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

$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
$1,499,999
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
$265,000
3 Beds ⋅ 3 Baths
**Seller is offering $7,500 towards buyers closing costs with an acceptable offer** Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the moment you step inside. The main level offers a bright and inviting living room that flows into the open dining area and kitchen, creating an ideal layout for both everyday living and entertaining. A convenient half bath completes the main level. The kitchen boasts ample cabinet space, features a brand new refrigerator (2025), and provides direct access to the backyard through a sliding glass door. Upstairs, the spacious primary suite showcases soaring vaulted ceilings, a private en-suite bath, and a walk-in closet. Two additional generously sized bedrooms, a second full bathroom, and a dedicated laundry area complete the upper level. The washing machine was replaced in 2024 as an added bonus. Step outside to enjoy the fully fenced backyard featuring a newer vinyl privacy fence (2023), an attached storage shed, and additional side yard space, perfect for gardening, pets, or outdoor activities. Enjoy peace of mind with numerous major upgrades, including a new A/C condenser (2026), new heat pump (2026), and energy-saving blown-in insulation (2026), all added to improve year-round comfort and efficiency. Conveniently located near Routes 313, 480, and 314, this home offers easy access to commuting, shopping, dining, and everyday conveniences. Don't miss your opportunity to own this thoughtfully updated, move-in-ready home!

530 Vaughn Ave, Greensboro

Listing courtesy of Hyatt & Company Real Estate, LLC. Contact:

$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
$85,000
3 Parcels in the Town of Greensboro!! One of which has a hooked up Water/Sewer account, so instant savings on no tap fee!! 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. NOTE: The parcel numbers shown on the tax maps appear to be inaccurate-we have contacted the State Assessors office and they stated they are working on updating their maps and records to correct the discrepancies. Any reasonable offer considered. Seller prefers to sell all 3 parcels together as a unit--does not want to separate at this time. 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:

$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:

$699,000
Exceptional opportunity to own a well-established 2,400-square-foot retail business featuring three revenue streams under one roof: a fully operational deli, liquor store and convenience store. The spacious layout provides efficient customer flow, ample display areas, refrigeration units, storage space, and dedicated deli commercial kitchen. Located in with convenient access to Greensboro and ample parking, this business is positioned for continued success. Whether you're expanding your portfolio or entering the retail market, this one-stop shopping destination presents a rare opportunity to acquire a versatile and established operation. All equipment will convey with the sale of the property.

105 Whiteleysburg Rd, Greensboro

Listing courtesy of Crown Homes Real Estate. Contact: (302) 504-6147
$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:

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