2,043

Caroline, MD Homes

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  • /34

    $299,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    104 Hobbs St, Greensboro, MD 21639

    Fully Remodeled 3-Bedroom Home – Modern Comfort Meets Timeless CharmWelcome to 104 Hobbs St, where quality craftsmanship and stylish upgrades define this beautifully updated 3-bedroom, 1-bath home with 1,248 square feet of living space. Completely renovated from the studs, this home offers peace of mind with all-new electrical, plumbing systems, HVAC, roof & siding plus a fresh modern

    Brett Schrader Taylor Properties

    104 Hobbs St, Greensboro, MD 21639
  • /15

    $50,000 Sold May 27, 2025

    • 708 Sq Ft
    • $71/SF
    • 153 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1962

    13306 Greensboro Rd, Greensboro, MD 21639

    Investor Alert! Bring your imagination and turn this home into a gem with a water view in charming Greensboro. Minutes to several state parks, recreational facilities, restaurants, cafes and shopping. Schedule your tour today and also experience the Town's rich history, outdoor activities on the Choptank River such as fishing, kayaking or just enjoy the nature .

    Dalton Adshead Keller Williams Select Realtors of Cambridge

    13306 Greensboro Rd, Greensboro, MD 21639
    • /3

      Est $498,886 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      12141 Greensboro Rd, Greensboro, MD 21639

      12141 Greensboro Rd, Greensboro, MD 21639
  • /6

    $200,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    306 Bernard Ave, Greensboro, MD 21639

    Step into this delightful home that perfectly blends comfort with convenience. The open-concept living and kitchen area creates an inviting space for relaxing or entertaining, complete with effortless flow and natural light. With two well-sized bedrooms and a full bathroom, it's ideal for small households or anyone seeking a cozy oasis.From the kitchen, step out onto the oversized back

    Amanda Morgan Brenton Realty Group

    306 Bernard Ave, Greensboro, MD 21639
  • /12

    $176,400 Sold May 23, 2025

    • 1,155 Sq Ft
    • $153/SF
    • 223 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1948

    502 W Sunset Ave, Greensboro, MD 21639

    3 bedroom rancher located near the town park and within walking distance to many of the town's great features. It has a detached 2 car garage and a deck off of the back of the house. Large kitchen off of the living room and a separate bedroom floor plan.

    Pamela Geib Long & Foster Real Estate, Inc.

    502 W Sunset Ave, Greensboro, MD 21639
    • /26

      Est $275,952 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      139 Smugglers Way, Greensboro, MD 21639

      139 Smugglers Way, 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
  • /59

    $385,000 Sold May 12, 2025

    • 1,568 Sq Ft
    • $246/SF
    • 203 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1979

    25820 Dogwood Rd, Greensboro, MD 21639

    Looking for that awesome oasis, come check out this 3-bedroom, 2.5-bathroom home. Sit on the multi-level decks or hang out on the patio. Corner lot with a circular drive in the front and extra wide space for parking in the rear. Main level boosts kitchen, family room combo, separate dining room and large living room. Inside access to the lower level that is finished plus you could enter from

    Pamela Geib Long & Foster Real Estate, Inc.

    25820 Dogwood Rd, Greensboro, MD 21639
    • /20

      Est $364,841 Not Listed For Sale

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

      103 Elmor Ct, Greensboro, MD 21639

      103 Elmor Ct, Greensboro, MD 21639
  • /20

    $230,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    218 E Sunset Ave, Greensboro, MD 21639

    Welcome to 218 E Main St Greensboro, MD. This home offers 3 bedrooms and 1 bath. Home has a large, dethatched garage and off-street parking. Located next to the public boat ramp, with easy access to local shopping and Delaware tax free shopping. This home is located in a flood zone and is being sold as is. Sellers are offering $5,000 in closing assistance with acceptable offer!

    Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

    218 E Sunset Ave, Greensboro, MD 21639
  • /17

    $245,000 Sold May 09, 2025

    • 1,786 Sq Ft
    • $137/SF
    • 9 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1880

    308 W Sunset Ave, Greensboro, MD 21639

    Step into a piece of Greensboro's history with this two-story Victorian home. This large home has four spacious bedrooms and offers ample space for family living and entertaining. The heart of the home, a kitchen remodeled in 2018. The home's exterior had a new roof installed in 2022 and windows replaced in 2023, ensuring both aesthetic appeal and energy efficiency. Nestled in the town of

    Heather Brummell Shore Living Real Estate

    308 W Sunset Ave, Greensboro, MD 21639
    • /52

      Est $318,605 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,559 Sq Ft

      201 Church St, Greensboro, MD 21639

      201 Church St, Greensboro, MD 21639
  • /42

    $239,000

    • 3 Beds
    • 2 Baths
    • 1,212 Sq Ft

    102 Roe St, Greensboro, MD 21639

    This 3-bedroom, 2-bath bungalow offers the perfect blend of warmth, space, and character. Set on a quiet street just minutes from downtown Greensboro. Step inside to a bright, welcoming living area and enjoy the comfort of a wood stove that keeps the whole house cozy during the winter months.The layout offers flexibility with three comfortable bedrooms and two full baths, providing just

    Jillian Luna Rosendale Realty

    102 Roe St, Greensboro, MD 21639
  • /36

    $455,000 Sold May 09, 2025

    • 2,100 Sq Ft
    • $217/SF
    • 28 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    11412 Cecil Ct, Greensboro, MD 21639

    Charming 4-Bedroom Home with Water Access & Wooded Views!Nestled just 2.1 miles off Route 404, this adorable 4-bedroom, 2.5-bath home offers the perfect blend of comfort and convenience. Located in a picturesque neighborhood with water access, this home is a true gem! Key Features: First-floor owner’s suite for easy living Open-concept kitchen & dining area—great for entertaining Partially fenced

    Deborah Shiley Long & Foster Real Estate, Inc.

    11412 Cecil Ct, Greensboro, MD 21639
    • /54

      Est $335,276 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      203 Wood Duck Dr, Greensboro, MD 21639

      203 Wood Duck Dr, Greensboro, MD 21639
  • /5

    $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
  • /3

    $140,000 Sold Apr 30, 2025

    • 1,764 Sq Ft
    • $79/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1948

    104 Roe St, Greensboro, MD 21639

    Calling all savvy investors! This 3-bedroom, 1-bath is your next golden opportunity in the charming town of Greensboro. Whether you're looking to rent or add to your portfolio, this property's got the bones you need. Furnace less than 1 year old and roof is in great shape. With the right touch this will be someone's dream home once again! Property being sold as it.

    Heather Brummell Shore Living Real Estate

    104 Roe St, Greensboro, MD 21639
    • /30

      Est $319,649 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,848 Sq Ft

      313 Mallard Dr, Greensboro, MD 21639

      313 Mallard Dr, Greensboro, MD 21639
  • /10

    $195,000

    • Land
    • 15 Acres
    • $13,338 per Acre

    12837 Ridgely Rd, Greensboro, MD 21639

    14.62 acres of privacy, nature, and waterfront access. This wooded recreational lot offers — a serene wooded 14.62 acre escape surrounded by the Choptank River.This vacant property is perfect for hunting, camping, kayaking, and outdoor enjoyment. The woods offer access for hiking, exploring, and wildlife watching — including deer, turkeys, and geese. This lot is not perc approved and has no

    Melissa Tippett TTR Sotheby's International Realty

    12837 Ridgely Rd, Greensboro, MD 21639
  • /17

    $90,000 Sold Apr 30, 2025

    • Land
    • 2.44 Acres
    • $36,885 per Acre
    • 3 Days On Market

    13870 Drapers Mill Rd, Greensboro, MD 21639

    Almost 200 feet of Choptank River frontage! Live where the white perch spawn & kayak out your back door! Site plans and septic approval for a 4 bedroom home has already been completed! Steps to the waters edge are there for your convenience to start enjoying what this lot has to offer now! A 40 X 8, 9.5’ tall shipping container conveys with the property for your storage needs. It’s foundation is

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    13870 Drapers Mill Rd, Greensboro, MD 21639
    • /31

      Est $359,665 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft

      25797 Spring Branch Dr, Greensboro, MD 21639

      25797 Spring Branch Dr, Greensboro, MD 21639
  • /35

    $615,000

    • 3 Beds
    • 2 Baths
    • 1,651 Sq Ft

    12459 Kibler Rd, Greensboro, MD 21639

    Outstanding small farm property on quiet country road! This spacious home features 3 bedrooms and two baths, kitchen with new stainless steel appliances, breakfast bar and dining area. The large living room with wood floors over looks the expansive front yard and opens to the front porch where you can enjoy your morning coffee. In the rear of the home there is a large family room that offers

    Marcia Rostien Long & Foster Real Estate, Inc.

