15,671

Caroline County, MD Homes

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  • 8320 Detour Rd, Denton, MD 21629
    8320 Detour Rd, Denton, MD 21629
    8320 Detour Rd, Denton, MD 21629
    /14

    $95,000 Sold May 22, 2025

    8320 Detour Rd, Denton, MD 21629

    • Land
    • 2.09 Acres
    • $45,455 per Acre

    Last Sold Summary

    • 135 Days On Market

    Current Estimated Value $103,270

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    8320 Detour Rd, Denton, MD 21629
    • 22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft

      22510 Ash Blvd, Preston, MD 21655

      22510 Ash Blvd, Preston, MD 21655
  • 1612 Cattail Commons Way, Denton, MD 21629
    1612 Cattail Commons Way, Denton, MD 21629
    1612 Cattail Commons Way, Denton, MD 21629
    /67

    $399,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft

    1612 Cattail Commons Way, Denton, MD 21629

    Discover this charming home in the desirable Cattail Commons neighborhood. Lots of recent upgrades completed and ready for you to move-in. As you arrive, you will immediately notice the brand new white fence which is ideal for privacy and the cozy front porch for those days you wish to unwind. Open the door and you are greeted with an expansive and open floorplan with fresh paint throughout. To

    Daniel Register Northrop Realty

    1612 Cattail Commons Way, Denton, MD 21629
  • 12760 Cow Barn Rd, Ridgely, MD 21660
    12760 Cow Barn Rd, Ridgely, MD 21660
    12760 Cow Barn Rd, Ridgely, MD 21660
    /21

    $25,000 Sold Mar 18, 2025

    12760 Cow Barn Rd, Ridgely, MD 21660

    • Land
    • 3.55 Acres
    • $7,042 per Acre

    Last Sold Summary

    • 143 Days On Market

    Current Estimated Value $25,892

    Last Listing Agent Jennifer Young Keller Williams Realty

    12760 Cow Barn Rd, Ridgely, MD 21660
    • 3498 Pepper Rd, Federalsburg, MD 21632
      3498 Pepper Rd, Federalsburg, MD 21632
      3498 Pepper Rd, Federalsburg, MD 21632
      /17

      Est $491,033 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      3498 Pepper Rd, Federalsburg, MD 21632

      3498 Pepper Rd, Federalsburg, MD 21632
  • 21090 Marsh Creek Rd, Preston, MD 21655
    21090 Marsh Creek Rd, Preston, MD 21655
    21090 Marsh Creek Rd, Preston, MD 21655
    /10

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21090 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture.

    Eddie Matthews Benson & Mangold, LLC

    21090 Marsh Creek Rd, Preston, MD 21655
  • 24316 Auction Rd, Preston, MD 21655
    24316 Auction Rd, Preston, MD 21655
    24316 Auction Rd, Preston, MD 21655
    /33

    $350,000 Sold Sep 26, 2025

    24316 Auction Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1975

    Last Sold Summary

    • $243/SF
    • 19 Days On Market

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • 1211 Painted Fern Rd, Denton, MD 21629
      1211 Painted Fern Rd, Denton, MD 21629
      1211 Painted Fern Rd, Denton, MD 21629
      /14

      Est $428,238 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,238 Sq Ft

      1211 Painted Fern Rd, Denton, MD 21629

      1211 Painted Fern Rd, Denton, MD 21629
  • 0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
    /7

    $127,000

    • Land
    • 4.14 Acres
    • $30,676 per Acre

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 4.14 acres with mature trees, offering unparalleled privacy and peaceful country living in one of the area's most scenic subdivisions -- all just minutes away from Ridgely and Denton, and less than 1 mile from North Caroline High School. Build your dream home on this beautiful level building lot, providing an even terrain

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
  • 4631 Everlea Ct, Preston, MD 21655
    4631 Everlea Ct, Preston, MD 21655
    4631 Everlea Ct, Preston, MD 21655
    /26

    $475,000 Sold Oct 15, 2025

    4631 Everlea Ct, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 2,228 Sq Ft
    • Built 1997

    Last Sold Summary

    • $213/SF
    • 4 Days On Market

    Last Listing Agent Elizabeth Tryon Meredith Fine Properties

    4631 Everlea Ct, Preston, MD 21655
    • 28012 Bloomery Rd, Federalsburg, MD 21632
      28012 Bloomery Rd, Federalsburg, MD 21632
      28012 Bloomery Rd, Federalsburg, MD 21632
      /32

