Greensboro Real Estate

Greensboro Real Estate

Welcome to Greensboro, Maryland – a charming small town nestled in the heart of Caroline County. With its picturesque landscapes and friendly community, Greensboro offers a delightful blend of rural charm and modern convenience. This hidden gem is ideally located just a stone's throw away from larger cities, making it the perfect spot for those seeking a peaceful retreat without sacrificing accessibility.

Greensboro boasts a rich history that is woven into its fabric, evident in the well-preserved architecture and local landmarks that tell the story of its past. The town is surrounded by lush farmland and serene waterways, providing ample opportunities for outdoor enthusiasts to explore the natural beauty of the area. Whether you're hiking along scenic trails, fishing in the nearby Choptank River, or simply enjoying a leisurely stroll through one of the town's parks, Greensboro invites you to embrace the great outdoors.

Community spirit thrives in Greensboro, where local events and festivals bring residents together throughout the year. From farmers' markets showcasing the freshest produce to seasonal celebrations that highlight the town's vibrant culture, there's always something happening in this tight-knit community.

Families will appreciate the excellent schools and a safe, welcoming environment that Greensboro provides. With a strong sense of belonging and a slower pace of life, it’s an ideal place for raising children or enjoying a peaceful retirement.

If you're looking for a place that combines the charm of small-town living with the conveniences of modern life, Greensboro, Maryland, may just be your perfect match! Explore the possibilities and discover your new home in this delightful town today.

Newest Listings in Greensboro

$489,000
3 Beds ⋅ 2 Baths
A truly unique property offering multiple dwellings, abundant storage, and exceptional flexibility! The property features multiple residential structures, providing a variety of possibilities for extended family, guests, home offices, hobbies, or additional living space, three separate lots to make a total 7.944 acres. Car enthusiasts, contractors, and hobbyists will appreciate the spacious detached three-car garage, offering plenty of room for vehicles, equipment, tools, and projects. Two additional outbuildings provide even more storage and workspace options. Adding to the property’s versatility is a charming tiny house—ideal for guests, a private retreat, studio, office, or other potential uses. Could also be a Equine facility, room for pastures and rental income. With multiple dwellings, a three-car detached garage, two additional outbuildings, and a tiny house all on one property, this is a rare opportunity for buyers looking for space and flexibility. Whether you envision a multigenerational property, room for hobbies and equipment, or simply want the convenience of multiple structures, this property offers possibilities that are difficult to find.

15078 Drapers Mill Rd, Greensboro

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777
$147,000
Peaceful 5.62 acre wooded lot located on the outskirts of Greensboro. Perc approved for a conventional tile septic system for up to a 4-bedroom home. Discover the perfect blend of natural beauty and rural tranquility on this perc-approved building lot, ready for your dream home. Create your own private nature retreat and enjoy peaceful country living surrounded by nature, all while being within a short drive to nearby towns and conveniences. This property is ready for your vision. Property lines estimated in photos and only four lots in this subdivision selling fast. Some forest conservation area. Discover the perfect blend of nature and accessibility and make your dream home a reality. With a central location convenient to Denton, Easton, Chestertown, central Delaware, and less than an hour to the Bay Bridge.

lot 4 River Rd, Greensboro

Listing courtesy of Taylor Properties. Contact:

$308,990
4 Beds ⋅ 2 Baths
Discover 107 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or spend time together with loved ones. The main bedroom is privately tucked away from the great room and features a walk-in closet and a private, full bathroom. The functional kitchen offers plenty of white cabinet space, stainless steel appliances, a sizeable island with granite countertops and a pantry closet. The fourth bedroom, set apart from the others, is ideal for an office, hobby room, or playroom, with the laundry room conveniently located off the kitchen. The included, white blinds and an innovative Smart Home® package will give you complete peace of mind living in your new home. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

