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Homes for Sale in 21639

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  • 110 N School St, Greensboro, MD 21639
    110 N School St, Greensboro, MD 21639
    110 N School St, Greensboro, MD 21639
    /68

    $329,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    110 N School St, Greensboro, MD 21639

    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

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    110 N School St, Greensboro, MD 21639
  • 111 Maple Ave, Greensboro, MD 21639
    111 Maple Ave, Greensboro, MD 21639
    111 Maple Ave, Greensboro, MD 21639
    /49

    $315,000

    Open House 8/15
    • 4 Beds
    • 2 Baths
    • 2,774 Sq Ft

    111 Maple Ave, Greensboro, MD 21639

    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

    Barbara McCaffrey Redfin Corp

    111 Maple Ave, Greensboro, MD 21639
  • 000 Knife Box Rd, Greensboro, MD 21639
    000 Knife Box Rd, Greensboro, MD 21639
    000 Knife Box Rd, Greensboro, MD 21639
    /73

    $790,000

    $49K PRICE DROP
    • Land
    • 87 Acres
    • $9,080 per Acre

    000 Knife Box Rd, Greensboro, MD 21639

    PRICE IMPROVEMENT!!Located just outside Greensboro in Caroline County, Maryland, this exceptional 87 acre property offers a rare combination of income-producing farmland, diverse wildlife habitat, scenic natural features, and a highly developed hunting setup. The property consists of approximately 50 acres of mature woodland and 37 acres of productive tillable acreage, creating an ideal blend of

    Mike Arajakis Whitetail Properties Real Estate

    000 Knife Box Rd, Greensboro, MD 21639
  • 407 W Sunset Ave, Greensboro, MD 21639
    407 W Sunset Ave, Greensboro, MD 21639
    407 W Sunset Ave, Greensboro, MD 21639
    /40

    $280,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,884 Sq Ft

    407 W Sunset Ave, Greensboro, MD 21639

    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 &

    Raphael Szendro R&R Executive Realty

    407 W Sunset Ave, 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
  • 13790 Drapers Mill Rd, Greensboro, MD 21639
    13790 Drapers Mill Rd, Greensboro, MD 21639
    13790 Drapers Mill Rd, Greensboro, MD 21639
    /22

    $389,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,624 Sq Ft

    13790 Drapers Mill Rd, Greensboro, MD 21639

    4 bedroom 2 bath rancher on 3.6 spacious acres on the headwaters of the Choptank.

    Scott Judy Coldwell Banker Waterman Realty

    13790 Drapers Mill Rd, Greensboro, MD 21639
  • 115 Boyce Mill Rd, Greensboro, MD 21639
    115 Boyce Mill Rd, Greensboro, MD 21639
    115 Boyce Mill Rd, Greensboro, MD 21639
    /29

    $289,000

    $41K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,350 Sq Ft

    115 Boyce Mill Rd, Greensboro, MD 21639

    Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive. Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‐beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to the

    Kathleen Brenton Brenton Realty Group

    115 Boyce Mill 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
  • 410 Wood Duck Dr, Greensboro, MD 21639
    410 Wood Duck Dr, Greensboro, MD 21639
    410 Wood Duck Dr, Greensboro, MD 21639
    /42

    $359,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,712 Sq Ft

    410 Wood Duck Dr, Greensboro, MD 21639

    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

    Pamela Geib Long & Foster Real Estate, Inc.

    410 Wood Duck Dr, Greensboro, MD 21639
  • 0 Quail Ct Unit MDCM2007622, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2007622, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2007622, Greensboro, MD 21639
    /20

    $449,000

    New Construction
    • 3 Beds
    • 2 Baths

    0 Quail Ct Unit MDCM2007622, Greensboro, MD 21639

    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

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Quail Ct Unit MDCM2007622, Greensboro, MD 21639
  • 13926 Quail Ct, Greensboro, MD 21639
    13926 Quail Ct, Greensboro, MD 21639
    13926 Quail Ct, Greensboro, MD 21639
    /28

    $440,000

    New Construction $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft

    13926 Quail Ct, Greensboro, MD 21639

    Brand‐new construction in a peaceful country setting! Enjoy effortless one‐level living in this bright, open‐concept rancher designed for comfort and convenience. The spacious living, dining, and kitchen areas flow seamlessly together, creating an inviting space for everyday life and entertaining. BONUS! Seller upgrades are already included! Skip the extra expense - these desirable upgrades are