      Est $240,047 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,548 Sq Ft

      28012 Bloomery Rd, Federalsburg, MD 21632

      28012 Bloomery Rd, Federalsburg, MD 21632
  • 2570 Guard Rd, Federalsburg, MD 21632
    2570 Guard Rd, Federalsburg, MD 21632
    2570 Guard Rd, Federalsburg, MD 21632
    /66

    $479,900 Pending

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

    2570 Guard Rd, Federalsburg, MD 21632

    Welcome to this 3-bedroom, 2-bathroom home nestled on more than Eight acres of land, offering the perfect blend of comfort, space, and opportunity. The main level features a practical layout with three bedrooms, two full baths, and a warm, inviting living space. Upstairs, you’ll find an unfinished second story, a blank slate ideal for adding extra bedrooms, a bonus room, or a private retreat

    Thomas Burdett Keller Williams Realty

    2570 Guard Rd, Federalsburg, MD 21632
  • 125 Bloomingdale Ave, Federalsburg, MD 21632
    125 Bloomingdale Ave, Federalsburg, MD 21632
    125 Bloomingdale Ave, Federalsburg, MD 21632
    /21

    $59,900 Sold Nov 24, 2025

    125 Bloomingdale Ave, Federalsburg, MD 21632

    • 4 Beds
    • 1 Bath
    • 1,696 Sq Ft
    • Built 1875

    Last Sold Summary

    • $35/SF
    • 22 Days On Market

    Last Listing Agent Daniel Demers Sell Your Home Services

    125 Bloomingdale Ave, Federalsburg, MD 21632
    • 23904 Bridgetown Rd, Goldsboro, MD 21636
      23904 Bridgetown Rd, Goldsboro, MD 21636
      23904 Bridgetown Rd, Goldsboro, MD 21636
      /15

      Est $210,961 Not Listed For Sale

      • Studio
      • 1,608 Sq Ft

      23904 Bridgetown Rd, Goldsboro, MD 21636

      23904 Bridgetown Rd, Goldsboro, MD 21636
  • 116 Stonesifer Dr, Greensboro, MD 21639
    116 Stonesifer Dr, Greensboro, MD 21639
    116 Stonesifer Dr, Greensboro, MD 21639
    /19

    $189,900 Under Contract

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    116 Stonesifer Dr, Greensboro, MD 21639

    Charming Updated Cottage in the Heart of Greensboro, MD Welcome home to this beautiful 2-bedroom, 1-bath rancher offering the perfect blend of comfort and modern style. Step inside to find a bright, open-concept living space featuring warm wood floors, recessed lighting, and a cozy family room that flows seamlessly into the stunning kitchen. The kitchen boasts upgraded cabinetry, butcher block

    Brett Schrader Taylor Properties

    116 Stonesifer Dr, Greensboro, MD 21639
  • 143 Riverwalk Terrace, Federalsburg, MD 21632
    143 Riverwalk Terrace, Federalsburg, MD 21632
    143 Riverwalk Terrace, Federalsburg, MD 21632
    /27

    $219,990 Sold Aug 29, 2025

    143 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $161/SF
    • 6 Days On Market

    Current Estimated Value $231,366

    Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

    143 Riverwalk Terrace, Federalsburg, MD 21632
    • 1901 Blue Heron Dr, Denton, MD 21629
      1901 Blue Heron Dr, Denton, MD 21629
      1901 Blue Heron Dr, Denton, MD 21629
      /33

      Est $282,887 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,640 Sq Ft

      1901 Blue Heron Dr, Denton, MD 21629

      1901 Blue Heron Dr, Denton, MD 21629
  • 0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
    /46

    $75,000 Under Contract

    • Land
    • 8.43 Acres
    • $8,897 per Acre

    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632

    Bring your imagination to this gorgeous 8.43 wooded acreage in Federalsburg! No current permits pulled! No builder tie in! This property was perc approved back in the 1980's & owner hasn't done anything with it since. No well or septic currently on property.

    Megan Rosendale Rosendale Realty

    0 Iron Gate Rd Unit MDCM2004762, Federalsburg, MD 21632
  • 517 Gay St, Denton, MD 21629
    517 Gay St, Denton, MD 21629
    517 Gay St, Denton, MD 21629
    /46

    $330,000 Sold Apr 15, 2025

    517 Gay St, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,734 Sq Ft
    • Built 1957

    Last Sold Summary

    • $88/SF
    • 213 Days On Market

    Current Estimated Value $365,575

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    517 Gay St, Denton, MD 21629
    • 25938 Beauchamp Branch Rd, Denton, MD 21629
      25938 Beauchamp Branch Rd, Denton, MD 21629
      25938 Beauchamp Branch Rd, Denton, MD 21629
      /38

