Preston Homes under $500,000

Preston Homes under $500,000

**Discover the Charm of Preston, Maryland**

Nestled in the heart of Caroline County, Preston, Maryland, is a hidden gem that perfectly blends small-town charm with modern conveniences. This quaint town, with a population of just over 600 residents, boasts a warm and welcoming atmosphere, making it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life. Surrounded by picturesque landscapes, Preston is known for its rich history and vibrant community spirit.

One of the most appealing aspects of Preston is its affordability. For those seeking to purchase a home without breaking the bank, you’ll find a variety of delightful options under $500,000. From charming single-family homes with spacious yards to cozy bungalows perfect for first-time buyers, there’s something for everyone in this lovely town. The real estate market here offers not just affordability but also the opportunity to invest in a community that values connection and quality of life.

Residents enjoy easy access to outdoor activities, with nearby parks and waterways perfect for fishing, hiking, and family picnics. The town's close-knit community often hosts events that bring neighbors together, fostering a sense of belonging that is hard to find in larger cities.

Whether you’re drawn to the serene countryside or the friendly faces of Preston, this town is more than just a place to live; it’s a place to call home. Explore the available homes under $500,000 and discover the perfect spot to start your next chapter in this charming Maryland town!

Newest Preston Homes under $500,000

315 Hughlett St, Preston
$399,000
5 Beds ⋅ 4 Baths
Coming Soon! More Photos Coming Soon! Take advantage of this wonderful opportunity to own a spacious, beautifully updated home in Tidewater Farms! The sellers are downsizing, creating an exciting opportunity for the next owner to enjoy all this home has to offer. Welcome to this spacious 5-bedroom, 3.5-bath home in Tidewater Farms, offering a versatile layout with room for everyone! Featuring two en-suite bedrooms—one conveniently located on the main level and another on the second floor—this home offers flexibility for a variety of living arrangements. Enjoy peace of mind with a **new roof installed 2025 and HVAC system installed in 2024**. Thoughtful updates throughout include additional cabinetry in the dining room, updated lighting and/or ceiling fans in every room, and dusk-to-dawn exterior lighting for added convenience. Step outside to enjoy the fenced-in backyard, complete with an above-ground pool and deck—perfect for relaxing, entertaining, and making the most of the warmer months. The pool also features a separate electrical service. With five bedrooms, multiple en-suite options, important recent updates, and inviting outdoor amenities, this Tidewater Farms home offers space, comfort, and functionality.

315 Hughlett St, Preston

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

22067 Dover Bridge Rd, Preston
$99,000
3 Beds ⋅ 1 Baths
Investment Opportunity in a Prime Eastern Shore Location! Located at 22067 Dover Bridge Road, this 3-bedroom, 1-bathroom home sits on a spacious half-acre lot in a convenient location central to Easton, Preston, and Denton. Being sold as-is, this property offers an opportunity for investors, contractors, or buyers ready to bring their vision and creativity to the table.

22067 Dover Bridge Rd, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

21269 Dover Bridge Rd Unit LOT 15, Preston
$55,000
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.Motivated seller.Being sold AS-IS

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
🏡 BRAND-NEW CONSTRUCTION | MOVE-IN READY | MODERN COMFORT! Your next chapter starts at 155 Wright St, Preston, MD 21655! This beautifully completed 3-bedroom, 2-bath home offers approximately 1,626 square feet of thoughtfully designed living space, combining modern finishes with a bright, open-concept layout. Step inside and discover a spacious kitchen and living area designed for everyday living and entertaining. The kitchen features stylish 42-inch cabinetry, under-cabinet lighting, quartz countertops, and a generous island that creates a natural gathering space. Luxury vinyl plank floors paired with recessed lighting add a clean, contemporary feel throughout the home. Enjoy the comfort of a tankless water heater, an encapsulated crawl space, and an attached 2-car garage. Outside, a large in-town lot offers room to enjoy the outdoors, while the 12' x 16' deck provides an inviting space for relaxing or entertaining. Conveniently located near local parks and schools, this newly built home offers the benefits of modern construction with the convenience of an in-town setting. Why wait to build when your new home is ready for you? If you're ready to explore homeownership, ask about financing options and potential down payment or closing cost assistance programs for which you may qualify. 📍 155 Wright St, Preston, MD 21655 Schedule your private showing and come see the possibilities for yourself

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
$289,000
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:

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