Preston Homes for Sale

Preston Homes for Sale

Welcome to Preston, Maryland – a charming town that perfectly balances the tranquility of rural living with the convenience of modern amenities. Nestled in the heart of Caroline County, Preston is known for its picturesque landscapes, friendly community, and rich history. With its roots dating back to the 18th century, this quaint town offers a unique blend of historic charm and contemporary lifestyle.

As you explore Preston, you'll be captivated by its serene surroundings, featuring lush farmland, scenic waterways, and beautiful parks. The town is a haven for outdoor enthusiasts, with ample opportunities for hiking, fishing, and enjoying nature. The close-knit community hosts various events throughout the year, fostering a warm and inviting atmosphere that makes newcomers feel right at home.

For those considering a move to this idyllic town, Preston boasts an array of homes for sale that cater to diverse tastes and lifestyles. Whether you’re looking for a cozy cottage, a spacious family home, or a charming farmhouse, the real estate options here are plentiful. Many properties showcase stunning views and generous lots, perfect for families or anyone seeking a peaceful retreat.

With its affordable housing market and a strong sense of community, Preston is an excellent choice for first-time homebuyers, retirees, or anyone in between. Discover your dream home in Preston today and experience the perfect blend of small-town charm and modern living!

Newest Preston Homes for Sale

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:

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. 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

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

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

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

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:

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

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

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:

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

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

3 Beds ⋅ 3 Baths

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

21245 Tanyard Rd, Preston

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

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