Greensboro Real Estate

Greensboro Real Estate

Welcome to Greensboro, Maryland – a charming gem nestled in the heart of Caroline County. This picturesque town, known for its small-town allure and rich history, offers a unique blend of rural tranquility and community spirit. With a population that embraces the close-knit atmosphere, Greensboro is the perfect place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Greensboro is conveniently located along the banks of the Choptank River, providing residents with stunning natural beauty and a wealth of outdoor activities. The surrounding landscapes are adorned with lush greenery and scenic views, making it an ideal spot for nature enthusiasts. Residents can enjoy fishing, kayaking, and hiking in nearby parks, ensuring that there’s always an adventure waiting just outside their doorstep.

The town boasts a vibrant community with local shops, cozy cafés, and family-owned restaurants that reflect the warmth of its residents. The annual events and festivals foster a sense of belonging, bringing neighbors together to celebrate the town's rich heritage and culture.

Education is a priority in Greensboro, with access to quality schools that focus on fostering a nurturing environment for children. The town also offers easy access to larger cities, making it a perfect blend of peaceful living with the conveniences of urban life.

Whether you're looking to settle down or invest in a vacation home, Greensboro, MD, is a delightful choice that offers a welcoming community, beautiful surroundings, and a pace of life that allows you to truly savor every moment. Come explore Greensboro – you might just find your perfect place to call home!

Newest Listings in Greensboro

311 N Academy St, Greensboro
$364,900
3 Beds ⋅ 2 Baths
Built in 2022, this 3-bedroom, 2-bath home offers modern, easy one-level living with thoughtful upgrades throughout. The open living space features granite countertops, Samsung stainless steel appliances, an electric fireplace, and no carpet throughout the home. The kitchen provides a large walk-in pantry, while the spacious primary suite includes a walk-in closet, wireless speaker in the bathroom, and plenty of room to unwind. Additional conveniences include a front-load washer and dryer with pedestals, Ecobee smart thermostat, wireless garage door opener, and an attached 2-car garage with added cabinetry. Outside, enjoy a paved driveway and fenced backyard offering space for pets, entertaining, or relaxing outdoors. With a newer 2022 build and a move-in-ready interior, this Greensboro home is ready for its next owner. Additional Pictures coming soon.

311 N Academy St, Greensboro

Listing courtesy of EXP Realty, LLC. Contact:

111 Maple Ave, Greensboro
$299,900
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:

S Quail Court, Greensboro
$434,500
3 Beds ⋅ 2 Baths
Welcome to S Quail Ct in Greensboro! The model home is located across the street and can be toured 13926 S Quail Ct. This to-be-built home offers just over 1,800 square feet of thoughtfully designed living space on more than an acre, backing to mature trees for added privacy. Tucked away on a dead-end street with no through traffic, the setting offers plenty of space and privacy while still providing the convenience of a beautiful new home. From the moment you arrive, you'll notice the attention to detail, including an inviting covered front porch, large driveway, oversized two-car garage, and exterior soffit lighting surrounding the home for an impressive look after dark. Step inside to a bright, open floor plan filled with upgraded finishes. The spacious kitchen is designed to be the heart of the home and features a large center island, stainless steel appliances, upgraded lighting, and plenty of room for gathering and entertaining. Pella windows and doors, high-end LVP flooring, recessed lighting throughout, upgraded trim, and carefully selected fixtures give the home a clean, custom feel. The bathrooms continue the upgraded finishes with stylish vanities and tile, including a beautiful walk-in shower. Ceiling fans are installed in all bedrooms, and the separate laundry room includes both a utility sink and washer and dryer. Out back, enjoy the low-maintenance deck overlooking the spacious yard and mature trees — a great setting for relaxing, grilling, or entertaining. The oversized two-car garage is fully finished and painted with plenty of lighting, making it as functional as it is clean. With over an acre of land, more than 1,800 square feet of living space, quality finishes throughout, an oversized finished garage, private backyard setting, and a 2-year home warranty, this new construction home offers much more than just "brand new." Come see the craftsmanship, upgrades, and attention to detail for yourself!

