Preston Real Estate

Preston Real Estate

Welcome to Preston, Maryland—a hidden gem nestled in the heart of Caroline County. This charming town offers a perfect blend of small-town warmth and rich history, making it an ideal place to call home. With a population of just over 600 residents, Preston exudes a tight-knit community vibe that welcomes newcomers with open arms.

As you stroll through the picturesque streets of Preston, you’ll be captivated by its quaint architecture and lush landscapes. The town is surrounded by rolling farmland, providing a serene backdrop for outdoor enthusiasts and nature lovers alike. Whether you’re taking a leisurely walk, biking along scenic routes, or enjoying a picnic in one of the local parks, Preston offers plenty of opportunities to embrace the great outdoors.

Preston is not just about natural beauty; it also boasts a rich cultural heritage. The town's history is reflected in its well-preserved buildings and local landmarks, which tell the story of its founding and growth over the years. The community hosts various events throughout the year, fostering a sense of togetherness and celebration among residents.

Conveniently located near major highways, Preston offers easy access to nearby towns and cities, ensuring that residents can enjoy the tranquility of rural living while still being close to urban amenities. With its affordable housing options and low cost of living, Preston is an attractive choice for families, retirees, and anyone looking for a peaceful lifestyle.

Discover the charm of Preston, Maryland—a place where community spirit thrives and every day feels like a breath of fresh air. Come explore what makes this delightful town a wonderful place to live!

Newest Listings in Preston

$225,000
2 Beds ⋅ 1 Baths
Charming and full of potential, this 2-bedroom, 1-bath home offers an excellent opportunity in Preston! Set on approximately 0.55 acres, this 891-square-foot single-level home features a spacious deck and a practical layout ready for its next chapter. Whether you're searching for an affordable primary residence, a weekend getaway, or an investment opportunity, this property is worth a look. Enjoy the space and privacy of an unincorporated setting while being conveniently located in the Preston area. Don't miss the opportunity to make 6149 Bethlehem Road your own!

6149 Bethlehem Rd, Preston

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$319,000
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: 3023600300
$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: 4108226665
$385,000
4 Beds ⋅ 2 Baths
Space, flexibility and over an acre to call your own — welcome to 5716 Bethlehem Road! Set on 1.14 acres in Preston, this spacious one-level home offers 4 bedrooms, 2 full bathrooms, a separate den/flex room and a floor plan with room to spread out. Step inside and you'll find bright, generously sized living spaces and plenty of possibilities. The owner's suite is tucked away with its own private full bath and walk-in closet, while three additional bedrooms provide space for everyone. Need an office, hobby room, playroom or extra hangout space? The additional den gives you even more flexibility. The spacious kitchen offers plenty of cabinetry and counter space, select updated appliances and easy access to the rear deck — perfect for taking dinner outside, firing up the grill or simply enjoying the view of your own backyard. And what a backyard it is! With 1.14 acres, expansive lawn, mature trees and plenty of room to enjoy the outdoors, this property gives you space that's becoming harder and harder to find. There's even a storage shed, generous gravel parking and turnaround area, plus attic storage for all the extras. Built in 2001 and offering the convenience of one-level living, four true bedrooms, a private owner's suite and more than an acre of land, this Preston home has the space both inside and out. Come take a look — you may be surprised by just how much this home has to offer!

5716 Bethlehem Rd, Preston

Listing courtesy of NextHome Envision. Contact: 3018816398
$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: 3023600300
$649,900
3 Beds ⋅ 3 Baths
**Thoughtfully Renovated & Move-In Ready** Welcome to a beautifully renovated home offering 3 bedrooms plus a flexible bonus space with potential for a 4th bedroom in the water front community of Two Johns. Extensively updated from top to bottom, this home offers a fresh, modern feel while maintaining a warm and inviting atmosphere. As you enter, you’ll immediately notice the all-new flooring and lighting throughout, freshly painted rooms, new interior doors, and crown molding featured in most spaces, creating a clean and cohesive look throughout the home. The updated kitchen combines style and functionality with beautiful quartz countertops and stainless steel appliances, making it the perfect space for everyday living and entertaining. All three bathrooms have been thoughtfully updated, including a beautifully redesigned and custom-appointed primary suite bathroom. Step outside and enjoy the best of outdoor living from the spacious screened-in porch overlooking the private rear yard. The backyard retreat features an inviting in-ground pool and a 1,000-gallon pond with a tranquil waterfall, creating a peaceful setting for relaxing, entertaining, and enjoying your own private oasis. The exterior has received an impressive facelift as well, featuring brand-new siding, Azek window trim, new exterior doors, and new exterior lighting, giving the home a fresh and welcoming appearance from the moment you arrive. The spacious two-car garage offers even more versatility with a full bonus room on the second floor, complete with heat and A/C on both levels—perfect for a home office, gym, entertainment space, guest area, or potential additional living space. A lean-to extends off the back of the garage, providing even more room for storage, hobbies, equipment, or outdoor necessities. With extensive updates throughout and incredible indoor and outdoor living spaces, this home is move-in ready and waiting for its new owners!

7737 Westerly Dr, Preston

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000
$235,000
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: 3023600300
$414,499
6 Beds ⋅ 3 Baths
LOVELY Tidewater Farms home with a light, open layout and plenty of space to enjoy. The main level features a spacious breakfast room, open kitchen and great room with a center island, eat-at bar, and gas fireplace. There is also a 19' x 15' bonus room and convenient upstairs laundry. The primary suite offers walk-in closets, a soaking tub, separate shower, and double sink vanity. Outside, enjoy the patio, storage shed, and white panel fence. The home has a brand-new roof from last year, HVAC upgraded approximately five years ago, brand-new washer and dryer, good plumbing, and a finished crawl space. Appliances are under warranty. The sellers are in the process of transitioning into their new home, so buyers should plan for a few months before possession. Reach out for additional information and pictures of the property!

304 Tidewater Cir, Preston

Listing courtesy of Samson Properties. Contact: 3018500255
$102,500
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:

$175,000
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
Seller is offering a $4,500 credit for new carpet in all 3 bedrooms! 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
$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
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