15,675

Caroline County, MD Homes

Section Image Section Image
  • 19 S 8th St, Denton, MD 21629
    19 S 8th St, Denton, MD 21629
    19 S 8th St, Denton, MD 21629
    /9

    $225,000 Sold Jun 11, 2025

    19 S 8th St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1981

    Last Sold Summary

    • $260/SF
    • 9 Days On Market

    Current Estimated Value $243,634

    Last Listing Agent Myisha Walker Long & Foster Real Estate, Inc.

    19 S 8th St, Denton, MD 21629
    • 111 Fooks Ave, Preston, MD 21655
      111 Fooks Ave, Preston, MD 21655
      111 Fooks Ave, Preston, MD 21655
      /14

      Est $383,987 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft

      111 Fooks Ave, Preston, MD 21655

      111 Fooks Ave, Preston, MD 21655
  • 21948 Main St, Hillsboro, MD 21641
    21948 Main St, Hillsboro, MD 21641
    21948 Main St, Hillsboro, MD 21641
    /20

    $174,500

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

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill across from the Tuckahoe Creek with some winter views of the water. --the park across the street has 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 room to the right and then the dining room and

    Bonnie Duley Long & Foster Real Estate, Inc.

    21948 Main St, Hillsboro, MD 21641
  • 1105 Market St, Denton, MD 21629
    1105 Market St, Denton, MD 21629
    1105 Market St, Denton, MD 21629
    /29

    $261,000 Sold Jan 13, 2026

    1105 Market St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 2021

    Last Sold Summary

    • $201/SF
    • 85 Days On Market

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    1105 Market St, Denton, MD 21629
    • 113 Noble Ave, Preston, MD 21655
      113 Noble Ave, Preston, MD 21655
      113 Noble Ave, Preston, MD 21655
      /38

      Est $261,865 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,314 Sq Ft

      113 Noble Ave, Preston, MD 21655

      113 Noble Ave, Preston, MD 21655
  • 229 Oldtown Rd, Goldsboro, MD 21636
    229 Oldtown Rd, Goldsboro, MD 21636
    229 Oldtown Rd, Goldsboro, MD 21636
    /28

    $248,999

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    229 Oldtown Rd, Goldsboro, MD 21636

    Motivated Sellers! Bring Us Your Offer! Fully Remodeled 3 Bedroom, 2 Bath Home in the Heart of Goldsboro, MD Welcome to 229 Main Street, where modern style meets small-town charm. This beautifully remodeled 3-bedroom, 2 full bath home has been thoughtfully updated from top to bottom, offering the perfect blend of craftsmanship and comfort. Step inside to a bright, open floor plan featuring luxury

    Brett Schrader Taylor Properties

    229 Oldtown Rd, Goldsboro, MD 21636
  • 13061 Logan Ln, Greensboro, MD 21639
    13061 Logan Ln, Greensboro, MD 21639
    13061 Logan Ln, Greensboro, MD 21639
    /19

    $335,000 Sold May 27, 2025

    13061 Logan Ln, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 2004

    Last Sold Summary

    • $266/SF
    • 6 Days On Market

    Current Estimated Value $355,959

    Last Listing Agent Megan Carpenter Tesla Realty Group, LLC

    13061 Logan Ln, Greensboro, MD 21639
    • 107 Fooks Ave, Preston, MD 21655
      107 Fooks Ave, Preston, MD 21655
      107 Fooks Ave, Preston, MD 21655
      /14

      Est $394,674 Not Listed For Sale

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

      107 Fooks Ave, Preston, MD 21655

      107 Fooks Ave, Preston, MD 21655
  • 28241 Hickman Cannery Rd, Denton, MD 21629
    28241 Hickman Cannery Rd, Denton, MD 21629
    28241 Hickman Cannery Rd, Denton, MD 21629
    /24

    $279,900

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    28241 Hickman Cannery Rd, Denton, MD 21629

    Welcome to 28241 Hickman Cannery Road, a refreshed two-story home in Denton, MD, blending classic charm with modern, low-maintenance updates. Luxury vinyl plank flooring runs throughout both levels, creating a cohesive, move-in-ready feel. The main level offers a bright living room, a flexible den ideal for a home office or family room, a spacious kitchen, dedicated laundry room, and a full

    Billy Mister Keller Williams Realty

    28241 Hickman Cannery Rd, Denton, MD 21629
  • 334 Deep Shore Rd, Denton, MD 21629
    334 Deep Shore Rd, Denton, MD 21629
    334 Deep Shore Rd, Denton, MD 21629
    /48