    12459 Kibler Rd, Greensboro, MD 21639
  • /39

    $355,000 Sold Apr 18, 2025

    • 1,688 Sq Ft
    • $210/SF
    • 13 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1990

    25329 Calvert Dr, Greensboro, MD 21639

    Welcome to this 3-bedroom, 2.5-bathroom rancher in the desirable Passapae Landing community! This home offers comfortable living with a 2-car attached garage. Step inside to a tile foyer leading to the living room with plush carpeting. The spacious kitchen features peninsula seating, gas cooking and large pantry. A new sliding door in the breakfast area leads to the back deck and private rear

    Nick Waldner Keller Williams Realty Centre

    25329 Calvert Dr, Greensboro, MD 21639
    • /17

      Est $337,422 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,876 Sq Ft

      205 N Main St, Greensboro, MD 21639

      205 N Main St, Greensboro, MD 21639
  • /10

    $157,500

    • Land
    • 1.01 Acres
    • $155,941 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 and sewer are available. The offering does seem to have some ownership of another parcel consisting of Cosden St. Any interested buyer should perform their own suitable level of due diligence.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • /24

    $165,000 Sold Apr 04, 2025

    • 3,540 Sq Ft
    • $47/SF
    • 54 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1926

    113 N Main St, Greensboro, MD 21639

    Lots of local History!! Most recently -Town Office! Located on Main Street close to all the Shops, Restaurant's and Parks.....Not to mention the Choptank River! This is a Perfect spot for you to make your HOME or BUSINESS. First Floor offers Spacious Foyer Entry , Two Large Parlors, Full Kitchen, Bathroom and enclosed Sun Room/Conference Room. Upstairs includes Four Office/Bedrooms and a Full

    Kathleen Brenton Brenton Realty Group

    113 N Main St, Greensboro, MD 21639
    • /50

      Est $358,194 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,820 Sq Ft

      25922 Fox Grape Rd, Greensboro, MD 21639

      25922 Fox Grape Rd, Greensboro, MD 21639
  • /20

    $169,900

    • Studio
    • 1,608 Sq Ft

    605 W Sunset Ave, Greensboro, MD 21639

    Investment property! Two income producing occupied rentals. 2 bedroom, 1 bath upstairs and 2 bedroom, 1 bath downstairs. Both under lease. Large yard with pleanty of parking! Seller to offer Discount if purchased with 603W Sunset. Has been registered Led free!

    Scott Judy Coldwell Banker Waterman Realty

    605 W Sunset Ave, Greensboro, MD 21639
  • /76

    $630,000 Sold Mar 31, 2025

    • 3,806 Sq Ft
    • $166/SF
    • 43 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1963

    13869 Drapers Mill Rd, Greensboro, MD 21639

    Welcome to 13869 Drapers Mill Road, Greensboro, MD—a home where space, style, and serenity come together!This stunning 6-bedroom, 3.5-bathroom home spans approximately 3,806 square feet, offering all the room you need to live, entertain, and make lifelong memories. Situated on 8.2 acres, the property provides endless opportunities to create your dream outdoor retreat—think pool, pole barn, or

    Jarnell Foster Benson & Mangold, LLC

    13869 Drapers Mill Rd, Greensboro, MD 21639
    • /15

      Est $323,639 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,162 Sq Ft

      522 Bernard Ave, Greensboro, MD 21639

      522 Bernard Ave, Greensboro, MD 21639
  • /14

    $189,900

    • Studio
    • 1,983 Sq Ft

    603 W Sunset Ave, Greensboro, MD 21639

    Investment property! Two income producing occupied rentals. 2 bedroom, 1 bath and 3 beedroom, 1 bath. Both under lease. Large yard with pleanty of parking! Seller to give discount if purchased with 605 W Sunset.Has been registered Led Free!