107 Hobbs St, Greensboro

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact: 3017013700
$159,000
2 Beds ⋅ 2 Baths
RARE FIND! Charming, Spacious, Affordable & Move-In Ready! Step into a piece of Greensboro history with this unique second-floor condo located in the original 1922 Greensboro School, thoughtfully converted into 22 individual condo units. This almost 1,000 sq. ft. unit was renovated in 2018 and offers 2 bedrooms and 1.5 baths. An abundance of natural light pours through the impressive oversized, wall-to-wall windows, highlighting the spacious open floor plan, high ceilings, and inviting living spaces. The kitchen and dining area feature a clean, simple design, while the spacious yet cozy living room provides the perfect place to relax and unwind. The sleeping area includes two generously sized bedrooms, with the primary bedroom offering dual closets for plenty of storage. Security and peace of mind are enhanced by an owner keypad and buzzer at the main entrance, multiple building cameras, and a monitored fire suppression/sprinkler system throughout the building. Step outside to enjoy the large, fenced courtyard with picnic tables. Directly beyond the fence is the Town Park, featuring a new basketball court, tennis court, playground, and pavilion. Plus, you’re just a short walk from the river, perfect for fishing, kayaking, or simply enjoying the outdoors. This one-of-a-kind condo offers the perfect blend of history, character, comfort, convenience, and affordability. Opportunities like this don’t come along often, act quickly before this rare find is gone! The condo is currently being freshly painted and new carpet is being installed, providing a bright, refreshed look for its new owner. Select photos have been virtually staged and enhanced. Call me TODAY to schedule your showing! Don’t wait, make your move before someone else does!

107 N School St Unit #2F, Greensboro

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183
$299,000
3 Beds ⋅ 2 Baths
Just a few months old and ready for you to move right in! This beautifully maintained 3-bedroom, 2-bath rancher offers the ease of one-level living with a bright, open layout and the benefits of a nearly brand-new home—without the wait. The spacious kitchen and living areas flow seamlessly together, creating an inviting space for everyday living and entertaining. The seller even added a kitchen island for additional counter space and convenient dining. The large primary suite features a walk-in closet and private en-suite bathroom with a walk-in shower. Additional highlights include a washer and dryer, garage door opener, upgraded blinds package, and smart home package—all already in place for the next owner. The seller’s work is taking them in another direction, creating an opportunity for you to take advantage of this nearly new home. Furniture is also negotiable, making this an easy transition for a buyer looking for a move-in-ready property. Located in Kinnamon Meadows, an up-and-coming community in Greensboro, with convenient access to local amenities and outdoor recreation. Enjoy fishing and kayaking along the Choptank River at nearby parks, as well as tennis and pickleball courts and playgrounds. Greensboro is also home to a brand-new elementary school. With a central location convenient to Denton, Easton, Chestertown, central Delaware, and less than an hour to the Bay Bridge this home offers the perfect combination of modern living, low-maintenance convenience, and an easy commute at a fantastic price!

101 Parkland Rd, Greensboro

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$291,490
3 Beds ⋅ 2 Baths
Discover 113 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms, two bathrooms, and a two-car driveway. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along this hallway, you will also find a coat closet, a hall linen closet, and the laundry room. The well-appointed kitchen features an abundance of modern gray cabinetry, granite countertops, stainless steel appliances, a corner pantry and a peninsula island with additional room for seating. The main bedroom is set apart in the back of the home and features a walk-in closet and full bathroom with a double-bowl vanity. The included white blinds and an innovative Smart Home® package will give you complete peace of mind living in your new home. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

113 Hobbs St, Greensboro

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact: 3017013700
$130,000
Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water is on site and sewer is available. Any interested buyer should perform their own suitable level of due diligence.

707 W Sunset Ave, Greensboro

Listing courtesy of The Land Group. Contact: (410) 934-3478
$269,000
4 Beds ⋅ 2 Baths
This charming cape cod home is waiting for your creative touches! Lots of room on three floors. The main floor boasts a large living room with new vinyl flooring. A separate dining room, large kitchen, full bath and mudroom with washer and dryer. The second floor has four spacious bedrooms and a charming vintage bath with claw foot tub! The basement is a perfect place for crafts, hobbies and plenty of storage. Outside you will find a huge intown lot with a newly built shed the size of a one care garage that makes a perfect workshop. Price to sell! Be sure to schedule your personal tour today!