    $350,000 Sold Jan 14, 2026

    334 Deep Shore Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Built 1957

    Last Sold Summary

    • $213/SF
    • 15 Days On Market

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    334 Deep Shore Rd, Denton, MD 21629
    • 27518 Possum Hill Rd, Federalsburg, MD 21632
      27518 Possum Hill Rd, Federalsburg, MD 21632
      27518 Possum Hill Rd, Federalsburg, MD 21632
      /33

      Est $524,268 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,249 Sq Ft

      27518 Possum Hill Rd, Federalsburg, MD 21632

      27518 Possum Hill Rd, Federalsburg, MD 21632
  • 107 Smith St, Federalsburg, MD 21632
    107 Smith St, Federalsburg, MD 21632
    107 Smith St, Federalsburg, MD 21632
    /39

    $229,990

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    A must see, updated + upgraded, 1-level, 3-bedroom,1.5-bath home with an open floorplan. Situated on a nice-sized yard, this welcoming home offers more than meets the eye. Handsome + durable luxury vinyl plank flooring, fresh paint, and updated fixtures throughout. Spacious living room with a bar and radiant countertops overlook the kitchen. Dining room with breakfast bar and sliding glass door.

    Brandon Brittingham EXP Realty, LLC

    107 Smith St, Federalsburg, MD 21632
  • 124 Julie Ln, Federalsburg, MD 21632
    124 Julie Ln, Federalsburg, MD 21632
    124 Julie Ln, Federalsburg, MD 21632
    /28

    $233,990 Sold Aug 20, 2025

    124 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $171/SF
    • 20 Days On Market

    D.R. Horton Riverwalk Terrace

    124 Julie Ln, Federalsburg, MD 21632
    • 1103 Trice Meadows Cir, Denton, MD 21629
      1103 Trice Meadows Cir, Denton, MD 21629
      1103 Trice Meadows Cir, Denton, MD 21629
      /37

      Est $406,344 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,816 Sq Ft

      1103 Trice Meadows Cir, Denton, MD 21629

      1103 Trice Meadows Cir, Denton, MD 21629
  • 208 N Main St, Federalsburg, MD 21632
    208 N Main St, Federalsburg, MD 21632
    208 N Main St, Federalsburg, MD 21632
    /22

    $150,000 Pending

    • 4 Beds
    • 1.5 Baths
    • 2,668 Sq Ft

    208 N Main St, Federalsburg, MD 21632

    Traditional Victorian. 4 bedrooms, 1 1/2 baths, basement, attic, wraparound porch.Sold as is. Cash or conventional financing. Estate of Bonnie Jefferson.

    Barton Johnson/not int Marshy Hope Realty LLC

    208 N Main St, Federalsburg, MD 21632
  • 0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    /7

    $120,000 Sold Mar 20, 2025

    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660

    • Land
    • 3.75 Acres
    • $32,000 per Acre

    Last Sold Summary

    • 124 Days On Market

    Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660
    • 344 Meadow Vale Ln, Denton, MD 21629
      344 Meadow Vale Ln, Denton, MD 21629
      344 Meadow Vale Ln, Denton, MD 21629
      /19

      Est $384,011 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft

      344 Meadow Vale Ln, Denton, MD 21629

      344 Meadow Vale Ln, Denton, MD 21629
  • 120 Julie Ln, Federalsburg, MD 21632
    120 Julie Ln, Federalsburg, MD 21632
    120 Julie Ln, Federalsburg, MD 21632
    /27

    $220,990 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft

    120 Julie Ln, Federalsburg, MD 21632

    Explore 120 Julie Lane, a new home in the welcoming Riverwalk Terrace community of Federalsburg, MD. The Jefferson is an open-concept 1,365 square foot two-story interior townhome with three bedrooms, two and a half bathrooms, and on-street parking. The first floor is spacious with a large, thoughtfully designed kitchen with ample gray cabinet space, granite countertops, stainless steel

    Justin K Wood D.R. Horton Realty of Virginia, LLC

    120 Julie Ln, Federalsburg, MD 21632
  • 124 Parkland Rd, Greensboro, MD 21639
    124 Parkland Rd, Greensboro, MD 21639
    124 Parkland Rd, Greensboro, MD 21639
    /20

    $267,490 Sold Aug 12, 2025

    124 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $253/SF
    • 6 Days On Market

