpet throughout, with spacious bedrooms and a layout that’s both functional and inviting. The heart of the home is the large kitchen, complete with leathered granite countertops, stainless steel appliances, and plenty of space to cook, gather, and entertain. Plus, enjoy the convenience of a brand new washer and dryer already in place! Downstairs, the sellers have finished a large portion of the basement—currently used as additional living space and a bedroom—with a bathroom rough-in already in place, giving you endless options to customize. Create the ultimate movie theater, man cave, home office, gym, or guest suite—the possibilities are wide open. To top it off, a new electric garage door will be installed prior to settlement. This home has been well cared for and it truly shows—move-in ready and waiting for you!
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, it’s 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 and minutes to Easton. The single-level home features 3 bedrooms and 2 full bathrooms, a country kitchen, and an open-concept layouthighlighted 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 structureready for customization. Toward the rear of the property is an additional structure with 1 bedroom, 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 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 appeal for outdoor enthusiasts and waterfowl hunting. This property is being sold As-Is and is priced to sell, presenting a rare opportunity to own a fully fenced acreage property with multiple structures and flexible use potential on Maryland’s Eastern Shore.
Charming Eastern Shore property set on a peaceful stretch of Seaman’s 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.
**Accepting other offers** Situated on 4.14± private acres, this 3-bedroom, 2.5-bath home couples serene country living with exceptional craftsmanship. Inside, the first floor offers a formal dining room, large eat in kitchen with stainless steel appliances, vaulted ceiling living room with two story stone fireplace, first floor primary with walk in closet and Whirlpool tub, office with built ins, and sunroom. Upstairs, 2 well sized bedrooms sit at each side of the home, connected by an overlook to the living room. The oversized 2-car attached garage provides plenty of storage and includes a finished room above with mini-splits, creating a flexible space for guests, office, or hobbies. Outside, the property is equipped for both recreation and function, featuring an in-ground pool, a large pole barn with electric, and two additional sheds. The rural setting provides privacy and a quiet environment while still allowing convenient access to nearby towns.
Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and extra space for modern living. Outside, you’ll find an oversized shop/garage ideal for hobbies, storage, or a workshop. The property also includes a home generator, adding peace of mind. While the home does need some work, it has great bones and endless potential to become a stunning residence once again. Bring your vision and breathe new life into this timeless property.
Peaceful Country Living on 3.2 Acres – Recently Renovated Home with Expansive Pole Barn! Welcome to 21405 Tanyard Rd in Preston, MD – where modern updates meet serene country living. This beautifully renovated 3-bedroom, 3-bath home sits on 3.2 acres—perfect for gardening, raising animals, or simply enjoying wide-open space and quiet surroundings. Step inside to find a bright, freshly updated interior with modern finishes throughout. The spacious layout offers room for everyone, with a beautifully refreshed kitchen, inviting living spaces, and well-appointed bedrooms and bathrooms designed for comfort and convenience. Outside, the property truly shines. A massive 47x70 pole barn provides endless possibilities—featuring a workshop area, abundant storage for vehicles, equipment, or hobbies, and space that’s ideal for anyone who needs room to work or play. Enjoy the best of both worlds: peaceful country life and the convenience of Easton being just 10 minutes away. Whether you’re looking for a homestead, hobby farm, or your own private retreat, this property offers it all. PROPERTY IS BEING SOLD AS-IS AND Inspections are for informational purposes ONLY. Cash and Conventional Financing
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.
***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. It’s 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. Don’t 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!
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 chef’s 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 butler’s 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 estate’s 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 property’s 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.
Charming Renovated Home in Choptank, Preston MD Additional Photos coming. This home is currently getting a fresh coat of interior paint, new appliances and updates coming. It will be turn key ready 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. New 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.
This is not a to-be-built. This home is complete and ready for occupancy. Discover a stunning new construction home that embodies modern luxury and comfort. This exquisite ranch-style residence, completed in 2025, offers a harmonious blend of elegance and functionality, set on a generous 1.16-acre lot that provides ample space for outdoor enjoyment. Step inside to find a thoughtfully designed layout featuring three spacious bedrooms and two full bathrooms, all crafted with meticulous attention to detail. The interior boasts a seamless flow, enhanced by high-quality luxury vinyl plank flooring that exudes sophistication while ensuring durability. Plush carpeting in the bedrooms adds a cozy touch, creating inviting retreats for relaxation. The heart of the home is the gourmet kitchen, equipped with energy-efficient stainless steel appliances that cater to both culinary enthusiasts and everyday cooks alike. Natural light floods the living spaces through strategically placed windows, creating a warm and inviting atmosphere throughout. The open-concept design encourages effortless entertaining, allowing you to host gatherings with ease while enjoying the comfort of your new home. The exterior of the property features durable vinyl siding, ensuring low maintenance while maintaining a polished appearance. An attached front-entry garage provides convenient access and ample storage, making daily life a breeze. This home is not just a residence; it's a lifestyle choice. With its excellent condition and modern amenities, it offers a sanctuary where you can unwind and recharge. The expansive lot invites you to explore outdoor possibilities, whether it's gardening, hosting barbecues, or simply enjoying the tranquility of your surroundings. Experience the perfect blend of luxury and comfort in this exceptional property, where every detail has been carefully curated to enhance your living experience. Embrace the opportunity to make this beautiful home your own.
