Preston Homes for Sale

Preston Homes for Sale

Welcome to Preston, Maryland—a charming town nestled in the heart of Caroline County. Known for its picturesque landscapes and a close-knit community, Preston offers a unique blend of rural charm and modern convenience. With a population that values both tradition and growth, this quaint town is perfect for those seeking a peaceful lifestyle while still having access to nearby amenities.

As you explore Preston, you'll find a variety of homes for sale that cater to diverse tastes and budgets. From cozy single-family residences to expansive properties with ample land, there’s something for everyone. Many homes feature classic architectural styles, with inviting front porches and lush gardens that reflect the town's serene ambiance. The real estate market here is thriving, making it an ideal time to invest in a property that not only serves as a home but also as a gateway to a vibrant community.

Preston is conveniently located near major highways, providing easy access to larger towns and cities, yet it retains its small-town allure. Residents enjoy a range of outdoor activities, from hiking and biking along scenic trails to fishing in nearby rivers. The local schools are well-regarded, making Preston an attractive option for families.

In summary, Preston, MD is a hidden gem that promises a peaceful lifestyle, a welcoming community, and a variety of homes for sale. Come discover your dream home in this beautiful town, where you can relish the tranquility of country living without sacrificing modern conveniences.

Newest Preston Homes for Sale

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:

155 Wright St, Preston
$379,900
3 Beds ⋅ 2 Baths
🏡 BRAND-NEW CONSTRUCTION ****BUYER INCENTIVE!!*** Seller is offering up to $5,000 toward buyer's eligible closing cost, prepaid expenses, or discount points, subject to lender approval and negotiated contract terms, Ask about this great opportunity!! 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
$369,900
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
$319,900
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:

7737 Westerly Dr, Preston
$555,900
3 Beds ⋅ 3 Baths
*Major Price Improvement* **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, fruit trees, 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:

304 Tidewater Cir, Preston
$384,499
6 Beds ⋅ 3 Baths
$20K PRICE DROP!! MOTIVATED SELLER! Looking to close FAST! Priced to move, come and claim this 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:

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:

212 Apple Ln, Preston
$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:

21370 Skeleton Creek Rd, Preston
$399,000
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:

156 Main St, Preston
$179,900
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:

126 Maple Ave, Preston
$215,000
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 Ave, Preston

Listing courtesy of Marshy Hope Realty LLC. Contact:

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