507 properties for sale in Preston town, District 4 Preston Caroline County Maryland

Step into a piece of Eastern Shore history with this charming, beautifully maintained American Four Square, where original craftsmanship and timeless character create a home that feels truly special. Original doors, staircase, picture windows, plaster and lath walls, beautiful trim and floors, classic built-ins, and a welcoming wraparound porch evoke a simpler pace of life. Adding to the property's unique story is the retired U. S. Post Office building, a remarkable historic feature that gives this property a sense of place and a connection to the towns rich history. With its own parking, the Post Office offers an excellent opportunity for an on-site professional office or cottage industry. Inside the house, 3 bedrooms and 2.5 baths are complemented by a country kitchen with newer appliances, downstairs laundry, parlor, living room, and formal dining room with built-in cabinetry. Upstairs, the original bath has been renovated and features an antique mahogany vanity matched with the ori

Investors two units, separate meters & two potential income streams! Opportunity awaits at 526 Pine St in Cambridge! This duplex offers two separate 2-bedroom, 1-bath units, each with its own private entrance and separately metered utilities, making it an attractive setup for an investor looking to renovate, rent, and add to their portfolio. The property offers approximately 1,144 square feet above grade and includes a rear parking pad for convenient off-street parking. With two independent units already configured under one roof, the property offers excellent value-add and income-producing potential. Nearby rental activity suggests potential rents around $1,200+ per month per unit depending on condition and improvements, creating the potential for approximately $2,400+ in combined monthly gross rent. Buyers should independently verify achievable rents, legal unit count, licensing, and permitted use. Whether you're looking for your next rental property, multifamily renovation project,

Welcome home to 308 Glen Oak Circle! This charming two-story Cape Cod offers 4 bedrooms and 2 full bathrooms, providing plenty of space and flexibility for comfortable living. Situated on a 0.26-acre lot, this home features several recent updates, including a newer HVAC system installed in 2024, newer windows from 2023, and a newer roof from 2022. Solar panels add an energy-conscious feature to the property. The classic Cape Cod design offers a functional layout with plenty of opportunity to make the home your own. Outside, enjoy a spacious yard and a welcoming setting in Hurlock. With its classic charm, generous lot, and numerous recent updates, 308 Glen Oak Circle is ready for its next owner. Dont miss this opportunity to make this charming Hurlock home your own!

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors

Solitude on Edge Creek with over 300+/. Feet of tranquil waterfrontage and protected shoreline. Five-foot-wide pier with ample room for boats, substantial boat lift and 2-3+/. Feet mean low water. A private, serene Eastern Shore retreat on manageable 3+/. Acres with its very own nature walking-trail. The park-like setting features southeast exposure, a multitude of beautiful, specimen trees, and waterside pool with shaded patio. The additional charming and practical one bedroom guest house with separate kitchen offers a sanctuary for any weekend visitors. The main house includes first and second floor primary suites with views of the creek and all its natural inhabitants, an additional 3 bedrooms (one with en-suite bath), a total of 4 1/2 bathrooms, a terrific light-filled, large sunroom and waterside deck. Conveniently located close to the wonderful dining at The Oaks Waterfront Hotel and t at The General Store, while also not far from the Bellevue Ferry to historic Oxford, MD or shop

Nestled in the serene community and quiet court of The Woods at Stoney Ridge, this beautiful Colonial offers an inviting blend of elegance, comfort, and thoughtful updates throughout more than 3,300 square feet of living space. The interior showcases elegant crown molding, hardwood floors, and plush carpeting, creating a warm and welcoming atmosphere. The functional, yet spacious kitchen is designed for both everyday living and entertaining, featuring a spacious peninsula island and quality appliances, including a self-cleaning oven and built-in microwave. Gather in the cozy family room, complete with a gas fireplace, or retreat to the private main level primary suite, where a generous walk-in closet and spa-inspired bath with both a walk-in shower and soaking tub provide the perfect place to unwind. A convenient main-level laundry room and partially finished walkout basement offer added functionality and flexible living space. Additional highlights include a two-story, two-car garage

Welcome to the most charming historic colonial to hit the Eastern Shore during this fall market! Priced to sell, this stunning single family residence offers tons of natural light, new flooring throughout, fresh paint, a clean kitchen aesthetic and a spa like bathroom on the second level. The backyard extends for plenty of parking space, gardening opportunities, space to host or build a fire pit and more! The owners put love into this house to make sure its new family can really enjoy going into the holidays with real peace of mind. Make sure to schedule your private showing with the listing agent today!

