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Greensboro, MD Homes for Sale

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  • 12820 Porters Landing Rd, Greensboro, MD 21639
    12820 Porters Landing Rd, Greensboro, MD 21639
    12820 Porters Landing Rd, Greensboro, MD 21639
    /72

    $720,000

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft

    12820 Porters Landing Rd, Greensboro, MD 21639

    The Ultimate Secluded Waterfront Retreat! Privately positioned along the Choptank River, this 12.43 acre waterfront property is surrounded by mature trees, open sky, and abundant natural beauty. The mostly wooded landscape offers privacy and tranquility, creating a peaceful escape that feels worlds away yet remains connected to the charm of Maryland’s Eastern Shore. Outdoor amenities elevate the

    Agent Photo

    Penny Hollis

    Keller Williams Select Realtors of Annapolis

    (410) 834-0596

    12820 Porters Landing Rd, Greensboro, MD 21639
  • 103 Park Ave Unit 36203275, Greensboro, MD 21639
    103 Park Ave Unit 36203275, Greensboro, MD 21639
    103 Park Ave Unit 36203275, Greensboro, MD 21639
    /24

    $294,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    Sullivan Plan at Kinnamon Meadows, Greensboro, MD 21639

    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, modern cabinetry, and an optional island with seating that is perfect for casual

    D.R. Horton Builder
    103 Park Ave Unit 36203275, Greensboro, MD 21639
  • 309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    /36

    $299,900

    • 3 Beds
    • 1.5 Baths
    • 1,791 Sq Ft

    309 N Main St, Greensboro, MD 21639

    This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the

    Eddie Matthews Benson & Mangold, LLC

    309 N Main St, Greensboro, MD 21639
  • 412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    /43

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into a living-dining area anchored by a cozy wood-burning fireplace, the versatile bonus room/office and the entertainment-ready basement with a

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • 103 Park Ave Unit 36203274, Greensboro, MD 21639
    103 Park Ave Unit 36203274, Greensboro, MD 21639
    /2

    $298,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Helena Plan at Kinnamon Meadows, Greensboro, MD 21639

    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

    D.R. Horton Builder
    103 Park Ave Unit 36203274, Greensboro, MD 21639
  • 13306 Greensboro Rd, Greensboro, MD 21639
    13306 Greensboro Rd, Greensboro, MD 21639
    13306 Greensboro Rd, Greensboro, MD 21639
    /48

    $355,000

    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • 103 Park Ave Unit 36203273, Greensboro, MD 21639
    103 Park Ave Unit 36203273, Greensboro, MD 21639
    103 Park Ave Unit 36203273, Greensboro, MD 21639
    /22

    $269,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    Perry Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern cabinetry, stainless steel appliances, a spacious peninsula

    D.R. Horton Builder
    103 Park Ave Unit 36203273, Greensboro, MD 21639
  • 127 Hobbs St, Greensboro, MD 21639
    127 Hobbs St, Greensboro, MD 21639
    127 Hobbs St, Greensboro, MD 21639
    /20

    $272,490 New Construction

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    127 Hobbs St, Greensboro, MD 21639

    Discover a new home at 127 Hobbs Street in the Kinnamon Meadows community of Greensboro, MD. This home is soon to be under construction. This 1,059 square foot open concept cottage-style ranch home offers two bedrooms, two bathrooms, and a two-car driveway. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for

    D.R. Horton Builder
    127 Hobbs St, Greensboro, MD 21639
  • 408 Bernard Ave, Greensboro, MD 21639
    408 Bernard Ave, Greensboro, MD 21639
    408 Bernard Ave, Greensboro, MD 21639
    /11

    $262,500

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    408 Bernard Ave, Greensboro, MD 21639

    This charming ranch-style home in the serene Town of Greensboro offers a perfect blend of comfort and functionality. With 1,232 square feet of well-designed living space, this residence features three inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm and welcoming atmosphere, highlighted by plush carpeting and stylish vinyl

    Daniel Hill Long & Foster Real Estate, Inc.