    Amanda Morgan Brenton Realty Group

    13926 Quail Ct, Greensboro, MD 21639
  • 11502 Greensboro Rd, Greensboro, MD 21639
    11502 Greensboro Rd, Greensboro, MD 21639
    11502 Greensboro Rd, Greensboro, MD 21639
    /16

    $299,900

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    11502 Greensboro Rd, Greensboro, MD 21639

    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

    Pamela Geib Long & Foster Real Estate, Inc.

    11502 Greensboro Rd, Greensboro, MD 21639
  • 707 W Sunset Ave, Greensboro, MD 21639
    707 W Sunset Ave, Greensboro, MD 21639
    707 W Sunset Ave, Greensboro, MD 21639
    /8

    $130,000

    • Land
    • 1.01 Acres
    • $128,713 per Acre

    707 W Sunset Ave, Greensboro, MD 21639

    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.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • 205 N Academy St, Greensboro, MD 21639
    205 N Academy St, Greensboro, MD 21639
    205 N Academy St, Greensboro, MD 21639
    /30

    $249,900

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    205 N Academy St, Greensboro, MD 21639

    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

    Lee Wolff FSBO Broker

    205 N Academy St, Greensboro, MD 21639
  • 530 Vaughn Ave, Greensboro, MD 21639
    530 Vaughn Ave, Greensboro, MD 21639
    530 Vaughn Ave, Greensboro, MD 21639
    /35

    $265,000

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    530 Vaughn Ave, Greensboro, MD 21639

    **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

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, 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
    /14

    $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
  • 14236 Drapers Mill Rd, Greensboro, MD 21639
    14236 Drapers Mill Rd, Greensboro, MD 21639
    14236 Drapers Mill Rd, Greensboro, MD 21639
    /29

    $700,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    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

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • 309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    /30

    $279,900

    $40K PRICE DROP
    • 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

    $359,900

    $15K PRICE DROP
    • 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 the cozy light filled living-dining area, the versatile bonus room/office and the entertainment-ready basement with a unique custom bar.

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • 105 Lincoln St, Greensboro, MD 21639
    105 Lincoln St, Greensboro, MD 21639
    /2

    $215,000

    • 3 Beds
    • 1 Bath
    • 756 Sq Ft

    105 Lincoln St, Greensboro, MD 21639

    Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31st. Tenants have expressed interest in renewing and would prefer to stay, providing potential for continued occupancy. Property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all

    emily conley Taylor Properties

    105 Lincoln St, Greensboro, MD 21639
  • 121 Hobbs St, Greensboro, MD 21639
    121 Hobbs St, Greensboro, MD 21639
    /2

    $299,990

    New Construction $2K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    121 Hobbs St, Greensboro, MD 21639

    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.

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • 109 Hobbs St, Greensboro, MD 21639
    109 Hobbs St, Greensboro, MD 21639
    109 Hobbs St, Greensboro, MD 21639
    /23

    $289,990

    New Construction $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    109 Hobbs St, Greensboro, MD 21639

    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

    D.R. Horton Builder
    109 Hobbs 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
  • 0 Mill & Lincoln St, Greensboro, MD 21639
    0 Mill & Lincoln St, Greensboro, MD 21639
    0 Mill & Lincoln St, Greensboro, MD 21639
    /8

    $85,000

    • Land
    • 32,234 Sq Ft
    • $114,865 per Acre

    0 Mill & Lincoln St, Greensboro, MD 21639

    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

    Erin Anderson Chesapeake Real Estate Associates, LLC

    0 Mill & Lincoln St, Greensboro, MD 21639
  • 108 N Academy St, Greensboro, MD 21639
    108 N Academy St, Greensboro, MD 21639
    108 N Academy St, Greensboro, MD 21639
    /31

    $269,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    108 N Academy St, Greensboro, MD 21639

    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

    Marcia Rostien Long & Foster Real Estate, Inc.

    108 N Academy St, Greensboro, MD 21639
Maryland Caroline County Greensboro

Real Estate & Homes for Sale in 21639

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