Preston Homes for Sale

Preston Homes for Sale

Welcome to Preston, Maryland – a hidden gem nestled in the heart of Caroline County. This charming town offers a delightful blend of small-town charm and modern amenities, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle. With its picturesque landscapes and friendly community, Preston invites you to experience the warmth of rural living just a stone's throw from larger urban centers.

Preston's rich history is reflected in its quaint streets and historic buildings, providing a unique backdrop for your daily life. Enjoy leisurely strolls along tree-lined avenues, or explore the nearby parks and waterways that showcase the natural beauty of the Eastern Shore. The town is known for its vibrant community spirit, with local events and farmers' markets that bring residents together, fostering connections and creating lasting memories.

For those considering a move, Preston offers an array of homes for sale that cater to diverse tastes and budgets. From charming single-family homes with spacious yards to modern townhouses, there’s something for everyone. Many properties boast beautiful views and easy access to outdoor activities, perfect for those who enjoy fishing, hiking, or simply soaking in the serene surroundings.

With a strong sense of community, excellent schools, and a convenient location that provides easy access to major highways, Preston is more than just a place to live – it's a place to thrive. Discover your dream home in Preston today, and embrace a lifestyle that balances comfort, community, and the beauty of nature. Your new beginning awaits!

Newest Preston Homes for Sale

$200,000
2 Beds ⋅ 1 Baths
Discover a hidden gem in this charming 2-bedroom, 1-bathroom ranch-style home, built in 1950 and brimming with potential. Nestled on a generous 0.48-acre lot, this property offers ample space for expansion or outdoor enjoyment, making it an ideal investment opportunity for those looking to enhance their portfolio. The detached structure, constructed with durable block materials, presents a solid foundation for your vision. While the home is currently in below-average condition, this offers a unique chance for savvy investors to renovate and increase its value significantly. With a little creativity and effort, you can transform this space into a cozy retreat or a lucrative rental property. The expansive driveway accommodates up to six vehicles, providing convenience for tenants or guests. Located in a peaceful neighborhood, this property is poised for appreciation, especially as the demand for rental homes continues to rise. With the right updates, you can create a warm and inviting atmosphere that appeals to a broad range of tenants, ensuring a steady stream of rental income. Seize this opportunity to invest in a property with great potential and make it your own. The possibilities are endless-turn this house into a home that generates returns for years to come!

6132 Harmony Rd, Preston

Listing courtesy of Exit Community Realty. Contact:

$295,000
3 Beds ⋅ 2 Baths
Welcome home to this charming 3-bedroom, 2-bath rancher offering the perfect blend of comfort and convenience. Nestled on a quiet street within the city limits, this property provides a peaceful, country-like setting while remaining just minutes from Easton, Denton, Federalsburg, and Cambridge. Step inside to find luxury vinyl plank flooring throughout the main living areas, with cozy carpeted bedrooms creating a warm and inviting retreat. New flooring has been installed in the hall bathroom as well as a new washer and dryer! The spacious primary suite features a private bath complete with a walk-in shower for added comfort. Outside, you'll appreciate the generous back yard and large storage shed, already equipped with electricity, providing ample space amd function for tools, lawn equipment, hobbies, or additional storage. Whether you're looking for your first home, downsizing, or simply seeking low-maintenance one-level living in a tranquil setting, this property offers the best of both worlds—small-town convenience with a rural feel. Don't miss your opportunity to make this inviting rancher your next home!

212 Apple Ln, Preston

Listing courtesy of Keller Williams Realty. Contact: 3028467839
$285,000
3 Beds ⋅ 2 Baths
Welcome home to this beautifully remodeled 3-bedroom, 2-bath home situated on nearly a half-acre lot in the charming town of Preston. This move-in ready property features beautiful hardwood floors, a spacious kitchen with abundant cabinetry, granite countertops, new appliances, and new carpet throughout. The inviting living room showcases gleaming hardwood floors and a cozy gas fireplace, creating the perfect space for relaxing or entertaining. Enjoy peaceful mornings or quiet evenings on the welcoming front porch while sipping your favorite beverage. For added peace of mind and year-round comfort, the home is equipped with a Generac whole-house generator, ensuring reliable power when you need it most. Don't miss the opportunity to own this beautifully updated home with plenty of space both inside and out!

103 Williamson St, Preston

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265
$425,000
3 Beds ⋅ 2 Baths
Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

21370 Skeleton Creek Rd, Preston

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$299,000
3 Beds ⋅ 2 Baths
Welcome to 113 Chamber Street in the heart of Preston! This well-maintained single-story home offers comfortable living on a spacious 0.42-acre lot within town limits. Featuring 2 full bathrooms, a practical floor plan, and a large detached garage with approximately 880 square feet of space, this property provides plenty of room for parking, storage, hobbies, or a workshop. Enjoy outdoor living with a rear deck overlooking the generous yard, perfect for entertaining, gardening, or simply relaxing. Conveniently located near local schools, parks, shopping, and dining, this home offers small-town charm with easy access to surrounding areas. Don't miss this opportunity to own a move-in-ready property in a desirable Preston location. Schedule your private showing today!