Welcome to 112 Glenwood Avenue, a charming and affordable home in the heart of Easton! Built in 1946, this home offers the character and charm of an earlier era while featuring updates for todays lifestyle. With 2 bedrooms, 1 bath, 912 square feet of comfortable living space, NO HOA, and a convenient downtown location, this home has plenty to offer. Freshly painted and move-in ready, the home features new carpet in both bedrooms, a NEW ROOF, a gas range, and a fenced backyardperfect for pets, gardening, entertaining, or simply enjoying your own outdoor space. One of the highlights of this home is its walkability! Youre just a 6-minute walk to the Avalon Theatre and other downtown Easton attractions, including coffee shops, restaurants, shopping, galleries, and more. The home is located across from the Easton Police Department and just half a block from the elementary school, putting so much of Easton within easy reach. Easton is a wonderful place to call home, offering the charm and ch

Easton Club. Comfort and Convenience! Beautiful natural light, a spacious end-unit setting and the ease of first-floor living. This four-bedroom, three-bath townhouse features a generous great room with gas fireplace opening to the kitchen and dining area with Corian countertopsan inviting space for everyday living and entertaining. The first-floor primary suite offers a private bath with walk-in shower and dual vanities, while an additional main-level bedroom, full bath and laundry add to the convenience. Upstairs, two bedrooms, a family room and a large storage room provide plenty of space and flexibility. Enjoy outdoor living on the patio and in the fenced yard, with a corner lot and attached one-car garage completing the property. Ideally located along the desirable Oxford Road corridor, Easton Club offers a community pool and tennis/pickleball court, just a short drive from downtown Easton and Oxford

ONLINE AUCTION: Bidding begins 10/29/2026, 10:00 AM. Bidding ends 11/2/2026, 1:20 PM. List Price is Suggested Opening Bid. Deposit: $5,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Mobile Home located in the Active 55+ Hyde Park Community in Talbot County. Enjoy the convenience of Easton's historic downtown, dining, shopping and arts scene. Easy access to parks, trails and the Tred Avon River. Easy access to major traffic artery US-50 (Ocean Gateway). Property is vacant

Adorable curb appeal, major updates, and room to make it your own! This charming 4-bedroom, 1-bath home at 522 Denton Road offers a great opportunity for buyers looking to add their personal touch without tackling all the big-ticket projects! The seller has already done much of the heavy lifting with remodeling, a new roof, new windows, and a brand-new septic system to be installed prior to settlement. Outside, you'll find two pergolas and a detached one-car garage, adding even more possibilities to this property. With its inviting exterior, important improvements, and plenty of potential left to make it your own, this home is ready for its next chapter. The hard work has started, now bring your vision and make it yours!

Experience effortless luxury at 2700 Willow Oak Drive, nestled within the prestigious waterfront setting of the Hyatt Regency community. Offered completely fully furnished with exquisite, high-end taste, this turnkey residence blends sophisticated coastal design with ultimate convenience. Step inside to discover a bright, beautifully curated interior where every detail has been thoughtfully considered. Enjoy stunning views, premium finishes, and a seamless layout designed for both relaxing and entertaining. Located just moments from the region's finest golf, dining, and resort amenitiesthis is resort-style living at its absolute finest. Simply pack your bags and move right in!

HOME TO BE BUILT by Bay to Beach Builders, Inc. Welcome to'The Oxford', a thoughtfully designed new construction home to be built in a peaceful waterfront neighborhood just a short walk from the Choptank River. This inviting home offers a beautiful blend of style and functionality, with an attractive exterior and a welcoming layout designed for comfortable everyday living. The home will be built on this desirable lot, offering the opportunity to enjoy the quiet surroundings while remaining conveniently close to Cambridge amenities. Buyers will have the opportunity to personalize their home with selections such as siding color, flooring, countertops, cabinetry and other finishes, subject to builder specifications. Build the home you've envisioned with the quality and craftsmanship of Bay to Beach Builders, Inc. Photos are representative of the proposed home and are for illustration purposes only. Final finishes, features and selections are subject to builder specifications and buyer sel

