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

$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:

$449,000
3 Beds ⋅ 2 Baths
TBB....This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. . Enclosed Sunporch that leads to back patio and Front porch for your morning coffee. Enjoy an oversized attached two-car garage and a rear deck perfect for outdoor living. Encapsulated conditioned crawl space . Situated on a cleared 1-acre lot in a private rural setting, this home offers the best of both worlds—peaceful surroundings with a convenient location for Delaware commuters. Close to beaches, shopping, and a nearby public boat ramp. The builder includes a generous package of upgrades at no additional cost. Call today and make an appointment to meet the Builder and give him all your wants and needs. Pictures are from the model home. Home will break ground in August. Note: Taxes reflect land only. Once house is built they will change to reflect House and Land. Buyer to check with the County to get your annual fee.

Quail Ct, 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
$259,900
3 Beds ⋅ 1 Baths
Welcome to this fully remodeled ranch, perfectly situated on a level lot on a quiet street. The showstopper kitchen features white shaker cabinets with dovetailed soft-close drawers, white quartz countertops, tile backsplash, and stainless steel appliances. Every inch of this home has been thoughtfully updated with new LVP flooring, plush carpet, fresh paint, and new lighting throughout. The renovated bathroom shines with a new vanity, tub, and tiled surround, while a brand new roof and cooling system offer true peace of mind. New flooring, paint, and fixtures flow seamlessly from room to room, giving the entire home a fresh, move-in ready feel. A detached shop provides the perfect bonus space for hobbies, storage, or weekend projects. This is the turnkey ranch you've been waiting for — schedule your showing today before it's gone!

205 N Academy St, Greensboro

Listing courtesy of FSBO Broker. Contact: 7173947283
$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
$342,500
3 Beds ⋅ 2 Baths
Pride of ownership is shown from top to bottom in this magnificent rancher! This custom-built home was completed in June 2025 and is like new. The owner took much pride in everything he installed/built and makes this home very desirable. The nine-foot (9') ceilings add the feeling of openness to go with the open floor plan of the living room/dining area/kitchen with an easy flow from one area to the next. The kitchen features granite counter tops, double sink with Moen faucet, Insta-Hot water system, Samsung stainless steel appliances (the stove can easily be changed out to gas as the seller has all lines in place for propane if new owner ever wants to change over to gas). The kitchen has all-wooden cabinetry. The bedrooms are roomy and are prewired for TV and internet service. The attic is accessed by steel pull-down stairs with a 300-lb weight capacity.. The attic has flooring making for great storage areas; The attic has spray foam and Batt insulation as well as an attic zippered tent to keep the heat from escaping from the main level. There is an electric auto hookup on side of home; hot and cold water faucet on the side of the home to service a camper if needed; recessed exterior lighting on both porches; 4' sidewalks to both entrances. Front porch is 6' wide and rear porch is 8' wide. High-grade designed encapsulated crawlspace with dehumidifier, lots of lighting, French drains with sump pump (if ever a need arose), with concrete slab flooring, and an insulated entry door. The mechanical room with heat and AC, houses the controls for electric, Insta-hot water, hookups for cable & TV with connections to every bedroom with CAT-5 and coax. Yard is 60 ft wide and 100 ft deep. So much more to enjoy!! Come see this exceptional home today and you can 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:

$307,000
3 Beds ⋅ 2 Baths
This is an auction property. This property has been placed in an upcoming event. Please reach out to the listing agent on where the bids are to be submitted. Please submit any pre-auction offer received through the property details page, please reach out to the listing agent. Any post-auction offers will need to be submitted directly to the listing agent. Response within 3 business days. All properties are subject to a 5% buyer s premium pursuant to the Auction Participation Agreement and Terms & Conditions minimums will apply. Please contact listing agent for details.

11502 Greensboro Rd, Greensboro

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

$289,990
3 Beds ⋅ 2 Baths
**Red Tag Sales Event through August 2, 2026! Was $304,990 Now: $289,990!** Welcome to 109 Hobbs Street where a new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen boasts stainless steel appliances, contemporary gray cabinetry, and granite countertops perfect for casual meals or entertainment. Across from the kitchen, a tucked-away hallway leads to the pantry, a convenient coat closet, and the laundry room, keeping everyday essentials neatly organized. The kitchen flows seamlessly into the dining area and great room, creating a bright, welcoming space ideal for gatherings or relaxing evenings. Set quietly at the back of the home, the large main bedroom serves as a peaceful retreat with a private bath, single vanity, walk-in shower, and an impressive walk-in closet. 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.

109 Hobbs St, Greensboro

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact: 3017013700
$700,000
3 Beds ⋅ 2 Baths
STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique opportunity features a spacious all-brick home paired with a large commercial building designed for flexibility and function. The commercial space includes a showroom, mechanic area with lift, two offices, two bathrooms, heat and air conditioning, and an expansive paved parking lot. Previously operated as a dealership, the seller still holds a trader’s license, offering exceptional potential for a variety of business uses. The well-maintained home offers 3 spacious bedrooms and 2 full baths, along with a comfortable living room, dining room, and kitchen featuring stainless steel appliances. Additional highlights include hardwood floors beneath the carpet, a welcoming front porch, full basement, attached carport, and paved driveway. Some major improvements have already been completed, including a new roof (2025), new gutters with leaf protection (2025), and a new deep well (2025). The commercial building and home are separately metered and each have their own well and septic systems. The seller was in the process of subdividing the property, with much of the work already completed. This creates additional flexibility and potential for future owners, as a buyer may choose to complete the subdivision process, allowing the house and commercial building to be sold or leased separately. Buyer to verify all zoning, permitted uses, and business opportunities with the county and conduct their own due diligence regarding sudivision status and intended use of the property. Contact me today for more information or to schedule your private tour. Properties like this don’t come around often, act fast and secure your future before it's gone.

14236 Drapers Mill Rd, Greensboro

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183
$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
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