    D.R. Horton Kinnamon Meadows

    124 Parkland Rd, Greensboro, MD 21639
    • 12185 River Rd, Ridgely, MD 21660
      12185 River Rd, Ridgely, MD 21660
      12185 River Rd, Ridgely, MD 21660
      /13

      Est $281,801 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft

      12185 River Rd, Ridgely, MD 21660

      12185 River Rd, Ridgely, MD 21660
  • 103 Chamber St, Preston, MD 21655
    103 Chamber St, Preston, MD 21655
    103 Chamber St, Preston, MD 21655
    /12

    $125,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chamber St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chamber St, Preston, MD 21655
  • 5890 Harmony Rd, Preston, MD 21655
    5890 Harmony Rd, Preston, MD 21655
    5890 Harmony Rd, Preston, MD 21655
    /11

    $1,050,000 Sold May 16, 2025

    5890 Harmony Rd, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,264 Sq Ft
    • Built 1920

    Last Sold Summary

    • $464/SF
    • 6 Days On Market

    Current Estimated Value $1,122,331

    Last Listing Agent Nick Campanaro The Land Group

    5890 Harmony Rd, Preston, MD 21655
    • 12786 Holly Rd, Greensboro, MD 21639
      12786 Holly Rd, Greensboro, MD 21639
      12786 Holly Rd, Greensboro, MD 21639
      /12

      Est $1,703,038 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,728 Sq Ft

      12786 Holly Rd, Greensboro, MD 21639

      12786 Holly Rd, Greensboro, MD 21639
  • 515 Vaughn Ave, Greensboro, MD 21639
    515 Vaughn Ave, Greensboro, MD 21639
    515 Vaughn Ave, Greensboro, MD 21639
    /35

    $249,900

    • 4 Beds
    • 0.5 Baths
    • 1,756 Sq Ft

    515 Vaughn Ave, Greensboro, MD 21639

    This charming home in Cedar Run is set to shine with a major refresh in 2026, blending modern comforts with classic appeal. Spanning 1,756 sq. ft. , this end-of-row home offers a cozy atmosphere perfect for creating lasting memories. The spacious layout features an attached garage, providing convenience and ease. Nestled in a vibrant community, residents enjoy access to nearby parks, perfect for

    Chad Muse KD Realty Inc

    515 Vaughn Ave, Greensboro, MD 21639
  • 311 Maple Ave, Federalsburg, MD 21632
    311 Maple Ave, Federalsburg, MD 21632
    311 Maple Ave, Federalsburg, MD 21632
    /10

    $125,000 Sold Jan 15, 2026

    311 Maple Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,230 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Below List Price
    • $102/SF
    • 4 Days On Market

    Last Listing Agent Melissa Tippett TTR Sotheby's International Realty

    311 Maple Ave, Federalsburg, MD 21632
    • 24638 Tribbett Cir, Ridgely, MD 21660
      24638 Tribbett Cir, Ridgely, MD 21660
      24638 Tribbett Cir, Ridgely, MD 21660
      /36

      Est $722,203 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 4,521 Sq Ft

      24638 Tribbett Cir, Ridgely, MD 21660

      24638 Tribbett Cir, Ridgely, MD 21660
  • 3471 Laurel Grove Rd, Federalsburg, MD 21632
    3471 Laurel Grove Rd, Federalsburg, MD 21632
    /2

    $100,000 Pending

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft

    3471 Laurel Grove Rd, Federalsburg, MD 21632

    Looking for a project with potential? This 3-bedroom, 1-bath home in Federalsburg is ready for someone with vision. Offering solid bones and a large detached garage, it’s the perfect opportunity to renovate, customize, and build equity. Whether you’re an investor or a handy buyer wanting a fixer-upper, this property gives you room to make it your own. Great possibilities — bring your ideas and

    Heather Brummell Keller Williams Realty

    3471 Laurel Grove Rd, Federalsburg, MD 21632
  • 104 Roe St, Greensboro, MD 21639
    104 Roe St, Greensboro, MD 21639
    104 Roe St, Greensboro, MD 21639
    /29

    $275,000 Sold Oct 21, 2025

    104 Roe St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1948

    Last Sold Summary

    • $228/SF
    • 3 Days On Market

    Current Estimated Value $266,624

    Last Listing Agent Nora Turner Long & Foster Real Estate, Inc.