Beautiful new construction in a charming, up-and-coming community! This 3-bedroom, 2-bath home features an open-concept layout with luxury vinyl plank flooring throughout the main living areas. The spacious kitchen offers granite countertops, modern finishes, and seamless flow into the living and dining spacesperfect for entertaining. Built for peace of mind with 30-year architectural shingles and energy-efficient features. Interior photos are of similar home. Buyer to pay 50% of impact fees

Enjoy the charm of Oxford at 105 E. Pier Street! This inviting three-bedroom, two-bathroom home features a kitchen with an eat-in area and three spacious bedrooms, including a primary bedroom with vaulted ceilings and a large walk-in closet. Relax on the front porch beneath the shade of a beautiful oak tree, or unwind on the back porch overlooking the town park, with basketball, pickleball, and tennis courts, a large field for soccer, and a walking trail right outside your door. Oxfords walkable setting makes it easy to enjoy local favorites, from Docs Restaurant to the Highland Creamery, along with the Strand, waterfront park, dog park, and community garden. Several marinas and docking locations throughout town offer options for keeping your boat nearby, subject to availability. A wonderful opportunity to enjoy the relaxed lifestyle of this waterfront town!

Motivated sellers! Exceptional opportunity to own 33+ acres of private Eastern Shore countryside! This charm-filled 3 BR / 2 BA ranch home delivers easy single-story living with 2,160 sq. Ft. an attached 2-car side-entry garage, and spacious main-level accommodations. 3 bedrooms, dining room, den, living room and office. Detached garage/workshop. Highlights include open surrounding views of woods and pastures, ideal for nature lovers, hunting enthusiasts, or those seeking a quiet rural sanctuary. Horse friendly! Great deer hunting! Subdivision potential. Hunting and tilling rights rented for added income. Conveniently located to all Mid Shore locations

Welcome to this 3BR/2.5BA townhome, built in 2024 and located in Pintail Landing. With two assigned parking spaces just steps from the front door, this home offers convenient living in a well-kept community. Step inside to an open-concept main level filled with natural light and featuring recessed lighting, luxury vinyl plank flooring, and a neutral color palette. The living room flows into the kitchen and dining area, creating a connected space for everyday living and entertaining. The kitchen features abundant cabinetry, a separate pantry closet, stainless steel appliances, granite countertops, and a center island with a stainless steel sink and breakfast bar seating. A conveniently located half bath completes the main level. Upstairs, you'll find three bedrooms, a full hall bathroom, and a conveniently located laundry area. The primary bedroom includes a walk-in closet and a private en-suite bathroom with a double-sink vanity and linen closet. Two additional bedrooms offer flexibili

Welcome to this well-loved country home in Cambridge. A short drive to shopping and Cambridge dining. This nicely maintained home features 3 bedrooms, 1 full bath, kitchen, den, living room, office, attic, and laundry room, and is affordably priced. A beautiful wood-burning brick fireplace makes those winter nights cozy. There is a large yard for children, and or pets, a few chickens, and a large 3-car garage for keeping your vehicles out of the weather, or tinkering with your projects. The driveway has room for 4 cars. There's plenty of parking for your vehicles and a fenced patio off the kitchen. Come see this home and make it yours. This one won't last long

One property, endless possibilities! Discover the flexibility and potential of this charming Colonial, ideally positioned along Maryland Avenue at the gateway to historic downtown Cambridge! Whether you're searching for a spacious single-family residence, a place to live and operate your business, or a unique investment opportunity, this property offers the versatility to make your vision a reality. Currently configured as two separate units, this property offers the potential to be converted back into a spacious single-family home with minimal renovations, providing a total of seven bedrooms, two full baths, and one half bath. Prefer to maintain the existing layout? Consider the possibility of living in one unit while utilizing the other for a professional office or business space. With its prominent location and flexible floor plan, the opportunities are worth exploring, subject to applicable zoning requirements and approvals. The main-level unit features three bedrooms, one full bat