108 N Academy St N, Greensboro

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

$315,000
4 Beds ⋅ 2 Baths
Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern conveniences. From the moment you arrive, you'll be captivated by the home's classic curb appeal and inviting front porch. Inside, soaring ceilings, oversized rooms, abundant natural light, and rare original heart-of-pine hardwood floors create a warm and welcoming atmosphere. Rich in history and craftsmanship, the home showcases beautiful millwork, original trim, and timeless architectural details rarely found in newer construction. The spacious country kitchen features custom cabinetry, generous counter space, and plenty of room for gathering with family and friends. A bright, sun-filled laundry room adds convenience, while multiple living spaces provide flexibility for entertaining, working from home, hobbies, or everyday living. Thoughtful updates throughout the home offer modern comfort while preserving its historic charm. In 2026, the front living room and full bathroom were beautifully renovated, and new plumbing lines were installed. Additional improvements include energy-efficient mini-split HVAC systems with smart controls, a new furnace (2025), updated electrical service, numerous replacement windows, remodeled bathrooms, built-in cabinetry, a replacement roof, refinished exterior, front porch enhancements, and many other upgrades that reflect exceptional pride of ownership. Step outside to enjoy your own private backyard retreat. A newer 6-foot privacy fence surrounds the outdoor space, where a brick patio, mature landscaping, and towering shade trees create the perfect setting for relaxing, entertaining, gardening, or enjoying a quiet morning coffee. The peaceful backyard offers privacy and plenty of room to enjoy every season. Located in the charming town of Greensboro, this home offers the best of Eastern Shore living. Enjoy a peaceful small-town setting just minutes from the scenic Choptank River, local parks, schools, restaurants, and everyday conveniences. Outdoor enthusiasts will appreciate nearby boating, fishing, kayaking, and recreational opportunities. The Delaware state line is only a short drive away, making tax-free shopping, beaches, dining, and entertainment easily accessible. High-speed internet is available, making remote work or streaming effortless, while the spacious floor plan easily accommodates growing families, multigenerational living, or anyone seeking additional room to spread out. The seamless blend of historic charm, quality craftsmanship, and modern updates creates a home that is both functional and full of character. Homes of this caliber and history rarely become available. Meticulously maintained and thoughtfully updated, this one-of-a-kind property preserves the timeless beauty and craftsmanship of the past while offering the comfort, efficiency, and conveniences today's buyers expect. Whether you're searching for your forever home or a distinctive property with unmatched character, this remarkable residence is ready for its next chapter. Don't miss this rare opportunity to own a beautifully preserved piece of history. Mortgage savings may be available for buyers of this listing.

111 Maple Ave, Greensboro

Listing courtesy of Redfin Corp. Contact: 3016586186
$875,000
This exceptional commercial property, constructed in 2007, presents a prime investment opportunity with significant potential for returns. The 8,000 square foot building features durable metal siding and masonry construction, ensuring longevity and minimal maintenance costs. The property is in excellent condition, allowing for immediate occupancy or leasing without the need for extensive renovations. Strategically designed with ample parking options, including a dedicated parking lot and driveway access, this property is well-suited for various commercial uses. Its modern infrastructure and efficient layout enhance operational efficiency, making it an attractive option for potential tenants. Investors will appreciate the potential for steady cash flow and appreciation in value, driven by the property's prime location and robust construction. This asset is poised to deliver strong returns in a competitive market, making it a prudent addition to any investment portfolio. Explore the possibilities this property offers for long-term financial growth.

13199 Greensboro Rd, Greensboro

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$389,000
4 Beds ⋅ 2 Baths
4 bedroom 2 bath rancher on 3.6 spacious acres on the headwaters of the Choptank.

13790 Drapers Mill Rd, Greensboro

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$69,000
With LAND becoming less and less available, here is your opportunity to own 3 PARCELS in the Town of Greensboro!! At least one of which has a hooked up Water/Sewer account, so INSTANT SAVINGS on no tap fee!! AND WITH THIS NEW PRICE, DON'T HESITATE -- GREAT PRICE & GREAT OPPORTUNITY! Parcels are believed to total approximately 0.74 Acres, more or less. Abandoned dwelling exists in the center of the parcels, in need of tear down or possible major renovation. Town of Greensboro building codes and ordinances are online their website. Enter dwelling at your own risk. Potential here for 1-2 building sites, or at a minimum rebuild/renovate existing dwelling site. All information deemed reliable but Buyer to perform their due diligence with your plans. Parcels are in Critical Area IDA zone. Being sold strictly AS-IS.

Mill & Lincoln St, Greensboro

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

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