108

Caroline, MD Homes

Section Image
  • 21948 Main St, Hillsboro, MD 21641
    21948 Main St, Hillsboro, MD 21641
    21948 Main St, Hillsboro, MD 21641
    /20

    $219,900

    • 3 Beds
    • 1 Bath
    • 1,904 Sq Ft

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill so little chance of flooding from the Choptank River that is across the street -- with some winter views. The park is across the street with a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be;, and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living

    Bonnie Duley Long & Foster Real Estate, Inc.

    21948 Main St, Hillsboro, MD 21641
  • 21968 Main St, Hillsboro, MD 21641
    21968 Main St, Hillsboro, MD 21641
    21968 Main St, Hillsboro, MD 21641
    /40

    $325,000 Sold Jun 17, 2025

    • 2,704 Sq Ft
    • $120/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    21968 Main St, Hillsboro, MD 21641

    Come take a look at this well maintained four bedroom and two full bath farmhouse. It boasts an upgraded kitchen with stainless steel appliances and granite counter tops. There is a breakfast nook right off the kitchen allowing a great spot to have breakfast in the mornings. The large formal dining room boasts bamboo hardwood floors that stretch into the spacious living room. Let's not forget

    Ross Hunsberger Coldwell Banker Realty

    21968 Main St, Hillsboro, MD 21641
    • 9980 Tuckahoe Rd, Hillsboro, MD 21641
      9980 Tuckahoe Rd, Hillsboro, MD 21641
      9980 Tuckahoe Rd, Hillsboro, MD 21641
      /15

      Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,958 Sq Ft

      9980 Tuckahoe Rd, Hillsboro, MD 21641

      9980 Tuckahoe Rd, Hillsboro, MD 21641
  • 22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    /73

    $545,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle.The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • 11204 Academy St, Hillsboro, MD 21641
    11204 Academy St, Hillsboro, MD 21641
    11204 Academy St, Hillsboro, MD 21641
    /42

    $250,000 Sold Jun 06, 2025

    • 1,328 Sq Ft
    • $188/SF
    • 16 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1800

    11204 Academy St, Hillsboro, MD 21641

    OWN for less than you can rent at this NEWLY listed, ADORABLE turn-key home is ready for her lucky, new owners! Rumored as the 'Frederick Douglass' home, this home exudes charm & character! Boasting gleaming hardwoods, ample natural light, welcoming full-length front porch with gas hook-up to extend outdoor living space, Spacious main-level bedroom, country kitchen w/ built-ins, 14' x 22'

    Jennifer Chaney Chaney Homes, LLC

    11204 Academy St, Hillsboro, MD 21641
    • 22143 Hillsboro Rd, Hillsboro, MD 21641
      22143 Hillsboro Rd, Hillsboro, MD 21641
      22143 Hillsboro Rd, Hillsboro, MD 21641
      /24

      Est $192,058 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,668 Sq Ft

      22143 Hillsboro Rd, Hillsboro, MD 21641

      22143 Hillsboro Rd, Hillsboro, MD 21641
  • E/S MD RT480 Unknown, Hillsboro, MD 21641
    E/S MD RT480 Unknown, Hillsboro, MD 21641
    /2

    $55,000

    • Land
    • 4.17 Acres
    • $13,189 per Acre

    E/S MD RT480 Unknown, Hillsboro, MD 21641

    Seller is waiting for perk results from Caroline county health department

    Diane Wenk Wright Real Estate

    E/S MD RT480 Unknown, Hillsboro, MD 21641
  • 11441 Ridgely Rd, Hillsboro, MD 21641
    11441 Ridgely Rd, Hillsboro, MD 21641
    /2

    $32,500 Sold May 30, 2025

    • Land
    • 0.31 Acre
    • $104,839 per Acre
    • 11 Days On Market

    11441 Ridgely Rd, Hillsboro, MD 21641

    Discover a unique opportunity to own two adjacent parcels on Ridgely Road in beautiful Caroline County. This offering includes the lot at 11441 Ridgely Road along with an additional 1.4-acre lot identified as Tax Map 0021, Parcel 76, Grid 0024. Together, these properties provide ample space and potential for future use.Please note: There is currently no approved perc test on file. Buyers are