      Est $454,245 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft

      25938 Beauchamp Branch Rd, Denton, MD 21629

      25938 Beauchamp Branch Rd, Denton, MD 21629
  • 406 Morning Glory Dr, Denton, MD 21629
    406 Morning Glory Dr, Denton, MD 21629
    406 Morning Glory Dr, Denton, MD 21629
    /50

    $410,000

    • 4 Beds
    • 2.5 Baths
    • 2,731 Sq Ft

    406 Morning Glory Dr, Denton, MD 21629

    2020-BUILT EASTERN SHORE COLONIAL EXUDES CHARM & HOSPITALITY ! On the outskirts of historic Denton, you will find this 4-bedroom, 2.5 bathroom home in the pleasant neighborhood of “The Gardens!" This one-owner home offers high-end detailing including a fresh decorator neutral paint palette, free-flowing open concept floor plan, beautiful NEW carpeting, as well as luxury vinyl tile flooring, a

    Mary Stevens Long & Foster Real Estate, Inc.

    406 Morning Glory Dr, Denton, MD 21629
  • 11145 Branch Ct, Denton, MD 21629
    11145 Branch Ct, Denton, MD 21629
    11145 Branch Ct, Denton, MD 21629
    /36

    $375,000 Sold Jun 30, 2025

    11145 Branch Ct, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1999

    Last Sold Summary

    • $279/SF
    • 82 Days On Market

    Current Estimated Value $408,236

    Last Listing Agent Sean O'Connor Coldwell Banker Realty

    11145 Branch Ct, Denton, MD 21629
    • 22354 Hillsboro Rd, Denton, MD 21629
      22354 Hillsboro Rd, Denton, MD 21629
      22354 Hillsboro Rd, Denton, MD 21629
      /21

      Est $349,446 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      22354 Hillsboro Rd, Denton, MD 21629

      22354 Hillsboro Rd, Denton, MD 21629
  • 3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    3547 Prchal Rd, Preston, MD 21655
    /46

    $875,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 3,149 Sq Ft

    3547 Prchal Rd, Preston, MD 21655

    Pride of ownership shines throughout this home, lovingly maintained since 1992. A major renovation in 2006 nearly doubled the living space, transforming this property into a spacious 4-bedroom, 3-bathroom home ideal for comfortable living and entertaining.The impressive 20' x 27' kitchen is the heart of the home, featuring cherry cabinetry, quartz countertops, a walk-in pantry, and a cozy

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • 505 Market St, Denton, MD 21629
    505 Market St, Denton, MD 21629
    505 Market St, Denton, MD 21629
    /13

    $225,000 Sold Aug 15, 2025

    505 Market St, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 3,731 Sq Ft
    • Built 1890

    Last Sold Summary

    • $60/SF
    • 148 Days On Market

    Current Estimated Value $254,662

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    505 Market St, Denton, MD 21629
    • 24565 Holsinger Ln, Ridgely, MD 21660
      24565 Holsinger Ln, Ridgely, MD 21660
      24565 Holsinger Ln, Ridgely, MD 21660
      /33

      Est $424,576 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft

      24565 Holsinger Ln, Ridgely, MD 21660

      24565 Holsinger Ln, Ridgely, MD 21660
  • 14990 Greensboro Rd, Goldsboro, MD 21636
    14990 Greensboro Rd, Goldsboro, MD 21636
    14990 Greensboro Rd, Goldsboro, MD 21636
    /51

    $399,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    14990 Greensboro Rd, Goldsboro, MD 21636

    Considerable Price Improvement! This property is being sold as/is to settle an estate. Bring your horse, goats, pigs and sheep. This 3 bedroom, 2 bath Cape has additional unfinished space on the second floor. Partially wooded with a fenced pasture and barn with 4 stalls. With a few upgrades and some TLC, this private home on 5+ acres could be your paradise.

    Andrew Beaven Wright Real Estate

    14990 Greensboro Rd, Goldsboro, MD 21636
  • 12805 Kibler Rd, Greensboro, MD 21639
    12805 Kibler Rd, Greensboro, MD 21639
    12805 Kibler Rd, Greensboro, MD 21639
    /27

    $1,350,000 Sold Jan 24, 2025

    12805 Kibler Rd, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft
    • Built 1900

    Last Sold Summary

    • $811/SF
    • 212 Days On Market

    Current Estimated Value $858,377

    Last Listing Agent Nick Campanaro The Land Group

    12805 Kibler Rd, Greensboro, MD 21639
    • 22700 Thawley Rd, Denton, MD 21629
      22700 Thawley Rd, Denton, MD 21629
      22700 Thawley Rd, Denton, MD 21629
      /24

