Preston Homes under $400,000

Preston Homes under $400,000

Welcome to Preston, Maryland—a charming town nestled in the heart of Caroline County. Known for its picturesque landscapes and tight-knit community, Preston offers a unique blend of small-town charm and modern conveniences. With its rich history and welcoming atmosphere, this delightful town is an ideal place for those seeking a peaceful lifestyle without sacrificing access to urban amenities.

Preston is surrounded by the natural beauty of Maryland’s Eastern Shore, making it perfect for outdoor enthusiasts. Residents can enjoy the serene waters of nearby rivers and lakes, as well as the lush greenery that characterizes this region. Whether you're looking to take a leisurely stroll through one of the local parks or embark on an adventurous day of fishing or kayaking, Preston provides ample opportunities to connect with nature.

For homebuyers, Preston is a hidden gem, particularly for those seeking affordable housing options. With a variety of homes available under $400,000, this town offers a range of choices for first-time buyers, families, and retirees alike. From quaint cottages to spacious family homes, you’ll find properties that cater to diverse tastes and needs.

The local community is vibrant, with friendly neighbors and a strong sense of belonging. Preston is also conveniently located near major highways, providing easy access to larger cities for work or leisure. If you’re searching for a place that combines affordability with a warm community spirit, Preston, MD, is the perfect destination to call home. Come explore the possibilities and discover your dream home in this delightful town!

Newest Preston Homes under $400,000

21269 Dover Bridge Rd Unit LOT 15, Preston
$60,000
3 Beds ⋅ 2 Baths
Nestled in Dover Bridge Mobile Home Park—formerly Prettyman Manor.This large double-wide manufactured home offers plenty of space and potential. 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 located between Easton and Preston.

21269 Dover Bridge Rd Unit LOT 15, Preston

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

23554 Jonestown Ln, Preston
$270,000
3 Beds ⋅ 2 Baths
Freshly renovated and move-in ready home on an acre! This 3-bedroom, 2-bath home offers a refreshed interior in a convenient Preston location. The renovation work is already complete, giving the next owner the chance to settle in and make the home their own. If you’re looking for a turnkey home on Maryland’s Eastern Shore, this one is worth a look.

23554 Jonestown Ln, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

155 Wright St, Preston
$379,900
3 Beds ⋅ 2 Baths
PRICE REDUCTION — NOW $379,900! Welcome to 155 Wright St, Preston, MD 21655! NEW PRICE! This newly completed 3-bedroom, 2-bath home is situated on a large, quiet in-town lot conveniently located near parks and schools. Offering approximately 1,626 square feet of comfortable living space, this beautiful home features a conditioned crawl space, 42-inch cabinetry with under-cabinet lighting, quartz countertops, and a tankless water heater. Enjoy modern finishes and thoughtful details throughout this move-in-ready home, designed for comfortable everyday living. With the price now reduced from $389,900 to $379,900, this is a great opportunity to make this beautiful new construction your own! Schedule your private showing today!

155 Wright St, Preston

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

107 Sunset Blvd, Preston
$375,000
3 Beds ⋅ 3 Baths
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, inviting living areas, and numerous updates, 107 Sunset Blvd is a wonderful opportunity to enjoy the comfort of a well-maintained home in a convenient Preston location!

107 Sunset Blvd, Preston

Listing courtesy of Coldwell Banker Realty. Contact:

117 Sunset Blvd, Preston
$329,900
3 Beds ⋅ 3 Baths
Welcome to 117 Sunset, a spacious one-level ranch offering 1,890 square feet, three bedrooms, two and a half baths, and plenty of character inside and out. The standout living area immediately draws your eye with its soaring vaulted wood-plank ceiling, exposed beams, abundant natural light, and impressive full brick fireplace wall, creating a warm gathering space unlike the typical ranch. The kitchen offers generous cabinetry and counter space with an adjoining dining area, while the flexible floor plan provides comfortable everyday living and room to entertain. Three well-proportioned bedrooms include a primary suite with a private bath, and additional baths provide convenience for family and guests. Outside, the 0.53-acre lot gives you room to spread out, garden, entertain, or simply enjoy the open lawn. A patio and garden swing create inviting spaces to relax, while the detached carport and additional storage buildings/sheds provide exceptional space for vehicles, hobbies, lawn equipment, or workshop needs. Built in 1971, this home offers the charm and craftsmanship buyers love, wood details, generous living spaces, established landscaping, and a property with room to make it your own. 117 Sunset is a home with personality, space, and possibilities, both indoors and out.