    408 Bernard Ave, Greensboro, MD 21639
  • 320 N Main St, Greensboro, MD 21639
    320 N Main St, Greensboro, MD 21639
    320 N Main St, Greensboro, MD 21639
    /40

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    320 N Main St, Greensboro, MD 21639

    Welcome to 320 N Main St in the quaint town of Greensboro, where you'll find a home that invites you to kick off your shoes and stay a while. This residence sits on a half-acre lot and features three bedrooms and 2.5 baths, offering an ideal balance of space, comfort, and style. The beautifully updated kitchen is ready for all your culinary adventures, boasting a five-burner gas range, stainless

    Karen Clark Clark & Co Realty, LLC

    320 N Main St, Greensboro, MD 21639
  • 25548 Hill Rd, Greensboro, MD 21639
    25548 Hill Rd, Greensboro, MD 21639
    25548 Hill Rd, Greensboro, MD 21639
    /13

    $435,000

    • Studio
    • 7,260 Sq Ft

    25548 Hill Rd, Greensboro, MD 21639

    HUGE POTENTIAL. Residential/commercial property combined. 4 residential units available. Two units occupied with annual leases (one at $700.00 and the other at $725.00). Two units vacant (one needs some work and the other needs extensive work. All 4 units are Certified Lead Free. Large main section is gutted and has excellent potential for apartments, etc. Buyer and or Buyer's agent to

    Rosa Tyre Kelark Real Estate

    25548 Hill Rd, Greensboro, MD 21639
  • 517 W Sunset Ave, Greensboro, MD 21639
    517 W Sunset Ave, Greensboro, MD 21639
    517 W Sunset Ave, Greensboro, MD 21639
    /4

    $345,000

    • Studio
    • 2,260 Sq Ft

    517 W Sunset Ave, Greensboro, MD 21639

    Three unit apartment building. Two 1bedroom apartments, one 2 bedroom. Fully leased with positive income to support expense and debt service

    Randy Staats Benson & Mangold, LLC

    517 W Sunset Ave, Greensboro, MD 21639
  • 125 Hobbs St, Greensboro, MD 21639

    $286,490 New Construction

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    125 Hobbs St, Greensboro, MD 21639

    Discover 125 Hobbs Street, a new home soon to be 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

    D.R. Horton Builder
    125 Hobbs St, Greensboro, MD 21639
  • 107 N School St Unit 3B, Greensboro, MD 21639
    107 N School St Unit 3B, Greensboro, MD 21639
    /2

    $179,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 968 Sq Ft

    107 N School St Unit 3B, Greensboro, MD 21639

    Rare Opportunity ! Built 1922 as a school and converted into condo units. Many of the original elements make each building unique. With massive windows different architectural elements makes each unit distinctive. Open floor plan with updated appliances make this turn key for its next resident.. This unit has Two comfortable size bedrooms, two full baths, washer and dryer. There is an owner

    Kat Thompson Benson & Mangold, LLC.

    107 N School St Unit 3B, Greensboro, MD 21639
  • 103 Park Ave Unit 36203276, Greensboro, MD 21639
    103 Park Ave Unit 36203276, Greensboro, MD 21639
    103 Park Ave Unit 36203276, Greensboro, MD 21639
    /3

    $282,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. 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

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639
  • 502 W Sunset Ave, Greensboro, MD 21639
    502 W Sunset Ave, Greensboro, MD 21639
    502 W Sunset Ave, Greensboro, MD 21639
    /31

    $269,900

    • 3 Beds
    • 1.5 Baths
    • 1,155 Sq Ft

    502 W Sunset Ave, Greensboro, MD 21639

    Renovated & Move-In Ready with Detached 2-Car Garage! Welcome to this beautifully updated 3-bedroom, 1.5-bath home where modern style meets everyday comfort. From the moment you step inside, you’ll notice the fresh, clean feel created by brand-new LVP flooring, recessed lighting, fresh paint throughout, and a completely renovated kitchen and bathroom designed with today’s buyer in mind.The

    Pamela Geib Long & Foster Real Estate, Inc.