    Jarnell Foster Benson & Mangold, LLC

    11441 Ridgely Rd, Hillsboro, MD 21641
    • 22013 Main St, Hillsboro, MD 21641
      22013 Main St, Hillsboro, MD 21641
      22013 Main St, Hillsboro, MD 21641
      /51

      Est $313,175 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,316 Sq Ft

      22013 Main St, Hillsboro, MD 21641

      22013 Main St, Hillsboro, MD 21641
  • 22038 Church St, Hillsboro, MD 21641
    22038 Church St, Hillsboro, MD 21641
    22038 Church St, Hillsboro, MD 21641
    /33

    $191,000 Sold May 20, 2025

    • 1,792 Sq Ft
    • $107/SF
    • 5 Days On Market
    • Studio
    • Built 1950

    22038 Church St, Hillsboro, MD 21641

    Great Investment Opportunity! Spacious Corner lot Duplex offers 2 Units with separate Front Porches, Rear patio's, Storage Sheds and Park across the street. One Unit ready for Occupancy & other currently income producing. Loaf area upstairs in both units could be converted to additional bedrooms. This is a Must see to appreciate - schedule your tour today!

    Mary Mabry Keller Williams Select Realtors of Cambridge

    22038 Church St, Hillsboro, MD 21641
    • 11210 Academy St, Hillsboro, MD 21641
      11210 Academy St, Hillsboro, MD 21641
      11210 Academy St, Hillsboro, MD 21641
      /30

      Est $241,021 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,780 Sq Ft

      11210 Academy St, Hillsboro, MD 21641

      11210 Academy St, Hillsboro, MD 21641
  • 21959 Main St, Hillsboro, MD 21641
    21959 Main St, Hillsboro, MD 21641
    21959 Main St, Hillsboro, MD 21641
    /28

    $285,000 Sold May 09, 2025

    • 2,168 Sq Ft
    • $131/SF
    • 9 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1885

    21959 Main St, Hillsboro, MD 21641

    This waterfront home was built in 1885 and sits on 1.2 acres of land over looking the Tuckahoe Creek. Walk down to waters edge or use the public boat ramp just next door to start your water adventures. This 4 bedroom, 2 bath home offers 2168 sq ft of living space. I love the Vaulted ceilings in the kitchen and Primary Bedroom and the awesome water views from several rooms. The family room

    Jimmy White Long & Foster Real Estate, Inc.

    21959 Main St, Hillsboro, MD 21641
    • 21936 Main St, Hillsboro, MD 21641
      21936 Main St, Hillsboro, MD 21641
      21936 Main St, Hillsboro, MD 21641
      /45

      Est $286,114 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,400 Sq Ft

      21936 Main St, Hillsboro, MD 21641

      21936 Main St, Hillsboro, MD 21641
  • 21954 Main St, Hillsboro, MD 21641
    21954 Main St, Hillsboro, MD 21641
    21954 Main St, Hillsboro, MD 21641
    /73

    $298,000 Sold May 05, 2025

    • 1,996 Sq Ft
    • $149/SF
    • 4 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1900

    21954 Main St, Hillsboro, MD 21641

    Lovingly restored and maintained Victorian charmer, located in the heart of Historic Hillsboro is now searching for a new owner. Stepping inside, you'll be transported to yesteryear as you tread on original hardwood floors and enjoy the neutral paint palette of the generously sized rooms. The living room features a wood burning stove to gather round and enjoy cozy evenings. The dining room and

    Judith Germain Benson & Mangold, LLC

    21954 Main St, Hillsboro, MD 21641
    • 11198 Maple Ave, Hillsboro, MD 21641
      11198 Maple Ave, Hillsboro, MD 21641
      11198 Maple Ave, Hillsboro, MD 21641
      /38

      Est $224,033 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,688 Sq Ft

      11198 Maple Ave, Hillsboro, MD 21641

      11198 Maple Ave, Hillsboro, MD 21641
  • 22040 Main St, Hillsboro, MD 21641
    22040 Main St, Hillsboro, MD 21641
    22040 Main St, Hillsboro, MD 21641
    /83

    $305,000 Sold Feb 13, 2025

    • 2,276 Sq Ft
    • $134/SF
    • 68 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1900