117 Sunset Blvd, Preston

Listing courtesy of Keller Williams Flagship. Contact:

105 Noble Ave, Preston
$299,000
3 Beds ⋅ 2 Baths
105 Noble Ave is proof that you don't have to sacrifice space to stay within budget! This massive home offers 3 bedrooms, 2 full bathrooms, and an incredibly flexible floor plan to fit your needs. Originally a 4-bedroom 1 bath home, the fourth upstairs bedroom has been converted into two oversized closets. Need another bedroom? The main level features two flex rooms off the dining area that could easily become a first-floor primary suite, home office, playroom, or guest space. Tall ceilings throughout make the home feel even more spacious, while the partial basement and full walk-up attic with high ceilings offer endless potential for storage or future finished living space. Outside, you'll love the large front porch, huge backyard, and hardscape patio—perfect for relaxing or entertaining. Plus, enjoy peace of mind knowing the roof was replaced 8/24/26 and all the major items have been taken care of in the last 5 years including windows and HVAC.

105 Noble Ave, Preston

Listing courtesy of Keller Williams Realty. Contact:

21182 Marsh Creek Road E-10 Rd, Preston
$74,900
3 Beds ⋅ 2 Baths
The home is located in between Easton and Preston, very close to Easton major shopping centers. This home offers 3 bedroom 2 full baths, and a large living room, Very private setting. For an application go to tenantrelationships@rentstackhouse.com, For question call 855-548-3642. You will get an AI recepticent , ask for Cecelia for billing questions and Brandis for application questions

21182 Marsh Creek Road E-10 Rd, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

5716 Bethlehem Rd, Preston
$378,500
4 Beds ⋅ 2 Baths
$378,500! Looking for a little more house, a little more land and a lot more room to enjoy life? Welcome to 5716 Bethlehem Road, where Mid-Shore living comes with 4 bedrooms plus a den, 2 full baths and approximately 1.14 acres to spread out and make your own. Inside, the flexible floor plan gives you plenty of options. The owner’s suite has its own private bath, and the eat-in kitchen is ready for morning coffee, weeknight dinners and those conversations that somehow turn into an hour. Need a home office? Guest room? Hobby space? Workout room? Or maybe just one room where you can close the door and pretend the to-do list doesn’t exist for ten minutes. There’s space for that too. And then there’s the attic space, perfect for storage and all the stuff you don’t necessarily want to look at every day but somehow still aren’t ready to part with. Outside, the house keeps delivering. Start the morning on the front porch, move to the deck when it’s time to relax or entertain, and enjoy the beautiful landscaping that gives the property its character. With more than an acre, there’s room to garden, gather around a firepit, let the dogs run, throw a backyard party or simply enjoy having some space between you and the rest of the world. A shed gives you extra storage for tools, outdoor gear and all the stuff that seems to multiply once you own a little land. And when you’re ready to get out and explore, you won’t have to go far. Fishing, boating and paddling on the Choptank River are just minutes from you, while nearby Tuckahoe State Park offers miles of hiking and biking trails, kayaking, fishing and plenty of ways to spend a day outdoors. Adkins Arboretum and Martinak State Park add even more trails, nature and waterfront recreation to the mix. This is the kind of place where you can trade traffic and tight spaces for more room, more fresh air and more ways to enjoy your weekends, without giving up the everyday spaces that make a house feel like home. More space at home. More ways to play outside. The relaxed pace of Mid-Shore living

5716 Bethlehem Rd, Preston

Listing courtesy of NextHome Envision. Contact:

107 Chamber St, Preston
$299,000
3 Beds ⋅ 3 Baths
This spacious two-story home offers three bedrooms, two-and-a-half bathrooms, and plenty of room to spread out. The main level features a generously sized living room and a large kitchen with ample space for cooking, gathering, and entertaining. Upstairs, you’ll find a spacious primary suite with its own private bathroom, along with two additional bedrooms and a second full bath. Enjoy your morning coffee on the charming front porch, or relax in the backyard surrounded by a six-foot vinyl privacy fence—perfect for pets, playtime, or private outdoor entertaining. Come see everything this inviting home has to offer!

107 Chamber St, Preston

Listing courtesy of Keller Williams Realty. Contact:

158 Wright St, Preston
$225,000
3 Beds ⋅ 2 Baths
Bring your vision and make this spacious Preston home your own! Offering more than 1,800 square feet, this property features three bedrooms, two full bathrooms, and plenty of room to create a home that fits your style. While the interior is ready for updates, the generous floor plan provides a great foundation for renovation and personalization. Located in the Colonel Richardson School District, this home is an exciting opportunity for a buyer who isn’t afraid of a little work and can see the potential beyond the wallpaper. With the right improvements, this could become one seriously charming home!

158 Wright St, Preston

Listing courtesy of Keller Williams Realty. Contact:

4471 Harmony Rd, Preston
$100,000
3 Beds ⋅ 1 Baths
Discover the potential in this ranch-style home situated on a spacious lot in Caroline County. This property is ready for renovation and offers a great opportunity to update and customize to your vision. Major improvements have already been completed, including a newer roof and updated windows, providing a solid starting point for your renovation plans. The home is served by a private well and septic system and offers the charm of country living with convenient access to Preston and surrounding areas. Bring your ideas and restore this property to its full potential.

4471 Harmony Rd, Preston

Listing courtesy of XRealty.NET LLC. Contact:

6132 Harmony Rd, Preston
$150,000
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:

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