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

$449,900
3 Beds ⋅ 2 Baths
Professional photos and remarks coming soon

421 W Sunset Ave, Greensboro

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$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:

$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
$239,900
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
$1,199,999
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
$250,000
3 Beds ⋅ 3 Baths
**Seller is offering $2,500 towards buyers closing costs with a full price 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
$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:

$329,900
3 Beds ⋅ 2 Baths
Price to purchase has been lowered to help you afford top quality at a fantastic price. Come see this beautiful home. 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:

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