Waterfront Community. Updated 4BR/3BA home with Craftsman charm on a corner lot in Longboat Estates. A lovely, established neighborhood of attractive homes and amenities including a community pool, pier, and boatramp on Jenkins Creek which opens to the Choptank River and out to the Chesapeake Bay. Welcoming front porch leads into this gorgeous home. Great floorplan. Boasting nearly 3000sf of well-designed living space, full of architectural detail and quality finishes. Handsome, real hardwood floors, crown. And chair-rail moldings, Corian counters, custom tile. Flexibility is the spice of life, and this home offers plenty! Enjoy a holiday meal in the formal dining room, or linger over your weekend coffee and a crossword at the kitchen breakfast bar. The large breakfast room off the kitchen would also make a great sitting room. Full of sunlight and views of the yard, sliders to the rear porch. Family room off the kitchen is warm with hardwood floors and a gas fireplace. The first floor

Scenic farmland views, peaceful country living, and convenient access to Easton and Prestonwelcome to 30603 Dover Road. Nestled on two acres in Talbot County, this well-maintained brick rancher offers the perfect balance of privacy, comfort, and convenience. Surrounded by the natural beauty of Marylands Eastern Shore, the property enjoys picturesque views of neighboring farmland, expansive lawn, and a tranquil setting just minutes from the everyday conveniences of Easton and Preston. Inside, approximately 2,138 square feet of living space offer a warm and inviting atmosphere. The sun-filled living and dining rooms provide comfortable spaces for relaxing and entertaining, while the generously sized eat-in kitchen serves as the heart of the home. Recently updated flooring throughout much of the main level adds a fresh, welcoming feel. The primary bedroom features a dedicated dressing area, while a second bedroom and full bathroom complete the main-level accommodations. Downstairs, the fi

Victorian Charm with Space, Character & Updates in Sharptown! Discover the charm of small-town living in this Victorian home situated on a corner lot along a quiet dead-end road in the quaint town of Sharptown. Offering spacious rooms, beautiful hardwood floors, 3 bedrooms, and 2 full baths, extra spacious room, this home provides plenty of room to spread out. The extra room could easily be converted into an additional first-floor bedroom, dining or family room offering flexibility to suit your needs. The kitchen features a butcher-block island and pantry, while the floored and insulated third-floor attic provides additional potential living space. Step outside to enjoy the fenced rear yard with a deck and a versatile, Amish-built shed featuring three separate entrances and 220-amp electrical service. The first section offers possibilities for a studio, home office, or greenhouse; the second provides additional storage, while the third is ideal for garden supplies and equipment. Major

Welcome to 107 Sunset Blvd in Preston, MD! This spacious 3-bedroom, 2.5-bath brick home offers comfortable living, thoughtful updates, and everyday convenience. The inviting interior features an open living and dining area with plenty of room to gather, entertain, and make yourself at home. Newer LVP flooring, fresh paint, and upgraded recessed lighting create a clean, modern feel throughout the main living spaces. The kitchen features new appliances installed approximately one year ago, while the master bathroom and electric heat pump were replaced within the last year. Additional updates include new exterior doors, upgraded ceiling fans, and a hall bathroom remodel completed within the last five years. Step outside to enjoy a nice patio space, perfect for outdoor dining, grilling, or relaxing. The private-feeling yard offers room to enjoy the outdoors, while the attached garage and storage shed provide convenient space for parking, hobbies, and storage. With a spacious layout, inviti

Nestled in the Stoney Ridge community, this exquisite split-level residence offers a harmonious blend of modern luxury and timeless comfort. With a major renovation completed in 2015, this home has been updated to provide an upgraded living experience. As you step inside, you are greeted by an inviting atmosphere enhanced by luxury vinyl tile flooring that flows seamlessly throughout the main living areas. The spacious layout features three generously sized bedrooms and three full bathrooms, ensuring ample space for relaxation and privacy. The heart of the home is the beautifully appointed kitchen, equipped with energy-efficient appliances, including a built-in range, microwave, and a sleek cooktop. The upgraded countertops and built-ins create a perfect setting for culinary creativity and entertaining. The bathrooms are thoughtfully designed, showcasing a stall shower and a walk-in shower, providing a spa-like retreat right at home. The presence of cedar closets and walk-in closets ad