    502 W Sunset Ave, Greensboro, MD 21639
  • 102 S Academy St, Greensboro, MD 21639
    102 S Academy St, Greensboro, MD 21639
    102 S Academy St, Greensboro, MD 21639
    /36

    $249,900

    • 3 Beds
    • 3 Baths
    • 1,678 Sq Ft

    102 S Academy St, Greensboro, MD 21639

    Classic Charm Meets In-Town Living. Enjoy the luxury of space on this generous .34-acre lot, featuring a 3-bedroom home designed for both quiet mornings on the front porch and lively backyard BBQs. Inside, flow seamlessly from the bright & airy living room to the dining area and kitchen. With three full baths, a dedicated laundry room, and a storage-ready basement, the layout is as functional as

    Karen Clark Clark & Co Realty, LLC

    102 S Academy St, Greensboro, MD 21639
  • 2 N Main St, Greensboro, MD 21639
    2 N Main St, Greensboro, MD 21639
    2 N Main St, Greensboro, MD 21639
    /19

    $50,000

    • Land
    • 0.37 Acre
    • $135,135 per Acre

    2 N Main St, Greensboro, MD 21639

    Cleared and ready for your vision! This 1/3+ acre in-town parcel offers the perfect canvas for your new build. Buyer to perform all due diligence with the Town regarding development requirements, including costs for water and sewer allocation.

    Karen Clark Clark & Co Realty, LLC

    2 N Main St, Greensboro, MD 21639
  • 13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    /99

    $1,099,000

    • 6 Beds
    • 3.5 Baths
    • 3,704 Sq Ft

    13539 Hokum Dr, Greensboro, MD 21639

    A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining!Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces,

    Vincent Payne Realty Navigator

    13539 Hokum Dr, Greensboro, MD 21639
Maryland Caroline County Greensboro

Real Estate & Homes for Sale in Greensboro, MD

Why Live in Greensboro

Greensboro, MD is a tranquil riverside town located along the Choptank River in Caroline County. Founded in 1732 and originally named Bridge Towne, Greensboro evolved from a trade hub into a quiet village with a rich history in shipbuilding and agriculture. Homebuyers can find a variety of traditional home styles, including Nationals and colonials from the 1800s, modern ranch-style houses, and newer Colonial Revivals and cottages. Main Street offers shopping essentials with stores like Dollar General, Save a Lot, and Family Dollar, while dining spots include La Delizia Pizza and Tenchi Spanish American Kitchen. For larger shopping needs, residents often travel 7 miles south to Denton. The Greensboro Volunteer Fire Company hosts community events such as the annual carnival in July, a fall tractor pull, and the Greensboro Music Fest & Car Show in September. Outdoor recreation is abundant with the Greensboro Community Park providing a boat ramp for kayaking and fishing, and the Pelot Bird Sanctuary offering trails for birdwatching. Skydive Chesapeake, located 5 miles west, offers tandem and solo skydiving experiences. Tuckahoe State Park, less than 10 miles away, features nearly 20 miles of hiking trails. Commuting is facilitated by Greensboro Road, which connects to State Route 404, and Baltimore/Washington International Airport is 60 miles away.

Learn more about living in Greensboro

Frequently Asked Questions

What is the average home price in Greensboro, MD?
Homes for sale in Greensboro, MD have an average home price of $316,837.
Are home prices dropping in Greensboro?
Yes, home prices in Greensboro are down 1% in the last 12 months.
How many homes have sold over the last 12 months in Greensboro, MD?
87 homes have sold in Greensboro, MD over the last 12 months.
What are the most popular zip codes in Greensboro, MD?
The most popular zip codes in Greensboro, MD include 21639, 21636, 21660, 19943 and 21629.
How much do you need to make to afford a house in Greensboro?
The median home price in Greensboro is $282,990. If you put a 20% down payment of $56,600 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,410 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $60K a year to afford the median home price in Greensboro. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Greensboro, MD?
Greensboro, MD has highly rated public and private schools. Some of the best schools in Greensboro based on Niche Grades are Greensboro Elementary School, Lockerman Middle School and North Caroline High School. Browse all the schools in Greensboro, MD to learn more.

Home Trends in Greensboro, MD

On average, homes in Greensboro, MD sell after 64 days on the market compared to the national average of 55 days. The median sale price for homes in Greensboro, MD over the last 12 months is $280,000, down 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$280,000
Median Single Family Sale Price
$285,740
Median Townhouse Sale Price
$235,000
Average Price Per Sq Ft
$206
Number of Homes for Sale
16
Last 12 months Home Sales
87
Months of Supply
2.20
Median List Price
$282,990
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-11%
How to Buy a Home How to Finance a Home How to Sell a Home

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