S Quail Court, Greensboro

Listing courtesy of CR Realty. Contact:

13740 Greensboro Rd, Greensboro
$360,000
Location, Location, Location! Exceptional visibility and high traffic exposure on Rt. 313 make this an excellent commercial opportunity. Zoned HC (Highway Commercial), this property offers a wide variety of potential uses and endless possibilities for investors, entrepreneurs, and business owners. Formerly a car wash and later a boat, watercraft, and ATV repair shop, the site is ready to be revitalized or transformed into your next venture. The property features a private well with a new well pump, one bay equipped with heat, and the option to connect to town water and sewer utilities. Boasting dual road frontage on Greensboro Rd and Main St, this highly visible location is strategically situated between Quick Stop Gas Station and Dollar General, and located near schools, residential communities, and the fire department/community center. Whether you're considering a car wash, automotive business, contractor storage, self-storage facility, or another commercial use, this property offers tremendous potential in a growing, high-traffic location, Bring your vision to life!! Buyer to perform their own due diligence regarding zoning, permitted uses, and development possibilities. Be sure to explore the virtual concept showcasing a car wash, automotive shop, and storage facility to help envision the property's potential. These illustrative concepts highlight just a few of the many possibilities this Highway Commercial-zoned property may offer. Note: Images shown are conceptual renderings and are for illustrative purposes only. They depict potential future uses and/or redevelopment possibilities and do not represent the property's current condition, improvements, or any approved plans. Call today for more information or to schedule your private tour!

13740 Greensboro Rd, Greensboro

Listing courtesy of Clark & Co Realty, LLC. Contact:

320 N Main St, Greensboro
$389,900
3 Beds ⋅ 2 Baths
Welcome to 320 N Main St in the charming town of Greensboro! Step inside and discover a home that immediately invites you to kick off your shoes and stay awhile. Situated on a spacious half-acre lot, this 3-bedroom, 2.5-bath home offers the perfect blend of comfort, functionality, and style. The beautifully updated kitchen is sure to impress, featuring a five-burner gas range, stainless steel appliances, farmhouse sink, and granite countertops. The kitchen opens seamlessly to the dining area and spacious living room, creating a wonderful flow for everyday living and entertaining. Upstairs, you'll find the home's private sleeping quarters. The primary suite features an en-suite bathroom and access to a private deck overlooking the backyard. Two additional generously sized bedrooms share a guest bathroom. Step outside and discover your own private oasis! The backyard features an above-ground saltwater pool (being sold as-is and in need of a liner), a triple-tiered deck, and an abundance of mature plants and flowers. Whether you're grilling, entertaining, relaxing by the pool, or simply enjoying the sunshine, this outdoor space makes every day feel like a getaway. The property offers three garage bays, including an attached two-car garage and a detached two-car garage. The detached garage is heated by propane, making it an ideal workshop or hobby space year-round. A separate greenhouse with pellet-stove heat provides the perfect setting for gardening enthusiasts. A paved driveway provides plenty of parking for family and guests. Other improvements include - roof approx 10 years old, a main level HVAC system 1 year old and a compressor installed on the second floor HVAC system and water heater 5 years old. Conveniently located approximately 35 minutes from the Bay Bridge, with easy access to Denton for dining and shopping and Delaware for tax-free shopping. This one truly needs to be seen to be appreciated! Schedule your private tour today! Note: Select photos have been virtually enhanced and/or staged for illustrative purposes only and may not reflect the property’s current condition.

320 N Main St, Greensboro

Listing courtesy of Clark & Co Realty, LLC. Contact:

25722 Old Mill Ln, Greensboro
$649,997
4 Beds ⋅ 4 Baths
Spacious, versatile, and made for both everyday living and entertaining, this 4-bedroom, 4.5-bath home offers an incredible amount of space inside and out. The heart of the home is the stunning kitchen, which opens to a large dining area and generous living space, creating an easy flow for gatherings of any size. Each bedroom is spacious and thoughtfully positioned, while the primary suite stands out with a beautiful private bath and large custom walk-in closet. Outside is where this property really shines. With plenty of land to enjoy, there’s room to entertain, relax, take on new projects, or simply spread out. Spend summer days by the in-ground pool, create your own hot tub retreat with dedicated space and electric already available, or take advantage of the former animal coop, previously used for pigs and chickens. The oversized garage provides even more flexibility for cars, hobbies, a workshop, equipment, or all the toys that come with having room to enjoy them. With a great layout, expansive outdoor space, and so many ways to make the property your own, this home offers a rare combination of comfort, functionality, and opportunity.

25722 Old Mill Ln, Greensboro

Listing courtesy of Allfirst Realty, Inc.. Contact:

15078 Drapers Mill Rd, 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:

lot 4 River, Greensboro
$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, Greensboro

Listing courtesy of Taylor Properties. Contact:

101 Parkland Rd, Greensboro
$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:

707 W Sunset Ave, Greensboro
$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:

108 N Academy St N, Greensboro
$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:

13199 Greensboro Rd, Greensboro
$649,000
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:

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