    22040 Main St, Hillsboro, MD 21641

    Welcome to this Grand Victorian home resting on 3 lots for a total of .76 acres with mature planting and ample storage, including 2 outbuildings one a small horse barn with stall and a storage shed with workshop area and a large garage/shop area. This grand home offers large rooms with high ceilings and all the expected original features: beautiful hardwood floors, original pocket doors,

    Roger Boyce Chesapeake Real Estate Associates, LLC

    22040 Main St, Hillsboro, MD 21641
    • 22090 Main St, Hillsboro, MD 21641
      22090 Main St, Hillsboro, MD 21641
      22090 Main St, Hillsboro, MD 21641
      /26

      Est $256,355 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 2,892 Sq Ft

      22090 Main St, Hillsboro, MD 21641

      22090 Main St, Hillsboro, MD 21641
  • 21994 Main St, Hillsboro, MD 21641
    21994 Main St, Hillsboro, MD 21641
    21994 Main St, Hillsboro, MD 21641
    /29

    $234,900 Sold Nov 06, 2024

    • 4,000 Sq Ft
    • $59/SF
    • 139 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1800

    21994 Main St, Hillsboro, MD 21641

    Welcome to this porchfront home in the historic community of Hillsboro. Upon entry, you will find an open floor plan with tile flooring from the living room to the sunroom. The living-dining room combo has a high ceiling that leads to a county kitchen with wood cabinets and appliances, a large master bedroom with en suite bath, and a sunroom with wide windows that is a perfect place for

    Gina Gargeu Century 21 Downtown

    21994 Main St, Hillsboro, MD 21641
    • 11210 Maple Ave, Denton, MD 21629
      11210 Maple Ave, Denton, MD 21629
      11210 Maple Ave, Denton, MD 21629
      /27

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,952 Sq Ft

      11210 Maple Ave, Denton, MD 21629

      11210 Maple Ave, Denton, MD 21629
    • 21984 Main St, Hillsboro, MD 21641
      21984 Main St, Hillsboro, MD 21641
      21984 Main St, Hillsboro, MD 21641
      /14

      Est $209,778 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,760 Sq Ft

      21984 Main St, Hillsboro, MD 21641

      21984 Main St, Hillsboro, MD 21641
    • 22060 Main St, Hillsboro, MD 21629
      22060 Main St, Hillsboro, MD 21629
      22060 Main St, Hillsboro, MD 21629
      /12

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      22060 Main St, Hillsboro, MD 21629

      22060 Main St, Hillsboro, MD 21629
    • 11192 Maple Ave, Hillsboro, MD 21641
      11192 Maple Ave, Hillsboro, MD 21641
      11192 Maple Ave, Hillsboro, MD 21641
      /30

      Est $590,810 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 4,065 Sq Ft

      11192 Maple Ave, Hillsboro, MD 21641

      11192 Maple Ave, Hillsboro, MD 21641
    • 22052 Church St, Hillsboro, MD 21629
      22052 Church St, Hillsboro, MD 21629
      22052 Church St, Hillsboro, MD 21629
      /13

      Not Listed For Sale

      • 2 Beds
      • 1.5 Baths

      22052 Church St, Hillsboro, MD 21629

      22052 Church St, Hillsboro, MD 21629
    • 21914 Main St, Hillsboro, MD 21629
      21914 Main St, Hillsboro, MD 21629
      21914 Main St, Hillsboro, MD 21629
      /10

      Not Listed For Sale

      • 2 Beds
      • 1 Bath

      21914 Main St, Hillsboro, MD 21629

      21914 Main St, Hillsboro, MD 21629
    • 22101 Main St, Hillsboro, MD 21629
      22101 Main St, Hillsboro, MD 21629
      22101 Main St, Hillsboro, MD 21629
      /67

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,980 Sq Ft

      22101 Main St, Hillsboro, MD 21629

      22101 Main St, Hillsboro, MD 21629
    • 21908 Main St, Hillsboro, MD 21629
      21908 Main St, Hillsboro, MD 21629
      21908 Main St, Hillsboro, MD 21629
      /15

      Not Listed For Sale

      • 2 Beds
      • 4.5 Baths
      • 1,920 Sq Ft

      21908 Main St, Hillsboro, MD 21629

      21908 Main St, Hillsboro, MD 21629
    • 21936 Main St, Federalsburg, MD 21632
      21936 Main St, Federalsburg, MD 21632
      21936 Main St, Federalsburg, MD 21632
      /10

      Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,528 Sq Ft

      21936 Main St, Federalsburg, MD 21632

      21936 Main St, Federalsburg, MD 21632
    • 22033 Main St, Hillsboro, MD 21641
      22033 Main St, Hillsboro, MD 21641
      22033 Main St, Hillsboro, MD 21641
      /5

      Not Listed For Sale

      • Studio
      • 2,320 Sq Ft

      22033 Main St, Hillsboro, MD 21641

      22033 Main St, Hillsboro, MD 21641
    • 22104 Main St, Hillsboro, MD 21641
      22104 Main St, Hillsboro, MD 21641
      22104 Main St, Hillsboro, MD 21641
      /14

      Est $192,105 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      22104 Main St, Hillsboro, MD 21641

      22104 Main St, Hillsboro, MD 21641
    • 22028 Main St, Hillsboro, MD 21641
      22028 Main St, Hillsboro, MD 21641
      22028 Main St, Hillsboro, MD 21641
      /43

      Est $315,440 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,392 Sq Ft

      22028 Main St, Hillsboro, MD 21641

      22028 Main St, Hillsboro, MD 21641
    • 22018 Church St, Hillsboro, MD 21641
      22018 Church St, Hillsboro, MD 21641
      22018 Church St, Hillsboro, MD 21641
      /12

      Est $340,872 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,040 Sq Ft

      22018 Church St, Hillsboro, MD 21641

      22018 Church St, Hillsboro, MD 21641
    • 0 Md Route 404 Unit 1007611772, Hillsboro, MD 21641
      0 Md Route 404 Unit 1007611772, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      0 Md Route 404 Unit 1007611772, Hillsboro, MD 21641

      0 Md Route 404 Unit 1007611772, Hillsboro, MD 21641
    • 0 Md Route 404 Unit 1007611518, Hillsboro, MD 21641
      0 Md Route 404 Unit 1007611518, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      0 Md Route 404 Unit 1007611518, Hillsboro, MD 21641

      0 Md Route 404 Unit 1007611518, Hillsboro, MD 21641
    • 0 Denton Rd 404 Unit 1007138384, Hillsboro, MD 21641
      0 Denton Rd 404 Unit 1007138384, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      0 Denton Rd 404 Unit 1007138384, Hillsboro, MD 21641

      0 Denton Rd 404 Unit 1007138384, Hillsboro, MD 21641
    • 11419 Ridgely Rd, Hillsboro, MD 21641
      11419 Ridgely Rd, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      • 1 Bath

      11419 Ridgely Rd, Hillsboro, MD 21641

      11419 Ridgely Rd, Hillsboro, MD 21641
    • 0 Denton Rd 404 Unit 1006952752, Hillsboro, MD 21641
      0 Denton Rd 404 Unit 1006952752, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      0 Denton Rd 404 Unit 1006952752, Hillsboro, MD 21641

      0 Denton Rd 404 Unit 1006952752, Hillsboro, MD 21641
    • 0 Denton Rd 404 Unit 1006892656, Hillsboro, MD 21641
      0 Denton Rd 404 Unit 1006892656, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      0 Denton Rd 404 Unit 1006892656, Hillsboro, MD 21641

      0 Denton Rd 404 Unit 1006892656, Hillsboro, MD 21641
    • 0 Shore Hwy Unit 1000190534, Hillsboro, MD 21641
      0 Shore Hwy Unit 1000190534, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      0 Shore Hwy Unit 1000190534, Hillsboro, MD 21641

      0 Shore Hwy Unit 1000190534, Hillsboro, MD 21641
    • 11339 Ridgely Rd, Hillsboro, MD 21641
      11339 Ridgely Rd, Hillsboro, MD 21641
      /2

      Not Listed For Sale

      • 9,600 Sq Ft

      11339 Ridgely Rd, Hillsboro, MD 21641

      11339 Ridgely Rd, Hillsboro, MD 21641
    • 22008 Main St, Hillsboro, MD 21641
      22008 Main St, Hillsboro, MD 21641
      /2

      Est $214,610 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,974 Sq Ft

      22008 Main St, Hillsboro, MD 21641

      22008 Main St, Hillsboro, MD 21641

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