    Scott Judy Coldwell Banker Waterman Realty

    603 W Sunset Ave, Greensboro, MD 21639
  • /14

    $2,000,000 Sold Mar 21, 2025

    • 1,896 Sq Ft
    • $1055/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1975

    12400 & 12316 Ridgely Rd, Greensboro, MD 21639

    Eastern Shore Maryland Production Farm Offering! This property is located in Caroline County Maryland near the town of Ridgely being situated beside town limits to the western edge. The acreage is as follows, total 175.4+/- acres from the two parcels together 145+/- acres being in a MALPF land preservation and the parcel closest to Ridgley containing 30.4+/- that is not in a MALPF easement. A

    BRIAN MORRIS The Land Group

    12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    • /10

      Est $246,637 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,800 Sq Ft

      312 W Sunset Ave, Greensboro, MD 21639

      312 W Sunset Ave, Greensboro, MD 21639
  • /9

    $87,500

    • Land
    • 0.74 Acre
    • $118,243 per Acre

    0 Mill & Lincoln St, Greensboro, MD 21639

    NEW PRICE!!! Unique Opportunity to purchase 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. Dilapidated dwelling exists in the center of the parcels, in need of tear down or possible major renovation. Town of Greensboro building codes and ordinances

    Erin Anderson Chesapeake Real Estate Associates, LLC

    0 Mill & Lincoln St, Greensboro, MD 21639
  • /7

    $265,000 Sold Mar 05, 2025

    • 1,890 Sq Ft
    • $140/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1981

    128 Mill St, Greensboro, MD 21639

    ?Welcome to 128 Mill Street in Greensboro, Maryland! This charming cape cod home offers stunning views of the Choptank River and a peaceful park in smugglers cove. The great room on the first level features natural light, a brick hearth with a woodstove, one full bathroom. Upstairs, a loft area awaits a second bath, along with two spacious bedrooms. The covered deck is perfect for enjoying

    Phill Whitby Long & Foster Real Estate, Inc.

    128 Mill St, Greensboro, MD 21639
    • /50

      Est $357,286 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft

      315 W Sunset Ave, Greensboro, MD 21639

      315 W Sunset Ave, Greensboro, MD 21639
  • /95

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 2,968 Sq Ft

    25305 Sandy Point Rd, Greensboro, MD 21639

    Discover this stunning three-story waterfront home on the Choptank River, just five minutes from downtown Denton and Route 404. The main level features an eat-in kitchen, formal dining room, and a living room and sunroom—both offering breathtaking river views. You'll also find a spacious primary suite, an additional half bath, and a laundry room. Upstairs, two additional bedrooms, a full bath,

    Janet Larson Benson & Mangold, LLC

    25305 Sandy Point Rd, Greensboro, MD 21639
  • /13

    $190,000 Sold Feb 19, 2025

    • 1,004 Sq Ft
    • $189/SF
    • 7 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1950

    101 Vaughn Ave, Greensboro, MD 21639

    A cottage for an affordable price point. Open floor plan offers a modern take on the classic cottage style.Kitchen with island offers flexibility in entertainment and day to day use. HVAC is only a few years old offering central air conditioning. a large bonus room which the current owners use as a bedroom.Come and see this well priced single family home.FHA, VA, USDA loans welcome.

    Kat Thompson Benson & Mangold, LLC.

    101 Vaughn Ave, Greensboro, MD 21639
    • /10

      Est $187,366 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,236 Sq Ft

      208 N Academy St, Greensboro, MD 21639

      208 N Academy St, Greensboro, MD 21639
  • /5

    $55,000

    • Land
    • 0.27 Acre
    • $203,704 per Acre

    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639

    Prime Opportunity for Walkable Living or Development in Greensboro MD. Attention developers Home Builders and Homeowners - Build Your Dream Home: This vacant at Lot 3 on School Street, offers unmatched potential for creativity and flexibility. With public water and sewer access available, this centrally located lot is primed for growth and offers an incredible opportunity to be part of

    Lisa Knotts Meredith Fine Properties

    402 Lot 3 N S Sunset Ave, Greensboro, MD 21639

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