Greensboro Homes for Sale

Greensboro Homes for Sale

Welcome to Greensboro, Maryland – a charming town nestled in the heart of Caroline County. Known for its rich history and tight-knit community, Greensboro offers a unique blend of small-town charm and modern conveniences. With a population that embraces the warmth of neighborly connections, this delightful town is perfect for those seeking a peaceful yet vibrant lifestyle.

Greensboro boasts a picturesque landscape filled with lush greenery and scenic views, making it an ideal setting for outdoor enthusiasts. Residents can enjoy leisurely strolls along the Choptank River or explore the beautiful parks that dot the area. The town is also conveniently located near major highways, providing easy access to the bustling cities of Easton and Dover, while still allowing you to retreat to the tranquility of rural living.

When it comes to homes for sale in Greensboro, you’ll find a diverse array of options to suit your needs. From charming historic homes that reflect the town's heritage to modern new builds equipped with the latest amenities, there’s something for everyone. Whether you’re a first-time homebuyer, looking to upgrade, or seeking a peaceful retirement haven, Greensboro's real estate market has you covered.

With a strong sense of community, excellent schools, and a variety of local shops and restaurants, Greensboro is not just a place to live; it’s a place to thrive. Discover your dream home today in this delightful town where history meets opportunity and community spirit flourishes. Your new chapter awaits in Greensboro, Maryland!

Newest Greensboro Homes for Sale

$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 four 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. 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: 410-490-2183
$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
$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
$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:

$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
$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
$309,900
3 Beds ⋅ 2 Baths
Why wait for new construction? Completed in 2025, this custom-built, move-in ready rancher offers 1,436 square feet of thoughtfully designed, single-level living--with no HOA. The bright, open-concept living, dining, and kitchen area features nine-foot ceilings, solid hardwood flooring and recessed LED lighting. The kitchen is finished with granite countertops, all-wood cabinetry, Samsung stainless-steel appliances, a Moen faucet and an instant hot-water system. Propane lines are already in place should the next owner prefer a gas range. The spacious primary suite includes a walk-in closet and private bath with a tiled walk-in shower and granite vanity. Two additional bedrooms, a second full bath, washer & dryer, window treatments, and ceiling fans make this home truly ready for its next owner. Each bedroom is prewired for television and internet service. Quality construction continues behind the scenes with a 200+ amp electrical service, energy-efficient appliances, spray-foam and batt insulation, floored attic storage, and a professionally encapsulated crawlspace with concrete flooring, lighting, dehumidifier, French drains, and sump pump. Outside, enjoy welcoming front and rear porches, a level backyard with privacy fencing, parking for up to six vehicles and convenient hot & cold exterior water connections plus an electric hookup for a camper or RV. This is not a basic builder-grade home -- it is a carefully constructed, nearly new home with upgrades, storage and practical features already in place. Schedule your private showing and see the difference for yourself. Come see this exceptional home today and become the new owner in just a few weeks!

110 N School St, Greensboro

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

$280,000
5 Beds ⋅ 2 Baths
Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing & electrical, new flooring & paint, jacuzzi, and much more. OWNER FINANCING AVAILABLE. Call for details.

407 W Sunset Ave, Greensboro

Listing courtesy of R&R Executive Realty. Contact: 4104321223
$359,000
4 Beds ⋅ 4 Baths
Welcome to this spacious three-level home offering flexible living space and a functional floor plan! The main level features a bright living room that flows in the open kitchen. Separate dining room for those family gatherings. Also, on this level is a half bath and a small guest bedroom or turn into your reading area or an office space. Upstairs, you'll find three additional bedrooms and the laundry room conveniently located on the same level. The finished lower level provides endless possibilities and can be customized to fit your needs -family room, home office, gym, recreation area or additional living space. Enjoy outdoor living on the large rea deck overlooking the fenced backyard, while the covered front porch provides a welcoming place to relax and unwind. Plenty of room to make this home your own. Solar panels complete this amazing home.

410 Wood Duck Dr, Greensboro

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

$299,990
4 Beds ⋅ 2 Baths
Come discover 121 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 cabinet space, stainless steel appliances, a sizeable island with room for seating and a pantry closet. The home’s fourth bedroom is situated away from the other bedrooms providing the opportunity for a home office, hobby room or playroom. The laundry room is nestled 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.

121 Hobbs St, Greensboro

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact: 3017013700
$215,000
3 Beds ⋅ 1 Baths
Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31, 2027. The property is well-maintained and conveniently located near local amenities, schools, and major routes. Please allow adequate notice for all showings.

105 Lincoln, Greensboro

Listing courtesy of Taylor Properties. Contact:

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