    104 Roe St, Greensboro, MD 21639
    • 1108 Trice Meadows Cir, Denton, MD 21629
      1108 Trice Meadows Cir, Denton, MD 21629
      1108 Trice Meadows Cir, Denton, MD 21629
      /12

      Est $392,357 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft

      1108 Trice Meadows Cir, Denton, MD 21629

      1108 Trice Meadows Cir, Denton, MD 21629
  • 26471 Three Bridges Rd, Federalsburg, MD 21632
    26471 Three Bridges Rd, Federalsburg, MD 21632
    26471 Three Bridges Rd, Federalsburg, MD 21632
    /14

    $140,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to customize every detail. Set on nearly a

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • 311 Reliance Ave, Federalsburg, MD 21632
    311 Reliance Ave, Federalsburg, MD 21632
    311 Reliance Ave, Federalsburg, MD 21632
    /26

    $185,000 Sold Nov 10, 2025

    311 Reliance Ave, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,224 Sq Ft
    • Built 1950

    Last Sold Summary

    • $151/SF
    • 7 Days On Market

    Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    311 Reliance Ave, Federalsburg, MD 21632
    • 17832 Henderson Rd, Marydel, MD 21649
      17832 Henderson Rd, Marydel, MD 21649
      17832 Henderson Rd, Marydel, MD 21649
      /60

      Not Listed For Sale

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

      17832 Henderson Rd, Marydel, MD 21649

      17832 Henderson Rd, Marydel, MD 21649
  • 804 Gay St, Denton, MD 21629
    804 Gay St, Denton, MD 21629
    804 Gay St, Denton, MD 21629
    /3

    $99,000

    • 2 Beds
    • 1 Bath
    • 956 Sq Ft

    804 Gay St, Denton, MD 21629

    Property is being sold in as/ is condition.

    Diane Wenk Wright Real Estate

    804 Gay St, Denton, MD 21629
  • 157 Riverwalk Terrace, Federalsburg, MD 21632
    157 Riverwalk Terrace, Federalsburg, MD 21632
    157 Riverwalk Terrace, Federalsburg, MD 21632
    /27

    $219,990 Sold Aug 14, 2025

    157 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $161/SF
    • 14 Days On Market

    Current Estimated Value $217,000

    D.R. Horton Riverwalk Terrace

    157 Riverwalk Terrace, Federalsburg, MD 21632
    • 204 S Main St, Greensboro, MD 21639
      204 S Main St, Greensboro, MD 21639
      204 S Main St, Greensboro, MD 21639
      /79

      Est $451,515 Not Listed For Sale

      • 6 Beds
      • 4.5 Baths
      • 4,546 Sq Ft

      204 S Main St, Greensboro, MD 21639

      204 S Main St, Greensboro, MD 21639
  • 0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    /22

    $510,000

    • Land
    • 63.16 Acres
    • $8,075 per Acre

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    Dover Bridge Road | Preston, MarylandThis 63 ± acre parcel on Dover Bridge Road offers a rare opportunity to own a sizeable tract of woodland conveniently located just four miles from Preston, seven and a half miles from Easton, and about fifteen minutes from Route 50.The property is perc-approved for residential use and includes a forestry management plan documenting that roughly 58

    Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
  • 4808 Frazier Neck Rd, Preston, MD 21655
    4808 Frazier Neck Rd, Preston, MD 21655
    4808 Frazier Neck Rd, Preston, MD 21655
    /30

    $435,000 Sold Aug 11, 2025

    4808 Frazier Neck Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1920

    Last Sold Summary

    • $275/SF
    • 88 Days On Market

    Current Estimated Value $454,685

    Last Listing Agent Brenda Fornos Taylor Properties

    4808 Frazier Neck Rd, Preston, MD 21655
    • 4439 Bethlehem Rd, Preston, MD 21655
      4439 Bethlehem Rd, Preston, MD 21655
      4439 Bethlehem Rd, Preston, MD 21655
      /74

      Est $556,000 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft

      4439 Bethlehem Rd, Preston, MD 21655

      4439 Bethlehem Rd, Preston, MD 21655
  • 10819 Greensboro Rd, Denton, MD 21629
    10819 Greensboro Rd, Denton, MD 21629
    10819 Greensboro Rd, Denton, MD 21629
    /3

    $265,000 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well. Coming Soon

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • 116 Julie Ln, Federalsburg, MD 21632
    116 Julie Ln, Federalsburg, MD 21632
    116 Julie Ln, Federalsburg, MD 21632
    /28

    $209,990 Sold Sep 15, 2025

    116 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $154/SF
    • 12 Days On Market

    D.R. Horton Riverwalk Terrace

    116 Julie Ln, Federalsburg, MD 21632

Showing Results 121 - 160, Page 4 of 18

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