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!
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!
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.
Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank views and no houses on the opposite shoreline. Upon walking into the home, this same goal is achieved with large windows along the water side providing sweeping views. The river room has glass all of the way around flooding the space with light and perfect for reflection or entertaining. Hardwood floors bring serious charm and warmth to the home. The primary bedroom is spacious and includes an ensuite bathroom while the other two bedrooms provide river views. An oversized 2 car garage allows extra space to mess around on your workbench and store those beloved kayaks. The large and cleared yard has a split rail fence and trees that along with the meandering paved driveway provide a sense of privacy. The community itself is very quiet and has the Jim and Mary B. Lynch Preserve adjacent which provides roughly 2 miles of walking trails and is currently managed by the Eastern Shore Land Conservancy. Make this your own tranquil Eastern Shore retreat.
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
New construction in Preston, MD offering 3 bedrooms and 2 full baths across 1,400 square feet. This home features an open layout with vaulted ceilings, LVP flooring in the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances and granite countertops. The primary suite includes a stand-up shower, while the guest bath offers a tub/shower combo. An attached two-car garage completes the home.
NEW PRICE! Two Tranquil Country Acres with No Restrictions, backs to open farmland. Deep Back Yard includes an above ground pool with a deck for your summer enjoyment, large vinyl fenced area for pets and kids, more fenced area for farm animals (pets) and includes a shooting mound should that be of interest. This lovely home Boasts 2,667 Sq. Ft. of Family Space with new LVP flooring though out the main floor and loft area on the upper floor. Your family will enjoy the the roomy country kitchen / dining area overlooking the back yard and the main floor Primary Suite. Head upstairs a versatile loft area - perfect for a study or game space. A large bedroom takes up one end of the upper floor and just outside is a full bath. Just beyond the loft area you will find another bedroom with an attached full bath and just beyond this is a generous bonus room that could serve and a game room for the kids or a Man Cave. This Family home includes a two car wide paved drive and Full Size Two Car finished garage. A lot to offer, come take a look!
Charming 3-bedroom, 1-bathroom mobile home on 1.37 acres with plenty of room to grow! This well-maintained, one-family-owned property boasts numerous recent upgrades, including a new roof (2024), hot water heater (2023), new appliances and countertops (2024), fresh paint (2024), new fencing (2024), and a brand-new septic system. The oversized 2-car garage provides ample storage or workspace. Inside, the primary bedroom features an attached bonus room, ideal for a future second full bathroom. The property also includes the spacious side yard to the left of the home, offering even more usable outdoor space. Zoned Village Commercial, this property provides exceptional flexibility for residential living or potential business use. A rare find that combines comfort, opportunity, and room to expand!
Owner relocated & says sell. Escape to country living on this 9+ acre mini farm with updated 3/4BR home, 4-5 acres cleared & the rest wooded just a few miles from Easton, hospitals, shopping, doctors, boat ramps/river, airport and parks but in beautiful private setting. Low AG taxes as local farmer has been planting the front field. Bring the animals, 4 wheelers, home based business, hunt and have some fun or relax in this private oasis. Deer & turkey spotted frequently. Lots of room to expand or build a barn. Handicap ramp to back door and 1st floor bedroom(s) and bathroom. The second first floor bedroom could be an office or dinning room. New HVAC, granite kitchen counters, all new appliances, fresh paint and more.
Preston is located in Maryland. Preston, Maryland has a population of 951. Preston is more family-centric than the surrounding county with 52.46% of the households containing married families with children. The county average for households married with children is 27.43%.
The median household income in Preston, Maryland is $63,750. The median household income for the surrounding county is $63,027 compared to the national median of $69,021. The median age of people living in Preston is 34.3 years.
The average high temperature in July is 88.4 degrees, with an average low temperature in January of 27.2 degrees. The average rainfall is approximately 45.4 inches per year, with 11.4 inches of snow per year.
