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

$574,900
4 Beds ⋅ 3 Baths
Beautifully Maintained Home with Private In-Law Suite, Pool & Exceptional Workshop Space This well-maintained property offers outstanding flexibility with a spacious private in-law suite connected to the main home by a bright sunroom with direct access to the deck and backyard. Perfect for multi-generational living, guests, or potential rental income. The main home features an updated kitchen with maple cabinetry, granite countertops, pantry, hardwood flooring, recessed lighting, and premium Jenn-Air, Viking, and LG Café stainless steel appliances. The living room showcases a stone wood-burning fireplace and opens to the dining area. The primary suite includes an updated walk-in shower, while two additional bedrooms and a bonus room provide flexible living space. A full-length composite front porch adds charm and curb appeal. The sunroom, with slate flooring and abundant natural light, leads to the deck, hot tub, and fully fenced backyard. Outdoor amenities include a saltwater in-ground pool and screened pool house with a ceiling fan and changing room, creating an ideal setting for entertaining and relaxation. The private in-law suite offers a living room, eat-in kitchen, spacious bedroom with ensuite bath, half bath, dedicated laundry room, and attached one-car garage with handicap-accessible ramp. Additional features include ceiling fans throughout the home, suite, workshop, and screened porch; a stone driveway with ample parking; a 12' x 20' shed; a 12' x 30' workshop with electric; an 18' x 30' RV/boat carport; and an insulated 24' x 30' garage/workshop with electricity, gas heat, built-in shelving, and custom workbench. Recent improvements include new concrete patios, walkways, and fire pit (2026), upgraded septic system, encapsulated crawl space with dehumidifiers, encapsulated attic, LeafFilter gutter protection, and a new hot water heater in the in-law suite (2026). The beautifully landscaped grounds feature excellent drainage, established gardens, and a secluded sitting area to enjoy nature and local wildlife. Surrounded by Lynch Preserve, the community offers miles of scenic walking trails. Combining comfortable living, versatile space, and resort-style outdoor amenities, this unique property truly has something for everyone. Within minutes to Neighborhood Ramp for all your boatig and fishing needs on the Choptank River. Less than 1 hour to the Bay Bridge. Easy commute to Easton, Delaware or Salisbury. Schedule your private tour today.

24308 Marlyn Dr, Preston

Listing courtesy of Brenton Realty Group. Contact: 4104794663
$389,900
3 Beds ⋅ 2 Baths
Welcome to 155A Wright St, Preston, MD 21655! 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. With modern finishes and thoughtful details throughout, this home is move-in ready and waiting for its new owner. Schedule your private showing today!

155A Wright St, Preston

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

$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: 4105434545
$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:

$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
$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:

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