Welcome home to 28641 Hope Circle, an elegant 4BR/3.5BA Federal-style residence nestled in the highly sought after Village section of Cookes Hope. Spanning 4,772 sq ft of meticulously maintained living space, this property blends timeless Eastern Shore charm with modern luxury. The thoughtful layout offers unmatched flexibility, featuring dual primary suites with one on the main level and one on the upper level, making it perfect for multi-generational living or an exceptional guest arrangement. The upper primary suite serves as a true sanctuary boasting a luxury bath and a private outdoor deck overlooking the serene surroundings. A welcoming foyer leads to formal dining room (currently being used as a living room) with custom wainscoting, and a private home office/study complete with high-end built-in cabinetry. The heart of the home flows into a sunlit breakfast area, a bright laundry room, and a spacious mudroom with custom coat and shoe organizational shelving. From there, a second

Steps from the local's favorite watering hole, this home is a must-see. Large primary with en suite can also be used as an in-law suite with its own sitting area, or used as two bedrooms. Another nice-sized primary with its own ensuite, and two bedrooms that share a jack-and-jill bathroom, make multi-generational living a piece of cake. Recently renovated to include all new doors, a new deck, new carpet and LVP throughout, new toilets, stove, ceiling fans and fixtures, gutters, and fresh paint throughout, helps make this home turn-key! Oversized detached garage with all new T-11 siding. And for the boating enthusiast, the marina is a short two minute drive away. Steps away from where Hunting Creek meets the Choptank River

Enjoy living in the sought after community of Hyde Park 55+ Adult Living. Located on a corner lot, close to the pool and clubhouse. Amenities also include walking trails, dog park, shuffle board and picnic areas, workout room, boat & Rv storage. This home has new carpet and fresh paint, large living room, dining area and spacious kitchen with breakfast counter. 2 roomy bedrooms and 2 full baths. The dining area opens to a large sunroom and small deck. There is also a shed to house all your garden tools

Enjoy picturesque golf course views toward the clubhouse from the backyard of this beautifully designed two-story villa. Featuring a spacious paver patio and an attached two-car garage, this home offers a thoughtful layout with comfortable main-level living and a first-floor owners suite. The open-concept design seamlessly connects the kitchen, dining area, and expansive Great Room, creating an inviting space for everyday living and entertaining. Upstairs, an open loft overlooking the Great Room provides additional flexible living space, complemented by three secondary bedrooms, including a second owners suite. The versatile floor plan offers options for multi-generational living, hosting guests, working from home, or pursuing hobbies. With elegant finishes, functional living spaces, and scenic golf course views, this home combines comfort, flexibility, and an appealing setting

Welcome home to this spacious 3-bedroom, 2-bath home offering over 2,000 square feet of comfortable living space, situated on a beautiful 1-acre lot! The inviting open floor plan provides a seamless flow between the main living areas, creating the perfect setting for everyday living and entertaining. The desirable split-bedroom floor plan offers added privacy, with the primary suite thoughtfully separated from the additional bedrooms. The spacious living area features a cozy gas fireplace, perfect for those cooler evenings, while the kitchen boasts stainless steel appliances and plenty of space for gathering with family and friends. Step outside and enjoy the wonderful patio area, ideal for outdoor dining, entertaining, or simply relaxing while overlooking the spacious rear yard enclosed with vinyl fencing. The attached 2-car garage provides convenient parking and additional storage space. Recent improvements include an Rinnai water heater for added efficiency and convenience. With ove

To be built! Completion estimated to be in December'2026'. Discover the charm of this brand-new construction ranch-style home, built by'Lomaxx Custom Homes' thoughtfully designed to meet modern living needs. With three spacious bedrooms and two full bathrooms, this beautiful home offers an inviting atmosphere perfect for relaxation and entertaining. The open floor plan seamlessly connects the kitchen, dining and living area, enhanced by recessed lighting and built-ins, creating a warm and welcoming space. The heart of the home is the stunning kitchen, featuring upgraded quartz countertops, a central island perfect for additional seating, and stainless-steel appliances, including a built-in microwave and dishwasher. Sliding rear doors off of the kitchen lead to the beautiful back-yard. The primary suite boasts a luxurious bathroom with a walk-in tiled shower, along with a generous walk-in closet. The hall bathroom is completed with a tiled shower/tub combo. This home is designed with en