      Est $479,085 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft

      22700 Thawley Rd, Denton, MD 21629

      22700 Thawley Rd, Denton, MD 21629
  • 158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    158 Wright St, Preston, MD 21655
    /34

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    158 Wright St, Preston, MD 21655
  • 106 Morning Glory Dr, Denton, MD 21629
    106 Morning Glory Dr, Denton, MD 21629
    106 Morning Glory Dr, Denton, MD 21629
    /41

    $382,000 Sold Jun 06, 2025

    106 Morning Glory Dr, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2022

    Last Sold Summary

    • $230/SF
    • 254 Days On Market

    Current Estimated Value $405,130

    Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

    106 Morning Glory Dr, Denton, MD 21629
    • 24911 Woods Dr, Denton, MD 21629
      24911 Woods Dr, Denton, MD 21629
      24911 Woods Dr, Denton, MD 21629
      /36

      Est $550,573 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,222 Sq Ft

      24911 Woods Dr, Denton, MD 21629

      24911 Woods Dr, Denton, MD 21629
  • 0 Laurel Ln, Denton, MD 21629
    0 Laurel Ln, Denton, MD 21629
    0 Laurel Ln, Denton, MD 21629
    /6

    $85,000

    • Land
    • 1.15 Acres
    • $73,913 per Acre

    0 Laurel Ln, Denton, MD 21629

    Beautiful, wooded lot ready to be built on available in established Forest Landing. Conveniently located between Denton and Easton. Lot has approved perc for a 4 bedroom mound system. Community offers a private beach area, picnic tables, great spot to launch your canoe or kayak or do a little fishing. Not many opportunities to build your next home in a mature neighborhood left around.

    Michael Bozek Michael J. Bozek

    0 Laurel Ln, Denton, MD 21629
  • 22879 Stevenson Rd, Ridgely, MD 21660
    22879 Stevenson Rd, Ridgely, MD 21660
    22879 Stevenson Rd, Ridgely, MD 21660
    /121

    $835,000 Sold Jun 06, 2025

    22879 Stevenson Rd, Ridgely, MD 21660

    • 5 Beds
    • 5 Baths
    • 5,328 Sq Ft
    • Built 2012

    Last Sold Summary

    • $157/SF
    • 47 Days On Market

    Current Estimated Value $892,908

    Last Listing Agent Chris Rosendale CR Realty

    22879 Stevenson Rd, Ridgely, MD 21660
    • 25400 Calvert Dr, Greensboro, MD 21639
      25400 Calvert Dr, Greensboro, MD 21639
      25400 Calvert Dr, Greensboro, MD 21639
      /31

      Est $386,337 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,742 Sq Ft

      25400 Calvert Dr, Greensboro, MD 21639

      25400 Calvert Dr, Greensboro, MD 21639
  • 113 Maple Ave, Goldsboro, MD 21636
    113 Maple Ave, Goldsboro, MD 21636
    113 Maple Ave, Goldsboro, MD 21636
    /17

    $230,000

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    113 Maple Ave, Goldsboro, MD 21636

    Welcome to the pleasures of small town living in this updated Farmhouse. This 3 bed 2 bath home sits on a .23 acre lot with most of the land in the backyard for relaxing and entertaining. Plenty of room for gardens or playground area. Outbuilding for extra storage. Enjoy the evenings on the back deck overlooking the yard or enjoy the front porch with coffee and listen to the rain.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    113 Maple Ave, Goldsboro, MD 21636
  • Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    /3

    $85,000 Sold Sep 16, 2025

    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632

    • Land
    • 2 Acres
    • $42,500 per Acre

    Last Sold Summary

    • 160 Days On Market

    Last Listing Agent Mickey Hayward Sunset Properties

    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    • 9605 Quail Run Rd, Denton, MD 21629
      9605 Quail Run Rd, Denton, MD 21629
      9605 Quail Run Rd, Denton, MD 21629
      /21

      Est $508,600 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,646 Sq Ft

      9605 Quail Run Rd, Denton, MD 21629

      9605 Quail Run Rd, Denton, MD 21629
  • 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

    $286,990 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
  • 5059 Gina Ln, Federalsburg, MD 21632
    5059 Gina Ln, Federalsburg, MD 21632
    5059 Gina Ln, Federalsburg, MD 21632
    /31

    $280,000 Sold Jul 24, 2025

    5059 Gina Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1981

    Last Sold Summary

    • $192/SF
    • 120 Days On Market

    Current Estimated Value $290,823

    Last Listing Agent Andrew Beaven Wright Real Estate

    5059 Gina Ln, Federalsburg, MD 21632

Showing Results 161 - 200, Page 5 of 18

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