113 Chamber St, Preston

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$260,000
3 Beds ⋅ 2 Baths
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 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. The generator just had it's annual service completed. New carpet was just put in upstairs.

158 Wright St, Preston

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$287,000
3 Beds ⋅ 2 Baths
Welcome to this charming and spacious home in Preston offering 3 bedrooms, 1.5 bathrooms, and 2,050 square feet of comfortable living space. Freshly painted throughout, this home features beautiful hardwood flooring that adds warmth and timeless character. With generous living areas and a move-in-ready feel, this property blends comfort and style while providing plenty of space for everyday living and entertaining. Conveniently located and ready for its next owner to make it their own.

106 Main Street, Preston

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$769,000
3 Beds ⋅ 3 Baths
**Don't Miss This Rare Opportunity** Pride of ownership shines throughout this beautifully appointed home, featuring 3 bedrooms, a bonus room, 3 full bathrooms, a dedicated office space and much more- set on over 4 serene acres. This property includes approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new roof, siding and 10 Velux skylights, along with a new Bosch heat pump installed in 2024. This one-of-a-kind retreat is located just 10 minutes from Easton and only 2 miles from the Choptank Marina for easy boat access. Expanded in a major 2006 renovation which nearly doubled the living space, this bright and airy home is the definition of open-concept. It is clearly designed for both comfortable everyday living and effortless entertaining. At the heart of the home is the stunning 20' x 27' kitchen, complete with rich cherry cabinetry, quartz countertops and stainless steel appliances. The 12’ island makes preparing food a seamless experience while entertaining guests. A cozy wood-burning brick fireplace, featuring an efficient Jotul insert, adds warmth and character, creating the perfect gathering space for family and friends. An oversized walk-in pantry with white cabinetry and an additional sink provides even more counter space. The pantry is already wired for an additional oven and refrigerator, should you desire them. Flowing right off of the kitchen, the show-stopping, expansive 25' x 25' living room impresses with soaring cathedral ceilings, abundant natural light, and 6 brand-new skylights with built-in remote-controlled solar shades. A beautiful stone fireplace with gas logs anchors this inviting room, and creates an atmosphere ideal for relaxing or entertaining year-round. The 11 windows and 3 paneled glass doors allow expansive views of nature to flow into this breathtaking room. Along with the large kitchen and living room, this home offers a sunny 10’ x 20’ room which has previously been used as both a family room and a home office. With two spacious master suites on separate ends of the home, an additional bedroom, a bonus room, three full bathrooms, a dedicated mud-room, large pantry, and office, this layout truly offers incredible flexibility for multigenerational living, multiple guests, or work-from-home needs. When you are ready to step outside and enjoy the peaceful tranquility of this property, you will love the expansive deck overlooking the beautiful and secluded backyard. There is ample space for a large garden, or for any of your desired outdoor activities. Nature lovers will appreciate the property’s reputation as a bird lover’s paradise with 98 documented bird species seen on the property throughout the last 3 years. The numerous nesting boxes and feeders throughout the grounds, and even a deer stand for hunting enthusiasts, will convey. Your dogs will also enjoy roaming the property safely, as this property includes approximately 1.5 acres of invisible dog fencing. The two large pole barns, (30’x40’x10’ and 30’x40’x14’) which also received new roofs and skylights in 2025, can easily store multiple vehicles and large equipment. Besides vehicle storage, the spacious pole barns could easily be used to house your dream home gym, workshop and or hobby space! This exceptional property offers the rare combination of modern updates, natural beauty, functional open-concept space, and unmatched privacy—all meticulously maintained and ready for its next proud owner.

3547 Prchal Rd, Preston

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000
$219,900
3 Beds ⋅ 2 Baths
Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP) flooring, offering a clean and low-maintenance foundation for the space. Enjoy outdoor living from both the covered front porch and the rear porch, providing comfortable areas to relax or entertain. With its central location and existing rental history, this property presents a strong investment opportunity or a chance to make it your own.

156 Main St, Preston

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$399,000
3 Beds ⋅ 2 Baths
This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance.. Convenient mudroom off garage with washer and dryer; going on into the kitchen with the pantry next to mudroom for convenience. Full-size attic with flooring providing lots of storage area. Large 24' deep x 23' wide two-car garage with overhead door and remote controls complete with shelving for storage. Two large sheds (insulated and electric) for many uses including a craft shop, carving shop, etc.; one is complete with a pellet stove for cool/cold days or evenings. All of this and more comes with privacy and deeded rights to the dock/pier at the end of the lane. Perfect to just relax and enjoy the water or to crab/fish. Some types of "farm animals" are allowed as long as they do not go off the property onto some other property (refer to docs). All this comes with 3.23 private acres of "home" written all over. Schedule your appointment today!

7392 Todds Wharf Rd, Preston

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$334,900
4 Beds ⋅ 2 Baths
Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing! Easton or Delaware only 15 Minutes! One Hour to Ocean City and Delaware Beaches.

147 Mill Street, Preston

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$224,000
3 Beds ⋅ 2 Baths
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.

126 Maple Avenue, Preston

Listing courtesy of Marshy Hope Realty LLC. Contact: 410-754-7000
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